Interview #30: A Long Island Geography Lesson
Gary Sommers, entrepreneur turned soccer coach
Intro
The drive to succeed is often times equal to the need to succeed.
I’ve known Gary Sommers for over a decade now. He joined my hockey team right after I did in 2012 and played 20+ seasons before retiring to the D league last winter. He’s a lifelong New Yorker from Long Island and lived in the tri-state area until he moved to the warmer weather of Scottsdale about 15 years ago.
Besides introducing me to dozens of new areas in New York City, he also went in to what made him successful in his career that enabled him to retire from full-time work at a young age. And also how he was able to shift gears from a businessman pulling long hours to a family man coaching youth soccer teams. It was an interesting perspective, since most successful people you meet or read about, their whole identity is tied up in their wealth and career, to the detriment of family life, health and, well society as a whole suffers from corporate greed. Gary did what he set out to do, accomplished his goals and then moved to the next phase of his life.
That phase includes adult hockey and lots of ski trips. I’d take that over a corner office in the C-Suite any day (although right now, any good-paying job would be nice). I only knew Gary after his 50th birthday, so some of his competitive nature he talked about was news to me. He’s the most level-headed, calm player I’ve ever had on the team I captain, so much so that if I ever needed help getting someone else under control, I’d go to him. Then he retired and our team went 3-17 the next season. :(
Also, he’s a pretty well-rounded sports fan. I think he’s into the Jets first, but they’re never worth talking about, so then he’s got the Islanders and Yankees. Also it sounds like he could’ve been a pretty decent baseball player, but since he couldn’t play the fun infield positions and didn’t want to play the outfield, he retired to a soccer career that did pretty well for him in the long run.
Graig gets a New York geography lesson
You grew up on Long Island?
I grew up in Commack, so I spent most of my years on Long Island ‘til I went to college. After college, I spent a little bit of time in Queens, then back to Long Island, then up to Westchester where I bought my house.
Where is Westchester?
Westchester is an hour north of Manhattan.
So Staten Island's where you grew up-
No, Long Island, which is different.
I need to pull up a map.
Long Island is east of Brooklyn and Queens. Staten Island is part of the five boroughs of New York, and Long Island is like a suburb. The Yankees play in the Bronx, and the Mets play in Queens.
So Long Island is this big-ass island over here. Where’s Staten Island?
It’s on the other side of New York.
There’s an island over there?
They call it Staten Island.
I ended up in Newark, that's not right. Is it east or west of the Hudson River?
No, it's down. More toward the New Jersey side.
Ah Staten Island Zoo! Wait, that’s not an island.
Technically, it is. It's the least known borough of New York City.
OK, wait, now that I know this stuff, let's get this straight. So you started on Long Island. What part of… there's a lot of Long Island. It’s 80 to 90 miles long.
Right. So I grew up in a place called Commack.
So what's the commute to get from Long Island into the city?
You take the Long Island Railroad. So the Long Island Railroad goes into Penn Station.
You must think I’m an idiot.
No, no. You’re not from there. So the Long Island Railroad goes into Penn Station. Where I lived in Westchester, you take something called Metro North, and Metro North goes into Grand Central Terminal. So there are two main train stations in Manhattan. And then there's subway trains to get you around. Yankee Stadium, from where I lived in Westchester, is easy because there's a train station right at Yankee Stadium. But to go from Long Island to Yankee Stadium is a big pain in the neck because you got to go into Manhattan and then take a train up.
What about Shea?
Shea you would drive to. There's probably a Long Island Railroad station not too far away. We didn't go to a lot of games. My dad wasn't a big fan. When I was a kid, if you had milk cartons, they would have little stamps on the milk carton and if people collected enough stamps you could get free tickets. So at least once a year the Boy Scouts would collect these things and you'd get a free ticket to the game. And you would sit in the top deck in the last seat of the worst section, and that's what they would give away to the Cub Scouts and Boy Scouts. But I do remember being a kid, my grandfather was a pretty big baseball fan, so he would occasionally get tickets, and him and I would go down to Yankee Stadium.
Did you guys go to football games a lot?
