Trust Your Path: The Only Shortcut Is the Long Way
Twenty years of growth marketing, countless failures, and one exit later—here's what I learned about building something real. There is no shortcut. There is only the path.
Robbie Jack•Dec 30, 2025Everyone wants the shortcut.
I've spent 20 years in growth marketing looking for one. I've tried every hack, every arbitrage, every angle. I've made money fast and lost it faster. I've watched sites go from zero to a thousand dollars a day and back to zero overnight. I've scaled on credit cards and walked away from wins that didn't feel right.
Here's what I know now: there is no shortcut. There's only the path. And the path is yours.
This is the story of how I learned that.
The Kid Who Hid What He Knew
I built my first PC in elementary school so I could play video games. Old IBM 386, Windows 3.11. I didn't know it then, but I was teaching myself how to learn. How to figure things out when nobody was going to show me. How to solve problems because I wanted something badly enough.
Pretty soon every adult I knew was asking me to fix their computers. Some offered to pay. I started pretending I didn't know how.
Even as a kid, I understood something important: being useful on other people's terms is a trap. If I became the IT guy, I'd always be the IT guy. So I hid what I knew and protected my path before I even knew I had one.
View Source
Then a friend showed me view source in Internet Explorer.
I don't know how to explain what happened next except to say that something clicked. I saw the code behind the page, and I understood that everything on the internet was built by someone. Which meant I could build it too.
I devoured HTML for Dummies. I built terrible little websites for the pure joy of making something exist that didn't exist before. I couldn't stop. The obsession had found me.
That obsession turned into building sites for my middle school. Which turned into an internship at an enterprise software company. Which turned into real skills: real languages, real databases, real standards. Each step made the next one possible.
By college I was running web development for the University of Florida's Office of Technology Licensing. They wanted to rank in Google, so I figured out SEO from first principles. We outranked Stanford.
I was 20 years old and I'd just beaten one of the best universities in the world at their own game. That feeling—the feeling that I could figure anything out if I cared enough—never left me.
Easy Money and Empty Wins
I discovered AdSense around then, slapped it on my sites, clicked my own ads a few too many times while testing, and got banned.
First real lesson: the rules matter even when opportunity is everywhere. The game rewards those who play it long.
One afternoon at Barnes & Noble, I was reading a thick PHP book when a stranger struck up a conversation. He invited me to his mastermind. Turned out they were all affiliate marketers, and AdWords was brand new—basically printing money for anyone paying attention.
I traded code for marketing education. Started buying traffic for dating sites. Turned $5 leads into $10. Scaled the whole thing on credit cards.
It was working. I walked away anyway.
The money was good but the game felt hollow. Sketchy. I didn't want to build something I couldn't respect, even if it paid. So I started over.
I took a corporate job. Excelled. Got promoted. Then 2008 happened.
The recession hit. Friends got laid off. I watched executives play politics while everyone else did just enough not to get fired. The building felt like it was full of people waiting to die. I quit in the middle of it all and went back to freelancing, because unemployment seemed better than slow suffocation.
A Thousand Dollars a Day, Then Nothing
I spotted a keyword exploding in Google's search data: "facebook login."
Bought the domain. Threw up a WordPress site. Hired cheap writers. Ranked number one within weeks. Over a thousand dollars a day at 99% margins. I thought I'd cracked the code.
Then a Russian black hat SEO group pointed their link farm at my site and Google nuked it from the index.
Gone. Overnight. Back to nothing.
This is the part of the story where most people quit. Where the lesson is supposed to be about resilience or grit or getting back up. But honestly? I didn't feel resilient. I felt tired. I'd been chasing wins that kept disappearing, building on ground that kept shifting.
So I did something that didn't look like progress at all.
36 Hours West
On a whim, I drove 36 hours from Florida to Colorado to snowboard for a season with a good friend. I told myself it was temporary. A break. A reset.
That was 2010. I never left.
I spent that winter riding powder and reading books and doing just enough freelance work to stay alive. I had no plan. No trajectory. Just space.
Looking back, that season was the most important thing I ever did. Not because of what I built, but because of what I didn't. I stopped chasing. I let myself be still. And in that stillness, I started to figure out what I actually wanted.
Unemployable by Design
Before I even moved to Denver, I was networking the city on LinkedIn—adding strangers in tech, studying the landscape. I've been on the platform since graduation. Never needed a resume. I showed up at every meetup I could find, and one of those early connections led to building an ecommerce site for 50 Cent.
I still can't believe that sentence is true.
I joined my first real startup, FullContact, right out of TechStars Boulder. Loved the work, loved the energy. Then they hired a manager. I lasted 10 months before I quit because I realized I physically could not work for someone else. Some people aren't built for hierarchy. I'm one of them.
