Mike Michalowicz's Blog

November 18, 2025

The Real Cost of Growth – and Why Don Miller Keeps Teaching Me This Lesson

There are people you meet in your career who quietly (or not so quietly) recalibrate your understanding of leadership. For me, Donald Miller is one of them. 

Don’t let the best-selling-author/speaker/entrepreneur résumé fool you – his greatest talent isn’t just storytelling. It’s self-awareness. It’s humility. And it’s the ability to grow without losing the thread of who he is.

That’s why I love going to author retreats with him (or anywhere for that matter).  I’ve learned so much from watching how he leads, and why I’m thrilled to bring his story to episode three of Becoming Self Made.

Don didn’t start out wanting to build a powerhouse company like StoryBrand. He wanted to write one good book. Maybe two. That’s it. But life had other plans, and not always pretty ones. His first book underperformed. He made a bad investment and lost his entire life savings. He hit walls that would’ve taken most people out.

But here’s what Don did differently:
He let failure crush his ego, not his ambition.

Instead of spiraling into “I’m not cut out for this,” he asked better questions:
What did this failure teach me about my assumptions? My skills? My blind spots?

Don treated failure like data; useful, unemotional, and incredibly clarifying. Every misstep gave him direction. Every setback helped him refine the kind of creator, entrepreneur, and leader he wanted to become.

As Don grew, he learned that growth always has a price.
Time. Energy. Relationships. Beliefs you swore were “the way.”

Week 3 of our pilot series of Becoming Self Made is all about scaling, and Don nails the message:
You’re never “done.”

Real growth requires:

trusting your team more than your own control-freak tendencies,hiring people who are self-directed because you know you aren’t a micromanager,staying curious about your limitations instead of pretending they’re strengths,and adapting your business model when the world shifts around you.

When AI started changing the marketing landscape, Don didn’t stiff-arm it. He changed StoryBrand’s entire service model to leverage it. That’s leadership over comfort. That’s growth over fear.

And it leads to the most important question Don poses in this episode:
Who’s helping you grow… and who’s holding you back?

Because scaling isn’t about bigger.
It’s about becoming braver. Clearer.
More honest about the way you work, and the way you don’t.

This episode is a masterclass in humility and evolution from someone who’s still in the arena, doing the work, and asking the right questions.

If you’re a founder, entrepreneur, or builder of any kind, do not miss this story. 

Let this one challenge you. In the best way possible. Catch Donald Miller’s full conversation with me on Episode 3 of our six-part pilot season of Becoming Self Made, a Relay podcast hosted by me, Mike Michalowicz.
DOWNLOAD HERE and listen in!

New episodes drop every Tuesday for six amazing weeks!

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Published on November 18, 2025 04:00

November 13, 2025

Becoming Self Made: What You Don’t Know About The Savannah Bananas 

I’ve been friends with Jesse and Emily Cole since before they became public figures, and I’ve witnessed their impact firsthand. They gave me the opportunity to sit down with them, talk about our history, and share story after story that no one knows. This video shares (almost) all of it.

Once you watch, I have one more story for you… a story that perfectly defines the heart of who Jesse and Emily are. To my knowledge, it has never been told.

On June 10, 2017, my wife Krista and I took a trip to Savannah to see the team play and grab dinner with Jesse. As we finished, he quietly asked the waiter to pay the bill for a random table nearby. He insisted the waiter only tell them it was a gift from another table, and not to reveal their meal had been paid for until after we left.

When I asked him why he did this, Jesse simply said, “To put goodness in the world.” He then revealed he does this every time he eats out. Mind you, this was almost a decade ago, when the Bananas were struggling and Jesse and Emily had no money whatsoever. His critics were loud and success felt distant, yet he kept giving because it was the right thing to do.

Jesse and Emily Cole are the definition of people who do good things when no one notices. I can assure you, their global success isn’t focused on profit, it’s focused on the impact and joy they bring to people.

If you think the Savannah Bananas are entertaining, that’s only half the truth. Jesse and Emily are giving and good. They are exactly what the world needs. I am proud to call them friends.

Very proud.

-Mike

 

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Published on November 13, 2025 06:20

November 12, 2025

Who We Become and Who We Help: A Thanksgiving Reflection

It’s Thanksgiving week here in the States, and it always gets me thinking about gratitude – not in the “say what you’re thankful for before the turkey gets cold” kind of way, but in a deeper, quieter sense. The kind that comes from looking at what really matters and asking, “Am I living in a way that honors that?”.

When I started my first business, I was focused on survival. Making it work, getting to the next month without losing sleep over bills. I couldn’t have imagined that decades later, my work would allow me to create freedom, security, and joy.  Not just for me, but for my family, my team, my clients, and countless entrepreneurs I’ve had the privilege of working with. You starting to feel the feels yet?

