More or Less

Seven years after Slow wrote its first check, Sam sits down with Teamshares CEO Mike Brown as the company prepares to go public. Mike’s core insight is simple: America has millions of durable, cash-flowing small businesses, but no great long-term owner. After buying and operating electrical contractors himself, he realized the opportunity wasn’t another marketplace or PE roll-up, it was building a permanent holding company that acquires great businesses, gives employees ownership, and never sells. Today, Teamshares owns 92 businesses generating roughly $60M in EBITDA. The conversation explores why most roll-ups fail, why capital allocation is the true operating system of the business, and why the traditional private equity model may be running out of steam. Mike closes with an ambitious goal: grow corporate EBITDA from $19M to $100M by 2027 and create a forever home for thousands of small businesses.Chapters00:00 Episode Teaser Featuring Mike Brown, Teamshares CEO01:11 The Teamshares Origin Story04:48 From Wall Street to Buying Small Businesses10:47 Why Going Direct to Sellers Didn’t Work (The FSBO Problem)13:18 Buying at Scale, The Teamshares Model15:27 92 Acquisitions and $60M EBITDA, Lessons Learned18:26 Why Generalist Hires Didn’t Work19:08 Building a Leadership Pipeline23:46 The Internal YC, Community Across Portfolio Companies27:42 How Technology Powers 92 Businesses28:08 “Will This Business Exist in 50 Years?”32:21 Why Most Roll-Ups Fail37:30 The Road to $100M EBITDA39:51 The Long-Term Vision40:58 Capital Allocation as a Competitive Advantage42:34 Decentralized Leadership, Centralized Capital46:16 Why Private Equity Fails Small Businesses49:25 Going Public, What Comes NextWe’re also on ↓X: https://twitter.com/moreorlesspodInstagram: https://instagram.com/moreorlessYouTube: https://youtu.be/3tV4wdtZBukConnect with us here:1) Sam Lessin: https://x.com/lessin2) Dave Morin: https://x.com/davemorin3) Jessica Lessin: https://x.com/Jessicalessin4) Brit Morin: https://x.com/britImportant Disclosures and Disclaimers:Teamshares has entered into a definitive agreement for a business combination with Live Oak Crest Acquisition Corp. (“Live Oak”), a special purpose acquisition company. In connection with the proposed transaction, a registration statement on Form S-4 (the “Registration Statement”) has been filed with, and been declared effective by, the U.S. Securities and Exchange Commission (the “SEC”). This podcast does not constitute an offer to sell or the solicitation of an offer to buy any securities. For important information about the proposed transaction, including where to find the Registration Statement and other legal disclaimers, please refer to the press release available at https://www.businesswire.com/news/home/20260527344175/en/Teamshares-Announces-S-4-Effectiveness-in-Anticipation-of-Nasdaq-Listing.Clarifications:Teamshares currently has 93 operating subsidiaries. Additionally, Teamshares has had documented revenue declines and business closures. A full reconciliation of non-GAAP measures to the most directly comparable GAAP measures, as well as Teamshares’ audited GAAP financial statements, is available in the Registration Statement. Investors should review the full set of assumptions and risk factors accompanying these metrics in the Registration Statement.

We're recording this from Jackson Hole after three days of wheeling and dealing—and yes, canceling meetings for powder. This week we're going deep on OpenClaw. The meetup had 1,500 people show up (Kevin Rose, Marissa Mayer, Ashton Kutcher were some notable guests). And now we're all spending thousands of dollars a month on AI agents we've named after Friends characters while debating whether "developer" is even a job title anymore.We talk about:•⁠ ⁠Why founders are working 24/7 and possibly burning out•⁠ ⁠The decentralized AI future (and why it's not great for OpenAI)•⁠ ⁠Dark software factories where only agents write code•⁠ ⁠Whether everyone's jobs are about to disappear (spoiler: we disagree)•⁠ ⁠The SaaS-pocalypse coming for legacy software•⁠ ⁠Personal AI sovereignty and why Apple's just sitting back laughingAlso: Google's CC assistant is… fine? And we have strong opinions about Heated Rivalry.Chapters:0:00 - Intro: Skiing in Jackson Hole2:30 - Conference Takeaways: Founders Are Working Relentlessly 7:15 - AI Burnout & the 24/7 Work Cycle12:40 - Naming Your AI Agents (Friends Edition)15:20 - How Much Are You Spending on Bots?18:45 - Google CC Assistant Review22:10 - OpenClaw Meetup: 1500 People Show Up28:30 - What Even Is a Developer Anymore?35:50 - OpenAI vs Decentralized AI: The Big Debate42:15 - Personal AI & Data Sovereignty47:20 - Dark Software Factories & Agentic Engineering52:10 - Are All the Jobs Going Away?55:40 - The SaaS Apocalypse58:20 - Pop Culture: Heated Rivalry, Nancy Guthrie Case, StrangersWe’re also on ↓X: https://twitter.com/moreorlesspodInstagram: https://instagram.com/moreorlessYouTube: https://youtu.be/KUA7ue5vB1EConnect with us here:1) Sam Lessin: https://x.com/lessin2) Dave Morin: https://x.com/davemorin3) Jessica Lessin: https://x.com/Jessicalessin4) Brit Morin: https://x.com/brit