No, because all those things were expensive. We didn't have a lot of money growing up. I do remember one time my dad took me to a Jets game. It was a totally miserable Sunday, terrible, rain, cold, disgusting. And our neighbor was a season ticket holder. So he just decided, this is absolutely miserable, I'm just not going today and the Jets were not good back then anyhow. So he gave the tickets to my dad and my dad was like hey, let's go to the game. I was a little kid and my dad kept saying, have you seen enough? You wanna go? I’d be like no, no, let’s stay. My dad stuck it out with me the whole game, so that was fun.
Okay, the New York metro area has like 100 cities in an area half the size of the Phoenix valley which has like, 10. They need to merge themselves so it’s easier for idiots like me to find my way around. I knew it was called Long Island, I didn’t realize Long Island was actually that long, though. It has more area than the state of Rhode Island.
A left-handed shortstop turned soccer goalie
Did you play baseball?
I did. I started off in Little League and played until middle school. And then I arrived into majors, which was the highest level before juniors and seniors. My coach said, you got to move off of shortstop. And I was like, why? You're a lefty and lefties don't play shortstop.
Did you play other sports?
I started playing soccer in middle school and I played goalie. I was actually pretty good at it, so I played in middle school for two years, and then I played in high school for three years. The last two years, our team won our conference championship.
I played soccer all they way up into college. It was pretty fun, you’d get recruited and get coaches calling you and letters in the mail. Nothing like it is now, but it was pretty cool being 17 years old and having coaches call you up at home and try and get you to come to their schools.
Soccer wasn’t as big back then though, was it?
Soccer wasn't super big in the rest of the country, but on Long Island it was actually a big sport. They had the North American Soccer League (from 1968-1985) and I think at the time, 5 out of the 20 goalies in the NASL were from Long Island. I was only 5’9”, which I didn't realize was too short to actually play real soccer. I was good, but when you get into college, you realize being 5’9” and good is not the same as being 6’3” and good.
How did you wind up the goalie?
I couldn't play forward.
And then you played in college. Were you starting?
Back then, freshmen were ineligible to play. So when I went to school at University of Pennsylvania, I started on the freshman soccer team at Penn all year. Then when I became a sophomore, I was eligible to play varsity, but they had a 6’3” senior who was playing and they had a guy who was a junior who was bigger than me. It was the first time in my life I ever saw anyone who was a better goalie than me. It was kind of that epiphany of, ‘Wow, he's bigger than me, he's fast, he's really good. I can't really compete with him.’ So that was kind of the end of me playing.
But you stayed at that school.
Yeah, I stayed at Penn for four years; they had a great business school. In the Ivy League schools, they don't give you scholarships. They give grant money. So I got accepted into Penn, I got accepted into Albany, and a couple of other schools, and my dad was able to call up the soccer coach and say, he can't come unless I get more grant money. And the soccer coach worked whatever magic they do and I got a ton of grant money to go to Penn.
There were a couple of other places I applied to. I think being a good soccer player really helped. At one point, we were at this all-county All-Star thing, and at the time I didn't even think about it, but the guy who was there from Yale came up to me, goes, ‘Oh, if you want to come to Yale, let me know, I'll get you in the college.’ And I was like, ‘I don’t want to get go to Yale.’
You didn't want to go to Yale?
I didn't understand the opportunity really, but I was like, no, I don't wanna do that.
I also turned down an education at Yale. I was already accepted to the Harvard of the West, so it would’ve been a step down. Also, he was talking about playing shortstop and for the whole 15 minutes I forgot he’s a lefty. So when we got to him quitting baseball it was because there’s no such thing as a left-handed shortstop. I know there’s plenty of reasons why, but I wonder how much slower a lefty shortstop actually would be in terms of fielding and throwing with their back to the plate. Turning two at the bag would be smoother though. Maybe someone (ahem, Oakland) who isn’t trying to win this season should experiment.
Putting that Penn education to good use
So when you graduated, what then?
My first job was with a company called Anderson Consulting, which is now known as Accenture. So I worked in their consulting division for a couple of years. I didn't really like it, I didn’t want to work for a big company. But back in the 80s, the economy was really bad. The 80s economy makes every economy since look good. The 80s was when New York was a pit.
Did you live in New York City in the 80s?
I was working in New York, but I was on the road a lot. I rented a house with four of my buddies from college in Queens. We rented this beautiful Tudor house, it was gorgeous, and the owner rented it to five college guys, which was super ridiculous.