Family and the foundation of gratitude

At the heart of it all is family. My wife and kids are the reason I keep pushing, keep learning, and keep building. Their laughter, support, and patience remind me every day that business is not just about numbers on a balance sheet. It’s about quality of life.

Life is demanding for business owners. There are long days, lots of travel, and decisions that can make or break you. But my family gives me perspective. They remind me why I do what I do, and they keep me grounded. Every milestone, every success, every lesson learned…it’s better because I get to share it with them. (And of course, because they put up with me.)

Team and shared success

Over the years, Kelsey (The Prez) and I have worked to create a business that gives back: profit-sharing, flexible schedules, and opportunities for growth. When my team thrives, I thrive. And when we thrive together, the impact reaches even further to the clients we serve, the entrepreneurs we mentor, and the communities we touch.

It’s a reminder that business isn’t just about what you make, it’s about what you give. The systems I’ve built through Profit First, The Money Habit, and my books aren’t just tools to generate income; they’re tools to create freedom. Freedom for families, freedom for teams, freedom for entrepreneurs to focus on what really matters.

Gratitude for the people who make it possible

None of this, my family’s security, my team’s opportunities, or the ability to support other entrepreneurs, exists in isolation. It exists because of you. The reader, the customer, the client, the entrepreneur who chooses to trust my methods, buy a book, attend a workshop, a keynote speech, or share a moment of their journey with me.

You make the entire ecosystem possible. Your engagement allows me to create the resources, strategies, and frameworks that help thousands of people find clarity, confidence, and control over their lives and businesses. Every email you open, every book you read, every session you attend isn’t just a transaction; it’s a partnership in building something meaningful.

I want to be very clear: when I talk about gratitude, I’m talking about you. Your trust, your belief, your willingness to act on what I share make my work real. It allows me to pour into my team, my family, and the wider entrepreneurial community. Without you, none of the impact I hope to have would be possible.

A simple gratitude practice

Here’s something I encourage you to do this Thanksgiving: take a moment to look at your business and your personal life, and ask yourself:

Who has made my journey possible?
Who am I grateful for today, and have I told them?How can I use the resources I have to lift up others?

Then take action. Write a note to a client, thank your team, give your family an extra dose of your attention, or contribute to a cause that matters. These are the moments that give meaning to your money, your business, and your life.

Entrepreneurship is messy, chaotic, and exhausting. But it’s also a gift. This Thanksgiving, I’m grateful for the chance to serve, for my family, my team, my clients, and for you. You’re reason I get to do this work. Success isn’t just what you build; it’s who you become and who you help along the way. Thank you for letting me be part of your journey.

Here’s to gratitude and making a meaningful impact. 

Happy Thanksgiving.

-Mike

 

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Published on November 12, 2025 08:27

November 11, 2025

The Money Habit – Manuscript Reader Feedback About Inflation

When I was writing The Money Habit, I thought I had it all figured out. Clear systems. Simple allocations. Habits that could take anyone from chaos to control. But then I asked my readers for feedback—and boy, did they deliver.

One question came up again and again: “Mike, what about inflation?”

Ah, inflation. That sneaky, creeping monster that hits your wallet before you even notice. And they were right: I hadn’t dug into it enough. So I went back to work. I wanted to give readers something practical—something they could use today—that wouldn’t feel like a temporary hack. Something evergreen.

Here’s what I realized: inflation hits in waves, and it hits your essentials first. Food. Fuel. Groceries. The weekly stuff you literally can’t skip. Then comes utilities, transportation, shipping, even your rent or mortgage once contracts reset. Your wants and dreams? They’re next. But here’s the kicker—they’re optional. You can delay or scale them without jeopardizing survival.

So here’s the approach I added to the book: secure the essentials first. Make sure your Needs account can handle rising costs. Then shift some cash to your Emergency account. Even a six-month cushion can make inflation feel less like a punch to the gut and more like a challenge you can manage.

But don’t go overboard cutting your Wants. That’s a joy killer. You don’t need to cut your fun into a thousand little losses. Instead, make one smart swap. If a full spa day is out, try a group meditation session. One big adjustment is easier to swallow than four tiny cuts that make you feel like you’re constantly losing.

Think ahead, too. If your lease ends next year, don’t wait for the rent increase to hit. Look up local trends, estimate the increase, and start setting aside the difference now. Let’s say your rent is $3,000 a month and expected to jump 15% to $3,450. Start saving that $450 monthly in your N-Rent account. By the time your lease renews, you’re prepared—no panic, no scrambling.

Same thing for adjustable-rate mortgages. Inflation can drive payments up fast. Lock in a fixed rate if you can. If rates drop later, refinance. But if they rise? You’re already ahead. Stabilize the essentials first, and the rest of your budget can breathe.

