In this episode, we sit down with Tom Hardin, also known as "Tipper X," the former hedge fund analyst who became one of the most prolific informants in the largest insider trading crackdown in U.S. history. Tom walks us through his journey from rule-following soccer referee in Georgia to Ivy League graduate and rising Wall Street analyst—before crossing the line into insider trading at age 29. What makes this conversation so compelling is not just the crime, but how ordinary it felt at the time. Tom explains how small rationalizations, cultural pressures, ambition, and the normalization of questionable behavior gradually eroded his ethical boundaries. After being arrested and recruited by the FBI, he wore a wire 48 times and helped build over 20 cases in Operation Perfect Hedge, exposing widespread misconduct across the hedge fund industry. We explore the psychology of ethical failure, the "fraud triangle," moral licensing, and the difference between ethics in the classroom and ethics in the real world. Tom also reflects on redemption, forgiveness, mentorship, and how he now defines success after losing his finance career.

Key Points From This Episode:

(0:04) Introduction to Tom Hardin, former hedge fund analyst turned FBI informant.

(5:15) Tom's conviction: One count of securities fraud and one count of conspiracy after four illegal trades netting $46,000.

(6:11) Early life as a rule-following soccer referee and how ambition shaped his identity.

(8:07) The hedge fund world as a meritocracy—high pressure, high stakes, and performance-driven culture.

(9:13) How insider trading networks operated openly in certain hedge fund circles.

(12:21) The legal definition of insider trading: material non-public information and breach of fiduciary duty.

(15:25) How difficult it is to consistently generate returns without some form of edge.

(16:26) The first insider tip—and the rationalizations that followed.

(19:03) The "fraud triangle": pressure, opportunity, and rationalization.

(22:16) Placing the first illegal trade—and feeling almost nothing.

(24:39) Peer validation and the normalization of wrongdoing.

(28:38) The 6:30 a.m. arrest and being approached by the FBI.

(31:43) Deciding to cooperate—and becoming "Tipper X."

(36:24) Learning to wear a wire and extract incriminating statements over multiple meetings.

(38:26) Inside Operation Perfect Hedge: 81 individuals charged, 32 cooperators.

(39:28) The chilling effect on hedge funds and the possible decline of illicit "edge."

(42:12) Being publicly unmasked as Tipper X and the personal cost to his family.

(44:02) Why ethical failures are incremental—not sudden transformations.

(45:11) The gap between academic ethics and real-world psychological pressure.

(46:57) The role mentorship could have played—and how culture shapes behavior.

(50:29) Tom's view on hedge funds for retail investors: high fees, limited liquidity, and questionable value.

(52:04) Ethical drift, rationalization, and warning signs to watch for.

(52:35) Redemption: Owning mistakes fully and learning to forgive yourself.

(55:02) Redefining success—relationships, honesty, and meaningful contribution.

Links From Today's Episode:

Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p

Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.
Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/

Rational Reminder on YouTube — https://www.youtube.com/channel/
Benjamin Felix — https://pwlcapital.com/our-team/

Benjamin on X — https://x.com/benjaminwfelix

Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/

Dan Bortolotti — https://pwlcapital.com/our-team/

Dan Bortolotti on LinkedIn — dan-bortolotti-8a482310

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)

In this episode of the Rational Reminder Podcast, we are joined by Theresa Ebden, Vice President of the Investor Office at the Ontario Securities Commission, for a deep dive into how regulators are thinking about modern investor risks—from AI-powered scams to finfluencers and the gamification of investing apps. Theresa explains how the OSC works to protect investors through policy, education, behavioral research, and direct engagement with the public, and why investor education is one of the most powerful tools regulators have.

Key Points From This Episode:

(0:01:55) Overview of the OSC and why its investor research and education work matters.

(5:42) What the Ontario Securities Commission does and its mandate to protect investors and capital markets.

(6:25) Inside the OSC Investor Office: policy, education and outreach, and the investor contact centre.

(9:28) How the Investor Office identifies priority issues using inquiry data, behavioral insights, and global collaboration.

(12:11) The nature of investor inquiries: fraud, crypto confusion, complaints, and recovery room scams.

(14:01) How contact-centre data feeds into education, outreach, and policy responses.

(16:07) Overview of GetSmarterAboutMoney.ca and its role in investor education.

(20:43) Major retail investor risks today: AI-enhanced scams, finfluencers, dark patterns, and gamification.

(24:43) What to do if you're impersonated by AI in scam advertisements.

(29:28) What a "finfluencer" is and the different categories they fall into.

(31:01) Research findings on how strongly finfluencers influence investor decisions.

(32:55) Why non-investors are especially vulnerable to finfluencer advice and social-media scams.

(36:11) How investors can evaluate online financial advice and check credentials.

(38:02) Regulatory challenges in overseeing finfluencers and online financial content.

(41:04) How AI magnifies traditional scams and why AI-enhanced fraud is more effective.

(43:42) Mitigation strategies: education, just-in-time warnings, and system-level tools.

(47:25) Relationship investment scams and why they are especially damaging.

(52:53) Research on gamification in investing apps and its effects on investor behavior.

(55:25) The Get Smarter About Trading simulator and how it demonstrates gamification effects.

(57:19) How gamification can be used positively to improve diversification and outcomes.

(58:16) Theresa's perspective on success and her focus on improving the individual investor experience.

Links From Today's Episode:

Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p

Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.
Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/

Rational Reminder on YouTube — https://www.youtube.com/channel/
Benjamin Felix — https://pwlcapital.com/our-team/

Benjamin on X — https://x.com/benjaminwfelix

Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/

Dan Bortolotti — https://pwlcapital.com/our-team/

Dan Bortolotti on LinkedIn — https://ca.linkedin.com/in/dan-bortolotti-8a482310

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)