The Math Of Persistence: What Happens When You Don't Quit
Why life's lessons only reveal their purpose in the rearview mirror
There is a great quote by Steve Jobs:
"You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future."
The thing about building something from nothing is that "nothing" gives you a different relationship with risk.
When you've already lost everything once - or started with nothing to begin with - you understand that survival is possible. That knowledge changes how you make decisions for the next 25 years.
Here's my timeline… not because my story matters more than yours, but because the pattern might help you see your own journey differently.
The Early Lessons (Ages 20-24)
20 years old: I joined my first startup as an early engineer while I still in college as a computer science major. I thought I was just getting work experience. Really, I was learning that extraordinary outcomes require ordinary people to make extraordinary commitments. Honestly, I learned how much I love to build things.
21 years old: We sold our first startup. I was convinced I'd cracked some mystical success code. The universe owed me perpetual wins because I'd figured out the game early. FYI, the universe had other plans.
22 years old: I took my new-found liquidity and became a world-traveling tennis pro to search for the meaning of life. I taught tennis to Bill Gates, Richard Branson and The Sultan of Brunei. The best part of this were all the conversations I got to have with amazing people on and off the tennis court, and of course to have the most coveted, even tan in the world.
24 years old: I moved to Maui. The island showers killed my tennis income, so I pivoted to video analysis coaching packages and figured out how to make bank without hitting a ball. This taught me that value creation doesn't require physical presence. That insight became the foundation for every remote business model I'd build over the next two decades.
The Foundation Years (Ages 26-31)
26 years old: My mentor told me that nobody was going to hire a tennis pro and recommended that I go to business school. Looking back, it was the ultimate status hack. I went to Vanderbilt for my MBA and I met my (now) wife there. When we got married, we had less than $3,000 in in our joint bank accounts. Sometimes having nothing creates the perfect conditions for building everything. She has been with me through thick and thin, and we built it all together. I owe it all to her.
28 years old: I joined Goldman Sachs during the 2008 financial crisis. I was the only student in my MBA class to make it through 39 one-on-one interviews and get hired at Goldman that year. This wasn't because I was the smartest person in the room. Let’s be clear, I knew nothing about financial markets but I was all-in on the learning. I was just hoping that they would see the human side of me. My diligence. My patience. My persistence. I am thankful that someone took a chance on me.
The Breakthrough Decade (Ages 31-42)
31 years old: I borrowed money to buy into Teles Properties with my mentor and business partner, Peter Loewy. At that time it was only one office, with 28 agents in Beverly Hills. I just believed that I could go all-in on myself and my work ethic. Peter took me under his wing and taught me the ways of the force. Learning to run a business, in an industry that I knew nothing about, while taking all the financial risk with my first child on the way, was downright scary. In fact, I had to make a PowerPoint presentation to my wife on why we should actually do this. Thankfully, it worked.
37 years old: We sold Teles to Douglas Elliman (NYSE: DOUG) in a cinderella transaction after growing the business 10x in 5 years to $3.4 Billion. It was the largest transaction by two independent brands in US history at the time. You can google it.
After that, we sold additional companies that we had built to wind down our entire operating real estate portfolio of companies:
Property Management (Management Buyout)
Mortgage (Sold to Elliman as well)
Escrow Services (Management Buyout)
All the deal structuring knowledge from my Wall Street days finally came to help us. I did more transactions in 3 years than most bankers would do in their lifetime.
We also had multiple years of earn-outs. The gravy train worked for a while.
38 years old: I started Highland Prime, a private equity firm during my five-year non-compete. My entire idea was to take a minority stake in companies, and be a value-added operating partner to help them founders scale. We got up to 13 portfolio companies in the 5 year period and had some awesome exits. I fell in love with private equity.
We also launched the Kingston Lane tech platform. It was too early for its time (we did Ai and automation tools 5 years too early). We sold the assets as the business was dramatically affected by Covid.
The Multiplication Phase (Ages 42-45)
42 years old: Joined Real (Nasdaq: REAX) as President. Led the massive growth phase taking it from 6,800 agents to 27,000 agents 2 years, reflecting a $200M to $1.2B valuation at that time. All of this in the worst real estate market in 3 decades. I stepped down from my operating role as President in 2025 and joined the Board of Directors to guide the company.
45 years old: I then joined my best friends Alex and Leila Hormozi as a partner and President of Acquisition.com. I had known Alex and Leila for many years and had served as a friend and advisor on various deals, including the sale of GymLaunch, and also as they had begun to build Acquisition.com. In a lot of ways, it was coming home to something that I had helped with from the outside, but now I get to work on it from the inside.
A lot of people ask me about how the “negotiation” went with Alex and Leila. There honestly was no negotiation, it was actually a single email with bullet points that was turned into a contract. The part that was actually hardest for all three of us was ensuring operating guidelines that would not impact our friendship and love for each other.
It’s crazy looking back and writing it all down:
Started as a code monkey
Built 2 Billion Dollar Companies
Had 5 exits in the last 20 years
Traveled to dozens of countries
Made a bunch of money
Lost a bunch of money
Rang the Nasdaq closing bell
Built all of this with amazing business partners
And now I get to work with my best friends for the next billion
Did all of this while being a half-way decent husband and father
All without selling my soul… although sometimes it got pretty close.
The reason I even sat down and wrote all of this out was because my team wanted a timeline of events that they could use to build out content ideas and stories for me. And after I wrote it, I felt compelled to share it with you so that you can see that there was no linearity to any path or decision. It takes a lot of courage to do what you are called to do… but make sure that it challenges you, and you are willing to do whatever it takes to rise to that challenge.
Here Are 8 Unusual Lessons 25 Years Taught Me
Lessons are often repeated until they are learned.
When we are tired we are attacked by demons that we have already conquered a long time ago.
Your worst battle is between what you know and what you feel.
We need to speak the language of money to make more of it.
If you think practice is boring, try sitting on the bench.
Whenever you are presented two paths, choose the one that is harder in the short term and has a better story for the long term.
Your lack of commitment is insulting to the people who believe in you.
It’s only delusional until it works.
If you are grinding and you sometimes feel defeated, read this:
You didn't come this far just to come this far.
Never give up. Never quit.
The same courage that brought you here is the same courage that will take you wherever you decide to go next. Your origin story isn't your limitation - it's your competitive advantage in disguise.
Never give up. Never quit.
Here's what grinding for decades taught me:
Effort is the great equalizer
The harder you are on yourself in private, the easier life becomes in public
Most people quit when the unseen compound effort starts to work
The universe surrenders to those who refuse to surrender
Never give up. Never quit.
Keep grinding, because most people simply won't. They'll start strong, talk big, make plans, but when the grind gets real and the results stay invisible, they'll find reasons to stop. This is exactly why normal people don’t win.
Never give up. Never quit.
That's your unfair advantage.
The timeline is longer than you think, but the rewards compound in ways you can't imagine. Every day you stay in the game while others quit, you're building character that creates opportunities others just can't see.
I'm living proof that persistence beats talent, that systems beat inspiration, that showing up beats waiting for perfect conditions. Even for a recovering no-talent individual like me… who simply refused to quit.
Remember: It’s only delusional until it works.
Never give up. Never quit.
As a 24 year old, I just want to say thank you. There's obviously a million people online giving 'advice' but for some reason as I read this I was overwhelmed with emotion. Gratitude I think. Gratitude that I get to read your emails. Gratitude that you write them. Thank you Sharran
What an amazing read. Loved every part of this, especially:
"Never give up. Never quit.
That's your unfair advantage."