Confessions of a Fearless Founder—From Crazy Bets to Safe Bets

Many Ventures, a Few Hits, One Slightly Bruised Ego

Apr 11, 2025

Founders and entrepreneurs are expected to be risk-takers. But actually, the best ones are risk-avoiders: they reduce risk whenever they can and only seek it when they can manage it. Here’s the story of where I went right—and wrong.

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I’ve started so many ventures that even LinkedIn doesn’t believe me anymore.

Safe bets never appealed to me.

I could have been an agile coach or consultant, raking in money during the golden years of agile frameworks and transformations. But I never wanted to. I often joked that I get bored working on other people’s problems. I have too many of my own that I find much more interesting.

In reality, I’m drawn to innovative ideas and the risk that comes with turning these ideas into successful business models. I can’t help it. Ever since I was fifteen years old and I tutored maths to other school kids or tried to sell cartoons to newspapers, I just had to do something valuable and try to get paid for it. And it was always creative or educational.

When my ideas don’t pay off, I get demotivated and I turn to something else that may get better traction. I’m not creative for the sake of being creative. I take the roads less traveled, and do the things other people don’t, just to see if I can make a difference. But I have bills to pay, just like anyone else. I’m a founder, not an artist.

Over the course of my life, I started more things than I can count. Some ideas were successful; others were not. I’m here to reflect and take you on a journey through the lessons learned as a fearless founder.

Print-on-Demand Before Print-on-Demand (1995-1998)

I’ll spare you the exciting details of my years as a software engineering student at the Delft University of Technology. Instead, the story begins after I graduated. I got involved in a training company that taught business people how to use computers and it didn’t take long before I was developing courseware materials on programming macros in Microsoft Word, Excel, and Access.

I quickly picked up on the signal that some customers were only interested in (for example) the merge feature of MS Word, the pivot table in MS Excel, and so on. I realized that what customers really wanted was courseware made specifically for their context.

So, I built a complicated system of hundreds of small Word documents that were automatically merged on the fly based on a selection mechanism in MS Access. Ten years before the technology for printing on demand (POD) became widely available, I was already generating courseware on demand (COD). The service became wildly successful and, because I had been smart enough to negotiate royalties on printed courseware with the training company, it generated a lot of revenue for me as well.

Ultimately, the venture developed into a unit focused primarily on building macros for customers. I managed it but didn’t own it, and so I lost interest and quit. I already had something else cooking.

Lessons learned:

Don’t wait for requests from customers. Act on signals in the market.
Always make sure you own a percentage of the value that you sell.

Metacritic Before Metacritic (1994-2001)

As I was programming and managing during the day, I spent my evenings curating content online. Noticing that people on the Internet were asking each other about their favorite computer games, I saw a need for a curated list: The Internet PC Games Top 100.

I developed a system that used votes from readers submitted via email and it parsed the mentions of games on Usenet groups, to arrive at a curated list of the best computer games on the planet. This weekly list became so popular that I started receiving free games and invitations from game studios in the US and I earned a significant income with sponsorship and advertising, years before ads on crowdsourced content became a standard business model.

The success culminated in an award as Entrepreneur of the Year in 1999 and a seed investment (that I didn’t really need) with the intention of hiring employees and scale up the concept to many more pop lists.

Alas, three months later, the Internet bubble burst. Advertising dried up, and I was left with a team and no revenue. No frantic amount of pivoting could save our little business from the inevitable conclusion that we had nothing to offer, but a simple automated tally of people’s opinions.

Lessons learned:

Awards mean nothing. Focus on trends, not on success.
Don’t take capital when you don’t need it. Bootstrap whenever possible.

Manager by Day, Blogger by Night (2002-2010)

Licking my financial wounds, and needing a break from the hectic days of managing a startup, I worked for nearly a decade as a development manager and CIO at a mid-sized company. And yet, I couldn’t resist acting like a founder.

As I introduced Scrum and agile principles in our teams, I noticed that hardly anyone in the agile community was talking about the role of team leads and development managers in agile organizations. I detected an unclaimed niche that I was well-positioned to serve. I’d been managing developers for ten years already and knew a thing or two about management! Obviously, some words of advice were needed.

The inevitable result was first a blog, then conference appearances, and finally a book: Management 3.0. And when the book approached its release date, I knew it was time to quit. I was a founder, not an employee. I needed to get back into the entrepreneurial field and be fully autonomous, responsible for my own successes and mistakes.

Lessons learned:

Full-time employees can still be founders by monitoring the market.
Employment only delays uncertainty. It never really solves it.

When Content Beats Coaching (2011-2017)

The success of the book led to a demand for courses and workshops. But from my earlier experiences in courses, I knew I enjoyed developing them much more than giving them. Also, content scales better than coaching.

So, I opted for a licensing model around my training when nobody else did that, at least not in the Agile industry, as far as I was aware. This approach allowed for scale and resulted in hundreds of facilitators worldwide offering the Management 3.0 classes. I was happy. My tools and exercises reached tens of thousands of people and many people have told me (until even this week) that I revolutionized their companies and, sometimes, even changed people’s lives.

