How It Started ... How It’s Going

“I must not fear. Fear is the mind-killer. Fear is the little-death that brings total obliteration. I will face my fear. I will permit it to pass over me and through me. And when it has gone past, I will turn the inner eye to see its path. Where the fear has gone, there will be nothing. Only I will remain.” ~Frank Herbert, Dune

Last week, I was blessed with the opportunity to speak as a member of Amherst’s Alumni-in-Residence program. It’s ironic because I have always had a conflicting relationship with Amherst, one that endured and was unresolved for a long time—I loved Amherst, but consistently felt isolated. I struggled throughout my time there with being a Black man, and sometimes the athletic experiences reinforced that feeling of isolation. Even as a double major and two sport athlete, the consistent self-damning question of “Do I belong here,” ran rampant in my mind. While there are many stories from my time at Amherst, one major event was getting benched my senior year; more importantly, how that forged an incredible friendship with my good friend, Andrew Reed. I spoke about our relationship throughout the (ZOOM) fireside chat for the Alumni-in-Residence program.

How It Started…

Let me take you back to Sat, Oct 14th, 2006 on the Hilltop. A night game, the Hackley Hornets (4-0) against the Brunswick Bruins (4-0). I was the starting quarterback for Hackley, and the Reed twins (Andrew and Will) were two dominant receivers on a stacked wide receiving core for Brunswick. We were fresh off a solid win against Horace Mann. Brunswick was sure to be our fiercest competition to date—we would have to play a perfect game to beat them. For Brunswick, it was just another game. I, however, had anticipated this night for weeks; the previous year we lost 36-0 at Brunswick in a game that I’ll always remember for two reasons. One, there was a light rain. I remember looking over at their quarterback, Kevin Decker, pre-game; he was dunking footballs in a bucket of water before throwing tight spirals to his coach. I was rattled by his skill. Second was halftime; ask Larkin about Coach Negron, he’ll have a story for you. We got off to a fast start, moving the ball swiftly down the field. Nonetheless, by our third offensive drive, as we got to the line of scrimmage, their linebackers called out our plays and named the routes the receivers were going to run…This was the last game of my high school career. In the third quarter I was tackled from the blindside, helmet to helmet, leaving me concussed. A couple weeks later the neurologist told me that I had a choice to make; I could finish my high school football career and risk potentially getting another concussion, ending my football career indefinitely, or I could sit out and wait for Amherst where I’d committed to play for another four years. It was a really difficult decision, but I chose the latter. I’m glad I did.

A couple years later, at Amherst, I reconnected with Andrew (and Will) as they brought their talents to Pratt Field. I earned a spot at wide receiver, but I was close to getting cut my sophomore year. I knew our Wide Receivers Coach Laf, wanted Andrew to play as a freshman, but Andrew had nagging ankle injuries after recovering from his compound ankle fracture (the same injury Dak Prescott—the Dallas Cowboys Quarterback—suffered weeks ago) during his senior year in high school. I trained hard, and through grit, persistence, injuries, and a bit of luck, I earned playing time as a sophomore. I scored a touchdown in my first game against Hamilton, a 33-yard post, paving the way for me to start the second half of the season. As a junior, I played more than any other receiver on an undefeated, NESCAC Winning championship team. And my senior year, I was benched. Having abandoned my identity as a quarterback even before I made the team, having nearly been cut, and then being benched, I had more questions than I had answers about who I was, as well as about my athletic prowess given I had been recruited to play football.

I could write a book on the mental toll getting benched had on me. Realizing someone else’s “best” is better than mine and losing the spot to a friend was incredibly humbling, but it was a season that forever changed my life. Though Andrew handled the switch with class, it was a difficult transition for me. We were always friends; however, I saw him getting the repetitions that I used to get, making plays, and doing all the things I knew I could do. Regardless, it was no longer me. My envy grew, both fueling and crippling me. Physically, I played well and with confidence. Mentally, however, it was tough to block out the feelings of insecurity, resentment, and fear that my senior season would not have the storybook ending I had imagined, filled with touchdowns, celebrations, and a second straight NESCAC crown. This led to further conversations with my mentor and friend, Pastor Grant, who so often offered sound advice throughout my internal struggle:

“And think of this in terms of your relationship with Andrew Reed—a year younger than you, a junior, a good friend of yours. You are a year older, more experienced, a senior. Suppose your problem with what’s happening were to become a new project, like helping him be the best wide receiver he can be, by being yourself; the best receiver you can be, and in the process, even in the midst of the competition, being the best friend you can be, with all that means. You would win, he would win, the team would win. And you would be the Sean Legister you truly are...This may be starting out not to be the senior year you had in mind, but it could in fact be the senior year to remember, the one in which you learned more about yourself, more about experiences, more about life, more about what it is to be a man, than all you’ve learned before. The college diploma doesn’t say that in so many words, but in truth, that is what this is all about.”

The first game of my senior year we routed Bates 44-0. Andrew started and had himself a hell of a game. After his touchdown on Rocky Shake Hot, he ran to the sidelines and gave me a hug. He looked me in the eye and said, “That could have easily been you.” Those words touched me deeply. As a true friend, he showed an understanding. It would have been very easy for him to stop being so friendly after he beat me out, and he could have even started to believe his own hype. But instead he showed true character and a warm heart. He is not a good friend, but a great one.

