Customer Development Upstartist Diaries

Daring to Suck is the Quickest Way to Learn

So why not make it fun, expected and social with “challenge masterminds?”

1. The Dare to Suck Challenge

“Thank you for organizing this challenge. I learned a ton.”

It meant a lot to hear this from Matt. We had just finished our final Mastermind call. Over the past four weeks we had Zoomed twice a week with the goal to test one business idea a week. It didn’t matter if we asked for customer commitment through an email, website or Amazon listing, just that we asked.

We called it The Dare to Suck Challenge, based on legendary rock band Aerosmith’s weekly “dare to suck” jam sessions.

Singer Steven Tyler described how the band makes music: “Each one of us brings an idea that we think is probably terrible, and that we are embarrassed that we even have the idea. But we present it. And nine times out of ten, the idea is actually terrible. But one time out of ten you get Dude Looks Like a Lady.”

Matt and I each dared to test four business ideas, no matter how terrible, and while none took off, we grew our skills, knowledge and courage to try.

I’ve found that deliverable-based challenges, done with a group of well chosen peers, are the fastest way to build know-how, products and relationships as a solopreneur. 

2. Pottery School

Quarantined during Covid-19, I took many online classes. My favorite was Game Design & Theory, taught by Will Wright, creator of The Sims.

If stuck on a design choice, his team would watch players interact with different versions of the game to see what mattered. Why had I not done this more with my business?

Through the Will’s class I found Rami Ismael’s post on making one video game a week to get experienced at failure.

Rami shares the story of a pottery school. One group of students was told to make a vase by the end of the semester. The other group was told to build one vase per week and destroy it. Guess which group ultimately built better vases?

Inspired, I designed our own weekly challenge. Instead of making one video game a week, we would test one business idea a week. The goal? To be like that second group of pottery students. After four weeks, would our ability to test business ideas improve?

I approached five friends, all experienced entrepreneurs, to join me. Two said “yes.”

Then I asked them for $50. If they completed the challenge they’d get their money back. Skin in the game.

It was time for our first call.

3. What is a Mastermind?

Matt and Kenny had never been in a mastermind so I gave them some background. Coined by Napoleon Hill in 1924, a mastermind is a small group of peers that gathers regularly to share problems, get support and learn from each other. Think of it like having a board of peer advisors.

Groups like Entrepreneurs Organization have been built around this format. When I started Touch MBA, I joined a mastermind to learn from more experienced entrepreneurs and keep myself accountable – hard to do when you’re your own boss.

The rules for this Dare to Suck Mastermind Challenge were:

  • Meet twice a week for 60-90 minutes
  • Test one business idea per week, or the others split your $50
  • Complete confidentiality

We introduced ourselves, shared ideas, and left eager to start. We had four days to make our first prototypes.

MVP stands for minimum viable product, start-up jargon for testing the first version of your product with customers

4. Speak Less, Learn More

Matt and I met for session two to get feedback on our prototypes.

Mine was a series of emails, his a series of product images.

(I can’t share our ideas because of our confidentiality rule, remember?)

To get user feedback, we borrowed exercises from Sprint: Solve Big Problems and Test New Ideas in Just Five Days, written by Jake Knapp, who created the sprint design process for Google Ventures.

  • Have the user speak about prototype. What are they thinking and feeling?
  • Ask open ended questions to probe deeper such as “Why do you think that?” and “What else could you tell me about that?”
  • Focus on surprising details and patterns from your users. What can you improve?

(Obviously it would have helped to have more than one user – although interestingly, the Google Ventures design team found that 85% of problems were observed after just 5 people were interviewed)

After doing this four times with four different prototypes, I learned to show Matt my prototype and shut up. The less I talked, the more I learned about his daily problems, worldview and experience with similar products or services. The more concrete my prototype, the more insights I gained.

For example, instead of droning on about why or how I designed my product, I’d just let Matt interact with it. What was his first impression? How did he talk about it? What questions did he have? Based on his comments I’d dive deeper. I didn’t always hear what I wanted to, but got a much clearer picture of what could be improved from a customer’s point of view.

5. Life Happens

Kenny didn’t show for session two. 

His wife Sheila was in labor. I couldn’t imagine going to a hospital in New York City, then the epicenter of Covid-19, and giving birth. Now Kenny and Sheila have a beautiful baby boy. But Kenny was out for the rest of the Mastermind. 

6. Courage

Session 3 was about sharing the first products we had launched. I had gotten two customer commitments, Matt none yet.

We learned that fear (often disguised as perfectionism) is the enemy of launching, and therefore learning.

“If you are not embarrassed by the first version of your product, you’ve launched too late.”

Reid Hoffman, Founder of LinkedIn

We were both embarrassed, but at least we had launched. 

