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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
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Reid Hoffman, Stacy Brown-Philpot, and Aileen Lee are three of the most successful, legendary leaders and investors in Silicon Valley. (The term “unicorn” for a startup valued at a billion dollars? Well, Aileen coined that.) This power trio sat down with journalist Van Jones live onstage at the 2025 Masters of Scale Summit, October 8 in San Francisco, to share candid snapshots of the investor’s mindset during this time of rapid change. Learn why VCs have dramatically shifted the way they invest in entrepreneurs this year, how companies can stand out in the crowded AI space, their personal green lights or red flags, and how players on all sides can adapt.
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Today’s show:
Aileen Lee join Jason to talk about her origins and overcoming challenges as a woman in a male-dominated tech space (2:12), the Unicorn Club and the effects of the ZIRP era (11:51), predictions on which startups will maintain their unicorn status (33:09), and more!
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LINKS:
Check out Cowboy Ventures: https://www.cowboy.vc/
Read Aileen’s 2024 article here: https://www.cowboy.vc/news/welcome-back-to-the-unicorn-club-10-years-later
Read Aileen’s original Unicorn article here: https://techcrunch.com/2013/11/02/welcome-to-the-unicorn-club/
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Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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Kara and Scott discuss Ron DeSantis' departure from the 2024 race and the Biden/Trump rematch that everyone is dreading. Then, with the good news about the economy and the stock market, what's the best move for investors? Plus, Nelson Peltz continues his Disney proxy fight, and a new report sheds light on the anti-DEI movement. Our Friend of Pivot is Aileen Lee, the founder and managing partner of the VC fund, Cowboy Ventures. She also happens to be the person who coined the term "unicorn" for billion dollar start-ups and shares her latest analysis on those companies.
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This is our interview show, where we sit down with interesting, knowledgeable folks and dive deep into their favorite topics. This time around, we invited Cowboy Ventures’ Aileen Lee to chat through her massive new article concerning the unicorn world. If you didn’t know, it was Lee who initially coined the term “unicorn” in a TechCrunch article back in 2013.
Lee talked us through the data and taught us all sorts of new terms. You can sort of understand what one means when they say “unicorpse” or “zombiecorn,” but apparently there are even more exotic unicorn forms out there. We even wound up comparing venture capital returns to peaches in a bucket of piss (her words, not ours!).
We also talked about where unicorns are based today (19% in New York, for example), and why seed rounds are getting bigger. But really, you should read her post while you listen so you can have all the context while we chew through the numbers!
And for those of you who are here for the answer to our question, “How are Fortune 500 companies ranked?”, well, the answer is revenue and not market cap.
For episode transcripts and more, head to Equity’s Simplecast website.
Equity drops at 7 a.m. PT every Monday, Wednesday and Friday, so subscribe to us on Apple Podcasts, Overcast, Spotify and all the casts. TechCrunch also has a great show on crypto, a show that interviews founders and more!
Credits: Equity is produced by Theresa Loconsolo with editing by Kell. Bryce Durbin is our Illustrator. We'd also like to thank the audience development team and Henry Pickavet, who manages TechCrunch audio products.
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The number of global venture capital (VC) investments dipped in 2022, thanks to ongoing geopolitical tensions, turbulence in global capital markets, supply chain issues, and increasing interest rates. This has caused VC investors to be increasingly wary. With no end in sight to the economic uncertainty, VC investment could remain soft, with downward pressure on valuations resulting in decreasing levels of investment.
Founder and Managing Partner at Cowboy Ventures, Aileen Lee, discusses the state of the VC market in 2022 with Founder and CEO of SaaStr Jason Lemkin—the change in VC activities and seed deals, the importance of the board in the success of a startup, profitability and much more.
Full video: https://youtu.be/R3G6P19qHY4
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Aileen Lee is a U.S. seed investor. A venture capital investor, she is the founder of Cowboy Ventures. Lee coined the often-used Silicon Valley term unicorn in a TechCrunch article "Welcome To The Unicorn Club: Learning from Billion-Dollar Startups."
In this episode of the SaaStr podcast, Aileen and SaaStr Founder Jason Lemkin take a deep dive on how Aileen finds deals, her tips for a winning pitch, and the state of VC in 2020.
