How To Meet and Connect With Other Entrepreneurs

Sometimes wine helps :)

Sometimes wine helps :)

How To Meet and Connect With Other Entrepreneurs

I’ve been an entrepreneur for a looong time. 22+ years in fact. So long that I can’t possibly imagine any other way of being, and I hope I never have to.

I’ve gotten used to the freedom of being an entrepreneur, and calling my own shots and setting my own schedule. I’ve also had to get used to a lot of hardship along the way. Much of that hardship was self-imposed because of my own isolation.

It’s easy, when you’re an entrepreneur, to become pretty isolated, especially when you’re struggling.

When you’re struggling, it’s often hard to find people to talk to, or people you’re comfortable talking with:

  • You don’t want your staff to know you’re struggling (or the business is struggling)

  • If you have investors, you definitely don’t want them to feel their investment is in jeopardy

  • Talking about your struggles with your partner might open up a lot of feelings of shame

  • Your friends (who may not be entrepreneurs) might not relate to what you’re going through

Like many (most?) entrepreneurs, I experienced all of these feelings when I was at my worst. And I made my difficulties even more difficult by truly isolating myself and not reaching out to others (I didn’t feel I had anyone to turn to).

In 2015/2016, as my former business (which I exited in February of this year) was getting bigger and more complex, and I was having a hard time with it all, I finally started to end my isolation and started to reach out and connect with other entrepreneurs.

That was the start of what is now a lifetime journey to build community in the entrepreneurial world - first for myself but now also for others.

Building those connections has been, to use an overworn cliché, a gamechanger. I’ve experienced more success in the past 2 years than the 20 previous, and almost all of it can be attributed to the amazing network of people I’ve built relationships with over this time, among whom I count both business associates and close friends, and everything in between.

Those connections have brought me lots of success, but they’ve also made any difficulties I’ve encountered much easier to bear, and have shortened the life cycle of those difficulties.

With that in mind, here are a few tips for how you can build your own connections with other entrepreneurs.

How To Meet And Connect With Other Entrepreneurs

There are lots of ways to connect with other entrepreneurs; here are just a few ways that I’ve found effective.

1. Join a Coworking Space

If you’re used to working from home or from local coffeeshops, it can get quite isolating and lonely. And isolation is rarely ever a good thing for an entrepreneur, and it tends to be a brake on success.

So if that’s you… I highly recommend you make the investment in a coworking space. Most offer affordable starter packages with flexible hours (e.g. 20 hours a month) and if you really like it and get a lot of value from it you can upgrade to a more permanent type of arrangement.

There are so many coworking places out there so I’ll just some general suggestions about choosing a coworking space:

  1. Choose a place whose culture and members reflect your own values and/or industry. For instance, if you’re in the tech space, it might make sense to join a tech-focused coworking space.

  2. Know what style of space you want: Do you want a place that offers a lively, social environment, or do you want one where heads-down, focused work and less interaction is the norm?

  3. Choose a place that you won’t easily outgrow: hopefully you’ll be doing more hiring over the coming years, and some of those people may conceivably work with you in a physical location. So choosing a coworking space that allows you to grow into larger spaces as you grow helps you avoid having to move locations when you grow (keeping in mind that most coworking spaces tend to focus on space for 1 to 10-person orgs).

  4. Meeting space is important: Even if you don’t do a lot of meetings (with clients, staff, etc.) at the moment, that may change so you want to choose a place that has lots of meeting spaces of various sizes. Also, if you plan on hosting events for entrepreneurs (see below), it might be handy to be a member at a coworking space that has the right rooms for your needs.

  5. Maybe stay away from Wework spaces for now :)

2. Attend Entrepreneur Conferences/Retreats

Mastermind Adventures  Patagonia, 2018

Mastermind Adventures Patagonia, 2018

OK, I’ll admit I’m a little biased here owing to the fact that I put on events for entrepreneurs. But getting out of the office and out of the day-to-day grind of our businesses is generally the best way for us to connect on a deeper level with each other.