However, after seven years, I got a little bored. Dealing with the daily issues of managing hundreds of trainers and business partners is not my strongest skill, and so I sold the company to other people, giving them a chance to scale it even further while I went back to tinkering with new ideas.

But that proved harder than I had hoped. You can hit a home run as soon as you get back onto the field. But don’t expect to repeat it in the next round, or any of the ten rounds after that.

Lessons learned:

Make any business model scalable. Sell your ideas, not your hours.
Know when it’s time to hand over the reins. Good founders can be terrible CEOs.

We Built an App. Nobody Cared. (2017-2019)

After Management 3.0, I had the idea for an app (Agility Scales) that would provide step-by-step guidance for coaches and managers dealing with team problems. The app was an example of a crazy bet. It required a significant investment in something that had only a slight chance of succeeding, which is why I needed external capital and I completed a successful crowdfunding round. If the app had succeeded, the return on investment could have been substantial, because of the scalability of the platform. But everyone knows that startups have a less than one-in-ten chance of pulling this off.

I assembled a team to get this idea off the ground. We talked with hundreds of customers, developed multiple MVPs, and attempted to do everything according to the books. We tried, against the odds, and we failed.

We couldn’t get the idea to work because users simply didn’t turn to an app on their smartphone to get help with fixed, predefined scenarios to address their team problems. They preferred to talk to each other, as they normally did, and the app gained no traction. This was six years before ChatGPT. We tried building an AI without the AI being available yet. Not my best decision.

Lessons learned:

Don’t make a product lacking a component that's crucial for the experience.
Don’t build technology as long as you don’t have problem-solution fit.

They Cared But Never Showed Up (2020)

During the Covid years, trying to recover from the previous setback, I came up with the idea to build a micro-learning environment. Instead of getting people to solve their problems with an app, I simply tried to motivate them to learn by reading articles, watching videos, and listening to podcasts. (We didn’t make any content because content was available for free everywhere.) The idea was to use gamification to help users gain the knowledge and insights that they would later apply whenever that came in handy.

I considered this a high-risk bet. Online learning had already established itself as a valid business model, but the gamified micro-learning idea was completely new. It was still risky enough that it needed validation, because much could still go wrong. But it was not as crazy as building our own app and content. We only built the gamified layer.

Again, I assembled a small team, and to my delight, the MVP that we whipped up in a matter of weeks (using only no-code platforms), got significantly more traction than the custom-built app I had tried to make before. This time, users were actually enthusiastic about the idea, and we even had a handful of paying customers, which quickly validated problem-solution fit: this was a problem worth solving! Sadly, that’s where we got stuck.

It turned out that setting aside time for micro-learning was the biggest obstacle for our users. People were paying for a service they believed they should use, but they weren’t actually using it because life always got in the way. It was like paying for a gym membership and never showing up. We were only successful at guilt-tripping users into a monthly subscription. This time, it was high churn and low retention that killed the concept.

Lessons learned:

Don’t offer a solution that doesn’t fit in people’s daily habits.
Don’t make people pay for something they want to use but aren’t using.

First Spasms of a Dying Industry (2021)

For a year or so, I experimented with new courseware materials (Shiftup) that were officially accredited by ICAgile. To be honest, I had a strong aversion to the self-accrediting institutes in the agile community offering inflated Agile and Scrum certificates, but I thought working with an independent organization was worth running an experiment.

In hindsight, this probably counted as a medium-risk bet (even though I counted it as low-risk at the time), because the agile market was already shifting. The demand for one-day and two-day agile workshops was perhaps not yet shrinking, but it was definitely also not growing. On top of that, I noticed that having to work according to the certification roadmap of another institute was like painting-by-numbers with someone else’s crayons. They set the direction, not me.

Lessons learned:

Stay tuned to the turning winds in a shifting market.
Don’t make your success dependent on that of another business.

A Comeback Cut Short by Reality (2022-2024)

Fortunately, good fortune returned to me with unFIX, the biggest success I’ve had since Management 3.0. After realizing that standard agile frameworks were on their way out, and that the agile community was looking for better ways of structuring their organizations, I came up with the unFIX model. The response to the early concept was nothing short of amazing. Invites for keynotes came in, requests for courses arrived. In terms of problem-solution fit, I finally hit a nerve.

Again, I assembled a team to scale this idea so we could reach more people. Here, I opted for a low-risk bet: I dusted off the licensing business model that had already proven its worth for Management 3.0, with some minor adjustments, and we got to work developing and selling courses with dozens of interested facilitators from around the world. Just as I had done with the Management 3.0 team a few years before.

For two years, this worked. Steadily, more partners joined and our revenues were going up, until it became clear that we could no longer ignore the inconvenient truth that had already been waving red flags at us from the very beginning.

