How to make friends as a founder

In this post, you will learn:

• Why founder loneliness is so common (and why it is dangerous)
• Five practical ways to build real friendships as a busy founder
• How a CEO peer group or founder community can provide the support structure you need

Alone in a bar

I sat at the bar alone. The beer next to me half gone as the waitress set down my salad and asked if I needed anything else.

I felt utterly alone.

"Who am I going to tell?" I asked myself. "How am I going to get through this alone?"

The day before, my (now ex) wife had told me she'd had an affair and that our second child was not mine. Suddenly, I found myself contemplating single parenthood with an 18-month-old.

I was also pondering how I might start over again, alone, and how I was going to survive all of this while also trying to keep my struggling startup alive.

Life had never felt heavier.

I had never felt more alone.

Since I was quite new to LA having only moved back two years prior, I did not have many close friends in town.

I needed friends. Real friends. People in whom I could confide what was unfolding in my life. And I needed them fast.

I was not going to make it alone.

I didn't need advice. I needed people.

Why founder loneliness is so common

I can see now looking back 7 years later that I was not unique in the aloneness I felt.

During some of the years since, I was a part of a CEO group that met monthly and did a pretty good job of getting real with one another and really opening up friendships. We met remotely and each of us was located in a different part of the country.

Several years in to our group, I remember several of the members confiding that in their 'real life' (ie outside our group) they did not have any friends like this. There was no one outside the group who really knew what was going on in their lives in the way that we fellow group members did. I remember the sadness and deep empathy I felt for each of them as they shared.

Now, as a coach, I hear similar sentiments from many of my CEO / founder clients.

Many leades I speak with confide in me in our earliest conversations how alone they feel in their life and in their founder or leadership journey.

Most of our leaders feel alone.

That is a huge fucking problem.

This is why CEO peer groups and real founder community matter. They provide what most founders are missing: people who get it.

The very real pain of aloneness

The founder / leader life is a hard life to live alone. The journey is a difficult one.

Building a company is fraught with ups and downs. The progress of even a successful company is a crazy rollercoaster ride.

Founders, more than anyone else in a business, feel the ups and downs personally.

In my own time as a founder/ CEO, there were days where I felt on top of the world. Revenue was growing, or some fancy VC's were courting us, or some critical hire said yes.

However, more common were days peppered with the acute pain of failure. When funding rounds did not come together, or a major revenue channel broke just as our bank account was nearing empty. Or, as happened that week I found myself sitting in that bar, something in my personal life away from the business fell apart.

Most founders are building their companies during crazy periods of their lives.

For me, I had just moved across the ocean back from Europe to Los Angeles. In the same two years, I:

• Moved two countries
• Got married
• Started a company
• Had my first child
• Bought my first house

Since many people build companies in their 20's or 30's, navigating similar life events my be familiar to you as well.

Companies are consuming.

As a result, while many people in their 20's and 30's are mixing it up with friends most nights, many founders are spending that time heads down on their business.

Many of the founders and leaders I meet wake up years into their business to find themselves quite distanced from the friends and family they were close with only a few years prior.

Often, that sense of aloneness comes, as it did for me, during a time when connection and support are most critical.

Whatever direction your work goes, whether your company implodes and you find yourself picking up the pieces, or it turns into the next $1B+ rocket ship, you are going to need support.

Sooner or later, every one of us wakes up to find that what we need most is that which we sacrificed in the early days to get here.

It is time to dispel the myth of the solo, fearless, cowgirl/cowboy founder who does not need anyone or anything but their laptop.

Isolation accelerates stress. Connection slows it down.

What is at stake

This crazy ride will take your life if you let it.

In the last year alone, I have spent time coaching founders who:

• Struggle with drug or alcohol addiction
• Face anxiety and deep depression on a daily basis
• Face major heart or brain issues
• Wake up to find they have lost all motivation for life and work

You cannot thrive alone.

In my earliest years as a CEO, when I did not have close friends around me, I found myself continually comparing my internal experience to the external experience shared by other founders in the press and on social media.

