Imagine accepting a job where you’re guaranteed no paycheck, asked to put up all your savings, and expected to outperform everyone around you—without the certainty of success. On paper, it’s a reckless gamble. Yet this is exactly what entrepreneurship demands.
And yet, framed differently: What if that same job promised no limits to your growth, allowed you to answer only to customers, and gave you the power to create meaningful value—for others and for yourself? Suddenly, the proposition doesn’t sound so crazy. For some, this sounds like a disaster. For others, like the author of this deeply experienced reflection, it’s a calling.
After three decades in the trenches—as a surgeon, a co-founder, and an investor—this seasoned entrepreneur shares four critical lessons. They don’t come from books or case studies. They come from courtrooms, boardrooms, and high-stakes operating rooms. If you’re building a company with long-term ambitions, these are lessons you can’t afford to overlook.
1. Tension Is Inevitable—Learn to Work Through It
Success doesn’t come without friction. That friction rarely comes from business models or market conditions—it comes from people. Customers, employees, and especially cofounders.
In fact, according to Harvard Business School professor Noam Wasserman, 65% of high-potential startups fail because of cofounder conflict. This is no hypothetical. Just five months into launching a boutique hospital with 12 other physicians, the author found himself in court over a dispute that nearly derailed the business.
The takeaway? Don’t assume alignment just because you share a mission. Structure your business to protect your long-term interests. Learn to operate in discomfort. That’s not a flaw—it’s a necessary condition for breakthrough.
2. Ask the Right Questions—Then Listen
A great idea isn’t enough. Execution depends on discovery, and discovery starts with asking better questions. Entrepreneurs often fall into the trap of validating their assumptions, instead of challenging them.
Sustainable businesses are built not by people who have all the answers, but by those who know how to listen, synthesize, and adapt.
Pro tip: Be skeptical of your own certainty. The best founders treat feedback like gold and curate their circles intentionally—knowing that insight compounds when egos step aside.
3. Treat Every Opportunity Like It Matters
Most startups don’t survive past year five. Even with funding, vision, and talent, the odds aren’t generous. That makes every opportunity a potential inflection point.
But opportunity doesn’t always look like capital or press. It might show up as a conversation, a referral, or a delayed “yes.” The smartest founders know that relationship capital is often more durable than financial capital—and often more valuable.
Key habit: Create value before you ask for it. Build relationships patiently. Save your asks for when it truly matters.
4. Never Let Up Before the Final Whistle
Business isn’t won by halftime. A few deals, a good year, or a round of funding may feel like momentum—but they’re not the finish line.
The analogy to professional sports is apt. A game isn’t over until it’s over. Neither is a business. The founders who exit well are those who maintained intensity through the mundane, the messy, and the middle.
Success isn’t just a destination—it’s the consistent, exhausting effort that precedes it. Even when things go right, keep your head down and your foot on the gas.
Final Thought:
Three decades in, the author acknowledges one regret: not knowing all this from the beginning. But you can. These aren’t romanticized ideals—they’re practical foundations.
Entrepreneurship isn’t a sprint to a liquidity event. It’s a lifelong process of refining your instincts, your people skills, your vision—and your patience.
So here’s a question worth sitting with: