Billy Ryan Billy Ryan

Building Unicorns & World Series Championships

I spent 15 years in Major League Baseball evaluating talent, negotiating contracts, and building teams on & off the field; all toward one goal: winning the World Series. When I pivoted away from sports, I entered the dynamic and frenzied world of startups, joining an early-stage company that two years later earned a $1B valuation and officially became a Unicorn. Both environments were fast, furious, competitive, and fun. Here are some of the parallels of, and lessons learned from those two experiences:

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Is Ego the Enemy?

If left unchecked, ego can spell the demise of careers, relationships, even entire empires. It's been the driving force behind scandal, war, treason, and murder, to name a few.

Then again...ever meet a really successful person who has no ego at all? …anyone who's ever been really good at something definitely has an ego. In some sense, they have to in order to be driven to do great things.

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The Compounding Effect of a Self-Policing Culture

Everyone wants passive income, right? Mailbox money. You put in some work up front, lay the foundation to create cash flow, then kick back and reap the rewards.

In the world of leadership, there is a similar opportunity to build a self-sustaining, perpetual cycle of value: the self-policing culture.

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Treat Every Day Like Opening Day

We love new beginnings. The rejuvenation, the optimism, the seductive uncertainty of what the day may bring. "This could be our year." Well, today could be your day. Embrace it with the same enthusiasm.

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How to Be More Like George

He was also an accomplished general, skilled statesman, and national hero, but what made him great in the moment--not in hindsight and through the lens of history--was the manner in which Washington carried himself. The kind of person he was. He was admired by both rivals and supporters for being forthright, honest, respectful, and sober. He was a humble man of moderation, with sound judgement and highly-tuned emotional intelligence, reading people brilliantly in both his personal and political life.

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They're Not Your Cleats to Hang Up

Everyone is entitled to their opinion. I'm sure your colleagues have opinions about you. Doesn't mean you're going to listen to them, does it? You know what is right for you, not them. It's your pillow you need to lay your head on at the end of the day, not theirs. Same goes for professional athletes. We all get one trip around this merry-go-round. Who am I to tell someone else when to get off? 

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Why I Read, What I Read

I wasn’t a big reader as a kid. I was a good student and diligent worker, but never much of a pleasure reader. I more or less viewed reading as a means to an end. If there was something specific I needed to know, or a school assignment I had to prepare for, sure, I’d read. But, outside of that, reading wasn’t high on my list of things to do in my free time.

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Please Tell Me No

Ever see those contestants on American Idol who clearly didn’t have that person telling them no? Or heard the stories of the athlete or celebrity who gets real rich, real fast, only to lose it all a few years later because they had a bunch of people telling them what they want to hear instead of what they need to hear? Maybe you’ve encountered a parent or two who has trouble telling their kid no. They’re not doing them any favors.

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Paul Goldschmidt, Bias, & Betting on People

Paul Goldschmidt is as humble and grounded a superstar as you will meet. He leads by example, with remarkable consistency. He is the baseball equivalent of a self-made, grinding entrepreneur. Showing up, day after day, getting a little bit better each time, and before you know it, you have something special.

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Letter to My Unborn Son

Parenting is incredibly hard. Anyone who has done it knows it is all-consuming, requires a wealth of patience, and can leave you exasperated. It’s also the most important and rewarding job in the world, bar none. There is no handbook, no shortcuts, no hacks. You have to put in the work, the time, and the love. And you’re still going to screw up.

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Pray Your Way to Leadership?

By humbly appealing to a higher power for wisdom, forgiveness, strength, or patience, we acknowledge that we’re lacking it. That self-awareness, humility, and desire to do good is ultimately what can form the foundation for greatness down the road.

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Quiet Quitting is Nothing New

The term “Quiet Quitting” is getting a lot of attention right now, but it’s not a new phenomenon. Sure, the cultural and environmental shift that has taken place since the pandemic has changed the game a little, but the rules have always been the same: if you don’t understand, value, and engage your people on a meaningful level, they’re as good as gone.

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Let the Kids Play

That guy you’re berating in front of a bunch of kids and neighbors? He’s a volunteer. He doesn’t need your crap. Do you think your kids are going to remember the bad call in the 3rd inning or the awesome snack after the game? Think your son is going to show that 9U football trophy to his grandkids someday? No, you’re behaving the way you are because YOU feel slighted. Because YOU feel disrespected or cheated. Because you think YOU deserve better.

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Quantifying Emotional Intelligence

We tend to overvalue what we can quantify. It’s human nature. Certainty is comfortable, so confronting any element of uncertainty can be uncomfortable. It’s eases our anxiety when we can point to cold, hard data to justify our actions. It’s a lot scarier to walk the decision highwire based on your instinct and experience alone, without that data safety net beneath you. The trap there is that while it’s easy to place a value on what we can quantify, not everything we can quantify is valuable.

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What’s the worst that could happen?

If we only picture good things happening, how can we expect ourselves to respond adeptly when bad things happen? Preparing for success doesn’t mean diluting yourself into thinking you’re invincible. On the contrary. It means knowing—no matter how good you are—that you’re fallible. And that no matter how destined for success you may appear, fate is waiting right around the corner with a devilish grin. So we should prepare for that—visualize it—and focus specifically on what you will do and how you will overcome.

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Help Control the G.O.A.T. Population

We need heroes. Icons. Legends. Something to hold up above all others. And if we still need that aspirational archetype, then we need to defend that level of excellence with vigor. If everyone is great, no one is great. If everything is important, nothing is important. We need things to be important. So let’s honor those who are appropriately, and exclusively.

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Mr. Rogers and Empathetic Leadership

Fred Rogers led what amounts to a cultural revolution among parents and kids not by asserting his by power or authority, but rather by leaning in with empathy and authenticity.

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A Vote Against Multi-Tasking

Look, technology is wonderful. So many of our daily tasks have become automated. Advancements in the field have made our lives exponentially easier in countless ways. But has it made things too easy? Are we conditioning ourselves for short attention spans, poor memories, and an inability to relate to each other?

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