Gregory on Building and Selling 12 Profitable Startups—And What Most Founders Get Wrong

What if building a billion-dollar startup wasn’t just about funding rounds—but about timing, discipline, and knowing when to exit?

In this episode of the Exitfund Podcast, we talk with Gregory, a serial entrepreneur, investor, and author who has built and sold 12 companies and backed startups that actually exit. Gregory shares why most founders fail, what investors often get wrong, and how impact and profitability can go hand in hand.

We dive deep into:

• The 7-stage startup lifecycle—and why skipping steps kills companies

• How to spot market disruptions and time contractions for massive upside

• Why founder discipline matters more than flashy pitch decks

• The real role of AI in business and government—beyond the hype

• Lessons from building profitable businesses across industries and geographies

• His sharp takes on Steve Jobs, Elon Musk, politics, and power

Whether you're an early-stage founder, investor, or startup advisor, this conversation will sharpen how you think about building for scale—and for exit. And if you're seeking mentorship and funding to grow your venture, connect with us at Exitfund.com.

Don’t just chase valuation—build to last, and know when to sell.