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Money matters; mentorship matters more

January 26, 2022 · 3 min read

Today, the team and I are excited to announce Air's $10M Operator Round, valuing the company at $110M

There’s never been a better time to be an entrepreneur. Capital is cheap and investors come in all shapes and sizes. When we started Air in 2017, I thought a nine-figure valuation would be a significant milestone. Now, I’m honestly wondering if I’m caught behind. This isn’t the biggest round at the highest valuation, but it is a foundational statement about how we think about this journey: we believe there will always be the next lesson. That’s why we’re bringing on 100+ strategic operators to help accelerate our education. It’s their feedback and perspective that is pushing us forward.

We’re not the best (yet).

The “hire the best people” adage has never sat with me well. I’m not the smartest person in the room and I’m most definitely not the best CEO. However, I hope one takeaway is clear to those I work with: I’m hypercritical of my output and I try to get better every day. At Air, we try to find smart people who are curious and want to grow with us. They come from a variety of backgrounds, they love documentation, and they obsess about feedback. Each of us is here because we have more to prove and we love the problem we’ve set out to solve.

We’re building this product alongside industry mentors.

Operator Rounds have been on the rise because community participation can provide go-to-market acceleration. This kind of vocational training is a return to the foundations of entrepreneurship. There is procedural knowledge in each industry, and these insights are at the core of building a real solution for the market. Many of our operators are current (or future) customers. They’re pushing our roadmap, providing cautionary tales of the challenges ahead, and introducing our product into our category in ways that feel organic.

Their perspective fills the gaps in our experience.

Our leadership team (Tyler, Dio, Heather, Subu, Carmi, Ben) is filled with folks who excel in studying and teaching their craft. But it’s important to be honest about the fact that we’ve never done this before. While each of us has found success at various stages of our careers, we’ve never led and scaled a high-velocity business at this stage. The mentorship we receive from these operators allows us to be vulnerable. Many are industry veterans leading aspirational companies. They live in the problems we face. Their mentorship will be critical in helping us grow—and grow up—fast.

Just watch, we’re going to win our way.

My goal is to prove that we can build a world class business on pillars that are antithetical to Silicon Valley tropes and start-up cliches. We’re not hiring the best people, we’re hiring the right people. We don’t know everything, but we’re closing the gap every day. Our market opportunity is massive, but I’ve made it through this entire announcement without making a pitch. The journey we’re going through and the people that we’re sharing it with will always be the most important thing you need to know about Air. We’ve built this company, this product, and this business with intention. That’s why we’re going to win and, if you stay tuned, I’ll prove it to you.

Always on Air,


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