NetApp, Inc. v. Albert E. Cinelli ( 2023 )


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  •     IN THE COURT OF CHANCERY OF THE STATE OF DELAWARE
    NETAPP, INC.,                 )
    )
    Plaintiff,         )
    )
    )
    v.                       )               C.A. No. 2020-1000-LWW
    )
    ALBERT E. CINELLI, AL.E.C     )
    HOLDING CORP., AEC CAPITAL    )
    CORPORATION, THE ALBERT E.    )
    CINELLI AND SHARON A. CINELLI )
    2014 REVOCABLE TRUST, JOHN    )
    CINELLI, JANET CINELLI, DAVID )
    GIBSON, GRANT TERRELL and     )
    KELSEY MACLENNAN,             )
    )
    Defendants.
    MEMORANDUM OPINION
    Date Submitted: April 21, 2023
    Date Decided: August 2, 2023
    A. Thompson Bayliss, Matthew L. Miller, Joseph A. Sparco, Peter C. Cirka &
    Anthony R. Sarna, ABRAMS & BAYLISS LLP, Wilmington, Delaware; Counsel
    for Plaintiff NetApp, Inc.
    Robert A. Penza, Stephen J. Kraftschik & Christina B. Vavala, POLSINELLI PC,
    Wilmington, Delaware; Robert V. Spake, Jr., POLSINELLI PC, Kansas City,
    Missouri; Britton St. Onge, POLSINELLI PC, St. Louis, Missouri; Counsel for
    Defendants Albert E. Cinelli, AL.E.C Holding Corp., AEC Capital Corporation, The
    Albert E. Cinelli and Sharon A. Cinelli 2014 Revocable Trust, John Cinelli, Janet
    Cinelli, David Gibson, Grant Terrell, and Kelsey MacLennan
    WILL, Vice Chancellor
    “Let the buyer beware” is a common legal maxim. In this case, “let the seller
    be forthright” is more apt.
    Cloud Jumper, a struggling private company, recorded internal software use
    as revenue in its unaudited financial statements. The company’s management team
    knew about this practice; its Chief Executive Officer had requested it. But when the
    opportunity arose to sell the company to plaintiff NetApp, Inc., Cloud Jumper kept
    quiet about the so-called internal billing. After closing, NetApp discovered the
    problem when Cloud Jumper’s financial results fell short of expectations. This
    lawsuit for breach of contract and fraud followed.
    The defendants accept that Cloud Jumper breached representations about its
    financial condition in the parties’ merger agreement.       They insist that these
    misrepresentations were inadvertent. They also aver that NetApp was not damaged
    by Cloud Jumper’s silence.
    After trial, judgment is entered in favor of NetApp. Cloud Jumper breached
    multiple representations in the merger agreement, including that its financial
    statements were GAAP-compliant and reflected bona fide transactions. These
    misstatements and others amount to fraud. NetApp also proved that it was damaged
    by Cloud Jumper.
    That leaves the quantification of NetApp’s damages—by far the murkiest
    issue before me. The parties agree in theory that expectation damages are the proper
    1
    approach, but they lack a shared understanding of what that means in application.
    There is even less accord when it comes to their competing measures for valuing
    NetApp’s expectations. After wading through this morass, I discover some firm
    footing and calculate NetApp’s damages to be just under $4.6 million.
    I.      FACTUAL BACKGROUND
    The following facts were stipulated to by the parties or proven by a
    preponderance of the evidence at trial.1 Trial was held over three days, during which
    four fact witnesses and three expert witnesses testified live. The trial record includes
    508 exhibits and 16 deposition transcripts.
    A.     Cloud Jumper’s Business Lines
    Cloud Jumper LLC f/k/a Cloud Jumper Corporation is a Delaware limited
    liability company that provided a platform for delivering virtual desktop
    infrastructure (VDI), storage, and data management across cloud-based programs.2
    Defendant Albert E. Cinelli was Cloud Jumper’s Chairman and Chief Executive
    Officer and owned about 90% of the company.3 Cinelli is a lawyer by training and
    1
    Joint Pre-trial Stipulation and Proposed Order (Dkt. 69) (“PTO”). Facts drawn from the
    exhibits jointly submitted by the parties are referred to by the numbers provided on the
    parties’ joint exhibit list (cited as “JX __” unless otherwise defined). Deposition transcripts
    are cited as “[Name] Dep.” Trial testimony is cited as “[Name] Tr.” See Dkts. 91-93.
    2
    PTO ¶ 2.
    3
    Id. ¶ 3; JX 267 at Tab 4. For clarity, this decision refers to Albert Cinelli as “Cinelli.”
    John Cinelli and Janet Cinelli are referred to by their full names.
    2
    worked as an in-house corporate attorney before becoming an entrepreneur. He has
    participated in about 50 mergers and acquisitions during his career.4
    Cinelli acquired Cloud Jumper in 2004. At the time, he also controlled Q
    Services, which provided back-office support to Cloud Jumper, and MetroNet—a
    fiber optic services company.5 In 2010, Cinelli sold Cloud Jumper’s parent company
    for consideration worth $818 million, spinning off Cloud Jumper, Q Services, and
    MetroNet in the process.6 He remains the Chairman of MetroNet, which he and his
    son John Cinelli (MetroNet’s CEO) have built into a multi-billion-dollar enterprise.7
    Before February 2018, Cloud Jumper was a Managed Service Provider (MSP)
    that delivered a bundled suite of third-party software to customers and provided
    ongoing support and administration.8 Cloud Jumper did not have a VDI product of
    its own;9 its MSP “Legacy Business” depended on VDI software licenses from a
    separate company called IndependenceIT.10 In exchange for a VDI software license,
    4
    Cinelli Tr. 419, 464.
    5
    JX 310 (“Larson Dep.”) 89; JX 339 (“John Cinelli Dep.”) 75, 124, 128; PTO ¶ 13.
    6
    JX 13 at 5; John Cinelli Dep. 123, 142.
    7
    John Cinelli Dep. 26; see JX 430.
    8
    PTO ¶ 23.
    9
    VDI technology enables desktops to be centrally hosted and managed, removing the need
    to maintain individual systems in data centers or server rooms. See id. ¶¶ 43-44; see also
    Revised Expert Report of Gary Kleinrichert (Dkt. 85; JX 341) (“Kleinrichert Revised
    Opening Rep.”) 20-22.
    10
    See Expert Report of George S. Hickey (Dkt. 85; JX 327) (“Hickey Opening Rep.”)
    ¶¶ 6-7; Kleinrichert Revised Opening Rep. 10-11.
    3
    Cloud Jumper paid IndependenceIT a monthly fee for each Legacy Business end
    user.11 Cloud Jumper was responsible for 45% of IndependenceIT’s revenues.12
    In February 2018, Cloud Jumper acquired IndependenceIT. The transaction
    eliminated significant Legacy Business expenses. It also allowed Cloud Jumper to
    pursue a second line of business using IndependenceIT’s software (the “Software
    Business”) and access the growing VDI market.13 Cinelli financed the transaction
    with a $5.2 million loan from his affiliated entity, the Albert E. Cinelli and Sharon
    A. Cinelli 2014 Revocable Trust (the “Trust”).14
    The MSP-based Legacy Business remained Cloud Jumper’s primary source
    of revenue. Cloud Jumper expected to drive future growth by focusing on the
    Software Business while phasing out the Legacy Business.15
    B.    The Internal Billing Practice
    After the IndependenceIT acquisition closed, Cinelli instructed Sherri
    VanFossen to track Cloud Jumper’s financial results as if the transaction had not
    happened.16 VanFossen, an accountant employed by MetroNet and Q Services,
    11
    PTO ¶ 27.
    12
    Id.
    13
    Id. ¶ 25; see JX 424; Picarello Tr. 27; see also Kleinrichert Revised Opening Rep. 11.
    14
    JX 23. A yearly 5% interest rate applied.
    15
    PTO ¶¶ 24, 28; see Picarello Tr. 10, 19.
    16
    See JX 324 (“Cinelli Dep.”) 37 (“I gave her a direction that I wanted all the
    IndependenceIT sales included in IndependenceIT, period. I had let her figure out how to
    4
    acted as Cloud Jumper’s de facto Chief Financial Officer.17 Cinelli told VanFossen
    to track software sales attributable to IndependenceIT, which included revenue from
    the Legacy Business’s use of IndependenceIT’s VDI product.18                    VanFossen
    expressed concern with this approach.19 Cinelli overruled her.20
    Consequently, in February 2018, VanFossen implemented an accounting
    practice of “billing” Cloud Jumper for using its own VDI licenses. Each VDI
    software license sale was recorded as a Legacy Business “expense” and as Software
    Business “revenue,” as if the two lines of business were distinct companies. 21 This
    so-called “Internal Billing” practice was well known among Cloud Jumper
    management. Beyond VanFossen and Cinelli, Cloud Jumper President John “JD”
    Helms, Head of Sales Max Pruger, and Chief Operating Officer Frank Picarello were
    aware of it.22
    do it. She’s an accountant. I’m not an accountant. And she went ahead and did it and
    didn’t tell me how she did it.”).
    17
    Picarello Tr. 22. VanFossen retired in 2021. PTO ¶ 21.
    18
    JX 313 (“VanFossen Dep.”) 56-57; Cinelli Tr. 425-27; PTO ¶ 29; see also JX 306
    (“Helms Dep.”) 49-50.
    19
    VanFossen Dep. 59-60 (recalling that she told Cinelli his requested process was “not the
    right way” to prepare financial reports because “you would not report revenue . . . or costs
    to yourself” if “[t]here was no exchange of cash”).
    20
    See Cinelli Dep. 37; VanFossen Dep. 59 (“He said that’s what I want to see.”).
    21
    VanFossen Dep. 51-53.
    22
    See Picarello Tr. 45-46; Cinelli Tr. 484, 488, 491; JX 319 (“Picarello Dep.”) 23-27;
    Helms Dep. 29, 67-68; PTO ¶¶ 17-18.
    5
    Although Cinelli and VanFossen never discussed the mechanics of the
    Internal Billing practice after Cinelli’s initial instruction, the two regularly reviewed
    Cloud Jumper’s financials.23 Software Business revenue reports made the Internal
    Billing obvious.24 “[A]ny of the key reports . . . sorted by revenue would have Cloud
    Jumper as a partner listed, if not at the top, right near the top.”25
    C.     Cloud Jumper’s Internal Rate Hike
    Cloud Jumper required periodic capital infusions from Cinelli.26 Cinelli grew
    concerned about the company’s lack of revenue generation and “heavy cash burn,”27
    which required his continued financial support. His goal was for Cloud Jumper to
    become “cash flow positive.”28
    Cloud Jumper struggled to meet Cinelli’s expectations.29 By early 2019,
    Cinelli began to pressure Cloud Jumper management to increase sales.30 In March,
    23
    Cinelli Tr. 426-27, 449-51; VanFossen Dep. 126 (explaining that she and Cinelli would
    “go over the financials” “every month”); see also John Cinelli Dep. 175-76, 191.
    24
    See VanFossen Dep. 84-86; Picarello Tr. 28.
    Picarello Tr. 28, 31 (“It was . . . widely understood that the company was doing this.”);
    25
    VanFossen Dep. 215-16.
    26
    PTO ¶ 34.
    27
    JX 15.
    28
    Id.
    29
    See JX 28.
    30
    Id.
    6
    he wrote to Helms that he was considering “terminat[ing] all our sales people” to
    “reduce our cash burn” or—short of that—“terminating all sales commissions.”31
    On June 14, Pruger suggested to Helms that Cloud Jumper “should change
    [its] internal billing and bill [itself] $10/mth for the software” to “increase [its]
    software revenue.”32 At the time, Cloud Jumper was “billing” itself $3.75 per month
    for each VDI software license.33 Helms responded: “Lol . . . already told finance
    that.”34 Six days later, Helms instructed Cloud Jumper’s billing department to
    increase the Internal Billing rate to $8.00 per license—a 113% increase.35 This was
    nearly twice the rate charged to outside customers with similar use volumes.36
    Because Cloud Jumper billed in arrears, its financial statements first showed
    greater revenue from the Internal Billing rate change in July 2019.37 Cloud Jumper
    management knew about the increase.38 Cinelli considered it a “good business
    31
    JX 30.
    32
    JX 33.
    33
    See PTO ¶ 31.
    34
    JX 32.
    35
    JX 35; see PTO ¶ 31; Hughes Tr. 556-57.
    36
    Expert Report of Ann H. Hughes (Dkt. 85; JX 328) (“Hughes Expert Rep.”) ¶¶ 22, 53 &
    Tbl.2; Hughes Tr. 551-58.
    37
    JX 40.
    38
    Picarello Tr. 45-46; VanFossen Dep. 82-84 (“Q. So this increase, when it hit the financial
    statements that Al reviewed, did he know that Cloud Jumper was bringing in less money
    than stated on the financial statements? . . . [A.]: Yes.”); see also Helms Dep. 64.
    7
    decision” because it “increased [Cloud Jumper’s] revenue.”39 The increase, of
    course, was only on paper.40
    D.    Preliminary Talks with NetApp
    Cloud Jumper’s unprofitability remained an issue throughout the summer of
    2019. In August, Cinelli told Helms that his “goal [wa]s to sell the business in
    2020.”41 Cinelli said that Helms stood to gain “over $5 million in profit” from a
    sale.42
    By October 2019, Cloud Jumper was communicating with plaintiff
    NetApp, Inc., a data management company, about a potential “alliance.”43 NetApp,
    which drew its business predominately from the sale of data storage appliances,
    believed that the VDI market was poised for high growth and desired to expand its
    cloud-based business.44
    In November, the NetApp team charged with overseeing strategic transactions
    received approval to investigate a VDI acquisition.45 After a market assessment,
    39
    Cinelli Tr. 429, 483-84, 493-94.
    40
    See Picarello Tr. 28.
    41
    JX 37.
    42
    Id.
    43
    JX 39.
    44
    PTO ¶¶ 40-42, 44; JX 316 (“Mitzenmacher Dep.”) 21, 25.
    45
    Mitzenmacher Dep. 21, 63-64.
    8
    Cloud Jumper was identified as a target.46 Cloud Jumper was attractive to NetApp
    because of possible Software Business growth and revenue generation opportunities
    from combining Cloud Jumper software with NetApp storage products.47
    By January 2020, NetApp and Cloud Jumper were engaged in preliminary
    merger negotiations.48 On January 17, Helms traveled to NetApp headquarters for
    the parties’ first formal meeting.49 The meeting included a session on potential
    synergies between NetApp and Cloud Jumper.50 Helms reported to Cinelli that the
    “[m]eeting and company presentation went well” with “1.5 hours” of the 5-hour
    meeting “focused on Company synergies.”51 Three days later, NetApp requested
    information about Cloud Jumper’s historical revenues and revenue forecasts.52
    E.        The Management Projections
    On January 22, Cinelli told Helms that he could “no longer sustain . . .
    operating losses” and that the “only alternative” was for Cloud Jumper to “cut
    expenses as soon as possible in the range of $200,000 to $250,000 per month.”53
    46
    PTO ¶ 45; JX 322 (“Lye Dep.”) 21.
    47
    Lye Dep. 159, 191.
    48
    Mitzenmacher Tr. 96-99.
    49
    Id. at 98-105.
    50
    JX 75 at 7.
    51
    JX 57.
    52
    JX 69; Mitzenmacher Tr. 105-06.
    53
    JX 72.
    9
    Cinelli wanted Helms’s “entire focus to be on getting sales and selling the
    company.”54 This “threat” was intended to motivate Helms.55
    As for the potential merger, Cinelli was “interested in negotiating directly”
    with NetApp “to squeeze a little more out of them.”56 Cinelli told Helms that at an
    $80 million sale price, Helms’s “gain would be in excess of $1.5 [m]illion.”57 Helms
    promised Cinelli that he would “get [Cinelli] out of this burden . . . with a significant
    profit.”58
    An hour after this exchange with Cinelli, Helms sent Cloud Jumper’s
    historical financial statements to NetApp.59              The Software Business revenue
    recorded in the financial statements was overstated by more than 40% due to Internal
    Billing.60 Cloud Jumper also submitted interim financials to NetApp with similarly
    inflated Software Business revenue.61
    54
    Id.; see also Picarello Tr. 24-25.
    55
    Cinelli Tr. 499-500; see also Picarello Tr. 24-25.
    56
    JX 72.
    57
    Id.; see also Helms Dep. 81-82 (recalling that he was promised a bonus of $1.5 million
    or 10% of the sale price).
    58
    JX 71.
    59
    JX 69.
    60
    Hickey Opening Rep. ¶ 28 & Tbl.2.
    61
    See JX 439; JX 408; JX 284.
    10
    On January 27, Helms sent NetApp three-year projections Cloud Jumper
    management had prepared to predict future revenues and revenue growth rates (the
    “Management Projections”).62 Helms’s cover email told NetApp that the forecasting
    was “not that sophisticated” and doubled software revenue each year.63 Because
    Cloud Jumper projected that Software Business revenue would double year-over-
    year from a baseline that included Internal Billing, the revenue overstatement was
    compounded.64
    Cloud Jumper did not indicate that its financial statements and Management
    Projections included Internal Billing.65
    On February 4, Cinelli asked his team for copies of information provided to
    NetApp during negotiations.66 Cinelli was told by corporate counsel, Brian Nelson,
    that Cloud Jumper had shared historical financial statements and the Management
    Projections with NetApp.67 Helms then forwarded Cinelli the documents NetApp
    had received.68
    62
    See JX 408; JX 284; JX 55; JX 78; PTO ¶ 64.
    63
    JX 78; see also Picarello Tr. 33-36.
    64
    See Picarello Tr. 111; see Hickey Tr. 696.
    65
    Mitzenmacher Tr. 107-13.
    66
    JX 97.
    67
    JX 114. Nelson was an employee of MetroNet and Q Services. PTO ¶ 19.
    68
    JX 114; see also Helms Dep. 186.
    11
    F.     NetApp’s Valuation Model
    NetApp’s in-house deal team was tasked with valuing Cloud Jumper before
    its Investment Committee would approve a letter of intent (LOI).69 NetApp relied
    on the financial submissions from Helms to build a pre-LOI valuation model.70 Its
    deal team created a revised set of standalone projections for Cloud Jumper (the
    “Standalone Projections”) based on the Management Projections.71                 It also
    developed projections for Cloud Jumper as a unit of NetApp (the “Combined
    Projections”) that reflected synergy opportunities.72 NetApp projected that Cloud
    Jumper’s Software Business revenue would grow to $38.4 million by 2024.73 It
    estimated a total enterprise value of $86.2 million for Cloud Jumper as a unit of
    NetApp.74
    NetApp’s cross-functional teams approved the Standalone and Combined
    Projections.75 NetApp then prepared discounted cash flow (DCF) analyses based on
    the projections, a precedent transactions analysis, and a trading comparables analysis
    69
    See PTO ¶¶ 50-51.
    70
    See Mitzenmacher Tr. 121-22, 201; JX 408; JX 284; see also JX 93.
    71
    See Mitzenmacher Tr. 121; Hickey Opening Rep. ¶ 12.
    72
    Mitzenmacher Tr. 126-31, 137-38; Hickey Tr. 681-82.
    73
    See JX 354 at 3; Hickey Opening Rep. at Tbl.6.
    74
    See JX 129 at 41; see also Hickey Opening Rep. ¶¶ 48, 53 & Ex. 1. This was the midpoint
    estimate.
    75
    Mitzenmacher Tr. 124, 127-32; see JX 233 at 25.
    12
    to “triangulate” a purchase price.76 NetApp felt that the “quality of revenue” would
    be the “primary argument on valuation.”77
    A slide deck prepared for NetApp’s Investment Committee stated that “[last
    twelve month] Revenue at ~$13.5M and ~20% [year over year] growth comfortably
    support[ed] a price range below $45M.”78 An initial purchase price of “$38.5 million
    including retention” was proposed.79             The Investment Committee approved
    proceeding with an acquisition of Cloud Jumper for up to $40 million.80
    G.      The Letter of Intent and Due Diligence
    On February 14, 2020, NetApp sent Cinelli a non-binding LOI to acquire
    Cloud Jumper for $36 million.81 On February 24, NetApp reduced the proposed
    purchase price to $35 million to fund the retention of Cloud Jumper employees who
    would not receive merger consideration.82
    The parties executed the LOI on February 25.83 Cinelli signed for Cloud
    Jumper and former Vice President, Corporate Development Steven Mitzenmacher
    76
    JX 318 (“Avadhanam Dep.”) 133, 275; Mitzenmacher Tr. 251-52, 257; see JX 129.
    77
    JX 81 at 1.
    78
    JX 129 at 8.
    79
    Id.
    80
    PTO ¶¶ 69, 73.
    81
    JX 130; JX 131.
    82
    See JX 139 at 2-3; see also JX 138.
    83
    PTO ¶ 77; JX 142.
    13
    signed for NetApp.84 The LOI stated that “customary representations, warranties
    and covenants” would be prepared in a definitive agreement.85
    Due diligence followed amid the COVID-19 pandemic in March and April
    2020.86 Cinelli planned for the worst. In March, he told Picarello to be “ready for
    big cuts” if “the deal f[ell] through.”87 Picarello relayed this statement to Helms.88
    Cinelli also shared with Cloud Jumper management his frustration over large
    monthly expenses and declining sales, identifying layoffs as the solution.89
    On March 19, Helms wrote to Picarello: “If the deal doesn’t happen the
    company probably dies and does so quickly. We have to do whatever it takes to get
    over the final hurdles.”90 At the same time, Helms informed NetApp that Cinelli
    might “change his mind” about the deal because Cloud Jumper would “see revenue
    from three major opportunities in 60 days.”91 There is no evidence in the record
    about such opportunities.
    84
    JX 142 at 4.
    85
    Id. at Ex. A § F.
    86
    PTO ¶ 78; see Cinelli Dep. 86.
    87
    See JX 407.
    88
    Id.
    89
    See JX 201 (“[B]ecause of the lack of sales, I believe we still [have] too much staff that
    is non-productive.”); JX 427 (“The heavy cash burn must end.”); Picarello Tr. 38-39; see
    also JX 413; JX 96.
    90
    JX 168.
    91
    JX 173 at 1 (relaying information from Cloud Jumper); see Mitzenmacher Tr. 372-73.
    14
    H.    Top Customers and Top Partners
    Cloud Jumper prepared early drafts of disclosure schedules for an eventual
    merger agreement, including a list of “Top Partners” and “Top Customers.” Top
    Customers was defined to mean Cloud Jumper’s “top twenty (20) customers
    (measured by revenue derived from such customers during the applicable period) for
    the 12-month period ended February 29, 2020.”92 Top Partners meant Cloud
    Jumper’s “top twenty (20) partners (measured by revenue derived from such partners
    during the applicable period) for the 12-month period ended February 29, 2020.”93
    On April 2, 2020, Nelson asked Picarello to obtain the raw data needed to
    populate the schedules.94 Picarello retrieved the information from Cloud Jumper’s
    billing system and sent it to Nelson and Helms in a spreadsheet.95 The spreadsheet
    identified Cloud Jumper as its own largest “Software Partner” measured by
    revenue.96
    92
    JX 206.
    93
    Id.
    94
    Id.
    95
    JX 217; JX 218; Picarello Tr. 53-56.
    96
    JX 218 (“Software Partners” tab); see also JX 228; JX 431.
    15
    Nelson excluded Cloud Jumper from the Top Customers and Top Partners
    lists because it was neither a customer nor a partner.97          Cinelli reviewed the
    disclosure schedules with Nelson before they were shared with NetApp.98 On April
    16, Nelson sent NetApp the final disclosure schedules.99
    I.       The Merger Agreement
    On April 17, Cinelli executed an Agreement and Plan of Merger (the “Merger
    Agreement”) for NetApp to acquire Cloud Jumper.100 The Merger Agreement
    included a series of representations by Cloud Jumper, including that:
    • its financial statements were “prepared in accordance with GAAP”
    (the “GAAP Compliance Representation”);101
    • its financial statements “fairly present[ed] in all material respects,
    the financial condition of the Company on a consolidated basis at
    the dates therein indicated and the results of operations and cash
    flows of the Company on a consolidated basis” (the “Fairly Presents
    Representation”);102
    • the transactions in its “books of account and other financial
    records . . . represent[ed] bona fide transactions, and the revenues,
    expenses, assets and liabilities of the Company [were] properly
    97
    See JX 305 (“Nelson Dep.”) 178-82 (describing discussions with Picarello about “the
    difference between a customer and a partner” and recalling that Picarello determined that
    “Cloud Jumper was not considered a partner”); JX 431; see also Picarello Tr. 59-60.
    98
    Cinelli Dep. 147.
    99
    JX 243; JX 235; see Cinelli Tr. 489.
    100
    JX 240 (“Merger Agreement”); PTO ¶ 80.
    101
    Merger Agreement § 2.7(b)(iii).
    102
    Id. § 2.7(b)(iv).
    16
    recorded therein in all material respects” (the “Bona Fide
    Transactions Representation”);103
    • the disclosure schedules “set[] forth a list of the Company’s Top
    Customers [and] Top Partners” (the “Top Relationships
    Representation”);104
    • “[n]one of the representations or warranties made by the
    Company . . . , and none of the statements made in any exhibit,
    schedule or certificate furnished by the Company . . . contain[ed], or
    w[ould] contain at the Closing, any untrue statement of a material
    fact, or omit[ted] or w[ould] omit at the Closing to state any material
    fact necessary in order to make the statements contained . . . therein,
    in light of the circumstances under which made, not misleading”
    (the “Full Disclosure Representation”);105 and
    • the “estimates, projections or forecasts provided to [NetApp] were
    prepared in good faith based on assumptions that the Company
    believed reasonable as of the date of such projections or forecasts”
    (the “Reasonable Assumptions Representation”).106
    J.        The Closing
    Before closing, Cloud Jumper was required to submit an officer’s
    certificate.107 The bring-down statements in the officer’s certificate confirmed the
    accuracy of Cloud Jumper’s representations. Cinelli was the signatory and attested
    103
    Id. § 2.7(c).
    104
    Id. § 2.26.
    105
    Id. § 2.29.
    106
    Id. § 2.30.
    107
    Id. § 7.2(k); see Larson Tr. 397.
    17
    that the representations in the Merger Agreement were “true and correct, in all
    material respects.”108
    Meanwhile, Cinelli and Helms’s relationship had ruptured. Helms believed
    that Cinelli had promised him “at least 1.5 million dollars” for “staying to drive the
    business and get[ting] [Cinelli] a buyer.”109 He worried that Cinelli did not “want to
    write the check and resent[ed] him.”110 On April 22, Helms reminded Cinelli that
    he was “promised” a “minimum of $1.5 million at exit.”111 He told Cinelli that “no
    one else could have delivered” the deal and said: “take care of me and my family as
    I took care of you and yours.”112
    The merger closed on April 28 for a purchase price of $35 million, $5.25
    million of which was deposited into an indemnity escrow account.113 After closing,
    Cinelli told Helms that there were “no funds” available for a bonus.114 They
    eventually agreed that Helms would receive $300,000, payable in three
    108
    JX 264.
    109
    JX 230.
    110
    Id.
    111
    JX 256.
    112
    Id.
    113
    PTO ¶ 115.
    114
    JX 269.
    18
    installments.115 The first installment of $75,000 was paid to Helms soon after
    closing;116 the other installments remain unpaid.117
    K.    NetApp’s Discovery of the Internal Billing
    Helms and Picarello became NetApp employees. On June 7, 2020, Helms
    received an email from NetApp Executive Vice President Anthony Lye that
    questioned Cloud Jumper’s poor performance in the month after closing, with a
    revenue disparity of $2 million on an annualized basis.118 Helms forwarded the
    email to Picarello within minutes of receipt, asking: “Could this be the internal
    charge for software that [Cinelli] charged[?]”119
    Less than an hour later, Picarello responded to Helms that the “[g]ood [n]ews”
    was he felt “confident [they] did not misrepresent the revenue as part of the [due
    diligence] process.”120         Picarello wrote:     “I reviewed the submissions with
    [VanFossen] and the internal charge was removed.”121                The “[b]ad [n]ews,”
    115
    JX 271; see Cinelli Tr. 463; Cinelli Dep. 79-80, 96.
    116
    Helms Dep. 148.
    117
    Id. at 148-49.
    118
    JX 275 (“JD where is [sic] the difference of approximately $2M gone?”); PTO ¶ 117.
    119
    JX 275.
    120
    JX 277.
    121
    Id.
    19
    however, was that “data used to develop the pro-forma included the cross charge and
    . . . the foundation for the baseline.”122
    Helms did not relay this information to NetApp. Instead, he responded to Lye
    that he could “only think of one thing” causing the discrepancy: the migration of a
    large customer to a new contract.123
    Separately, Picarello emailed VanFossen: “I am assuming that the revenue
    submissions sent to NetApp during the [due diligence] phase did not include the
    internal categorized ‘CloudJumper’ revenue that was a charge for software . . . Can
    you confirm?”124 On June 8, she responded: “It was included.”125 VanFossen said
    that she had not been “asked about” the internal charge during NetApp’s diligence
    of Cloud Jumper and did not “know if [Helms] was asked about [it] or not.”126
    NetApp fired Helms shortly after discovering the Internal Billing.127
    A month later, NetApp decided to sunset Cloud Jumper’s VDI software,
    despite the product functioning as expected.128 Cloud Jumper’s former employees
    122
    Id.; see also JX 278; JX 280.
    123
    JX 276; see Picarello Tr. 66-67.
    124
    JX 278.
    125
    Id.
    126
    Id.; JX 280.
    127
    Mitzenmacher Tr. 190, 361.
    128
    Lye Dep. 228-29.
    20
    were transferred into Spot, Inc.—another business NetApp had recently acquired—
    to work on launching a different VDI platform.129
    L.        Procedural History
    On November 20, 2020, NetApp filed a Verified Complaint in this court
    against defendants Cinelli, AL.E.C Holding Corp., AEC Capital Corporation, the
    Trust, John Cinelli, Janet Cinelli, David Gibson, Grant Terrell and Kelsey
    MacLennan.130 AL.E.C Holding was a party to the Merger Agreement.131 AEC
    Capital and the Trust were signatories to Lender Payoff and Joinder Agreements, in
    which they agreed to be bound by the provisions of the Merger Agreement.132
    Cinelli, John Cinelli, Janet Cinelli, Gibson, Terrell, and MacLennan had entered into
    Consent, Joinder, and Support Agreements “agree[ing] to be bound by the provisions
    of the Merger Agreement applicable to Company Stockholders.”133
    NetApp alleged that Cloud Jumper committed fraud by including Internal
    Billing in the financial statements and projections it sent NetApp, making false
    representations in the Merger Agreement, and manipulating Cloud Jumper’s
    129
    Id. at 229.
    130
    Dkt. 1.
    131
    Merger Agreement at 72 (signature page).
    132
    JX 268 at 10, 21 (signature pages).
    133
    JX 248 at 13, 30, 47, 64, 81, 98 (signature pages).
    21
    financial data.134       NetApp also alleged that Cloud Jumper breached several
    representations in the Merger Agreement.135
    On January 21, 2021, the defendants answered the Complaint.136 Discovery
    ensued over the next eighteen months.
    Trial was held from July 26 to July 28, 2022. Post-trial briefing and argument
    followed.137 After the parties submitted native expert exhibits to the court on
    April 21, 2023, the matter was deemed submitted for decision.
    II.      LEGAL ANALYSIS
    The defendants concede that Cloud Jumper breached certain representations
    in the Merger Agreement. The parties disagree on whether other representations
    were breached and whether Cloud Jumper committed fraud, which would obviate
    the Merger Agreement’s $5.25 million indemnity cap on recoverable losses.138 They
    further dispute NetApp’s damages.
    134
    Compl. ¶ 108.
    135
    Id. ¶¶ 125-34. The Complaint also contained a claim for failing to disclose the loss of
    a top partner, which was withdrawn before trial. See PTO ¶ 119.
    136
    Dkt. 11.
    137
    Dkts. 94, 96, 99, 101-02.
    138
    See PTO ¶¶ 100-03.
    22
    After trial, I reach three essential conclusions. Cloud Jumper breached
    multiple representations in the Merger Agreement. Cloud Jumper committed fraud.
    And NetApp is entitled to damages of $4,598,978.
    A.     Breach of Contract
    “Under Delaware law, the elements of a breach of contract claim are: 1) a
    contractual obligation; 2) a breach of that obligation by the defendant; and 3)
    resulting damage to the plaintiff.”139 The first element is met because the Merger
    Agreement is a valid and enforceable contract. The defendants concede that Cloud
    Jumper breached the GAAP Compliance Representation and the Fairly Presents
    Representation.140 But they maintain that Cloud Jumper did not breach the Bona
    Fide Transactions Representation, the Top Relationships Representation, the Full
    Disclosure Representation, or the Reasonable Assumptions Representation.141
    Each of these provisions involves the same general issue. Cloud Jumper
    represented that it was forthright with NetApp about Cloud Jumper’s financial
    condition and prospects. It was not; Cloud Jumper’s financial statements and related
    139
    H-M Wexford LLC v. Encorp, Inc., 
    832 A.2d 129
    , 140 (Del. Ch. 2003).
    140
    PTO ¶¶ 84-85; Cinelli Tr. 466-67; see also Larson Tr. 401-02; Hughes Tr. 534-43, 561-
    70; Kleinrichert Tr. 851-52; see supra notes 101-02 and accompanying text; Merger
    Agreement § 2.7(b)(iii)-(iv).
    141
    See supra notes 103-06 and accompanying text; Merger Agreement Art. II. The
    defendants also aver that NetApp failed to prove damages for breaches of the GAAP
    Compliance and Fairly Presents Representations. See infra Section II.B.5.
    23
    representations were misleading as they pertained to Cloud Jumper’s Software
    Business. NetApp proved that each of the disputed provisions were breached, except
    for the Top Relationships Representation.
    1.      Bona Fide Transactions Representation
    Cloud Jumper represented in Section 2.7(c) of the Merger Agreement that “the
    transactions entered [into its books of account and other financial records]
    represent[ed] bona fide transactions.”142 This representation assures the quality of
    the seller’s recordkeeping and is “especially important where separate audited
    financial statements have not been prepared.”143
    The defendants aver that NetApp failed to prove that the Bona Fide
    Transactions Representation was inaccurate.144 Yet Cinelli testified that it was
    false.145 The evidence supports Cinelli’s testimony.
    “When the contract is clear and unambiguous,” Delaware courts will “give
    effect to the plain meaning of the contract’s terms and provisions.”146 “Bona fide”
    142
    Merger Agreement § 2.7(c).
    143
    Am. Bar Ass’n, Model Stock Purchase Agreement 100 (2d ed. 2010); see also
    Mitzenmacher Tr. 155-57 (testifying that Cloud Jumper’s representations “gave [NetApp]
    comfort” where it lacked audited financial statements).
    144
    See Defs.’ Answering Post-trial Br. (Dkt. 96) (“Defs.’ Post-trial Br.”) 29 n.13.
    145
    Cinelli Tr. 468; Cinelli Dep. 130.
    146
    Osborn ex rel. Osborn v. Kemp, 
    991 A.2d 1153
    , 1159-60 (Del. 2010) (citing Rhone-
    Poulenc Basic Chem. Co. v. Am. Motorists Ins. Co., 
    616 A.2d 1192
    , 1195 (Del. 1992)).
    24
    is not defined in the Merger Agreement.147 According to Black’s Law Dictionary,
    the term means “sincere; genuine.”148 “Genuine,” in turn, is defined as “authentic
    or real; having the quality of what a given thing purports to be or to have.”149 The
    Internal Billings reflected in Cloud Jumper’s financial statements were not genuine.
    NetApp’s expert Ann H. Hughes, a Managing Director of Coherent
    Economics, explained that bona fide transactions on financial statements reflect
    “revenues from a third party.”150 The Internal Billings lacked economic substance.
    There was no inflow of cash from a third party to Cloud Jumper.151
    The defendants’ only rebuttal is that Cloud Jumper charged itself a “market”
    rate for internal software usage, which was somehow “passed on to the end
    customers.”152 That is beside the point. The Internal Billing transactions listed on
    147
    Cf. Merger Agreement at App. I.
    148
    Bona fide, Black’s Law Dictionary (11th ed. 2019); see Lorillard Tobacco Co. v. Am.
    Legacy Found., 
    903 A.2d 728
    , 738 (Del. 2006) (explaining that Delaware courts “look to
    dictionaries for assistance in determining the plain meaning” of contractual terms).
    149
    Genuine, Black’s Law Dictionary (11th ed. 2019).
    150
    Hughes Tr. 546-60. Hughes is a Managing Director at Coherent Economics. She has a
    bachelor’s degree in accounting, an M.B.A. from the University of Chicago Booth School
    of Business, and is a Certified Public Accountant and Chartered Financial Analyst. Hughes
    has worked in various financial, accounting, and expert roles. Hughes Expert Rep. ¶¶ 1-9.
    151
    See Hughes Tr. 560 (explaining that the Internal Billings “fail to satisfy GAAP criteria
    for revenue recognition”); Hughes Expert Rep. ¶¶ 48-55; see also VanFossen Dep. 60
    (“There was no exchange of cash.”).
    152
    Defs.’ Post-trial Br. 29 n.13.
    25
    the financial statements Cloud Jumper gave NetApp were not genuine. The Bona
    Fide Transactions Representation was thus breached.
    2.     Full Disclosure and Reasonable Assumptions Representations
    In Section 2.29, Cloud Jumper promised that the representations in the Merger
    Agreement and “statements made in any . . . schedule or certificate furnished by the
    Company” were not materially false or misleading.153 The GAAP Compliance,
    Fairly Presents, and Bona Fide Transactions Representations contained untrue
    statements of material fact. It follows that the Full Disclosure Representation was
    also breached.154
    Cloud Jumper represented in Section 2.30(A) of the Merger Agreement that
    “any estimates, projections or forecasts provided to [NetApp] were prepared in good
    faith based on assumptions that the Company believed reasonable as of the date of
    such projections or forecasts.”155 The Management Projections were based on
    historical financial statements that included Internal Billings and compounded the
    153
    Merger Agreement § 2.29.
    154
    See Am. Bar Ass’n, Model Merger Agreement, 104 (2011) (observing that similar
    representations should be subject to “a strict liability standard” based on “materiality,
    regardless of the target’s good faith attempts to make the disclosure schedules as complete
    and accurate as possible”); cf. Rubén Kraiem, Leaving Money on the Table: Contract
    Practice in a Low-Trust Environment, 42 Colum. J. Transnat’l. L. 715, 724 (2004)
    (describing “full-disclosure representation” provisions as “a catch-all that incorporates a
    securities anti-fraud standard”).
    155
    Merger Agreement § 2.30; see Mitzenmacher Tr. 184.
    26
    Internal Billings’ effect on Software Business projected revenues.156 For example,
    more than 40% of the Software Business revenues forecast for 2023 were
    attributable to Internal Billing.157
    The defendants did not address this provision in their post-trial brief, waiving
    any related argument.158 In any event, as described below, Cloud Jumper’s inclusion
    of Internal Billings in its Management Projections cannot be excused as a good faith
    mistake.159 The Reasonable Assumptions Representation was breached.
    3.     Top Relationships Representation
    Cloud Jumper’s Top Customers and Top Partners were described in
    Section 2.26 of the Merger Agreement disclosure schedules.160 The Top Customers
    and Top Partners listed in the schedules were “measured by revenue derived from”
    them.161 NetApp asserts that the Top Relationships Representation was breached
    156
    See Hickey Tr. 712-14.
    157
    Id. at 696; compare Hickey Opening Rep. at Tbl.2 (identifying Internal Billing revenue
    as 42% of Software Business revenues in 2018 and 43% in 2019) with id. at Tbl.3
    (projecting software revenue growth that included Internal Billings) and id. at Tbl.4
    (comparing revenue projections with Internal Billings included and Internal Billings
    removed).
    158
    See Oxbow Carbon & Minerals Hldgs., Inc. v. Crestview-Oxbow Acq., LLC, 
    202 A.3d 482
    , 502 n.77 (Del. 2019) (“The practice in the Court of Chancery is to find that an issue
    not raised in post-trial briefing has been waived, even if it was properly raised pre-trial.”).
    159
    See infra Section II.B.2.
    160
    Merger Agreement § 2.26.
    161
    Id. at App. I (definitions of “Top Customers” and “Top Partners”).
    27
    because Cloud Jumper did not list itself as a Top Customer or Top Partner—despite
    Cloud Jumper’s internal data suggesting otherwise.162
    NetApp’s position is undercut by the fact that the Internal Billings were
    neither GAAP compliant nor bona fide transactions. If the Internal Billings did not
    represent an influx of revenue from a third party, then Cloud Jumper was not its own
    Top Customer or Top Partner as those terms are defined in the Merger Agreement.163
    Although the Top Relationships Representation forms part of a pattern of fraudulent
    conduct by Cloud Jumper, excluding Cloud Jumper from the list of Top Customers
    and Top Partners did not breach the Merger Agreement.164
    B.      Fraud
    Section 8.2(a) of the Merger Agreement permits indemnification claims by
    NetApp against the “Beneficial Indemnity Holders” for “Losses” incurred from
    “Fraud committed by the Company or its stockholders, Affiliates, employees or
    representations . . . upon which NetApp acted in reliance.”165                   The Merger
    162
    Pl.’s Post-trial Opening Br. (Dkt. 94) 24.
    Defs.’ Post-trial Br. 33-34. Hughes agreed with this view. See Hughes Tr. 641-43;
    163
    Hughes Dep. 148-49.
    164
    See infra Section II.B.
    165
    See Merger Agreement § 8.2(a); id. at App. I (d)-(c). “Losses” is defined as “all claims,
    losses, liabilities, damages, deficiencies, taxes, costs, interest, awards, judgments, penalties
    and expenses, including reasonable attorneys’ and consultants’ fees and expenses and
    including any such expenses incurred in connection with investigating, defending against
    or settling any of the foregoing; provided, that any punitive damages shall not be included
    in the definition of Losses unless actually paid or obligated to be paid to a third party.”
    28
    Agreement        defines   “Fraud”     as    “fraud,    willful   breach     or   intentional
    misrepresentation, as determined by a final and non-appealable judgment, upon
    which [NetApp] acted in justifiable reliance and which resulted in actual
    damages.”166
    The elements of common law fraud are:
    (1) a false representation, usually one of fact, made by the
    defendant; (2) the defendant’s knowledge or belief that the
    representation was false, or was made with reckless indifference
    to the truth; (3) an intent to induce the plaintiff to act or to refrain
    from acting; (4) the plaintiff’s action or inaction taken in
    justifiable reliance upon the representation; and (5) damage to
    the plaintiff as a result of such reliance.167
    Each element of fraud must be proven by a preponderance of the evidence.168
    Id. § 1.1(f). The Beneficial Indemnity Holders and their respective “Indemnity Allocation
    Percentages” are: Cinelli (31.47%); John Cinelli (2.34%); Janet Cinelli (0.13%); David
    Gibson (0.07%); Grant Terrell (0.07%); Kelsey MacLennan (0.01%); AEC Capital
    Corporation (39.39%); and the Trust (26.53%). Id. at App. I (ll); JX 267 at Tab 4; PTO
    ¶¶ 96-97.
    166
    Merger Agreement at App. I(ee) (defining “Fraud”).
    167
    Stephenson v. Capano Dev., Inc., 
    462 A.2d 1069
    , 1074 (Del. 1983); see also Great Hill
    Equity P’rs IV, LP v. SIG Growth Equity Fund I, LLLP, 
    2018 WL 6311829
    , at *32 (Del.
    Ch. Dec. 3, 2018) (citing E.I. DuPont de Nemours & Co. v. Fla. Evergreen Foliage, 
    744 A.2d 457
    , 461-62 (Del. 1999)).
    168
    See Arwood v. AW Site Servs., LLC, 
    2022 WL 705841
    , at *21 (Del. Ch. Mar. 9, 2022);
    Stone & Paper Invs., LLC v. Blanch, 
    2021 WL 3240373
    , at *26 (Del. Ch. July 30, 2021)
    (“Under Delaware law, a plaintiff must prove fraud by a preponderance of the evidence.”
    (citing In re IBP, Inc. S’holders Litig., 
    789 A.2d 14
    , 54 (Del. Ch. 2001))). The Court of
    Chancery has questioned whether a higher standard of proof is required for fraud claims.
    See, e.g., Project Boat Hldgs., LLC v. Bass Pro Grp., LLC, 
    2019 WL 2295684
    , at *23 (Del.
    Ch. May 29, 2019) (“There is some uncertainty in our law as to whether a plaintiff asserting
    fraud must prove the claim by clear and convincing evidence or whether a preponderance
    of the evidence will suffice.”). The weight of authority in Delaware applies a
    29
    1.       False Representations
    Under Delaware law, “fraud can occur in one of three ways: (1) an overt
    misrepresentation; (2) silence in the face of a duty to speak; or (3) active
    concealment of material facts.”169
    There were several overt misrepresentations in the Merger Agreement.170
    The individuals responsible for these misrepresentations were Cloud Jumper officers
    and directors.171 Their knowledge and acts are imputed to Cloud Jumper.172
    Cloud Jumper’s Top Relationships Representation was not explicitly false.173
    Nor did Cloud Jumper actively conceal that it was, in some respects, its own top
    preponderance standard to fraud claims. E.g., Roma Landmark Theaters, LLC v. Cohen
    Exhibition Co. LLC, 
    2021 WL 2182828
    , at *8 n.12 (Del. Ch. May 28, 2021); Trascent
    Mgmt. Consulting, LLC v. Bouri, 
    2018 WL 4293359
    , at *17 (Del. Ch. Sept. 10, 2018).
    Neither party advocates otherwise.
    169
    In re Am. Int’l Grp., Inc., Consol. Deriv. Litig., 
    965 A.2d 763
    , 804 (Del. Ch. 2009), aff’d
    sub nom. Tchrs.’ Ret. Sys. of La. v. PricewaterhouseCoopers LLP, 
    11 A.3d 228
     (Del. 2011)
    (TABLE).
    170
    See supra Section II.A (analyzing breaches of these representations).
    171
    See JX 243 at 2.
    172
    See, e.g., Teachers’ Ret. Sys. of La. v. Aidinoff, 
    900 A.2d 654
    , 671 n. 23 (Del. Ch. 2006)
    (“[I]t is the general rule that knowledge of an officer or director of a corporation will be
    imputed to the corporation.”); Metro Commc’n Corp. BVI v. Advanced Mobilecomm Techs.
    Inc., 
    854 A.2d 121
    , 153-55 (Del. Ch. 2004) (imputing fraud to the corporation where the
    manager of a limited liability corporation designated by the corporation made false
    statements); Nolan v. E. Co., 
    241 A.2d 885
    , 891 (Del. Ch. 1968) (“Knowledge of an agent
    acquired while acting within the scope of his authority is imputable to the principal.”), aff’d
    sub nom. Nolan v. Hershey, 
    249 A.2d 45
     (Del. 1969); New Enter. Assocs. 14, L.P. v. Rich,
    
