In this episode, I sit down with Jason Lavender—a real estate investor and former painting contractor—who gets real about his rocky relationship with money and how Profit First finally changed his life. Jason shares the painful truth about how he ran his business by looking at his bank balance, faced constant stress despite making money, and ignored the warning signs until everything boiled over.

What makes this episode so powerful is Jason’s honesty. He didn’t get it right the first—or even the second—time he tried Profit First. But when he finally committed, delegated implementation, and surrendered access to his own money, everything shifted. We talk about how he transitioned from a chaotic hustle into a clear, structured, and profitable business, and how you can too.

Episode Highlights

[0:00] – Jason’s early years as a painting contractor and the shift to real estate investing

[2:59] – The stress and confusion of “bank balance accounting”

[4:35] – How Profit First didn’t stick the first two times—and what made it click the third time

[5:33] – The critical moment: giving financial control to his assistant (his daughter!)

[8:44] – Going all in on real estate—and leaving the painting business behind

[10:00] – “Burning the ships” and betting everything on building his investment business

[11:28] – Regret and hindsight: How Profit First could’ve helped during his business exit

[14:07] – The turning point question: “Where did all the money go?”

[17:25] – Building a real business, not just a hustle—and the peace that came with it

[21:06] – What a healthy business looks like for Jason today: structure, clarity, protection

[24:07] – The role of coaching and audits in getting brutally honest with the numbers

[29:19] – Final advice for investors stuck in the financial fog

5 Key Takeaways

1. False starts are part of the process. Jason didn’t get Profit First right until he let go of control and got help.
2. Delegating finances can be your superpower. Hiring his daughter to manage the system changed everything.
3. Profit First brings peace. It gave Jason clarity, confidence, and control over his money and decisions.
4. You can’t fix what you won’t face. Financial audits and coaching helped Jason confront what wasn’t working.
5. There’s no shame in getting help. Real transformation happened when Jason stopped trying to do it all alone.

Links & Resources

• Follow Jason on Facebook: https://www.facebook.com/jason.lavender.787084
• Check out Elevate Mentoring: https://elevatementoring.coach
• Need help implementing Profit First? Book a call: https://www.simplecfo.com

If this episode hit home, don’t forget to rate, follow, and review the show. And share it with someone who’s tired of the hustle and ready to get financially healthy—for good.