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:
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:
What is The Cheat Code & Friends?
Serial entrepreneurs and operators Justin Gray, Josh Wagner & Sean Kester combine decades of B2B and GTM expertise with unwavering honesty to unpack the latest news (fake or otherwise) on The Cheat Code & Friends Podcast. Combined with a rotating guest list of founders, practitioners and investors, the no-nonsense forum gathers fortnightly, holding court to translate headlines into reality and discuss the impact for early-stage businesses. The Cheat Code is just that, the trusted folks we look to for advice and insight, and we hope to bring the same to you.