More Than a Game

95% of Fortune 500 CEOs have this in common...

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🏆Youth Sports: A Competitive Advantage

Books and balls. As a kid, it was rare to find me without one of these two in hand. While appreciative of solo sports like singles tennis and golf, early on I found myself gravitating towards team sports such as basketball and soccer. I stuck with these two throughout my childhood and high school days, but ultimately my love for learning took over and I began to focus on a different sport. Business. Often referred to as the sport of money, business is a lot more than that. It’s a sport of people, innovation, psychology and systems.

How people act in sports is often a fair indication of how they’ll act in life and business. If you cheat on the court, you are more likely to cheat in your relationships. If you cut corners in practice, you’ll look for these shortcuts in your professional life too. I see no coincidence that many of my worst childhood teammates who were seemingly allergic to passing the ball grew up to be egotistical, attention-seeking jerks.

Luckily, I’ve had significantly more amazing teammates than cancerous ones, and credit much of my athletic experiences in shaping my approach towards business. Here are a few of my biggest takeaways:

How to Prepare - Success is like an iceberg. Most people only see the tip and fail to acknowledge the amount of mass under the surface, the same way they ignore the amount of work and preparation required to reach the peak. Sports strongly and correctly enforces the narrative that without practice and preparation, it’s impossible to win.

How to Work as a Team - No matter the amount of talent or time spent practicing, it’s impossible for a team to achieve greatness without working together. This means playing your designated role, showing humility, and making sacrifices for the greater good of the organization. Most importantly, it means communicating effectively. A football team whose offense and defense practice and operate independently will never win a Super Bowl, so why do the departments of many businesses’ operate in silos?

If a company is truly dedicated to a mission bigger than itself, there’s no reason to hide finances, marketing initiatives, or R&D advancements from the bulk of the organization. The seamless and transparent sharing of information between teams streamlines decision making, removes bottlenecks, and creates a culture of openness and honesty. All of these improve employee productivity (read team output) and directly affect the bottom line. This is a competitive advantage that many companies fail to acknowledge.

How to Compete and Defend - Playing sports sparks a competitive fire that no other activity can replicate. You learn how to win, but more importantly how bad it feels to lose. The idea of loss aversion, a tendency to prefer avoiding losses over acquiring equivalent gains, rings true here. Once you lose, especially when on the cusp of victory, you never want to lose again.

It’s often said defense wins championships. Others say that the best defense is a good offense. This is especially true in business. Unlike sports, not only do you need to worry about your current competitors, but also your future ones too. If you let your guard down even for a second, these new entrants can quickly steal your customers before you have a chance to get a play off. To survive this competitive battleground, you need to constantly innovate (offense) where your competitors aren’t. By building a moat through innovation, you defend against losing your market share. In this case, innovation is the best defense.

These are only three of the countless business lessons I’ve learned from sports. The ability to act under pressure, courage, persistence and drive are other notable mentions.

Fun Fact: 95% of Fortune 500 CEOs played sports.

What other business lessons have youth sports taught you? Let me know by replying to this email, shooting me a DM on Twitter, or leaving a comment below.

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👑The VIP Treatment

Want to know the best way to win someone over to your way of thinking? Make them feel special.

Humans are naturally egotistical, and even the most self-aware individuals have trouble resisting personal courting and the feeling of VIP treatment. I want to share with you a cold email sales tactic I came across while listening to this episode of My First Million.

This was initially used by popular corporate startup card Brex and most recently by Shaan Puri’s fund to close over $500,000 of investment capital in two days. It was also enough to get me to say “holy shit” way too loudly while waiting on line at my local bagel shop. This resulted in many confused stares from customers and store employees alike, thinking I was overly-excited about the new batch of cream cheese that had simultaneously been replaced in the counter window. Tough break.

Anyways, here it is:

You have a sales agent who writes an email to a client. The email says something like this:

This is brilliant for a few reasons:

  • An approach like this makes the recipients of the email feel special, as if they were hand-picked. Who doesn’t want to be on the accelerated rewards list or at least hear what it entails?

  • It’s one thing to say that this was a request from the Chief Sales Officer, but it’s another to attach the actual email. This makes the recipients feel like they’re getting an inside look and eliminates any cold email, spammy feeling. Personalization at it’s finest, the complete opposite of a boilerplate email template.

  • It’s short, sweet, and friendly. No sales talk or lengthy pitches. Value prop is clearly communicated in one sentence.

Here’s how Shaan modified it for his All Access Fund:

The modifications here are endless, but the more personalization the better. I can’t wait to give this a shot.

🧰Tool of the Week

After listening to your feedback, it seems like many of you are either current founders or plan to start a business in the future. Regardless of where you are in the entrepreneurial process, The Founder Library is a valuable resource. Created by entrepreneur coach and angel investor Steve Schlafman, the Founder Library has hours worth of content to help you navigate through any part of the startup journey.

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If you’re new here and want to catch up on some old editions and interviews, here are a couple of my favorites: The Art of Getting Lucky and Friday Features: Gaby Goldberg. You can also follow me on Twitter or check out for more writing.

Thanks for reading,