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How snowboarding resembles venture building and entrepreneurship - Product Market Fit edition

I remember a day when I was launching everything commercial for a new corporate venture alongside our CTO, who handled all product and technical aspects. In those early days, we faced a significant issue with onboarding. Some prospective customers couldn't complete the final step of our lengthy conversion journey. The brass was worried and demanded a swift solution. I hate to admit it, but I was anxious too.

Then our CTO said something I'll never forget:

"Our customers are onboarded once in their lifetime, but use our product multiple times daily throughout their relationship with us. We have more pressing issues.

I didn't fully grasp what he meant at the time. It seemed logical that if customers couldn't get through the door, they wouldn't be able to enjoy what was inside. What I missed was crucial: more than 50% of customers were getting in. It was more important to retain them, understand their needs, and give them reasons to stay before focusing on bringing more people through.

My CTO had vastly more experience building products from the ground up. Since then, I've watched countless founders fall into the trap of optimizing for the wrong dynamics at the wrong time.

I often say, "launching a startup or any new venture is counter-intuitive." It's like snowboarding. When skiing, you face downhill and go downhill. When snowboarding, you're going downhill but occasionally facing downhill, uphill, or sideways. You do what needs to be done in the moment, often against common judgment.


Looking at the customer journey:

  • They decide to become a customer - Acquisition

  • They complete the steps to become a customer - Activation

  • They continue being your customer - Retention


The end result—what we do everything for—is growth. But should a venture builder focus on growth? Absolutely not, unless they've mastered Retention first, then Activation, then Acquisition. Only then is it time to focus on growth. And you can do so after reading this.


Of course, you need a bare-minimum flow for acquisition and activation at launch, but that's it. Minimal growth efforts are all that's needed initially.

It's counter-intuitive. You're not following the customer journey; you're reverse engineering it:

  • Build a bare-bones system for bringing in your first batch of customers - MVP

  • Ensure those customers receive what they need and stay - Retention

  • Make sure customers start receiving value as soon and as seamlessly as possible - Activation

  • Ensure more customers who are likely to stay find their way to your door - Acquisition

  • Optimize for repetition - Growth


Diagram showing the customer journey and the founders journey to product market fit
How the way founders follow the customer journey in reverse order when prioritizing for product market fit

Retention hints at product-market fit more than anything else. Spend your finite and precious resources (time being the most valuable) on what matters most. You'll eventually address the other areas.


Define a quantifiable behavioral metric for whatever you're focusing on. This is sometimes called the One Metric That Matters (OMTM) or Metric That Matters Most (MTMM). This focus will change over time. You'll notice that optimizing a particular metric eventually yields diminishing returns. That's when you move on. By all means track many metrics, but optimize one at a time, sequentially.

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