Founding a Startup Remotely

Choosing cofounders, designing unstructured time, and planning our future hybrid model

I actually co-founded two startups in 2020…

In 2020, I decided it was a better time to found a startup than to move to the UK to go to graduate school (which I wrote about here). Like so many people in the world, our team would be working remotely. Much has been said about its pros and cons — but what would it be like to navigate the earliest days of a startup completely online?

After recently announcing our startup, Compa, I wanted to share what I’ve learned over the past few months for anyone considering founding a startup remotely. In short, it is absolutely possible with the right co-founders and collaboration design. At the same time, we are excited to shift to a hybrid work model in the near future.

Here is what we learned and what we expect next.

Our startup wasn’t born tinkering in a garage or Philz coffee shop, but in Zoom meetings and walking one-on-one calls.

So much for Silicon Valley nostalgia.

But the strength of our co-founder relationships made it possible, and exhilarating, to thrive in the early days.

The beginning is about resilience and agility. You need to persist through self-doubt and resist the inevitable feelings of imposter syndrome. You need to think clearly, but move quickly, and rapidly develop your ideas into testable hypotheses and place your next bets. Making this happen takes the right people at your side.

To found a startup remotely, you need to choose co-founders you already know and trust well.

Great co-founder relationships drive early startups forward. They generate energy to sustain you through the extreme uncertainty, and they elevate your work from transactional to truly creative. And for us, they alleviate Zoom fatigue.

Who doesn’t love a little 2x2?

This is true for remote workers in large companies, too, but acutely important for early-stage startups for two reasons. First, especially as a first-time founder, you don’t know how to do most of your job — you can’t simply go on autopilot with something familiar. Unstructured time together creates headspace to pull up and coax more creativity.

Second, you simply don’t work with as many people in an early-stage startup as you do in larger companies, so working remotely is that much more isolating. We’ve all learned to gather for morning coffees and afternoon drinks over Zoom; it’s just that much more important in a startup.

To collaborate online, we’ve relied on many of the familiar tools: Zoom for meetings, Slack for messaging, Google Workspace for productivity, Asana for project management, and Figma for prototyping, to name a few.

For unstructured time, we often turn off all these apps and do walking one-on-ones. When we want to brainstorm, we use MURAL, which is essentially a digital whiteboard where we can work together. Thankfully, my cofounder Taylor was familiar with it from his consulting work prior to Compa. MURAL has become instrumental to our startup team for virtual collaborative ideation.

We founded Compa in 2020; remote work is in our DNA. At the same time, we are very excited to shift to a hybrid of online and in-person work in the near future. Here are three hybrid work steps we plan to take for Compa.

First, we expect to offer access to office co-working space, but skip establishing a physical headquarters. HQs are expensive, limit talent pools, and can produce a haves / have-nots cultural divide between local and non-local employees. However, as the father of a 3-month-old, I would love to have the option to work in an office environment. We think decentralized co-working spaces combine the best of both worlds.

Second, we will recruit talent from anywhere, bounded by synchronous working hours. Gone are the days of hiring within a 50-mile radius of San Francisco, but we still need real-time collaboration. A “working hours HQ” during which everyone is online and available to meet for four hours within their local normal work day will enable us to develop a vastly larger and more diverse workforce spanning Honolulu to São Paulo.

Third, we will encourage in-person gathering several times per year when travel is safer. We still believe in the power of in-person time to connect and strengthen relationships.

I hope this is helpful for aspiring entrepreneurs and new startups navigating remote work. We are always looking for new ways to improve how we collaborate and build Compa into a lasting company.

We would love to hear what other startups are thinking about!

Co-founder & CEO, Compa | ex-Workday, Juniper, Mercer

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