My 20-Year Journey to Financial Freedom

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Welcome to The Movement Memo, a bi-weekly newsletter where I share actionable tips to help you live your best day ever, every day.

Today's Programming 

• Movement: 20-minute AMRAP

• Quote: Ramsey on how to live

• Lesson Learned: My 20-year journey to financial freedom

• Optimization: Why I never grill alone

Today's Movement 

Complete as many rounds as possible in 20 minutes of: AMRAP

• 100 double-unders 

• 10 burpee pull-ups

• 15 GHD sit-ups
  
  

Today's Quote

In my twenties, I spent a disproportionate amount of my income on Tiffany cuff links, designer suits, and flashy cars. 

I still saved and invested, but...

If I could go back I would spend less and save more.

The spending habits you build in your 20s will dictate the way you live in your 30s and how much freedom you have in your 40s.

Today's Lesson Learned:

My 20-Year Journey to Financial Freedom: Lessons From the Climb

If you’ve ever looked at successful people and thought, “I want to do what they’re doing,” let me share something I’ve learned over the past 20 years: The secret isn’t in what they’re doing now—it’s in what they did on the way up.

The work I do today—investing in businesses, creating content, and consulting—didn’t happen overnight.

It’s the result of years of hard work, taking calculated risks, and many mistakes that led to lessons learned. Every step I took, starting right out of college, laid the foundation for what I do today.

And here’s the harsh truth: You can’t skip steps.

Most people try to leap straight to what successful people are doing now, but financial success isn’t about shortcuts. It’s about creating foundational habits when no one is watching, building your blueprint to freedom brick by brick.

This was my path to creating financial freedom, step by step, and the lessons I learned along the way.

Step 1: Building a Foundation With Recurring Revenue

In 2002, fresh out of college, I had no idea what I wanted to do with my life.

My dad gave me a piece of advice I didn’t fully appreciate at the time: “Build something with recurring revenue—it’ll pay you long after the work is done.” He set me up with a company car, and a small salary, and I got my license to sell property and casualty insurance 3 weeks to the day after I graduated from Geneso.

The first year?

It was brutal. I drove 50,000 miles, knocking on doors, hearing “no” after “no.” I remember sitting in that car after another rejection, questioning if I was cut out for this.

Eventually, I found my niche—campgrounds and marinas. These were under-served markets where I could save prospects real money. Once I landed my first few clients, things started to click. Word spread, referrals came in, and I went from struggling to building a book of business that generated income year after year.

The Lesson: Recurring revenue is the foundation of financial freedom. It’s not about trading time for money—it’s about creating something that pays you repeatedly for the effort you put in today. And the gold standard for building a business that grows exponentially is three referrals from every customer. 

Step 2: Saving Early and Investing Consistently

By 2004, I had built enough momentum with my insurance business to start thinking long-term. 

My dad encouraged me to open a SEP IRA, and I maxed it out every year. Those early contributions started compounding, and today, they’re a big part of my financial foundation.

I wouldn’t be able to take risks in business today without building a strong foundation. This is the biggest piece of advice I would give anyone trying to get ahead: it’s not sexy, or a get-rich-quick-scheme, but your future self will thank you.

In 2010, I took another step: I invested $25,000 in Tesla when it IPO’d at around $20 per share. At the time, it felt like a massive risk, but I believed in the company’s vision, and I had a stable income from my insurance business to pay my bills. Over the years, the stock price soared. 

Unfortunately, I sold many shares along the way to lock in profits. Had I held them all, they’d be worth $6.5 million today. But this was a small price to pay for the lesson I learned.

The Lesson: Start saving and investing as early as possible. Let compounding do the work for you, and when you invest, think long-term. 

Step 3: Pivoting to New Opportunities

By 2009, my insurance business was running smoothly, which gave me the freedom to invest my energy, capital, and time in something new. 

That’s when I partnered with a friend to co-found a mobile app development company. Initially, we didn’t have the budget to hire professional developers, so we partnered with 5 local college students looking for experience. For two years, it felt like we were just spinning our wheels. We poured in time, money, and effort, but results were slow to come. 

Then, things started to click—we landed clients, built momentum, and turned the business into something profitable. 

Selling my shares in 2014 wasn’t a massive financial win, but the experience taught me something invaluable: the power of persistence and the importance of strategic pivots.