This episode is an excerpt from Aileen and Jason's session at SaaStr Summit: The New New in Venture.
Full video: https://youtu.be/J5bhChbqcLU
Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-aileen-lee-and-jason-lemkin/
0:51 Jason intros Aileen Lee
1:36 Aileen on her time at MIT, early bias against women in math
5:56 What brought Aileen to San Francisco & working at GAP in the early days of the Internet
9:40 Aileen on working for Mary Meeker & what makes her special
10:25 “All companies that leverage technology are not the same.”
13:10 What made WeWork attractive to investors in the early days?
17:54 How the market is skewed to reward growth
22:35 Thoughts on SoftBank increasing valuations
28:24 How Aileen got involved with Dollar Shave Club
31:07 Jason’s experience with Dollar Shave Club
32:07 “Crushing it” culture in tech
35:12 Aileen’s history at Kleiner Perkins
36:27 Being a woman in VC in the 2000s
41:12 Starting Cowboy Ventures
43:46 Diversity in tech
48:38 What are they working on at All Raise?
Ted Wang is a Partner @ Cowboy Ventures, one of Silicon Valley's leading early-stage funds with the likes of Philz Coffee, Dollar Shave Club, Brandless, DocSend, Accompany and Brit + Co all in their portfolio. As for Ted, prior to VC, Ted spent X years as a leading Silicon Valley lawyer with Fenwick & West where he worked with some of the most notable companies of our times including Facebook, Dropbox, Twitter, Square and Spotify just to name a few. Ted also created the Series Seed Documents - a set of open-sourced financing documents posted on Github used by thousands around the world today.
In Today's Episode You Will Learn:
1.) How Ted made his way from one of the most renowned lawyers in the valley with Fenwick & West to partner @ Cowboy alongside Aileen Lee?
2.) How does Ted fundamentally approach risk today? Given this mindset, how does this impact Ted's thinking on optimizing portfolio construction? On the flip side, how has Ted seen many founders wrongly approach the theme of risk? What is the question they need to be asking? What is Ted's story about risk related to his time working with Jet?
3.) What is it that makes Ted believe that "advice is often oversimplified"? If so, how can VCs provide tangible advice to their portfolio companies today? How can founders determine what is the right advice to accept and integrate vs listen and disregard? How does this lead Ted's thinking on the 2 core value adds a VC can provide? What advice did Dropbox Founder, Drew Houston give Ted on when to accept advice?
4.) What does Ted mean when he says "there are 4 parts to venture"? How does Ted think about the theme of learning and self-improvement when assessing founders? How does he look to do this pre-investment? What questions reveal the most? Applying it to himself, where will Ted place his biggest efforts on learning within the realm of venture over the next 12 months?
Items Mentioned In Today's Show:
Ted's Fave Book: 7 Habits of Highly Effective People
Ted's Most Recent Investment: Fullcast
As always you can follow Harry, The Twenty Minute VC and Ted on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta's new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.
Recode’s Kara Swisher talks with three tech leaders about actual solutions for advancing diversity in the industry. Cowboy Ventures partner Aileen Lee, theBoardlist founder Sukhinder Singh Cassidy and former U.S. Chief Technology Officer Megan Smith talk about the factors that have historically held back women, people of color and other under-represented groups in tech, and what comes next after the reckoning of the #MeToo movement. The group debates how men can best help their female peers succeed and how companies can avoid falling into the trap of thinking that the solution is just to keep men and women apart.
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Cowboy Ventures founder and managing partner Aileen Lee, previously a partner at Kleiner Perkins Caufield & Byers, talks with Recode's Kara Swisher about being one of the few female venture capitalists in Silicon Valley. After leaving Kleiner Perkins in 2012, Lee set out to amass data about the small percentage of startups that become breakout success stories, and she coined the term "unicorn" to describe the small fraction that would be valued at more than $1 billion. She says entrepreneurs today have to be tougher now that investors' fervor has cooled off, and says those investors will have to change, too, by becoming more diverse.
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Noah Lichtenstein from Cowboy Ventures and Kimono Labs co-founders, Pratap Ranade and Ryan Rowe, swung by Product Hunt HQ to chat about products. We discuss Twitter’s new Group DM’s, Snapchat’s media play with Discover, and halfway through the show we accidentally make an announcement. Listen in.
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