The email I didn’t want to write

I'm gonna be honest – I didn't want to write this email. That’s part of the reason it’s coming to you this week instead of last week.

As I've shared in the past, I'm a Type 7 Enneagram. (If you don't know your Enneagram, I highly recommend taking this test. I'm not involved with them. I just think it’s the best self-awareness tool I've found.)

Type 7s, like me, are called The Enthusiast. They are vivacious, filled with energy and ideas and action-oriented. Very typical entrepreneur types. 

But like all types, they have shadows, and one of them is that 7s avoid negative stuff: feelings, news, data. We prefer to silver line everything versus face the hard stuff.

I've made strides around this (topics for other emails), and it’s allowed me to see good and bad and, in fact, to see both as equally important and valuable.

But the reason I didn't want to write this email is because, well, it’s my 2025 reflections, and let's just say 2025 was a "character-building" year, versus my 2024, which was one big celebration after the next!

So let's get into some of the categories and then the big lessons:

My relationship with myself continued to evolve rapidly. I attended a couple of deep meditation retreats. I had a daily-ish practice of meditation, prayer and gratitude. 

I grew better at recognizing when I was in a state of threat/fear versus a state of openness and love. I paused more and I slowed down. I got more comfortable with being versus doing.

The biggest shift has been noticing my inner judge, who judges me and others. The result of noticing this judge has brought me closer to my emotions. This quote from Joe Hudson feels very apt:

"What feeling would you have to feel if you couldn't judge yourself/another person right now?"

It’s become a great shortcut to feel feelings.

My health and fitness were solid. I lifted, exercised and played tennis regularly. I DID get my first sports injury (SI joint), which was quite depressing. 

PT helped a ton, which is amazing, but I definitely started feeling middle-aged, and it slowed my tennis game down quite a bit.

D and I continued to take our marriage to new heights, although it hasn't always been easy. We’re more honest with each other and ourselves now than we have ever been. 

As both of us have explored our own personal/spiritual growth, we've become aware of patterns, resentments and pain we both have held onto (sometimes for over a decade!)

But our ability to hold space for each other has improved a ton. We communicate really well and repair rapidly.

The highlights in 2025 were when I threw D a big 40th birthday party (no Nelly this time) and then took an awesome 1x1 trip together to Turks and Caicos.

Being a dad is still easily my favorite thing about life. The kids are fun, AND funny. Endless joy. Learning the world from their eyes never gets old!

Ricky is 10 going on 25, Serena is 8 and Mila is 2. The age differences are really dynamic and refreshing.

Ricky is definitely a pre-teen: establishing his independence, pushing back constantly, arguing… AND he beats me at chess! I've got a lot of karma coming my way! Haha

Mila at 2 is a real joy. We know every moment with her is temporary, so we savor them. My highlight with her is our weekly swimming class, where she is an all-star.

Serena is my young mirror. She mirrors my silliness and my intensity.

If you follow this email closely, you’ll know we traveled A LOT. We skied several weeks as a family in 2025. Park City is my happy place.

We also took a huge 10th birthday trip for Ricky: two weeks in Japan. It was a mix of hustle, spirituality, shopping and eating. It’s definitely a core memory.

The highlight was the day trip I took to Hiroshima and Miyajima with Ricky and Dee’s dad. We woke up at 7am, jumped on a train, planned the entire day via TikTok and were home by 7pm — we barely sat down! Hiroshima was heavy, but very powerful. 

The food was great, and Miyajima was a HUGE adventure.

I can't wait to watch the kids grow up!

My mom was diagnosed with and cured of cancer in 2025. Her mom and sister both had breast cancer, so it felt inevitable that she'd get it at some point. 

She found it very early on and luckily, thanks to a couple of surgeries, some radiation and hormones, she’s in full remission with a minuscule chance of returning in the next 10 years.

While the ending was happy, it was a sad chapter, and one that brought a new appreciation for how fleeting time is!

GrowthAssistant continued to grow at a steady clip. The law of large numbers is real, though, and as we crossed $20M in ARR, it’s become clear that "what got us here won't get us there." 

So we are thinking about what areas to approach differently and how to do that. We leveled up the team with some amazing leaders.

