What’s Next After Building 6 Companies?

Where do I go next?

This is another "journal in public" email (encouraged by Andrew Warner!). Give me your advice!

As many of you regular readers know, I've co-founded 6 companies in the last 4 years. It's been a super fun journey. We've shut down two companies.

Two are 8-figures, profitable and growing. One is Bootstrapped Giants (still <1 year old) and one is Unbloat (which is ready for a new home).

I've shared this year that we are not starting a new business, here's why. And that I'm also VERY excited by AI. Here's my game plan.

So as I sit here and envision a future where we have 3 profitable, thriving businesses by year-end AND tons of AI experience, what do we do?

I see 4 options:

Dude, you have 3 businesses all making money. Either spend more time on improving them or get a golf habit!

As I write, this option does feel more appealing. I've been craving more spaciousness from both time and energy standpoints.

Starting companies is fun, but the uncertainty of the early days can be brutal.

It’s a gift to run businesses that have repeatable-motion offerings which resonate in the market AND can be delivered effectively by the companies. And it’s especially powerful when all are generating steady profit.

There's plenty of offense to play in each company:

I want to actually write a book or create some sort of curriculum that involves a mix of personal growth, business rigor, spirituality and hustle.

There's opportunity to infuse AI in this business. That would be fun.

A million things, but one I've considered exploring is raising a co-invest fund so we can invest alongside our PE clients in deals we consult on.

AI will be big here, too.

There's definitely something appealing about only playing offense in stable businesses.

But there are big issues with hanging back:

• I believe AI is the second coming of the internet (only bigger), and I feel excited to dive in head first and help pioneer elements of it! I'm young (40) and in a great position to have a huge impact here.

• I am a creative builder and enjoy making new things, exploring new challenges — and this may not fully scratch that itch.

• I may get annoying to our CEOs.

• I may get annoying to my wife, who has never seen me during the workday.

I imagine some readers and friends says, “Jesse, stick to the original Gateway X vision. 2025 was a ‘gap’ year. You were tired. Now you have a huge list of ideas (many include AI) and you are better than ever at starting a business. You know what works!”

And we do have a formula:

A) Great CEO in early

B) Focus on an idea where you have distribution and see something unique

C) Stick with tech-enabled services that get profitable quickly

What's appealing about this idea is I DO think we could swing bigger given our scale.

We are better than ever at starting companies and know what to expect and when. This is what we've gotten "good" at (if that's even possible).

It definitely checks the box of “do more with AI and create.” It would be a good place to put my time (versus annoying our current CEOs or my wife).

This is what I built Gateway X to do and I’ve gotten better at executing on that approach.

But there are issues with this approach:

• At this moment, it doesn't feel appealing because of the energy required to be back in the zero to one phase.

• Related — I'm not sure where I'd get the time from, as I'm pretty slammed with current things.

Both of these could and likely will change by year end, though, which brings me to the next point.

• Scale — When I was starting with zero, new businesses felt good to get some quick momentum. Now we have some meaningful scale across the businesses, and starting at zero, even for the best idea, will take time and energy to reach any kind of scale.

My feeling about this approach: Meh.

Here's the idea: Take everything we've learned about launching new businesses, make it more scalable and build a "YC for Marketing AI Businesses.”

I could focus on three subtypes:

1. Tech-enabled marketing services

2. Software/SaaS

3. Content/Lead Gen

I could go out to the market of entrepreneurs and offer access to my network of buyers, my platform, lots of know-how and maybe give $$ to killer entrepreneurs building in the marketing category (and using AI).

In exchange I’d get 10-20% of their companies. It would all be run using the cohort model.

This idea is appealing because we've built tons of IP around what works and what doesn't when it comes to building companies.

I get energized by helping founders. I feel very confident that I can make a huge difference commercially and spiritually for founders.

This lets me see and learn tons about AI and marketing while helping build companies.

Having 10-20% of 10 companies can be just as interesting if not more than the current Gateway X venture studio model.

The other appealing thing is I wouldn't be getting my hands dirty in the same way. I'm not co-founding, so my responsibility and involvement would be near zero, outside of working with the actual CEOs/founders.

This sounds appealing.

But there are some challenges with this approach:

• Would I be too much on the sidelines?

• I assume the failure rate will be high relative to Gateway X, maybe 80%. If I'm coaching people to build bootstrapped companies, will that actual work economically?

• There's a reasonable lift with building out the program, attracting great founders, etc.

If you read my previous email on AI, this was the most obvious idea my Wharton-brain immediately jumped to.

I have a platform of cash-generating companies. We’re going to use AI to transform them this year. If that works, the best leverage and scale will come from buying businesses and transforming them.

We’d combine our new AI learning with everything we’ve used to grow multiple business.

What's appealing about this:

• It keeps me “in the arena.”

• It's a NEW-ish thing for me.

• It skips the startup phase, which has been grueling.

• It’s got lots of leverage.

• It feels like a skill I can use for the next 30+ years of my career to keep growth moving.

• I'll get to do AI stuff.

• I'll get to build up the holdco more.

• People I admire, like Ric Elias and Warren Buffett, do it!

Even writing this, I can feel the energy of this approach! More on that later.

But let’s consider the challenges:

• Buying companies is not a walk in the park. It involves different skills, capabilities and risks. E.g., sourcing deals, vetting them, working with already-moving machines and people’s personalities.

• "Deal life" can be crappy with all the urgency and false starts.

• Can AI + my platform actually make a huge difference in acquiring businesses?

• Am I just bored and looking for a way to bring new issues into my life? Haha

Those are four options before me. (Andrew is right, writing this out is super helpful!)

So how will I decide?!

First, I’ll ask you.

Second, I’ll share my process.

I'll write a deeper email on my decision-making process later this year.

It might surprise you to know that I think there is NO right answer here, so I won’t make this decision by modeling it or listing pros and cons.

No, the way I will decide is via PRESENCE.

First, just writing all this out is reminding me that I'm not living in TODAY. Today, each business has needs for me, and focusing on moving them forward is still today’s answer.

I'll focus on today's problems and what seems to make sense and trust I'll know the answer when it’s obvious.

Second, my energy. One cool part of this exercise was I could feel my body during it! I can tell you now, Option 2 did NOT feel appealing.

Option 1 felt calming. Option 4 felt EXCITING. I will let my energy guide my decision. I've learned to trust it.

So last, I will not make the decision: The decision will emerge this year. There are lots of moving parts, and the future is hard to predict.

I think if we put our heads down, parts of the plan will work and others won't.

Maybe during our AI projects we discover something so compelling we MUST start a new company.

Or maybe our impact on GA is SO big that the M&A path is a clear winner. Maybe there's a 5th option I haven't considered here.

My job is to stay present and let the answer emerge.

-jesse

PS I'll be in SF for the first time since I moved out. I'm getting together with old friends and new. Want to come out and say hi?

Meet me here.