The Dark Side of Entrepreneurship: The Truth About Wealth, Growth & Greed

In this episode, we’re sitting inside Society Hill Hotel, reflecting on the experience of staying in the very place we run. The conversation quickly turns to the entrepreneurial curse—that constant drive for more, better, bigger. We unpack why business owners are often their own worst critics, the struggle of chasing perfection, and the fine line between focus and distraction.

From glamping franchises to fusion restaurants, we explore how staying focused (or failing to) can make or break a business. Plus, we share personal stories of past ventures, the lessons we’ve learned, and the defining metric of success that’s driving us forward now.

If you’ve ever wondered when is enough, enough?—this one’s for you.

“Nobody would trade places with Warren Buffett right now. He’d trade it all for more time.”

What You’ll Learn:

✅ Why entrepreneurs are wired to focus on flaws instead of wins 

✅ The hidden dangers of expanding too fast (or in the wrong direction) 

✅  How Away, Allbirds, and  Warby Parker struggled with focus 

✅  The truth about money and happiness—what successful people say vs. feel 

✅ Why defining your success is the hardest part

Links & Resources:

📌 Follow us on Instagram: @findingbrotherlylove 

📌 Books mentioned: Never Enough by Andrew Wilkinson & The Five Types of Wealth by Sahil Bloom