The Lesson: Use the success of one venture to fund and support the next. Be patient—building something meaningful takes time.

Step 4: Turning Passions Into Businesses

In 2010, I discovered triathlons, and it changed everything. 

My love for wellness and fitness became a central part of my life. By 2013, I opened my first gym—a CrossFit and cycling studio that became a hub for community and growth. Through the gym, I met my business partner for another venture: fast-casual restaurants Original Grain and Exo Taco. 

These projects weren’t just businesses—they were extensions of what I cared about. And we sold to a starving crowd. (We placed one location right down the street from the local bars, where all the college students liked to hang out).  

The Lesson: When your work aligns with your passions, it feels less like work and more like purpose. That passion keeps you going when things get tough. And trust me – in business, there will be hard times. 

Step 5: Building a Personal Brand

In 2017, I started sharing my story online—daily posts about wellness, business, and life. 

At first, it felt like I was shouting into the void, but over time, people started to take notice. Consistency built trust, and that trust led to consulting opportunities, partnerships, and investments. Sharing my journey didn’t just help others—it created a platform that works for me even when I’m not actively working. (Remember that concept of recurring revenue from earlier?)

The Lesson: Your personal brand is your reputation at scale, and it can open doors you didn’t even know existed. Start sharing authentically—where you are, what you’ve learned, and what you’re still figuring out. The person you are most qualified to serve is yourself two years ago. 

I believe having a personal brand is still tremendously undervalued by the market, and if you are in your 20s investing in this asset will have the highest ROI out of just about anything you can do – over the long term. But I wouldn’t quit my day job. This must be a long-term play.  

Content is one of the 4 C’s of leverage (along with code, capital, and collaboration) that Naval Ravikant writes about often. And consistently creating content can put everything else you do for work on steroids and increase your surface area for opportunity.

My life and work would not be what it is today if I never overcame my fear of publishing. 

Step 6: Focusing on Equity and Relationships

Today, most of my work revolves around co-founding, investing in, and consulting for businesses specifically in the health and wellness space. This is the area where I have the most specific knowledge, can provide the most value, and spot “lucky” opportunities that others miss. (AKA find arbitrage). 

I don’t just work for a paycheck—I negotiate for equity and long-term partnerships, so my compensation is tied to the long-term success of the companies I work with. This approach wouldn’t be possible without the relationships I’ve built over the years. Partnering with the right people—those who share your values and vision—is key to scaling your impact and building wealth.

The Lesson: Focus on opportunities where you can create long-term value, and surround yourself with people who make you better.

Looking Back: The Climb That Built My Lifestyle

Every step of this journey—from driving 50,000 miles selling insurance to investing in Tesla to building a personal brand—was part of the climb. It wasn’t linear. And there were many setbacks along the way.

But the financial habits I built in my twenties, prioritized a long term view towards wealth generation in low-risk investments. This created the freedom to take larger risks later in life. 

Nothing happened overnight, and nothing was handed to me. If you’re just starting out, don’t try to skip ahead. Focus on building your foundation, saving and investing, and aligning your work with your values. 

The climb is where you learn, grow, and set yourself up for lasting success.

Start where you are with what you have. Read books. Ask mentors specific questions. Become financially literate (no one else can do it for you).

I waited too long to begin my financial education. But it is an infinite game – I still learn every single day. 

Take the first step. Your future self will thank you.

Today's Optimization

Never Grill Alone

At 27, I believed success was about solo grind.

Then, a friend gave me Never Eat Alone, and I started sharing meals with people who inspired me. Over a simple meal, everything shifted—my confidence, my goals, even my friendships. That book wasn’t just advice. It was a principle I live by today: every meal, every moment matters.

That’s why I’m all about the Schwank Grill.

This isn’t just a grill; it’s a conversation-starter, a memory-maker. With 1500 degrees of intense heat, it sears the perfect steak in seconds, bringing restaurant-quality cooking to your backyard.

And with its modern design, grill table, and rapid heat-up, it’s built to handle any gathering you throw at it.

Grilling with Schwank is about more than just food—it’s the laughter, the stories, the ideas that happen around it. Whether it’s a backyard weekend or a post-work reset, Schwank turns every meal into an experience you’ll remember.

So, fire it up. Make every meal count. 

Grill with Schwank—and bring your people around.

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Publisher: Eric Hinman

Editor-in-chief: Bobby Ryan