He Inherited a 79-Year-Old Business… and Lost 70% of It

Tom Sosnoff on Risk, Trading, and Building Billion-Dollar Companies

Tom Sosnoff is the co-founder of thinkorswim and tastytrade, two of the most influential trading platforms in modern finance. Before building billion-dollar companies, Tom spent nearly 20 years as an options market maker in the pits of the Chicago Board Options Exchange. In this conversation, he sits down with David Heacock to discuss how trading rewired the way he thinks about risk, entrepreneurship, decision-making, and wealth creation. They cover: - Why most people completely misunderstand risk - The psychology of great traders and entrepreneurs - Lessons from the 1987 crash and the 2008 financial crisis - Building thinkorswim from scratch after leaving the trading floor - Why thinkorswim was profitable from month one - How tastytrade used content as a competitive advantage long before creator businesses became mainstream - Why Tom believes content and attention are now the real moat in finance - His views on retirement, legacy, and building companies late into life - Why he hates real estate investing - How options trading changes the speed and quality of decision-making - Why young entrepreneurs should take far more risk than they think - His new AI-driven company, Lost Dog, focused on career optimization and wealth inequality Tom also shares stories from the early days of Chicago trading pits, competing against Interactive Brokers, selling billion-dollar companies, making 50 trades before breakfast, and why he still wakes up every day obsessed with building. If you enjoy conversations about markets, entrepreneurship, risk-taking, investing, and building enduring businesses, this episode is for you.

The $14M Pool Fence Business Replacing SaaS With AI

Eric Leppin took over Lifesaver Pool Fence at 21 and grew it from under $1M to over $14M a year. In this episode, we talk about franchising, dealer economics, building a custom CRM with AI, and why the old “best practices” for running a business may be changing faster than most owners realize. This is a conversation about resilience, first-principles thinking, and how niche businesses can use AI to build systems the big software companies never will.

How a Doctor Built an 8-Figure Healthcare Logistics Business With No Investors

Amit was a frontline physician working 80-hour weeks during COVID when he realized something most healthcare systems still hadn’t figured out: Getting medication to patients is a logistics problem. What started as a simple medication reminder app evolved into PHOX Health — an 8-figure healthcare logistics company helping hospitals and pharmacies deliver everything from chemotherapy drugs to specialty medications directly to patients. In this episode, we break down how Amit bootstrapped the company with no investors, how they built a nationwide delivery network with an incredibly lean team, and why controlling the customer experience matters more than software alone. We also dive deep into: * Building “boring” businesses in healthcare * Why logistics is harder than software * The risks of scaling too many things at once * AI, automation, and why physical businesses still matter * Contractor vs employee delivery models * The hidden economics of medical delivery * How great customer experience becomes the moat This is one of the best examples I’ve seen of combining real-world operations with technology to solve a massive problem. If you want a front-row seat to how real operators build valuable businesses from scratch, this episode is for you.

He Inherited a 79-Year-Old Business… and Lost 70% of It

Clark Dane inherited a 79-year-old American manufacturing company and immediately watched it lose 70% of its revenue. Most people would have folded. Instead, Clark kept the business alive, rebuilt the customer base, and shifted from an old distributor/dealer model toward direct-to-consumer and commercial rental channels. But after sitting down with him, I realized the biggest opportunity was not just operational. It was mindset. Clark is sitting on a legacy American-made brand with real manufacturing capacity, a durable product, and a massive amount of low-hanging fruit in e-commerce, Amazon, Home Depot, and direct-to-consumer marketing. In this episode, we talk through the financial reality of running a small manufacturing company, why depreciation and equipment planning matter, how legacy distribution models create customer friction, and why building a modern brand requires the owner to become the chief evangelist. Clark is running a million-dollar company today. But the real question is whether he can start thinking like the owner of a much bigger one.

I Spent $200K on His Playbook. You're Getting It for $0

Eric Villa helped grow some of the biggest YouTube channels in the world — including MKBHD’s behind-the-scenes channel, The Studio — and then helped take my channel from struggling for views to millions of views in a matter of weeks. In this episode of Boring Money, Eric breaks down how YouTube actually works today: why ideas matter more than consistency, why most personal brand advice is outdated, how to package boring business ideas so people actually click, and why one video can still change everything. We also talk about the future of media, AI’s role in content, why wealthy founders are suddenly building personal brands, how boring businesses should think about social media, and what it really takes to build a channel that lasts. This is a behind-the-scenes look at the strategy, psychology, and creative process behind building attention in a winner-take-all media world.