Reinvent Yourself: A Tale on Changing Career Path, Connecting Dots and Finding Your Own USP.

From CTO to Tech Evangelist, to Investor. What’s next for me?

Over the last 25 years I’ve occupied many positions in the tech industry. I’ve started as a software architect, evolved into a CTO, shifted gears to become a Tech Evangelist, and more recently I’ve also been an investor as an MD at Techstars. Up until recently I’ve had a very opportunistic strategy when it comes to my next roles. Every role builds up on the next one, and I always make sure I’m gonna learn a whole new range of skills in order to not get bored and grow as a person. 

  • As a CTO I’ve learned to drive a technology vision to execution, build a good engineering team, and design products. 
  • As a Tech Evangelist, I learned how to build communities, become good at networking, and build a conference from the ground up.
  • As a MD at Techstars, I learned about investment, how to better read people, what makes a great team, and all kinds of engineering fallacies. 

After leaving Techstars I wondered what the next thing would be, which is built on top of  everything I’ve learned so far. Turns out, I have a strategy for that! Or kind of… As an entrepreneur, I tend to follow my instincts, trust myself, grab opportunities, iterate, and see how things can evolve. From there sometimes a larger vision emerges. I gave myself one year to figure things out, which provided ample room for experimentation. 

Creating a value map for yourself

During that time, to orient myself, I decided to map out the skills that I have, my weaknesses, what I like to do, what I don’t like to do, so I could come up with my personal Unique Value Proposition.  It boils down to this question: What can I offer to the market that is unique, built on my acquired skills, and where I’ll have fun? So here we go…


– Strong engineering background
– Understanding of team dynamics
– High empathy
– Understanding of product development and how it connects to technology. 


– Not so good at working on my own, without a team. 
– Not great at anything related to organising my time

Things I like:

– Helping entrepreneurs 
– Sharing knowledge
– Connecting people

Things I don’t like

– Working on long term projects, full-time
– Not being in control of my own time

My initial idea was to build an accelerator for CTOs. As it turns out, very little support is offered to CTOs at an early stage. That led me to being a CTO In Residence in no less than 6 Techstars programs during this year. I’ve always loved my work at Techstars – as an entrepreneur, I resonate with the mission of helping entrepreneurs succeed.

Allowing Yourself to Try Something New

At the same time, I came across the opportunity to perform a Tech Due Diligence for a large corporation in the context of a potential investment. As it’s an exercise I’ve never done before (at least not on that side of the table), I took on the opportunity, which eventually led to more missions in the same line. 

Organically, I also received requests to coach CTOs of Series A & B companies, which is something I felt comfortable giving a try at. During my time at Techstars, I invested in companies but more importantly, mentored them and coached the founders. 

Doing a lot of things at the same time has been an interesting journey and of course I sometimes felt confused, doubtful and even lost. But those feelings sometimes converge into breakthroughs. As Nietzche once said: “One must still have chaos in oneself to be able to give birth to a dancing star.”

I used my position as a CTO In Residence at Techstars as an experimentation playground to gauge the need for a dedicated CTO program. What I found was that it is not an easy task to design a program that interests a large population because of the discrepancies in skills and maturity levels in CTOs of early-stage companies. CTOs are also so heads-down into building things, that they hardly have any available moments, particularly if the topic seems remote to them.

My work as a Tech DD auditor has been quite enjoyable. I found myself to have a great ability to not only judge the technology of a company, but also the team, the product and how those 3 elements converge. The exercise can  sometimes be  mentally taxing, though, as I have to communicate with the CTOs about their shortcomings.

On top of that, my former MD colleagues at Techstars started to ask me about performing technical screenings of the companies applied for their respective accelerators; this experience sharpened my sense of raiting a company on both a technological and the team dynamics level.

Iterate, Try and Repeat to Find Your USP

My work with Techstars programs became focused on preparing companies for Tech DDs only. Although it may seem premature to prepare companies for an exercise they won’t be subjected to before a year down the road, my experience as an auditor also taught me that if you don’t prepare for a Tech DD at least a year in advance, you might end up with not-so nice surprises – namely, missing out on investment.

Technology Due Diligence are generally feared by CTOs for a few reasons:

– You don’t know what you don’t know
– There are not many resources out there to help you understand what you should be covering, besides the usual “5 things to think about for a Tech DD”
– You have the feeling that you might have neglected the things you ought to come back to (security, disaster recovery, etc…)
– It’s uncomfortable to be judged by an outside party while you’ve been hustling day and night to make the company work 2

When I was a CTO myself, and was subjected to a Tech DD, I felt ill-prepared. All I could do was hoping for the best. On the other hand, getting some external feedback has been key to improving the company, the team, and myself.

The reality is, Technology Due Diligence is nothing more than assessing the risk the investor or buyer is taking before conducting a transaction. This risk can be associated with how much tech debt the company has accrued, how much security is in place, and how ready is the company to scale and grow to the next phase. 

A tech DD is often the first external feedback a CTO gets about what he has built. It’s also the first time the CEO of the company receives an objective view  on what his team has accomplished. 

Failing a Tech DD is serious for several reasons:

  • You most likely won’t get funding for the next 6 to 12 months 
  • There are some serious concerns about what you’ve put in place
  • The rest of the company will lose some faith in you

Not only are you putting the company at risk of failing the investment, but you also know that your system is fragile – more fragile than what you thought.

I’m always transparent with the CTOs I’m auditing, because I believe they have the right to know what they lack and how to be better. One of the most common things I’ve heard is “I wish I would have known this a while ago. I would have had time to fix it.”

There is pain in there. And where there is pain, there is opportunity. 

Give Yourself a New Challenge Aligned With Your Core Beliefs

For the year to come, I’ve given myself a new challenge: helping as many CTOs as I can to build great companies using the Tech Due Diligence as a framework to identify gaps to be fixed. On top of that, I want to help CTOs connect better with each other, and give them a platform to ask for and offer help to one another.  

As a true entrepreneur, I’ll start small by continuing to test my core hypothesis (startups should be audited before they actually get audited), while refining and adjusting to reach a certain scalability.

Looking back, mapping out my skills/like/dislike/weaknesses checked quite some boxes. We’ll talk more specifically about the weaknesses in an upcoming post, so stay tuned!

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