Aux started the year with a breakout quarter and overall grew >100%. But it was a learning year. We went from big months and lots of profits to volatile months of gains and losses.

Overall, we ended the year pretty amazing in terms of a killer leadership team locked and loaded. 

Kasey is a rare breed of leader in her ability to navigate the growing pains of a company starting to get amazing growth.

The headline and where we landed were both great. But it wasn't easy. For the full year, we did $747,694 in revenue and $170k in profit. We had hundreds of entrepreneurs come through our programs. But it wasn't growing the way Andrew or I wanted. It was sapping his energy. In the fall, we had a breakthrough: Andrew was NOT living in his Zone of Genius. 

The BG biz in 2025 was a lot of content marketing, which drove to a sales funnel for our Sales Accelerator.

Elements of it captured Andrew’s Zone of Genius, but, overall, it was more his Zone of Excellence. 

Once we figured that out and exhaled, it opened up our creativity to think about what is next and we came up with The Next New Thing… And, importantly, got Zapier as our anchor sponsor!

I've shared a lot about this saga, but overall, this landed in a solid place. The business is profitable, our GM is great and stable and we're slowly paying off the debt. 

My hope is to find a home for it in late 2026 as we grow it a bit and the debt comes down.

Well… what else? 

As you may recall, we paused new business formation to build some AI chops. 

We went from knowing next to nothing to building tons of agents, using AI to code apps across the platform, building a strong POV and forming our… BIG SWING (coming next week). It’s been really fun to learn new things!

So what are my lessons from 2025?

That's literally the first prayer in all Sikh scriptures, so I think I've been saying it since I was a kid. But I think this year was when I first started to understand it and experience it.

What does it mean? Well, I have always categorized things as good or bad, right or wrong, happy or sad, and pushed myself to want the good, right and happy. 

And there's nothing wrong with that. 

The challenge is… it’s less whole. And as someone who has avoided sadness since I was a teenager, learning to see it, feel it and embrace it has opened up new levels of aliveness and freedom inside.

This applies to my marriage, my injury and business channels.

But let me give you an example: My mom getting cancer. 

Old me wouldn’t have let in the sadness of potentially losing her, or the idea that she won't be here forever.

I would have gone into fix-it mode and said, "It'll be fine! Think positive!" Instead, I sat with the sadness and felt it.

I slowed down my responses to news about it. I expressed to my mom how much I loved her (versus telling her it would be OK). 

I felt how scared she might be. It allowed me to appreciate her more, appreciate life more and love even more. I think the same has been true across the spectrum of life things.

This is also one I'll write a longer email on!

It took me 10+ years to build Ampush up and exit. And despite what you might read on Twitter, most ventures are about a decade. 

Building a company day-to-day is great stimulation. 

Every second there's a new email, new number on the dashboard or new client (or new problem!). It feels fast, and there are lots of feedback loops. That was my training pre-GX.

In GX land, that's happening everywhere, and at times I found myself getting caught back into that way of working and thinking.

That reactivity left me feeling depleted, and probably didn't feel great to the leaders of the companies. I was "too close."

Interestingly, when I stepped back and let the teams lead, they made great choices and I was able to help in longer term areas (e.g., strategy, capitalization, talent) and that worked WAY better.

I'm sure lots of VCs and others have realized this, but if you're going to be involved in multiple businesses, I’ve learned you definitely need to be patient, have a portfolio and let the teams lead.

I came into the new year knowing it was time to shift our approach as we write the next chapter of GX. 

Old me would have said, “OK, let’s set up a work-stream, analyze the five different options, take the expected value of them, do lots of data/research and then the machine will spit out the answer.”

New me took a very different approach: let my energy decide. I purposefully didn't give myself timelines or even specific options.

Of course, I had ideas in mind: more M&A focused, raising a fund, etc. But we tried some different paths. We kept reading and learning.

And then in September, the answer came. In one week, it felt like I kept getting sent the same article. 

I felt energy around the idea, started writing and thinking about what it could be. And I KNEW it was the idea (I’ll be sharing more about this idea soon).

So choosing to trust, then listening and waiting and knowing my energy. Big one.

There you have it, the email I didn't want to write!

jesse