A look inside Bootstrapped Giants

I'm on spring break with the family in Park City, so this week Andrew is stepping in to update you on some of what we’ve been up to at BG. - jesse

The other day, my brother asked me, "Why'd you bother partnering with Jesse on Bootstrapped Giants? You've been an entrepreneur your whole life. You don't need him."

I said, “I don’t need him or his venture studio to build companies, but I like working with him and Gateway X to accelerate what I could do on my own.”

Since he read my book on probing questions, he hit me with one of my own techniques and asked, “For example?”

I told him how, when I wanted to launch the Sales Accelerator, I created a plan to build it out over a year.

Jesse said, “Let’s figure out how to do it within 2 months.” Or, how less than a week before launching it, I decided to use live sales calls and needed a CRM.

Within 3 days, Nak & Adam built out the CRM I needed.

That’s what Gateway X does for its portfolio companies: Accelerates their growth.

It’s also what we, at Bootstrapped Giants, want to do for you: Accelerate bootstrapped founders’ growth. We started out doing that with this newsletter.

But, as you’ll see below, we’ve expanded beyond that.

The Accelerator was my baby, but the first round was tough to put together.

I wanted to take all the sales material from Jesse’s Gateway X and Ampush and make them accessible to founders who aren’t enmeshed in our culture.

I underestimated the number of research interviews it required, how much time it took to organize all the sales training, and how tough it would be to harmonize my teaching style with Jesse’s.

I’ll give you one little example. Jesse likes dense, McKinsey-style slides. I like the 1-concept-per-slide approach.

Do you have any idea how many tough conversations we had about how to find a teaching style that worked for both of us?

It’s behind us now.

That was all during Cohort 1.

But, as Jesse keeps saying, we have a culture of feedback here. So at each step in Cohort 1, we kept asking, “What would do better next time?” and kept adding improvement ideas to our “running retro” list:

Making Cohort 2’s experience better was as easy as going through our lists and implementing.

833 is our answer to “What would the mini-Gateway X experience be like?”

As a founder of a company that’s backed by the Gateway X venture studio, I get 2 things:

1) Ideas: This includes help brainstorming future business direction and guidance when I get stuck getting to my destination.

2) Time: The Gateway X team set up my incorporation paperwork, made calls to book sponsors, created our first project management software, ran our whole hiring process to grow our team, etc.

In return, Gateway X gets majority equity in Bootstrapped Giants.

With 833, we’re working with 7 founders to give them the first item on that list: the ideas.

Jesse and the team get on calls with 833 members to go over their business plans, elevate their vision for how big their companies can be, and support them when they’re stuck.

These happen on team calls, private 1x1 calls with Jesse, text, etc.

In April, we’re bringing it to NYC for an in person 2-day intensive. We rented a gorgeous space in Manhattan. We’ll jam on ideas and spend time together.

One thing that always bothered me about the education space is how much time and money companies spend on landing new students, and how little attention they pay them once they join.

To close sales, they’ll test ads, tweak landing page, test upsells, increase ROI, etc.

But once someone joins, they stop being customer-centric optimizers. If a student doesn’t get the result they wanted, the program’s response is a version of, “Some people just don’t want it badly enough.”

In the first cohort of the Sales Accelerator, I spent over 20 hours each week checking in on members, Zooming with them, and doing anything I could to help them make progress.

I neglected a big part of the business in order to do that, and I still couldn’t do it as well as I wanted.

To help with this, we hired Vernon T. Foster II to build out Member Success.

In his first week, he sent personalized messages to every single member of the Accelerator, Zoomed with people who were stuck, and helped everyone make progress.

As a result, the members I was worried about were the ones closing sales.

I think more companies need a member success function to ensure customers get the results they signed up for.

This is a tough one for me.

The vision I had was to buy ads for our newsletter and cover the cost of those ads with Sales Blueprint sales.

Ampush, Jesse’s company, pioneered Facebook ads, so I thought we had an advantage. Jesse recruited one of his best people to run ads for Bootstrapped Giants.

The former Ampusher built an incredible tracking dashboard, had our team design ads for him, and started to buy ads.

One of my favorite discoveries was seeing homemade-looking (ugly) ads, like this, do well:

$33,600 later, we only grew 8,900 subscribers from ads.

We kept trying to improve our ads. I think that was a mistake.

I think I know our real problem. Our onboarding pages suck.

This is our subscription form:

We need to rethink our full funnel before we go back to buying ads for it.

This month, I stopped ads. I’ll work on a new funnel next month.

One of my favorite parts of business is immersing myself in my customers’ worlds and uncovering needs that they didn’t even know they had.

Surveys are fine, but they’re not enough to find the problems people don’t know they have or don’t like to talk about.

Years ago, Nathan Barry came to a meetup I hosted at my office. As we talked, I saw that he was anxious.

So I asked him about it. He said that he was thinking about mortgaging his house.

“Why?” I asked.

He was building ConvertKit (the email software) and he ran out of money.

“Why not raise VC funding?” I asked.

He said wanted to keep his company and culture as they were.

There’s a “quirkiness” that he wanted to maintain. He liked serving “creators,” a group that, at the time, was considered unprofitable artist-types.

He liked sharing profits with his team. He liked making his company as much of an artistic expression as a commercial success.

He was willing to mortgage his house to keep that culture. That’s how much culture meant to him.

Surveys don’t give that kind of insight.

In that meetup, I realized that culture mattered to my audience, so I started hosting courses with people like Jason Fried of Basecamp, founders who built culture-first businesses.

Culture training was an incredible hit with my customers.

(I also wrote Nathan a check for $20,000, as a no-interest loan to be paid back when and if he wanted. He paid me back, and we continue to be friends.)

But meetups aren’t just about understanding customers. Sometimes cool things like this happen:

This year Bootstrapped Giants is stepping up our meetup game. Starting with 3 meetups in 3 cities. People are flying in from all over to join us. If you’re anywhere near them, come say hi.

Austin (my city)

St Louis (Jesse’s home town)

New York (where we’re hosting 833)

~ Andrew