I told myself I must be doing it wrong because I seemed to be the only one struggling.

Without close friends, I found it impossible to maintain any sense of perspective on my work. I thought of myself as this emerging visionary who had exciting ideas for our market and our company. But the truth was I could barely see beyond the immediate challenge or emotion in front of me.

Without close friends alongside me, there was no one to help me lift my head up and see the bigger picture.

It is impossible to be an effective founder or CEO without the big picture. The big picture is perhaps the most critical part of the job.

If you're here, know this: seeking support is not weakness. It's leadership.

If you notice yourself in this article—the isolation, the founder burnout, the sense that no one really knows what's happening in your life—you're not alone. And there is a path forward.

Friends are good for business

Many of the CEOs I meet want to feel like every moment of their day is dedicated to the success of their business.

Time spent simply enjoying life, relaxing, or taking space feels wasted.

I have separate concerns and arguments about that, but even if we do design 24 hours a day around work success, I would argue that friends are good for business.

The 'friend time' is time well spent.

Startups are about solving your way around incredibly hard problems through ingenuity and innovation. To do that, you need to keep your head straight.

You cannot keep your head on straight alone.

Being an effective CEO is about seeing the bigger picture. Friends help with that.

Several years into building my business, I found looking backward that there were actually only 2-3 things that really mattered in any given year. Pivoting at the right time, finding that inflection-creating new feature, making that one critical senior hire.

It is hard to see what really matters if you are too stuck in the day to day.

Friends can help you pick your head up.

Here are three specific business benefits I've seen:

1. Better perspective: A close friend can see patterns you miss when you're in the thick of it.
2. Stronger decisions: Talking through hard choices with someone who knows you well surfaces blind spots and gut checks assumptions.
3. Emotional regulation: When you process stress with a friend, you return to work clearer and calmer. That clarity matters.

If you only do one thing this week: schedule one dinner or walk with someone you trust.

What are we doing all this work for anyway?

Business aside, relationships are kinda the whole point anyway.

Many of us started companies in part to find our way to financial freedom and to freedom of our time.

Those are wonderful things for which to strive. But isn't the point of having time and freedom the enjoyment of that time and freedom with loved ones?

Trust me, you do not want to begin making close friends once you have made it.

Start now.

By starting now, you may even discover that you do not have to suffer alone.

In my years as CEO, one of the most effective ways of lightening the weight of the role was a dinner with a close friend. Someone with whom I could be utterly me.

The friends who made the biggest difference were those with whom I could share the full spans of my life as it was at that time:

• The work challenges
• My fears
• Relationship challenges
• Questions of my purpose
• Joys and victories
• Dreams for the future

You can have this too. Now. Begin today.

Let's talk about how.

Here are five ways to start building real friendship this month.

How to make friends as an adult

Here are five ideas for getting started now building the support structure you dream of:

These are small actions. Compounding results.

Reconnect with those you have lost

You probably know that in your startup it is easier to resurrect churned customers than it is to earn new ones.

So let's apply the same strategy here.

Are there friends with whom you were once close but because of work, geography, or laziness you have fallen out of touch?

How might you invite them back into the fold?

Two outreach scripts that work:

Light reconnection: "Hey [name], I was thinking about you this week. It's been too long. Want to grab coffee or jump on a call?"

Honest reconnection: "I miss you. I let work consume me and drifted. That was on me. Can we grab coffee? I'd love to catch up."

Make it easy: Propose two specific time slots and a simple plan (coffee, walk, 30-min call).

Stop networking. Make friends.

In the starting and running of companies, the work frequently brings us into conversations with other founders.

As traction, funding, or other successes come our way, the invitations begin rolling in to networking events, dinners, conferences, and the like.

I used to hate that stuff.

I found anything that smacked of networking exhausting and tried to avoid it wherever possible.

I still hate a lot of it. But holding it with a different lens has been helpful for me.

