Russ Heddleston built DocSend from a simple idea into a $165 million exit to Dropbox. But the story isn't about overnight success or massive funding rounds. It's about research before building, pricing that actually makes sense, content marketing powered by unique data, and knowing when money isn't the bottleneck anymore. This is the playbook for building a horizontal B2B SaaS company the right way: patient, profitable, and strategic.

Sarah Mausolf built Winnie, a $212 billion marketplace that connects parents with daycare and preschool providers across the United States. This is her story of going from MIT math major to Google product manager to startup founder, navigating the challenges of raising $9 million as a female founder in an 'unsexy' space, building supply before demand, and creating a platform that's become the default search tool for childcare. She shares the reality of cofounding while parenting through cancer, illness, and multiple pregnancies, the pivot from a failed Yelp-for-parents concept to a focused childcare marketplace, and why keeping the product free for parents while monetizing providers is the only model that makes sense.

Lee Zlotoff went from secretary to Hollywood writer in a single conversation, created MacGyver by removing one key element, and developed a three-step creativity system that became faster than any writer in the industry. This is the story of how audacity, a chocolate bar, and paper models built a global phenomenon—and a problem-solving method anyone can use.

Will Schroter started his first company at 19, building websites for Mastercard and BMW in 1994 when almost no one knew what the internet was. He scaled that agency to $65 million in billings, landed a $250 million Prozac account, and sold in 2001 at age 27. Then he tried running six companies simultaneously in an incubator model, which nearly killed him—literally ending up in the ICU with a stopped heart from a massive anxiety attack. After that reset, he launched Startups.com, a unified platform helping founders with everything from business planning to funding to virtual assistants. Now he runs one company with 200 people across multiple product lines, works eight-hour days, and plans to do this for the rest of his life.

In this special episode, I'm releasing three interviews I did with Tim Ferriss over the years. We cover his journey from building his first supplement business to becoming the author of The Four Hour Workweek, plus his methods for learning any skill rapidly. This is Tim before he became the famous podcaster and investor most people know today.

Sonia Petkovich built MeowTel, the number one cat sitting app in the US, from a side project during her MBA to a profitable company serving over 10,000 customers across 150+ cities. This is the story of how she pivoted from 'Airbnb for cats' to 'Uber for cat sitting,' survived COVID after raising her seed round just weeks before lockdown, and built a two-sided marketplace while still doing cat sits herself as CEO. She shares hard-won lessons about raising money, building MVPs, managing supply and demand, and why she might never raise a Series A.

Paul Biggar never wanted to be a CEO. He's a compiler nerd who built CircleCI, now valued at $1.7 billion, by solving a problem he saw at Mozilla. After stepping down when the company was worth just $20 million, he's now working on Darklang, an even more ambitious project to eliminate cloud complexity. This is the story of how a technical founder built a unicorn, knew when to step aside, and is now funding his next moonshot by selling equity in the company he no longer runs.

Todd Garland built BuySellAds from a basement apartment into a $10+ million advertising platform. This is his complete origin story: from selling his dad's stereo at impromptu yard sales to washing dishes in high school, from dropping out of college after losing both parents to building websites as a freelancer. You'll learn how he coded the first version while working full-time at HubSpot, why he let the finished product sit for six months out of fear, how he hit $5,000/month in his second month, and why he chose 25% as the revenue share (it's the minimum viable number). This interview captures Todd at the inflection point, running a distributed team of 13 people across multiple countries, still hustling despite eight-figure revenue, and preparing to launch his first new product after five years of marketplace-only growth.

In this episode, I sit down with Dan Young, who went from juvenile detention to building multiple computer hardware empires and closing over $600 million in property deals. Dan shares his unconventional path from selling Ginsu knives at swap meets to founding PC Laptops and Xydax PCs, plus the investment strategies that built his wealth.

A deep dive into Tiliter, a computer vision startup that began by scanning produce in grocery stores and is now expanding globally. This article explores founder Marcel Hirsch's journey from welding steel prototypes in a garage to deploying systems in hundreds of stores worldwide, the technical and business challenges of hardware startups, why investors initially rejected retail hardware, and the company's vision for democratizing computer vision technology beyond groceries.