Running Toward Risk: Lewis Schiff on the Mindset of True Entrepreneurs
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“Most people run from risk. Entrepreneurs run toward it.”
That’s how Lewis Schiff—author, entrepreneur, and founder of Birthing of Giants—describes the DNA of vision-driven business builders. In this episode of Constructive Interference, host Rufus Cressend sits down with Lewis to unpack what separates entrepreneurs from everyone else—and how we can build smarter, not just harder.
The Entrepreneur’s “Different Equipment”
Lewis opens with a striking analogy: police officers and entrepreneurs are both trained to move toward danger, not away from it.
For a cop, it’s a bulletproof vest and tactical gear.
For an entrepreneur, it’s knowledge—finance, sales, leadership, and resilience.
It’s the same instinct expressed differently: the willingness to confront uncertainty, to turn chaos into order, and risk into opportunity.
From Hard Knocks to Smart Leverage
Both Rufus and Lewis admit they once glorified the “school of hard knocks”—the idea that you have to suffer to succeed. But as Lewis points out, that mindset often wastes energy that could be used for innovation and growth.
“You can learn what you don’t know, and then bring all that risk orientation to do the new.”
The better path? Learn from those who’ve already been there. Surround yourself with mentors, peers, and coaches who can shorten your learning curve—and save you from expensive mistakes.
The Power (and Price) of Failure
Lewis has failed at least twenty times, and he’s proud of it.
Why? Because failure, he says, is the best teacher there is.
Entrepreneurs, he argues, feel the sting of failure just like anyone else—but they choose to get back up. They turn that pain into progress. Rufus adds that the key is not to get stuck in a victim mindset: “We either win, or we learn.”
Understanding Capitalism as a Skill
One of Lewis’s biggest missions today is helping entrepreneurs understand capital—how it moves, multiplies, and shapes the playing field.
Too many founders, he warns, build great companies but sell them short because they don’t fully grasp how valuation and deal structures work.
That’s why he’s expanding Birthing of Giants into regional cohorts across the U.S.—so entrepreneurs can learn to become better capitalists, together.
His advice:
Learn how money flows.
Build founder-friendly partnerships.
Stop being “a practicing capitalist who doesn’t understand capitalism.”
Visionaries Who Make the World Better
Only 2–3% of people are wired to take big risks, and Lewis believes that small group is essential to progress. Whether it’s inventing new tech or reshaping company culture, entrepreneurs move society forward.
But the mission isn’t just personal success—it’s about impact. As Lewis puts it:
“Our contribution to society is successfully innovating—bringing something new to market that makes the world a better place.”
Key Takeaways
Run toward risk, not away from it. Courage is teachable—and trainable.
Failure is data. Treat every setback as a learning cycle, not an identity.
Stop romanticizing burnout. Replace “grind” with growth through mentorship.
Understand capital. Learn how to make your money work as hard as you do.
Find your tribe. Entrepreneurship is lonely—don’t do it alone.
🎧 Listen to the full conversation: YouTube | Spotify | Apple Podcasts | Amazon Music | iHeart Radio | Audible
💬 Guest: Lewis Schiff
📍 Host: Rufus Cressend, Constructive Interference