    292 A.3d 112
    , 140 n.15 (Del. Ch. 2023).
    173
    See supra notes 163-64 and accompanying text.
    30
    customer and top partner.174 Cloud Jumper was, however, “silen[t] in the face of a
    duty to speak”175 about this reality.
    A duty to speak can arise before the consummation of a business transaction
    when a party acquires information that is “necessary to prevent [a] partial or
    ambiguous statement of the facts from being misleading.”176               An incomplete
    statement can amount to fraud when a party “purports to tell the whole truth” but
    fails to “disclose the additional information necessary to prevent the statement from
    misleading the recipient.”177 If Cloud Jumper had been forthcoming with NetApp,
    it would have explained that though it was not technically a Top Customer or Top
    174
    See Metro Commc’n, 854 A.3d at 150 (describing deliberate concealment as taking
    “some action affirmative in nature or designed or intended to prevent, and which does
    prevent, the discovery of facts giving rise to the fraud claim, some artifice to prevent
    knowledge of the facts or some representation intended to exclude suspicion and prevent
    inquiry” (quoting Lock v. Schreppler, 
    426 A.2d 856
    , 860 (Del. Super. 1981))). According
    to NetApp, Nelson and Helms revised the data Picarello pulled from Cloud Jumper’s
    billing system to hide the Internal Billings. See supra notes 94-99 and accompanying text;
    see also Pl.’s Post-trial Opening Br. 15-17. But the record lacks evidence of manipulation.
    The raw data identified Cloud Jumper as its own leading “Software Partner.” JX 218 at
    “Software Partners” tab; see also JX 217; Picarello Tr. 53. A tab of the spreadsheet called
    “Total >$25K” listed the companies from which Cloud Jumper received more than $25,000
    in revenue during 2019. JX 217; JX 218. Cloud Jumper was not included. The spreadsheet
    subsequently created by Nelson continued to list Cloud Jumper as its top “Software
    Partner” but—consistent with the raw data—did not list Cloud Jumper in the “Total >$25k”
    tab of Top Partners and Top Customers. JX 228 at “Software Partners” & “Total >$25K”
    tabs. The Top Partners and Top Customers lists later sent to NetApp likewise excluded
    Cloud Jumper. See JX 235; JX 243 at 63-64, 96.
    175
    Stephenson, 
    462 A.2d at 1074
    .
    176
    Restatement (Second) of Torts § 551(2)(b) (1977).
    177
    Id. § 551 cmt. g.
    31
    Partner as defined in the Merger Agreement, its internal records listed Cloud Jumper
    as its own leading Software Business partner.178 Cloud Jumper personnel never
    disclosed this information to NetApp, despite sharing financial statements that they
    knew included—but did not identify—Internal Billings.179
    2.    Scienter
    “After showing that a false representation was made, a plaintiff must show
    that the defendant had knowledge of the falsity of the representation or made the
    representation with reckless indifference to the truth.”180 Direct evidence of a
    defendant’s state of mind is not necessary to prove scienter. Rather, a plaintiff need
    only present “facts ‘establishing a motive and an opportunity to commit fraud’” or
    “constitut[ing] circumstantial evidence of either reckless or conscious behavior.”181
    “In cases where a fraud claim centers on a transaction, the transaction itself may
    serve as both the motive and opportunity to commit the fraud.”182
    178
    See JX 228; supra notes 162-64 and accompanying text.
    179
    See Picarello Tr. 61 (testifying that the disclosure schedules to Section 2.26 should have
    included Cloud Jumper to be “consistent with the data submissions”); VanFossen Dep.
    119.
    180
    Great Hill, 
    2018 WL 6311829
    , at *32.
    181
    Deloitte LLP v. Flanagan, 
    2009 WL 5200657
    , at *8 (Del. Ch. Dec. 29, 2009) (quoting
    Weiner v. Quaker Oats Co., 
    129 F.3d 310
     (3d Cir. 1997)); see also Maverick Therapeutics,
    Inc. v. Harpoon Therapeutics, Inc. (Maverick I), 
    2020 WL 1655948
    , at *29 (Del. Ch. Apr.
    3, 2020) (“Such scienter may be demonstrated through circumstantial evidence, including
    demonstrating motive and opportunity for inducement.”).
    182
    Maverick I, 
    2020 WL 1655948
    , at *29.
    32
    It is a close call on whether Cloud Jumper personnel intended to deceive
    NetApp with statements they knew were false.183 But there is no doubt that Cloud
    Jumper was reckless. Recklessness is more than “inexcusable negligence.”184 It is
    “a conscious disregard for the truth” departing from the ordinary standard of care.185
    Put differently, “[r]ecklessness requires ‘a conscious indifference to the decision’s
    foreseeable results,’”186 but not “[a] deliberate state of mind.”187
    The Internal Billing practice was implemented at Cinelli’s request.188 It was
    “common knowledge” at Cloud Jumper.189 Upper level management knew that there
    183
    Helms is closest to the line. See Helms Dep. 67. He shared Cloud Jumper’s financial
    statements and projections with NetApp, while believing that he would receive millions of
    dollars in the event of a sale. After the sale, when confronted by Lye about the revenue
    shortfall, he obfuscated. See supra notes 118-23 and accompanying text. Still, I hesitate
    to find that he acted intentionally without the benefit of his live testimony.
    184
    In re Wayport, Inc. Litig., 
    76 A.3d 296
    , 326 (Del. Ch. 2013) (citing Metro Commc’n,
    854 A.2d at 143).
    185
    Maverick I, 
    2020 WL 1655948
    , at *28 (describing recklessness as “a conscious
    disregard for the truth”); see also In re Wayport, Inc. Litig., 
    76 A.3d 296
    , 326 (Del. Ch.
    2013); Great Hill, 
    2018 WL 6311829
     (describing recklessness as “an extreme departure
    from the standards of ordinary care” (quoting Deloitte, 
    2009 WL 5200657
    , at *8)).
    186
    Wolf v. Magness Constr. Co., 
    1994 WL 728831
    , at *5 (Del. Ch. Dec. 20, 1994) (citation
    omitted).
    187
    Express Scripts, Inc. v. Bracket Hldgs. Corp., 
    248 A.3d 824
    , 834 (Del. 2021); see also
    Restatement (Third) of Torts: Liab. for Econ. Harm § 10(c) (2020) (noting that “‘reckless’
    has a range of meanings in the law” and that “[t]he recklessness sufficient to support a
    claim of fraud occurs when a speaker acts in conscious disregard of a risk that a statement
    is false, as by offering it without qualification while knowing that it may well be untrue”).
    188
    See Cinell Tr. 425-27; Helms Dep. 49-50; VanFossen Dep. 56-57.
    189
    Cinelli Tr. 488-91; see id. at 482-83, 526-27; Picarello Tr. 28, 30-31; JX 33; JX 32;
    JX 35; PTO ¶¶ 29-30; VanFossen Dep. 56-57.
    33
    was “no real revenue associated” with the Internal Billings.190 Company officers
    joked about raising the Internal Billing rate days before a 113% increase was
    implemented.191 Cloud Jumper officers also knew that the Internal Billings were
    recorded on Cloud Jumper’s financials.192 Cinelli, for one, acknowledged that
    tracking of the Internal Billings was “artificial[]” and lacked “an accounting
    basis.”193
    Cloud Jumper’s Internal Billing would not have been a problem in isolation.
    There is nothing inherently wrong with a private company adopting
    non-GAAP-compliant accounting measures for its unaudited financial statements.194
    The circumstances changed when Cloud Jumper shared financial submissions with
    NetApp that included—but did not call out—the Internal Billings and made a series
    of related misrepresentations.195
    Cloud Jumper acted recklessly when it endorsed representations that the
    Internal Billings represented real revenue, that Cloud Jumper’s financials were
    GAAP-compliant and reflected bona fide transactions, and that Cloud Jumper’s top
    190
    Picarello Tr. 28, 44-45.
    191
    JX 32; JX 33; JX 35.
    192
    Cinelli Tr. 483-84, 488-89, 493, 526-27; Helms Dep. 64, 67; Picarello Tr. 28, 61;
    VanFossen Dep. 215-16.
    193
    Cinelli Dep. 39.
    194
    See Hughes Tr. 581-82; Hughes Dep. 30-31, 52-53.
    195
    See JX 69; JX 78; JX 111; JX 114.
    34
    relationships were with third parties.196 It should have been obvious to Cloud Jumper
    that its financial statements were inflated and that its associated representations to
    NetApp were untrue.197 The Internal Billings constituted more than 40% of the
    Software Business’s revenue—the only business Cloud Jumper expected to continue
    after 2022.198 Yet Cloud Jumper officers consciously overlooked “specific warning
    signs” related to Internal Billing that signaled Cloud Jumper’s representations were
    false.199 It is not credible that Cloud Jumper simply forgot about the Internal Billing
    practice during merger negotiations.
    196
    See supra notes 101-06 and accompanying text.
    197
    See PR Diamonds, Inc. v. Chandler, 
    364 F.3d 671
    , 684 (6th Cir. 2004) (“[A]n inference
    of knowledge or recklessness may be drawn from allegations of accounting violations that
    are so simple, basic, and pervasive in nature, and so great in magnitude, that they should
    have been obvious to a defendant.”), abrogated in part on other grounds by Frank v. Dana
    Corp., 
    646 F.3d 954
    , 961 (6th Cir. 2011); see also In re Oxford Health Plans Inc. Secs.
    Litig., 
    51 F. Supp. 2d 290
    , 295 (S.D.N.Y. 1999) (noting that recklessness could be inferred
    from “[a]n egregious refusal to see the obvious, or to investigate the doubtful” (citation
    omitted)); Kinney v. Metro Glob. Media, Inc., 
    170 F. Supp. 2d 173
    , 180 (D.R.I. 2001)
    (“[T]he magnitude of reporting errors may lend weight to allegations of recklessness where
    defendants were in a position to detect the errors. . . . The more serious the error, the less
    believable are defendants [sic] protests that they were completely unaware of [the
    company’s] true financial status and the stronger is the inference that defendants must have
    known about the discrepancy.” (citation omitted)); In re MicroStrategy, Inc. Sec. Litig.,
    
