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Notes from the offices of Mizzen+Main

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Ten Years & Ten Lessons


Ten years ago, after many months of getting ready to launch, and many years of wanting to do so, I hit publish on the Mizzen+Main website. Shortly thereafter, we held our launch party benefiting Taylor Morris. 

I’ll be honest, I thought we were destined to go “to the moon” and that it wouldn’t be that hard. Ten years later, I’m in awe of what we’ve built and chuckle at how ridiculously naive I was. I’m also grateful I had no idea what I was in for. After a few friends and family graciously supported me at launch, the excitement quickly wore off. So did the sales. It was time to build a brand and a real business. 

While most lists of lessons feel cliche, I’ve been asked a lot of times about the journey. Since we just turned ten, here are ten lessons so far.

1. It’s much, much harder than you can ever imagine. Go for it anyway.

2. It’s very likely that you are not an entrepreneur. Only time will tell. 

Sometime between the start of Facebook and Uber, entrepreneurs became as celebrated as athletes, celebrities, and rockstars. Whether in search of fame or riches (or both), many believed they could build a business from the ground up. But entrepreneurship requires a unique set of skills and a specific mentality. It requires a relentless ability to get hit and stand back up again with all of it on your shoulders. That’s not for everyone.

To be clear, it doesn’t mean entrepreneurs are better or the entrepreneurial skill set is superior. Your skillset might be positioned to create significantly greater value in a specific area or at a larger organization.

Know yourself, your risk tolerance, and your unique abilities… then find those with complementary capabilities and build something exceptional. Just be careful you aren’t chasing an idea of who you wish you could be rather than what makes you truly great.

3. Focus on small, consistent wins.

We had some huge wins at Mizzen+Main. From a breakout podcast sponsorship of The Tim Ferriss Show to a very early endorsement deal with JJ Watt.From an exciting growth investment from L Catterton and a ridiculously awesome partnership with Phil Mickelson that saw him wear our dress shirt at Augusta with Tiger Woods and a viral commercial (you know the one) that looped on every talk show on ESPN for days on end..

If those were the things that sustained us, we never would have made it. The small, consistent wins are how you maintain balance, excitement, and teamwide enthusiasm.

Here are some examples of the things that I remember that really put the wind in our sails, day in day out:

  • Realizing it had been weeks since a day had gone by with no sales
  • Building out our first real office
  • Celebrating the first team member to have a baby
  • Getting our first wholesale account
  • Finding out Mark Cuban loves our product
  • Hitting 100 wholesale accounts
  • Putting a bell up in our office to celebrate wins together as a team
  • Growing to 20 team members… then 50
  • Opening our first store
  • Hitting our 500th wholesale door
  • Our first million dollar month
  • Surpassing one hundred million dollars in sales
  • Embracing the enthusiasm of pro baseball teams seeing us show up for locker room trunk shows
  • Congratulating exceptional team members who earned amazing opportunities elsewhere (becoming CEO or CMO at another startup)
  • Reading the wonderful feedback and support from our customers, daily

Do you see how much more sustainable these things are? Just like life itself is not Kodak moments alone. It’s everything in between that ultimately matters most.

4. People are the greatest and most profoundly challenging parts of building anything worthwhile.

The highest and lowest experiences over the last ten years have been because of the people I had the privilege and reality of working with. 

When I started Mizzen+Main, I had never even interviewed someone, let alone managed them. I had no P&L experience. I had to do every single thing that needed to be done (my wife helped out tremendously while still working a full time job to keep us afloat) until the team could be expanded. 

This reality, coupled with my experience in those early years, ingrained in me two beliefs/practices that color everything:

  • I have a deep belief in people and their potential. Your background and college or degree (or lack thereof) don’t mean a whole lot. Certainly some roles (i.e. accounting) require specific training, but otherwise, if you’re willing to work hard, stay humble and curious, and have a great attitude, you’re going to be successful in our organization.
  • I won’t ask anyone to do something I wouldn’t do or haven’t done (a lot). Period.