Asking for commitment from customers requires courage, because your fragile ego is exposed.

What if they don’t buy? What will they think?

Testing ideas is like doing stand up comedy. You feel naked on stage, and the silence can be deafening. But it’s thrilling to get a laugh. Even if you bomb, you’ve learned something for next time.

7. The Mom Test

Our weekly meetings continued. Week 2. Week 3. Week 4.

Each Thursday we got better at prototyping, asking the right questions, and listening for insights. Each Monday we grew thicker skin to ask for real customer commitment.

Matt taught me to focus on the existing market. What was selling and why? What could be learned from customer reviews?

I also discovered a gem of a book on customer development: The Mom Test.

The big idea? Don’t talk about your product. Instead seek concrete details about your customers’ behavior and worldview. You should never ask anyone – especially your mom – whether your business is a good idea.

The best way to test your idea is not to ask, “Would you buy this?” but rather to present your solution and ask for a commitment of time, reputation or money.  Getting one paying customer is much more telling than getting 100 or 1,000 likes.

Another takeaway from the book is that you can stress test business ideas anywhere. Ask about other’s problems. People like talking about themselves anyways.

8. Why Masterminds Work

Matt and I pushed each other. We didn’t want to show up empty handed. Matt’s time was precious. Do you know rare it is to have someone’s undivided attention for 30 minutes to talk about your product?

I made sure my prototypes were detailed enough to have a productive discussion.

Matt took full advantage of my time too.

We could share openly and directly without risk, unlike with a boss, employee or customer. That’s the best part of peer feedback – often times a stranger with nothing at stake can provide insights or perspectives that never crossed your mind.

9. Takeaways

We didn’t even realize we had completed the challenge.

“So what’s the plan this week?” Matt asked.

We were so used to the rhythm of prototyping, iterating, and launching.

In fact, after I gave Matt my thoughts on his fourth and final product, he corrected me: “I could do that, but it doesn’t test commitment from my customers.”

Music to my ears. We had graduated. 

We shared our biggest takeaways from the challenge.


  1. How quickly you can make something with a deadline
  2. How much you can learn from experienced peers
  3. How complicated it is to launch products on Amazon


  1. How peer pressure keeps you accountable
  2. How I learned much more from doing than reading
  3. How crucial it is to stress test assumptions about your idea asap

10. Ship Fast, Learn Fast

I want to share some thoughts on building skills as a solopreneur. 

After 10 years of consuming hundreds of books, podcasts and courses, I believe the focus needs to be on shipping something by a certain deadline. That is how I’ve learned the most.

Silicon Valley tech startups live by the mantra “fail fast, and fail often.” But this leaves out the purpose of failing fast: to learn faster. If you’re failing and not learning anything, failing fast is disastrous.

I get the essence of “failing fast” though. The most important insights for your business aren’t found in books, courses, and case studies, but through the real, often brutal collisions of your product with customers.

“Everyone has a plan until they get punched in the face.”

– Mike Tyson

Last Sunday my friends and I played the popular board game Settlers of Catan. I had played a few times before and our games would last 3 hours. This time my friends had to leave early, so we decided to do a speed round. We’d play to 7 points (not 10 points), limit our turns to 1 minute (instead of unlimited time), and conclude the game, no matter what, by 11:00pm. 

Playing fast accelerated my learning curve. I didn’t have time to deliberate on the absolute best move. I just had to go – and deal with the results. Did I make dumb mistakes and lose? Yes. But I learned the essential strategies of the game much quicker.

Imagine if I had played 10 speed rounds instead of those 3 super long games? My mastery of the Catan would be light-years ahead.

What gets you to ship fast so you learn faster?

For me, deliverable-based challenges – done with experienced peers – have been the best way to learn new skills, identify blind spots, and grow my business. 

Are “Challenge Masterminds” the Best Learning Format for Solopreneurs?

Solopreneurs face unique learning challenges. We’re less concerned with certifications – and the signal they provide to employers – than growing our ability to market and add value asap. Most of us work alone, and with less resources too.

So I believe learning with a group of practitioners and on projects that could immediately serve our businesses is the best way to learn.

Books and podcasts are too often consumed passively.

Online courses have a completion rate of 10%.

Conferences inspire and connect but lack follow up.

And traditional degrees are often too long or expensive.

Challenge masterminds combine the best of all formats. They force action – and real output – with peer accountability. They provide a fun, safe space where we can dare to suck and learn faster – and from each other’s mistakes too. And intimate, regular gatherings help us deepen relationships, build our networks, and gain new perspectives.

Today we can access lifetimes of knowledge with a few clicks. What’s lacking is daring to suck, regular practice, and safe spaces to share, learn, and connect.

Want to join our next challenge? Sign up here.

Photo by Quino Al on Unsplash

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