Jacob Bailey
Jacob is the CEO of Summit Maids, a rapidly growing people-first commercial and residential cleaning business based in Cleveland, Ohio. Previously, Jacob has led growth efforts at several venture-backed tech…
Starting a company is an act of unreasonable optimism. The founders in this section know that firsthand. They’ve built startups across every industry. Some that worked, some that pivoted, and some that taught very expensive lessons. All of it is here.
These interviews cover the full startup arc. The spark of an idea. The terrifying moment you actually commit to it. The scramble for funding, customers, and some version of product-market fit that doesn’t feel like a hallucination. Then the scaling part, which introduces a whole new set of problems nobody warned you about.
What’s useful about these conversations is the range. Solo founders. Co-founder duos. People who raised venture capital and people who think venture capital is a trap. Bootstrap devotees and serial fundraisers. There’s no single right way to build a startup, and reading enough of these interviews makes that abundantly clear.
You’ll find practical insights on lean methodology, customer acquisition, team building, and the art of staying alive long enough to figure out what works. Also the emotional side, because startups are emotional. Anyone who says otherwise is either lying or hasn’t started one yet.
Jacob is the CEO of Summit Maids, a rapidly growing people-first commercial and residential cleaning business based in Cleveland, Ohio. Previously, Jacob has led growth efforts at several venture-backed tech…
Jeff Hillam is the CEO of Red House Medical Billing, a company that provides revenue cycle management services, including payroll and bookkeeping. Jeff has also co-founded Lighthouse Health and founded…
Gboyega Adebayo is on a mission to demystify entrepreneurship and help every person start their dream side hustle or business. Gboyega is the CEO & Co-Founder of Yencil, a platform…
Born and raised in Mumbai, Sneha earned her MBA at IESE Business School in Barcelona where she also became a WSET Level 2 wine sommelier. Sneha is the co-founder &…
Matt McCormick’s 8th grade algebra teacher, Mr. Eisenreich, told him that someone who likes math should, “Become an engineer.” So that’s what he did. He graduated from the University of…
Adam Sandman has been a programmer since the age of 10. Adam is the Founder and CEO of Inflectra – a leading maker of software test management, application lifecycle management,…
Dr. Nicolas Stephan is co-founder of the startup Sparrks, which he started with Jakob Hansen early 2021. With Sparrks, companies develop their talents and leaders effectively and with lasting impact…
Fernando Pessagno is an Argentinian product designer currently based in Sweden. He is the founder of ResumeMaker.Online, a resume maker tool that has helped more than one million non-tech-savvy users…
Lasse is a purpose driven serial entrepreneur. While pursuing his purpose of improving the lives of millions of people in a significant and positive way he founded several companies such…
Philippe Lehoux is the CEO of Missive, a shared inbox and team chat app for businesses. He has been bootstrapping internet businesses for the last 24 years. He has done…
Ron Gutman is an inventor, investor and serial healthcare and technology entrepreneur, and a Stanford University adjunct professor. He holds a series of patents in AI and Healthtech and won…
Michal Klodner is a founder & CTO of innovation path, a meaningful way to provide robotic business process automation solutions. Under his leadership, innovation path help clients such as Veolia…