Jan 30, 2017 · 25m · 20vc
20VC: How 50% Of VCs Hurt Entrepreneurs, How To Build A Relationship Of Trust With Your VC and How Entrepreneurs Can Detect VC BS with Jason Mendelson, Co-Founder @ Foundry Group
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews Jason Mendelson, co-founder of Foundry Group, discussing venture capital dynamics, founder transparency, regional tech ecosystems, and investment strategies across market cycles. Mendelson offers candid advice on spotting predatory investor behavior, structuring productive board meetings, and evaluating early-stage valuation realities versus long-term partnership value.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 39.5% of the talking time here. How this is scored →
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Jason aggressively criticizes his own industry, stating that half of VC firms actively harm entrepreneurs and expressing a lack of respect for half the VCs he sits on boards with.
Hardest push from Harry ▶ 17:14 Host counters on price flexibilityHarry resists Jason's strict approach to valuation by bringing up Fred Wilson's principle that price should not prevent doing a deal with a great company.
Biggest teaching moment ▶ 15:22 The failure culture requirement for tech hubsJason provides an insightful lesson on ecosystem development, demonstrating how Detroit failed to thrive despite having capital and talent because it lacked Silicon Valley's acceptance of entrepreneurial failure.
Harry holds his own ▶ 17:14 Harry invokes Fred Wilson on deal dynamicsHarry demonstrates his deep grasp of venture capital philosophy by citing explicit advice from Howard Lindzon and Fred Wilson to test Jason's investment rules.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Jason Mendelson's Path to Venture Capital | 3 | 1 | 1 | 1 | Harry asks warm opening questions about Jason's transition from general counsel to VC, passing along a specific question from Brad Feld. Jason candidly shares his path and an anecdote about making a legal blunder that signaled his full transition to investing. | |
| Transparency, VC Misalignment, and Detecting VC BS | 3 | 4 | 5 | 2 | Harry prompts Jason on how to detect venture capital marketing jargon and BS. Jason pulls no punches, estimating 50 percent of VCs hurt entrepreneurs and calling out fake transparency and superficial firm marketing. | |
| Cultivating Trust and Managing Board Meeting Dynamics | 4 | 3 | 2 | 1 | Harry references specific founder practices, like Sphero sending board materials in advance to keep meetings strategic. Jason agrees strongly, detailing how poor board dynamics make him spell board as B-O-R-E-D. | |
| Regional Tech Ecosystems and Building Outside Silicon Valley | 3 | 4 | 3 | 1 | Harry asks about building startups outside traditional coastal hubs and the essential pillars of an ecosystem. Jason mocks coastal arrogance and explains the critical role of a failure-tolerant culture using Detroit as a counterexample. | |
| Investment Strategy, Deal Competition, and Valuation Realities | 5 | 3 | 3 | 4 | Harry challenges Jason on valuation sensitivity by citing a insight from Howard Lindzon and Fred Wilson regarding price flexibility. Jason pushes back gently, distinguishing between early and late stage pricing games and holding his firm's disciplined stance. | |
| Narcissism in Tech Culture and Investing Through Market Cycles | 3 | 3 | 3 | 1 | Harry leads a rapid-fire section covering tech culture narcissism, market cycles, favorite books, and personal anecdotes. Jason observes that during downturns, opportunistic VCs disappear while true entrepreneurs stay the course. |