Kevin Hartz | Backing Teen Founders, Lessons from the PayPal Mafia
Kevin Hartz, Co-founder of A*, Eventbrite, Xoom, and Sauron.
Kevin has been building and investing in technology companies for 30 years, and we talk about how the industry’s evolved, why he calls AI the Mother of All Bubbles, why we’re still early, and lessons today’s breakout AI companies can learn from those that survived the Dot Com Crash.
Kevin is a big proponent of backing young founders. A significant percentage of his latest fund at A* is invested in teenagers, and he shares how he identifies outlier talent so early, from Seed investments in Airbnb, PayPal, and Pinterest, to many of today’s hottest AI companies.
He also shares the insane story of investing 100% of the proceeds from his first startup into PayPal’s Seed round, how PayPal’s early fraud systems inspired Palantir, what he learned from the PayPal Mafia, from Peter Thiel, and what makes Founders Fund special.
We also talk about how he and his wife recently had two babies, five months apart, using genome screening and surrogates.
Thanks to Ramtin Naimi, Navya Gudimetla, and Bennett Siegel for helping brainstorm topics for the conversation.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(4:25) Power shift from VC’s to founders since the 90’s
(9:08) AI is the mother of all bubbles
(12:40) Why AI is still underhyped
(14:10) What Kevin and A* are investing in today
(16:02) Investing 100% of his first startups proceeds in PayPal’s Seed round
(21:21) What made the PayPal Mafia special
(23:37) Parallels between the 90’s and today
(26:40) What makes Founders Fund special
(35:07) How Palantir evolved from PayPal’s fraud models
(39:06) Building Xoom on the PayPal API
(43:38) Lessons between Kevin’s 1st and 2nd startups
(46:52) Starting Eventbrite off early PayPal API app
(51:51) Eventbrite’s hidden TAM challenge
(53:49) Selling Eventbrite to Bending Spoons
(54:59) Investing 20% of A* in teenage founders
(1:02:33) Incubating Sauron, the home security company
(1:08:44) Making breakfast for our kids
(1:13:33) Having kids with genome screening and surrogates
(1:20:31) Collecting art, how to get started
Referenced
https://www.a-star.co/
https://www.eventbrite.com/
https://www.xoom.com/
https://www.sauron.systems/
https://www.orchidhealth.com/
Setting the Table by Danny Meyer: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/0060742763
20% of fund in teenage founders: https://techcrunch.com/2025/10/18/this-top-vc-bet-close-to-20-of-his-fund-on-teenagers-heres-why/
https://nypost.com/2025/12/14/us-news/xu-bo-chinese-billionaire-reportedly-sires-more-than-100-kids/
Follow Kevin
Twitter: https://x.com/kevinhartz
LinkedIn: https://www.linkedin.com/in/hartz
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
20VC: How I Lost Airbnb at Seed Because of an Exploding Term Sheet | Investing Lessons from Roelof Botha & Peter Thiel | Why VC is Less Collaborative Than Ever and Great Companies Are Being Destroyed by Too Much Cash with Kevin Hartz @ A*
Kevin Hartz is a Co-Founder and General Partner at A*, an early-stage venture capital firm. Prior to founding A*, Kevin co-founded Eventbrite, a publicly traded company, and served as the CEO for the first 11 years of the company. Before Eventbrite, Kevin co-founded Xoom, a money remittance company that was acquired by PayPal in 2015 for over $1BN. Kevin is also a prolific angel investor having backed companies such as PayPal, Airbnb, Pinterest, Ramp, Trulia, and Anduril at the seed stage, and was an early investor in Uber, Palantir, SpaceX, Square, Gusto and many others.
In Today's Episode with Kevin Hartz We Discuss:
1. What Makes the Best Founders:
What questions does Kevin always ask founders in the investment process?
Does Kevin prefer serial or first time founders? Why?
Does Kevin prefer founders who are new to a problem or who are insiders and experts?
When Kevin has gotten a founder bet wrong, what did he not see that he should have seen?
2. The Exploding Term Sheet That Cost $10BN:
How did an exploding term sheet for the seed round of Airbnb cost Kevin $10BN?
What did Kevin see in the seed round of Airbnb that so few other investors saw?
Does Kevin agree that the best businesses often start off as ridiculous or toys?
3. From World's Greatest Angel to VC with $600M AUM:
Why does Kevin think a barbell strategy of Seed and Series C is best today?
Does Kevin agree that the Series B and growth stage is dead today?
Why does Kevin strongly disagree that seed is the hardest stage of the market?
Why does Kevin think that venture is less collaborative than ever?
How does Kevin approach when to sell vs when to hold a position?
What are his biggest lessons from seeding and holding Opensea?
4. Learning From the World's Best Investors:
What have been Kevin's lessons from his relationship with Peter Thiel?
What have been Kevin's biggest takeaways from investing alongside Roelof Botha in many deals?
What have been Kevin's biggest lessons from watching and observing the great Pierre Lamond?
