2024 Retrospective (Creo)

When I ended my time at Stratasan in March of 2023, my original goal was to stick to a lighter working schedule that allowed me to spend more time with my (rather large-ish) family. After committing over a decade to a startup, I was ready for a change of pace for a time.

I had two major goals in mind coming into 2024:

Make “small bets” on side projects that might gain traction (either on my own or with a business partner).
Leverage my experience in the healthcare B2B SaaS (yes, it’s very specific) sector to earn income.

In 2024, my only “small bet” was Calendaristic. I spent more time in the first quarter of the year on this than any other quarter. As my consulting work (under Creo Advisory) became more demanding, side projects became more difficult to focus on.

What else happened in 2024, broadly speaking?

I co-founded the Nashville CTO Club with Josh Segall and Jim Siegienski.
I started Tech Founder Community to try to connect with other engineering founders and co-founders.
I connected with a lot of people in 2024. I continue to believe that this is the primary way that serendipity strikes. According to Google Calendar, I met with over 400 people in 2024. Calendly was a life-saver here.
- Many conversations started off with a meeting at some local event (Haley Zapolski and Josh Segall hosted many of these) or events at the Nashville Entrepreneur Center.
- A good many of these were referrals from folks I have worked with or for in the past. Referrals are the best compliment I can receive!

What went well?

The Nashville CTO Club got off to a great start in September. Kudos to Mr. Segall for being the primary driver of this thing. It’s obvious that Josh hosts a lot of events, because he though of a lot of details that I simply would not have considered. It gave this group needed structure.
The consulting / fractional business continued to do well. I was able to focus on clients that I felt I offerred the highest value (in my particular niche, relevant to my past experience) and turn down potential work for which I did not feel well-suited. A breakdown of how I billed categories is below. “P&E” is “Product and Engineering” - basically technical due diligence but for an organization instead of an investor.

Breakdown of how I billed services in 2024.

I was able to (mostly) stick to a four-day-a-week work schedule, which allowed me to prioritize more time with my family.
About halfway through the year I found myself doing a lot of interviewing for CTO and VPoE roles (I was the interviewer on behalf of my client). Given that this was somewhat of a rarity when I worked at one company, I used the opportunity to leverage the repitition here in order to improve my interview process. As Annie Dukes said, you can’t just gain experience by letting things wash over you; you have to be intentional about it! I feel like intentionally improving on my interviewing skills bore fruit.

What didn’t go well?

The Tech Founder Community languished. In June, it seemed like a doable thing. In July, baby #6 joined our family and I had forgotten just how much a new baby can take the wind out of your sails (especially in your forties!).
I spent so much time on Creo Advisory that I failed to get any other side projects off of the ground.

What are my goals for 2025?

I will launch three side projects into production in 2025. Two of these are known and in-progress. The third is a TBD.
I will block off more time for reading and writing. It’s easy to spend so much time on the application (consulting, building) that no time is spent learning and reflecting.
I’ll promote useful engagement within the Tech Founder Community, further refining it’s purpose and mission.

Other Thoughts

Presumably, I’m often hired as fractional CTO to help with the engineering team. But often I find that I spend more time with company leadership thinking about business strategy. Business strategy affects engineering strategy and vice versa. This is something that I enjoyed and would love to do more of. However, I’m not really sure if I want to market myself as some kind of strategic advisor!

This one is easy! Everything is Predictable by Tom Chivers and Thinking in Bets by Annie Dukes. The former I found via Five Books and the latter was via a conversation with Prakesh Sripathy. I am a fan of being uncertain and both of these books help think through uncertainty. I’ll write more about these too books later!