[DO NOT PUBLISH]
IN THE UNITED STATES COURT OF APPEALS
FOR THE ELEVENTH CIRCUIT

____________ ____________ No. 19

- 12765 Non

- Argument Calendar

________________________ D.C. Docket No. 1:16

- cv - 03298

- SCJ
SECURITIES AND EXCHANGE COMMISSION , Plaintiff

- Appellee,

versus WATKINS PENCOR, LLC , MASADA RESOURCE GROUP, LLC, DONALD V. WATKINS, P.C., DONALD V. WATKINS , SR. Defendant s - Appellant s .

________________________ Appeal from the United States District Court for the Northern District of Georgia

________________________ (April 28, 2020) Before BRANCH , LU CK , and FAY , Circuit Judges.
PER CURIAM:

Case: 19-12765 Date Filed: 04/28/2020 Page: 1 of 172 The Securities and Exchange Commission brought this enforcement action against Donald Watkins Sr. and his company, Masada Resource Group, LLC , f

ollowing a series of emails in which they solicit ed three loans totaling $2,150,000
from former NBA player Charles Barkley. Rather than us e Barkley’s money for the investment opportunities promised in th o se emails, Watkins and Masada used them
for Watkins’ personal gain. T hey used Barkley’s funds to pay t he mortgage on Watkins’ personal plane , credit card bills, and the alimony Watkins owed his ex

wife . The SEC claim ed that Watkins and Masada defrauded Barkley by making numerous misrepresentations in their emails to him

. Watkins and Masada, in
response , maintain ed that the representations made in th ose emails were not fraud ulent because Masada’s operating agreement authorized Watkins to use Barkley’s money in the way that he did. T he district court granted summary judgm ent in favor of the SEC, and against Watkins and Masada, concluding that the re was no genuine issue of material fact that the representations in the emails were false, material, and made knowingly or with severe recklessness

. W e affirm. FACTUAL BACKGROUND AND PROCEDURAL HISTORY Watkins was a lawyer and businessman who , in 2005 , became Masada’s chief executive officer after its founder had passed away. Masada was a company that supposedly had patents for technology capable of turning waste into fuel

- grade ethanol

. Watkins explained that Masada’s “business plan [was] to go around,

Case: 19-12765 Date Filed: 04/28/2020 Page: 2 of 173 identify partners, qualified partners, execute the right contracts with them, and then to bundle those contracts and then sell them, along with [its] technology, to an operating company.” B ecause Masada initially “was not in a position to pay” him, Watkins “deferred [his] compensation from Masada from day one.” During his time as Masada’s chief executive officer, Watkin s pursued other efforts . He competed for “an NFL franchise opportunity” in Masada’s name and attempt ed to sell Masada to Waste Management, Inc., a publicly traded company. Unfortunately for Watkins and Masada, n either venture was successful , and Masada, as of 2010, had yet to earn
any revenue. As a result, Watkins faced problems with his personal finances. I n April 2010, for example , he sent a letter to a lender request ing forbearance on one of his personal loans , writing that his “personal income no longer allow[ed] [him] to comfortably service [hi s] debt under the current terms and conditions. . . . Due to income losses of prior years, [one of Watkins’ other companies] [would] be in even less of a position to make loans to [him] in 2010.” Moreover, his credit cards had been suspended, and he still owed his ex

- wife alimony. Around this time, Watkins solicited investments that he claimed were Masada

- related from several individuals who had a financial interest in Masada ,

Case: 19-12765 Date Filed: 04/28/2020 Page: 3 of 174 including Barkley

. 1 Unknown to Barkley, however, Watkins would later use th e money he solicited to reduce the strain on his personal finances. The 2010 Note On May 8, 2010, Watkins sent Barkley and other investors email s soliciting four $1,000,000 investment s. Watkins’ email to Barkley , Glenn Guthrie (Barkley’s financial advisor), and Donald Watkins Jr. (Watkins’ son) stated : We have an immediate opportunity to partner with Chip Rosenbloom and his family (owners of the St. Louis Rams) to secure long

- term waste management contracts for a Masada waste

- to

- ethanol in [sic] Morocco. They can also facilitate a partnership with

. . . Mexico’s richest man [] for Masada contracts and projects in Mexico.

