At 19, Markus Villig borrowed €5,000 from his parents to fix Estonia's broken taxi system. What happened next defied every conventional startup playbook.
Markus started by making fleet dispatch software for local taxi companies. But when it became clear they weren’t embracing the on-demand revolution, he pivoted the business to ride-hailing for drivers, co ... Show More
Dec 4
Palo Alto Networks ft Nir Zuk & Nikesh Arora - The Grudge That Transformed Cybersecurity
In the early 2000s, the cybersecurity industry was dominated by incumbents focused on high margins, not innovation. Nir Zuk tells the story of how, frustrated by this stagnant culture, he set out on his own with a radical idea: the Next-Generation Firewall. His vision was to unif ... Show More
47m 3s
Oct 23
Zipline ft Keller Cliffton - Reinventing Delivery with Instant Drone Transport
In 2014, Keller Cliffton made an audacious pivot: shut down his robotic toy company and rebuild it as an autonomous drone delivery system for life-saving medical supplies. Investors were skeptical: The team knew nothing about drones, healthcare, or logistics. But they pushed forw ... Show More
45m 55s
Jul 2016
Acquired Episode 15: ExactTarget (acquired by Salesforce) with Scott Dorsey
Ben and David return to make their first foray into enterprise software, covering Salesforce’s $2.5B acquisition of ExactTarget in 2013 with the help of special guest and ExactTarget cofounder & CEO, Scott Dorsey. Technical note: due to an issue we didn’t catch during recording, ... Show More
1h 18m
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
Mar 2025
Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder)
<p><strong>Ivan Zhao</strong> is the co-founder and CEO of Notion. Ivan shares the untold story of Notion, from nearly running out of database space during Covid to finding product-market fit after several “lost years,” and the hard-won lessons along the way.</p><p>—</p><p><stron ... Show More
1h 12m
Mar 2025
The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic)
<p><strong>Matt Mullenweg</strong> is the co-founder of WordPress, the open source platform powering a staggering 43% of the internet. He also serves as CEO of Automattic—the parent company of brands like WordPress.com, WooCommerce, and Tumblr—which is worth over $7 billion, with ... Show More
1h 34m
Apr 2025
How a New Solo Lawyer Built a Thriving Practice in Just 3 Months | First Flight #3
Starting a law firm straight out of school? Meet Philip Mauriello, an attorney who wasted no time launching his solo practice just three months after passing the bar. In this episode, host Adriana Linares revisits her conversation with Philip, who shares the smart, scrappy strate ... Show More
43m 21s