20VC: SPACs. What Are They? Why Now? How Do They Change The Venture Landscape? Are They Better Than IPOs & Direct Listings? How Should Founders Think About Them? Kevin Hartz & Troy Steckenrider @ A*
Kevin Hartz is Co-Founder & Partner @ A*, a newly listed special acquisition company which raised $200M to acquire and take public a tech startup. Kevin is also the Co-Founder, former CEO, and Chairman Eventbrite (NYSE: EB). Before Eventbrite, Kevin was the Co-Founder & former CEO of online money transfer service, Xoom (acquired by PayPal for $1.1B). Kevin is also one of the most successful early-stage investors in the business with a portfolio including the likes of Airbnb (Seed, Series A), Uber (Series B), Pinterest (Seed, Series A), Trulia (first check) and PayPal (Seed).
Troy Steckenrider is Kevin's co-founder and Partner @ A*. Prior to A*, Troy was COO @ ZeroDown changing the landscape for homeownership with $136M in funding. Before ZeroDown, Troy spent 5 years at Opendoor as Director of Capital Markets. Before that hyper-growth experience at Opendoor, Troy enjoyed roles at both Bain Private Equity and McKinsey.
In Today's Episode You Will Learn:
1.) How Troy and Kevin came together to co-found A*? What is a SPAC? What are Kevin and Troy looking to achieve with the SPAC?
2.) What does Kevin believe are the primary drivers for the rise in SPAC's over the last few years? How will they change the structure of both the VC and startup industry? How will the SPAC landscape evolve over the next few years? What is the biggest challenge they face?
3.) Why does Kevin believe that the fee structure for SPACs is egregious? How would they like to change the incentive structure? How does the timeline for a SPAC transaction compare to that of an IPO? How does the fee structure compare when comparing SPACs to banks in IPOs?
4.) Why did Kevin and Troy choose $200M for the right size for their first SPAC? How does the size of the SPAC determine the type of company the SPAC will merge with? What are Kevin and Troy looking for in their partner company?
5.) What does the fundraising process look like for a SPAC? How do SPAC sponsors deal with the challenge that LPs call pull out if they do not like the proposed partner deal? When evaluating SPACs, what do investors look to invest because of? What makes A* special?
Items Mentioned In Today's Show:
Troy's Fave Book: Churchill: Walking with Destiny
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Primer on SPACs with Kevin Hartz and Troy Steckenrider of A* and AONE
We dive into everything you need to know about SPACs — what they are, why they're a compelling alternative to IPO/DPOs, and how they might play an even more important role in startup financing going forward — with two of the very best people to teach us: Kevin Hartz and Troy "SPAC Professor" Steckenrider of the newly-minted $200m SPAC, AONE.
Sponsors:
Sierra: https://bit.ly/acquiredsierra
TLDR:
SPACs are an alternative path for companies to go public, however until recently they were mostly obscure and little-known/used.
Meanwhile, the traditional IPO process has become onerous and broken: it takes 9+ months of company time, yet investors get only 15 minutes of management access and must make a decision in
Links:
A* and ONE: https://www.a-star.co
John Luttig's great Medium piece on SPACs: https://luttig.substack.com/p/spac-attack-everything-a-founder
Bill Gurley on SPACs as an attractive alternative to IPOs/DPOs (posted after recording): https://abovethecrowd.com/2020/08/23/going-public-circa-2020-door-3-the-spac/
Eventbrite (with Julia & Kevin Hartz)
We're joined by two very special guests, Eventbrite CEO Julia Hartz and her cofounder, spouse and Eventbrite Chairman Kevin Hartz, to tell their story of building Eventbrite together (along with their lives and family) from the PayPal diaspora to bootstrapped business, unicorn status, IPO and now starting all over again in the wake of COVID with both a tragedy and a huge new opportunity in front of them as public company.
Sponsors:
Anthropic: https://bit.ly/acquiredclaude25
Sentry: https://bit.ly/acquiredsentry
WorkOS: https://acquired.fm/unpluggedPlaying Cards: https://bit.ly/workOSshop (Code: ACQDECK)
Statsig: https://bit.ly/acquiredstatsig26
More Acquired!
Get email updates with hints on next episode and follow-ups from recent episodes
Join the Slack
Subscribe to ACQ2
Merch Store!
© Copyright 2015-2026 ACQ, LLC
New! We're codifying our own Playbook notes and takeaways from each episode, and posting them here in the show notes and on our website. You can read them below or at: www.acquired.fm/episodes/eventbrite
Playbook
Seeing the next technology wave before others do is rare. It provides a roadmap for what to build and invest in if you're willing to bet on that knowledge. Kevin worked at Silicon Graphics in the mid 90's. This led him to realize that internet services like PayPal, YouTube, and many others would be possible long before others (similar to Don Valentine realizing computers would penetrate every industry from his time at Fairchild).
PayPal and its subsequent "mafia" was successful in part because of rapid experimentation. They observed what got used by customers and then doubled down. PayPal's "core" use case on eBay started as an experiment. International money transfer (Xoom) and event ticketing (Eventbrite) also initially started as experiments on the PayPal API before the eBay acquisition — and went on to become large companies.