The week after I left, a random stranger bought a domain I'd been holding for years—realestatebroker.com—for $75,000.
Suddenly I had two years of runway to read, tinker, snowboard, and figure out what I was made of.
The Four-Year Sprint
What I was made of turned out to be this: I cold emailed Boosted Boards, landed a job running growth, and took them from fresh out of YC to $10 million in revenue in year one. Rebuilt the site myself. Ran every ad. Figured it out as I went.
I left after 10 months—burned out and butting heads with the CEO—but I'd proven something to myself. I could do this. Not in theory. In practice.
I convinced a good friend who'd just sold his CrossFit gym to cofound TrueCoach with him. We started charging before the product was ready. I ran Facebook ads on day one with almost no budget.
We applied to TechStars Boulder and got cut at the last minute.
It stung. We kept building anyway.
Six months later, TechStars Chicago let us in. Troy Henikoff believed in us when nobody else would. That belief changed everything. Not because of the money or the program, but because someone saw what we were trying to do and said: yes, this is real.
We raised a small seed round. Moved the company to Boulder. And I put my blinders on.
For four years, I did nothing but focus on ads with a kind of psychotic intensity. I ignored everything else—every distraction, every shiny object, every voice telling me to diversify or hedge or play it safe. I found the lever and I pulled it until my hands bled.
It worked. $10 million in ARR. Thirty employees. Third office. We were sprinting and we couldn't see the finish line but we knew it was coming.
March 10th, 2020
Then a PE firm called out of nowhere.
Six months of diligence. Endless calls. Spreadsheets. Lawyers. The kind of pressure that makes you question everything you've built.
We closed on March 10th, 2020.
The exact day the world shut down.
I woke up that morning with real money in my bank account for the first time in my life. No office to go to. A new boss I didn't choose.
Thirty days later, I quit.
I was completely unemployable. And I finally understood that this wasn't a bug. It was a feature.
What the Silence Taught Me
Lockdown forced a kind of stillness I'd never experienced. No conferences. No meetings. No momentum to hide behind. Just me, alone with myself, in an apartment that suddenly felt very quiet.
I started meditating. I stopped running.
Then I met my future wife. Randomly. In the middle of all that quiet. A year later we were married. I bought a house on top of a mountain. Spent three years angel investing, advising, and consulting—learning what I knew and what I didn't.
Now I'm pouring 20 years of everything into GrowthMarketer.com.
What I Didn't Tell You
I'm making it sound cleaner than it was.
Along the way, I had clients who didn't pay and a business partner who put his hands on me. Employees who betrayed me. Tension with my cofounder that almost broke us before we worked through it. Hundreds of investor rejections. Aggressive VCs who tried to push us around. Sleepless nights doing payroll math in my head, wondering if we'd make it to the next month.
I got burned. Lied to. Rejected. Wiped out. More times than I can count.
I was told I wasn't CMO material.
I was told TrueCoach was a "cute lifestyle business" and not investable.
For most of my life, I was fueled by proving those people wrong. Tell me I can't do something and watch me try to destroy you with results. That chip on my shoulder carried me further than talent ever could.
But here's what I've learned: proving people wrong is a powerful fuel, but it's also a trap. You end up running someone else's race. Chasing someone else's scoreboard. Building your life in opposition to people who stopped thinking about you years ago.
These days, I get my motivation from different places. The desire to be the best version of myself. To protect my family, my body, my mind. To do as much good as I can while I'm here.
The anger is still there. I just don't let it drive anymore.
The Only Shortcut
So what's the point of all this?
I started by saying everyone wants a shortcut. That there isn't one. But that's not quite right.
The shortcut is trusting your path.
Not someone else's path. Not the path that looks impressive or safe or obvious. Your path. The weird, winding, inefficient one that only makes sense in retrospect.
Every skill I learned—even the ones I hid from adults as a kid—compounded into something I couldn't have planned. Every failure taught me something I needed to know. Every time I walked away from money that didn't feel right, I was building the foundation for something that did.
The path was always there. I just had to trust it.
What I'd Tell the Kid Building PCs in His Bedroom
Keep betting on yourself. No one else will do it for you, and no one else can.
Keep building skills that compound. The things you learn in obscurity become your edge in the spotlight.
Keep showing up before you're ready. Readiness is a myth. Action creates clarity.
Keep walking away from things that feel wrong. Your gut knows before your brain does.
Keep finding the people who believe in you before you've earned it. They're the ones who matter.
Keep letting your work speak for itself. Everything else is noise.
Life is too short to listen to doubters, haters, and naysayers. They're not on your path. They're on theirs.
Turn doubt into fuel. Then outgrow the need for it entirely.
The best is yet to come.
Here's to 2026 being the year we trust our paths.