The Cheat Code & Friends

What’s the real story behind funding a startup today? Greg Head, founder of Practical Founders, joins the hosts to break down the world of bootstrapping vs VC funding. From capital strategy to AI-driven growth, this episode digs into what actually works in today’s market. From chasing VC or building lean, this episode is packed with discussion on funding models, founder expectations, and the impact of AI on business strategies.

Chapters

00:00 Market Trends and Economic Challenges
02:47 Capital Allocation vs. Bootstrapping
06:12 The Global Landscape of Founders
08:52 Characteristics of Practical Founders
11:53 Growth Strategies and Metrics
14:51 Evaluating Great Companies
18:04 The Role of Founders in Company Success
21:11 Navigating Between VC and Bootstrap Models
28:26 The Evolving Landscape of Venture Capital
31:45 Navigating Funding Models and Founder Expectations
36:33 Understanding the Dynamics of Syndicated Deals
39:44 The Role of AI in Modern Business Strategies
54:22 Finding the Right Fit: Aligning Founders and Funders

References in the Show:

https://www.saastr.com/carta-38-of-bootstrapped-start-ups-have-solo-founders-but-only-17-of-vc-backed-ones-do-and-10-12-of-ones-that-ipo/ 

https://therecursive.com/tally-bootstrapped-success/

https://practicalfounders.com/ 

Quote of the Show:
“The practical founders I work with are adding AI incrementally and practically in useful ways into their product. They're not stopping everything, saying we're going to be AI-first. They're not just waving AI out there, but they're using it in their business to get more efficient, and faster. Then we're back to the choice of how fast do you want to grow and what do you want to do with those extra dollars?” - Greg Head 


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.

Game over.