. . . . I do not want to take private equity money to cover the development costs for these new oppo rtunities. We would have to give up too much equity in return and we have already planned the first of three Masada initial public offerings for later this year. In short, because of all of the work we have done with Masada during the past 14 years, new equity partners coming in at this late date would get all of the upside in these transactions with very little downside. The best option for preserving our collective economic equity value is to borrow the $4 million needed to cover the development costs for this list of new countries from our existing stakeholders. I have decided to invite you and three other financially secure Masada stakeholders to lend us $1 million each for 12 months. In exchange for your loan, we would: (a) pay you interest at matu rity at a rate of 10% per annum, (b) award you an additional 1% on your existing economic interest in the Masada companies, and (c) award you a 1% profits interest in each

1 The two had met in Alabama years prior, and their relationship had further developed when Barkley invested in another one of Watkins’ businesses

.

Case: 19-12765 Date Filed: 04/28/2020 Page: 4 of 175 facility to be built in Morocco, Mexico, Senegal, South Africa, and South Korea.
Tw o days later, Watkins emailed Barkley that he would “split the first $1 million for Morocco and Mexico until the other funds c[a]me in.” On May 14, 2010, four days after Watkins’ initial email, Barkley agreed to provide $1,000,000 in exchange for a promissory note. The promissory note matured in one year and promised to pay Barkley the principal sum with interest at ten percent per year . Consistent with the May 10 email, the note also awarded Barkley an additional one percent on an existing economic interest he previously
had in Masada

- related entities and one

- percent interest in any profits stemming from each facility built in Morocco, Me xico, Senegal, South Africa, and South Korea. Finally, the note provided that it “was made and transacted solely for business purposes related to Masada Resource Group, LLC.” The same day Watkins signed the note, Barkley wired approximately $ 1,000,000 to Watkins ’ bank account. 2 Immediately a fter receiv ing the Barkley wire , Watkins directed his son to make a series of outgoing wire transfers. The largest was for $750,000 and sent to Dan Meach u m , who had previously loaned money to Watkins and the Masada entities. Watkins also wired $41,491.14 to the company that held the m ortgage on his personal plane ; $10,015 to a “House

2 The day before Barkley’s wire, Watkins’ bank account contained less than $5,000. Case: 19-12765 Date Filed: 04/28/2020 Page: 5 of 176 Account,” which he described as being for rent and expenses for his then

- girlfriend ’s ho me in Atlanta; and $10,000 to his ex - wife in alimony

. The 2011 Note On May 13, 2011, Watkins sent another email to Barkley seeking additional funds: As we gear up for the anticipated Masada

- Waste Management transaction, we will be expending significant sums on [New York], San Francisco, and Atlanta investment bankers and lawyers. I had planned on borrowing $1 million for this special purpose from one of my commercial bankers later today or Monday. We will be repaying the loan at the closing of the [Waste Management] transaction. If you are interested in lending the money instead, we will borrow the $1 million from you at the same 10% per annum intere st rate we are paying on your current loan. We will also pay you an additional $100,000 friendship kicker for the convenience of not having to undergo the lengthy commercial banking loan underwriting process and for the speed at which you execute your loa n transactions. We will retire this special purpose at the closing of the [Waste Management] transaction or within 12 months, whichever occurs first. Five days later, Barkley again agreed to provide $1,000,000 to Watkins in exchange for a promissory note . This note matured in a year, accrued interest at the rate of ten percent per year , and awarded Barkley $100,000 as a “loan service fee” on the maturity date. It further stated that it “was made and transacted solely for business purposes related to Mas ada Resource Group, LLC and affiliated entities/persons.”

