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 791: He Started with Nothing—Now He’s Raised $400K+ Private Capital

May 29, 2025

Dairius Kawewehi shares his journey from the foster care system to the U.S. Navy, and now to real estate investing. Learn how he embraced discomfort, found purpose through trauma, and leaned into community to grow his business and life.

Full Episode >

7FF 790: 90% of Millionaires Built Their Wealth THIS Way

May 27, 2025

Adam Whitney breaks down the #1 wealth-building strategy behind 90% of millionaires. He shares real stats, his personal take on why most people overlook it, and what you can do to start building long-term wealth.

Full Episode >

7FF 789: Breaking Down Our 13X Return On Direct Mail Marketing

May 23, 2025

In this episode, I break down the direct mail campaign that generated over $486K in revenue while coaching a flipper on how to launch her first successful campaign. Here’s how to make direct mail work for you.

Full Episode >

7FF 788: These Two Teenagers Flipped A House In 2 Weeks On TV

May 21, 2025

Sister fix and flip rehab stars, share the behind the scenes about their new TV show, Kids Who Flip. With tight deadlines to meet, contractor issues and still balancing their lives to have fun in the mix, they share ALL the highs and lows of being a kid in real estate.

Full Episode >

7FF 787: How This Power Couple Went from 0 to 8 Flips in Just 12 Months

May 15, 2025

I got to sit down with two Runway members that absolutely blew me away! Ted and Stephanie show us exactly how they managed to turn a run-down trailer into a 6 figure profit.

Full Episode >

7FF 786: Why Homes Are Sitting On The Market Longer (And What To Do About It)

May 13, 2025

Dr. Sheri Fluellen and I uncover some surprising data points that might just change your mind on the market. Listen in to learn more about buyer and seller markets, how to find them, and how they affect you.

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.