Keith Rabois, Co-founder and CEO of OpenStore, discusses the problems in ecommerce, why Instagram Shopping and Wish failed, contribution margin in startups, and what he looks for in founders. He also shares his thoughts on AI startups, his favorite interview questions, and the reasons behind moving to Miami.

Natasha Vernier, Co-founder and CEO of Cable, discusses the $4 trillion market of financial crime, highlighting the prevalence of crime for financial gains and the difficulty in stopping it. She explores the increase in financial crime on crypto rails and the growing synthetic ID fraud. Natasha also shares her experience joining Monzo, building Cable to help regulatory and financial crime teams, and raising funds for the startup.

Alex Bouaziz, Co-founder and CEO of Deel, shares the journey of growing Deel from zero to $300M+ ARR in four years. Topics discussed include the initial insight around remote work, pivoting before YC demo day, Deel's remote-first approach, fundraising strategies, and the importance of building the right board and selecting committed board members.

Semil Shah is the Founder of Haystack, an institutional venture capital firm that backs outlier founders at the earliest stages. Semil started Haystack in 2013, and has since invested in X unicorns like DoorDash, Instacart, Figma, HashiCorp, Ironclad, Carta, Applied Intuition, and Opendoor. This episode takes us behind the scenes of Semil’s two decade journey building Haystack from scratch. We’ll dive into how he raised and deployed each of the first six Haystack funds, including all the mistakes made along the way, plus the details around Haystack’s new $75 million and $25 million funds announced the date this episode was published. Read Haystack's announcement here: https://semilshah.com/2023/09/10/announcing-haystack-vii-same-model-fresh-funds-and-new-era/ — Brought to you by Mercury, the bank built for startups. Join more than 100,000 startups and venture capital firms on Mercury, the powerful and intuitive way for ambitious companies to bank. Sign-up now: https://bit.ly/3sQRzOw Listen to my conversation with Immad, the Co-founder and CEO of Mercury: Spotify: https://open.spotify.com/episode/24ujuXZ2uws48bvwOh9NcR Apple: https://podcasts.apple.com/us/podcast/lessons-from-building-mercury-with-immad-akhund-co/id1694440669?i=1000619360042 Disclaimer: Mercury is a financial technology company, not a bank. Banking services are provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC. — Topics discussed include: Juggling multiple jobs while living paycheck to paycheck his first eight years in Silicon Valley Failing to get his first job in venture three times Investing in the Seed rounds of unicorns DoorDash, Instacart, Hashicorp, and Envoy within the first six months of starting Haystack Why he initially thought Haystack would be a short-term thing Turning down multiple lucrative job offers two years in How the best LPs evaluate VC funds on the “Entry Ownership to Fund Size” ratio Semil’s strategy of “crawl, walk, run” to increase Haystack’s check sizes over time The pain he felt failing to hit his target fund size on the first four fundraises and how he handled it Why everyone should “pre-market” a fundraise, and how to do it The things most founders don’t appreciate about raising a venture fund Fighting to invest in Ironclad’s Seed round before he had his next fund raised How LPs reference VCs, and how a VC can become referenceable Why Haystack Fund IV was the scariest fund to raise How Semil builds relationships with LPs The hardest questions he faced raising each fund and what other VCs should anticipate while raising their own fund How LP investment committees make decisions What’s going on behind the scenes at most large venture LPs today Why the traditional advice of “finding an anchor LP” makes no sense Spilling his secret on the best quarter to fundraise Why VCs should fundraise with a hard cap on fund size Why every VC should appreciate and remember how LPs supported them through the pandemic All the details on Haystack’s new $75 million and $25 million funds Semil’s plan for the next 10 years Three pieces of advice for emerging fund managers Where to find Semil: Twitter: https://twitter.com/semil LinkedIn: https://www.linkedin.com/in/semilshah/ Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Production and distribution by: https://www.supermix.io/ For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Sean Frank, CEO of Ridge Wallet and known as the 'Einstein of Ecommerce', discusses topics such as the challenges of selling wallets, Ridge's 80% gross margins, the decision to not raise venture capital, hiring a new CEO, marketing strategies including Twitter advertising and influencer sponsorships, the future of women's return rates in fashion, vertical integration through investing in a watch manufacturer and building a factory, the importance of core competency, Ridge's tech stack, and the challenges and potential future of e-commerce penetration.

Dimitri Dadiomov, Co-founder and CEO of Modern Treasury, discusses the challenges of moving quadrillions of dollars annually in the global banking system. He explores the importance of easy-to-use B2B products with broad use cases, the qualities of a good API business, and why building deep customer relationships across industries is vital. Dimitri also shares insights on finding market gaps, the depth of Modern Treasury's product, and the significance of going slow to go fast in business growth.

