Don’t Go It Alone: How to Fight Entrepreneurial Loneliness and Find Community

When I was in middle school, I started obsessively studying musical theater. I would go to the library and check out various cast albums, then make cassette tape recordings. Since I planned to go into the field, I was determined to study the genre and become an expert. It was a labor of (nerdy) love.

At that time in my life, none of my peers shared my bizarre interest, at least not to the degree that I did. But that changed when I got to high school…

I remember how it felt to find my friends in the high school musical and community theater group. I was not alone! There were other people who liked the same stuff that I did! They were not only willing to talk about it, but they LIKED talking about it!

I’ve had variations of this same experience over the years. For years, I obsessively studied fitness, but I didn’t have a social circle who shared my passions. I can remember when I finally pushed past my shyness at events and I started making friends in the industry. Once again… I was not alone! There were other people who liked the same stuff that I did!

Most recently, after several years of being business book junkies, Keeler (my biz partner) and I started actively making pals who ran businesses.

Entrepreneurship can be crazy-making and lonely. Every day you’re making lots of decisions and dealing with lots of uncertainty. You’re uniquely situated to see the big picture of your business, but no matter how hard you try, you’ll be making your decisions with imperfect knowledge. All the while your actions are being observed by your clients, your team, by other businesses, and if you get big enough, even the press.

This makes finding community all the more important for your mental well-being. Business owner friends can also provide great tactical advice and resources to grow your business. But most of all, by connecting with people who understand the challenges of entrepreneurship, you’ll feel a bit less like you’re eating crazy pills.

Here are four ways to find and develop community. More friendshipping, less loneliness!

1) Create A Peer Advisory Board

“Peer Advisory Board” sounds a bit formal, but it gets to the heart of this particular pillar. It can be incredibly valuable to have people you check in with on a regular basis to talk shop and share your wins, struggles, and learnings.

In my case, I have a few entrepreneur friends both inside and outside the fitness industry that I make a point to connect with on a regular basis. Although I’m usually not a phone person, most of these friends aren’t in NYC, so they often take the shape of 30 minute catch-up calls every two to three months.

While there’s nothing particularly novel about this idea, the difference maker is turning this into a system and doing it consistently. It’s pretty easy to let this slip off the radar, as we all have many demands on our time. But this is the classic example of a “non-urgent but important” task.

ACTION STEP: Pick three entrepreneur friends you’d like to connect with more frequently. Set up phone calls with each of them, and create a calendar reminder to reach out every three months.

2) “Never Eat Lunch Alone”

One of the best books ever written on networking is Keith Ferrazzi’s Never Eat Lunch Alone. While the book offers all sorts of useful strategies to build your network, I’ve found great value in taking the title relatively literally.

In a given work week, I have two to three lunches out with someone I want to spend time with. Sometimes it’s someone who’s reached out about getting together, and sometimes it’s someone I’ve contacted and would like to know better. Being in NYC, it’s not uncommon for this to be an out-of-town visitor.

Taking the time to break bread with people in a one-on-one setting is a great way to get to know people, reconnect, and deepen our relationship.

Admittedly, this particular approach is easiest when you live in a place like NYC. But even in smaller markets, you likely know other business owners you can invite to lunch to get to know them better. And if you don’t, it would be relatively easy to find them through groups like the Chamber of Commerce. In fact, part of the value of these lunch dates is that I often don’t know the person very well OR know much about their industry. So in addition to making a new friend, I get to learn about another industry or business structure.

ACTION STEP: Set aside one lunch per week to meet up with someone you want to know better, reconnect with, or deepen your relationship with.

3) Organize Gatherings, Cocktail Parties, or Dinners

If you live somewhere with a critical mass of like-minded people, you can also set-up gatherings, cocktail parties, or dinners. This is a great way to meet the friends of your friends.

This can be anything from a dinner party at a restaurant or in someone’s home, to inviting several people to meet out at a bar, to even hosting a gathering at someone’s office space. Since these events can feel like traditional (sort-of-weird) “networking” events, consider creating an informal structure for introductions and conversations. By softening the inherent social awkwardness with some ice-breakers or curated introductions, you’ll find people can connect more easily.

If you invite friendly people with similar interests, it’s not that hard to make these events “flow.” I’ve attended and organized lots of these events over the past few years, and I’ve never seen it devolve into old-timey, business card-swapping, traditional networking. While there’s nothing wrong with those kind of events per se, I personally prefer ones that plant the seeds for organic connections and new friendships.

ACTION STEP: Pick one night in the next three months to organize a dinner or social gathering of people you want to spend more time with and would benefit from knowing each other.

4) Join a Formal Professional Organization

One of the most important pillars in my professional community is the Entrepreneur’s Organization. It’s an international peer-to-peer network for business owners. In addition to hosting learning events with outside speakers, the heart of EO is something called “forum.” Each chapter subdivides the membership into small groups of 6-10 who meet on a monthly basis to talk confidentially about their “5%”; the most important things going on in their life personally and professionally.

The advantage of joining a professional organization is it provides a more specific structure for those involved. While I love the informality of the previous three options, professional organizations are effective BECAUSE they are formal. Most charge a monthly or yearly fee, the meetings are scheduled far in advance, and there are often requirements around attendance to maintain membership. Unlike the more informal options, this virtually guarantees developing deep relationships over time.

For some people, the best fit may be joining a coaching group that’s more exclusively focused on business and facilitated by a coach who helps members solve business challenges. Examples of groups like this include Vistage or Strategic Coach.

PLUG ALERT: Business for Unicorns offers an option called the Unicorn Society. In addition to having access to all of our courses, members meet once a week via Zoom, get unlimited access to coaching calls, and attend exclusive members-only meet-ups. (We’re currently at capacity and closed to new members, but will start taking applications in the fall. To learn more or join the waitlist, go HERE.)

Different professional groups will be more or less useful based on where you’re at in your life and your business. But virtually any entrepreneur benefits from having a formal group to meet with on a regular basis to share the triumphs and battles of running a business.

ACTION STEP: Look into various options for professional organizations that provide more formal structure.


Although I know it’s technically the topic of this article, the word “networking” is a bit scorched earth for me. Like the word “sales,” it’s been done so poorly and so often, it’s easy to forget that the highest integrity version of networking is really just “making friends.”

When I think back to finding my theater friends, my happiness (and relief) wasn’t because I thought they could further my high school acting career. And while I appreciated finding out about cool new musicals, it wasn’t that either.

Fact is, I had been lonely. Lonelier than I even knew.

Now it wasn’t like I had no friends, by any means. I just didn’t have friends that “got me” and deeply understood my dreams, my fears, and my drives. Once I had a community that cared about what mattered most to me, it changed the course of my life. And in very real ways, my adventures in the theater, and in fitness, and in business have all been dedicated to creating belonging. I think that intention has been at the heart of any success I’ve had.

And like the rest of life, intentions matter here. If you pursue the above strategies purely to grow your business and pile up contacts… you’re doing it wrong. Most humans can smell hidden agendas, so it won’t work.

But if you approach community-building with a desire to connect meaningfully with others, to learn from them, and to serve them, you’ll do more than grow your business. You’ll make lifelong friends who share your passions, support you when you’re down, and celebrate your wins.

And who knows? You might just find other people that know all the lyrics to Godspell. <3