24 Jun 458: Start With a Win: Redefining Success, Reinventing Yourself & Building Your Next Chapter – An Interview with former CEO of RE/MAX Holdings & Best Selling Author Adam Contos
What do a Marine, SWAT leader, entrepreneur, CEO, bestselling author, investor, and podcast host all have in common?
In this episode, you’ll find out… because they’re all the same person.
This week, Mitch sits down with Adam Contos, former CEO of RE/MAX Holdings and host of the Start With A Win podcast, for a conversation about success, purpose, reinvention, and why your best chapter may still be ahead of you.
Adam’s career has taken some fascinating turns. From law enforcement to entrepreneurship to leading one of the world’s most recognized real estate brands, he’s learned that while the titles may change, the mission often stays the same: build trust, solve problems, and help people move forward.
Whether you’re early in your career, navigating a transition, or wondering what’s next after achieving significant success, Adam offers practical wisdom for creating momentum, finding purpose, and building a life you don’t need to retire from.
And perhaps most importantly…
He shares why the next big breakthrough often starts with one small win.
Before we get to the interview… Mitch wants to let you know about some very special training.
Mitch gets to talk with a lot of high achievers who are feeling that nudge… that pull… that call to do something new. Maybe make a change… or write a book… launch a business… or become a coach or a speaker.
BUT one of the biggest things that gets in the way is TIME!!!
So… we’ve put together a training called Making Time for your Next Chapter.
It’s a powerful webinar where Mitch introduces some powerful tools and strategies (and he tells some fun stories) to help you to find the time that you need… to make your next chapter… your best chapter.
You can go to MitchMatthews.com/time
NOTE: The training is $97 and it’s totally worth it!
But… since you’re a Dream Think Do-er… we want to give you a coupon code to make it free.
Just use the code MitchGuest and it will get you access for free!
It’s truly a workshop for high-achieving professionals ready to create time for what’s next without blowing up what’s already working. Go check it out!
Ready for Your Next Season?
One of the most common things Mitch hears from DREAM THINK DO listeners is:
“People keep telling me I should coach.”
Or…
“I’ve thought about speaking, consulting, or teaching what I’ve learned.”
Sound familiar?
If you’ve built years (or decades) of experience and you’ve been wondering whether there’s a bigger next chapter available to you, Mitch created something specifically to help.
The Authority Archetype Assessment is a free, research-based tool designed to help you identify your unique authority style and discover whether coaching, speaking, consulting, advising, or teaching might be part of your next season.
👉 Take the free assessment at mitchmathews.com/6
➤ In This DREAM THINK DO Episode You’ll Learn
1. A Refreshing Definition of Success
Adam shares his personal definition of success and why purpose, freedom, and growth matter far more than simply reaching a finish line.
2. The Common Thread Behind Every Career Pivot
From Marine to SWAT leader to CEO, Adam reveals the mission that connected every season of his career and how it can help you navigate your own next chapter.
3. Why Side Hustles Matter
Long before leading RE/MAX, Adam was building businesses on the side. We discuss why experimentation is one of the smartest ways to create opportunities without blowing up your current life.
4. The Power of “Micro Wins”
Adam believes life isn’t about wins and losses. It’s about wins and learns.
Discover how small daily victories can compound into extraordinary results over time.
5. What To Do When Success Starts Feeling Stale
Many high achievers aren’t failing. They’re simply no longer challenged.
Adam shares practical ways to identify complacency, create new challenges, and reignite your passion for growth.
➤ Spotlight Moments
- Adam’s powerful definition of success
- The side hustle that unexpectedly opened the door to RE/MAX
- Why solving problems became the foundation of every career move
- The shift from “wins and losses” to “wins and learns”
- A candid conversation about purpose, retirement, and staying engaged
- Why boredom might actually be pointing you toward your next season
- How micro wins create macro results
➤ Key Quotes
“I do what I want to do, when I want to do it, where I want to do it, with who I want to do it with.”
“We’re meeting people, building trust, and helping solve problems.”
“You don’t have wins and losses. You have wins and learns.”
“Little micro wins become macro wins.”
“If we’re not getting better, we’re getting worse.”
➤ More About Adam Contos
Adam Contos is a former Marine, law enforcement officer, SWAT leader, entrepreneur, bestselling author, speaker, investor, and former CEO of RE/MAX Holdings.
Today he helps leaders and organizations grow through investing, advising, speaking, and coaching while sharing practical leadership lessons through his Start With A Win podcast.
His mission is simple: help people create meaningful success by focusing on intentional growth, continuous learning, and purposeful action.
➤ Connect with Adam
-
- Website: adamcontos.com
- Podcast: Start With A Win
- Here’s Mitch’s episode on Start With a Win: CLICK HERE
- Book: Start With A Win
- LinkedIn: Adam Contos
- Instagram: @adamcontos
➤ Why This Episode Matters
A lot of DREAM THINK DO listeners are in an interesting season.
You’ve built the career.
You’ve earned the respect.
You’ve achieved goals that once felt impossible.
But maybe there’s still a quiet question bubbling beneath the surface…
“What’s next?”
Adam’s story is a powerful reminder that your next chapter doesn’t require starting over.
It requires building on everything you’ve already learned.
This conversation will help you think differently about success, growth, purpose, and the opportunities that may be closer than you think.
➤ Call To Action
Let’s make this more than just a good listen.
What’s one area of your life where you’ve become a little too comfortable?
What’s one “micro win” you could create this week?
What’s one opportunity you’ve been thinking about exploring?
Choose one small step.
Create one intentional win.
And see where it leads.
Then let us know what resonated most from this conversation.
And if someone came to mind while listening… please share this episode with them.
Because sometimes one conversation… and one small win… can change everything.
No Comments