I now look at any dinner or event with the goal of walking away with one new friend. Not 50 business cards or 'connections,' but one new, or prospective, friend.

Friends are way more powerful than connections. And they are way more fun.

The path to friendship is vulnerability.

So I try to identify the people (or one person) at any event who seems up for being real.

I do not dive in with my full life story (I save that for my writing obviously!) but I try to probe in conversation and I attempt to take the lead and share as openly as feels comfortable in the moment.

Vulnerability begets vulnerability. And vulnerability is, for my money, the most direct path to real friendship.

One friend per event framework:

1. At the event: Look for someone who seems open to being real, not just polished.
2. Start honest: Share something true about your week when asked "how are things?"
3. Follow up next day: Send a simple text or email.

Two follow-up lines you can send:

• "Really enjoyed our conversation last night. Want to continue it over coffee?"
• "Grateful we got to connect. Let me know if you ever want to grab lunch—I'd be up for it."

Be real with other founders

A note here on founder to founder relationships.

Can we all agree to be done with the 'I'm killing it' language?

Save that for Twitter. Or better yet, skip it all together.

When you have the opportunity to meet and spend time with other founders, take the opportunity to be honest about the crazy ups and downs of building a company from nothing.

Because you know what? They aren't killing it either.

There are few rooms more brimming with suffering than a room full of startup founders (OK, this is first-world suffering but you get my point.)

Try it.

You can start small.

Next time you meet a new founder and she asks how things are, look her in the eye and say 'it's been a tough week!'

Vulnerability begets vulnerability.

If we are going to build a startup ecosystem more filled with friendship and support and less filled with addiction and depression, it begins with each one of us.

A practical vulnerability ladder:

Level 1: "It's been a tough week."

Level 2: "Here's what I'm actually scared of right now."

Level 3: "Here's what I need."

Three ready-to-use prompts for founder conversations:

• "What's the hardest part of your role right now?"
• "How are you really doing with all of this?"
• "What support do you wish you had?"

Start with a list of 5 prospects

As I sat in that bar, all those years ago, I began in a way that perhaps you will also find helpful.

I knew I was not going to make it through that year alone. I knew I was going to need close friends around me. And I knew I did not have those close friends in Los Angeles at the moment.

But I did have acquaintances. And you probably do too.

So I forced myself to make a list of 5.

I asked myself, "If I had to choose 5 people with whom to share what is going on in my life right now with this crazy divorce situation, whom would I choose?"

I made my list:

• Warren
• Yanda
• Tracy
• Matt
• Meg

None of them were close friends at the time. Most I had only met in the last year.

But you know what's crazy? Fast forward to today and the people on that list are five of my closest friends on this planet.

How did that happen?

I took a crazy fucking risk in vulnerability.

One by one, I went down the list. I invited each to coffee or dinner. I shared the open truth with each of them of what was happening in my life. I said:

"I know we are not that close. But I have something going on in my life that I really need to share with someone. I am hoping you might be up for me sharing it with you."

Each person on my list received my hurt and my need with openness, empathy, and love.

And what beautiful friendships those fateful conversations beget.

I am not pretending that every acquaintance I had at the time would have been able to receive my grief with the grace those people did. Nor am I suggesting that you confide your deepest pains in the next person who walks through your door.

What I am suggesting, however, is that for each of us there is likely much more support and community available to us than we avail ourselves to in the day to day.

For me, the unlocking of that potential came with that decision on my part to get real and get vulnerable with the people in my life whom my intuition suggested were most worthy of my trust.

How might it feel to make your own list?

Criteria for choosing your 5:

• Trust signals: Who has shown up for others when things were hard?
• Empathy: Who listens without trying to fix or judge?
• Discretion: Who keeps confidences and doesn't gossip?
• Availability: Who is in a season of life where they can show up?

Next steps checklist:

1. Make your list of 5
2. Start with one person
3. Propose a specific time and place
4. Use the conversation opener that feels true to you

CEO peer groups and founder communities

Beyond individual friendships, many founders find structured support through CEO peer groups or founder communities.