Case: 19-12765 Date Filed: 04/28/2020 Page: 6 of 177 On May 23, 2011, Barkley wired $1,000,000 to Watkins ’ bank account. 3 That same day, the following transactions occurred from Watkins’ bank account: Drew Watkins (Watkins’ other son) deposited a $ 7,000 check that had “Gift” written in the memo line ; Watkins’ ex

- wife deposited a $50,000 check with the memo line “Partial Alimony” ; his then

- girlfriend received a $41,816 wire for the “House
Account” ; and a law firm deposited a $9,678.50 check

. On t he next day, there were more transactions: another law firm deposited a $150,000 check for its work on litigation for another non - Masada company ; he made two wires, one for $10,008.63
and the other for $11,904.80 , for repayment of his personal loans; and he sent a $255,703 check to the United States Treasury to pay for his personal tax liability. The 2013 Note On May 24, 2013, Watkins sent Barkley an email asking for more funds: Earlier this week, I had to cover $600,000 in April and May expenditures related to

. . . projects [in Namibia, South Africa, the United Kingdom, the United Arab Emirates , South Korea, and Turkey], including some substantial legal fees for Nabirm relating to the $10 million investment transaction currently being handled by Daniel Stewart & Company in London. This was way more than we had originally budgeted in project

- related expenses during this two

- month period. I paid all of these expenses, but these p ayments have left my office account far too thin for my personal comfort. Plus, our June allotment of working capital will not hit my office account until June 1. Can you lend me $150,0 0 0 to cover my financial exposure between today and June 1? I will be able to pay it right back to you shortly after

3 The day before Barkl ey’s wire, Watkins’ bank account had a negative balance

. Case: 19-12765 Date Filed: 04/28/2020 Page: 7 of 178 I return to the US. If you can facilitate this personal request, please have [Guthrie] call [Watkins Jr.] and take care of it today (Frida y). . . . I have only approached you about this very personal matter. Your demonstrated commitment to confidentiality with respect to our financial arrangements have made me feel comfortable enough to make this special request. Shortly after sending t he email to Barkley, Watkins sent an email to Watkins Jr. that outlined how the Barkley money was to be spent: If Charles comes through, please pay your AmEx ($79,000), Jessica’s [ 4 ] AmEx ($40,750.23) and My AmEx ($10,000). Pay $2,000 more on my Visa and pay a one

- month $2,500 for Jessica so that she can pay her personal bills. Leave the rest in the office account for payroll and overdrafts. I am working another source for the mort gage arrearage money ($150,000) and other bills ($50,000). I will send that email out in a few hours. We will climb out of this financial hole, but it takes a lot of focus and help. A few days later, Barkley provided Watkins $150,000 in exchange for a promissory note. The note “was made and transacted solely for business purposes related to Masada Resource Group, LLC

. ” Watkins ’ bank account statements showed that Watkins spent less than $300,000 in the two months preceding the May
24 email and that none of that money was for “Daniel Stewart & Company

. ” On the same day Barkley wired the money, Watkins made payments of $79,000 to Watkins

4 “ Jessica ” refers to Jessica Findley, who worked with Masada and had a Masada email address. Case: 19-12765 Date Filed: 04/28/2020 Page: 8 of 179 Jr.’s American Express credit card bill, 5 $9,400 to his own American Express credit card bill, and $40,750.23 to Jessica Findley’s American Express credit card bill. Procedural History
In 2016, the SEC filed a complaint against Watkins and Masada

. The SEC alleged that they violated section 17(a) of the Securities Act, 15 U.S.C. § 77q(a) , section 10(b) of the Exchange Act, 15 U.S.C. § 78j(b) , and Rule 10b

– 5, 17
C.F.R. § 240.10b

– 5 , by making material misrepresentations in their solicitations of Barkley’s funds

. T wo years into the litigation , the district court granted partial summary judgment in favor of the SEC , and against Watkins and Masada , f inding that Watkins violated the Securities Act and the Exchange Act with respect to the three promissory

notes , and Masada violated these provisions with respect to the 2010 and 201 1 notes. After further litigation , t he district court (1) held Watkins and Masada joint ly and severally liable for disgorgement of $2,000,000 plus prejudgment interest, (2) held Watkins individually liable for an additional $150,000 plus prejudgment interest, (3) imposed a $1,450,000 civil penalty on Masada, (4) imposed a $450,000

