Struck with self-loathing every time you hear of someone else’s success? You are not alone.

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“As of this week, my personal net worth has hit nine figures,” my client said.

It took me a moment to sort what that meant.

One hundred million dollars!

Wow, I thought. That is a big number.

In coaching, part of what we train for is to notice our thoughts, reactions, and emotions in sessions. We are taught to identify them so we can set them aside and remain present for the client.

At this moment, what I noticed was I felt simply happy for my client. It was not happiness…

Leverage the power of check-ins to level-up meetings and bring your team closer

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The most distracted CEO I know

Matt needs to shore up his communication patterns in 1:1s and in smaller group settings. Being able to refine and get a bit better in those smaller interactions will make a pretty distinct impact on the company. It is a combination of things that would be helpful (active listening, truly giving off the feeling of being receptive, and having the other person feeling heard or valued).

Wow, that makes me cringe to read. That quote is snipped from a 360 review of me, as CEO, in the summer of 2016. …

Founder burnout, depression, and loneliness are rampant. Too many founders struggle in isolation. Let’s bring that to an end.

Originally posted at Subscribe here for regular updates.

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…

Practical steps for moving through the fear that you are not enough

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A fateful walk

I was trying to hide the tears welling up in my eyes. It had been a tough day in the midst of a tough week, month, and year.

The Series B we had been preparing for the last year was not coming together the way we hoped.

We were living on debt.

Our revenue, which had been growing steadily for over a year, had suddenly cratered. Our best acquisition channel imploded when our domain got dinged and our email deliverability rates went through the floor.

Even now, sitting in a cabin…

What if your deep care that your company succeed is actually the greatest impediment to such success?

Destroy the idea that you have to be constantly working or grinding in order to be successful. Embrace the concept that rest, recovery, and reflection are essential parts of the progress towards a successful and happy life.

- Zach Galifianakis

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We were 20 minutes into a coaching session aimed at sharpening my client’s company’s goals for the year. I was challenging her to begin by zooming way out.

“What do you most want to have achieved 10 years from now?” I asked.

“I want us to have built one of the…

How to turn your board into your greatest ally, get more support, feel less alone, and do your damn job.

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It was my very first board meeting, and I had no idea what I was doing.

Although I had been running my startup for three years, I had never had a board before. To be honest, even with an MBA under my belt, I did not really know what a board was supposed to do or how it was supposed to work.

As the meeting started, I walked my one board member through the long deck I had meticulously prepared.

I spent the next two hours trying to convince her…

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In 2014, I found myself going through a time of tremendous change and stress. I was the CEO of a company that had recently raised our Series A. We had ambitious plans for the year, and I needed to show up with a clear head for the work at hand.

But at home, I was facing the loss of a child, a complicated divorce, and my first few months as a single-parent.

Life was overwhelming to say the least.

Up until that point, I was not particularly intentional about my…

We applaud grit, long-hours, and blowing through walls. But great entrepreneurial work tends to come more from creative insights and thoughtful reflection.

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“Random depression”

I received the following email from a client this morning:

I think I’m dealing with a bit of random depression so I’m trying to get out of the funk.

One of the many gifts I have discovered in moving from founder CEO to coach has been the normalization of my own ups and downs.

The creation of something from nothing is a curious thing.

It requires energy, motivation, and creativity.

And each of those things can be fleeting.

On the days when you find yourself low on any one of…

If the data is correct, you are not doing yourself any favours by grinding it out after 5 o’clock.

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I could not believe what I was reading on the slide.

My co-founder and I were seated side-by-side at First Round Capital’s annual CEO Summit at the Contemporary Jewish Museum in San Francisco.

Although I had heard about it for years, this was my first time at the Summit . I felt intimidated by the name tags I was reading on the founders seated around me:

  • Leah from Taskrabbit
  • Neil and David from Warby Parker
  • Sam from Hotel Tonight
  • and on and on….

Everywhere I looked, I saw one of…

Startup folk are renowned for geeking out on productivity hacks and innovating on the future of work. But most miss the easiest gain of all.

Originally posted at

I spend a lot of time with startup CEO’s, founders, and executives. As a coach (and previously as a founder/CEO), I am routinely inspired by the energy, vision, and no-quit attitude that I observe. But there is one mistake that I see in nearly every leader I meet.

An early stage company’s primary currency is focus. A startup is at a disadvantage against a large incumbent on nearly every measurable variable. Resources, depth of leadership, industry experience, marketing might, etc., the incumbent wins every time. …

Matt Munson

CEO coach @ Angel investor. Startup founder. Committed to helping leaders feel less alone in the journey.

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