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You know those people that seem good at everything?

The ones that came first in track & field in elementary, the straight A honour roll student, the type that gets a cool consulting job after college - you know the type.

I wasn’t one of those people. Winning seemed elusive and was always just out of reach.

For example, there were a lot of #17 place cross country ribbons in my room. There was an overwhelming amount of silver medals from rugby (I would eventually start tossing them in the trash).

I did an internship at a wealth management firm one summer in University for $5/hour in exchange for a higher commission. This bet on myself was a failure - I made almost $0 all summer. The saving grace was landing one “big” commission that arrived 1-week before next semester’s tuition was due (with no back-up plan).

I took on a risky job at a start-up with a significant salary cut for the promise of future equity. The founder dragged out that equity promise for 2 years, then delivered a humiliating low-ball % offer. So bad that I immediately quit.

My previous start-up, DealBuilder, went through more pivots than Dalmatians, while my other start-up friends reached dazzling valuations, exits, and growth. The saving grace? Receiving acquisition interest from the biggest player in our industry, only for the deal to die at the last minute.

While I was never last, I always felt second best. And, as a wise man once said, “if you’re not first, you’re last.” Or as my gym teacher put it, “2nd place is the 1st loser.”

There is a sentiment in sports that it’s better to win bronze than get silver. Bronze feels like a win. Silver feels like proof that someone stood exactly where you wanted to stand. While true, to a certain degree, there is no greater fire than a competitor in the face of suffering:

That quote is overused, but c’mon it’s so good. Especially when anyone over 40 has some sort of amnesia where they forgot that Michael Jordan actually missed a shot or two.

Now, I ain’t no MJ (I don’t gamble). But I have learned that success is sweeter on the other side of failure.

As I’ve previously written, I lived a strange double-life when it came to genetics. Until the age of about 15 - I was the smallest guy on any sports team. Not only that, I was slow and weak (picture: Diary of a Wimpy Kid).

This spurred a small man complex rivalling that of Napoleon. On the rugby field I would pick fights with the biggest guys, never stay down if I was hurt, and was always proving “them” wrong. Whoever “they” were.

To the surprise of everyone (including “them”), I would go on to add about 100 lbs and grow a foot between grade 10 and 2nd year University. For the first time in my athletic life, I was playing on a level field and the impact was immediate.

Ironically, all those years of playing a physical sport (rugby) undersized had given me an upper-hand vs the men who grew up as the biggest kids. They had never needed technique, because size did the work for them. I had needed technique to survive. The years of coming middle of the pack also gave me a work ethic that had faded from the 1st place cross country kids decades ago.

It has been the same experience since starting Breakwater. Experienced founders talk of the clarity the ‘second go round’ gives you as an operator and this has been my experience. Having been through the struggle of a failed start-up, decision making is easier and our growth has been 10x faster.

I see the same thing on the sell-side every week. The owners who get the cleanest exits are almost never the ones who had a smooth ride. They’re the ones who survived a bad customer year, a lawsuit, a partner split, a season where payroll was a coin flip. That scar tissue shows up in diligence as calm. Buyers can smell it.

The founders who’ve never been punched in the mouth are the ones who blow up over the first re-trade.

Don’t get me wrong, it has still been hard. But for what the inexperienced traveller calls plight, the wise traveller identifies as the journey.

As an entrepreneur it’s easy to feel like the first loser. To be honest, there are a lot of days that will make you feel just like a loser lol. Remember we have seasons, and winter makes us appreciate when the sun warms our skin.

So keep the landfill of silver. One day it’ll be the most valuable thing you own.

I am back to (try) and post more regularly on YouTube focused on buying & selling businesses. If that’s of interest, make sure to subscribe:

Credit: ideabrowser.com

Rebato - the unclaimed money map for new parents

12-minute EMOM (every minute on the minute), alternating:

Strength + conditioning. 5 rounds:

Rest 2 minutes between rounds.

every second counts