    115 F. Supp. 2d 620
    , 636-37 (E.D. Va. 2000) (“[W]hile alleging a misapplication of
    [GAAP] standing alone is insufficient, such allegation when combined with a drastic
    overstatement of financial results can give rise to a strong inference of scienter.” (citation
    omitted)).
    198
    PTO ¶ 28; JX 55 at AA3, AA5; JX 30; Helms Dep. 62-63; see also Hickey Opening
    Rep. at Tbl.2.
    199
    Metro Commc’n, 854 A.3d at 147; see also Miller v. Johnson, 
    1980 WL 333066
    , at *3
    (Del. Super. 1980) (“The mere fact that a speaker did not intend to misrepresent may not
    be his defense if he is chargeable with the means to verify the accuracy.”); Arwood, 2022
    35
    Further, Cloud Jumper personnel had motives to conceal the Internal Billing
    during due diligence. Cloud Jumper was burning cash rapidly and its leadership was
    under growing pressure from Cinelli, who hoped to “squeeze” NetApp for a higher
    price.200 Some members of Cloud Jumper management faced the prospect of losing
    their jobs.201 Others, such as Helms, expected that a successful merger would bring
    a substantial payday and felt that Cloud Jumper needed to do “whatever it takes” to
    close a deal.202 These motives provide circumstantial evidence of scienter to commit
    fraud.
    203 WL 705841
    , at *22 (“It is often difficult to discern precisely what is, or was, in the mind
    of an actor accused of fraud, which is why our law allows the factfinder to rely upon
    circumstantial evidence when determining whether sufficient proof of scienter exists in a
    fraud case.”).
    200
    JX 72; see Cinelli Dep. 87-88.
    201
    E.g., JX 30; JX 413; JX 201.
    202
    JX 168; see JX 138; JX 230; JX 72; Helms Dep. 81-82; JX 71.
    203
    See Cobalt Operating, LLC v. James Crystal Enters., LLC, 
    2007 WL 214926
    , at *25
    (Del. Ch. July 20, 2007) (concluding that managers had a motive to perpetrate a fraudulent
    scheme “to make a sale more likely” because they “had been promised substantial bonuses
    if a sale occurred”), aff’d, 
    945 A.2d 594
     (Del. 2008) (TABLE); id. at *3 (finding that a
    defendant’s “participation in . . . fraud” was explained by the “simple fact” that she “wanted
    to keep her job”); id. at *14 (observing that the “scope of the alleged fraud was at its
    greatest during the time when Crystal had the strongest motive to inflate its cash flow [] to
    make sure a deal got done and to squeeze a higher price out of Cobalt”); see also Arwood,
    