The problem was that we operated squarely in the agile community and the “agile industrial complex” as a whole found itself in a state of slow but steady decline. There was plenty of interest in the unFIX pattern library, but it became increasingly hard to get paid for all the work we did. Our revenues were going up... until reality came knocking like a debt collector in a recession. Licensing two-day workshops in a dying industry was not my brightest move.

Lessons learned:

Take your time to craft a business model that works in the long term.
Do not quickly launch a good idea in a declining market.

Agile Is Undead. Long Live AI? (2025-?)

Not surprisingly, our company wasn’t the only one suffering from a bad business climate in the agile world. I talked with countless colleagues and found that many were in even more dire situations than we were. In particular, the large community of agile coaches and consultants (that I’ve never been part of but that I’ve always treated as valued business partners). Conferences got cancelled, meetups dried up, blogs and newsletters sat abandoned. The misery was obvious everywhere.

At some point, my former team at the Management 3.0 company reached out to us to see if there was a way we could join forces. When the market is bad, together you might stand stronger. And it made sense: leadership and organization design go hand in hand. So, for the last half year, our two teams had many discussions, and we decided to collaborate in a join venture, joining our brands under one banner: M3K.

M3K is a pivot to leadership in the age of AI, because there is no way back. The Management 3.0 company retains its focus on workshops and collocated events, while the unFIX Company will focus only on online learning. And that’s where we are now: while I’m advising the Management 3.0 team during their weekly meetings, and participating in M3K events whenever I can, my own focus is on a newly developed self-paced course and a soon-to-be-launched learning cohort.

But I’ll be honest: Online learning is a safe bet. Like buying canned food before the apocalypse. It won’t change the world, but at least it makes a difference. I will not pretend that e-learning content is a revolutionary concept. The e-learning market is already saturated as it is. To really make an impact instead of a difference, we’ll need grander ideas than this.

Lessons learned:

To be decided.

If you enjoy reading about my good and bad ideas, join me as I try not to kill the next one. Subscribe to The Maverick Mapmaker.

Uncertainty Everywhere

The world has never been more uncertain, for at least three reasons:

1️⃣ The agile industry has collapsed and nobody knows what happens next. Can the community revitalize? In these uncertain times, organizations need more help than ever, but will we still have meetups, conferences, and workshops? Do we need a global rebranding? How is technology going to change the organizational transformation itself? Nobody seems to know.

2️⃣ On top of that, artificial intelligence makes everything even fuzzier: will everyone be using AI agents soon or will they turn out to be a great disappointment? Are we going to see more middle management layers replaced by algorithms or will there be a backlash against digital bosses? Will we have AGI in a few years or is that still far beyond the horizon? The experts are happy to share their opinions, but their predictions are all over the map.

3️⃣ And the geopolitical situation doesn’t make things look any better. How can businesses plan for a future when they don’t even know if they will be hit with tariffs next week and what their supply chains are going to look like next month? How can we have a vision and develop a strategy on a game board that changes by the day at the whim of our political leaders?

What’s Next?

Only one in ten startups is highly successful. Two-thirds of them don’t even generate a positive return on investment. I’m not ashamed of not (yet) having hit another home run on my second, third, or fourth round. I count myself among the many. Investors that want certainty should sell lottery tickets, not buy them. There’s always demand for the promise of a rosy future.

Investors that want certainty should sell lottery tickets, not buy them. There’s always demand for the promise of a rosy future.

So, what am I doing now? I think, read, and talk with many people. I take my time creating situational awareness while I’m preparing for the most uncertain times I have ever encountered, and I advise everyone else to do the same.

I know one thing for sure: there are many people like me in need of a skeptical but optimistic take on the future, separating the hype from the doom. That’s why I started The Maverick Mapmaker newsletter on Substack. The best way to learn is to write about it, and I’m happy to take my readers for a ride.

In parallel, I enjoy diving deeper into the challenge of leadership in the age of AI and what happens after agile. My new book was a decent start—it has excellent reviews—and there’s a lot more to come, which is why I offer the self-paced learning course and the learning cohort under the M3K banner. At the very least, it prevents us from making stupid, risky decisions while we collaboratively learn about new opportunities in an age of high uncertainty.

I have plenty of ideas, but I’m waiting for the one that stands out and ticks all the boxes. As you've seen, my checklist of hard lessons has become quite extensive over the years. One thing is certain: I only do things that are creative and educational, because that’s just how I’m wired.

And when an exceptional idea does pop up, which is only a matter of time, it will be exciting to swing back onto the field in a fresh round. In the meantime, The unFIX company keeps a low profile, until some of the fog clears up and we come out well-prepared.

If there’s one thing I’ve learned, it’s this: The wiser I get as a founder, the more I understand about reducing risk or avoiding it altogether. Nothing is ever safe, but crazy bets are for crazy people.

P.S. If you know where things are headed, please share it in the comments. We’re all listening.

The Maverick Mapmaker (Agile, AI, Future of Work)

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