The Peel
@ThePeelPod • 2,837 subscribers
Exploring the world’s greatest startup stories. hosted by @TurnerNovak. Watch full episodes 👉 https://t.co/ZRJGDoYMhV
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.@jason shares what it was like inside the Twitter / X buyout in 2022: "It would be 12-1am, everyone would be exhausted, and we'd do two more meetings. Elon just has an insane work ethic. In my opinion, it was the greatest heist in the history of business. A large portion of them were not working, making huge salaries, and spending money like drunken sailors. There was software and office space being paid for that was never touched. They were paying $400 for catered lunches. You could have sent them to Michelin star restaurants for every meal and still saved money. There were some people that were working hard. But there were people that were not working at all. Combined with COVID work form home work ethic, there was abuse in that system that has never been matched. It really broke people's brains when they laid off 85% of the staff and the product started working better and shipping faster. People realized these companies are massively overstaffed and you can do more with less."
The Peel309,312 Aufrufe • vor 5 Monaten
I talked to Eoghan McCabe about why you should be posting more: "Personally, you see every piece of content you post. And if you post a lot, it might feel like you're posting too much. But because of algorithmic feeds, no one else sees everything you post. So you can't assume everyone sees every single post. The average person will only see 10%, 20@, maybe 50% of what you post. No one will actually see all of it. And you don't know what's gonna work when you're posting. So you really just need to put a lot of shots on goal. It's like having a high shipping velocity on product. Imagine it takes 100 posts for something to break through. If you post 10x a day, it will take 10 days. If you post once a day, it will take over a quarter. Once a year, it will take 100 years. This is an advantage that some younger founders have. People like Amjad at Replit, he can work and tweet. He's built a great product. And he's constantly promoting it."
The Peel188,913 Aufrufe • vor 6 Monaten
I asked Will Gaybrick when Stripe will go public: "I think the better question is, why would we go public? What's the incremental benefit of going public? It's a bunch of work. It's a different way of operating. And there's a blurring of private and public investors. To this day we've never burned a dollar of investor money. We've always been financially independent, and now extremely profitable. We're focused on growing the GDP of the internet, as quickly as possible. We're already highly regulated financial institution, and resolutely focused on our customers."
The Peel124,520 Aufrufe • vor 6 Monaten
From Eric Vishria on how the top AI founders are building products completely opposite of the SaaS era: "One of the things that is really different in the AI world versus the SaaS world, is that in the SaaS world, over and over again, you had people who really understood the customer. And the problem. And then they understood a domain. They understood what the technology was more or less capable of. But it wasn't a real question of if you could build something or not. For example, take Salesforce, Workday, and ServiceNow. CRM existed before Salesforce. HR management existed before Workday. Same thing with ServiceNow. So in every case, Salesforce followed Siebel. Workday followed Peoplesoft. ServiceNow followed Peregrine and Remedy, and others. So they were just kind of, cloud SaaS versions of the prior generation product. They just understood the customers. They understood the problem. And they were just like, here's a better version. And that evolved a little bit over time in SaaS land. But that's what it is. And so product development in that way was done by people who really understood the customer and the problems. And then just took advantage of the next wave. And this is almost diametrically opposite of product development in the AI era. When I look at the teams that are having the most success today, they have intimate knowledge of the models. They are right on the frontier of understanding which models are better at what, and why, and when. And what they're going to be good at and what they're not going to be good at. And what they're spending their time on, is figuring out how do I apply this capability of this model to this domain or to this user. So they're actually working inside out or technology out, versus customer problem in. And of course, they understand the customer problem. And a lot of times they have firsthand knowledge of it. But they're really close to the metal and capability, and they're applying it. And I think this is a really different way to develop products than in SaaS. I started my career as a product manager a long time ago, and it's almost the complete opposite of everything you learned. "Listen to the customer, understand it, then bring it back to the engineering and product teams." If you did that right now, ask a bunch of customers what they want out of AI, and you brought it back, for the most part, it may not be possible today with today's technology. Whereas the teams that are winning right now really understand the technology and are applying it out. And so I think this reversal matters. I think it's a big difference in terms of how companies are getting built. And maybe even the types of entrepreneurs that will be successful. I'm not sure. You're seeing some real change there. Look at the Bret Taylor's at Sierra. That's a super, super technical founder who really gets it. Brett and Clay really get it. You look at Michael and his co-founders at Cursor. They're super technical founders and they get it. They all really understand what these things can and can't do. And that's a pretty different dynamic relative to the way the best SaaS companies got built." Link in bio for the full conversation going deep on the current class of startups going from zero to $100m+ in ARR within 12 months.
