Drew Houston
15 statements across 4 episodes · 2 bullish · 2 bearish · 4 people on the record · first statement Aug 13, 2018 by Jeff Fagnan · said 54 times in 32 episodes since 2016 · across every show →
On the record as a speaker too: Drew Houston's record, appearances and statements → this page counts the times other people say the name.
Mentions by year
brought up most by Jeff Fagnan (9), Harry Stebbings (9), Jason Lemkin (6), Jeff Lawson (5), Dharmesh Shah (4), Todd Jackson (2), Ted Wang (2), Sujay Jaswa (2)
tap a year for its mentions
2026 4 mentions in 3 episodes 1 per episode
- Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
- OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
- Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
- every mention in 2026, scene by scene →
2025 9 mentions in 5 episodes 2 per episode
- OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
- Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
- OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
- General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
- Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
- every mention in 2025, scene by scene →
2024 4 mentions in 4 episodes 1 per episode
- Michael Eisenberg: How China Could Overtake the US in the AI Race | E1167 · 20VC with Harry Stebbings
- Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
- Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
- Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
- every mention in 2024, scene by scene →
2023 2 mentions in 2 episodes 1 per episode
2022 10 mentions in 7 episodes 1 per episode
- HubSpot Founder Dharmesh Shah: The Ultimate Guide to Company Culture | E896 · 20VC with Harry Stebbings
- Hadi Partovi: How I Became an Advisor to Mark Zuckerberg; Lessons from Steve Ballmer | 20VC #961 · 20VC with Harry Stebbings
- Ben Chestnut: Why I Sold MailChimp; How My Kids Found Out I Was a Billionaire | E959 · 20VC with Harry Stebbings
- Jeffrey Katzenberg & Sujay Jaswa: Takeaways from Dreamworks; What happened with Quibi? | 20VC #952 · 20VC with Harry Stebbings
- 20VC: Why Operating Experience Becomes Irrelevant Fast and Operators Often Give Bad Advice to Founders, Is Silicon Valley Really Dead? Are Gen Z the Most Entitled Employees? What Will Happen to a Generation of Pre-PMF Companies with $50M in the Bank with
- Sonali De Rycker | How I Became a Partner at Accel; Type 1 vs. Type 2 Mistakes | 20VC #902 · 20VC with Harry Stebbings
- 20VC: How I Lost a $125M Deal with Yahoo by Being Too Honest, The M&A Meeting with Steve Jobs That Did Not Go Well and How U2's Bono Saved The Day For One Tech Startup with Ali Partovi, CEO @ Neo
- every mention in 2022, scene by scene →
2021 1 mention in 1 episode
2020 6 mentions in 3 episodes 2 per episode
- 20VC: Lessons From Working with Bill Gates, How To Lead Without Authority and The Difference Between Leadership and Management & How Fundraising Changes In A COVID World with Quentin Clark, Managing Director @ General Catalyst
- Breaking News: Meet First Round Capital's Newest Partner, How To Approach Generational Transition as a Venture Firm & The Dangers of Attribution In Venture
- 20VC: 8VC's Joe Lonsdale on How To Foster Contrarian Thinking Within Venture Partnerships, Why The Best VCs Are Company Builders & Why It Is Not Possible To Build Multi-Billion Dollar Companies and Have Worklife Balance
- every mention in 2020, scene by scene →
2019 2 mentions in 2 episodes 1 per episode
- 20VC: Why Portfolio Construction Is Inefficient, Why The Only Thing That Matters In Venture Is Pricing & The Future of Venture; Bundled or Unbundled with Zach Coelius
- 20VC: Y Combinator's New President, Geoff Ralston on The Single Most Important Perspective An Investor Can Provide A Founder, The Biggest Lessons From Working Alongside Paul Graham & Why You Will Lose As An Investor If You "Profile Invest"
- every mention in 2019, scene by scene →
2018 12 mentions in 3 episodes 4 per episode
- 20VC: Why Partners Are There To Save Each Other From Themselves, Why Effective Reserve Allocation Is The Hardest Question In Venture & What Makes The Truly Special Board Members with Jeff Fagnan, Founding Partner @ Accomplice
- 20VC: A Framework For Approaching Risk and How It Affects Portfolio Construction | Lessons and Advice From Working with Dropbox's Drew Houston | Why Being A Learning Animal Is The Most Important Factor For Success with Ted Wang, Partner @ Cowboy Ventures
- 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
- every mention in 2018, scene by scene →
2016 4 mentions in 2 episodes 2 per episode
- 20VC: Index's Ilya Fushman on The Key Lessons From Scaling Dropbox To 400m Users, Is Excessive Amounts Of Capital Driving Valuations Too High In The Valley & Why Venture Is Like Being On A Swim Team Not A Soccer Team
- Uber's First Investor, First Round Capital's Rob Hayes on How The Deal Of The Decade Originated and Why Product Orientated VC Is The Future
- every mention in 2016, scene by scene →
Everything said about Drew Houston, oldest first
Aug 13, 2018 bullish
Jun 13, 2022
Dharmesh Shah missed early Dropbox investment due to mutual friendship hesitations
“Dropbox was one, and it was a weird story. And it was a miss because Drew and I were already friends. I knew him before he started Dropbox. Talked to him out of the prior startup he was going to do. We would meet regularly. He's another MIT guy. And it was a m…”
Oct 18, 2022 positive
Drew Houston: Enneagram is like Myers-Briggs, but actually useful
“And then I'd say the best exercise I've done on this dimension is learning about the Enneagram. Which are for those not familiar is it's kind of, you probably heard of Myers-Briggs or different personality typing systems. I think of the Enneagram is like it's …”
Oct 18, 2022
Drew Houston: Early talent density determines a startup's future team quality
“Whatever your company is or startup is right now is sort of the seed crystal for the company it will become. Okay. What does that mean? Well, you know, people don't usually want to join companies where the people are like less talented than them, right? So tal…”
Oct 18, 2022
Oct 18, 2022
Houston: Partnering with a long-time acquaintance as a co-founder is safer
“On average is probably better to a lot of the founder co-founder stories start with like, Oh, we played tee ball together as little kids and have known each other since forever. I think if you have that, that Is a bit of a safer bet.”
Oct 18, 2022 neutral
Oct 18, 2022
Drew Houston: Founders should use VC portfolio introductions to calibrate executive hiring
“Second, you lean on your investors. And if you have a great venture investors, we had Sequoia capital who had a great experience with they, part of their job is to have a network and Rolodex of great execs. And so asking your investor, putting your investors t…”
Oct 18, 2022
Drew Houston: Public high-growth struggles feel far worse than startup failure
“My first company, my bootstrap company, like it never really succeeded and then it died, but like, then Dropbox was like succeeding massively and then seemed to be dying massively. And I'm like, that is way worse than any of the others.”
Oct 18, 2022 negative
Oct 18, 2022
Oct 18, 2022
Oct 18, 2022
Oct 18, 2022
Jun 3, 2024 negative
Lemkin: Box and Dropbox Were Very Late to Go Multi-Product
“When we look at the boxes and the drop boxes, and I think both Aaron and Drew are honest here. They were very late to go multi-product and arguably drop boxes and multi-product at all. Arguably it's one product boxes kind of getting there, but I would say it's…”