Kendall Baker currently leads Yahoo’s sports newsletter business. In 2017 he launched the first daily sports newsletter called Sports Internet, which he sold to Axios in 2019. Before Sports Internet, he convinced the founders of The Hustle to focus their online tech blog on a daily newsletter, which he wrote for a year and a half. And before The Hustle, he produced SportsCenter at ESPN. He’s spent nearly a decade at the intersection of daily news and sports, and this episode is packed with insights on both. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3OwGdGC Read the transcript: https://www.thespl.it/p/the-business-of-newsletters In this episode, we discuss: The history of the newsletter industry Why the best writers delete more than they write How he got on ESPN SportsCenter A crash course on the sports media business How to write a daily newsletter The importance of experimenting How he got his first dollar of revenue Why Kendall spent $0 on growth Selling his “Sports Internet” newsletter to Axios Why Adam Silver, commissioner of the NBA, reads Kendall’s writing Why Yahoo’s the next rocketship The surging momentum in US soccer And the most underrated athletes (current and all-time) Listen on other platforms: Apple: https://podcasts.apple.com/us/podcast/the-business-of-newsletters-kendall-baker/id1694440669?i=1000624033211 YouTube: https://youtu.be/4es4p7sFMf0 Where to find Kendall: Twitter https://twitter.com/kendallbaker Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Read the transcript: https://www.thespl.it/p/the-business-of-newsletters Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Dan Porter is the Co-founder and CEO of Overtime, a sports network for the next generation of fans. OT reaches 85 million fans per month and runs a basketball league (Overtime Elite, OTE), a flag football league (OT7), and is launching a boxing league (OTX) the week this episode airs. Dan started Overtime with his co-founder Zack Weiner in 2016, and has since raised over $215 million. OT is supported by investors like the late ex-NBA Commissioner David Stern, Jeff Bezos, Drake, Carmelo Anthony, Trae Young, over 25 other NBA players, Spark Capital, Redpoint, a16z, Greycroft, Afore Capital, and Banana Capital. [Turner Novak and Banana Capital are investors in Overtime]. Brought to you by Secureframe, the automated compliance platform built by compliance experts: ⁠http://bit.ly/3Qk4RNd In this episode, we discuss: The business of sports Why people love sports The founding story of Overtime How to raise money for a unique idea Overtime’s very first product How to bet on technological change The changing professional sports landscape How to launch a sports league Why founders must obsess over their product Read the transcript: https://www.thespl.it/p/how-overtime-grew-to-85-million-fans Where to find Dan: Twitter: ⁠https://twitter.com/tfadp⁠ LinkedIn: ⁠https://www.linkedin.com/in/danporter/⁠ Where to find Turner: Newsletter: ⁠https://www.thespl.it⁠ Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/TurnerNovak⁠ Where to find The Peel: YouTube: ⁠https://www.youtube.com/@ThePeelPod⁠ Instagram: ⁠https://www.instagram.com/ThePeelPod⁠ TikTok: ⁠https://www.tiktok.com/@ThePeelPodcast⁠ Read the full transcript: https://www.thespl.it/p/how-overtime-grew-to-85-million-fans Production and distribution by: ⁠https://www.supermix.io⁠ For sponsorship inquiries: ⁠https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform⁠

