141: Managing People as a Fast Growth Startup with Katelyn Gleason of Eligible.com

141: Managing People as a Fast Growth Startup with Katelyn Gleason of Eligible.com

At 23, Katelyn Gleason faced, like many people in their early 20s, an existential crisis. She just didn't know what she wanted to do. "I started thinking about jobs. I was like 'God if I'm going to have to do this for the rest of my life it better be something I really care about, that can be my life's work, that I can really invest all of my time and all my energy into,'" Gleason says. Her first step was to start reading the biographies of some of the greatest individuals in human history—Marie Curie, Jane Austen, Abraham Lincoln, anything she could get her hands on. Gleason's goal was to learn as much as she could about these great people and how they managed to leave such a large legacy and imprint on humankind today. It wasn't long before Gleason found herself immersed in the world of healthcare, technology, and startups. It was there she found her purpose. Gleason noticed a problem in the medical industry that no one seemed to be talking about or trying to solve. Doctors and patients alike were getting bogged down with paperwork that was often confusing, and as a result, many were dealing with huge costs simply by filling out the wrong forms. The next nine months were spent at her kitchen table, furiously working on a solution to this problem. That solution would end up becoming Eligible, a medical billing startup designed to make it as simple as possible for doctors and insurance companies to work together and save everyone money, patients, doctors, insurance companies alike. As a two-time alumni of Y-Combinator, Gleason led Eligible from quietly testing and validating its product to becoming an explosive fast-growth company. Today, Eligible processes 14 million transactions per month, with a projected 50 million transactions by the end of the year, and has raised more than $25 million in funding. In this week's episode you will learn: Every step you need to take as the founder of a startup, from validating to raising capital How to gain proof of concept as quickly as possible Where to find co-founders to complement your own skills and talents What strategies you can use to build a fast-growth company How to manage the people around you and keep them focused on your goal & much more!

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614: (Solo) Running on Fumes? Reset Your Mindset Before The Year Ends

614: (Solo) Running on Fumes? Reset Your Mindset Before The Year Ends

If you’re dragging yourself toward the end of the year feeling exhausted, overwhelmed, and mentally drained, you’re not alone. This is one of the toughest stretches for founders — you’re still runni...

16 Joulu 20259min

613: Why Most Beauty Brands Fail - and How to Beat The Rest | DIBS Beauty Founder

613: Why Most Beauty Brands Fail - and How to Beat The Rest | DIBS Beauty Founder

DIBS Beauty went from zero to one of America’s fastest-growing makeup brands in just four years, with founder Jeff Lee scaling the business into the mid–8 figures and landing a top spot on the Inc. ...

11 Joulu 202552min

612: (Solo) Funding vs Bootstrapping - The Real Tradeoffs EVERY Founders Needs To Know

612: (Solo) Funding vs Bootstrapping - The Real Tradeoffs EVERY Founders Needs To Know

Should you raise money or bootstrap your business? It’s one of the biggest questions every founder faces — and the wrong decision can shape the entire future of your company. In this episode, I share...

9 Joulu 202512min

611: From Homeless to Multi-Billionaire - His Success Habits | John Paul DeJoria

611: From Homeless to Multi-Billionaire - His Success Habits | John Paul DeJoria

John Paul DeJoria went from being homeless twice to building two global billion-dollar brands, Paul Mitchell and Patrón Tequila, using nothing but resilience, sales mastery, and a refusal to quit. ...

4 Joulu 202559min

610: (Solo) The Secret to Finding Agencies That Don’t Burn You

610: (Solo) The Secret to Finding Agencies That Don’t Burn You

When you’re just starting out, the fastest way to grow isn’t automation, ads, or scaling systems — it’s doing things that don’t scale. In this episode, I share why the most successful founders — fr...

2 Joulu 20259min

609: From $0 to $20M in 3 Years Selling Suppliments | Damien Fitzpatrick

609: From $0 to $20M in 3 Years Selling Suppliments | Damien Fitzpatrick

From professional rugby player to successful entrepreneur, Damien Fitzpatrick built a sports recovery brand trusted by elite athletes around the world. In this interview, Damien shares how he went...

27 Marras 20251h 4min

608: (Solo) Why Short-Term Wins Can Quietly Kill Your Business

608: (Solo) Why Short-Term Wins Can Quietly Kill Your Business

When I first started Foundr, I made a lot of short-term decisions — and most of them hurt us more than they helped. It took years (and a few hard lessons) to understand that sustainable growth only co...

25 Marras 202510min

607: How I Built a $120M/Year Cookie Business From My Appartment | Loren Castle

607: How I Built a $120M/Year Cookie Business From My Appartment | Loren Castle

Loren Castle turned a life-threatening cancer diagnosis at 22 into the spark that built Sweet Loren’s, a $120M-a-year clean food brand now sold in over 5,000 supermarkets nationwide. In this inter...

20 Marras 202551min

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