This chapter changed because I listened. My readers reminded me that money isn’t just numbers on paper—it’s stress, anxiety, and the real-life feel of inflation creeping into your life. By giving practical, proactive steps, The Money Habit isn’t just about control. It’s about confidence.

So here’s my takeaway for you: don’t wait for the next wave of inflation to hit. Secure your essentials. Build a cushion. Adjust your Wants smartly. And remember: this isn’t about perfect cuts or extreme sacrifices. It’s about taking control, staying calm, and building habits that last—no matter what the economy throws your way.

That’s what I call a Money Habit. That’s how I hope this book serves you. And if there’s one thing I’ve learned in all these years, it’s this: if you listen, people will tell you exactly what they need. And if you actually act on it, you can change lives.

-Mike

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Published on November 11, 2025 09:58

Built on Belief: Jesse and Emily Cole on the Savannah Bananas’ Rise from Rejection to Entertainment Revolution – Becoming Self Made Episode 2

Savannah Bananas has been taking the country’s baseball audience by storm. It’s  no wonder they’ve become so successful. When you meet Jesse and Emily Cole, co-founders of the Savannah Bananas, you quickly realize you’re not talking to your average baseball entrepreneurs. You’re talking to two people who decided to flip the entire playbook on its head.

And then light it on fire for good measure.

In the second episode of Becoming Self Made, I sat down with Jesse and Emily to talk about how they transformed a failing minor league baseball team into a global entertainment phenomenon. What struck me most wasn’t just the scale of what they built, it was how they built it: 

Not on profit, but on people. On belief. On joy.

And on the unshakable idea that rejection isn’t a stop sign. It’s a spark.

Fans First. Always.

From day one, Jesse and Emily didn’t build around baseball; they built around fans. When everyone else was asking, “How can we make more money?” they asked, “How can we make more joy?”

They refused to raise ticket prices, even when consultants told them they were leaving money on the table. They opened up access instead of gating it. Every rule, every decision; from how players danced on the field to how the fans interacted with the game; came down to one question: Will this make people happy?

The result? A fanbase so passionate that the Savannah Bananas now sell out every game, everywhere they play, with waiting lists that would make Major League teams jealous.

The lesson for me and for every business owner I know,  is this:
Make customer delight your growth engine.
Design experiences that make people feel seen, valued, and part of something. When you do that, profit follows naturally. Passion always precedes the paycheck.

Rejection as R&D

You can’t revolutionize a sport without making a few enemies.

The Coles were booed in their own hometown. Baseball purists mocked Banana Ball as a gimmick. Consultants told them to “tone it down.”

They didn’t listen.

Instead, they treated every criticism as data. Every “no” became fuel for iteration. They tested, tweaked, and experimented in public. They didn’t wait for permission. They turned the stands into laboratories for joy, trying new rules, new formats, new ways to connect with fans.

And slowly, the results started speaking louder than the rejection ever could.

Jesse told me they even save the harshest comments as reminders that innovation often looks like insanity until it works.

The takeaway:
Treat rejection as research. It’s not a reflection of your worth; it’s feedback on your experiment. Prototype fast. Iterate publicly. You’ll be misunderstood before you’re celebrated,  and that’s okay.

Profit First… Even when there’s none

At one point, Jesse and Emily were over a million dollars in debt. They sold their house. They shared one phone charger. They lived on $30 a week for groceries.

And yet, they believed.

During that brutal stretch, they read Profit First and started applying the system to their business finances. They didn’t wait until things “got better.” They did it right in the middle of the storm.

It represented something much bigger than accounts: discipline. Control. A sense of possibility when everything else felt impossible.

That structure, combined with their relentless optimism, got them through the leanest years.

And when the Bananas finally broke through,  those habits were what allowed the growth to stick.

It’s one of the most powerful examples I’ve ever seen of how structure doesn’t limit creativity,  it protects it.

Their story reinforced a truth I’ve seen over and over again:
You can’t out-earn bad habits.
You can’t build freedom without discipline.

Building with recovery in mind

Here’s something I love about Jesse and Emily’s approach: they intentionally schedule recovery into their business. Every midseason, the team takes a 20-day break. No games, no chaos, no guilt.

Because they know burnout isn’t a badge of honor. It’s a business risk.

That commitment to rest allows their creativity to reset. And that’s what keeps the energy, the ideas, and the fun alive.

For me, that’s a reminder we all need,  especially entrepreneurs:
Rest isn’t the reward for success. It’s the requirement.

Belief as a business strategy

The Savannah Bananas’ success wasn’t built on luck, funding, or even baseball. It was built on belief.

When nobody else could see the vision, Jesse and Emily could.
When they were told “no,” they heard “not yet.”
And when they were broke, they acted like millionaires of imagination.

They didn’t chase fans; they created believers.

As we wrapped our conversation, Jesse told me something that stuck:

“We’re not trying to build a billion-dollar company. We’re trying to create a billion fans.”

That one line sums it all up. Their business isn’t just an entertainment company, it’s a movement.

Final thoughts

I’ve interviewed a lot of entrepreneurs, but what makes Jesse and Emily’s story unforgettable is their commitment to leading with purpose and play. They remind us that business doesn’t have to be a grind. It can be a game, and one worth cheering for.

So if you’re in your own “Banana Ball moment”,  getting booed, doubted, or dismissed, keep going.

Rejection isn’t a red light. It’s the universe asking, “How bad do you want this?”

Believe in what you’re building, and back that belief with structure, discipline, and joy.

That’s how revolutions start.

You’ve got this!

-Mike

Download this episode now:  https://relayfi.com/becoming-self-made-podcast

I am so excited for you to listen and learn with us. Follow Becoming Self Made for the six-episode pilot season, with new episodes every Tuesday, and hear unfiltered stories of founders who’ve built, stumbled, reset, and succeeded.

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Published on November 11, 2025 08:47

THE PODCAST FOR ENTREPRENEURS: BECOMING SELF MADE

When someone asks me if they’ll benefit from one of my books, I tell them: Just read a couple of pages. Actually, any two pages, for that matter. It’s the responsibility of the book to engage the reader, not the other way around. It must serve. It must entertain. It must deliver.

I’ve decided to dive back into podcasting with that exact attitude.

I’m not asking for an hour of your life. I’m inviting you to give my new show two minutes, a quick listen (ideally, a watch), and judge for yourself if it serves, entertains, and delivers. Welcome to my new podcast, Becoming Self-Made, sponsored by my buddies at Relay.

On the show, I meet with founders of companies you’ve surely heard of, like the geniuses behind The Savannah Bananas, 1-800-GOT-JUNK, and CoFertility, just to name a few. But instead of hearing the same old “I did this to get rich, and that to scale big, and blah blah blah, follow my path” junk, I ask them the questions they never get asked:

Where did they really struggle?When did they want to quit?What are they most challenged by right now?What regrets do they carry?Has it been worth it? I mean, really worth the cost?

Here’s the stunning truth I’ve discovered… these founders, no matter their company’s growth, still face the same challenges that you and I do:

Insecurity: They struggle with the internal whisper questioning “worthiness.” They feel the discomfort when stepping into the public eye or pushing themselves out there.Leadership Pressure: They grapple with the fear of pushing too hard, or conversely, not pushing hard enough to sustain growth. They’re still trying to figure out how to grow as a leader at the speed their business demands.Personal Cost: They talk about immense personal and family sacrifice. They don’t know when they will have “arrived”, if ever. They live in a process that is exhausting.

What’s the obvious observation?

Messy is normal. Struggle is the required tuition.

Whether you have three zeros in your revenue number or nine, the core challenges remain the same. The only difference is that these founders are a few chapters ahead in the same book. Becoming self-made is a journey of messy growth. Lean into the growth. Embrace the messy.

You’ve got this!

-Mike

Download this episode now and listen in. https://relayfi.com/becoming-self-made-podcast

I am so excited for you to learn with us. Follow Becoming Self Made for the six-episode pilot season, with new episodes every Tuesday, and hear unfiltered stories of founders who’ve built, stumbled, reset, and succeeded.

You’ve got this!

-Mike

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Published on November 11, 2025 07:55

November 6, 2025

Lessons from the Lows & Excerpts from My Personal Journal

I used to think success meant a fancy office, a fat revenue line, a sweet house, and an even sweeter car.

I had all that. And then I found out I was broke.

No joke. I had built and sold companies, appeared on stages, had the business cards that made me look legit… and one day…

I’m doing something I’ve never done before. I’m sharing a few excerpts from my journal from years ago. I want to show this to you so you know that our financial journeys, business or personal, are something we can be in control of.

Day 1 (The wake-up call)

I am shaking. I have no other place to put this, so I’m putting it in this journal. It’s Valentine’s Day. Every year, we have a special dinner to celebrate together as a family. We all look forward to it. Only today, my accountant called and told me that while profitable on paper, I am out of cash.

I’m going to throw up now. Then I’m going to hide.

Day 2-25 (Stuck)

I have a hard time getting out of bed. I feel so weighed down and embarrassed. Booze helps, but I can’t start that in the morning. My family needs me. I don’t know how to show up. I can’t tell anyone else.

Day 26 (Realizations)

When my accountant called me at work and laid the bad news on me, I laughed. That uncomfortable kind of laugh where you’re hoping someone is wrong. 

He wasn’t.

I went home, put on my best acting face, and sat at the head of the dinner table. I couldn’t hold it in, and I heard the words spill out of my mouth as I told my wife Krista and the kids that we were in serious trouble. The look on their faces said everything. Fear. Questions. Anxiety. Disappointment 

Then, Adayla (my daughter) left the table and came back with her piggy bank, offering to take care of us all. 

That night, I stared at my reflection in the window and said out loud, “You’re a freaking idiot.”

I need to stop pretending that I have it all figured out. Maybe this is the reality. Maybe these things happen to a lot of people.

Day 27 (Get off your a$$)
I haven’t wanted to get out of bed lately. I’m a little hungover.

But if not for me, I need to get up and start working on a way out of this mess for my family. 

I’m going to go for a run. Maybe that will get the blood flowing and help pull me out of this. 

Day 28 (Nope)

I’m sore. When I was running yesterday, I said I’d start this habit of running six days a week. I drank again last night, and I’ll just go tomorrow. 

Day 29

Maybe I’ve been judgmental of others, but I really get it now, why people feel sorry for themselves. I don’t feel like anyone around me really gets what I’m going through. This sense of failure. This dread. I’m going to try a run. A short one. Because I drank again. 

Day 29

Short entry – I left my sneakers on the toilet last night. This way, when I got up this morning, I’d have to move them to go to the bathroom. I have my sneakers on now and am going for a longer run. 

Day 35

The sneakers on the toilet trick is working. And now, when I’m out there running, I realize I can do this with other things. Like my business. I love creating; my mind is always going onto the next great idea. I think my next great idea is setting up a habit in my business, like I do for my running.

I’ve been grappling with a realization. I’ve spent years building this “entrepreneur” identity,  and now it feels like a lie. 

But is it? Isn’t part of entrepreneurship failing? When we work at corporations, everything is already set up for us, and we have little control over any kind of innovation. 

But that’s one problem I don’t have. I can innovate, create, and change anything I damn well want. 

Holy crap.

Day 35 (Later in the evening)

This morning, after my run, I grabbed a notebook and started writing a business plan, but this came out instead:

You built an empire with no foundation.
You confuse revenue with success.
You’re broke.

Every sentence punched me in the gut. But I needed it.

That’s when it clicked: money isn’t my problem. My behavior is my problem. At home and in my business, I spend first, save last, and convince myself “next month will fix it.” It never did.

So I asked myself one question that changed everything:

What if I change my business account allocations and take profit before paying everything else? That way, I would have the money I need, no matter what came up.

(That was the seed. I didn’t know it yet, but that notebook would become Profit First.)

End of journal entries.

Next steps

Now that I’ve really bared it all, here’s the plan that made no sense (at first)

The morning I started thinking about reallocating the business cash flow, I drove to the bank like a man on a mission. I had to be quick before I lost my nerve.

The banker asked, “Why do you need five checking accounts?”

I said, “Because I clearly can’t be trusted with one.”

He blinked. Then he opened them anyway.

I labeled them: Income. Profit. Taxes. Owner’s Pay. Operating Expenses.

The system was simple: every time money came in, I split it up right away. No mental math. No “I’ll save later.” Later never comes.

That first profit transfer? One percent. Literally a few bucks. But it was mine.

It wasn’t the amount,  it was the motion. For the first time, I paid myself before paying anyone else.

And it felt damn good.

The rhythm
A week in, something weird happened. I felt a little peace.

For the first time in my life, I knew where the money was going. I wasn’t waking up in panic mode, refreshing my bank balance, pretending everything was fine.

The system started working. I started breathing again.

That same rhythm, consistent, structured, reliable, is what would later become Profit First, and now The Money Habit. I didn’t need to be the hero anymore. I just needed a plan that didn’t rely on me having a “good day.”

The lesson I wished I’d learned sooner
Looking back now, I can tell you the lowest point wasn’t when I lost the money.

It was when I lost control. When my self-worth was tied to my business’s revenue, not its reality.

Here’s what I know for sure:

You can’t out-earn bad habits.You can’t out-hustle disorganization.And you can’t build wealth if you’re too afraid to look at your numbers.

When I stopped running from my finances, both business and personal, everything changed.

That 1% transfer grew. The systems grew. And eventually, so did the freedom.

Now, every quarter when I take a profit distribution, I pause for a second and think back to that night at the kitchen table.

The guy who thought he’d lost it all had actually found the foundation for everything he teaches today.

If you’re in your own “Day 1,” here’s my advice:
Don’t panic. Don’t fake it. Don’t wait.

Take your profit or savings first.
Build your systems now.
And please remember that your low isn’t your ending. It’s your starting line.

It’s a bouncy ride. But I know you’ve got this. (Heck if I can come back, anyone can.)

-Mike

PS – Some exciting things are happening!

The Money Habit is available for preorder here. Get peace of mind about money.