5 W at kins Jr.’s credit card statement for April 2013 contained a $915 charge for clothing or accessories at Hermes of Paris, a $2,800 payment to a media company that advertised Watkins Jr.’s insurance business, a $3,000 contribution to the University of Alabama Birmingham, a $5,000 charge for alimony to Deandra Watkins, a $757.74 charge for a matt ress, a $21.98 charge for Watkins Jr.’s gym membership, a $58.25 charge for Watkins Jr.’s warranty on his personal residence, and charges for meals at various restaurants.

Case: 19-12765 Date Filed: 04/28/2020 Page: 9 of 1710 civil penalt y on Watkins, and (5) permanently enjoined Watkins and Masada from further violating the antifraud provisions

. Watkins now appeals. STANDARD OF REVIEW We review a district court’s order on summary judgment de novo. SEC v. Levin , 849 F.3d 995, 1000 (11th Cir. 2017). “In conducting our analysis, we construe the facts and draw all reasonable inferences in the light most favorable to the non

- moving party.” SEC v. Monterosso , 756 F.3d 1326, 1333 (11th Cir. 2014).
S ummary judgment is appropriate “if the movant shows that there is no genuine dispute as to any material fact and the movant is entitled to judgment as a matter of law.” Fed. R. Civ. P. 56(a). “If no reasonable jury could return a verdict in favor of the nonmoving party, there is no genuine issue of material fact and summary judgment will be granted.” Morton v. Kirkwood , 707 F.3d 1276, 1284 (11th Cir. 2013)

. DISCUSSION On appeal, Watkins and Masada argue that : (1) there were genuine issues of
material fact as to whether they made material misrepresentations ; (2) the district court did not apply the correct summary judgment standard ; and (3) there were genuine issues of material fact as to whether they made the material misrepresentations knowingly or with severe r ecklessness.

Case: 19-12765 Date Filed: 04/28/2020 Page: 10 of 1711 Material Misrepresentation s Watkins and Masada contend that Masada’s operating agreement purportedly allowed Watkins to use the funds Barkley loaned him in any manner he cho se. As a result, they claim that a genuine issue exists as to whether they made misrepresentations and, if they did, whether those misrepresentation s were material. For the SEC t o succeed on its section 10(b) and Rule 10b

– 5 claim s at the
summary - judgment stage , 6 the re must be no genuine issue of material fact that Watkins and Masada made “(1) material misrepresentations or materially misleading omissions, (2) in connection with the purchase or sale of securities, (3) . . . with

sc ienter.” SEC v. Merch. Capital, LLC , 483 F.3d 747, 766 (11th Cir. 2007). Similarly, on its section 17(a)(1) claim , the SEC must show that there is no genuine issue of material fact that Watkins and Masada made “(1) material misrepresentations or material ly misleading omissions, (2) in the offer or sale of securities, (3) . . . with scienter.” Id. A misrepresentation is material if “a reasonable man would attach importance to the fact misrepresented or omitted in determining his course of action.” Id. ; see also Carvelli v. Ocwen Fin. Corp. , 934 F.3d 1307, 1317 (11th Cir. 2019) (“A misrepresentation or omission is material if, in the light of the facts existing at the

6 “The scope of Rule 10b

– 5 is coextensive with the coverage of [section] 10(b).” S EC v. Zandford , 535 U.S. 813, 816 n.1 (2002).

