Startup Lessons Learned from My Boxing Matches

Startup Lessons Learned from My Boxing Matches

What training for a boxing match taught me about entrepreneurship

Jab, Cross, Block, Train, Knockouts, Knockdowns, Get Up, Respect, Try Again

Overcoming Fear

Wheezing and sweating as I jogged down the street I’d pass by a boxing gym. I did this for 2 years before I had the nerve to walk in and start taking beginners training. As soon as I started I was hooked -- I fell in love with the sport, its culture and the community it generated.

You will feel this way when you begin your startup. You don't need to wait two years to enter into your trial run. Just start, and after you begin you will totally fall in love with your work.


Two years later I was primed for my first amateur bout. It was time to express in competition what I pursued in training. As I stood in the locker room placing my mouth guard in I remembered my first sparring match.

My trainer/friend Santiago was kind enough to wrap my hands in preparation for the fight. I had trained for weeks and weeks, mentally built up this moment and couldn’t believe I was just a few minutes away from my public match.

A muffled roar rose from the adjoining room where the crowd was enjoying the 3rd match on the fight card, I was 4th. I was ready, nothing to do but sit there and wait for my turn. It was in this moment of anticipation I asked myself how I got there.

It's important to be aware of what steps you are taking in your startup so that you can repeat the process on another project. What go you here. Was it your dedication and focus? Was it your product and preparation?


In your business ventures, are you aware of what is going on? Do you know who your competition is? Who is your ideal customer persona. Are you missing something? Is something standing right in front of you that could add pizzaz and that could be wonderful -- that you haven't noticed, or cannot see?

So off I went for a little sparring. Dave was in his seventies, an ex-Army Ranger, retired Manufacturing engineer and a life-long boxer. My trainer asked me if I’d like to spar with him.


“Sure, I’ll be sure to go easy on him,” I said. My trainer just smiled and helped me put on my head gear.

Mouth guard in, gloves up...ding! We went back and forth for a few minutes and before the first round was over he caught me with a solid jab on the nose, my ego was checked and I gave Dave the respect he deserved. For the remaining rounds in the sparring match he made me pay I made one contact, he didn’t have as much mobility or flexibility, but his sense for timing was impeccable.

Successful timing, in terms of starting and running a startup enterprise, is a combination of continuous awareness, aka metrics, and a concerted response to the situation when metrics line-up.

For example, downloads are up, but so are requests for clarification on how to use your platform - it’s time to get write blog, make a commercial, create a tutorial or a marketing collateral that will walk new users through the ins and outs of your platform.

It's Identical In Boxing. 


The mainstay of any mature boxing style is the jab. The classic jab is a very quick extension and retraction of the non-dominant arm straight out directly at your opponent. It is absolutely imperative to use it as a primary tool for measuring location and distance, it is the boxing equivalent of a submarine’s radar system. It is common for a boxer to throw dozens of quick jabs to track and ‘set up’ the right situation for a concerted response.


Concerted Response

The concerted response in this case is the cross, which is a power-punch from the dominant hand. It’s a very forceful response simply because the movement is designed to leverage your body weight into your cross.

It starts out by raising, or keeping, your dominant foot on it’s ball and twisting your entire torso into the punch. This, in comparison to the jab, is meant to be used sparingly as it is a large investment in energy. If done well, can leave your opponent open for multiple combinations of offensive moves. In this sense, it is the submarine’s torpedo.


Your concerted response for your startup is also a power-punch. You have to be ready for the large investment in energy. In all business it's important to be correctly situated and be the torpedo in your space.


Make sure your startup product or service is something worth fighting for. And if it is you need to be all in. All invested in what you have to do.

In My Boxing -- As In Your Business

It will become official: You will get the date for your first amateur startup fight.

I had just gotten the date for the my first amateur fight - my diet was well under way, I was alternating endurance and weight training. I was meeting my trainer, Chris, who a multi-time Golden Gloves winner. Also, four times a week, and for good measure I was doing Yoga to ensure flexibility.

This is considered a very light regimen for a professional fighter, but I was an amateur boxer.

Even more concerning to some of my acquaintances was that I had a full-time job. Oh. Did I mention that I was in the middle of releasing an app? This was the most involved and the most I had done at any one time before -- but the challenge was not a burden. I was very busy -- but it was exhilarating. 

There was a pleasant, underlying intensity I felt within that would resurface every time I’d refrain from dessert, wrap my wrists for sparring or stay in the ring a little long or practice on the weekends. I knew why I was doing what I was doing and it energized me.

The only other time I had that same feeling was co-founding a mobile app based company: Parts Detect. I was not just a member of the company, or an employee, I was a cofounder - I was part of it and it was a part of me. It gave my responsibilities context and my sacrifices meaning that I could feel on a daily basis and it made all the difference.

Success takes on many forms and regardless of what success means to one’s enterprise it is rarely a clear road and often pushes people to their limit. Embarking on such a journey with purpose is second to none when it comes to long term success.


Walking up to the ring I felt the eyes of the crowd at my back, I was more awake and amped up than I have ever been in my life, I felt ready! I met the ringside physician for a pre-fight check up, still felt great, then walked over to the ring.

My teammate, Ben, parted the ringside ropes and that's when I realized that my gloves weighed a lot more than I remember, and my legs were getting tired and my thoughts were slowing down.

I realized that this is exactly what my coach told me to keep in mind the adrenaline rush left and my body was now in the midst of the adrenaline drop, aka adrenal crash. Understand the biology of this phenomenon both mentally and physically. Just like that my initial boost was gone...ding! Round one began.

Pre -- And Post Launch Fatigue.

In preparation and execution for the big day to launch your startup, keep in mind that you will most likely feel spent. It will be unbelievable to you that what you have been working for, striving for, putting in the hours to develop -- and you feel totally drained.

You need to be training to handle this part of your startup launch -- especially mentally preparing for it. You are tired, but realize that you have been tired before and you have pushed through and done what you have to do. So much more to do, and you can.

You won’t know what it’s like until you get there, but just knowing that this strange physical and mental adrenaline drop will happen makes a positive difference. You will expect it -- no what it is -- and you will handle it.

There is no real end to anything in life, and the same goes for your startup. There will be no finishing point, you are just beginning. It will be a constant effort to find a balance so that you can stay on the path toward your next goal.

It's the same with boxing.