Practical Founders Podcast

#6: Self-funded 3rd venture to a big exit in 18 months - Steve Gelley

29 Jul 2022

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Steve Gelley created two successful businesses and learned important lessons before he and a cofounder self-funded a third startup that was acquired in only 18 months for a big prize. Steve started his entrepreneurial journey by buying, improving, and then selling CPA accounting services firms in the Eastern U.S. Then he grew his first VC-funded tech startup, Xendoo, to innovate in the small business accounting services space. He exited Xendoo and worked with a partner to fund and create a new startup called wemlo to automate the manual process of processing mortgage loans for mortgage brokers. Only 18 months from starting, including four strategic pivots, Steve and his cofounder, David Rogove, sold wemlo to a strategic buyer owned by RE/MAX. Steve says, "Nobody tells you that founders end up spending so much time on funding and the optics of the dog and pony show that no one's running the business. It's actually counterproductive." In this episode, Steve explains: Why he sold his interest in his first startup when the company achieved its first VC funding How he and his cofounder built a market-leading solution for a massive industry with a small team What the true opportunity cost of raising VC funding is for founders growing vertical software companies The simple math that showed him raising big funding would not be better for the founders What it takes to design revolutionary software with automated processes that revolutions Why he says "timing is the luck factor in a business," especially when you exit a business Why money from investors won't solve all your problems and often make things worse Check out all our episodes and articles at https://practicalfounders.com.

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#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head

26 Dec 2025

Practical Founders Podcast

Practical Founders Podcast

#6: Self-funded 3rd venture to a big exit in 18 months - Steve Gelley

This episode hasn't been transcribed yet

Other episodes from Practical Founders Podcast

#176: The Five Questions That Will Decide Your SaaS Progress Next Year - Greg Head

#175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh

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