The Intuition Advantage: Using Gut and Grit to Bet Big and Bounce Back w/ Tom Williams of ELEASE

Summary

From detailing boats at 13 to launching a pioneering online leasing platform, Tom Williams’ entrepreneurial journey is marked by grit, resilience, and hard-won wisdom. In this deeply candid conversation, Tom recounts his early hustle growing up in a resort town, launching his first lending company in San Francisco at age 25, and learning the ropes of business by trial, error, and sheer persistence. Despite early challenges—like living in his office to save costs—Tom pressed forward, eventually raising millions in venture capital and confronting the fallout of a market crash that nearly destroyed his business.

What followed was a pivotal reinvention. After his VC-backed venture collapsed, Tom bought a coveted domain name and rebooted his company on his own terms. With nothing but servers crammed into his apartment, he rebranded and relaunched his business—profitable within two weeks. Tom shares the emotional toll of that failure and rebirth, emphasizing how it shaped his fiercely value-driven approach and his deep commitment to culture, character, and customer-centered leadership.

Now at the helm of a thriving private lending business with over two decades of operation, Tom reflects on what he’s learned about building teams, maintaining integrity, and staying financially grounded. He talks about hiring for grit, the importance of knowing when to ask for help, and how character—more than capital—can be the strongest moat for a founder navigating uncertain waters.

Takeaways

1. Start before you’re ready. Tom launched his first company at 25, recognizing his aptitude and passion before he fully understood the risks.
2. Co-founder dynamics matter. He initially planned to start with a partner, but differing life stages made solo founding the better path.
3. Resilience pays off. Tom lived in his office for six months to conserve funds and stay committed to his vision.
4. Being a broker can be a launchpad. Without capital to lend, Tom positioned himself as a conduit between banks and clients, building trust and traction.
5. Adapt business models quickly. His biggest pivot—from a VC-backed marketplace to a lean, bootstrapped lending platform—came out of necessity but led to long-term success.
6. Hire for culture fit. Tom emphasizes hiring gritty people who can “take a punch,” prioritizing character and teachability over experience.
7. Keep customer needs front and center. Every meeting ends with “what would the customer think of that?”—a mantra that guides decision-making.
8. Beware of letting investors change your DNA. Taking money can bring value but also pressure to pursue unsustainable visions.
9. Have a backpedal plan. Founders should understand what happens if growth projections fall short—many don’t.
10. Ask for help. One of Tom’s biggest regrets is not seeking support during lonely, difficult chapters in his journey.

Chapters

• [00:01] Tom’s Entrepreneurial Origins
  • Tom shares how growing up in a seasonal town and starting a boat detailing business at 13 sparked his entrepreneurial instincts.
• [01:30] Founding Solo After a Missed Partnership
  • Originally planning to start with a co-founder, Tom explains how personal circumstances led him to launch alone.
• [03:57] Early Surprises and Office Living
  • From unexpected expenses to living in his office, Tom discusses the gritty realities of launching his first business.
• [05:24] Starting as a Broker Without Capital
  • He describes how acting as a broker enabled him to operate in the lending space without an initial balance sheet.
• [06:34] Why Ignorance Was a Superpower
  • Tom reflects on how not knowing everything actually helped him take bold steps early on.
• [08:07] Funding the Business with $5,000
  • Tom shares how he borrowed a small amount from his father to cover early expenses and survive.
• [09:32] Finding Early Customers Through Cold Calling
  • Tom discusses early customer acquisition strategies, including targeting previous borrowers.
• [10:44] Vendor Relationships and Internet Infrastructure
  • He explains how vendor partnerships helped drive business during the internet boom of the late 90s.
• [13:33] The First Key Hires
  • Tom outlines his hiring strategy, beginning with sales and support roles that doubled deal flow.
• [17:19] Differentiation Through Character and Service
  • He talks about how character, honesty, and domain knowledge set his company apart in a nascent market.
• [22:27] The Big Bet: Raising VC and Launching LeaseExchange
  • Tom recalls raising $3M and launching a new venture—only to have the market crash days after launch.
• [33:02] Personal Fallout and Gritty Rebuild
  • After layoffs and personal loss, Tom rebrands as E-Lease and runs the business from servers in his apartment.
• [35:35] Profitability in Two Weeks with a Lean Model
  • He explains how retooling the business for margin (not volume) made it profitable almost instantly.
• [43:39] Moving to Florida for Culture and Cost
  • Tom shares why he moved the company from San Francisco to Florida to prioritize culture fit and affordability.
• [48:41] Lending Advice and Planning for the Worst
  • He emphasizes planning for setbacks and knowing whether you’re building for exit or lifestyle.
• [52:18] Gut Checks and Core Values
  • Tom explains how staying true to his gut and values has repeatedly guided the right decisions.
• [54:30] Questions Founders Ask—and Should Ask
  • He reveals that many ask how he did it, but few ask what would happen if it hadn’t worked.
• [60:02] If He Could Do It Over
  • Tom would raise more capital earlier and take more risks—advice rooted in hindsight and wisdom.
• [62:50] Two Anchoring Texts
  • Tom shares how “The Man in the Glass” and “The Man in the Arena” keep him humble, accountable, and inspired.