The Khanversation with Imran Khan

In this episode of The Khanversation with Imran Khan, Imran speaks with Jason Wilk, the founder and CEO of Dave, a fintech company redefining neobanking. Jason recounts his early entrepreneurial pursuits, from selling golf gear online to launching venture-backed startups. He shares the origin story behind Dave, the unique strategy of micro-lending without credit checks, and how he leveraged AI and data to build a profitable digital bank. Jason also reflects on going public, overcoming a dramatic stock collapse, and his plans to expand into new credit verticals. Tune in to hear how resilience and focus powered one of the most impressive comebacks in the fintech world.

In this episode of The Khanversation with Imran Khan, Imransits down with Tom Lee, founder of Fundstrat and a veteran strategist with decades of experience across market cycles. Tom shares his top five learnings from 30+ years in finance, from understanding the collective intelligence of markets to avoiding overreliance on P/E ratios. He discusses how execution, asset turnover, and structural themes drive stock performance, and why emotional discipline matters in investing. The conversation then dives into Tom’s early conviction in Bitcoin, its rise as a digital store of value, andwhere it could go in the next decade. Tom also breaks down today’s macroeconomic environment and explains why he believes the market has largely priced in risk.

In this episode of The Khanversation with Imran Khan, Imransits down with Michael Strain, professor at Georgetown University and senior fellow at the American Enterprise Institute, for a deep conversation on U.S. trade policy. Together, they explore the implications of tariffs, how global manufacturing and employment trends have evolved, and why common narratives around outsourcing and trade deficits may miss the mark. Michael challenges widely held beliefs on American manufacturing decline, discusses the politicalversus economic weight of trade debates, and offers perspective on strategic reshoring of critical industries. The two also probe market reactions, including bond yields and currency movements, and the potential fallout of ongoing trade tensions.

In this episode of The Khanversation with Imran Khan, Imran speaks with Andrew Dudum, founder and CEO of Hims & Hers Health. Andrew shares the journey from his early entrepreneurial days—dropping out of Wharton and co-founding Atomic—to launching one of the fastest-growing digital health companies. He explains how a regulatory shift opened the doors to virtual care, the tech stack powering scalable patient outcomes, and how Hims & Hers is redefining access and quality across healthcare. Andrew also digs into the company's bold vision, how AI will reshape the patient experience, and why he’s building for a 20-year horizon____________________________________________________________(00:00:00) Andrew's early background and journey to entrepreneurship(00:01:34) Identifying the consumer healthcare gap and launching Hims & Hers(00:03:08) Dropping out of Wharton and shifting from music to business(00:06:03) Early career at Talkbox and lessons from its acquisition(00:08:54) Learning the importance of focus and conviction(00:10:42) Regulatory trigger that sparked the digital health opportunity(00:13:05) Naming Hims & Hers and building a brand around inclusivity(00:14:28) Raising early capital and articulating the long-term vision(00:16:00) Using data and tech to improve patient outcomes(00:20:20) Delivering personalized care through technology and scale(00:22:06) What drives Hims & Hers' rapid growth(00:25:09) Strategy for scaling from 2 to 10+ million members[00:28:06] Deciding which care categories to launch next(00:30:53) International expansion plans and timing(00:33:14) Weight loss market strategy and debunking GLP-1 hype(00:36:47) Comparing the platform to Netflix for healthcare(00:38:06) Generic medications and structural problems in access(00:39:49) Thoughts on competition and market dynamics(00:42:36) How AI will transform diagnostics and provider tools(00:45:33) Operating as a fully remote company and hiring strategy(00:49:15) Talent scaling and performance management philosophy(00:51:48) What’s misunderstood about Hims & Hers and Andrew’s long-term visionLinks:Imran Khan on X: https://x.com/dottkhanImran Khan on LinkedIn: https://www.linkedin.com/in/dotkhan Andrew Dudum on LinkedIn: https://www.linkedin.com/in/andrewdudumHims & Hers: https://www.hims.com/