Nick Saltarelli is the Co-founder of Mid-Day Squares, a healthy, functional chocolate bar. Nick, his wife Lezlie, and her brother Jake started the company in 2018 from their kitchen in Montreal, and have since built their own factory with $70 million in capacity, and grown the company to a $26 million revenue run rate. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/building-a-70-million-chocolate-factory In this episode, we discuss: The history of the $200 billion chocolate market Competing against 100+ year-old monopolies Finding a huge opportunity in healthier chocolate The dirty secrets of contract manufacturing Why no one knows how to make a Snickers bar, and Coca-Cola doesn't have a patent How to build a moat in CPG Why Mid-Day Squares had to build their own factory Making chocolate like Tesla makes cars Copying Facebook’s launch strategy Measuring product market fit in CPG Almost running out of money during COVID Why every founding team should go to therapy Surviving an 85% drop in revenue How to raise a bridge round Building an enduring brand Why marketers should study the music industry Timestamps [00:00:00] Intro [00:03:07] The insane politics of chocolate [00:04:53] The history of chocolate [00:07:11] The enormous market for chocolate [00:10:24] The nutrition of chocolate [00:15:00] The Mid-Day Squares origin story [00:20:05] Creating the first product [00:25:53] Why Coca-Cola never filed a patent on their formula [00:29:08] Why they built their own manufacturing plant [00:31:35] A crazy and creative fundraising strategy [00:39:26] Taking over an island and finding PMF [00:46:32] Raising $2m to prove 2 things [00:47:15] Automating production and navigating manufacturing chaos [00:51:11] Why he had to "plead with the government on public TV” [00:53:51] On "eating shit sandwiches” [00:57:30] The COVID mistake that dropped revenue by 85% [01:03:02] Advice for raising a bridge round [01:04:55] How to build fans not customers [01:07:12] How to build in public [01:12:23] Rapid fire questions Where to find Nick Twitter: https://twitter.com/nickywonka Where to find Turner LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/ Twitter: https://twitter.com/TurnerNovak Where to follow The Peel podcast YouTube: https://www.youtube.com/@ThePeelPod Instagram: https://www.instagram.com/ThePeelPod TikTok: https://www.tiktok.com/@ThePeelPodcast Read the transcript: https://www.thespl.it/p/building-a-70-million-chocolate-factory Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Ilir Sela is the Founder & CEO of Slice, the online ordering and all-in-one software platform that helps pizzeria’s manage their business. Ilir started the company in 2010 as MyPizza, rebranded to Slice in 2015, and has since raised over $125 million and supports over 20,000 independent pizza shops. Slice is supported by investors like GGV, KKR, 01 Advisors, Primary Ventures, FJ Labs, and RiverPark Ventures. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/arming-the-pizza-rebels-ilir-sela In this episode we cover - The three reasons small pizza shops are growing 24x faster than big chains - How franchising and "reverse franchising" works - Ilir's biggest mistakes building a franchise business before starting Slice - How to explain a new business model to investors - The customer acquisition benefits of a multi-product model - Bootstrapping Slice to $3 million in profit - Turning down two acquisition offers, one that would have made him nine figures personally - Why MrBeast Burger failed - Why we don't need more cloud kitchens - Empowering entrepreneurs to open their own pizza shops - Building a strong board - Advice for founders selling to small businesses Referenced Cloud Kitchens: ⁠https://www.thefoodcorridor.com/blog/everything-you-need-to-know-about-cloud-kitchens-ghost-kitchens/ Frank Slootman from Snowflake, who Illir said inspires him: ⁠https://www.linkedin.com/in/frankslootman/ Growth in independent pizzerias vs big chains in 2022: ⁠https://www.pmq.com/pizza-power-report-2023/ Jeff Richards from GGV Capital, who invested in Slice and gave Illir some advice mentioned in the podcast: ⁠https://www.linkedin.com/in/jeffrichards/ Michelle Obama on whether pizza is a vegetable: ⁠https://www.youtube.com/watch?v=G14qNHPE4qo&t=21s ⁠ MrBeast’s MrBeast Burger: ⁠https://www.mrbeastburger.com/ The growth of Domino’s stock since 2010: ⁠https://www.cnbc.com/2020/02/25/dominos-stock-yields-higher-returns-than-google-since-ipos.html Slice’s website: ⁠https://slicelife.com/ Where to find Turner Newsletter: https://www.thespl.it/ Twitter: https://twitter.com/TurnerNovak Where to find Ilir: LinkedIn: https://www.linkedin.com/in/ilirsela Twitter: https://twitter.com/ilirsela Timestamps [00:03:34]: The enormous and fascinating pizza industry [00:04:30]: Why there are so many independent pizza shops [00:07:33]: Illir's deep family history with pizza [00:10:43]: What Slice provides independent pizzerias [00:14:21]: The origins of Slice (mypizza.com) [00:16:55]: Building "Nerd Force" before Slice [00:18:22]: How franchises like “Nerd Force” work [00:22:15]: Selling his first company: Nerd Force [00:23:46]: Forming the idea for Slice [00:27:19]: The very first customers [00:32:37]: Turning down $18 million to double down on Slice [00:33:41]: Raising money and starting Slice phase 2.0 [00:39:27]: An acquisition offer that was “tough to say no to” [00:41:55]: Slice's focus now and in the near future [00:45:01]: Why there are so many pizza shops [00:46:46]: Hot takes on Cloud Kitchen and Beast Burgers [00:51:55]: Why online customers are worth 4x more than offline ones [00:53:32]: Why some investors doubted Slice [00:57:58]: The underrated value of a good board [01:00:57]: Advice for founders serving small businesses [01:03:29]: Hitting $500m annual revenue with Slice 3.0 [01:04:31]: Other categories Slice could go after [01:06:25]: Rapid fire questions Read the transcript: https://www.thespl.it/p/arming-the-pizza-rebels-ilir-sela Production and distribution by: https://supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform