Launching a company in 2025?

I sat at my desk and studied the body language of Nak (COO, Gateway X) and Adam (CTO, Gateway X). Both were leaning forward, a little tense.

They were waiting to hear what I would say next…

Finally, I started:

"The more I think about it, the less excited I am about starting a new business in 2025. Let's commit to NOT starting a new business in 2025!"

They didn't have to say anything. Their bodies immediately relaxed, and their faces calmed.

"We couldn't agree more."

One of my favorite parts of this newsletter is something Andrew calls "journaling to process my learnings."

It's helpful for me to reflect on what's happening and why, and hopefully, it serves you in some way.

So let's talk about where we are and some of the reasons why next year, we want to do less - not more.

Let’s look at where we are first.

Our 4 businesses

• GrowthAssistant

• Aux Insights

• UnCo (aka Unbloat)

• Bootstrapped Giants

All four are PROFITABLE! Hooray!

Each company has a CEO/co-founder or GM who focuses on the day-to-day of the company.

GrowthAssistant is doing great. It will cross $20M in ARR month, it's profitable and the team is growing.

The focus there is hiring leadership ranks, and getting consistency in growth of new revenue via marketing and client expansion.

My role there is coaching Adriane and other leaders, strategizing, and continuing to help with marketing/sales.

Aux is also great. The PMF is very strong there, we have a handful of PE firms who call on us regularly and we've seen a lot of repeat work (the ultimate sign of success).

The business (by its nature) is more lumpy and takes a long time to build up the pipeline. Kasey the CEO is a force of nature. There's also a killer team there.

It feels like in 6-12 months, we will be in a very stable, growing place.

UnCo, you may remember is somewhat distressed (newsletters 1, 2, & 3). It's making $30-40k a month but has nearly $1M in debt to pay back. Ugh. It feels like a distraction, but it is what it is. It is pulling time from all 3 of us.

Bootstrapped Giants is new and fledgling! It will be profitable in its first year. We have lots of engaged readers like you and tons of happy customers from our Blueprint and Accelerator.

Plus we have some great sponsors in beehiiv, Superhuman, and Notion.

BG feels like Aux a year ago (which feels like GA a year ago). That’s because BG is figuring it all out while we go— new team members, mistakes, challenges, etc.

That's what the portfolio looks like. So, why would we decide to pause starting a new co?

There are a few reasons:

Most startups and founders are the types who like to create, build, and go PEDAL TO THE MEDAL to scale.

The idea of scaling endlessly is what they live by. No brakes. But this is a mistake…

There comes a time in every company when it's better to slow down or prune than to grow faster. How do I know the time is right?

• GrowthAssistant continues to grow profitability

• We sell/shut down UnCo with no loss

• Aux stabilizes, takes less of our time, and is on the right path

• BG has a repeatable, scalable business model (acquire emails, sell educational products, build a community)

If we accomplish these goals, we are "home free!"

By that I mean: we have enough cash in the system to start more ventures, invest in companies, and, hell, maybe even do some M&A!

It sets us up for the next decade to have multiple profitable companies in different industries.

• GA flatlines or declines (eek!!)

• UnCo falters early in 2025, we are on the hook for nearly $1M

• Aux continues to be lumpy (which means we can't really pull any cash from it)

• BG is a one-hit wonder and keeps scraping by…

I think our chances of the "good vs. bad" scenario are 70/30 but let's handicap and say it’s 50/50.

Now, throw in starting a NEW company. No matter how good the idea is, how great the co-founder is… they are going to worsen our odds of the successful scenario.

A1) Start a new company AND hit portfolio goals - WOW, this would be amazing!

A2) Start a new company and MISS portfolio goals - the new business would be useless here and the entire operation would be at risk. No more swings. Code red.

B2) Don't start a new company and MISS portfolio goals - pretty much the same as A2.

B1) Don't start a new company AND hit portfolio goals - this would be great and buy us lots of time to take more swings.

What you can see quickly here is that hitting portfolio goals is the KEY thing to solve.

Another new company won't change the story either way, but hitting the goals will make all the difference.

I think it's super important to realize that doing more stuff ALWAYS increases risk. Partially because they always take more resources (aka cash), but more importantly, because they take MENTAL BANDWIDTH.

In my experience, it's hard for any human to do more than a few things at once.

Let’s move onto our next reason.

It's taken me a long time to know myself (and this journey is still in flight).

One thing I've learned is I'm a "Type 7" enneagram.

Nicknamed “The Enthusiast,” I am creative, energetic, and gregarious. But I can also be avoidant, scatterbrained, and overly intellectual.

One specific behavior of mine is to avoid negative feelings/results. So my pattern is when things get tough, I look to a shiny object or a new silver bullet.

I did this even while the CEO of one company.

Of course, I’ve also found myself doing it at Gateway X…

Learning this pattern and seeing it and surrounding myself with people who know it and can help me see it has been HUGELY valuable.

In this specific instance, when the portfolio feels messy, I notice myself going back to the idea list to find something ELSE to get excited about.

Luckily, I'm aware enough to know that's a pattern I use to avoid reality. I can breathe and gently bring myself to confront what's already in front of me.

Over the years, I have learned to trust and follow my energy.

This entire journey of Gateway X has been a big experiment for me. When we started, I had no idea if any of this would work.

Could I actually start multiple companies? What aspects of my time would it take? How much/how long before a company felt stable and independent?

3 years in, and I think I'm starting to get answers.

We’ve seen success when I am highly involved in the early parts and in bringing revenue/talent to the table. That's not being the CEO, but it does take a lot of my time.

I've noticed my energy and happiness waning when I'm doing it in too many places at once.

The last few months have felt that way and as I looked ahead to next year, I decided that it'd be nice to have "extra" time versus always feeling like I didn't have enough time.

This isn't to say what's right or wrong, it's just following and trusting my energy.

How are you thinking about your plans for next year?

I just gave you the 3 ways I’m considering whether now is the time to prune or double down: Risk/reward, self-awareness, and following your energy.

To apply this to your own business, zoom out and think about 2025. A year from today - what do you want it to look like?

Dream a little. Then ask yourself this:

1. What will make or break me and am I giving that the right attention/energy?🔋

2. How do I want the next year to feel day to day? IS that energizing?⚡

Those questions will guide you to right-sizing your plate and focusing on business success! Have a good week.

-Jesse

PS I want to meet you in person. If you’re in St. Louis, come meet me and Andrew in person, here.