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More on Radical Experimentation

This is the second part of my Radical Experimentation article which I encourage you to read first if you rudely haven’t.

In this article I will cover 4 additional radical areas for experimentation, and cover the pitfalls of experimentation you want to watch out for.

Your Roadmap is a Road of Experiments

Worse than being wrong is being wrong and not knowing why.

Product leaders have long adopted an experimental mindset, but many still treat their roadmap as an absolute truth. This is dangerous.

A roadmap is nothing more than a series of horrible, amazing, and mediocre guesses. The only way to tell which one is which is to test them against reality. Each one of these guesses is, you’ve guessed it, an experiment.

How does an experimental mindset help when it comes to roadmaps?

  • Forces everyone to be open to learning and testing the truth, instead of instantly falling in love with everything you build

  • Things are magically scoped smaller and built faster, because your goal is not to build, it is to learn and validate

  • Your roadmap and product adapt to reflect reality, resulting in a better, more valuable product

I once tried guessing which items on our roadmap would succeed and which ones would flop. My guess turned out worse than flipping a coin. If you’re not convinced that your roadmap is just a series of guesses, try this yourself.


Worse than a bad customer is an annoying bad customer.

The typical intuition with customers is to do whatever it takes to make them happy.

This intuition is wrong because some customers will help you reach your goals while others will distract you. Telling which one is which is hard, which is why you should first focus on identifying what a good customer is and only then on making those good customers happy (or more precisely, making them successful, as my VP of customer success likes to say).

How does an experimental mindset help with customers?

  • Helps you focus on identifying the ideal customer at all costs, instead of making bad customers happy at a great cost

  • Gives you permission to depart from bad customers. Then when your customers are cohesive and are marching with you in one direction you climb product-market fit mountain faster

  • By not fighting for bad customers, you save time and pain for both sides

In the early days of my startup we had too many types of customers. Our customer success team worked really hard to make every customer happy and renew, and did so amazingly. But in retrospect this worked against us. It blinded us from the fact that we didn’t have product-market fit and that the value we were providing was basically consulting. It would’ve been better to lose these customers and face reality sooner.

Keep your love for those who can love you back.


Worse than fundraising is… wait, nothing is worse than fundraising.

People like to go into fundraising only when they are super confident, polished, and opinionated about everything. You spend months perfecting your pitch, collecting every piece of data, prioritizing investors, and months later hit the road to find out that nothing is clicking.

Early stage funding is simply unpredictable, which is why you need to think about it as an experiment.

How does an experimental mindset help with fundraising?

  • Forces you to test the market and your story all the time. Instead of wasting months perfecting something that wouldn’t work

  • Removes your emotions from the process. Because fundraising is so critical and stressful, this is exactly the place where you want to be less emotional

  • Makes you more flexible and open to feedback. Contrary to common wisdom, being overly confident and opinionated about everything does not lead to better fundraising results

In one of my fundraising experiences we went to the market too early and very confident. We spent a lot of time preparing, many months pitching, and anxiety was pretty high as well. The signs that we were too early were there, but our overconfidence blinded us from reality.


Worse than a bad leader is a bad leader that doesn’t see it.

Yesterday you were building the product alone, today you’re selling it, tomorrow you’ll be scaling the organization. Your role as a leader changes constantly and you can’t predict what you’ll be good at, what you’ll be bad at, and at what point you will no longer be relevant.

How does an experimental mindset help you see yourself better?

  • Reduces your ego. The organization comes first because you constantly test your contribution against what the company needs

  • Allows you to evolve your role based on what is good for both you and the company, and not based on a title from 4 years ago

  • Creates a culture where the right people and positions change based on circumstances and contribution, not momentum and status quo

My personal example is leading our product. In the early days I had to painstakingly accept that my role was product management and not writing code, then I had to realize that I needed to hire someone to supplement my remarkable product deficiencies, and finally to give product ownership to that person who was simply better than me. Every step in this process was slow and not easy. Had I thought of my evolving role as an experiment, it would’ve been quicker, easier, and better for the company.

I will work hard to continue scaling as a CTO and leader, but I will let the experiments, not my ego, indicate when it’s time to step aside.

A Word of Caution

Every powerful tool can backfire. As you adopt radical experimentation in new areas you should be aware of 4 common pitfalls.

Subjectivity. Some areas are inherently subjective. Whether it’s the vision you have for your company, the culture you want to build, or your personal values. You should definitely evolve and refine those, but don’t question their validity every morning.

Commitment. The worst outcome for a failed experiment is not knowing whether the guess was wrong or if the execution was bad. You must fully commit to an experiment to eliminate the latter as a possibility. And yes, this means that experiments require focus and therefore need to be prioritized.

Timelines. Experiments need to be as short as possible and not shorter than that. You don’t want to quit your startup the first time you discover you were wrong or fire an employee the first time they screw up. Think about the timeline in advance and write them down.

People. People generally don’t enjoy the idea of being the subjects of experimentation. Be careful and always put empathy first and the experiment second.


When I’m able to fully embrace the experimental mindset I experience startup transcendence. It allows me to step out of a situation to see the full picture, face reality, and leave my emotions and biases aside. Ultimately, it makes me less wrong and more calm.

The experimental mindset is simple. You make a guess, you predict the future based on this guess, and you experiment to compare your prediction against reality. The hard part is doing this in radical areas.

We’ve covered a few radical areas where this mindset is extremely powerful. Your startup, new hires, goals, roadmaps, customers, fundraising, and you yourself should all be treated as experiments.

This is truly just the tip of the iceberg. This mindset is relevant everywhere, and well beyond the confinements of your startup.

What radical experiment should you be running right now?


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