My new podcast, Becoming Self-Made, is the free business advice you cannot do without here. I am so excited to have teamed up with Relay on this project, and we’re talking with heavy hitters like Jesse Cole from Savannah Bananas, Don Miller of Storybrand, and many more! Don’t miss out.

Watch the trailer now and get a sneak peek: Watch the TrailerOr visit the podcast homepage for all updates: Becoming Self-Made Podcast

And as always, free resources to support you are here on my website. From the Profit First Assessment to just about anything else you need!

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Published on November 06, 2025 08:35

November 4, 2025

Episode 1 – Becoming Self Made Podcast with Relay – Starting Out and Restarting – The Power of the Reset, Rebuild & Repeat Lessons from Brian Scudamore and 1-800-GOT-JUNK?

The boldest business move isn’t adding more, it’s ripping it all apart and starting fresh.

That’s exactly what my friend Brian Scudamore, founder of 1-800-GOT-JUNK?, did. And it’s also why he built one of the most legendary service brands in North America.

For our first ever episode of Becoming Self Made, presented by Relay, I visited Brian to get the scoop behind entrepreneurship: from a $700 startup and a beat-up pickup truck to a $700 million empire, and everything in between. If you’ve ever wondered what it really takes to grow, scale, and build a team that’s actually aligned with your vision, this episode is your blueprint.

Resetting for growth

Brian’s story is a masterclass in the power of hitting reset. He started his company at 19 years old with almost nothing. As the business grew, he faced the harsh reality that success without alignment leads to chaos. Even at $100 million in revenue, Brian realized his team wasn’t living the company’s core values. His solution? He made the gut-wrenching decision to fire his entire team and rebuild with culture and values at the center (something that resonated with me based on how we’ve run my company, too!).

The vital lesson: you can’t scale chaos. Alignment is everything. Growth without clarity is wasted effort.

The Painted Picture: Vision meets execution

Brian’s business strategy is phenomenal. He calls it the Painted Picture, an exercise that helps you get some perspective from a more objective view. Brian starts by envisioning his business three years into the future as if it already existed. He created a roadmap that aligned his team, set expectations, and gave everyone clarity on their role in the bigger mission to reach the goals.

For entrepreneurs, this is a tactical tool that ensures your team moves together, focused on long-term goals instead of scrambling for short-term wins.

Lessons for entrepreneurs

Brian’s journey offers hard-hitting lessons for anyone running or scaling a business:

Clarity is power – Know what your business stands for and who belongs on your team.Courage fuels growth – Growth sometimes requires tough, uncomfortable choices.Culture is non-negotiable – Values-driven hiring and team building create sustainable success.Vision drives execution – A clear, communicated vision transforms chaos into coordinated action.

Real growth starts with clarity, courage, and the willingness to hit reset when things aren’t right. You can’t fake culture, and you can’t outsource alignment. You have to build it intentionally.

Why Becoming Self Made Matters

“Becoming Self Made” isn’t a podcast for dreamers, it’s for doers, and we’re giving you the nitty gritty stories behind entrepreneurship, scaling, and personal transformation. Brian’s story hits hard because it’s authentic: the wins, the failures, the pivots, and the breakthroughs that define real business success.

This podcast delivers actionable insights, relatable stories, and wisdom that can save you time, money, and headaches. Whether you’re starting out, scaling, or pivoting, there’s a lesson here for you.

Apply Brian’s Lessons Today

Identify bottlenecks – Spot the systems, habits, or behaviors slowing your business.Rebuild your team and processes – Don’t fear tough decisions; sometimes resetting is strategic.Communicate your vision – Use tools like the Painted Picture to align your team.Prioritize values over convenience – Hire for alignment, not just skills.

Brian’s journey is proof: starting over isn’t failure, it’s a strategic play for long-term success.

Download this episode now and listen to Brian’s full journey. https://relayfi.com/becoming-self-made-podcast

I am so excited for you to listen and learn with us. Follow Becoming Self Made for the six-episode pilot season, with new episodes every Tuesday, and hear unfiltered stories of founders who’ve built, stumbled, reset, and succeeded.

You’ve got this!

-Mike

The post Episode 1 – Becoming Self Made Podcast with Relay – Starting Out and Restarting – The Power of the Reset, Rebuild & Repeat Lessons from Brian Scudamore and 1-800-GOT-JUNK? appeared first on Mike Michalowicz.

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Published on November 04, 2025 11:11

November 3, 2025

Your Money Habits Are Controlling Your Life (Even If You Don’t Realize It)

If I dropped a million dollars into your bank account tomorrow, how long do you think it would last? A year? Two? Maybe five?

The answer is shorter than you think. And it’s not because you’re terrible with money, it’s because your habits quietly run your financial life.

