BROKER BETS BIG ON GAMBLING! Swipes $2.5M from Investors for Slots!

SEC v. Waldon Fenster — U.S. Securities and Exchange Commission Litigation Release No. 26628, dated September 4, 2026.

Waldon Fenster, an unregistered investment adviser, defrauded 23 investors out of approximately $3.6 million by falsely promising high returns through bridge loans. Instead, he misappropriated over $2.5 million for personal expenses, including gambling, and returned the rest to a few investors.

In Plain English

Imagine you give money to a friend who promises to invest it in safe, high-interest loans for small businesses. Your friend tells you they'll make a lot of money for you, but instead, they take most of your money to gamble and buy things for themselves. When you ask for your money back, they lie and say it's earning a lot, but it's really gone.

Disclaimer: all facts are drawn from the SEC's own filings; the claims described are allegations unless and until a court rules or the parties settle, and some cases end in dismissal.

How the Alleged Scheme Worked

  1. Setting Up the Fund In 2021, Waldon Fenster created a private fund initially named 'Last Mile Loan' (also known as Next Generation Legacy Fund, LLC). He initially claimed it would invest in early-stage companies, but this strategy was unsuccessful.
  2. Changing the Strategy In early 2023, Fenster changed the fund's strategy. He told investors the fund would generate over 20% profits by issuing short-term, high-interest bridge loans to small businesses.
  3. The False Pitch Fenster represented that these loans would help small businesses secure larger financing from established lenders, which would then be used to repay the fund with interest. He claimed to identify businesses through a thorough due diligence process.
  4. Raising Funds From January 2023 to March 2024, Fenster raised approximately $3.6 million from 23 individual investors, many located in the Chicago metropolitan area.
  5. Misappropriating Funds Instead of issuing loans, Fenster allegedly misappropriated more than $2.5 million ($2,516,120.80) from the fund's investors.
  6. Personal Use of Funds Fenster used the misappropriated funds for personal expenses, including gambling, trips, and general living expenses.
  7. Returning Remainder Funds Fenster returned the remaining investor funds to certain investors he hoped would refer new clients, and to one investor who threatened legal action.
  8. Lying to Investors When investors sought to withdraw their money, Fenster offered excuses and falsely claimed the fund had earned substantial returns, delaying their requests.
  9. Scheme Unravels As his scheme unraveled, Fenster eventually admitted to investors that he had 'made mistakes' and that their money was gone.

The Enforcement Action

SEC Files Settled Action as to Chicago-Area Investment Adviser for Allegedly Misappropriating Client Funds. On September 3, 2026, the Securities and Exchange Commission filed a settled action as to former Downers Grove, Illinois resident Waldon Fenster, an unregistered investment adviser and founder of a private fund known as “Last Mile Loan,” alleging that Fenster lied to investors and misappropriated money for gambling and personal expenses. According to the SEC’s complaint, filed in the United States District Court for the Northern District of Illinois, from January 2023 to March 2024, Fenster raised approximately $3.6 million for the fund from 23 individual investors. As alleged in the complaint, Fenster told investors that the fund would generate profits of more than 20% by issuing short-term, high- interest bridge loans to small businesses that were seeking greater financing from established lenders. According to the complaint, however, the fund never issued any loans. Rather, Fenster allegedly misappropriated more than $2.5 million from the fund’s investors’ funds for gambling, trips, and personal living expenses, and returned the remainder of investors’ funds to certain investors whom he hoped would refer new potential investors to the fund. In addition, as alleged in the complaint, when investors reached out to Fenster seeking to withdraw money from the fund, Fenster offered excuses for why they could not withdraw and falsely represented that the fund had earned substantial returns. Without admitting the allegations in the SEC’s complaint, Fenster consented to the entry of a final judgment, subject to court approval, in which he agreed to be permanently enjoined from violating the antifraud provisions of Section 17(a) of the Securities Act of 1933, Section 10(b) of the Securities Exchange Act of 1934 and Rule 10b-5 thereunder, and Sections 206(1), 206(2), and 206(4) of the Investment Advisers Act of 1940 and Rule 206(4)-8 thereunder; to pay $2,516,120.80 in disgorgement plus $450,012.39 in prejudgment interest and a $236,451.00 civil penalty; and to be prohibited from issuing, purchasing, offering, or selling any security, except for purchases or sales for his own personal account, and from being associated with any broker, dealer, or investment adviser. The SEC’s investigation was conducted by Matthew Connelly and Rebecca Hollenbeck of the SEC’s Chicago Regional Office under the supervision of Anne Graber Blazek.

Named in this action: Waldon Fenster.