Greatness is to be expected or you’re doing it wrong

“Is there a Top 25 team that doesn’t have a DeMatha player on it?”ESPN Announcer

My startup Speek is fixing crappy conference calls. We recently raised a large seed round of funding and we went about building out our full-time staff. This was a key undertaking, as every hire was critical to improving or degrading the natural culture the company had already started forming. As we went through this process, I couldn’t help but think back to examples of great cultures to which I had been exposed.

I went to DeMatha High School in Hyattsville, Maryland, and I also attended Harvard later on in life. I am most proud of my experience at DeMatha. You see, DeMatha has figured out how to instill in its student body the expectation of greatness. Winning wasn’t just a nice bonus—it was expected.

I remember making the varsity baseball team as a sophomore (which was rare) and feeling extraordinary pressure—pressure like I had never felt before in a lifetime of playing sports that already included stints on multiple state championship teams—to win the championship.

I lived in Centreville, Virginia and wasn’t old enough to drive, so I took the bus to the commuter train, the commuter train to Union Station in D.C., the metro to PG Plaza in Prince George’s County, Maryland, then walked the mile or so from PG Plaza to DeMatha carrying my books and baseball gear. Soon the Filson family, whose son Greg was a star on the baseball team, were kind enough to let me live with them during the week at their house in Bowie, Maryland.

It’s funny; looking back at that commute and at living away from home for so long, it sounds really hard even as I type it. It wasn’t. I wanted to be a part of whatever DeMatha had going on. It drew me in like the crack did to Pookie. No one ever said,“Man, I really hope we win it all this year,”because nobody needed to say it: it was expected. Anything less than winning it all was a failure. An embarrassment.

At DeMatha All-Americans, Merit Scholars, and nationally recognized musicians—prodigies of athletics, academics, music, and sometimes all of the above surrounded you. You heard about championships being won, awards being earned, scholarships being signed on the loud speakers every day between the Pledge of Allegiance and the Lord’s Prayer. You were great at something; anything, or you were shit and didn’t belong there (my words not theirs).

We consistently outperformed other schools in athletics, academics, music, drama—you name it. My graduating class had fewer than 200 kids, but a hefty majority of those kids were great at at least one thing. We had several basketball, football, baseball and lacrosse players who went on to play at the professional level—11 football players alone got division 1 scholarships. There was an astounding rate of graduates that matriculated to Ivy League colleges or military academies.

To give you an idea, here is a breakdown of just the sport teams’ championships over the last few decades:

Basketball 34

Baseball 24

Wrestling 23

Football 19

Lacrosse 17

Golf 14

Track 12

Hockey 10

Tennis 10

Soccer 8

If you weren’t great—if you didn’t win—at DeMatha you didn’t fit in.

It was literally embarrassing to NOT get good grades, not be a leader, not win a championship, not score the highest on standardized tests. Outcasts at DeMatha were the students who did not achieve greatness.

This expectation of excellence not only applied to students but also to teachers. DeMatha retains the best teachers around. Most of the teachers I had while at DeMatha had been there for decades and were masters of their craft. The younger teachers were expected to get great quickly or find their way to the door. The few bad teachers I had were brand new and tended to be gone the next year.

I recently read a book about Apple’s management style and culture and it reminded me of my time at DeMatha. Apple doesn’t do a lot of the typical corporate“make everyone happy”bullshit where committees and politics are part of the decision-making process. Teams and leaders are expected to be great and win with their products or they don’t last long. It must be incredibly embarrassing to be working on something at Apple that doesn’t win its market. There is fierce competition within Apple, not for promotions and position, but to work on a product that is successful, and to meaningfully contribute to that success.

The author relayed how teams didn’t have transparency into what other groups within the company were working on—which is both rare and genius, in that it completely eliminates the typical corporate political maneuvering—but they sure as hell were privy to Steve Jobs announcing a winner on stage for the world to see. I bet they also sure as shit read about the wins of their peers and/or competitors.

At a base level, this may not sound entirely revolutionary, but it is. Committee has besmirched corporate culture with too much transparency, too much groupthink, and too much death. When success is not achieved, the fault is seen to lie with everyone, not one person or a small team. There are many rocks to hide under. This does not work.

Creating a culture where greatness is expected is a difficult act. I am still not sure how DeMatha did it. I never heard the school administrators giving talks about greatness. I never got memos or letters under the subject “Re: Winning.” There were no consultants engaged to make us great at winning. We just went out and won. Instead, greatness was intrinsic to the culture. It was not a conscious decision; it just was.

I don’t how to explicitly apply these lessons learned from attending DeMatha or studying Apple to my own startup. I suppose one way is to cast an implicit expectation of greatness on every single employee of Speek. When we do things, we do them well. We don’t fail. If we do an experiment or try something out, we define expectations ahead of time and we measure and learn. When we double down or go all in, we win. You have to be great at lots of things to work here. You have to think differently than the 9-to-5 corporate shlubs out there. Hard work is expected and never bragged about. Politics and posturing are not tolerated. Measurable results trump all. I think these are a few good places to start. The overall take away that I apply is that great people want to be immersed in greatness. “A players” want to work with “A players” and “B players” want to hire “C players” so they keep looking good. Greatness begets greatness and that’s a great place to start.

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