Closing our First Deal - A Retro

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Published
May 10, 2025

Last week, we hit a major milestone, our very first paying customer! Though it’s exciting, I wanted to spend this week to pause and reflect on what worked, and what didn’t.

What Worked

  1. Leverage Warm Connections
  2. Your network is one of your X-factors. One warm introduction can open doors that may take months or years to build otherwise.

  3. Deeply Understand Your ICP, Incentive structure, and Cash flow
  4. Map out your ICPs incentive structure, their customers, stakeholders, and any other entity involved in cash flow. Opportunities often hide in the misalignments between stakeholders - focus your efforts there.

  5. Solve Any Problem, Prove Value, Build Trust
  6. Get your foot in the door by addressing a tangible pain point - even if it’s not the one you’ll ultimately monetize. Early on, it’s more important to earn trust and visibility into workflows than to obsess over revenue per user.

  7. Set a Target ARPU
  8. That being said, define your Target ARPU. Identify monetization strategies that can lead you to your target ARPU and quickly validate. If you can’t validate then pivot quickly.

  9. Validate Quickly
  10. Whether it’s a prototype, a manual process, or customer interviews - write down every hypothesis and validate as cheaply as possible. The faster you learn, the faster you iterate. Every conversation you have should answer a hypothesis

What Didn’t Work

  1. Targeting the Wrong Market
  2. The right market is one that plays to your strengths. Don’t pick a market that isn’t a good fit.

  3. Choosing the Wrong Customer
  4. Low-margin customers or tiny TAMs make it impossible to scale. Aim for partners whose success rides on your solution.

  5. Taking Customer Feedback at Face Value
  6. Users rarely surface their true, critical problems if you ask them directly - they’ve usually built workarounds for those already and accepted them as necessary evils. It’s your job to listen to them and pull the thread.

  7. Avoid “I know better mentality”
  8. Even if you do know how to do marketing better than your client ever could, they’re the ones that you have to convince. Convince through real results. Solve one of their pain points and prove your value to earn credibility

  9. Validation through Building
  10. It’s tempting to write code or build a Figma to show to your customers. Ask yourself if it’s really necessary and if there’s any other way to validate. Building is automation and takes resources. You would never pay to build a factory that manufactures cars unless you had strong conviction people would buy.

Conclusion

  • Talk to real people. Real people have real problems. And talking to real people gives you a data moat that others don’t have.
  • Be disciplined on what you’re looking for. Hyper focus on what signal you need to green light and accelerate.
  • Validate as fast as you can. That usually means not building. Instead just get on calls with people.

It’s been an exciting journey so far. Here’s to the next milestone!