One year of Freelancing as Fractional CTO

First published on

I'm taking some time to recharge after struggling as a startup CTO for 5 years (with lots of ups and down). I have been working 40 hours a week in salaried positions from 2010 till 2023, and I decided to take it a bit easy. And with easy I don't mean to not work hard or to do simple work, but to not be 100% committed to a company for the long term.

In June 2023 I started freelancing as a Fractional CTO. It's for complicated projects or for companies that don't need a full-time CTO yet. It's been really great. In the past year I've:

  • Posted my availability once in my "goodbye to easee" LinkedIn post.
  • Been hired by 5 companies, who all found me through my own network.
  • Networked more than ever before. I suddenly have time for random meetings throughout the day.
  • Have not started an LLC (BV), nor got insurance, nor opened a separate business bank account.
  • Have signed only 1 contract for my freelance work (but some more NDAs) and almost never committed to a certain duration of the work. The paperwork takes time (and expensive lawyer overhead) and so far I've been fine with operating on a trust basis.
  • Have had all my invoices paid (by at most a week later than the due date).
  • Earned 2.5x what I earned before, while frequently working for only 3 days a week and took more vacations.
  • Had a great vacation to Egypt with my family.
  • Bought a framing shop with my wife where she's now working full-time.
  • And maybe most importantly: I've spent much more time with my kids and their school activities than ever before. I've been on school trips, did fun things with my kids after school, was invited to teach my son's class about electricity and inventions.

    As for the work, it's always been interesting and most of the time fun. I've:
    • Made plans and a technical architecture for a new product proposition, did competitive analysis and made plans to hire a team of about 40 engineers.
    • Set up an ISO 27001 ISMS in about 3 weeks, while working 2 days a week. That was a challenge but there was a lot of support from the full-time staff.
    • Interviewed about 40 people and hired a couple of them.
    • Set up k8s deployment with a helm chart and operator based on kopf, bringing my cloud skills back to excellence. (I had never touched kubernetes before).
    • Coached a software team on their way of working and individual engineers on their career tracks.
    • Helped management teams get a better grip of their technology stack.
    I'm doing this so I can start my own product company, and I don't find being a freelancer really fulfilling because there's no long-term perspective for me. But objectively speaking, going freelance is very very comfortable.

    Comments

    Post a Comment

    Popular posts from this blog

    "Security Is Our Top Priority" is BS

    First published on
    A couple of years ago I was asked to give a conference talk about software security. Well, actually I wasn't really asked, my company bought a sponsorship package with a speaker slot and I replied to the internal email asking for volunteers  🤣  Anyway, while preparing my talk, I realized a couple of important points about security that have not left my mind since: Security is limitless . You can always spend more effort to make things more secure. The same goes for quality, safety, employee happiness, etc. The needs of security are opposed to the needs of a convenient user experience . Improving one typically hurts the other. Now some organizations say "Security is our #1 priority". Really? You want to make something that has no limits your number one priority? I mean security is a good thing, but this seems a bit too simple? In fact, hollow marketing claims like that can make me a bit angry. In this post I'll help you understand what to make of statements like that...
    Read more

    AI programming tools should be added to the Joel Test

    First published on
    Here's a wake-up call to all CTOs: AI programming tools are getting freaking amazing and if you don't allow your teams to use them somehow, it will bite you in the ass in a couple of years. You will be slower and you will lose your best people. The infamous Joel Test is a list from the year 2000 of 12 things all great software companies do. Since then most companies have implemented Git and CI/CD, checking of three items, so we have some space left in the 2024 update ;) I believe "Do you allow your developers to use AI assisted development environments?" is a necessary addition. I get that you don't want your source code to end up on some OpenAI / Microsoft / Github server somewhere, sure, but find a way to use your own models or learn to live with it. Note that this is often not the same as "#9 - Do you use the best tools money can buy?" as blocking AI tools is about data security, not money. So why do I think developers need AI programming tools? I...
    Read more

    The long long tail of AI applications

    First published on
    Image
    Last year multiple companies asked me for advice. " We are evaluating this AI powered product, but do you think it makes sense at all? It seems a bit niche and we think ChatGPT might make this entire thing obsolete soon. " Long tail - credit to Wikipedia My answer so far has always been: "No, bare LLMs are not going to compete with this product." I think that people are failing to understand the distinction between different classes of AI companies. I see it like this: Foundational AI - creating models like GPT-4 (text), Sora (video) etc. Applied AI - using existing models to create smart applications. Note that there are also companies not focusing on AI - they will start lagging behind, let's forget about them ;) There are orders of magnitude  (!)   more companies that will deal with Applied AI than Foundational AI, and they will be very busy for decades to come. Here's why: To get the most out of LLMs, you have to ask the right questions. LLMs have acc...
    Read more