Will Glass founder of Ostrich, left behind a comfortable corporate job—without a fully-baked plan—to chase an idea that everyone said would be “too risky.” After burning through money building features nobody needed and trudging through multiple pivots—including a foray into the NIL college sports market—Will finally discovered how to make Ostrich a legitimately impactful product.In this episode, you’ll learn: • How to avoid the pitfalls that cause most early-stage founders to waste cash• When to pivot vs. when to double down on your original vision• The secret to finding a real customer base—before money and time run out• Why sometimes “doing the unscalable” is the key to long-term growth• And how to separate your self-worth from the rollercoaster of startup lifeIf you want a refreshingly candid look at startup life—beyond the highlight reels—stick around. Will’s story proves you can stumble through chaos and still find your footing. Enjoy the conversation!
Connect with Will: https://www.linkedin.com/in/williampglass3/
Chapter:00:00 Untold Struggles
02:28 The Birth of Ostrich
03:00 Pivots & Financial Challenges
12:14 Pitching & Failures
15:32 Accelerators and Mentorship
22:54 Building Trust with Investors
26:20 The Cockroach Strategy
27:29 Deciding Whether to Raise Capital
29:10 Mindset Shifts
30:30 Navigating the NIL Space
35:41 Credit Unions
40:18 Importance of Focus
41:49 Doing the Unscalable