    2022 WL 705841
    , at *22 (“[M]otive to achieve a higher price . . . may alone support . . .
    an inference of scienter.”).
    36
    3.     Intent to Induce Reliance
    “A misrepresentation induces a party’s manifestation of assent if it
    substantially contributes to his decision to manifest his assent.”204 Where a party
    bargains for written representations in a transaction agreement and a counterparty
    provides them, it is “reasonably inferable that the [counterparty] intended to induce
    reliance.”205
    The defendants do not contest this element.          Nor could they.      NetApp
    bargained for the representations and warranties in the Merger Agreement. NetApp
    also obtained so-called “pro-sandbagging” language in Section 8.3 of the Merger
    Agreement.206        Cloud Jumper personnel made or endorsed the challenged
    representations in support of closing the merger. On these facts, it is apparent that
    Cloud Jumper intended for NetApp to rely on the false and misleading descriptions
    of its financial health.
    4.     Justifiable Reliance
    NetApp must prove not only that Cloud Jumper intended for it to rely on the
    false statements, but also that it took (or refrained from taking) action in justifiable
    204
    Trascent Mgmt. Consulting, LLC v. Bouri, 
    2018 WL 4293359
    , at *17 (Del. Ch. 2018)
    (citations omitted).
    205
    Prairie Cap. III, L.P. v. Double E Hldg. Corp., 
    132 A.3d 35
    , 62 (Del. Ch. 2015).
    206
    Merger Agreement § 8.3(d)(ii).
    37
    reliance on the statements.207 “[J]ustifiable reliance requires that the representations
    relied upon involve matters which a reasonable person would consider important in
    determining his course of action in the transaction in question.”208 This element is
    “easily met” where “the false statements at issue are contained in a written
    agreement.”209
    The defendants suggest that NetApp’s reliance was unjustified because
    NetApp had broad access to information during due diligence.210 NetApp submitted
    “high priority” diligence requests about Cloud Jumper’s accounting policies on
    revenue recognition, and about transactions with partners and customers.211 The
    information NetApp received from Cloud Jumper, however, obscured the Internal
    Billings in Cloud Jumper’s historical financial statements and Management
    Projections.
    207
    See Craft v. Bariglio, 
    1984 WL 8207
    , at *8 (Del. Ch. Mar. 1, 1984). NetApp’s breach
    of contract claim does not require proof of justifiable reliance. NetApp was entitled to rely
    upon Cloud Jumper’s representations, which “serve an important risk allocation function.”
    Cobalt, 
    2007 WL 2142926
    , at *28.
    208
    Craft, 
    1984 WL 8207
    , at *8.
    209
    LVI Grp. Invs., LLC v. NCM Grp. Hldgs., LLC, 
    2018 WL 1559936
    , at *13 n.198 (Del.
    Ch. Mar. 28, 2018).
    210
    The defendants’ post-trial brief makes this argument concerning scienter and active
    concealment, but—to my mind—it is more relevant to reliance.
    211
    JX 150 at 3-4, 8; see Mitzenmacher Tr. 149-60.
    38
    NetApp relied on Cloud Jumper’s financial submissions when considering
    whether to pursue the deal, securing Investment Committee authorization to proceed
    with an LOI and Merger Agreement, and determining a purchase price.                        For
    example, it used Cloud Jumper’s historical financial statements to populate a
    spreadsheet analyzing “Consolidated P&L – Quarterly” and used the Management
    Projections to create a “3 Year Forecast.”212 The resulting analyses overstated
    Software Business revenue because the underlying data from Cloud Jumper included
    Internal Billings.213
    The parties agreed that Cloud Jumper would make certain financial
    representations in the Merger Agreement. They agreed to allocate risk regarding the
    accuracy of these representations to Cloud Jumper.214               And they agreed that
    NetApp’s diligence would not alter their bargained-for risk allocation.215 NetApp
    had no reason to investigate whether Cloud Jumper’s financial submissions recorded
    intracompany transactions that lacked economic substance.216 NetApp’s reliance
    was justified.
    212
    See JX 93.
    213
    See id.; JX 402.
    214
    Merger Agreement § 8.3(d)(ii).
    215
    Id.
    216
    Mitzenmacher Tr. 110-13, 154-55; see Cobalt, 
    2007 WL 2142926
    , at *28 (“By
    obtaining the representations it did, [the buyer] placed the risk that [the seller’s] financial
    statements were false and that [the seller] was operating in an illegal manner on [the
    39
    5.     Damages
    Damages is an element of both NetApp’s breach of contract and fraud claims.
    NetApp has the burden to prove its damages by a preponderance of the evidence.217
    It must first demonstrate with “reasonable certainty” that it was damaged by the
    challenged conduct.218
    The fact of NetApp’s damages is not in doubt. At trial, Mitzenmacher
    credibly testified that NetApp would “[a]bsolutely not” have closed the merger if it
    had been aware of Cloud Jumper’s falsities.219 NetApp reasonably believed that the
    Internal Billings represented true revenue since Cloud Jumper never indicated
    otherwise. It was surprised to learn post-closing that the Software Business was less
    profitable than described.220
    seller]. . . . Its need then, as a practical business matter, to independently verify those
    things was lessened.”); Tam v. Spitzer, 
    1995 WL 510043
    , at *9 (Del. Ch. Aug. 17, 1995)
    (observing that a buyer is entitled to rely on contractual representations and “is under no
    duty to investigate the accuracy of representations made by the seller concerning its
    profitability and operational affairs, even when there is an opportunity to do so”).
    217
    See, e.g., In re Mobilactive Media, LLC, 
    2013 WL 297950
    , at *24 (Del. Ch. Jan. 25,
    2013).
    218
    Siga Techs., Inc. v. PharmAthene, Inc. (SIGA II), 
    132 A.3d 1108
    , 1111 (Del. 2015); see
    also Tanner v. Exxon Corp., 
    1981 WL 191389
    , at *1 (Del. Super. July 23, 1981)
    (“Reasonable certainty is not equivalent to absolute certainty; rather, the requirement that
    plaintiff show defendant’s breach to be the cause of his injury with ‘reasonable certainty’
    merely means that the fact of damages must be taken out of the area of speculation.”
    (citation omitted)).
    219
    Mitzenmacher Tr. 367.
    220
    See id. at 187-92; Lye Dep. 226-27; JX 275.
    40
    That leaves the amount of NetApp’s damages, which I turn to next.
    C.     Remedy
    Under Delaware law, the standard remedy for breach of contract “is based
    upon the reasonable expectations of the parties ex ante.”221          Similarly, “[t]he
    recipient of a fraudulent misrepresentation is entitled to recover as damages . . . the
    pecuniary loss to him of which the misrepresentation is a legal cause.”222 Such
    expectation—or benefit-of-the-bargain—damages are measured by the amount of
    money that would put the plaintiff in the position it would have held if the
    defendant’s representations were true.223         A less common approach is the
    out-of-pocket measure, which is “designed to restore the plaintiff to his financial
    position before the transaction occurred.”224 A plaintiff may elect to proceed on
    221
    SIGA II, 132 A.3d at 1130 (quoting Duncan v. Theratx, Inc., 
    775 A.2d 1019
    , 1022 (Del.
    2001)).
    222
    Restatement (Second) of Torts § 549(1); cf. Envo, Inc. v. Walters, 
    2009 WL 5173807
    ,
    at *7 n.37 (Del. Ch. Dec. 30, 2009) (“Delaware courts have cited the Restatement (Second)
    of Torts [§] 549 . . . with approval.”), aff’d, 
    2013 WL 1283533
     (Del. Mar. 28, 2013)
    (TABLE).
    223
    SIGA II, 
    132 A.3d at 1130
     (quoting Duncan, 
    775 A.2d at 1022
    ); Stephenson, 
    462 A.2d at 1076
     (explaining that awarding benefit-of-the-bargain damages “put[s] the plaintiff in
    the same financial position that [the plaintiff] would have been in if the defendant’s
    representations had been true”); see also Restatement (Second) of Torts § 549, at
    Illustrations 4-5; Restatement (Second) of Contracts § 347, cmt. a (1981) (“Contract
    damages are ordinarily based on the injured party’s expectation interest and are intended
    to give him the benefit of his bargain by awarding him a sum of money that will . . . put
    him in as good a position as he would have been in had the contract been performed.”).
    224
    Stephenson, 
    462 A.2d at 1076
    .
    41
    either theory.225 Damages are measured from the plaintiff’s perspective at the time
    of the breach.226
    1.    The Parties’ Legal Arguments on Damages
    Despite agreeing that damages for breach of contract and fraud are typically
    awarded using the benefit-of-the-bargain measure, the parties have diverging views
    on how such damages are calculated.             According to the defendants, a proper
    benefit-of-the-bargain analysis should measure the difference between the “as-
    represented” value of Cloud Jumper (the $35 million purchase price) and the
    “actual” value of Cloud Jumper (if its revenues were accurately reported).227
    NetApp, for its part, insists that the defendants’ approach to expectation damages is
    wrong because “analyses that compare actual value to what NetApp paid measure
    out-of-pocket damages.”228 From NetApp’s perspective, its expectation damages
    should address the future cash flows it planned to generate from the acquisition,
    irrespective of the purchase price.229
    225
    
    Id.
    226
    See id.; Strassburger v. Earley, 
    752 A.2d 557
    , 579 (Del. Ch. 2000) (noting that
    “compensatory damages are determined at the time of the transaction”).
    227
    Defs.’ Post-trial Br. 44 (citing Zayo Grp., LLC v. Latisys Hldgs., LLC, 
    2018 WL 6177174
    , at *16 (Del. Ch. Nov. 26, 2018)); id. at 48.
    228
    Pl.’s Post-trial Reply Br. 35 (citing Stephenson, 
    462 A.2d at 1076
    ) (emphasis removed).
    229
    See id. at 25-26, 29-32.
    42
    To resolve the parties’ conceptual dispute, I look to precedent. The general
    descriptions of benefit-of-the-bargain and out-of-pocket damages found in our law
    are of limited utility. Stephenson v. Capano Development, Inc. counsels that benefit-
    of-the-bargain damages “are equal to ‘the difference between the actual and the
    represented values of the object of the transaction.’”230 Out-of-pocket damages, by
    contrast, are “equal to ‘the difference between what [the plaintiff] paid and the actual
    value of the item’ that the plaintiff received.”231 This seems clear—unless the
    purchase price is the represented value used to calculate expectation damages, in
    which case the two measures collapse into one another.232
    Precedent in the M&A context provides more illuminating guidance. In that
    setting, Delaware courts routinely use the purchase price as the starting point for
    benefit-of-the-bargain damages calculations. This makes sense. The purchase price
    for a company is often the result of arms’-length negotiations between sophisticated
    230
    LCT Cap., LLC v. NGL Energy P’rs LP, 
    249 A.3d 77
    , 91 (Del. 2021) (quoting
    Stephenson, 
    462 A.2d at 1076
    ).
    231
    
    Id.
    232
    A basic hypothetical highlights the problem. Assume a plaintiff buyer purchased an
    item from the defendant seller that had a represented value of $1,000,000, though the item
    was actually worth $700,000. The buyer paid $900,000 for the item. The plaintiff’s out-
    of-pocket damages would be $200,000—the difference between what she paid ($900,000)
    and received ($700,000). Her benefit-of-the-bargain damages, by contrast, would be
    $300,000—the difference between the misrepresented value ($1,000,000) and the actual
    value received ($700,000). If the represented value were the $900,000 purchase price,
    damages would be the same under either approach.
    43
    parties and reflects the potential risks and rewards of execution.233 The price might
    have been established with a market approach using a multiple, or an income
    approach using a discount rate.234 Damages, then, may be calculated using the
    corresponding method to account for any diminution in value attributable to the
    misrepresentation.235
    In Tam v. Spitzer, for example, the defendant seller knew that its largest
    customer would soon be terminating its business relationship with the seller but
    withheld this information from the buyer.236 Then-Vice Chancellor Jacobs found
    that the transaction was induced by false misrepresentations amounting to common
    233
    See Maverick Therapeutics, Inc. v. Harpoon Therapeutics, Inc. (Maverick II), 
    2021 WL 1592473
    , at *12 (Del. Ch. Apr. 23, 2021) (“The [purchase] price . . . necessarily factors in
    the low probability of ultimate success as well as the potentially large pay-off upon such
    success.”); see also Sharma v. Skaarup Ship Mgmt. Corp., 
    916 F.2d 820
    , 825 (2d Cir. 1990)
    (“[T]he value of the item at the time of the breach . . . actually takes expected lost future
    profits into account.”).
    234
    See, e.g., Tam, 
    1995 WL 510043
    , at *10, *12 (calculating expectation damages based
    on values at the time of the transaction, which incorporated future expectations); Cobalt,
    
    2007 WL 2142926
    , at *30 (awarding damages using a valuation based on expectations of
    future cash flow).
    235
    See WaveDivision Hldgs., LLC v. Millennium Dig. Media Sys., L.L.C., 
    2010 WL 3706624
    , at *22-23 (Del. Ch. Sept. 17, 2010) (rejecting a DCF method and calculating
    expectation damages using a multiple of EBITDA analysis where it was the approach on
    which the buyer based its expectations); cf. Zayo, 
    2018 WL 6177174
    , at *17 (criticizing
    the use of “an EBITDA multiple as the most accurate and comprehensive metric for valuing
    damages” where there was “no evidence” that the purchase price was based on a multiple
    of EBITDA).
    236
    
    1995 WL 510043
    , at *5.
    44
    law fraud. Damages were awarded under the benefit-of-the-bargain theory.237 The
    court used a DCF method to value the business at the time of the sale less revenue
    and expenses attributable to the lost customer’s business. The resulting actual value
    was subtracted from the purchase price, which reflected the buyer’s expectation of
    future revenue from the customer.           The buyer’s damages were equal to the
    difference.238
    In Cobalt Operating, LLC v. James Crystal Enterprises, LLC, the defendant
    seller was found to have fraudulently inflated the target business’s cash flows to
    justify a $70 million purchase price, which had been set using a cash flow
    multiple.239 The seller’s actions were contrary to its representations about the
    legitimacy of its financial statements, among other representations. Then-Vice
    Chancellor Strine described the “traditional method” of computing damages as that
    reflecting the “reasonable expectations of the parties”; that is, “the amount of money
    that would put the non-breaching party in the same position that the party would
    237
    Id. at *12.
    238
    In Tam, the purchase price was $103,500. Id. at *4. The same DCF method and
    valuation date used to arrive at the purchase price was applied, less revenues and expenses
    attributable to the lost customer. Id. at *12. This calculation yielded an adjusted value for
    the business of $58,210. Id. Because the plaintiff “overpaid” by $45,290 ($103,500 minus
    $58,210), the purchase price was “adjusted downward” to $58,210. Id. The plaintiff had
    already paid $59,875.37 to the defendant. Damages were the difference of $1,665.37. Id.
    239
    
