Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found ... Show More
Dec 10
Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a distinctly long game in one of the most entrenched markets in technology ... Show More
1h 14m
Nov 19
How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)
Jyoti Bansal is the co-founder and CEO of Harness, the software delivery platform used by thousands of engineering teams, and previously founded AppDynamics, which he led from inception to a multibillion-dollar acquisition by Cisco. In this episode, Jyoti unpacks what it really t ... Show More
1h 5m
Oct 2025
Go hard early: How lessons from Verkada shaped Serval's AI agents for IT teams | Jake Stauch (Founder and CEO)
Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the compa ... Show More
1h 23m
Dec 2024
Why great AI products are all about the data | Shaun Clowes (CPO Confluent, ex-Salesforce, Atlassian)
<p><strong>Shaun Clowes</strong> is the chief product officer at Confluent and former CPO at Salesforce’s MuleSoft and at Metromile. He was also the first head of growth at Atlassian, where he led product for Jira Agile and built the first-ever B2B growth team. In our conversatio ... Show More
1h 21m
Nov 9
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel
Jen Abel is GM of Enterprise at State Affairs and co-founded Jellyfish, a consultancy that helps founders learn zero-to-one enterprise sales. She’s one of the smartest people I’ve ever met on learning enterprise sales, and in this follow-up to our first chat two years ago (coveri ... Show More
1h 21m
Jul 2025
Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo
Maor Shlomo is the founder of Base44, an AI-powered app builder that he bootstrapped to an over $80 million acquisition by Wix in just six months. As a solo founder (with severe ADHD), he hit $1 million ARR just three weeks after launch and grew the product to more than 400,000 u ... Show More
1h 31m
Sep 2025
$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder)
Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for ... Show More
1h 37m
Jul 2025
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)
Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $ ... Show More
1h 28m
Jul 2024
Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead)
<p><strong>Jeff Weinstein</strong> is a product lead at Stripe, where he helped grow their payment APIs to hundreds of billions in volume and transformed the way founders start companies into a few simple clicks with Atlas. Prior to Stripe, Jeff led several startups and sold comp ... Show More
2h 35m
Oct 2024
E105: Ryan Serhant: How Successful Entrepreneurs Manage Time (1,000 Minute Rule)
David Weisburd speaks with Ryan Serhant, founder and CEO of Serhant, about the explosive growth following the Netflix debut of *Owning Manhattan*. They discuss how the show has transformed the business, increasing market diversification, website traffic, and lead engagement. Ryan ... Show More
39m 52s
Jul 2025
566: Silicon Valley's CEO Whisperer on Why Most Startup Founders Fail (with Rich Hagberg)
<p dir="ltr"><strong>Rich Hagberg</strong>, often referred to as "Silicon Valley's CEO Whisperer, psychologist and co-author of Founders Keepers, has advised over 1,000 executives and founders. In this conversation, he outlines why most startup leaders fail, and what the data rev ... Show More
56m 43s