Why My Real Estate Company Didn’t Collapse When I Did with Mike Webb

In this episode, I sit down with Mike Webb—firefighter, real estate investor, and co-founder of Jump Capital—to talk about the moment life forced him to stop… and how it reset everything. After a terrifying medical event took him out of commission for months, Mike shares what it taught him about being intentional, building a real business (not just a job), and why profit without purpose means nothing.

We get into how his business survived without him, the power of partnerships, and how Profit First helped him and his partner Bill Kenny finally pay themselves on purpose. Whether you’re chasing financial freedom or just trying to stop the entrepreneurial chaos, Mike’s story is a powerful reminder of what matters most.

[Timeline Summary]

[0:00] – Introduction

[1:09] – Mike’s dual identity: firefighter and financial freedom builder

[2:36] – A sudden brain bleed, ICU stay, and a forced five-month reset

[5:21] – Why their business didn’t collapse—and how they built it to survive

[8:10] – The “wild card” test: how Bill stepped up when Mike was down

[13:18] – From flippers to lenders: their pivot into more sustainable income

[16:00] – What finally pushed them to hire a CFO and how it changed everything

[18:46] – Profit First in action: going from random paydays to intentional salaries

[22:32] – Building a business you can run with a laptop and a phone

[26:24] – The real “why” behind it all: Mike opens up about fatherhood, family, and legacy

[32:05] – Where to find Mike, and why you should follow his journey

Links & Resources

• Mike’s lending company: Jump Capital
• Learn more or book a CFO: SimpleCFO.com

If this episode hit home for you, do me a favor—rate, follow, and share this podcast with someone who needs it. And don’t forget to leave a review if you got value from today’s conversation.