In this episode, I reconnect with my friend and client Bill Kenny, who shares his powerful transformation from grinding through dozens of flips and transactions a year to building a more sustainable and scalable business. Bill opens up about how burnout pushed him to pivot into commercial real estate and start his own hard money lending company, Jump Capital.
We unpack how he transitioned from being in the trenches to funding deals for others, and how implementing Profit First (with help from Simple CFO) gave him the clarity and structure to grow with confidence. If you’ve ever wondered when it’s time to level up your strategy—or how to lend without losing sleep—this episode has the roadmap.
Episode Timeline Highlights
[0:00] – Introduction
[1:11] – Bill shares what he’s seeing in the current Mid-Atlantic market
[3:36] – From flipping and wholesaling to launching a hard money lending company
[5:49] – The moment burnout hit and Bill decided to shift toward commercial and passive income
[7:14] – Why lending felt like a natural next step—and how they approached it as operators
[8:53] – Lending criteria, target deals, and markets Jump Capital focuses on
[11:06] – What sets Jump Capital apart: partnership mindset and in-the-trenches experience
[13:01] – How they help new investors avoid costly mistakes and bad deals
[14:28] – Growth goals: Doubling annually and managing millions in active loans
[17:06] – The real impact of working with Simple CFO and fixing messy books
[20:34] – Advice for investors in today’s shifting markets
[22:58] – When to consider transitioning into lending or commercial investing
5 Key Takeaways
Links & Resources
If you’re ready to move from chaos to clarity, or want to work with a lender who truly understands your journey, this episode is for you. And if you enjoyed it, please rate, review, and follow the show. Your feedback helps us reach more investors ready to build profitable, purposeful businesses.