Case: 19-12765 Date Filed: 04/28/2020 Page: 11 of 1712 time, a reasonable investor, in the exercise of due care, would have been misled by it.” (internal quotation marks omitted)). “Course of action,” in this context, means an “investment decision.” Brink v. Raymond James & Assocs., Inc. , 892 F.3d 1142, 1148 (11th Cir. 2018) (quoting SEC v. Goble , 682 F.3d 934, 943

– 44 (11th Cir. 2012)). “The S upreme Court has explained that materiality in federal securities law requires a ‘substantial likelihood that the disclosure of the omitted fact would have been viewed by the reasonable investor as having significantly altered the total mix of information made available.’ ” Id. (quoting Basic Inc. v. Levinson , 485 U.S. 224,
23 1

– 32 (1988) ). The materiality requirement’s purpose is “to filter out essentially useless information that a reasonable investor would not consider significant, even as part of a larg er ‘mix’ of factors to consider in making his investment decision.” Levinson , 485 at 234. “The question of materiality is not subject to a bright

- line test but instead depends on the specific circumstances of each case.” Carvelli , 934 F.3d at 1317 (cita tion omitted). The representations Watkins and Masada made to Barkley shortly before the execution of the 2010, 2011, and 2013 promissory notes are the focal point of the SEC’s action. The record is undisputed that the representations were patently false. Despite the promise to use the loan money to secure long

- term waste management contracts, to pay for attorneys and investment bankers to finish the Waste Management deal, and to reimburse Masada for projects in Af rica, Europe, Case: 19-12765 Date Filed: 04/28/2020 Page: 12 of 1713 and Asia, Watkins and Masada used the money for non

- Masada expenses. They used the 2010 loan to refund another investor, pay the mortgage for Watkins’ personal plane, pay for his alimony, and pay for his girlfriend’s living expense s . Watkin s spent the money from the 2011 loan on unrelated legal fees , his alimony, his girlfriend’s living expenses, his personal tax liability, and his personal loan. As for the representations in the 2013 email, Watkins did not cover $600,000 in Masada
expenses in April and May 2013, did not receive a significant allotment of working capital on June 1, 2013, and spent the $150,000 to pay off personal credit card bills. These misrepresentations were material as a reasonable investor would “attach importance” to the fact that Watkins and Masada used the funds loaned to them to pay for Watkins’ personal obligations rather than for the lucrative opportunities represented in their emails. 7 Merch. Capital , 483 F.3d a t 766. Watkins and Masada instead argue that Masada’s operating agreement allowed them to use Barkley’s money for “Masada purposes ” and Watkins’ personal debts, personal expenses, alimony, and tax obligations were Masada expenses. But this argument, as the district court correctly noted, “misses the point

. ” Ev en if the operating agreement allowed Watkins to spend an investor’s money on his perso nal

7 For an example of what a reasonable investor would think is important, Barkley, in his deposition, indicated that his “biggest concern [was] that [Watkins] did not use the money to make [Masada] grow.” W hen the SEC specifically asked Barkley whether he would have given Watkins money had he known that Watkins was going to spend the money on these personal expenses, Barkley responded, “No way.”

Case: 19-12765 Date Filed: 04/28/2020 Page: 13 of 1714 expenses, it did n’t allow him to lie to an investor about the reasons he was asking for money

. Just because he could spend the money for any reason he wanted, doesn’t
mean that he could get money by fraud and deceit. The operating agreement was

not a license to commit fraud. The Correct Standard Watkins and Masada also argue that the district court applied the wrong summary judgment standard. They maintain that the district court erred in not explicitly saying , as to the question of materiality, that there was no genuine issue of material fact

. This argument has no merit

. A review of the district court’s order reveals that it applied the correct standard. The district court correctly cited to Federal Rule of Civil Procedure 56(a) and stated that the party seeking summary judgment had to show that there was no genuine issue of material fact, that the movant had to be entitled to judgment as a matter of law, and that it would review the facts in the light most favorable to the nonmoving party. The district court also made the explicit finding that Watkins’ and Masada’s “misr epresentations were indisputably material.” In any event, our review of the district court’s order is de novo, and we have already concluded that there is no genuine issue of material fact on the materiality issue

.