The best thing that came out of Anderson Consulting is I met my eventual business partner on one of my assignments. I left to join a small software company with this guy. That company did really, really well and we eventually were able to sell it, which was great to have some cash in the bank. Then I did some consulting for our clients for a couple of years and that got kind of boring. So we decided we wanted to start another company. We built the same kind of software, but in a different technology environment. I worked with him and his wife and another guy and we built that company up and that one did great and we were able to sell that one as well. So the best thing that came out of Anderson Consulting was meeting my eventual partner, Mike.
How long did you live in Queens?
Probably for two years. And then I got married and we bought a co-op in a place called Bellmore, which is in Nassau County.
So you're back on Staten Island?
Long Island.
Dang it.
So one of the things when you work in a small company, the good thing is you have a lot of say in what you do and where you go. So I told Mike, I'm not tied to New York, I'll go work anywhere as long as Eudora can come with me. So we got to live in London for a year. I lived in Toronto for a while. I lived in Australia for a while. I got to see the world while doing projects for these big banks.
And then once we started having kids, it was sort of the same thing. I told Mike, ‘I'll go anywhere,’ but now it's 3 plane tickets and then 4 plane tickets. So when we lived in London, my two daughters came with me and Eudora and we rented a nice house. Eventually, we settled back on Long Island when my oldest daughter got to be in first grade.
For a while, I was commuting from Nassau County into the city and then you take the subway and the PATH train to get to Jersey City. But I had a pretty nice consulting gig and I had a bunch of people working for me, so the money was good, the commute was awful, but when you got three kids, money is important.
When we decided to start the second company, my three partners all lived in Westchester and I was on Long Island. So we started the company in Manhattan.
(looking at Google maps again) I've got Westchester. Isn't that in the Bronx? Oh, wait, sorry, that’s Westchester Square.
Westchester is north of the Bronx. You’re getting a whole geography lesson. Bronx is north of Manhattan and Westchester is north of the Bronx. Bronxville, Eastchester, Yonkers, where my grandparents grew up, by the way. Pleasantville was where my partners lived. Chappaqua is where Bill Clinton lived after he was president. And then we lived up in Bedford Hills/Katonah. So it's only 30 minutes basically from lower to upper Westchester, you just take the highway straight up.
Once we started the second company, our first office was in Manhattan, and then as the company grew, Manhattan real estate was just super expensive. So we decided to move the company from Manhattan to Westchester. But the traffic on Long Island is ridiculous, so then I moved up to Westchester and that's where we lived for 18 years.
When you were living there, did your kids get into sports?
All my kids played soccer. They all played goal at some point.
They all played goalie? It was in their genes?
I don't know why. My oldest daughter played for a couple of years and gave it up. My middle daughter played more years and she played more in the field than in goal. My son played lots of years, he played all the way up through high school and he played in the field and in goal. He was in travel soccer, but as he got older and got into middle school and high school, he wound up being a goalkeeper. And it was good because I was able to teach him a lot about the sport.
His senior year of high school, he wound up being on an all-Middle Atlantic All Star team, so he was pretty good, too. He also wound up going to Penn, but by now, sports in college was off the hook, it was like on steroids. When I played, you got to go to school a week early, you went to training camp. At the end of the season, the coach would literally be like, ‘Hey, don't get fat. See you in September.’
Now, you're at school in August for a month, you're training, and then the season ends, you get a day or two off, and then you're back in the weight room and playing. Playing sports in college now, it’s way different than when I played. When I played it was just something to do and now it's a full time occupation in addition to being a student.
How did that “full-time” aspect compare to when you grew up?
By the time I had kids, sports got to be really organized. So my kids did not grow up going to the schoolyard and hacking around with their friends. They grew up playing Little League Baseball, which is organized, peewee soccer, which was organized, travel soccer, which was organized. From me being a kid to them being a kid, that’s sort of when everybody was like, you can't let your kids out alone. You can't let your kid ride a bike. They're going to be kidnapped and stolen and put in a van and you'll never see them again.
When I was a kid, you'd get home from school, put your stuff away and you'd go down to the schoolyard and kids would just play. And the rule people my age always think about is when the street lamps come on you have to go home. But when I was a kid, even after dinner, a bunch of us would just go out at night and we would just play ringolevio, all sorts of crazy games in the dark in the street and nobody thought anything about it. But kids got really regulated because nobody wanted their kids to be out doing anything on their own.