    2007 WL 2142926
    , at *29-30 (awarding damages using a valuation based on
    expectations of future cash flows).
    45
    have been in had the breach never occurred.”240 He determined that the business’s
    actual value was $59 million, resulting in $11 million of damages when compared
    to the $70 million purchase price.241
    Most recently, in Maverick Therapeutics, Inc. v. Harpoon Therapeutics, Inc.,
    Vice Chancellor Glasscock found that a seller committed “fraud in the sale of a spin-
    off designed to develop anti-cancer technology.”242                 The fraud involved
    misrepresentations about non-compete protections “the new entity would enjoy from
    competing with its parent and [the] seller,” since the seller had formed a competing
    product.243 The court assessed the plaintiff’s damages by comparing two values:
    “what [the plaintiff] thought it had purchased, and what it actually got as a result of
    [the seller’s] fraud.”244 The former value was the “negotiated value” of the plaintiff’s
    investment.245 The latter value reflected losses the plaintiff would experience from
    entering a market in competition with the seller. The plaintiff’s damages were the
    240
    
    Id.
     at *29 (citing Duncan, 
    775 A.2d at 1022
    ).
    241
    Id. at *30. The award was payable by canceling the defendant’s $2 million equity
    interest in the plaintiff and a $5 million promissory note. Damages of $4 million were
    awarded. Id.
    242
    
    2021 WL 1592473
    , at *1.
    243
    
    Id.
    244
    
    Id.
    245
    Id. at *12-13 (“The parties, in an arm’s-length transaction between sophisticated entities
    represented by counsel, had no trouble valuing Millennium’s investment as of 2017 with
    the broad non-compete Millennium expected.”).
    46
    difference between the two, “discounted by what a buyer would pay to avoid the
    possibility of such competition.”246
    Delaware courts have also awarded expectation damages measured by lost
    profits rather than lost business value.247          In PharmAthene, Inc. v. SIGA
    Technologies, Inc., the defendant breached a contractual obligation to negotiate the
    final terms of a license agreement for an early-stage drug in the event that a proposed
    merger failed.248 After terminating the merger agreement and learning that the drug
    could be more profitable than anticipated, the defendant declined to negotiate the
    license and proposed terms different from those in the parties’ initial term sheet.
    Vice Chancellor Parsons found it reasonably certain that the plaintiff lost profits due
    to the defendant’s bad faith conduct.249 He awarded $133 million in damages, based
    on earnings the plaintiff could have expected from drug sales had the defendant
    executed the license agreement.250 The Delaware Supreme Court affirmed.
    246
    Id. at *13.
    247
    See PharmAthene, Inc. v. SIGA Techs., Inc., 
    2014 WL 3974167
     (Del. Ch. Aug. 8, 2014)
    (“One measure of expectation damages is a party’s lost profits.”), aff’d, SIGA II, 
    132 A.3d 1108
    .
    248
    SIGA II, 
    132 A.3d at 1117-18
    .
    249
    Id. at 1131.
    250
    The term sheet established a revenue-based royalty payment, set out a profit split, and
    addressed other amounts to be paid if milestones were met. Id.
    47
    Although “[d]iminution of value, a backward-looking measure of damages, is
    fundamentally different from lost profits, a forward-looking measure,”251 both
    promote the same end.          The objective is to restore the injured party to the
    economically equivalent position it would have held absent the injury.252 Benefit-
    of-the-bargain damages using either approach can remedy future harm to a
    business.253
    Here, Cloud Jumper led NetApp to believe that the Software Business was
    more robust than it was. Cloud Jumper represented that it had $13,461,450 of total
    revenue for 2019, with the Software Business responsible for $2,498,164.254 The
    Internal Billings accounted for $1,087,366 of the latter figure, representing 8% of
    251
    Powers v. Stanley Black & Decker, Inc., 
    137 F. Supp. 3d 358
    , 386 (S.D.N.Y. 2015)
    (citing Tractebel Energy Mktg., Inc. v. AEP Power Mktg., Inc., 
    487 F.3d 89
    , 109 (2d Cir.
    2007)).
    252
    See, e.g., 
    id.
     (“[W]here the seller makes misrepresentations about the business he is
    selling, the natural and probable result is that the business is actually worth less than the
    buyer paid, and diminution of value damages therefore compensate the buyer for ‘the value
    of the promised performance.’” (quoting Schonfeld v. Hilliard, 
    218 F.3d 164
    , 176 (2d Cir.
    2000)); WaveDivision, 
    2010 WL 3706624
    , at *22 (observing that “[b]ecause a buyer often
    intends to operate a business in a way that will change its cash flows, its expectancy
    damages are the profits it expected to make, if it can prove them with reasonable
    certainty”).
    253
    See Cobalt, 
    2007 WL 2142926
    , at *27 (describing the plaintiff’s harm from materially
    misleading representations about the accuracy of financial statements concerning annual
    cash flow as affecting earnings on a going-forward basis).
    254
    Kleinrichert Revised Opening Rep. 24.
    48
    Cloud Jumper’s revenues or 43.5% of its Software Business revenues.255 This did
    not amount to a one-time loss for NetApp, but would continue to affect future cash
    flows. In these circumstances, dollar-for-dollar damages would not make NetApp
    whole.256
    With that framing, I consider the parties’ respective damages estimates.
    2.     The Experts’ Damages Calculations
    NetApp seeks to recover damages based on the stream of future cash flows it
    expected to generate by acquiring Cloud Jumper. NetApp estimates that Cloud
    Jumper’s fraud and breaches of contract caused it to lose future cash flows worth
    $37.7 million on a present value basis.257 The defendants reject NetApp’s approach
    and focus on the diminution in Cloud Jumper’s value attributable to the
    255
    The overstatement as a percentage of Cloud Jumper’s total annual revenue was 8%
    percent in 2019 and 4% in 2018. See Hughes Tr. 587-88.
    256
    Cf. Universal Enters. Grp. LP v. Duncan Petroleum Corp., 
    2013 WL 3353743
    , at *1,
    *20 (Del. Ch. July 1, 2013) (observing that environmental issues contrary to
    representations in an asset purchase agreement did “not appear to have translated into
    unsafe operations or environmental spills” and awarding dollar-for-dollar damages equal
    to the costs the plaintiff incurred in remediating the environmental conditions of subject
    properties); Zayo, 
    2018 WL 6177174
    , at *16 (discussing that the loss of short-term
    customer relationships, which purportedly breached a stock purchase agreement, did not
    diminish the business’s value in an amount greater than the out-of-pocket loss represented
    by the lost contract revenue); see also Ass’n of Int’l Certified Pro. Accts., Forensic &
    Valuation Services Practice Aid: Mergers & Acquisitions Disputes 58 (2020) (updated Jan.
    1, 2020) (“Claims that result in dollar-for-dollar damages are typically those that have a
    one-time effect on the target and that do not impact the target financial condition in future
    periods (in other words, will not affect future cash flows).”).
    257
    See Pl.’s Post-trial Opening Br. 42.
    49
    misrepresented software revenue, which supports a maximum recovery of
    approximately $4.6 million.258 Each position is supported by an expert opinion.
    a.     Hickey’s Analysis
    NetApp’s damages estimate relies upon the expert opinion of George S.
    Hickey.259       Hickey performed a single analysis.260      He calculated NetApp’s
    expectations for Cloud Jumper as a unit of NetApp using Cloud Jumper’s projected
    cash flow plus synergistic cash flow. From that number, he subtracted the value of
    future cash flows that NetApp actually received, adjusting for the Internal Billings.
    He did not assess the value of Cloud Jumper on a standalone basis.261
    Hickey employed a three-step approach using a DCF methodology.262 First,
    he replicated NetApp’s valuation analysis at the time of the deal using the Combined
    Projections. NetApp’s analysis valued Cloud Jumper using a DCF model based on
    expected future cash flows for 2020 to 2024 derived from Cloud Jumper’s
    258
    See Defs.’ Post-trial Br. 57.
    259
    Hickey is a senior vice president at Yilmaz Advisory with 25 years of experience in
    economic consulting focusing on M&A disputes and other transactions. He has served as
    a consulting expert in matters before the Court of Chancery about a dozen times. See
    Hickey Opening Rep. ¶¶ 1-2.
    260
    See Expert Rebuttal Report of Gary Kleinrichert (Dkt. 85; JX 333) (“Kleinrichert
    Rebuttal Rep.”) 3. Hickey also provided a rebuttal opinion critiquing the defendants’
    expert’s analyses. Expert Rebuttal Report of George S. Hickey (Dkt. 85; JX 332) (“Hickey
    Rebuttal Rep.”).
    261
    Hickey Tr. 730-31.
    262
    Id. at 681-82.
    50
    Management Projections, as revised by NetApp. Hickey applied a terminal value
    estimate assuming those cash flows would grow between 2.5% and 3.5% in
    perpetuity and a weighted average cost of capital (WACC) range of 12.5% to
    17.5%.263 Doing so resulted in future cash flows worth between $65.2 million and
    $123.1 million on a present value basis, with a midpoint of $86.2 million.264
    Second, Hickey adjusted NetApp’s Combined Projections to address Internal
    Billings. Hickey reduced NetApp’s estimate of revenue synergies that could be
    realized from the acquisition, which he calculated to be inflated by approximately
    42% from Internal Billing.265 Removing the Internal Billings resulted in future cash
    flows worth between $36.4 million and $69.8 million on a present value basis, with
    a midpoint of $48.5 million.266
    Finally, Hickey calculated damages equal to the difference between these
    estimates (or between $28.8 million and $53.3 million) on a present value basis. The
    midpoint is $37.7 million.267 NetApp seeks that amount as damages.
    263
    Hickey Opening Rep. ¶ 47 (citing JX 93, “DCF” tab).
    264
    Id. ¶¶ 48, 53. $86.2 million represents the midpoint of WACC and perpetuity growth
    rate assumptions—i.e., a 3% growth rate and a 15% WACC. See id. at Ex. 1 (perpetuity
    growth rate and WACC table). The same applies for the midpoint analysis discussed infra
    at notes 266-67 and accompanying text.
    265
    Id. ¶ 51, Tbl.9.
    266
    Id. ¶ 54.
    267
    Id. ¶ 55.
    51
    b.     Kleinrichert’s Analyses
    The defendants’ expert, Gary Kleinrichert, compared the $35 million purchase
    price to what he determined to be Cloud Jumper’s fair market value as of the
    April 28, 2020 closing.268 Kleinrichert arrived at his opinion of fair market value for
    Cloud Jumper using several methods: an income approach, a market approach, an
    adjusted “football field” analysis, and by assessing implied deal multiples of
    revenue.269
    Kleinrichert’s income approach used NetApp’s standalone DCF model for
    Cloud Jumper, adjusted to account for the Internal Billings in Cloud Jumper’s
    income statement.270 Kleinrichert first lowered projected software revenue based on
    an estimate of annual Internal Billings. He then adjusted the gross margins for Cloud
    Jumper’s Legacy and Software Businesses after removing the Internal Billings. He
    applied a 15% WACC and a 3% perpetual growth rate, which were inputs adopted
    268
    Kleinrichert is a Certified Public Accountant, Certified Valuation Analyst, accredited
    in business valuation, and certified in financial forensics. He is a senior managing director
    in the Forensic and Litigation practice of FTI Consulting, Inc. and has over 35 years of
    experience as an auditor and consultant in accounting, auditing, investigative, litigation,
    and valuation matters. See Revised Kleinrichert Opening Rep. at 3.
    269
    Revised Kleinrichert Opening Rep. 4-8.
    270
    The income approach determines a value indication “based on the assumption that the
    value of an ownership interest is equal to the sum of the present values of the expected
    future benefits of owning that interest.” Id. at 26 (quoting James R. Hitchner, Financial
    Valuation: Applications and Models 281 (4th ed. 2017)).
    52
    by NetApp when developing its own DCF analysis.271 Kleinrichert also corrected
    an error in NetApp’s terminal value calculation based on its 2024 undiscounted free
    cash flow estimate.272 Kleinrichert arrived at an indication of value for Cloud
    Jumper of approximately $48.6 million using the income method.
    Kleinrichert’s market approach valued Cloud Jumper based on guideline
    public companies and guideline transactions methods.273 He identified several
    public companies and transactions in the MSP and the VDI industries, from which
    he calculated median multiples of enterprise value to revenue (EV/revenue).
    Kleinrichert determined value through these methods by applying the median
    revenue multiple he calculated for each industry to Cloud Jumper’s respective
    revenue streams. He reached an indication of value of approximately $30.4 million
    using the guideline public companies method and approximately $35.0 million using
    the guideline transactions method.274
    271
    See id. at 27-32.
    272
    Kleinrichert Revised Opening Rep. at Sched. 3. The free cash flow number NetApp
    used to calculate terminal value had already been discounted before NetApp again
    discounted it to present value. See Hickey Tr. 737-38 (observing that NetApp should have
    used $22.3 million for 2024 free cash flow rather than the $11.9 million it inputted).
    273
    The market approach is “a general way of determining a value indication of a business,
    business ownership interest, security, or intangible asset by using one or more methods that
    compare the subject to similar businesses, business ownership interests, securities, or
    intangible assets that have been sold.” Kleinrichert Revised Opening Rep. 27 (quoting
    NACVA, International Glossary of Business Valuation Terms (June 8, 2001),
    http://www.nacva.com/glossary (defining Market (Market-Based) Approach)).
    274
    Id. at 5, 7-8.
    53
    Kleinrichert weighted his conclusion of value toward the market approach
    over the income approach.275 He calculated the difference between the purchase
    price and a fair market value of Cloud Jumper ranging from $30.4 million to $35.0
    million. He concluded that NetApp’s damages are $0 to $4.6 million.276
    Kleinrichert prepared two other analyses that did not factor into his damages
    estimate. First, he prepared an adjusted version of the “football field” chart that the
    NetApp deal team presented to secure Investment Committee approval for an LOI.277
    NetApp’s original chart included the four valuation methodologies NetApp had
    considered: a standalone DCF using the Standalone Projections, a combined DCF
    (including synergistic value) using the Combined Projections,278 a guideline
    transactions analysis, and a guideline public companies analysis. Kleinrichert’s
    revised football field included the three indications of value he calculated plus an
    adjusted DCF that considered estimated synergies and the effect of Internal
    Billing.279 Based on this chart, Kleinrichert opined that the $35 million purchase
    275
    Id. at 38.
    276
    Kleinrichert believed that NetApp’s own “football field” chart and an implied multiple
    analysis, among other things, supported the low end of this range as a reasonable estimate
    of damages. Id. at 8; see also Expert Report of Gary Kleinrichert (Dkt. 85; JX 330)
    (“Kleinrichert Opening Rep.”) at Sched. 1.0.
    277
    See JX 129 at 19.
    278
    See infra Section II.C.2.a.i. (discussing synergistic value).
    279
    See Kleinrichert Revised Opening Rep. 39-41, Updated Sched. 7.0. Kleinrichert’s
    combined DCF analysis left NetApp’s other assumptions unchanged. Id. at 40-41.
    54
    price remains within or below the range of valuation methods considered by NetApp
    after adjusting for Internal Billing.280
    Finally, Kleinrichert analyzed the implied deal multiples from the Cloud
    Jumper acquisition as another indication of value. Based on the $35 million
    purchase price and the 2019 revenues Cloud Jumper disclosed to NetApp, NetApp
    purchased Cloud Jumper at a 2.6x EV/revenue multiple. Kleinrichert’s concluded
    that this blended multiple falls within an acceptable range of comparable
    multiples.281 When Cloud Jumper’s 2019 revenue is adjusted for Internal Billing,
    the multiple increases to 2.8x revenue, which is within the range of multiples
    considered by NetApp in its contemporaneous valuation analysis.282 Damages based
    on an application of the original implied deal multiple to the 2019 Internal Billings
    would be $2.83 million.283
    3.   Assessment of the Parties’ Damages Estimates
    The record establishes that NetApp was damaged by relying on Cloud
    Jumper’s representations about the accuracy of its financial statements.284 NetApp
    280
    Id. at 41.
    281
    Id. at 42-43; see Kleinrichert Opening Rep. at Scheds. 4.0 & 5.0.
    282
    Kleinrichert Revised Opening Rep. 43.
    283
    Id. This figure is calculated by applying the 2.6x implied multiple to the 2019 Internal
    Billing revenue of $1,087,366 for a difference of $2,827,169. Id. at 44; see Kleinrichert
    Opening Rep. at Sched. 6.1.
    284
    See supra Section II.B.5.
    55
    strategically acquired Cloud Jumper to grow in the VDI space, but Cloud Jumper’s
    Software Business revenues were meaningfully lower than NetApp was led to
    believe. Had NetApp known about the Internal Billing, it would not have purchased
    Cloud Jumper—at least not for $35 million.285
    My task, then, is to determine the appropriate remedy. As discussed below, I
    decline to adopt NetApp’s damages estimate. Hickey’s analysis is imprudent, and
    his damages conclusion would deliver a windfall to NetApp.
    Instead, I assess NetApp’s damages based upon the diminution in value it
    experienced because of Cloud Jumper’s misrepresentations. Kleinrichert’s analysis
    is not faultless, but his guideline public companies method yields a credible estimate
    of lost business value.286
    a.     NetApp’s Estimate
    NetApp’s approach is facially appealing. It considers NetApp’s expectations
    for how Cloud Jumper would perform as a unit of NetApp, including revenue
    synergies. Yet I cannot adopt it for two reasons. First, the record lacks any tangible
    facts to support a reasonable inference that NetApp would have achieved the
    285
    See Lye Dep. 227; Mitzenmacher Tr. 188-89, 367.
    286
    Kleinrichert’s relatively superior experience in calculating benefit-of-the-bargain
    damages gives added credibility to his approach. See supra notes 259, 268; Zayo, 
    2018 WL 6177174
    , at *15 n.196 (describing Kleinrichert’s “significant experience in benefit-of-
    the-bargain damages and business valuation”).
    56
    theoretical synergies it projected. Second, NetApp’s estimate is not limited to the
    harm proximately caused by Cloud Jumper’s fraud and breaches of contract.
    i.       Speculative Synergies
    NetApp’s estimate includes post-closing synergistic cash flows it hoped to
    attain by increasing sales of Cloud Jumper software using NetApp’s larger sales
    force and by leveraging Cloud Jumper’s VDI product with complementary NetApp
    products. In NetApp’s view, it is entitled to recover the value of these projected
    synergies, adjusted for the effect of Internal Billing on the combined entity.
    “Synergy is the potential additional value from combining two firms.”287
    Synergies may arise from multiple potential sources, such as a reduction of average
    costs or revenue upside from a more productive use of assets.288 The potential to
    create synergistic value between two previously separate businesses is often a
    driving factor in business combinations.289 Prospective corporate synergies involve
    287
    Aswath Damondaran, Investment Valuation: Tools and Techniques for Determining the
    Value of Any Asset 707 (3d ed. 2012); Merion Cap. LP v. BMC Software, Inc., 
    2015 WL 6164771
    , at *14 (Del. Ch. Oct. 21, 2015) (describing synergies as “value arising solely
    from the deal”); Mitzenmacher Dep. 51.
    288
    See, e.g., J. Myles Shaver, A Paradox of Synergy: Contagion and Capacity Effects in
    Mergers and Acquisitions, 31 Acad. Mgmt. Rev. 962, 962-63 (2006).
    289
    See WaveDivision, 
    2010 WL 3706624
    , at *23 n.151; see also Cinerama, Inc. v.
    Technicolor, Inc., 
    663 A.2d 1134
    , 1143 (Del. Ch. 1994) (“The components of value in an
    acquisition might be considered to be two: the going concern value of the firm as currently
    organized and managed and the ‘synergistic value’ to be created by the changes that the
    bidder contemplates (e.g., new management, cost efficiencies, etc.).”), aff’d, 
    663 A.2d 1156
     (Del. 1995).
    57
    predictions about the unpredictable process of integrating a new business into an
    existing one. These unknowns may result in an overvaluation of synergies, which
    can take longer to capture than anticipated—if they are captured at all.290
    Here, there is no evidentiary basis from which I can make a “responsible
    estimate” of lost synergistic cash flows.291 Mathematical certainty is not required
    “where a wrong has been proven and injury established.”292 Nonetheless, the court
    cannot award damages based on “speculation or conjecture.”293 An award of
    expectation damages “presupposes that the plaintiff can prove damages with
    reasonable certainty.”294
    290
    See generally Mark L. Sirower & Jeffery M. Weirens, The Synergy Solution: How
    Companies Win the Merger & Acquisitions Game (2022) (analyzing mergers over a 24
    year period and observing that most acquirers realized negative average returns and failed
    to achieve expected synergies); Scott A. Christofferson et al., Where Mergers Go Wrong,
    McKinsey Q. (May 1, 2004) (available at https://www.mckinsey.com/capabilities/strategy-
    and-corporate-finance/our-insights/where-mergers-go-wrong) (observing that 70% of
    mergers fall short of achieving targets for revenue synergies).
    291
    Beard Rsch., Inc. v. Kates, 
    8 A.3d 573
    , 613 (Del. Ch. 2010), aff’d, 
    11 A.3d 749
     (Del.
    2010).
    292
    