A few other lessons about people I’ve learned the hard way:

  • People you deeply trust will betray you. It will hurt worse than you expect, especially because you’re carrying such significant weight around all the time. Don’t stop trusting people… but…
  • …If you never allow yourself to be surprised by people’s behavior, it makes things easier day in and day out.
  • People you hardly know will amaze you in the best ways. Some will become the most special and important people to you. Creating an environment where people succeed and realize their true potential is one of the most rewarding aspects of building an organization.
  • Your company will outgrow some folks, which becomes especially hard when you care about them a great deal. Sometimes it’s your fault. Other times, it’s just the natural course of things. It’s just how things evolve. 
  • Focus on building a team even though it feels better, even more true to who you are, to say you’re building a family

Ultimately, I’d suggest reading The Hard Thing About the Hard Things by Ben Horowitz. I’d read it in the early days of building Mizzen+Main and many of the same experiences came to pass. It’s an invaluable resource.

5. Almost no one really knows what they’re doing, but some people are superior at leveraging information and making better bets.

When I started, almost every “expert” told me what a terrible idea performance fabric dress shirts were. We were laughed out of our first trade shows. Anyone who had invested in the space passed on us, or even refused a meeting. It was so consistent, and frustrating, that I effectively tuned out all experts. Unfortunately, I ignored them for too long. I should have engaged some level of expertise sooner, and it ended up costing us time, money, and wasted opportunities. I would have saved a lot of headaches for our team if I had brought in experts earlier on in our journey.

6. Humility is the most underrated trait in top performers, but you have to balance it with an ego that drives people to succeed.

People are good at faking humility and hiding their lack of it for a period of time, but eventually, it catches up to everyone. Ego without real humility is deadly, for your business or someone’s potential. At the same time, humility without ego fails to produce greatness.

True humility with a balanced ego (aka confidence and drive) is as good as it gets.

I’ve watched people without humility cause exceptional damage to the business while I either didn’t realize it or failed to acknowledge what was really happening.

As you interview people, push hard to truly validate humility. Over time, the folks who you thought had humility can either lose it or lose their ability to hide the ego that was there all along. By the time you realize a lack of humility is a real issue, you’re already way too late in addressing it.

7. Your network and your ability to respectfully but meaningfully leverage it is indescribably important.

We raised our first four million dollars from about forty angel investors over about four years. Most of that was from folks who knew me, trusted my integrity, and believed in my ability to execute. Our work with JJ Watt came from an introduction from friends to a part of his broader team. The partnership with Phil MIckelson came via a longtime friend to his team. A friend who worked at Ernst & Young introduced us to the Entrepreneur of the Year program. Attending their Strategic Growth Forum led to a relationship with L Catterton, who led our growth fundraising round. That friend is now our President. You never know where one introduction can lead.

8. No one will steal your idea until you’ve proven it’s really, really worth copying (or stealing).

I wasted so much time and energy worrying about someone stealing the idea to make a performance fabric dress shirt. Marc Andreessen has reiterated Mark Twain’s concept: there’s no “new” idea. It’s all about repackaging them with a “new and curious combination” that ultimately matters. 

It all comes down to execution. Yes, mimetic desire is a real thing, and people will copy your idea in time.

9. Be open to most suggestions but say no to almost everything.

It’s impossible to know most of what you need to do. The only way you can hope to make the best decisions with the information available is to listen and learn, constantly, from myriad sources. In reality, you also have to filter most of it out because no one is in the same boat you’re in. You have your own advantages, challenges, and team. 

10. Be realistic with yourself, your potential, and your risk tolerance, but don’t let any of the cliches stop you from launching something great.

If you don’t start your idea because “expert” investors tell you:

  • It’s too early
  • It’s not defensible (aka you’ll be copied)
  • It’s too hard
  • It’s not a big enough market

Then you’ll never start. Nothing worthwhile would have ever started if people had listened to the doubters and naysayers. Palm was worth more than Apple and Amazon in 2000. When Peloton started, the total addressable market for stationary bikes was around $2B. Who needs another email app? Superhuman is nearly a billion dollar company. Go for it.


Your health and mental wellbeing should be more important than ever. Treat your body and mind like a professional athlete, and you’ll meaningfully increase your odds of success.

I lost my way a bit along the journey. I wrote about a big part of how I got it back on track here.