How Real-World Experience Helps Founders Spot Market Gaps

In episode 153 of Startup Success, Kate Adams talks with Cortney Woodruff, co-founder and CEO of Assemble and an angel investor. Assemble bridges the gap between college and industry by bringing courses shaped by leading industry professionals to students beyond elite universities, including HBCUs and community colleges. One course reached 18,000 students in its first 30 days. Cortney built his first startup out of a hostel and a garage in San Francisco, and co-founded Assemble with Cortez Bryant, Lil Wayne's longtime manager. He shares how real-world experience helps founders spot what others miss, what he's learned from sitting on both sides of the venture table, and why patience matters as much as speed. Key takeaways: How real-world experience helps founders spot market gaps others overlook How founders can stand out without traditional networks or pedigrees How one Assemble course reached 18,000 students in 30 days What happened when the founding partner of a $4B VC firm asked, "What's an HBCU?" Whether being an angel investor makes you a better founder Cortney's advice to founders: speed and execution win, but remember the tortoise and the hare It's a candid conversation about building something meaningful when the traditional playbook wasn't built for you. 🎧 Listen to Startup Success wherever you get your podcasts! Startup Success is produced by Burkland Associates, which provides fractional CFO, accounting, payroll, and tax services for venture-backed startups. Learn more: https://burklandassociates.com/ Assemble: https://www.assemble.fyi/ Cortney on LinkedIn:   / cortney-woodruff-7182222b   Follow us:   / burkland-associates     / burklandassoc     / burklandassoc   0:00 Introduction 0:18 Meet Cortney Woodruff, Founder and Angel Investor 1:03 From Jackson, Mississippi to a Top Business School 2:40 How to Seize an Opportunity With Almost No Notice 4:32 Building a Startup From a Hostel and a Garage 6:19 The "Laying Bricks" Approach to Building Something Hard 7:26 The Problem Assemble Solves 9:44 Relevancy and Accessibility: Assemble's Two Pillars 11:38 How One Course Reached 18,000 Students in 30 Days 15:04 Building What You Wish You'd Had 17:54 When a $4B VC Firm Didn't Know What an HBCU Was 19:31 Does Being an Angel Investor Make You a Better Founder? 22:40 The Hardest Part of Being an Operator 25:26 Advice for Founders: Patience, Speed, and the Tortoise and the Hare 27:59 Where to Learn More About Assemble #StartupSuccess #EdTech #AngelInvesting #Founders