    Id.
     (quoting Del. Express Shuttle, Inc. v. Older, 
    2002 WL 31458243
    , at *15 (Del. Ch.
    Oct. 23, 2002)); see also SIGA II, 
    132 A.3d at 1111
     (“The amount of damages can be an
    estimate.”).
    293
    Acierno v. Goldstein, 
    2005 WL 3111993
    , at *6 (Del. Ch. Nov. 16, 2005); see also Great
    Hill Equity P’rs IV, LP v. SIG Growth Equity Fund I, LLLP, 
    2020 WL 948513
    , at *23 (Del.
    Ch. Feb. 27, 2020) (awarding no damages related to misrepresentations where the plaintiffs
    “could have, but did not, provide a non-speculative way to quantify damages”); Frontier
    Oil v. Holly Corp., 
    2005 WL 1039027
    , at *39 (Del. Ch. Apr. 29, 2005) (“[A]bsolute
    precision is not required but the proof may not be speculative either.”).
    294
    SIGA Techs., Inc. v. PharmAthene, Inc., 
    67 A.3d 330
    , 351 n.99 (Del. 2013) (citing
    Callahan v. Rafail, 
    2001 WL 283012
    , at *1 (Del. Super. Mar. 16, 2001)); Callahan, 2001
    58
    NetApp maintains that the Combined Projections provide adequate support
    for its expectation damages.295 In preparing the Combined Projections, NetApp
    identified two types of synergies and created forecasts for each.296 NetApp avers
    that these forecasts are the best evidence of the value it expected to receive from
    Cloud Jumper—including synergistic value.297
    I disagree. To assess whether NetApp reasonably expected to realize the
    synergies it layered on top of the Standalone Projections would be a theoretical
    exercise.298 NetApp’s predictions were aspirational. Its financial due diligence
    report noted that NetApp’s revenue team did not evaluate NetApp’s valuation model,
    including whether “synergies made any sense.”299 The report also remarked that
    Cloud Jumper would need “heavy support from [the] NetApp cloud sales team to
    WL 283012, at *1 (“It is well-settled law that a recovery for lost profits will be allowed
    only if their loss is capable of being proved, with a reasonable degree of certainty. No
    recovery can be had for loss of profits which are determined to be uncertain, contingent,
    conjectural, or speculative.” (citation omitted)).
    295
    Pl.’s Post-trial Opening Br. 46.
    296
    See Hickey Tr. 689-94; JX 129 at 39.
    297
    See Mitzenmacher Tr. 124-25; Hickey Tr. 694.
    298
    See Mitzenmacher Tr. 197-99; see also JX 78.
    299
    JX 259 at 9.
    59
    drive growth and adoption in order to achieve the aggressive [s]ynergies modeled in
    the financial DCF valuation.”300
    Hickey’s analysis does little to ground NetApp’s estimate. Hickey did not test
    NetApp’s synergy calculations or opine on their reasonableness, but wholesale
    adopted NetApp’s assumptions.301 Using an erroneous model that would have raised
    NetApp’s damages calculation by nearly $20 million if corrected further reveals the
    imprudence of his approach.302
    NetApp attempts to overcome the conjectural nature of this analysis by
    appealing to the “wrongdoer rule,” which provides that uncertainty in a damages
    300
    See id. at 9, 12, 45. The due diligence report also notes that NetApp’s revenue team did
    not perform diligence on the NetApp model or whether the synergies were supportable. Id.
    at 9.
    301
    In fact, events post-closing suggest that NetApp’s predictions were unreasonable. See
    infra notes 316-23 and accompanying text.
    302
    The NetApp model Hickey used included a reference error that understated the terminal
    value. See supra note 272. Although Hickey discovered the error after the exchange of
    opening expert reports and identified the issue in his rebuttal report, he—unlike
    Kleinrichert—declined to revise his model to correct it. Changing the cell reference would
    have increased the calculation of Cloud Jumper’s total enterprise value to approximately
    $133 million, or $75 million adjusting for Internal Billing. That would mean Hickey’s
    estimated damages would rise to $58 million. See Hickey Tr. 705-07.
    Hickey testified that he made a principled decision not to incorporate the corrected
    values into his analysis. He reasoned that NetApp’s contemporaneous expectations relied
    on the flawed data and he believed that by not correcting for the error, he would put forth
    a “more conservative” measurement. Id. at 706-07. Regardless, NetApp’s Combined
    Projections were wrong and so is Hickey’s analysis.
    60
    estimate should be construed against the breaching party.303 Resolving uncertainty
    against Cloud Jumper does not relieve NetApp of its burden to present expectation
    damages that are not speculative.304 Moreover, the pervasive uncertainty in the
    Combined Projections is not a result of Cloud Jumper’s misrepresentations;305 it is
    due to NetApp making optimistic predictions about the unknown. Whether NetApp
    would deliver on its prognostications depended on how NetApp operated the
    combined entity—a matter squarely in NetApp’s hands.
    303
    SIGA II, 132 A.3d at 1131 n.132 (“Courts in Delaware and other jurisdictions have
    frequently applied the ‘wrongdoer rule’ where the wrongdoer’s breach contributed to
    uncertainty over the amount of damages.”); Am. Gen. Corp. v. Cont’l Airlines Corp., 
    662 A.2d 1
    , 10 (Del. Ch. 1992) (explaining that if a defendant’s wrongful conduct contributed
    to uncertainty in the calculation of damages, “the perils of such uncertainty should be ‘laid
    at the defendant’s door’” (quoting Madison Fund, Inc. v. Charter Co., 
    427 F. Supp. 2d 597
    ,
    608 (S.D.N.Y. 1977))); Maverick II, 
    2021 WL 1592473
    , at *10 (“A moment’s reflection
    demonstrates that the perpetrator of an intentional tort should not get the benefit of
    uncertainty in the quantum of harm he has caused.”).
    304
    See Duncan, 
    775 A.2d at
    1023-24 n.12 (observing that the risks of uncertainty
    surrounding future events that are “impossible to know” should not be resolved against the
    defendant); Madison Fund, 427 F. Supp. 2d at 608 (“This Court simply cannot credit
    plaintiff with market prescience. And, as the Supreme Court has observed, ‘even where
    the defendant by his own wrong has prevented a more precise computation, the (factfinder)
    may not render a verdict (with respect to damages) based on speculation or guess-work.’”
    (quoting Bigelow v. RKO Radio Pictures, 
    327 U.S. 251
    , 264 (1946))); Del. Express Shuttle,
    
    2002 WL 31458243
    , at *15 (emphasizing that “[s]peculation is an insufficient basis” for a
    damages award).
    305
    Compare SIGA II, 
    132 A.3d at 1111
     (“When a party breaches a contract, that party often
    creates a course of events that is different from those that would have transpired absent the
    breach. The breaching party cannot avoid responsibility for making the other party whole
    simply by arguing that expectation damages based on lost profits are speculative because
    they come from an uncertain world created by the wrongdoer.”).
    61
    Finally, NetApp contends that Delaware courts have awarded damages based
    on estimated profits the buyer could have gained absent the seller’s breach.306 But
    the case NetApp mainly relies on highlights the fault in NetApp’s position. In
    WaveDivision Holdings, LLC v. Millennium Digital Media Systems, L.L.C., a jilted
    buyer was awarded damages equivalent to the value it expected to receive by
    purchasing certain cable systems less any costs avoided by not having to perform.307
    The court’s EBITDA multiple analysis relied upon a set of base case projections the
    plaintiff provided to its bank for deal financing, which applied growth rates from the
    buyer’s previous successes to calculate future earnings for the systems. These
    projections provided a “sound, conservative estimate” of growth in operating cash
    flows the plaintiff could have expected by acquiring the cable systems.308 The
    estimates had “the added benefit of having been relied upon by a party—the bank—
    with a strong interest in getting repaid” and were in line with earlier projections of
    operating cash flows.309
    306
    See WaveDivision, 
    2010 WL 3706624
    , at *22 (awarding damages based on the
    difference between what the buyer expected to generate and what it could have expected if
    the seller had been truthful); see also SIGA II, 132 A.2d at 1111 (affirming an award of
    expectancy damages based on lost profits from the failure to negotiate an agreement in
    good faith); Harrington v. Hollingsworth, 
    1992 WL 91165
    , at *4 (Del. Super. Apr. 15,
    1992) (awarding lost profits); Mobile Diagnostics, Inc. v. Lindell Radiology, P.A., 
    1985 WL 189018
    , at *4 (Del. Super. July 29, 1985) (same).
    307
    