…

How It’s Going…

November 2019, Coach Laf (still my friend to this day) invited me to speak to his football team, Trinity-Pawling. It was a night I will never forget. We were sitting in a classroom and I was trying to engage with a bunch of high school students. The last thing they wanted to do on a Friday night was hear some washed-up dude talk about his college glory days. Yet, while telling them about my time at Amherst, a student asked Coach Laf why I got benched. Though initially saved by someone needing his assistance in another room, when Laf did come back, he told his side of the story. He asked, “Was Andrew catching the ball a little better than you?” I said, “Yes.” “Was Andrew a little faster than you?” I said, “Yes.” He went on to explain how Coach Stick (the Offensive Coordinator during my time at Amherst) suggested that Laf didn’t need to bench me. But Laf did anyway. My heart sank. All the emotion from nine years prior came rushing back. As the saying goes, “The truth will set you free, but first it will piss you off.” To finally hear the truth was gut-wrenching, especially given that for so long I thought it was Stick’s decision to bench me.

While I still struggle to find words to deftly describe exactly how I felt in that moment, the most telling part of the evening happened when I got back to Laf’s house. I crawled into bed and saw a text from Andrew. He wanted to connect me with someone that had asked about me at his wedding (Sept 2019). Seriously. The night I found out why I was benched nine years earlier was the same night that Andrew, who beat me out, sent me a text about a potential private equity opportunity in LA.

Andrew’s text enabled me to meet multiple people as I began to learn more about private equity. It opened the aperture, exposing me to alternative career paths that augment my skill set and add new texture to my experience. In many ways, it helped me secure the position I have today. Yet, what’s ironic is that at Andrew’s wedding, Andre (another groomsman, another Amherst receiver, my college roommate, my confidant) and I stayed up till the wee hours of the morning talking about life. We were going down deep rabbit holes of conversations that we had overheard at the wedding. We discussed how special that night was. We also reminisced about the bachelor party in Hawaii—one night ended similarly; six close friends, talking about everything, crying while sitting around a fire. I vividly remember talking about “carried interest,” though at the time we didn’t understand its definition. Dre commented that I’d be unstoppable if I continued to build my financial acumen and number sense. Andrew and Will are very successful in venture capital. They had mentioned “carry” a handful of times in Hawaii; Andre and I were up trying to make sense of what it all meant and better ourselves…

Now, Andrew is the youngest General Partner in Sequoia’s history. I’m a new entrant to private markets, more specifically within the fundraising realm of private equity. Recently, I connected with Andrew about the anxiety I was having in my new seat, and we commiserated on it all. It’s easy to see his title and think that his life is great without understanding the gravity and stress associated with his responsibilities. And even though we’re no longer on the football field, we’re still teammates. He’s still beating me out, but similar to Pastor Grant’s wisdom—Andrew is helping me grow stronger than ever before.

Breakfast Bites is something that has quelled my anxiety. I realize that I’m playing for a larger team. A couple months ago, when talking to Andrew about Breakfast Bites, he introduced me to Trevor McFredries, the Co-Founder of Brud who is changing the world in his own right. I was ecstatic to host Trevor at Breakfast Bites and learn his story. I’m also so happy to announce that Andrew will be one of our year-end speakers at Breakfast Bites—I chuckled when he asked me if he was qualified to speak…

As has been written in other blog posts and said many times, you can only connect the dots looking back. I never could have imagined that that one night on the Hilltop would lead to a deep friendship that has spanned years (one so symbiotic and growth oriented, no less). I would often stop by Andrew’s office whenever I was traveling to see clients in SF just to pick his brain, learn how he was fairing, and siphon any wisdom I could from his experience in venture capital. And now, he’s connecting me to people in his network as I continue to develop my private markets game.

I’ve learned a lot from Andrew. His intellectual humility, his laid-back demeanor (when he and Will aren’t going at it), his understated confidence, his resilience, and his persistence are uncanny. He’s one of the smartest people I know, yet he’s always willing to learn more. Note, he’s also always good for some random fact that no one cares about but will laugh his corny laugh and that’s just him!

I mentioned earlier that I had a complicated relationship with Amherst. Yet, it’s Amherst Football that links me with three incredible Andrews: Andrew Reed, Andrew Dorogi (another #22), and Andrew Grant (Pastor Grant’s son). All three men have changed my life. Rue is the one that I’ve known the longest and the one who’s counsel and consistent contact continues to challenge me. 

All these moments haven’t had a linear path, but it suggests that building real relationships far outweighs getting caught up in ego and emotion, particularly when things don’t initially go your way. Andrew and his team ended my career years ago, but he and his new team have helped me start a new one, in a realm where the endzone is worth so much more than six points and I’ll be a much better athlete. That’s how I see it going…

*Note* This piece speaks solely to my insecurities and my perception…When I spoke to Andrew about some of this last September, he commented, “Also—worth saying—I never actually thought I ‘took your spot’ for one—but more importantly I still think of you as the big brother who took a skinny nerdy kid under his wing freshman year and helped me grow up and grow into myself and be myself.”

Bafana Bafana,

Sean