2023 Wrapped

“Your life is perfectly designed for the results you’re getting.”

My pastor said those words last year on January 1st, 365 days ago, and it really struck me.

On paper my results were good.

Good and happy relationships with my family and friends

CTO of a startup in an exciting field

High paying salary

What more could you want?

But with all this there was:

Stress, startup life can be really hard, and the startup I was with had really misstepped a few years ago, and I was left holding the bag

Health issues, I started 2023 trying out being gluten free because I’d been dealing with odd joint pain out of no where, I’d find that each morning when I woke up I could barely make a fist for the first few hours. When I’d do weight lifting, my favorite exercise, my elbows, wrist, and shoulders would get inflamed.

And frankly, being CTO, those were old dreams. Achievements I’d previously wanted.

I came to realize I had successfully designed what I wanted, achieved it. But forgot to keep designing as life changed.

So like any project, I sat down and started figuring out where I wanted to be, to start with the goal in mind.

Part 1 - The Self Assessment

This journey had actually started a month earlier. In earlier December of 2022, I had come to the realization I wanted to do something either new or more. I didn’t know what yet.

So on Twitter I started interacting more with the startup communities there. Just to spark interests.

I found I really enjoyed engaging with the various groups, met new people, and saw that there were a lot of people looking to get into software, but not sure how, or just looking for feedback on their journey.

This excited me. But what else excited me as well? And what didn’t?

In January I sat down and assessed 3 things.

Who am I?

What excites, energizes, and fulfills me?

What doesn’t excite me and drains me?

My goal would be to invest in 1 and 2, and divest in 3.

Who am I? — My Personal Mission Statement

Do you have a personal mission statement? Starting in early 2022 I had been exploring this idea, first started from an executive retreat where this came up, and then with my executive coach.

My own statement is “To equip and build up others”.

I had been doing it for years, from mentoring college interns, to encouraging growth in my employees, to traveling overseas on medical missions with my wife.

It’s who I’m made to be.

But how should I apply that?

What get’s me excited, energized, and fulfills me?

You can’t spend your life doing 100% of the fun things. I personally know, that if eat too many fun things, don’t invest in yourself, you’ll reap negative award.

That’s why I didn’t say just what excites me. I also added what energizes and fulfills me. Framed this way positive traits are revealed.

The are:

Solving problems - Life without work, without solving problems isn’t fun for me. I’m not a sit on the beach sun tan vacationer. Ask my wife and kids, we come back exhausted from our vacations, but full and recharged.

Variety - Doing the same thing every day sounds awful to me. I love to code, but I also love marketing, sales, working with my hands, talking to people, and more.

Teaching - I love to see people grow. To see their own dreams fulfilled and become more enriched people. I think I get that from my dad who’s own vocation really should have been teaching.

Business - I like work. I like solving problems that help others and think making money doing it is pretty damn cool. So obviously just solving various problems while teaching people isn’t going to satisfy me, I want more. Maybe it’s because I’m competitive?

What doesn’t excite me and drains me?

Not a lot to be honest. I’m an extremely curious person who loves variety. But there are a couple large things.

Bullshit - If I sense insincerity I’m out. There’s lots of ways this can come out. Disingenuous talk where you’re actions don’t match the outcomes for example.

Projects without Impact - I want my work to matter, either by solving problems or making people’s lives improve. I need more to what I work on, it can’t just be an interesting problem. Otherwise I know I’ll get bored of it. This is part of my Founder / Problem Fit equation.

Lack of Autonomy - I don’t like being pigeon holed (who does) and to not be in control of my time, focus, etc. I value autonomy quite highly, and as I’d discover later in 2023, this is a big one for me.

So knowing all this, I started to explore new ideas on the side.

Part 2 - Exploring New Things

December 2022 - April 2023

At the time, being fully employed, I knew that whatever I did to start discovering what was next had to be a nights and weekends thing. Even a well balanced life has 36 hours a week to work on a side project.

Finding that I really enjoyed engaging on Twitter (err X) and that I had a unique voice with my experience I started ProductFoundry.

ProductFoundry is born

I launched ProductFoundry on December 31st, 2023, 1 year ago! “A newsletter exploring how to build greatness into every SaaS product.”

I envisioned it as at first a newsletter, but knew I wanted to build it into something more. Over the next few months I’d dig into learning to write. Reading books and thinking through what I wanted to share engulfed much of my free time.

Woodworking

I also decided maybe working on something non-software was up my alley. I had gotten a CNC the year before and found some early success making desk trays, whiskey smokers, and a few other things. I had wanted to get it to $2k/mo.

But then AI happened.

AI?!?! AskJack is born

I was slow to seeing AI happen. It wasn’t till February or March I started realizing the insane impact of ChatGPT.

And I had just the right idea, where I saw my own company suffer in. Knowledge enablement. How do you effectively pass on information when it’s stored across various points, is in different people’s heads, or worse, the person who knew how to do X had left.

I had a working prototype in a couple weekends.

But then shit hit the fan and so did my free time.

Part 3 - Getting Side Railed

May - October

Starting in early May the company I had been head of engineering for over 10 years started negotiating it’s sale. Everything I had started working on got put on hold.

The misstep I referred to earlier was a failed Series B. The company I was working for, as is normal with a series B, shot for growth. But between not having product market fit and 2020, by the end of 2021 hit a cash crunch. I’ll share more about this story another day.

By 2022, with the VC markets freezing up considerably, even with a winning, but audacious plan in place, the board voted to sell us to a competitor.

At the time I even said it was probably the best choice going forward. I’m still torn, although I’ve come to realize I believe I was influenced incorrectly. And had I had better visibility into two key pieces I’d have not said I agreed.

In fact, just prior to the sale, I tried to resign. Only to find I had been named a key person and that if I quit I’d not be given a severance.

So instead on July 10th, the day of the signing, I had to fire very good and underserving people, since the acquiring company wasn’t looking for much in engineering.

Over the next 4 months I would quit twice more.

Once in late August, and finally in October. The option grants were not worth it. I didn’t fit culturally with the company and was finding it frustrating.

I wanted to do my own thing.

November 3rd was my last day.

And damn has it been awesome since then!

Part 4 - Starting From Zero, Happier Than Ever

November - December

On my birthday, November 6th, I had found myself unemployed. Having just quit the highest paying job I’d ever had.

And I couldn’t have been happier.

In the past two months, my co-founder and I, have been putting in long hours working on our two primary endeavors. Interweave and AskJack.

I’ve also revamped, ProductFoundry, finally got SaaS Stories going, and started another newsletter, the Infosec Monitor.

Lots of plans, but you can see I’m hitting everything I’ve designed for. Through ProductFoundry and chatting with others on X I’m able to teach and equip others. With Interweave and AskJack I’m solving real fun problems. I’m starting a new business with a great co-founder, and I boy do I have variety. Not to mention autonomy.

All in all 2023 has been great, but I think 2024 will be better.

🥂 everyone. I hope you’re designing you’re life as well.