Julia, Kevin, and their cofounder Renaud had a prototype of Eventbrite running and serving customers even before starting the company — which gave them the confidence to do what seemed crazy on paper, but was actually "de-risked": start a company as an engaged couple, have a remote technical cofounder, bootstrap for 2 years after being turned down by VCs, etc.
When a company is experiencing explosive growth, they often need to leave other huge opportunities on the table. PayPal knew international remittances could be huge, but didn't build it internally because of the need to focus on eBay merchants.
The TAM for bringing an offline behavior offline is often WAY bigger than anything you can calculate beforehand. The range and size of what were previously niche or impossible use cases will often expand dramatically with easy-to-use online tools. This is especially true in long-tail use cases that can only be aggregated by self-serve internet-based software. One early encouraging sign for Eventbrite was its use to host speed dating events in New York. Before Eventbrite, it was nearly impossible to organize, promote, and charge for something like that. Now, organizers could suddenly become entrepreneurs and make real money hosting events like this. Most VCs ignored or were confused by this data (~"Call us when you attack Ticketmaster."), but they missed that it unlocked a massive new market which previously operated only through word-of-mouth and cash transactions (if at all).
All three major dislocations of the 21st century — the tech bubble bursting in 2001, the financial crisis in 2008, and now COVID in 2020 — have only accelerated offline behaviors to online. COVID is unlocking a new wave of online event entrepreneurs for Eventbrite in the same way the financial crisis unlocked a wave of in-person event entrepreneurs in 2008-10.
Starting with just one niche can be incredibly powerful; often your customers will then lead you to more. Before the speed-dating in New York (which was fully inbound), Eventbrite was used to organize tech meetups in the then-smaller tech community in SF. It was even used for the first TechCrunch Disrupt!
Too much capital (and too little accountability) can hurt a company much more than help it. Capital covers up problems, distracts focus from customers, and leads to poor resource allocation. Kevin: "The periods where we had raised the most money privately were the hardest and most difficult for me, because we were really fighting this gravity of overspending and creating inefficiency. And it took us away from our roots as a capital-efficient, highly-effective perpetual motion machine [that we'd had as a bootstrapped company]."
Being a public company not only instills more capital allocation discipline, but can ALSO afford a degree of financial flexibility that just isn't possible as a private company. Within weeks of COVID hitting, Eventbrite dramatically shrunk the size and scope of the company AND raised $375m in new capital from new and longterm shareholders. Both actions would have been difficult to impossible as a private company with a static valuation (and associated anti-dilution, ratchet terms, etc) that no longer reflected the reality of the current situation.
20VC: Founders Fund's Kevin Hartz on Why Investing In Silicon Valley Is Broken & Why Fearlessness Is What Makes The Truly Great Investors
Kevin Hartz is a Partner @ Founders Fund, one of the world's most prestigious and successful VC funds with prior investments in the likes of Facebook, Airbnb, SpaceX, Spotify and many more incredible companies. Prior to Founders Fund, Kevin was Founder & CEO @ Eventbrite, the company that powers thousands of millions of events around the world with backing from the likes of Sequoia and SV Angel. Before that Kevin was the Founder of Xoom Corporation, the international money transfer company that went public in 2012 and was acquired by Paypal in 2015. Kevin has also been a prolific angel with a personal portfolio including Airbnb, Uber, Paypal, Pinterest and Yammer.
In Today's Episode You Will Learn:
1.) Question from Brian Singerman: How did Kevin come to be the world famous Kevin Hartz? What was Kevin's entry into the world of VC?
2.) How has Kevin seen his investment decision making and evaluation process change when comparing his angel deals in Uber, Paypal and Airbnb to today, investing institutionally with Founders Fund?
3.) How does Kevin see believe his time in operations lends to him being a better investor today? Does Kevin agree with Pat Grady @ Sequoia in stating, 'the rate of decay on operating experience has never been greater'?
4.) With no Monday morning Partner meetings, if a Partner wants to push a deal through, how do you do it at Founders Fund? How do you structure those conversations internally?
5.) What have been Kevin's biggest learnings since joining Founders Fund? How did Kevin look to scale the VC learning curve as fast as possible? What elements did Kevin find most challenging?
Items Mentioned In Today's Show:
Kevin's Fave Book: Peter Thiel: Zero To One
Kevin's Most Recent Investment: HyperTrack
As always you can follow Harry, The Twenty Minute VC and Kevin on Twitter here!
Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.
Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom's their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business.
Vidyard is the video platform for business that helps marketing and sales teams drive more revenue through the use of online video. Going beyond video hosting and management, Vidyard helps businesses drive greater engagement in their video content, track the viewing activities of each individual viewer, and turn those views into action. Global leaders such as Microsoft, McKesson, Lenovo, and LinkedIn rely on Vidyard to power their video content strategies and turn viewer into customers. Check them out at vidyard.com.