The Rebel’s Flywheel

In 2010, fresh out of Goldman Sachs and McKinsey, I teamed up with two Wharton classmates to start a business selling leads to online colleges.

The financial models were “bulletproof.” Buy keywords for $1, capture 5% of searchers, and sell leads for $40.

With 100k monthly searches for online degrees, we'd be making $100k/mo in profit. The math was beautiful.

We checked every assumption three times.

Then reality hit like a SLEDGEHAMMER!

We launched our campaigns and watched in horror as our money evaporated.

After ten grueling weeks of testing and tweaking, with just two weeks of cash left, we'd spent $10,000 on Google Ads and generated just 10 leads!!

The math was devastating! Each lead cost us $1,000 to acquire, but we could only sell them for $40.

We were losing $960 on EVERY single sale!!!

I'd left a prestigious consulting job for this. My savings were dwindling. Every night, I lay awake wondering if I'd made the biggest mistake of my life.

In hindsight, the problem was obvious. We were overthinking everything. Trying to reinvent the wheel.

❎ Overly complex landing pages using AJAX templates

❎ A bloated 1,000-keyword strategy

❎ 1 engineer who took weeks to ship a dropdown menu

Nothing worked. Our conversion rate was stuck at 0.1%.

Finally, out of desperation, we copied a competitor's website. Pixel for pixel.

Everything from the design to the messaging to the keywords.

I still remember the exact date we hit our first profitable week: May 23rd, 2010. The week of my 26th birthday.

The leads started rolling in. Suddenly we were profitable.

The failure wasn't in our idea. It was in our approach.

When I launched GrowthAssistant, I didn’t try to invent something new.

Instead, I took what already worked in engineering (offshore talent) and applied it to what marketing leaders were desperately asking for: affordable, reliable help.

Using this proven model, we built a $50k MRR business in 90 days.

With Aux Insights, the same approach succeeded, again. We adapted traditional consulting frameworks for marketing due diligence, delivering exactly what private equity firms needed.

This wasn’t luck or a fluke. It was a system. A repeatable pattern. I call it The Rebel’s Flywheel.

Imagine a heavy flywheel. At first, it's almost impossible to move. You push and push, and it barely budges.

But eventually, momentum builds. The flywheel spins faster and faster, powered by its own energy.

The same principle applies to building a business. Each turn of the flywheel requires three steps:

1. Start With Customer Desperation

Find what people are actively seeking and willing to pay for. At GrowthAssistant, we saw marketing teams struggling with bandwidth. At Aux Insights, we noticed PE firms desperate for marketing expertise.

2. Copy What Works

Don't reinvent the wheel. GrowthAssistant borrowed from engineering offshoring. Aux Insights adapted consulting models for marketing. Find what's working elsewhere and execute it well in your space.

3. Double Down on Winners

Do more of what works, cut what doesn't. At GrowthAssistant, we saw our first customers rapidly expand from 2-3 assistants to 10+. We poured all our resources into serving and finding more customers just like them.

The first turn of the flywheel is slow. It’s clunky. When most founders hit this resistance, they make one of three mistakes:

1. They stop pushing, convinced it's impossible

2. They change direction entirely, pivoting prematurely out of frustration

3. They reinvent the wheel, convincing themselves they need something completely new

But here’s the truth:

Investors buy moats, entrepreneurs dig them.

Entrepreneurship is a cycle of learning, doubling down on what works, and cutting what doesn’t. Rinse and repeat.

If you haven’t started, find something that works and make your own version. If you have started, look at what’s working.

Do more of that and cut the rest.

-jesse

P.S. Funny enough, with Kahani we did the exact opposite of everything in this post. We tried to reinvent the wheel and create something totally new. It flopped.

Go figure…

P.P.S. Last week I told you that we were hosting a meetup in Saint Louis. Thought you’d like to see some photos from the event.