How Getting Punched in the Head Helped Me Build a Better Startup

About a year ago, I took up boxing more seriously. While I had enjoyed boxing already, the classes I took typically were more boxing as cardio exercise and less boxing as a sport. It was a great workout and a fun way to pick up some boxing basics. And then I started sparring.

Now, instead of just a sweat busting workout, I had the fear, danger, and reality of getting punched. It’s a strange feeling getting punched in the face. It’s not something anybody (hopefully) has ever experienced, and it’s certainly not pleasant. But the learning involved, the fun of the strategy, and the sweat-a-thon workout motivated me to dive into the sport.

As we’ve also worked this past year to build Mason Park, an e-commerce marketplace, I’ve noticed that many of the same lessons taught to me from boxing apply to running a business and building a product.

In both cases, I had some relevant background experience (prior cardio boxing experience for boxing, prior product management experience for our startup), but not exact experience. And in both cases, what I thought I knew and what I actually knew were quite different things.

What I thought I knew and what I actually knew were quite different things

Here are some of my favorite lessons learned from boxing:

You will get punched. Get over it.

In boxing you will get punched. You won’t know when, you won’t see it coming, and it oftens happen so fast you’ll feel blindsided. The first time I got punched I was dismayed and embarrassed. But after a few seconds, I realized I was fine and things were OK. Getting punched actually enabled me to learn. Once I opened up to the fact that it will happen, I was able to focus on learning and not on the embarrassment I felt of getting punched in the face.

“Once I opened up to the fact that it will happen, I was able to focus on learning and not on the embarrassment of getting punched in the face”

Similarly in startups or in business, things will go wrong. The first email campaign we sent out got zero responses. The first release of our product had a bug that prevented visitors from purchasing anything (it kept users in an endless loop of user login error). It was embarrassing and sure made us feel like screwed up big time – when things were most critical.

But once we began to accept that things will go wrong and likely at times when you least expect them, it enabled us to focus on recovery, rather than dwell on the negative event.

You will get punched. Get over it and move on.

Screenshot 2017-06-24 at 6.11.10 PM - Edited
Guess which one is me.

Jab, cross, hook. Have a plan.

The first time I sparred, my excitement and nervousness levels were through the roof. With the adrenaline pumping, I would hop, run, and swing my fists all over the place hoping something would work. Over and over my instructor would tell me “Have a plan. Don’t just go in swinging.” This meant pre-planning a sequence of punches I would execute on and not just “going with the flow.

So I did this. And I still got hit.

I was reminded me of the amusing Mike Tyson quote “Everybody has a plan until they get punched in the mouth.”

“Everybody has a plan until they get punched in the mouth” – Mike Tyson

What I learned was that this lesson actually consisted of two parts:

  1. Have a plan and execute on it
  2. Learn from the outcome and adjust accordingly

Sparring thus becomes a feedback loop of testing a specific strategy of punches, observing the outcome (eg. did I get hit or did I hit my opponent?), adjusting accordingly, and then executing again.

“Have a plan. Don’t just go in swinging”

We found the same strategize-execute-observe loop with Mason Park. We quickly noticed that if we addressed issues as they came in, we’d be on an infinite directionless chase of whatever happened to be hot. We had to have a plan with what we would address and how and when we’d do it all.

For example, through our analytics and user feedback we knew people were getting confused with what was available on Mason Park. We hypothesized that we needed to visually merchandise our inventory in a manner that gave visitors an overview of the inventory. We merchandised a small category on the site and tested it with some users. We learned that our strategy wasn’t perfect, but it was a step in the right direction. From there, we revised our approach and tested again.

In both cases it’s necessary to strategize, execute, observe, and adjust accordingly.

Have a plan, even if you do get punched in the mouth.

Watch the body, not the gloves. Clues can be in unexpected places.

Often times when I sparred, I ended up focusing on my opponents gloves as I desperately tried to avoid getting hit. In boxing, it’s pretty obvious to pay attention to your opponent. What’s less obvious is the fact that you need to pay attention to seemingly insignificant clues, and often together.

“Don’t just stare at their gloves and don’t just stare at their head. Watch their chest,” I was told. Slight movements in the chest area could signal an opponent’s next move. Once I stepped back from just focusing on one area and paid attention to clues from all around, I was much better able to predict and react to my opponent.

With Mason Park, we initially did what we thought was best – focus on what users told us they thought about the product. What we learned though was that doesn’t paint a complete picture. What users were telling us and what users did was often contradictory. Watching users in action on Mason Park told us a lot about their true behavior, and even more telling was observing our users navigate other sites. If we focused on just what was in front of us or what we were told, we would’ve missed the true insights.

“If we focused on just what was in front of us, we would’ve missed the true insights”

A punch doesn’t come from the fists, it starts from the body. Watch the body.

If you aren’t punching you aren’t boxing. Have courage and punch.

When I first started sparring, I spent most of my energy trying to avoid getting hit. And when I did punch I ended up punching from such a distance that I had no chance of ever making contact. The fear of the situation caused me to burn energy and act without any courage that would lead to an effective punch.

One time my sparring partner just dropped his hands, stopped moving, and waited. I would still do nothing but bounce around. I wasn’t actually boxing and I certainly wasn’t learning how to box. Once I realized that in order to actually learn and box, I not only had to have the courage to punch, but I also had to believe I could hit, and actually try to hit my opponent.

With Mason Park, everyday we’re faced with decisions and challenges that we’ve never faced before. We weren’t sure we were running adwords correctly or we weren’t sure we knew how to approach boutiques we wanted to partner with.

With so much doubt we initially just dabbled or worse – talked more about our strategy than actually executing our strategy. We learned we had not only have the courage to make the decision, but also to execute on our decision with confidence.

We’re never 100% sure on our decisions, but if we don’t make any decision and act, we’re certainly not going anywhere.

“Sometimes, we spent more time talking about the strategy than executing on the strategy”

After about a year of boxing, I wouldn’t say I enjoy getting punched anymore than I did before. It’s certainly still not a pleasant feeling. But with every punch I’ve taken, and thrown, I’ve learned a little more, gotten a little better, and had a little more fun.

Similarly, we’re still faced with challenges and unknowns with Mason Park. But with every decision we make, and execute on, we learn a little more, get a little better, and have a little more fun.


Let me know what you think. I wrote this essay to capture some of the learning from my experience with starting Mason Park and welcome any feedback.

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2 responses to “How Getting Punched in the Head Helped Me Build a Better Startup”

  1. […] wrote about some key learnings from my experience in posts here and here. What I’ll reflect on in this post are some of the fun and not-so-fun aspects of my […]


  2. […] many years, I found that feeling uncomfortable and not particularly enjoyable. It’s like when I get punched in the head boxing, why would anybody enjoy […]


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