Hello and happy Sunday!
I am writing this on the heels of accepting several people into my LinkedIn network who graduated with me in 1996. We all agree it feels more like ten years than thirty years. I silently toasted them yesterday afternoon in my backyard for earning our respective degrees from the University of Waterloo.
This week, I want to talk a little about something I did in a moment of whimsy. I want to talk about fractional CTOs. I am a member of several fractional groups, and I struggle with that. I hear people suggesting methods to build new relationships on LinkedIn, what services are good for outbound selling, and how to target your ICP.
I have spent some time talking amongst these groups, including creative deal terms, owning the IP, revenue share, and blends of equity and cash in order to help people build interesting stuff.
I have used many of those blends myself, and I could also see people’s eyes glazing over as I explained the value in doing lower-cost projects that are personally interesting.
It took me some time to realize that there were few to no people in these groups who considered the various projects interesting enough to lower their prices. Most of them would rather find some way to persuade an existing customer to extend their ramp, and in some cases, that meant making up work or possibly doing something that isn’t constructive.
You might be shocked to hear that. I have mostly done fractional work on an inbound basis for people who need help. Generally, I work myself out of a job doing these tasks efficiently. Sometimes I do stuff on a rolling fraction of a percent equity grant in a company. On more than one occasion, they come back and come up with excuses to put that vesting on hiatus. Of the times that stuff has been put on pause, precisely one company has reached out to re-engage, and then they were shocked when I pointed out the size of the gap between when they put things on pause and how much it costs to bridge that gap due to their own selfishness and shortsightedness at preserving their cap table.
I had just finished a prospective customer conversation that did not feel good when I realized I was not in it for the same thing that other people are.
I care more about the ideas and the work than optimizing the final dollar on the other side of it.
I also don’t sell-in warranty packages or propose contract extensions for stuff that does not make sense.
I was listening to one of the people who is all in on the fractional model and realized that we are not playing the same game, and as they were going through the different things that they optimize for, and how they turn their technical talent into a heartless revenue pump, I concluded that one of these kids is not like the others, and one of these kids just isn’t the same.
And that kid is me, in case you missed it.
I think that the big takeaway from this is that in some cases, it probably makes sense for a company to have a fractional CTO for a period of time.
I also realized that for a company that only wants to have a fractional CTO in perpetuity, I do not want to be that guy.
I think that the best fractional CTO projects are try-before-you-buy dating relationships, and that it is with a company that has growth prospects, where having a CTO is a long-term thing that they need in-house.
If you are just babysitting some business part-time, are you really doing anything interesting enough to merit a CTO relationship, especially if it is not on a growth trajectory?
That sounds like the perfect customer for a fractional CTO who does not want to go all-in on a growth opportunity, and I bet several people in these groups would thirst after that five hours a week engagement.
But that is not me.
I have concluded that most fractional CTO assignments are polite fiction, especially the ones that stretch into multiple years. I also question the ROI of that investment if the company is just plugging along for that window of time. If your CTO is not bending you into a hockey stick where your business is growing, I have two questions:
- What the fuck are THEY doing?
- What the fuck are YOU doing?
When that realization hit me, my fingers took on a life of their own and opened up my LinkedIn profile, moving from key to key with furious intent. The lightning-quick stab of each key felt satisfying as I typed “A” “N” “T” “I” and “-” into my title, prefixing Fractional CTO.
And that is how the anti-fractional CTO was born.
I enjoy being a part of a great team.
I enjoy putting significant focus on great problems.
I enjoy the level of gambling with outcomes that come with that.
Maybe I do not have a serious enough stamp-collecting hobby where I am willing to make that time vs money tradeoff at a level less than 110%.
Maybe I didn’t win the lottery at a previous startup big enough that I can do this and not care about the financial outcome.
Or maybe I am addicted to the sport.
Regardless, I think that the anti-fractional CTO label fits for now, given all of the above.
Thank you for reading along.
I am going to do something I have not done in a long time, and I am going to attempt to dethrone myself as Amazon’s Worst Affiliate Link Marketer.
This post was brought to you by A Parade of Horribles. This is the eighth book in the Dungeon Crawler Carl series. You should go buy it and read it, it is a bestseller. If you click here for it, you will donate a percentage of the proceeds to the “Ha ha! Thanks for the nickels, Jeffie B” fund, as I am an “Amazon Affiliate Marketer”.
If you have no idea what this is, then take a look at the first book, which is also an Amazon Affiliate Link, over here. If you enjoy reading my blog, there is a very high likelihood you will enjoy this book.
In fact, I guarantee you will like it (not an actual guarantee).
If that doesn’t persuade you to go click that link and buy something, then nothing else will.
Thank you for reading along and clicking all of my Clearly Labelled affiliate links.
You all have an excellent week!
If anyone needs me, I will be raw-debugging stuff in production with multiple AI tools, like a total degenerate.