    2010 WL 3706624
    , at *22.
    308
    Id. at *23.
    309
    Id.
    62
    The record before me is devoid of similarly reliable evidence to support
    NetApp’s projected future cash flows. The Cloud Jumper Management Projections
    that NetApp used to create the Standalone and Combined Projections were unrefined
    and doubled software revenue year-over-year based on a single year of earnings
    data.310       The haircuts NetApp applied to the Management Projections were
    immaterial.311 Contemporaneous documents suggest that NetApp personnel viewed
    the revenue projections as aggressive.312
    At bottom, NetApp’s calculation is unsound. “Damages are not recoverable
    for loss beyond an amount that the evidence permits to be established with
    reasonable certainty.”313      I therefore reject NetApp’s $37.7 million damages
    estimate.
    310
    JX 78.
    311
    See Hickey Opening Rep. ¶¶ 26-28, 33 n.51; JX 93.
    312
    See Kleinrichert Rebuttal Rep. 10-11; JX 506 at 3 (discussing Cloud Jumper’s revenue
    modeling as “very aggressive” and observing “the revenue transition slowing the total
    growth, not accelerating”); JX 259 at 9 (“Revenue team hasn’t performed diligence over
    the [Cloud Jumper] historics (are the numbers just made up, do the contracts tie to ledgers)
    or the NetApp model (do the growth rates, valuation approaches and synergies make any
    sense).”); id. at 45 (discussing that Cloud Jumper “growth estimates . . . may need to be
    revised downwards once the emergency situation is resolved”); id. at 12 (observing that
    Cloud Jumper revenue model “increase[s] by 3X from $13M to $40M in 3 years” which
    “[s]eem[ed] aggressive”).
    313
    Restatement (Second) of Contracts § 352 (“The main impact of the requirement of
    certainty comes in connection with recovery for lost profits.”).
    63
    ii.      Lack of Proximate Cause
    NetApp’s estimate cannot be adopted for a second reason: it would allow
    NetApp to recover for lost value unrelated to Cloud Jumper’s misstatements.
    Damages for a tort are “broader, more flexible, and more encompassing than the
    remedy for a breach of contract, even when expectancy is the measure.”314
    Nevertheless, damages are generally limited to those “resulting from the direct and
    natural consequence of [the plaintiff] acting on the strength of the defendant’s
    statements.”315 NetApp’s requested damages go further.
    Hickey focuses on two categories of synergies that NetApp contemplated
    while pursuing Cloud Jumper. The first are “Software Uplift Synergies,” which are
    revenue synergies NetApp anticipated from selling a higher volume of Cloud Jumper
    software through NetApp’s sales channels and larger sales force. The second
    category, “Other Synergies,” were incremental revenues NetApp hoped to realize by
    selling more of its preexisting storage products with added functionality from Cloud
    Jumper’s software.        The Software Uplift and Other Synergies account for a
    substantial portion of the cash flows Hickey calculated as damages.
    P’rs & Simon, Inc. v. Sandbox Acqs., LLC, 
    2021 WL 3159883
    , at *5 (Del. Ch. July 26,
    314
    2021) (ORDER).
    315
    LCT Cap., 249 A.3d at 91 (quoting Stephenson, 
    462 A.2d at 1077
    ).
    64
    I cannot conclude that any loss of value associated with these synergies was
    proximately caused by Cloud Jumper’s fraud. NetApp understood that achieving
    the Combined Projections required it to bring “much of the value in the solution.”316
    In other words, NetApp “own[ed] all the risk of execution.”317 It failed to deliver.318
    Just four months after closing, NetApp decided to end-of-life Cloud Jumper’s
    VDI product.319 NetApp never attempted new sales of Cloud Jumper software, even
    though the product performed as expected.320 It retained Cloud Jumper’s existing
    customers, intellectual property, and personnel.321 The Cloud Jumper engineering
    team was moved to develop a new VDI product within Spot—another (significantly
    larger) company acquired by NetApp.322 In such circumstances, awarding NetApp
    damages in excess of the purchase price would amount to a windfall.323
    316
    Mitzenmacher Tr. 251-52, 257; see also Avadhanam Dep. 94-96, 133.
    317
    Mitzenmacher Dep. 50-51.
    318
    See SIGA II, 
    132 A.3d at 1133
     (observing that the trial court appropriately used limited
    post-breach evidence “to confirm its conclusions as to the parties’ reasonable expectations
    at the time of the breach”).
    319
    See Lye Dep. 229; see also 
    id. at 53-54
    .
    Picarello Tr. 82-83; Mitzenmacher Tr. 359-60 (“[T]he product wasn’t defective in any
    320
    way.”).
    321
    See Lye Dep. 230; JX 298 at 63 (assigning values to assets retained from Cloud Jumper).
    322
    See Lye Dep. 229; Picarello Dep. 17-18; Picarello Tr. 71; see also JX 298 at 35 (showing
    that NetApp acquired Spot for $340 million on July 9, 2020).
    323
    See, e.g., Paul v. Deloitte & Touche, LLP, 
    974 A.2d 140
    , 146 (Del. 2009) (stating that
    breach of contract damages should not provide a “windfall” to the plaintiff).
    65
    b.     The Defendants’ Estimate
    NetApp asserts that the court should reject Kleinrichert’s analysis because “a
    DCF analysis is the only way to evaluate the Internal Billings’ effect on NetApp’s
    expectations for the combined entity.”324 This belief is incorrect.325 It is also belied
    by the record. Contemporaneous documents show that NetApp viewed market
    multiples as a more accurate measure of value for a startup like Cloud Jumper than
    a DCF method.326 NetApp’s DCF analysis is especially unreliable given the error in
    the input of the terminal value of free cash flow.327
    Consistent with Delaware law and the facts of this case, Kleinrichert
    compared the value of Cloud Jumper that NetApp expected ($35 million) to the value
    324
    Pl.’s Post-trial Reply Br. 28.
    325
    See supra at notes 234-35 and accompanying text; see also WaveDivision, 
    2010 WL 3706624
    , at *23 (noting that projections “could be used to perform either a DCF analysis
    or a multiple of EBITDA analysis” and rejecting an argument that the court should not
    “deviate from the ‘standard’ DCF analysis”); Shannon P. Pratt & Alina V. Niculita,
    Valuing a Business: The Analysis and Appraisal of Closely Held Companies 262 (5th ed.
    2008) (“The use of comparable publicly held corporations as a guide to valuation, as a
    practical matter, may be the most important and appropriate technique for valuing a
    privately held operating business.” (citation omitted)).
    326
    JX 189 (“The reason we use triangulation in valuing startups is that market based
    multiples are usually more accurate measures of value in an acquisition than DCF, which
    is conjuncture [sic], in best of cases.”); see also JX 500 (“Valuation is a triangulation with
    [m]arket comps as a crucial component, precisely because DCF is not an exact science.”);
    JX 187 at 2 (“Sorry to say this, but with tweaking the inputs into a P&L and the discount
    rate, I can produce almost any DCF value for any business. . . . Again, this is also the
    reason we use a market[-]based approach to validate the DCF work.”).
    327
    See Hickey Rebuttal Rep. 19-21 & n.44.
    66
    that it received in February 2020. As previously described, Kleinrichert’s market
    approach used revenue multiples to calculate the value of Cloud Jumper after
    correcting for Internal Billing. His analyses yielded an actual value of $30.4 million
    using the guideline public companies method and $35.0 million using the guideline
    transactions method.
    Kleinrichert’s use of a revenue multiple is appropriate.328 A company like
    Cloud Jumper that experiences negative earnings during its early operational stages
    can have positive market value where investors believe it will achieve earnings and
    cash flow in the future.329 NetApp calculated its expectations for Cloud Jumper
    using an EV/revenue multiple.330
    Nonetheless, I decline to adopt Kleinrichert’s guideline transactions analysis.
    At the time of the acquisition, VDI companies traded at considerably higher
    multiples than MSP companies.331 But Kleinrichert’s guideline transactions analysis
    328
    See Kleinrichert Tr. 828 (“I don’t think there’s any dispute about using a revenue
    multiple.”); see also Aswath Damodaran, Investment Valuation: Tools and Techniques for
    Determining the Value of Any Asset 542-43 (3d ed. 2012) (explaining that “[f]or young
    firms that have negative earnings, multiples of revenues have replaced multiples of
    earnings” to value companies); 
    id.
     (describing revenue multiples as “attractive” for reasons
    including their availability for “very young firms”).
    329
    See Kleinrichert Revised Opening Rep. 33-34.
    330
    See, e.g., JX 93.
    331
    See Hickey Rebuttal Rep. ¶¶ 39-40.
    67
    resulted in a median EV/revenue multiple of 2.5x for VDI transactions—a figure
    that is lower than the 2.9x multiple he observed for MSP transactions.332
    Kleinrichert’s guideline public companies method does not suffer from the
    same defect. It indicates a median EV/revenue multiple of 4.96x for the VDI
    companies and a 2.13x multiple for the MSP companies he selected.333 Kleinrichert
    calculated a blended multiple of 2.46x, which falls on the lower end of the range of
    blended multiples NetApp estimated for guideline public companies—adjusted for
    Internal Billing—of 2.3x to 4.3x.334 Using a blended multiple is not only consistent
    with NetApp’s contemporaneous analysis, but also reflects its expectation that Cloud
    Jumper MSP customers would become VDI customers.335
    Further, the defendants have met their burden of showing that the guideline
    companies considered in this analysis are appropriate comparables for Cloud
    Jumper.336       Kleinrichert’s selection of guideline companies resulted from a
    332
    See 
    id.
     ¶ 40 & Fig.1.
    333
    Kleinrichert Opening Rep. at Sched. 4.1; see also Kleinrichert Revised Opening Rep.
    33 & n.166.
    334
    See Kleinrichert Opening Rep. at Scheds. 4.0 & 4.2. The public company multiples
    considered by NetApp, as adjusted based on a revised 2019 revenue mix, were: 2.30x (low
    end), 3.30x (median), and 4.30x (high end). See id. at 42, Sched. 6.1; see also JX 93
    (“Football Field” Tab) (listing “trading comps” multiples as 2.7x (low end), 3.7x (median),
    4.7x (high end)).
    335
    See Kleinrichert Tr. 837-39.
    336
    See In re Cellular Tel. P’ship Litig., 
    2022 WL 698112
    , at *30 (Del. Ch. Mar. 9, 2022).
    68
    reasonable and thorough process.337 Two of the four VDI and two of the four MSP
    companies he chose overlap with the trading comparables identified by NetApp.338
    Kleinrichert did not adopt the other guideline companies NetApp identified; he
    selected four other public companies (two MSP and two VDI) based on his
    research.339
    The guideline companies included in Kleinrichert’s analysis are substantially
    larger than Cloud Jumper and (unlike Cloud Jumper) have generated EBITDA. But
    perfect comparables do not exist. Like other assumptions in valuation methods, the
    selection of guideline companies is more an art than a science.340 The gross profit
    337
    Kleinrichert Tr. 830-31 (describing his research of public companies, review of
    company descriptions, and comparison of businesses most relevant to assessing Cloud
    Jumper); Kleinrichert Opening Rep. 5 & Scheds. 4.1-4.3.
    338
    Compare JX 93 (“Trading Comps Output” Tab) (listing Citrix Systems, VMWare, Inc.,
    Microsoft Corporation, and Hewlett Packard Enterprise as VDI comparables; and
    Accenture plc, Cognizant Technology Solutions Corporation, Infosys Ltd., Tata
    Consultancy Services as MSP comparables) with Kleinrichert Opening Rep. at Sched. 4.2
    (listing Citrix Systems, VMWare, Inc., Oracle, and Nutanix, Inc. as VDI comparables; and
    Internal Business Machines Corporation (IBM), Cognizant Technology Solutions
    Corporation, Accenture plc, and DXC Technology Company as MSP comparables).
    339
    Kleinrichert Tr. 828-29.
    340
    See In re S. Peru Copper Corp. S’holder Deriv. Litig., 
    52 A.3d 761
    , 816 (Del. Ch. 2011)
    (noting that determining an appropriate valuation “is not a straightforward exercise and
    inevitably involves some speculation”); Answath Damodaran, Damodaran on Valuation:
    Security Analysis for Investment and Corporate Finance 236 (2d ed. 2006) (“[T]he lack of
    transparency regarding the underlying assumptions in relative valuations makes them
    particularly vulnerable to manipulation.”); see also Kleinrichert Tr. 806-07, 828-31, 834-
    36; Avadhanam Dep. 131-32 (“There are never perfect comparables for any business.”);
    id. at 133, 209-11.
    69
    NetApp is entitled to recover the diminution in value resulting from Cloud Jumper’s
    fraud and breaches of contract. This figure is calculated by subtracting the actual
    value of Cloud Jumper ($30,401,022) from the value of Cloud Jumper as represented
    to NetApp (the $35,000,000 purchase price). The difference is $4,598,978, which I
    award to NetApp as damages.343
    D.     Attorneys’ Fees
    Finally, NetApp seeks an award of attorneys’ fees and costs. Section 10.10
    of the Merger Agreement provides: “If a claim or dispute brought in accordance
    herewith is resolved in the favor of a Party hereto, such Party shall be entitled to,
    and awarded, its costs and expenses incurred in connection with the resolution of
    such claim or dispute (including reasonable attorneys’ fees).”344
    The defendants do not challenge the application of this provision. Rather,
    they contend that it supports an award of their own fees. 345 Given that NetApp’s
    claims have been resolved in its favor, it is entitled to an award of costs and expenses
    (including reasonable attorneys’ fees) under Section 10.10.
    343
    It bears noting that this amount is at the high end of NetApp’s contemporaneous estimate
    of its losses upon discovering the Internal Billing. Mitzenmacher adjusted NetApp’s pre-
    LOI transaction and trading comparable analyses to correct for the effect of Internal Billing
    on NetApp’s valuation of Cloud Jumper. He calculated “$2.5M-$5M of valuation impact
    based on multiples.” JX 288 at 5.
    344
    Merger Agreement § 10.10.
    345
    Defs.’ Post-trial Br. 59.
    71
    III.   CONCLUSION
    Consistent with the above, judgment is entered in favor of NetApp. NetApp
    is entitled to an award of damages totaling $4,598,978. NetApp is also entitled to
    interest at the legal rate starting on November 20, 2020,346 and to an award of its
    reasonable fees and expenses. The parties shall confer on a form of final order and
    file it within 14 days.
    346
    See Citadel Hldg. Corp. v. Roven, 
    603 A.2d 818
    , 826 (Del. 1992) (“In Delaware,
    prejudgment interest is awarded as a matter of right.”). “The Court of Chancery generally
    looks to the legal rate of interest, as set forth in 6 Del. C. § 2301, as the ‘benchmark’ for
    the appropriate rate of pre- and post-judgment interest.” Murphy Marine Servs. of Del.,
    Inc. v. GT USA Wilm., LLC, 
    2022 WL 4296495
    , at *24 (Del. Ch. Sept. 19, 2022) (citation
    omitted).
    72