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Entrepreneurship for Engineers: Founders Need Community, too

Running a startup can be lonely. A group of peers can help you commiserate, celebrate and gain a more realistic sense of how you’re doing.
Sep 3rd, 2022 5:08am by
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Entrepreneurship for Engineers is a monthly column by longtime New Stack contributor Emily Omier that explores the concerns of developers who want to build tools for other developers — and build a business around their innovations. We welcome your feedback, and ideas for future columns.

I’ve been writing this column for over a year, which means I’ve had time to recognize patterns in conversations with founders, investors and advisers. One of those themes is that founding a company can be a lonely road — one that is less lonely with co-founders, but can be lonely even with others to walk the path with.

One way to combat loneliness is with community — and as it turns out, the benefits of being part of a community of founders go far beyond feeling less alone.

“My journey as a founder, as a CEO, as an entrepreneur would have been so much easier, faster and better had there been something like Heavybit,” said Jesse Robbins, founder of Chef and now an investor with community-focused Heavybit, which invests in developer tools companies and provides ample opportunities for founders to interact with each other.

The mental health benefits of being around other founders who are either going through the same process as you are, or have been there, are important and should absolutely not be discounted. However, it would also be a mistake to think that the only reason to connect with other founders, from those ahead of you on the entrepreneurial path to those far behind and everyone in between, has to do with mindset or sanity.

“Most of the secrets to building a company, let alone a successful one, are actual secrets,” Robbins said. “You can’t really write a book and describe every single specific set of challenges.”

Sharing Common Pain Points

As a founder, putting yourself in environments where you’ll be able to brush shoulders not just with one or two mentors but with a wide variety of entrepreneurs, all at different stages, increases the chances that you’ll find someone who’s encountered a challenge similar to what you’re facing now. It also helps to connect with other technical founders, specifically, who are most likely to experience the same pains that you are.

“The pain points are almost always about the differences between building an engineering organization that builds products, versus building a company that sells products and that supports customers and builds movements out of communities,” Robbins said.

Hearing from other founders about how, for example, they overcame an initial aversion to hiring a first salesperson or building a marketing organization can help founders make the transition from engineering leader to CEO faster, and take the steps they need to ensure the business thrives, even if that means letting go of the dream of building a company without a sales team.

Heavybit organizes events specifically to bring together technical founders and build community among them. At those events, you will frequently see two founders peeling off from the other group, having a private conversation, Robbins said: “And what goes on in those conversations can change the trajectory of a company.”

Peter Pezaris, four-time entrepreneur currently senior vice president of strategy and experience at New Relic, pointed to another advantage a community brings.

“When you’re a founder, you have no idea. Your revenue might be growing by 10% per month, but is that good?” he said.

There aren’t always clear benchmarks to understand whether or not your young company’s performance, or your personal performance as CEO, is successful. A community of other founders gives you a way to compare yourself and your company to your peers.

There are a lot of very high highs to founding and running a company, and it can be hard for those who haven’t been there to relate to them and truly celebrate with you. That goes back to the mental health benefits of community for founders, which might be harder to connect to ROI but are critical nonetheless.

These are the advantages of community when times are good; when you’re struggling, commiserating with your fellow founders can be helpful. “I don’t know that I’ve ever met a founder that hasn’t gone through some bad times,” Pezaris said. “And in those times, it’s hard for anybody who’s not a founder to really understand what you’re going through.”

Finding a Community

So how do you cultivate a community of founders?

If you don’t already have access to a community of founders, how do you find one or build on yourself? What do you look for in a community? Here are some things to consider.

Who is in the room? In a community of founders, it’s safe to expect that there will be other founders. But should investors be present? And how should you decide who should or should not be in the room?

“The only way that you can really have a true community is to provide spaces that are facilitated, and that every participant feels and actually is safe,” Robbins said.

If there are investors present, they have to be investors who you can truly share both good and bad news with. You wouldn’t want any toxic or untrustworthy founders to be part of the group, either.

Virtual or in person? Meeting virtually certainly reduces the friction, but it can also make it harder for the one-on-one, private conversations between founders that can be so powerful.

There are also more risks to confidentiality in a virtual setting — it’s so easy to screenshot a Slack room, and some of the things you would want to discuss in a founder community could be damaging if they’re widely shared.

Startup incubators like Y Combinator are one place to find community; others include venture capital firm events like those run by HeavyBit and other investors. Entrepreneurs’ Organization is another place to find community, though it’s less focused on technical startups.

“If you are a founder who doesn’t have the support system that you would like to have, and you recognize this as an issue, seek it out,” Pezaris said. “I’ve found pretty consistently among founders that if two founders meet, it’s really often that they want to try to help each other.”

Do you have any topics related to entrepreneurship you’d love to see covered? Reach out on Twitter and let me know.

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