Jessica is back from Davos and is recapping her highlights on the pod this week. If you’re a loyal podcast ‘viewer’, you’re in luck because Jess also brought photos from a recent Grace Cathedral sound bath visit before she dives deep into the Clawdbot/Moltbot/agentic moment. Dave is all in on what’s to come in this new age of agentic computers, and in true Sam fashion, he is less impressed by the technology and suggests that if the trend continues, it’s going to be bye bye internet. In the land of the other ‘mature’ AI companies, Jess recaps her Davos AI infra panel’s red-pill take on AI with the killer quote of the week: “the appetite for intelligence is limitless.” But how true is all this demand and how much of it is really narrative? Could the rise in gold and silver prices really be a sign of technology shorting? The crew also reacts to the Minneapolis situation, debating whether it’s a scaling issue at ICE or a political move. Chapters:00:30 — Jess Returns From Davos: No Snow, All SXSW Energy 03:40 — Grace Cathedral Sound Baths06:25 — Moltbot Heat Spike: Are AI Agents Ending the Internet? 17:29 — Moltbot Has no Moat; Founders Should Be Memorable Instead21:26 — Inside the Davos AI Panel: CoreWeave, G42, OpenAI & BlackRock’s Red Pill 29:47 — Minneapolis, ICE, and How the Valley Is Reacting 51:03 — The AI Chatbot Trap for Retail (And Why Everyone Will Fall for It) We’re also on ↓X: https://twitter.com/moreorlesspodInstagram: https://instagram.com/moreorlessYouTube: https://youtu.be/OZDFAvRq7GcConnect with us here:1) Sam Lessin: https://x.com/lessin2) Dave Morin: https://x.com/davemorin3) Jessica Lessin: https://x.com/Jessicalessin4) Brit Morin: https://x.com/brit

AI, AI, and more AI. Do you even live in Silicon Valley if you’re not talking about it every episode? This week, we go deep on how open-source vibe-coding tools are starting to replace the need for traditional SaaS contracts. Dave shows (and tells) how he used the open-source “Claude bot” to reverse-engineer his Mural photo frames and spin up a better web UI in under 30 minutes. Brit test-drives Anthropic’s new Cowork, auto-mapping the entire seed VC market while it runs her browser, and celebrates how much these agents are boosting household productivity. Sam loves the power but calls local agents a massive security backdoor, argues trust will consolidate with Apple and Google, declares that “software is not a business,” and announces we’ve officially entered the fart-app era of AI toys. Jessica flags rising panic among SaaS vendors. Don’t miss Sam’s hot-chick analogy and Brit’s Pop Corner to close it out 😉Chapters:02:05 Vibe coding week: Anthropic's Claude Code & Cowork05:25 Dave's Reverse-engineering Mural frames08:30 AI Agents as a security nightmare12:03 AI’s Napster moment18:43 Software is no longer a defensible business24:00 Sam's investing: Quiet AI businesses or narrative ownership29:27 Offline's Seed alpha in illegible spaces33:06 When will platforms start to block APIs and protect their business?35:27 Shopify Founder and CEO, Tobi's Tweet on modern UI for MRI reading 43:34 GLP-1s & grocery spend45:06 The Information's Wealth tax poll result48:55 We're in the fart-app era of AIWe’re also on ↓X: https://twitter.com/moreorlesspodInstagram: https://instagram.com/moreorlessYouTube: https://youtu.be/2q99bDO-a1EConnect with us here:1) Sam Lessin: https://x.com/lessin2) Dave Morin: https://x.com/davemorin3) Jessica Lessin: https://x.com/Jessicalessin4) Brit Morin: https://x.com/brit