The Peel209,320 Aufrufe • vor 1 Jahr
Episode #123: Inside All-In with @jason - Lessons from Elon, Oprah, Trump, Travis Kalanick We go inside the origins of The All-In Podcast, how they decide what to talk about each week, and if Jason thinks they helped swing the election. We also talk lessons from starting 7 media companies over the past three decades, what he's learned from studying the world's best interviewers, joining Sequoia’s first scout program, his investing strategy at Launch, the story of being the 3rd or 4th investor in Uber, what people underestimate about Elon, and what it was like inside the Twitter buyout in 2022. Thanks to Numeral for supporting this episode and austin petersmith for help on topics. Timestamps: 3:34 Interviewing lessons from Oprah, Charlie Rose 6:48 How to ask good questions 12:20 Jason’s favorite upcoming podcasters 17:57 Starting 7 media companies 22:50 How he'd start a new media company today 27:56 In-person experiences, “Bang Bang” in Japan 32:44 Vinyl bars, smartphones, mental health 38:41 Origin of the All-In Podcast 42:58 All-In’s influence on the 2024 Election 46:58 Why All-In got so political 52:35 Media lessons from Trump 55:01 Joining Sequoia’s very first scout program 57:55 Jason’s VC investing strategy 1:03:55 How Launch competes with other accelerators 1:08:46 Fundraising is a numbers game 1:13:06 Investing in Uber and Robinhood Seed rounds 1:18:31 Origin of “3rd or 4th investor in Uber” meme 1:20:57 How Jason got the first Model S 1:26:19 What people underestimate about Elon 1:27:37 Inside the Twitter takeover 1:31:44 Career advice for young people 1:35:22 Jason’s experience taking GLP-1’s 1:40:05 How All-in picks topics each week
The Peel92,577 Aufrufe • vor 5 Monaten
I asked Erik Erik Bernhardsson why high CO2 levels in your office are such a big deal: "I'm not a health nut. But one of the things I've been radicalized on is CO2 levels. There's a real relationship between CO2 levels, productivity, and cognitive performance. And CO2 levels are usually way too high in offices and schools. Normal air CO2 levels are 300-500 PPM. In offices it often hits 1,000 or 2,000. Airplanes can get up to 2,500. You start getting brain damage at 5,000. So I went and bought a bunch of CO2 monitors for the office. And I look at them every day. And I open windows anytime we get too high."
The Peel107,531 Aufrufe • vor 7 Monaten
I asked Garry Tan how to use meta prompting to get better at AI: "My partners at YC Jared Friedman and Pete Koomen showed me how to do this. You can take almost anything that you do all the time and just drop it into a context window. And then say, “Here’s a bunch of inputs and outputs." And maybe you also add a bunch of notes. And then you tell it, “Write me a prompt that can act as an agent that takes this input and makes this output over here.” You can do this for almost any type of knowledge work. And you can even introspect. "What are things you notice that I did to convert this from the input to the output?”. And then you can just start using the prompt. Initially, it’s going to suck. Because it’s just not that smart yet. But what’s funny is now, I also use it to Iterate my writing. You can be very direct, "I would never say that", "Don’t say it like this", or "Oh, you used the long word there, use the short word". Just speak to it conversationally. And then when you're happy with the output, you can use that new output to make a new prompt. "Based on this conversation, give me a better initial prompt that incorporates all the things we talked about." And you can do this with literally everything. And in theory, there’s so much it applies to that people do day-to-day. You could use it for tweets. You could use it for editing podcasts. You can use it for pretty much everything. I have a folder of prompts that I use all the time. My YouTube prompt is on v27 or something. I'll go through this process with all the different max models. I'll use GPT 5.2 Pro. I’ll use Grok. I'll use Claude. Then, I’ll take all the outputs from all the models and put them into Claude and say "Here’s my prompt, here’s the output from four LLMs, including yourself. Rate each response and tell me what the pros and cons of each approach are." And I usually say "give it to me in numbered form". And then you can agree with one, disagree with two, tell it three is this or that. And then after that, you say given all of this, synthesize it."
The Peel51,632 Aufrufe • vor 3 Monaten
Episode #113: Howie: The AI Secretary I talked to austin petersmith at Howie about why AI assistants are so hard to build, deciding to make Howie super narrow, and everything that went into build the product, brand, naming, and viral launch video. Thanks to Hanover Park for supporting this episode! Stream here on X + link in the replies. Timestamps: 3:35 Howie: The AI Secretary 6:08 Why AI assistants are so hard to build 16:19 Why Howie started in email 20:49 Adding a human in the loop 30:48 AI software vs AI-powered humans 36:21 How a meme inspired Howie 39:29 Inside the making of Howie’s launch video 44:15 Howie’s viral launch video + Discussion 53:47 Designing the brand 1:01:37 Long-term opportunity and roadmap 1:07:53 Working for Jason Calacanis 1:12:00 Jason’s media lessons 1:16:51 How Howie got its first users 1:19:35 Pitch deck strategy that raised $6m 1:24:09 The mistake of optimizing for growth too soon 1:29:48 Building an AI company outside of SF 1:33:13 Being Superhuman’s 1st customer, Mercury’s 3rd
The Peel92,828 Aufrufe • vor 8 Monaten
From Garry Tan on what keeps him up at night: "99% of people who apply to YC get rejected. And it keeps me up at night. Up to half of any one batch may have been previously rejected before getting in. It's quite common to apply 2-4x before getting in. We get 80,000 applications per year. We're always worried we're over rotating in any direction. Too big can be bad. Too small can also be bad. And right now, there are clearly way more capable founders that we're rejecting. And if you can stand being rejected a few times, you're cut out to be a founder. Being a founder requires an insane amount of resilience. One rejection shouldn't hold you back. A really good founder would say, they got this wrong, and I'm gonna prove myself right. And we love that."
The Peel47,067 Aufrufe • vor 3 Monaten
I asked Jake Stauch about raising Serval's $75M Series B from Sequoia the day they announced their $50M Series A: "We closed the A in August and delayed the announcement until October. The day we announced, I got a text from Sequoia asking to come to their office. I was at a customer conference in Orlando. They ended up flying out and meeting me for dinner with a term sheet. They had talked to all of our customers. They talked to everyone I'd ever worked with, managers, peers, and direct reports. They also talked to all our competitors' customers. And they had a clear picture of the market, and just knew we were going to win. So instead of waiting on the sidelines, they wanted to come in immediately. And I initially turned them down. We had just fundraised. I didn't need the money. We were maybe 15 people at the company. I didn't have a way to deploy the capital. But I thought about it more. And talked to some references that had raised from Sequoia. And we decided the support on customer introductions and signaling, recruiting, and strategy would be valuable to us now vs waiting a few months."
The Peel37,117 Aufrufe • vor 3 Monaten
I asked Chris Hladczuk why he always gets on the plane: "Our customers are signing up for a decade-long relationship. You can't build the trust needed for that over a zoom call. If you're asking someone to trust you with something as important as what we build, the fact that I won't get on the plane and go see them for a few hours says a lot. Always get on the plane."
The Peel28,809 Aufrufe • vor 2 Monaten
I asked @jason what people underestimate about Elon: "It turns out building factories is actually the business model of most of his companies. There's a very small number of people who understand factories better than him. He's also the hardest working human being I've ever seen. When he acquired Twitter, we'd be up at 1am, everyone would be exhausted, and he'd want to do two more meetings. And then he'd have an 8am meeting the next day and start over again. His work ethic is inhuman."
The Peel43,747 Aufrufe • vor 5 Monaten
From Michael Kim on the best performing VC funds ever: "Chris Chris Sacca 🇺🇸's $8 million Fund 1 was 204x DPI. Chris had a great nose. He was in Instagram, Twitter, Uber, and Stripe. That's pretty good. The best performing fund in our portfolio is Mucker Capital Capital. Their $12 million Fund 1 was 20x DPI. They owned 7% of Honey, and got $280 million when it sold to PayPal for $4 billion in cash. Another is Dr. Dr. Manu Kumar 👋🏽. We're not in his Fund 1, but that was an 80x. He invested in Lyft, Twilio, and was a co-founder of Carta. He's the guy who actually coined the phrase "pre-seed" 12 years ago."
The Peel63,163 Aufrufe • vor 1 Jahr
Episode #93: Michael Kim @ Cendana Michael Kim is the Founder of Cendana Capital, making anchor investments in very early stage VC funds. We talk 204x DPI funds, characteristics of the top performing venture investors, how Cendana does diligence on fund managers, portfolio construction best practices + Michael’s 60x rule, and why a high ownership to fund size ratio drives outlier returns. We also get into how VCs are using AI, the competition between Seed and multi-stage investors, why US endowments are under siege, and how secondaries are driving most early stage venture returns today. Michael also opens up about the early days of starting Cendana, the 18 month grind raising Cendana Fund 1, the day he almost died, and ranking in the top 2% globally in Call of Duty. Shoutout to Roger Ehrenberg, Kevin Hartz, Semil, Jeff Clavier, Beezer Clarkson, Jack Altman, Jeff Morris Jr., Sheel Mohnot, Nichole Wischoff, Ted Alling, and Rick Zullo for their help putting this together. Thanks bolt.new for supporting this episode (check out their Hackathon with $1m in prizes!) Full episode here on X, or grab a link in the replies. Timestamps: 4:24 The day Michael almost died 5:10 Call of Duty & video games 9:34 Hiring @ Cendana 10:31 How Cendana uses structured and unstructured data 16:51 How VCs are using AI 19:55 Why secondaries are driving most early stage venture returns 22:01 Deciding when to sell secondaries 24:28 Best performing venture funds ever 27:26 The best VCs have amazing access to the best founders 33:42 Why Cendana backs Solo GPs 35:57 How to invest over time and hype cycles 41:35 Why multi-stage firms are investing earlier 44:45 Cendana’s current thesis: High ownership % to fund size 45:51 Why Cendana started backing non-lead VCs 48:41 How Cendana does diligence on fund managers 52:22 VC NPS Scores and Ron Conway’s Silver Bullet 53:49 Good vs bad new VC firm strategies 56:36 Determining defensibility of a strategy 57:57 “Messy middle” software buyout fund 1:03:25 Portfolio construction best practice 1:08:11 Michael’s 60x Rule 1:14:28 How Seed funds compete with multi-stage funds 1:20:05 Should you collect logos writing small checks? 1:21:07 Becoming an LP for the city of SF 1:24:42 Taking 18+ months to raise Cendana Fund 1 in the GFC 1:26:48 Warehousing the first Cendana Fund 1 investments 1:29:56 How to do a first close 1:34:29 Why it’s hard to kill a VC firm 1:37:00 What happens to ZIRP tourist fund managers 1:40:22 How to raise a Fund 2 or 3 today 1:42:07 “US endowments are under siege” 1:44:55 What the best GP LP relationships look like 1:46:41 What Fund of Funds get wrong 1:50:43 The three most interesting trends in venture today
The Peel61,633 Aufrufe • vor 1 Jahr
I talked to Chris Hladczuk about competing against companies who think of engineering as the IT department: "If you're one of the greatest engineers in the world, why would you work somewhere you're a 2nd class citizen? Never in your wildest considerations or nightmares would you join one of our legacy competitors that doesn't care about you. If Ramp can make expense management sexy, you as a founder can make your category sexy. At Hanover Park we wanted to build a hacker culture. A team of elite engineers, who otherwise might join an AI lab, and have a deep obsession with building for the most complex fintech and data problems in the world. That's a very different value prop than a legacy fund admin we compete against."
The Peel18,625 Aufrufe • vor 2 Monaten
Episode #88: Surviving Two Seed Extensions, Fixing Auth for AI Agents with Colin @ Clerk Colin Sidoti Colin | clerk.com is the Co-founder and CEO of Clerk, the best way to build authentication and user management. Clerk has not been an easy journey, and Colin takes us inside some of the harder moments from the past six years. We hit on three main themes: authentication, lessons raising multiple hard Seed extensions (and a recap before the A!), and how AI and MCP intersect with auth. We also talk founding a company with his brother, building a compound startup, why components are the new APIs, and what he learned about audacious goals from John Collison. Big thanks to Reid Christian, Paul Klein IV, and Joseph Nelson for helping brainstorm topics for Colin. Full episode below + link in the replies. Timestamps: 3:39 The best developer tool for authentication and user management 5:45 The easiest way to set up billing 7:13 Building a compound startup 9:15 Lesson on audacious goals from John Collison 12:40 Developer tools are now trusted category experts 13:47 How auth impacts billing, CRM, marketing, analytics 19:44 Why auth is always changing 25:40 Coming up with the idea for Clerk 29:24 What its like starting a company with your brother 30:58 Living in a basement during Clerks early days 35:33 Getting early users narrowing focus in South Park Commons 40:10 Fundraising lessons from struggling to raise 43:46 The trick that raised Clerk’s first round from S28 45:09 Launching + the first Seed extension 50:15 Sequoia’s feedback that improved conversion rates 52:22 Why a16xz led Clerk’s 2nd Seed extension 58:11 How to do a recap before Series A 1:03:34 Changing Clerk’s pitch to scare investors 1:08:56 Fundraising advice “Why partner alignment is all that matters” 1:11:42 Fast Series A and breaking 7%/week growth 1:16:32 Negotiating Clerk’s Series B at the bar 1:22:15 Investors in the arena vs in their mansions 1:27:57 The three ways AI is changing authentication 1:31:21 Why AI agents all try to steal free AI credits 1:33:09 Remember to have fun 1:36:24 Building a better product to compete in a crowded market
The Peel63,845 Aufrufe • vor 1 Jahr