Why He Left a Decade at Forbes to Build Upstarts From Scratch - Alex Konrad - Upstarts - EP#116

Most founders think the best story wins. Alex Konrad has spent 15 years watching what happens when the story is all there is. In this episode, Alex Konrad, Founder of Upstarts Media, joins me to share what he's learned from covering the biggest names in tech. He spent more than a decade at Forbes writing cover stories on people like Marc Benioff and the Collison brothers, ran the Midas List for ten years, and co-created the Cloud 100. In February 2025, he left to build Upstarts Media on his own. From the one trait he sees in the most successful founders to why great storytelling can make or break a company, Alex unpacks what he's learned from watching thousands of founders and investors up close. We also get into the loneliness of being a solo founder, the customer stories that stay with you, and what it takes to build a bootstrapped media company. If you're building a company, raising capital, or wondering whether you're built for the founder journey, this conversation will change how you think about obsession, storytelling, and what actually lasts. Key Takeaways: - The Obsession Is the Real Qualifier: The most successful founders Alex has interviewed aren't building for wealth or Twitter popularity. They're almost sick in the head about the work, and they couldn't live with themselves doing anything else. Alex explains why the founders chasing the lifestyle, the YC badge, or the title tend to burn out faster. - Find Your One Superpower: Early on, a founder should be able to do one thing better than anyone they could hire. For Alex, it's storytelling. For me, it turned out to be motivating people. - Storytelling Should Accelerate the Story, Not Be the Story: If you're a great salesperson selling magic beans, it catches up to you eventually. - What Great Investors Actually Do: After a decade on the Midas List, Alex says the number one thing CEOs want is an investor who feels like part of the team. - Great Founders Find Great Markets: Silicon Valley says a great founder can't fix a bad market. Alex isn't so sure. With how many companies pivot in the AI era, he believes a great founder will evolve into the market, or prove everyone wrong about how big it was. - Online Can Build a Brand or Eat Your Day: Alex recently wrote about CEOs and investors who are highly online to terminally online. We talk about the real advantage of a public brand, the risk of the doom scroll, and why he suggests putting your time on social media on the calendar. Quote of the Show: "Storytelling should accelerate your story, for good and bad. It shouldn't be the entire story." – Alex Konrad, Founder, Upstarts Media Guest Featured in This Episode: Alex Konrad, Founder, Upstarts Media LinkedIn: https://www.linkedin.com/in/alexrkonrad/ Upstarts Media: https://www.linkedin.com/company/upstarts-media/ We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode. Chapters: 00:00 - Intro 02:01 - How Alex decides who to cover 11:37 - Why Alex left Forbes to build Upstarts 17:52 - The number one trait of successful founders 19:56 - Founder cycles and finding your one superpower 27:05 - The Midas List and what makes a great investor 34:35 - Storytelling and the trillion-dollar outcome 40:23 - Building Upstarts solo and bootstrapped 42:14 - The loneliness of being a solo founder 44:26 - Crazy customer stories and "Elon-level" security 49:16 - Terminally online founders 54:59 - Where Upstarts is in three years