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Ascent Publication

Why I Look for the Bad and the Good

Don’t fall for the high school quarterback effect.

There is no question that a mentor or speaker is a better version of themselves when they are teaching and speaking from experience.

One of the hallmarks of great leaders is that they’re great at storytelling. A story is a great way to demonstrate what needs to be said and to make sure that what is said is what is being heard. All talk too often we think, “Well, I’ve said it, I’ve instructed them, so they must understand it completely.” That’s not necessarily the case.

Experience comes in two forms, good experience and bad experience.

Would I join with someone who has only had bad experiences? No, I would not. Clearly, they’re either very unlucky or (more likely) haven’t taken those bad experiences, learned from them, and adjusted in such a way that they can create positive outcomes from them.

On the other hand, do I always want to partner with someone that only ever wins, and the experience is only positive? Similarly, probably not. They haven’t learned how to lose and comeback from a loss.

I coach my son’s under-12 rugby team and, last year, we were the state champions. This year we had a better team, better talent… and we lost in the semifinals. We went undefeated this whole season, all wins and one draw; no one has beaten us. Keep in mind, these are 11- and 12-year-old young men, during the whole season they hadn’t learned how to lose, they hadn’t learned how to grind it out during a long match. They hadn’t developed the mental toughness that was required, notwithstanding the physical skill, for them to be ultimately successful. That’s on me, as the coach, to create that mental toughness as best I can.

I thought I had. The eventual loss showed me I had not.

Likewise, I want someone I’m working with to know how to lose; to be able to fall down and get back up. I also want them to know what it takes to win. Ideally, I want that leader to have great experience so they know what to do and know how to put runs on the board. They should have some negative experience, so they know what not to do and how to avoid obvious pitfalls. They should know how to negate them, how to minimize them, how to not have them be part of the play going forward.

That’s the sort of experience that I want to follow. Now, I’ll extend that one step further. I love practical experience. I’ve paid a higher tuition on some of my practical negative experiences than I have at a top college for my master’s degree. And that was not inexpensive.

I believe that good educational and institutional experiences combined with personal experiences are critical to success.

The ideal individual has both positive experience and negative experience, and you decide the balance between the two. Do they have theoretical experience and knowledge because they understand the constructs behind it and the drivers of it? This trains your mind to be more intuitive and inquisitive. Do they also have practical experience? For which they’ve likely paid significant tuition?

One of the challenges with entrepreneurs is they believe, what I call, the INC-500 myth. The idea is that all startups need to get on the INC 500. Now, I’m impressed by those companies that do. But not all companies are built to do so, not all spaces that are played in are able, by definition, to make that threshold. So entrepreneurs get too carried away with the press of high growth and the personal branding of “I am the next insert-famous-entrepreneur here.”

They lose sight of the fact that entrepreneurship is about delivering value to the marketplace, and doing it at a positive margin. Amazing and astounding your customers.

All too often, those entrepreneurs get caught up in the personal branding value of that enterprise, and conflate the two issues: themselves and the enterprise.

I also smile at what I call one-hit-wonders. Think of a rock band that has one hit song and never tops the charts again. It’s interesting to watch entrepreneurs that way-back-when were successful, had a great hit, and have been riding on that success ever since. Be wary of that individual. Because, more often than not, that initial success was a function of the team they were a part of or they were just darned lucky. They might be losing ever since, and riding on that past win to maintain their relevance.

None of those things are what you want on your team, or in the advice they give you.

I call that the high school quarterback effect. When you’re in your 50s, I really don’t care that you took your high school team to the state championship and won MVP. Good on you. But that was yesteryear and adds nothing to the enterprise in which we’re talking about engaging with you. Yes, there are some lessons that you may have learned from that. But if you have to refer back to your high school experience thirty years later then I, quite frankly, am not going to invest in you. In fact, I’m going to probably run away as fast as possible.

So the experience needs to be timely, it needs to be relevant, it needs to be “now.”

Take the positives from the negative experiences so that you learn from them and become better, faster, stronger, as a result.

Aaron Webber is a serial entrepreneur and CEO of Webber Investments LLC, as well as a Managing Partner at Madison Wall Agencies.

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Aaron Webber

Aaron Webber

Chairman and CEO, Webber Investments. Partner at Idea Booth/BGO.