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(Long-term) greed is good: A $100 million founder’s 4-point plan for building a unicorn in 24 months

May 03, 2022 · 4 min read

Written by Shane Hegde, Co-founder & CEO

We weren't the fastest company to $100M, but our next two years will prove that we approached the first four the right way.

At Air, the cloud collaboration tool I founded with my college roommate, Tyler Strand, we believe it pays to be long-term greedy. In practice, this means we aren’t always – or even often – after the quick fix. What we are doing is holding true to our values, even when things look like they might go off the rails. Especially then.

We launched Air on February 28, 2020, three days after the CDC announced that COVID-19 was heading toward pandemic status. There’s no playbook for launching a start-up during a pandemic. We kicked off fundraising during quarantine with four months of runway to raise capital amidst a global recession. It took us 42 days of nonstop work to arrive at a term sheet. In that time period, we had to lay off 16% of our staff and move out of our office to conserve cash. We passed on taking a PPP loan because it felt wrong. We took 136 meetings with 57 firms. Our "data room" was a 7,000 word Notion doc.

Two years later, our valuation stands at $110m, with a recent raise bringing us to $28m in funding. We’ve quadrupled our team - and are growing fast. In addition to paying customers including Google, Duke Men’s Basketball and The Infatuation, tens of thousands of users enjoy Air's free product, which manages almost 20 million assets. Customer revenue doubles every six months. 

It wasn’t easy to get here but throughout we were guided by this “greed” to ensure the business - and how we conducted ourselves - was something we could be proud of. We are trying to build a great business with strong fundamentals. We’re urgent, but are always trying to play the long game. 

Throughout this process, there are four key things I’ve learned that have proven essential to our success.

1. Fortify your base

Take the long road to make sure you have strong business fundamentals. 

Over the first four years, 80% of every dollar spent went to product development. We thought about the capital allocation as direct investments into retention, engagement, and expansion. It required us to be extraordinarily methodical: We ran a six-month long pilot program with 20 partners, meeting on a biweekly basis at their offices to figure out where our gaps were. We launched a waitlist as offices shut down in 2020 to bring in new customers and see what breaks. A lot of things broke. It took 18 months to refine the first-time experience to give us the confidence to launch a free tier in March 2021. But it paid off: a 98% monthly retention rate and 95% organic growth carried us forward with a quarter of customers using Air every day during the work week. 

With a strong foundation and a bucket that doesn’t leak, you can enter the growth stage with confidence and conviction.

2. Hire leadership strategically

Give away functions of the business when they have a direction – not before. 

Founders don’t scale, but if you are going to add seasoned leadership to the team, only do so after you’ve done the work of learning what you really want – and need – from that side of the business. Take the first risk. My co-founder and I have never hired an executive for a role that we did not previously cover. Spending a week or a year in a given task allows you to build an appreciation and understanding of the work that is incomparable. It also forces you to evaluate quality and direction and choose a path. This path will lead you to a candidate with the ideal experience to carry the track of work forward. 

3. Obsess over documentation

If you work remote and asynchronous your processes and tools need to be remote and asynchronous.

From my perspective, the only way to run a scalable, global, remote team is with robust documentation and overwhelming amounts of transparency. Ephemeral messaging tools like Slack are crucial for collaboration, but they cannot carry business processes forward. 

Business decisions should not be driven by a timeline but a process, and a process is held within a document. An obsession with documentation enables our organization to scale quickly, and ensures that new hires can step into our business and onboard in days, not weeks.

4. Deploy cash to solve scale and time to solve stage 

Use human intervention to solve gaps in your product or customer experience, and reserve investment dollars for moments of acceleration when you’ve figured things out. 

Agencies don’t solve problems, they build perspective and guide you to a solution. New hires should walk into a role, not a problem. You can’t invest everywhere and you need to make financial decisions that are not easy to unwind. Your time for grit and creativity can allow you to fill the gaps in any experience. Remember that you’re David, not Goliath. And the sacrifice of your time can be worth it so that others or your dollars can be focused on a core problem at hand. 

There’s so much power in living in the problem. I promise it will guide you toward the best solution for your business.

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