Case: 19-12765 Date Filed: 04/28/2020 Page: 14 of 1715 Know ing Misconduct or Severe Recklessnes s ( Scienter ) Watkins and Masada final ly argue that “scienter is completely disputed and negated” because “every action” they took was authorized by the Masada operating agreement. This is the same argument they ma d e for why there were no material misrepresentations , but repackaged for the scienter element

. “Scienter may be established by a showing of knowing misconduct or severe recklessness .” 8 Monterosso , 756 F.3d at 1335 (quoting SEC v. Carriba Air, Inc. , 681 F.2d 1318, 1324 (11th Cir. 1982) )

. “Severe recklessness is limited to those highly unreasonable omissions or misrepresentations that involve not merely simple or even inexcusable negligence, but an extreme departure from the standards of ordinary care

. ” Mizzaro , 544 F.3d at 1238 (quotin g Bryant v. Avado Brands, Inc. , 187 F.3d 1271, 1282 n.18 (11th Cir. 1999)). The omission or misrepresentation must “present[] a danger of misleading buyers or sellers that is either known to the defendant or is so obvious that the actor must have been awa re of it.” Carriba Air , 681 F.2d at 1324. The SEC can establish scienter through circumstantial or direct evidence. Monterosso , 756 F.3d at 1335. A lthough the question of scienter is typically left to the trier of fact, summary judgment is appropriate if no reasonable

8 “Corporations, of course, have no state of mind of their own . Instead, the scienter of their agents must be imputed to them.” Mizzaro v. Home Depot, Inc. , 544 F.3d 1230, 1254 (11th Cir. 2008). Case: 19-12765 Date Filed: 04/28/2020 Page: 15 of 1716 jury could find that a defendant acted with out scienter. Id. (citing SEC v. Lyttle , 538 F.3d 601, 603

– 04 (7th Cir. 2008))

. T here was no genuine issue of material fact that Watkins and Masada made the misrepresentations eithe r knowingly or with severe recklessness. The emails themselves show that Watkins and Masada knew or should have known that their misrepresentations presented a n obvious danger of misleading Barkley into believing that the y would spend his money for the pu rposes stated in the emails

. In the 2010 email, rather than asking for money to pay for Watkins’ personal expenses, Watkins and Masada asked Barkley for an investment that would cover development costs for “new opportunities” with the owner of a professio nal football team and “Mexico’s richest man.” Likewise , i n the 2011 email, they asked Barkley for money for the “special purpose” of funding investment bankers and lawyers for the “anticipated” transaction with Waste Management rather than for the purpose of covering Watkins’ personal obligations

. I n the 2013 email, Watkins asked Barkley for money to allegedly cover “ legal
fees

. . . relating to [a] $10 million investment transaction currently being handled .” Watkins knew his mis representations were false because , immediately after sending it, he emailed his son with directions to use Barkley’s money to pay off personal
credit card bills as he neede d this money to climb out of a “financial hole.” From this, the district court rightly observed that Watkins and Masada’s “need to bolster

Case: 19-12765 Date Filed: 04/28/2020 Page: 16 of 1717 [their] misrepresentations ” was “ evidence that [they] deliberately misled [Barkley] because [they] knew [he] would n ot have invested if he knew the true use of the
funds

. ” Watkins and Masada ’s only rebuttal to this evidence is to point to the operating agreement and argue that their misrepresentations were not made with
scienter because they believed that the operating agreement allowed what they did

. As we explained earlier, the re is nothing in the operating agreement that can reasonably be read to allow Watkins to lie or defraud his investors about why he needed the money and w hat it was going to be used for. But even if Watkins unreasonably believed the operating agreement allowed his lies and deceit, at best his reading would be s everely reckless , and he would still be liable under the Securities Act and the Exchange Act. CONCLUSION For these reasons, t he district court did not err in granting summary judgment in favor of the SEC because there was no genuine issue of material fact that Watkins
and Masada made material misrepresentations or that they made those misrepresent ations with scienter. We affirm. AFFIRMED. Case: 19-12765 Date Filed: 04/28/2020 Page: 17 of 17