{"type":"rich","version":"1.0","provider_name":"Transistor","provider_url":"https://transistor.fm","author_name":"The Cheat Code & Friends","title":"Liquidity, Hustle and Trust- Season 4: Episode # 69","html":"<iframe width=\"100%\" height=\"180\" frameborder=\"no\" scrolling=\"no\" seamless src=\"https://share.transistor.fm/e/d70830c7\"></iframe>","width":"100%","height":180,"duration":2399,"description":"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.\n\nIf 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.\n\nChapters\n00:00 Introduction and Team Dynamics\n02:58 Craig's Journey into Investing\n06:05 The Evolution of Investment Strategies\n09:12 Navigating Deal Flow and Investment Decisions\n11:47 The Importance of Cash Flow in Startups\n15:04 Market Trends and Liquidity Challenges\n22:35 Navigating Founder Commitments and Financial Strategies\n23:48 Evaluating Deals: Red Flags and Founder Investment\n25:53 The Challenges of Business Growth and Execution\n28:41 Lessons from Experience: The Hard Truths of Startups\n30:06 The Importance of Sales and Team Dynamics\n32:09 Building a Culture of Execution and Learning\n34:51 Transitioning from Founder-Led Sales to a Sales Team\n39:15 Advice for Aspiring Investors: Finding the Right Path\n\n\nReferences in the Show:\nhttps://www.wsj.com/articles/angel-investing-isnt-what-it-used-to-be-e643c862\n\nhttps://www.linkedin.com/posts/craigcoppola_c2voice-recenttransactions-officemarket-activity-7320929470763171840-Qv_K/?utm_source=share&utm_medium=member_desktop&rcm=ACoAABGQUe0BsV-UBJEAh7QOmp9oMj11PxcnemE  \n\nQuote of the Show:\n“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....","thumbnail_url":"https://img.transistorcdn.com/AoPG3flkss3fsfc-m7ywyJ39XTunoIaKRubQ7PAkerg/rs:fill:0:0:1/w:400/h:400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9lNWVl/YWZiNDRlMGVlYjVi/MmE4MzhjNWQ1ZWMz/NDZmMC5qcGc.webp","thumbnail_width":300,"thumbnail_height":300}