Listen in as we talk with Craig Coppola, a seasoned investor, entrepreneur, and commercial real estate legend, to discuss the messy reality of startup investing. From assessing founder grit to navigating lean liquidity environments, Craig shares what makes a deal worth chasing (and what makes him walk away). We talk about the hard truths of entrepreneurship, why trusting the “jockey” matters more than the “horse,” and how the best investors build long-term success on discipline, culture, and conviction.

If you're raising capital, building a company, or considering your first investment, this episode shares what it takes to win and what pitfalls to avoid when betting on startups.

Chapters

00:00 Introduction and Team Dynamics

02:58 Craig's Journey into Investing

06:05 The Evolution of Investment Strategies

09:12 Navigating Deal Flow and Investment Decisions

11:47 The Importance of Cash Flow in Startups

15:04 Market Trends and Liquidity Challenges

22:35 Navigating Founder Commitments and Financial Strategies

23:48 Evaluating Deals: Red Flags and Founder Investment

25:53 The Challenges of Business Growth and Execution

28:41 Lessons from Experience: The Hard Truths of Startups

30:06 The Importance of Sales and Team Dynamics

32:09 Building a Culture of Execution and Learning

34:51 Transitioning from Founder-Led Sales to a Sales Team

39:15 Advice for Aspiring Investors: Finding the Right Path

References in the Show:

https://www.wsj.com/articles/angel-investing-isnt-what-it-used-to-be-e643c862

https://www.linkedin.com/posts/craigcoppola_c2voice-recenttransactions-officemarket-activity-7320929470763171840-Qv_K/?utm_source=share&utm_medium=member_desktop&rcm=ACoAABGQUe0BsV-UBJEAh7QOmp9oMj11PxcnemE

Quote of the Show:

“Entrepreneurial means you've got to make great business decisions. And so to me, you can negotiate a better deal if you're cashflow positive and you're telling them, I don't need the money. We have one of those right now where he's growing like crazy. He doesn't need the money. And it's like, if I take money, it's going to be for the right reason…This is what I want. When you look like a founder like that, I don't mind investing with somebody for the second time.” - Craig Coppola

Ways to Tune In:

• Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8
• Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190
• Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912
• YouTube: https://www.youtube.com/@CheatCodePodcast