I mentioned earlier that I was part of a CEO group for several years. That group became one of the most important support structures in my life. The members knew things about my business, my fears, and my personal life that almost no one else did.

It made all the difference.

What a CEO peer group is

A CEO peer group is a small, curated group of founders or executives who meet regularly (usually monthly) to support each other through the challenges of leadership.

What happens in a CEO peer group:

• Each member brings real challenges they're facing
• The group offers perspective, asks hard questions, and provides support
• Confidentiality is sacred—what's shared stays in the room
• A facilitator (often a coach) keeps the conversation productive

Outcomes I've seen:

• Better decisions (you get blind spots surfaced before making costly mistakes)
• Emotional resilience (knowing others face similar struggles normalizes the hard parts)
• Accountability (the group helps you follow through on what matters)
• Real friendship (over time, these become some of your closest relationships)

Who it's for: Founders and CEOs who want structured, ongoing support and are willing to show up honestly for others.

Founder community options

A founder community is typically broader and less structured than a CEO peer group. These communities offer connection, resources, and belonging without the same level of ongoing commitment.

Types of founder communities:

• Local communities: City-based founder groups that meet for dinners, events, or coworking

• Online communities: Slack groups, forums, or platforms where founders connect asynchronously

• Curated cohorts: Programs like Y Combinator, Techstars, or industry-specific accelerators that create built-in peer networks

The value: You get access to people who understand the founder journey, without the intensive commitment of a formal peer group.

How to choose what's right for you

If you're considering a CEO peer group or founder community, here are the factors I'd weigh:

1. Confidentiality: Is there a strong commitment to keeping what's shared private?

2. Facilitation: Is there a skilled facilitator or coach guiding the group?

3. Cadence: How often does the group meet? Monthly works well for depth. Weekly can feel like too much.

4. Fit: Are the other members in similar stages or facing similar challenges? Peer groups work best when there's shared context.

If you're not sure where to start, begin with a lighter-touch founder community. Attend a few events. See who you connect with. You can always deepen from there.

Hugs from LA

Wherever you find yourself today, I know that there are no easy or immediate fixes to feelings of isolation.

But there is hope.

And it is likely that the people who you need also need you too.

If you are putting off friendship for the sake of your business, take this post as a green light from a professional CEO coach to take some time away from your desk making friends. It just might be the best way you spend your time this year.

Your business will thank you because your mind will thank you.

More importantly, your future self will thank you.

If you want structured support, consider a CEO peer group. If you want lighter touch, start with a founder community and see where it leads.

Wishing you peace on the journey.

-Matt

Frequently Asked Questions

Q: I'm too busy to make friends right now. Should I wait until things calm down?

A: No. Things will not calm down. I spent years telling myself this. The truth is, if you wait for the "right time," you'll wake up five years from now even more isolated. Start with one coffee this month. That's it.

Q: I'm an introvert. Do I really need a CEO peer group or founder community?

A: I'm an introvert too. The beauty of a structured group is that it's contained—you know when it starts, when it ends, and what to expect. It can actually be less draining than navigating unstructured social events.

Q: What if I reach out and it feels awkward?

A: It might. Most meaningful things feel awkward at first. But here's what I've found: people are far more receptive than we fear. Most people are also lonely and would love to connect more deeply.

Q: I work remotely. How do I build friendships when I'm not in person?

A: Remote friendships are real friendships. Some of my closest founder friends I met through that remote CEO group I mentioned. Schedule regular video calls. Share honestly. Show up consistently.

Q: How do I know if I can trust someone with my real struggles?

A: Start small. Share something mildly vulnerable and see how they respond. Do they listen without judgment? Do they reciprocate with their own honesty? Do they keep confidences? Trust builds over time.

Q: What's the difference between a CEO peer group and a founder community?

A: A CEO peer group is small (5-10 people), meets regularly (usually monthly), and goes deep. A founder community is broader, less structured, and lighter touch. Both have value. Choose based on what you need right now.