Being a Bootstrapped Giant means…

In early 2012, I was sitting with a VC.

My first business, Ampush, had done $2M in revenue in 2010 and then $19M in revenue in 2011 while generating >$4M in EBITDA.

At 27 years old, I was already living my dream - running a fast-growing, profitable company with customers, a unique learning culture, and long-term ambitions.

One challenge for bootstrappers is competing for talent w/ large cos that offer better benefits.

I use Rippling PEO to even the playing field by offering:

— Medical, vision, dental, and supplemental coverages (typically only available to big cos)

— FSA/HSA accounts to save employees money

— Medical concierge to answer employee health care questions

Rippling is payroll, benefits and more. (I used them long before they sponsored!)

But the VC furrowed his brow as he saw my projections:

“Jesse, this is a cool lifestyle business for you and your co-founders. But it’s just not big enough for us. We need things that will be worth billions. I guess you’re just not ambitious enough. Good luck with your project.”

My face got hot and red. My first instinct was to fight back. To convince him he was wrong.

Instead, I tucked my tail between my legs and went home.

I was so proud of what we’d done in a short time and now I felt like it simply wasn’t enough.

A few months later, I visited Red Ventures for the first time. I’m lucky I did.

After the VC meeting, I felt insecure about Ampush. Living in San Francisco didn’t help.

I started to wonder if I needed a bigger vision or to just accept my business was capped at “lifestyle.”

Then I met Ric. Over 10 years, he had BOOTSTRAPPED Red Ventures to $100M+ in profits. His team had an incredible culture.

He was super ambitious. And when I shared my VC meeting with him, he shrugged it off:

“Jesse, don’t let their business become YOUR business. VCs play a different game than us entrepreneurs. Profits are the only thing WE can take to the bank. You can be as ambitious as you want while turning a profit.”

While I didn’t have the name, this was the start of Bootstrapped Giants.

As I built up Ampush, my radar was up for big companies that grew using their own profits.

The VC-backed companies dominated the narrative… and rightly so. Meta, AirBnB, Uber… these are truly incredible companies.

But for every one of these companies, there are hundreds of entrepreneurs who slaved away for years or more and got nothing out of it.

It became really apparent to me when I’d meet young people. In their mind, it was either go big or go home.

Because that’s all they knew. A lifestyle business was a bad word.

But the more entrepreneurs I met, the more I realized something was broken.

Most entrepreneurs I met wanted to 1) Build something new/cool/unique, 2) have an awesome culture/organization and 3) make enough money so money didn’t matter.

If I asked 100 entrepreneurs what they truly wanted, MAYBE 15-25 wanted to “change the world and go for broke” and MAYBE 15-25 wanted a lifestyle business. 50+, more than half, wanted something else…

… and yet there was no word for it. No advice, no content, no interviews, no discussion… NOTHING.

This is why I started: Bootstrapped Giants.

I want to be there for companies that are ambitious but grow off their own profits.

I want to make this a movement and ensure that people know this is an option.

It's funny, as you start to look at the world this way… you realize MOST companies we know and love are BGs.

Coca Cola? Dell? Even Microsoft and Apple barely raised any capital by today’s standards.

They all grew off their own profits.

I want to help build more Bootstrapped Giants.

And I want to help non-bootstrappers learn from our approach.

“So Jesse,” you might ask. “What does it MEAN to be a Bootstrapped Giant?”

Being a Bootstrapped Giant means you start with your customers because they are your investors.

Being a Bootstrapped Giant means you can build your culture however you want, because your growth is NOT “at all costs.” (Have you ever stopped to ask what it means to “grow at all costs”?)

Being a Bootstrapped Giant means you figure out your unfair advantages and pour them into your business.

Being a Bootstrapped Giant means you grow at a HIGH linear rate vs exponentially, but you turn a profit every year along the way.

Being a Bootstrapped Giant means the tax system feels rigged against you because you pay income taxes while VC-funded companies pay lower capital gains rates.

Being a Bootstrapped Giant means you know your PnL better than anyone else in the company.

Being a Bootstrapped Giant means you may feel alone because the startup world ignores you while obsessing over every junky idea that got a bit of venture money.

Being a Bootstrapped Giant means you can take home profits every year, instead of hoping for a once-in-a-lifetime windfall.

Being a Bootstrapped Giant means you never get the prestige of a label like “YC-backed” or “partner at Goldman” and get to make your own credibility.

Being a Bootstrapped Giant means investors are constantly chasing you because you don’t need them.

What would you add to this list? Hit reply and tell me.


PS, I’m a bootstrapper so I’m going to reiterate my sponsor’s message:

Being bootstrapped used to mean “no health insurance.” Rippling changed the game.

Rippling can help your team with health insurance, payroll, and more.

Rippling is the HR platform that my companies used (long before they sponsored me).