Why the VC Hype Cycle Always Gets It Wrong | VC Roundtable | E2307

Why the VC Hype Cycle Always Gets It Wrong | VC Roundtable | E2307

Author: Jason Calacanis July 2, 2026 Duration: 1:14:10
This Week In Startups is made possible by: CLA - www.claconnect.com/withyou Northwest Registered Agent - www.northwestregisteredagent.com/twist Agree.com - www.agree.com Today's show: Forget the triple-triple-double-double-double; the new bar for startups hoping to raise venture capital has reached the stratosphere, though our venture panel is worried that startups are focusing too much on today's problems that may not become companies tomorrow. During a lively VC roundtable, Cowboy's Aileen Lee, Floodgate's Mike Maples, and Lerer Hippeau's Ben Lerer joined Alex to dig into exiting pre-AI startups, rising valuations, token spend, why they are keeping their funds small, and whether the government just tripped OpenAI and Anthropic! Guest Links: Aileen Lee https://x.com/aileenlee Cowboy VC https://cowboy.vc Mike Maples https://x.com/m2jr Floodgate https://www.floodgate.com Bene Lerer https://www.linkedin.com/in/benjlerer Lere Hippeau https://www.lererhippeau.com Timestamps: 0:00 Aileen Lee, Mike Maples, and Ben Lerer join the show 5:13 Venture liquidity returns: what SpaceX/Stripe distributions mean for LPs 9:13 Bending Spoons prices IPO at $29/share, roughly $18.4B valuation 10:31 Agree.com - Stop chasing invoices and automate your entire contract-to-cash stack. Go to https://agree.com and tell them Jason sent you to get 50% off for life! 12:09 "Companies get bought, not sold" — Ben on taking first offers seriously 17:41 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off! 19:34 Mutiny's burn-the-boats AI pivot with Jaleh Rezaei 20:19 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://www.northwestregisteredagent.com/twist 22:15 Mike's KeepSafe story: the "rule of 70" and profit-first companies 25:12 The new growth bar: 5x, 4x replaces triple-triple-double-double 28:55 Fund size is your strategy: why Floodgate and Lerer Hippeau stay small 30:11 CLA - Innovation takes balance. CLA's CPAs, consultants, and wealth advisors can help you get from startup to where you want to end up. Get started now at https://www.claconnect.com/withyou 37:39 The $100M Series A: Starcloud, General Intuition, Scale Cognition, Scout AI 40:35 King-making rounds and why mega-seeds destroy optionality 54:11 Open-weight models: the GLM-5.2 moment and going model-agnostic 55:30 Why fine-tuning open models is a treadmill, with Cursor/Kimi as an example 1:03:28 Grading the Trump administration on Mythos and Fable 1:06:33 Rising anti-AI sentiment, the wealth gap, and lessons from social media 1:11:43 Raising kids in the post-intelligence era 1:12:35 Where to find the panel and what each firm is investing in Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
Author: Language: en-us Episodes: 50

This Week in Startups
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