Were you one of those parents?
There was nobody (for them) to go out with. There was no just being a kid anymore. Everything changed, and I don't know if it was with society or what it was, but my wife will say the same thing. When she was a kid, on the weekends, you'd wake up, you'd have breakfast, and your mom and dad would be like, ‘See you later.’ You’d just go out. Nobody had a water bottle. Nobody wore a helmet. Nobody had knee pads. If you got thirsty, you’d drink out of your neighbor’s hose.
You goofed around all day long doing whatever and then you came home when the street lamps came on and had dinner. There were no video games, there was hardly any TV channels. So life was just a lot different because you either watch the 5 channels on TV and nothing was on, or you could just go out and play. It was completely unstructured, people would actually go out and ring people's doorbells and be like, ‘Hey, we're playing football, do you wanna come out and play?’ There was not this whole idea of playdates and everything else.
So your son is into sports?
Yeah.
Did he have to get into it in a different way than you did because he had to join organized leagues?
He played T-ball. He played basketball. He did a lot of skiing in the winter, which I didn't do growing up, but my wife did, so she taught him how to ski. But everything was supervised. I can't tell you really ever that he just ran out of the house and went down and played ball with his buddies. You’d have practice and he would play video games with friends in their house. But people didn't really go out and do stuff by themselves, it was just the change in society.
Did that bug you?
It didn't bug me, it was just how it was. You don't want to be that parent who's like oh, yeah, I sent my kid down to the schoolyard on his bike and he did get kidnapped and I never saw him again. It’d be like oh, crap everyone's gonna think you're a terrible parent.
So what were you doing after you sold the company? Semi-retired?
Coaching my kids. When I met Eudora in college and started dating, I said, ‘Look, if you want to meet a guy who's going to retire at 65 and get a gold watch and a pension, that's not me.’ I knew I wanted to start a company, I wanted to sell a company and my dream growing up was to coach my kids in sports. So I got to do that, which was really fun.
So you sold your company to coach youth soccer?
When I first went up to Westchester, my daughter was in first grade and my wife called me up and said, ‘Hey, I was at the elementary school and they're looking for dads to coach girls soccer. So I signed you up. Draft night is Tuesday night.’
So I went down to the draft. We just moved in so I knew none of the kids. There were four teams, it was me and three women, and all the women knew all the girls. So I'm literally flying blind, I don't know a single person in Westchester County other than my daughter. So my grand drafting strategy was to go through the list of names and pick people with a lot of vowels, because maybe they would be from Italy or in places where maybe their dad's played soccer and they'd have some talent. So that was my draft strategy.
Did that work?
No, it did not work. It was still fun.
So why did you pick that year to sell your company? Was it that it was a good opportunity or you just were ready to move on?
I was at a trade show one time and we had really great products, I had great partners with great software, and we were building a distribution network. We had New York, London and Mexico. And I ran into one of our competitors at the trade show and they had offices all over the world, and we were literally knocking their clients off one after another. So I mentioned to the guy that we should combine because I need distribution and you need products. So I'm going to eventually wind up with all of your customers, but it's going to take a while because I don't have people all over the world.
At the same time, I was doing a deal at a bank in America where we were combining with Reuters. So we were working with Reuters, they were going to do a front end and we were going to do the back end. So long story short, we wound up taking Reuters’ business away from the bank. And Reuters was like, well, you must have really great software, would you be willing to sell to us?
So the reason we sold the company is we had two different major companies both wanted to buy us at the same time, so it was great negotiating. It wasn't like we planned it, it just kind of happened.
So you had to work long and hard hours in all those years before it paid off. Was there anything you learned playing sports that helped you succeed with these companies?
Yeah, I hated losing.
Obviously that’s not the case anymore. You play for our hockey team and we never win.
I'm older now. I'm more mature.
Oh good, maybe I’ll get there one day.
The thing that's great about sales is, you're competing, right? My view was, you're competing to win. I guess what I learned is to be competitive. If you don't lose, you make money, right? In sales you're actually playing for something, you're playing for the customer's money. So I think that helped. And when I was growing the company, one of the things I would always look for is to find people to come into our company who were good at something. You could be a good baseball player, you could be a good violin player, whatever. Because if you're good at something, you knew how to work, you knew how to focus and you knew how to persevere. So we would find people who were good at something and hire them.