I’ve attended a LOT of entrepreneur-focused events over the past few years. I’m going to write more about my favourite ones in a future post, but for now here’s a quick list:

Want to get notified when I announce new Mastermind Adventures events?
Click here to join the early-bird list, or click here to apply for an upcoming event
(Amazon in April 2020 and Greenland in June 2020)

3. Attend Local Events.

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Regardless of where you live, I’m willing to bet $50 there are local entrepreneur-focused events in your hometown (even a town of 250 people has local entrepreneurs, such as the owners of the local stores, and they probably get together every once in a while). is a great place to start your search for local events (just search ‘entrepreneurs’ or ‘entrepreneurship’ on the home page). For instance, searching just 5 miles within Toronto brings up over a dozen entrepreneurship groups, some with almost 20,000 members.

Or just Google search ‘_____ (your town) entrepreneur events’ and you’ll probably find lots of upcoming events.

Rather than attending every event under the sun, pick a few ongoing events and go deep (i.e. keep coming back to the same events where you’ll meet many of the same people). This will give you the opportunity to create meaningful relationships with a few people rather than shallow ones with lots of people.

3. Host Your Own Events

The Salon , Oct. 2019

The Salon, Oct. 2019

Sometimes creating the solution you need is the best way forward.

This is basically what I did with Mastermind Adventures, and what I’m doing with The Salon in Toronto: I wanted to connect with other entrepreneurs in a better way that wasn’t readily available yet… so in true entrepreneurial fashion I just built what I needed (and what I wanted to create for others).

If you want to host your own events and connect with other entrepreneurs, and don’t have a network of people to reach out to yet, I suggest you start with a very targeted approach.

Don’t try to appeal to all entrepreneurs, but rather narrow down your offer. This could mean appealing to tech entrepreneurs, visible-minority entrepreneurs, older entrepreneurs… whatever group or subset of entrepreneurs you want to connect with, and whoever you think would get value from connecting with that subset of entrepreneurs.

The more narrowly-focused you can be (up to a point, you don’t want your intended audience to be 3 people), the more likely your events will resonate with the target audience. For instance, fintech entrepreneurs would probably love the opportunity to connect with other fintech entrepreneurs, but they may not be interested in connecting with a group of entrepreneurs from retail, manufacturing, travel, etc.

Keep it simple at first, maybe just a monthly coffee or 1 dinner. Focus on creating deep value for everyone that attends, and then build from that first event.

p.s. are you in Toronto? Join my Toronto events list and get notified when I put on local events for entrepreneurs.

4. Join An Entrepreneur-Focused Organization

There are lots of peer-focused entrepreneur groups out there, some more formal than others, some quite expensive and some affordable (or free), with varying criteria for joining or becoming a member. What they all offer is the opportunity to connect with and learn from other entrepreneurs.

Here’s a select few that I either know firsthand or have heard great things about:

5. Deepen Your Existing Connections

You probably already have some existing connections to other entrepreneurs. In addition to expanding your network, consider deepening your connections to the people you already know.

I make it a habit to have coffee and/or lunch with the entrepreneurs in my network at least once or twice a week. I love talking to other entrepreneurs, offering value whenever I can, and learning what I can from them.

I especially love it when I can move someone from the ‘acquaintance’ category to the ‘friend’ category, and feel like I can count on them if I need help, or can offer them help when they need it. There’s simply no substitute for time invested into the relationship.

I also make it a habit to regularly reach out to the people I care about and let them know or remind them that I care about them. I now devote a few hours every week to reaching out to the people I care for.

It’s amazing the impact that small act can have on people, and it also impacts me as well: firstly, by fostering gratitude in me for the people in my life, and secondly via the responses I get from people and the knowledge that I’ve made their day a little better.

Here’s a response I got from a friend just this morning (someone I admire and respect, who’s being going through a hard time):

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Hopefully I’ve given you some ideas and inspiration for how you can start to connect with other entrepreneurs. I’d love to hear some of your own suggestions and thoughts in the comments below!



Mike Brcic,
Founder and Chief Explorer,
Mastermind Adventures