I know, because I’ve seen it over and over, in businesses, in families, and in my own life. Your habits are the bottleneck that determines whether your money works for you or against you.

Money is more than math – it’s psychology

We treat finances like a spreadsheet problem. We think, if I earn more, save more, invest more, I’ll be okay. 

Money is deeply emotional.

It’s tied to our identity, our fears, our childhood lessons, and the stories we tell ourselves about worth, success, and security.

These ideas play into what I call toxic money habits; patterns that make you act against your own best interests, often unconsciously. They might look like:

Spending impulsively to soothe anxiety or boredom.Avoiding financial planning because it feels overwhelming or shameful.Hoarding money out of fear, missing opportunities to grow or invest.Chasing status symbols to feel worthy, even if it creates debt or stress.

Not only are these bad money habits, they’re habits your brain has automated to protect you from fear, even when that fear is outdated or irrational.

If these patterns aren’t identified and corrected, more money doesn’t help.

More money only accelerates the problem. You could win the lottery, get a raise, or sell a business for millions, and still burn through it because your psychology about money hasn’t changed.

The bottleneck in your life

In The Money Habit, I talk about bottlenecks in your life. A bottleneck is the point where everything slows down, where growth gets stuck. For most people, that bottleneck is their relationship with money.

Your money habits dictate everything:

How you save, or fail to saveHow you invest, or avoid investingHow you manage stress around unexpected expensesHow you make financial decisions that ripple through your life and work

If you don’t notice these habits, you’re running on autopilot, and autopilot rarely leads to financial freedom.

One habit can change your personal finances

You don’t need to fix everything at once. In fact, trying to overhaul every financial behavior at once is a recipe for burnout and failure.

Instead, pick one habit that’s clearly limiting you. That’s your bottleneck. Focus on it. Master it.

Maybe it’s checking your bank account obsessively without taking action. Maybe it’s impulse spending. Maybe it’s failing to automate savings. Whatever it is, it’s the single habit that, if improved, will have the biggest impact on your financial health.

When you fix that one habit, something magical happens: it creates momentum. You build confidence. You start noticing other behaviors that need tweaking. Slowly, your financial life begins to align with your goals.

Your personal money habits shape your reality

I often ask people: Do your habits help you reach your dreams, or do they hold you back?

The answer isn’t always obvious. Habits feel comfortable, even when they’re toxic. Overspending feels like relief. Avoiding your finances feels safer than facing the truth. Chasing status feels empowering.

But comfort doesn’t equal progress. Over time, these habits erode your savings, create stress, and limit your freedom, sometimes without you realizing it.

Changing one habit creates a ripple effect. It changes how you think about money, how you act, and how your financial system supports your life. It’s not about willpower. It’s about awareness, reflection, and intentional practice.

A personal example

When I first started my business, I thought earning more would solve everything. I made money, but I didn’t save. I didn’t have systems in place. And every unexpected expense felt like a crisis.

I realized my habits were sabotaging me. I was living in reaction mode: spending first, saving later (or never), and letting stress dictate my choices. The bottleneck wasn’t my income; it was my habits.

Once I focused on one habit like automating savings, I started seeing change. I could finally step back, see my financial picture clearly, and make deliberate decisions. 

Ends up it’s not just about the money; it was about confidence, clarity, and freedom.

The psychology behind saving

Your brain wants comfort and instant gratification. That’s why you spend impulsively, procrastinate on budgets, or hide from your finances.

But when you design your habits to align with your goals, you create a system where your brain works for you, not against you.

Some strategies I like include:

Automating your savings so you never have to make the decision in the moment.
Tracking your triggers to see what causes bad financial decisions.
Visual reminders of long-term goals to make delayed gratification more appealing.
Micro-reflections on spending choices to build awareness over time.

The goal isn’t to feel guilty about every dollar; it’s to build habits that naturally produce good outcomes.

The takeaway

More money doesn’t fix toxic habits. Awareness, reflection, and small, intentional changes do.

If you want to grow your savings, reduce stress, and take control of your financial life, start by identifying the bottleneck: the toxic habit that’s slowing you down. Master that one habit, and the rest will follow.

Because wealth isn’t created by luck. It’s created by how you behave with the money you already have.

So today, ask yourself: Which money habit is holding me back, and what’s one small change I can make right now?

The answer could change everything.

Here’s to your peace of mind. 

-Mike

PS – Some exciting things are happening!

The Money Habit is available for preorder here. Get peace of mind about money.

My new podcast, Becoming Self-Made, is the free business advice you cannot do without here. I am so excited to have teamed up with Relay on this project, and we’re talking with heavy hitters like Jesse Cole from Savannah Bananas, Don Miller of Storybrand, and many more! Don’t miss out.