So when you were more competitive then, did you get pissed or angry ever?
We won a lot. We didn’t lose a lot.
Yeah, but you lost some times right?
We would lose an occasional deal. There was once a bank that came in from Russia, and they were in my office in Westchester talking to us about how, and this sounds absurd, but they would shoot bullets into their bumper because people would know if the car had a bullet in the bumper… it was just bizarre, and I threw the deal. I was like, I don't ever want to send any of our people to Russia to work with these guys.
So we were good. We were a small company and we spent our resources well. If we thought that somebody wasn't going to make a decision, or wasn't going to buy from us, or something else, there's no sense coming in second. So the reason we had such a good track record is we could sort of figure out who was going to buy from us and just focus on them and win.
So how did you hone that competitive trait? It didn't just turn on when you started a company.
I guess I was always competitive. The thing I liked about being a goalkeeper is you actually have a lot of say. When I was a senior, we played in a pretty competitive division and our team only let up three goals in 12 games. I can remember all three goals I let in to this day. So out of 12 games, I let up three goals and I can remember them all. So that instinct of not losing was just ingrained.
And now that competitive drive is gone?
Being competitive in my business was important because there was no safety net. I liked being in charge of our sales because you get your destiny in your own hands. So winning was important. It's how we fueled getting money. And then once we sold the company, I think my competitive drive was diminished because I didn't need to win all the time. It's like OK, well, we won. We had this dream of starting a company, selling it, then raising my kids. I started realizing I wanted to have more family time and less work time. I think the drive to succeed is often times equal to the need to succeed. So once you have a nest egg, it's not as important.
Makes sense why you liked being a goalie then. There is no safety net for goalies.
You’d think with technology now, parents would be more likely to let their kids just run around the neighborhood all day and make friends and have adventures. Cell phones, security cameras, all that stuff would seemingly make parents a little more at ease, but alas, every generation I talk to seems to have less and less freedom as a child. We had the neighborhood kids when I was in elementary school that would go play ‘til sunset, but we moved to a different area in middle school where there were bigger houses and fewer people, so you had to work to find people to play with and schedule it instead of impromptu pickup games.
Also, it was nice of Gary to let me have about a half hour to digest the previous geography lesson before dropping more on me.
The Yankees, and then New York circa 2001
What is your favorite baseball memory? Do you have one?
My favorite baseball memory… probably two of them. One was Derek Jeter hitting a home run on his 3,000th hit and going 5 for 5 because he's got this amazing pedigree and just this amazing story of his life, which is pretty cool. Probably the other one is Derek Jeter coming up in his last at bat at Yankee Stadium and he gets the game-winning hit in his last game at Yankee Stadium. Kind of that Cinderella, story-book, so those are probably my two favorite baseball memories.
I grew up a Yankee fan. I'm a lot older than you, obviously. So when I grew up being a Yankee fan, they sucked. My first recollection of baseball was in the 60s and seeing Mickey Mantle playing the last of his career.
They were just terrible. When you're a Yankee fan, you're only a true Yankee fan if you hate the Mets. So growing up, I had to get through ‘69 when they came back from 14 games out at the end of the season and had a miracle win. So as a kid, it sucked being a Yankee fan. But I always stayed with the Yankees. They’re still my team. Even out here, I still watch the Yanks if I'm going to watch a game.
You’re the first person that said it was tough to be a Yankee fan. (note: between 1965 and 1975, the Yankees did not make the playoffs once before their run of three consecutive AL pennants from 1976-78. Gary was born in 1960 so his childhood was right during that dry spell)
So there was a really long drought where they were just terrible and Steinbrenner would sign the wrong guys. Then we had the good run with Reggie Jackson, hit his three home runs in the World Series. And then there's a little bit of a drought and then they got good again with Jeter and they won a bunch of championships. But growing up, as a kid, they were terrible and the Mets were winning so that was awful.
So you guys were in New York when the Yankees got really, really good (from 1995 on). Did you guys get into that at all?
I was never a super big regular season fan. But I was a big playoff fan cause the Yanks would be in the playoffs every single season and-
(rolling my eyes) Don’t remind me.
