[Updated] I launched yet another company

A few weeks ago, I told you I was turning this newsletter into a business.

Today, I am BEYOND thrilled to introduce you to Bootstrapped Giant’s new CEO, Andrew Warner, and our plan for growing this business.

It’s taken me 3 years to figure out what I needed, and then almost a year to convince him to take this role. Here is the story:

When I sold a stake in Ampush, I felt pride that I’d bootstrapped my company to $30 million / year. My friends in the Bay Area thought bootstrapped companies have to be small, 4-Hour Work Week lifestyle businesses.

I showed them I could bootstrap a giant…or at least I thought I did.

Then I looked at Red Ventures, the company that acquired a stake in Ampush. Red had bootstrapped to a BILLION DOLLARS in revenue.

I realized I wasn’t thinking big enough.

I have a few more beta invites to Superhuman’s Ask AI.

It uses your email to quickly answer questions like:

  • What time is my flight?

  • When do I take Ricky to Scouts?

  • What sessions will Ric's conference have about leadership?

To achieve my new vision, I launched Gateway X, and I committed to doing two things:

  • Build my own billion-dollar business by launching multiple companies

  • Teach other founders & open their eyes to what’s possible, the way Red opened mine

This newsletter was my way of teaching. I love teaching. My mom is a teacher. My leadership style is to teach. It’s what gives me energy.

So I invested time in this newsletter. As I wrote and interacted with readers like you, my vision grew.

I realized I needed to go beyond text, to podcasting, video, events, and more. Meanwhile, my time became more limited because my other businesses grew.

That’s why I convinced Andrew to partner with me and step in as CEO.

This role was SUPER unique. The 10/10 person needed to be:

  • Experienced: Has done the CEO thing, started and grew a company before because this is gonna be a real business

  • Strong in my “core four” CEO attributes: coachability, ownership, entrepreneurial rigor, and unfair advantage (he interviewed over 2,000 proven entrepreneurs!)

An unfair advantage here means they have a CONTENT brain. They can take all the work we do at the Gateway X companies and open source it so it’s valuable for you: my audience.

  • Energizer: We need to motivate and energize each other through our collaboration

  • Organized: They need to be analytical + keep a tight content calendar + analyze what’s working and what’s not.

Last fall, I called my old pal Andrew Warner. Believe it or not, HIS PODCAST was my first ever podcast appearance back in… wait for it: 2010!

Andrew bootstrapped an online greeting card company to over $30 million in annual sales. He called the company Bradford & Reed as a sales hack.

When he cold-called sponsors, he found that a call from someone who sounded like he was in a law firm was more likely to get answered.

Then he founded Grab.com, a game site that offered the world’s first billion-dollar jackpot, which was backed by Warren Buffett’s Berkshire Hathaway.

After selling those companies, he created Mixergy, the first startup interview podcast, which featured the founders of Y Combinator, Airbnb, and Dropbox. He’s built content operations there for over a decade.

I said: I NEED YOUR HELP. We started doing weekly calls. At first, he would just interview me to uncover interesting stuff going on at my companies.

Andrew’s genius was on full display in those conversations. I’d make a comment and instead of just moving on from it, he’d stop me and go, “Wait, Jesse… explain that in more detail.” Then he’d make a worksheet based on whatever I was explaining.

In fact, he’s quietly been assigning me these emails every week and then editing the hell out of them to make them great. He pushes me for better examples, to cut out BS writing, and a bunch of other things.

As soon as I saw his content brain, I knew this was what I’d been missing. But it goes further than that: he is tenacious. He is commercial. He pushes me to get shit done. And that’s an important part of success in this role.

So I’d love you ALL to give a warm welcome to Andrew Warner, the new CEO of Bootstrapped Giants. I’m introducing him so he can start to join our conversations, email you, and be a part of this thriving community!

We have ambitious plans to make BG the absolute BEST community and resource for founders who are building Bootstrapped Giants!

Andrew is on the left of the GX leadership photo from my birthday

On that front, this is what we’re working on now:

  1. Mentorship series: We’re recruiting other bootstrapped founders to join me in teaching what they’re learning as they build their companies.

  2. New products: We’re working on a few products to help you grow your business.

But we want to hear from you:

Andrew and I will be going live on Wednesday, June 12 to talk openly about how we plan to build this business and to hear from you about what you need from us.

Welcome, Andrew!!