Watch the trailer now and get a sneak peek: Watch the TrailerOr visit the podcast homepage for all updates: Becoming Self-Made Podcast

Clockwork can help you automate your business and get you that time freedom you need to rest, restore, and innovate. Grab your book here. 

And as always, free resources to support you are here on my website. From the Profit First Assessment to just about anything else you need!

 

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Published on November 03, 2025 14:03

October 29, 2025

Want to Save Money? Easy. Change This One Thing.

Budgeting, overspending, impulsive buys, we know the cycle. Money management is challenging. But one lesson keeps coming back: mastering even a single spending habit can create a ripple effect across your entire financial life.

I used to think financial discipline was all about willpower. I’d wake up Monday determined to track every penny, skip my morning coffee to save, or set strict rules for myself. And for a while, it worked. Then something small would derail me.  Maybe a dinner out I didn’t plan for, an online splurge, a gift I couldn’t resist…and all the discipline would vanish.

That’s when I realized something crucial: you don’t need to overhaul your entire financial life at once. You just need to pick one habit and give it your full attention. The habit I focused on first wasn’t glamorous, but it was successful!

I made it harder to spend money.

While writing The Money Habit, I wanted to be sure to include real-life examples of changes people make to try to save money. One of them centers around adjusting your technology to make it harder to shop. (Ugh. I know. It’s so convenient. And who doesn’t love automatic gratification?)

An excerpt from The Money Habit – real-life example:

Nicole Chiarolla participated in the Money Habit training at A1 Garage Door Service and found a way to work with her online shopping habit, rather than eliminate it. She said she put items in her online shopping cart just like she always did. But rather than check out that day, she waited at least two weeks. Anything she still wanted at that time she would allow herself to purchase. Online “window shopping” gave her the same serotonin rush she got from checking out, and she didn’t buy as much as a result. This helped Nicole save enough to pay an additional $700 a month on her mortgage.

You can use technology to your advantage, to work with your habits. Here are a few:

Turn off notifications (see ya, retailers).Add friction – make it harder to shop. Unsave your credit card numbers from apps. Better yet, get rid of the apps. You heard me.Don’t store passwords in your browser. I know. Unheard of.Swap your cart for a wish list.Delay shipping – it makes you reconsider your purchase. 

These are just a few ideas from the book. There’s a ton left out here. But I have tried each of these shifts in my habits, and the result was incredible. Each time I felt the urge to spend, I had to pause, think, and navigate the friction I’d built into my process. That pause gave me the power to ask myself, Do I really need this? Is this helping me reach my bigger goals? And over time, I noticed something amazing: mastering this one habit made it easier to control other areas of my spending. I started noticing patterns, anticipating impulsive urges, and creating small, intentional rules in other areas of my finances.

This approach is exactly what The Money Habit emphasizes: financial habits aren’t just about numbers, they’re about behavior. Money is personal, and the habits we form with it reflect our values, emotions, and thought patterns. By choosing one habit to focus on, you can start reshaping your relationship with money from the inside out.

I’ve seen this happen in my own life. Once I mastered the habit of creating friction, I started noticing other small but important habits: paying bills immediately to avoid late fees, planning purchases instead of impulsively buying, and even automating savings. What started as one simple habit, one small decision to pause before spending, ended up influencing nearly every financial choice I made.

The beauty of this approach is that it doesn’t require perfection. You don’t need to overhaul your life, and you don’t need to track every single expense to the penny. You just need a single, actionable habit that matters to you. That’s what creates lasting change.

Financial mastery isn’t about restriction or deprivation, right? Right. It’s about clarity, control, and choice. By committing to one habit, like creating friction in spending, you give yourself the tools to gain control in other areas of life, too. It’s the domino effect: one habit leads to another, and suddenly, you’re not just surviving financially, you’re thriving.

So, if there’s one takeaway I hope you’ll embrace this week, it’s this: pick one spending habit to master. Make it concrete, make it actionable, and give it your full attention. Track it, tweak it, and let it become second nature. Then watch as the momentum carries over into other parts of your financial life.

Your relationship with money, like any relationship, is nurtured one step at a time. Master that first habit, and the rest will follow.

You’ve got this!

-Mike

PS – Some exciting things are happening!

The Money Habit is available for preorder here. Get peace of mind about money.

My new podcast, Becoming Self-Made, is the free business advice you cannot do without here. I am so excited to have teamed up with Relay on this project, and we’re talking with heavy hitters like Jesse Cole from Savannah Bananas, Don Miller of Storybrand, and many more! Don’t miss out.

Watch the trailer now and get a sneak peek: Watch the TrailerOr visit the podcast homepage for all updates: Becoming Self-Made Podcast

And as always, free resources to support you are here on my website. From the Profit First Assessment to just about anything else you need!

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Published on October 29, 2025 09:26