They'd be doing pretty well, right? So I became a pretty good Yankees fan. The thing I liked most about the Yankees was, Mariano Rivera came up from the farm, stayed with the Yankees. Jorge Posada came up from the farm, stayed with the Yankees. Derek Jeter came up from the farm, stayed with the Yankees. Andy Pettitte left for Texas (the Astros) for a year or two so I thought that was being a traitor, so I became less of a Pettitte fan. But it was cool because you would have these guys who just grew up a Yankee and stayed Yankees. So I watched a lot of playoff baseball and regular season against the Red Sox. We would watch the big games, but I didn't watch every game.
We’d probably go to games two or three times a year. I’d take my son for his birthday and occasionally would just go in to see a game. Even when I moved out here (to Arizona), when I went back home, I'd get tickets to the Yankees. My mom, as I told you, loved Derek Jeter so we would take her in so she could see Derek Jeter play.
So after the 4 titles in 5 years run, they started getting more into signing free agents and poaching other team’s stars. Was that not as fun as the homegrown teams?
As you could tell, I'm more of a purist. So I didn't like when Johnny Damon went from the Red Sox to the Yankees. I thought that was sacrilegious. Even Reggie Jackson was great when he came in and hit a bunch of home runs. But he was an Oakland A. I was more of a fan of bringing guys up through the farm system and percolate them through your system and keep them; not just go sign free agents.
What was it like in 2001 with the Mets and Yankees after 9/11?
The Yankees and Mets were very important after 9/11. My worst baseball memory is when the Diamondbacks beat the Yankees in ‘01. That would have been the perfect story for America, for the Yankees to persevere, and Gonzalez got that little blooper hit off Mariano Rivera over Jeter’s head.
It was kind of amazing living in New York in that time. I had sold my second company and left working in New York on June 30, 2001. If not, there was a trade show on September 11th in the World Trade Center. It was called Windows on Wall Street, it was the New York trade show for banking every year. The last three years before that, we had booths there and I gave a breakfast speech about banking. So myself and a bunch of guys who worked for me would have been in the World Trade Center if I hadn't retired from my company.
Would you have been on one of the floors that didn’t make it out?
Yeah, Windows on Wall Street was on the top floor of that tower. There were a couple of guys who made it out of one tower. The tower where the trade show was, nobody made it out.
You must’ve known a lot of people there that day then.
We had some clients there, the guy who organized Windows on Wall Street was there. He didn't make it. One of the guys in my high school worked for one of the companies; he didn’t make it. So it was really eerie to think about. I literally had, in my hand, the form to sign up my company for a booth. I remember this clear as day because it was one of the first times I realized, well, I know I was leaving at the end of June and instead of signing it, I was like, oh, I'm not gonna be here in September, so I sent it down to the guy in Manhattan who was taking over my job. And he just never signed up for a booth. So if I would have signed up, he and a bunch of my guys would have been there. So that was sort of super weird.
There were very few people who made it out of the South Tower. One of the guys who made it out from above where the plane went into the tower was the dad of a guy who worked in my company. He's a Canadian guy and he was on a bunch of talk shows and he was one of the very few people who walked down, and he said he only made it because he was at a stairwell. The stairwell was kind of smoky and not particularly passable, but he heard somebody yelling from below saying, ‘I need help! I need help!’ and he was with a bunch of guys who were like well, we can't get down. And he was like well, I’m not going to leave the person. So he figured out how to get down to help this person and then they walked down whatever it was, 86 flights, and they got out before the tower collapsed. Only 14-15 people made it out from above where the plane hit
That is wild to think about. There’s lots of stories of near misses on that day. Actually this article has some scary close calls recounted in it. But if Gary had decided to sell his company a year, or even just six months, later, he would’ve been there. If he’d sold the company and instead of enjoying suburban dad life, he went right into his next project, he might’ve been there, too.
I remember 2001. I was so tired of the Yankees by then. But I was also sympathetic to New York City. So there was this urge to root for the Yankees (for the first time in my life) so the city would have something positive to cheer about. But I also hated the Yankees (mostly for beating the A’s all the time) and wanted the Diamondbacks to win. I guess I got a bit of both. There were some epic finishes in that seven-game series for both fan bases, it just happened that the Diamondbacks had their wildest one in the final game. But the walk-offs in New York were legendary as Derek Jeter became Mr. November.