The Intersection of Sales and Wrestling

When I was in 7th grade, I was cut from my school’s basketball team. I was pretty devastated about it, and because I did not know how to skate, I could not try ice hockey instead. This left wrestling as my school’s only available winter sport for me. I knew nothing about wrestling and it did not seem particularly fun to me, but I signed up anyway.

Later that year, I had rattled off a successful season with only one loss on my record. In our school’s fitness testing in gym class, I had gone from being a mediocre athlete to having the fastest 50 yard dash time and the ability to do more pullups than anyone else in my class. All this to say, wrestling quite literally made me stronger, and I was relatively good at it.

Wrestling would ultimately become a passion of mine. I will not profess to have been an amazing wrestler, but I was my high school team’s captain and I wound up walking on to a Division 1 wrestling program for a couple of seasons, winding up as a starter on the team during that time period. Even in my adult life, I routinely watch college matches and usually attend the NCAA Wrestling Tournament every March wherever it is somewhere in the country.

Wrestling is a very difficult sport. It requires tremendous discipline not only in terms of intentionality with the technique, but also with proper nutrition and repetitive weight-cutting to achieve the desired weight for every competition. It is physically and mentally exhausting not only in terms of cardiovascular output but also in the way it fatigues the muscles. And of course you add the aspect that it is a solo sport where you compete against another individual head-to-head, which adds to the pressure and intensity of the sport.

When I was graduating college, I was not exactly sure what I wanted to do in terms of my career. I remember that I saw a sales position that said something like “The harder you work, the more money you will make.” This appealed to me, not just because I am financially-motivated, but more so because I really liked the idea of being in control of my own destiny. The rest is history, as I have made a career out of tech sales. But I imagine that is largely because of my experience with wrestling. So with that being said, I want to share some of the parallels between sales and wrestling and some of the lessons associated with them.

1. It is up to you

I think this is the number one parallel between sales and wrestling. In either case, it is entirely up to you whether or not you will be successful. Sales is a unique career in that it is very entrepreneurial. Most sales reps develop their own strategy in terms of who to target, how to target them, the quantities of certain behaviors they perform, and so on. What often separates good salespeople from the rest of the pack is a specific work ethic and paranoia about success, whether that comes in the form of attention to detail in sales assets put together for a customer or even simple paranoia about the risks to an enterprise deal. 

In that way, I think of the paranoia and work ethic of some of the best wrestlers. I often joke with my wrestling friends that the best wrestlers are mentally ill in some way. They have to be in order to inflict so much pain upon themselves for the pursuit of a greater goal. They realize that only they can carve the path for a successful future and they do not rely on others to make it happen for themselves. In that way, sales and wrestling are very much alike.

2. Never give up

In sales and wrestling, persistence is key. We know that in a sales environment, for example, there is a saying that “the sale starts with ‘no’.” This means that you do not really start “selling” anything until you face resistance. Naturally, this requires persistence on behalf of the seller to not take “no” for an answer and to push for a “yes.” Similarly, it takes, on average, 17 or 18 cold outreaches to an individual before yielding a response. Again, this means that the seller needs to never give up and has to have an attitude around poise and persistence.

Wrestling is no different. It is the ultimate battle of wills, and wrestlers will often refer to “breaking” an opponent, which is a moment in competition where someone becomes emotionally or mentally broken. To break an opponent almost certainly leads to victory, because a morally defeated opponent in such a tough sport really does not stand a chance.

For me, this phrase has some personal meaning. I quit the wrestling team in college and wound up regretting it for the rest of my life. Of course, most people would never have even made the decision to join, let alone to have trained and competed for a couple seasons. But it really weighed on me to not have finished something that I had started. In my journey in startups, there have been dozens of times where something went wrong or someone made me an exciting offer to leave but I never gave up. The reason for that is because of how I felt giving up wrestling. I never wanted to have that feeling again.

This desire to never quit translates to my personal life. I ran the Boston Marathon a couple years ago and got rhabdomyolysis in Mile 11. This is a life-threatening condition that presents itself in the form of very painful muscle spasms. Most people would have quit immediately; indeed, a doctor would say to go to the emergency room. I have never been in more pain in my entire life, but I did not quit. And that is one of my proudest moments to have finished that race in spite of that insane obstacle.

3. It’s Hard

Sales is not for the faint of heart. Neither is wrestling.

In high school and college, I would routinely cut anywhere from 10 to 20 pounds a week in order to make weight for a match. At the collegiate level, we worked out at 6am and 3:30pm every single day. Wrestling a seven minute match leaves you tired and breathless, as you go full boar for that entire time in what is ultimately a very physical and brutal sport.

Sales is not easy by any stretch of the imagination. For one thing, you get rejected an overwhelming majority of the time. A 5% success rate on a cold e-mail campaign could be deemed successful, and a close rate of 20% from sourced opportunity to close would also often be seen as a positive data signal. This means you are losing 95% and 80% of the time, respectively, in terms of those two activities. Not to mention the overwhelming amount of work involved to win a deal, which, at the enterprise level at least involves gathering momentum amongst multiple stakeholders and champions and bringing about a thoughtful business case that is predicated upon loads of research about the business.

4. “Champions are made while no one is watching.”

Dan Gable is one of the most decorated wrestlers in USA history, and I love his quote “Champions are made while no one is watching.” Sure, the bright lights shine come match day but it is really the culmination of all the hard work behind the scenes that makes someone successful in wrestling. At the end of the day, it can be a thankless journey, because for every minute of actual competition you endure, there are hundreds of minutes of preparation behind the scenes.

The same is true of good sellers. They can watch tape these days with all of the call recording tools that are out there, but good sellers really need to prepare for every single meeting and go back and make sure they hear every detail the customer says. Moreover, there are more opportunities for professional development today than there have ever been in human history. Some universities are even starting to offer sales programs.

There is an old saying that “practice makes perfect.” That is certainly true for wrestlers and with the influx of sales training programs and communities, it is always possible for sellers to be learning and upping their game as well. 

5. Failure makes you better

This leads to the last parallel between sales and wrestling: you need to embrace failure. I talked about this earlier already but you face a ton of rejection in sales. With that rejection comes endless opportunity to learn and improve. In my current company, we were able to look at our Closed Won and Closed Lost data to build an intricate grading schema that helps us understand who to target and why. We also would have a weekly Closed Lost review and a Demo Review meeting so we could interpret why we lost opportunities and how we could make each demo better.

Wrestling taught me how to deal with failure. I went to a pretty good high school full of cerebral kids who were not really used to failure. Wrestling forced a lot of us to reconcile with the concept of not being the best at something. But in that endless failure is also endless opportunity to keep getting better, and that is actually quite exciting for cerebral people who enjoy taking on new challenges. Indeed, I would say this is the most important lesson for anyone thinking of embarking on a career in sales or just taking on wrestling as a sport.