7FF 291: What Mike learned from hiring (and firing) 2 C.O.O.’s who DIDN’T work out…

November 7, 2019

About This Episode

We learn more from failure than we do from success.


So today, let’s talk about a couple times where things went WRONG…


Over the past 2 weeks, I’ve been sharing a lot about building your team, working with a COO (Chief Operating Officer) to grow your real estate investing business, and how to be an effective leader.


Not everyone is ready for this level of growth yet…


…but if your goal is to scale up your income and your impact, this stuff is important.


I believe every business owner SHOULD consider bringing on a COO when the time is right.


Your COO is the person who “replaces” you as the day-to-day manager of your company and frees up your time so you can serve as the “visionary” leader your team needs.

But it isn’t all sunshine and roses.


As you can probably imagine, hiring someone to run your ENTIRE business is complicated.


My good friend Mike Simmons has tried to hire a COO twice…


…and both times, it didn’t work out.


But Mike learned some big lessons along the way that have made him a better leader.


And I’ve brought Mike on the podcast today to share what happened so you’ll know a bit more about what to do and what not to do when hiring a COO (or when hiring anyone, really).


Let’s dive in!

Free Resources / Downloads

5F Framework

A business framework that creates consistency within your flipping business by giving you a tested roadmap to building real estate wealth.
5 Proven Steps to Build Active and Passive Income in Real Estate (FREE!)

Get Access Now

Freedom Number Calculator

The 2-Minute Exercise That Shows You Exactly How to Build Toward Your Life of Freedom.This quick (and powerful) quiz will help you calculate exactly how many deals you need to support your ideal lifestyle and how close you already are. Most investors don’t fail from lack of effort, they fail from lack of direction. No guesswork. No fluff. Just a clear target—and a plan to make it real.

Get Access Now

Adam Whitney’s Seller Call Script

Use the same script Adam uses while on the phone with sellers

Get Access Now

Off-Market Deals on Demand

Get the UltimateOFF-MARKET DEALS Starter Pack...For FREE! Niche lists, seller strategies, a hyper-local market tracker, and a bonus!

Get Access Now

Grow Your House Flipping / Wholesaling Business WITHOUT Guesswork or Trial-and-Error

Find out EXACTLY what you need to be working on TODAY to do more deals, make more money, and free up your time.

Explore More Episodes...

7FF 821: How to Use Hard Money Loans to Fund Your Next Flip

September 18, 2025

Lender Melissa Korda, who’s funded over $118M in investor deals, breaks down the truth about hard money. She reveals how to become instantly lendable even on your very first deal and why building a relationship with a lender before you need money is the smartest move an investor can make.

Full Episode >

7FF 820: How I Scaled My Revenue to $2M Per Year

September 16, 2025

Adam Whitney breaks down how he scales his real estate marketing to $2M a year using disciplined marketing systems and the CEO Framework. This number isn’t just about revenue…it’s about creating financial freedom, security, and time with his family.

Full Episode >

7FF 819: The story I never wanted to tell (but had to)

September 11, 2025

I’ve carried this story for 20 years. This is how a broken childhood and near-prison sentence became the foundation for a $45M portfolio and a life of freedom.

Full Episode >

7FF 818: How to Earn on the Same Dollar Twice with the “Tank” Strategy

September 9, 2025

Adam sits down with Tom Laune from Bulletproof Wealth to explain how a special kind of life insurance can protect your family, grow your money, and still give you cash to use on real estate deals.

Full Episode >

7FF 817: From Door-to-Door Salesman to Full-Time Flipper

September 4, 2025

Matt Foote went from selling roofs door-to-door to flipping houses full-time. With just $800 in SMS marketing, he closed his first $24k deal…and now he’s done 100+ flips. His story proves success comes from action, not waiting.

Full Episode >

7FF 816: The #1 Currency in Real Estate

September 3, 2025

Adam sits down with Dr.Sheri who reveals the real currency in real estate.And why it’s not money. Adam shows how it runs through every deal you do..

Full Episode >

Ready to Build a Business That Finally Works?

Ready to find your tribe?

Don’t stay stuck in chaos or settle for another year of inconsistency. Join a serious community of operators who are building businesses that matter. This is your moment.

Click below and we’ll help you determine which program is the best fit for you.