Johnathan Starrling Wins at Life
By Zach Adams-Dominik
Jonathan Starrling is a jetsetter. In the past five months alone, he has flown to four different countries in four different continents, and multiple major cities throughout the United States. I’m told he once caddied for Justin Timberlake, wears $2,000 shoes, and has been clinically determined to be addicted to sex. He’s a friend of a friend and was part of a cadre of young professionals who flocked to Denver, Colorado in the early 2000s hoping to recreate the Silicon Valley in the Rocky Mountain state. He’s young, charismatic, witty, and he came to pick me up for our interview in a brand new Mercedes-Benz; from all appearances, he’s the embodiment of success. As luck would have it, Starrling was in San Francisco in early May on a business trip, and wanted to try out a gastropub a client had recommended. Hungry for answers about the burgeoning tech culture and thirsty for a beer, I accompanied him into the city. As we weaved through traffic on the Bay Bridge and tried our best to circumnavigate the ever-present road maintenance, I asked him about his life.
First off, thank you for agreeing to this interview and coming to pick me up.
Sure, sure. Work is done with for today and now it’s time to play. Besides, no one looks good eating chicken wings and drinking beer all by himself.
Well, I’m glad my company is appreciated, at any rate. Besides an affinity for pub food and fancy cars, what else is there to know about Jon Starrling? Tell me a little about yourself.
Alright. Well, let’s see, I’m 30, I’m V.P. of Education at Apto, I’m a Sagittarius, and in 10 years, I’m going to retire.
What does a vice president of education at Apto do? What is Apto?
Yes, so, Apto is a commercial real-estate software company. Commercial realtors, actually, they prefer to be called commercial brokers, they need something so that they can track all of their different properties and their clients as they go throughout. They need information so they can sell, buy, lease; that sort of thing. There’s no real tool that does that. Think of something like Zillow or MLS, but more for commercial brokers. When you’re looking at different buildings and different office spaces, it isn’t easy to keep track of what building has a space for lease, what floor, what office, or what whole property that’s going up for sale. Apto is how they can track all that. And it helps to track people who are interesting in buying, or interested in selling a space, as well as people who are looking for a space. It can help a tenant or a landlord that has spaces to be sold or leased.
So it’s not like for you or me, then; it’s more for these massive real-estate companies?
Exactly right. My job is to fly to all of the cities where we see growing interest in our service and I train people on the software. The job is fun and I get to meet a lot of people but I like it most for the executive title.
How long have you been there? Did you move to Denver specifically to work for Apto?
So, I moved to Denver a couple of years ago. Five, actually. Denver has the huge start-up scene right now but I moved there to work for Oracle. I did that for three years and then moved to Apto.
Why did you switch to a start-up?
I like start-ups because you get a lot of responsibility, very quickly. I mean, I already have a V.P. title at the age of 30. Heh, so that’s why you switch to a start-up. But it’s also laid back. Marijuana is legal in Colorado and a lot of people smoke at work. You’d be surprised how many people do it. Also, some people don’t wear shoes. I don’t like that so much, but it’s a thing.
You look like you quite like your shoes.
I’m glad you noticed. They’re bad for walking, but a good V.P. sits.
How are you liking it as compared to a bigger corporation?
Love it. Our CEO is very big on culture. He takes us out and is a friend as well as a boss. He’s big on giving you your task and then leaving you alone. He doesn’t care when you’re in the office, or how many hours you worked that day as long as you’re completing your work. A lot of times I work from home. Well, or I’m on the road. That’s completely different from the structure of an old money, established business.
How do you feel about Denver as an environment for start-ups? Is it really the new Silicon Valley?
Yes, I will say that it probably is. All of the big companies are moving out to Denver and Boulder. So, we now have Google, we already have Bing, we have all of your normal app start-ups around here, and a lot of your big tech companies are moving their offices here in Denver. Also, WeWork is a big part of it. I don’t know if you’ve ever heard of places like WeWork—they’re shared workspaces where you rent out an office so you don’t have to pay for an established location. A lot of start-ups go to places like that so that they don’t have to have their own property. Start-ups usually only have a small amount of people, like 5 or 10. These rental workspaces are perfect for that. And it’s not only that; it’s a space where you can go to get counselling. So people who have sold off their companies, they come in and they’ll give you one-on-one counselling on how to be successful. There are places like that all over. I use them when I travel to hold meetings.
Why Denver, of all places? I mean, why are businesses moving out there when the Bay Area is still a thing?
It’s a bunch. One thing I would say is the cost of living. Denver has plenty of room for expansion and now it’s growing rapidly. Land is cheaper than other places and the political climate is there. I’m sure tax breaks are part of it with Colorado trying to get more companies to move. And, honestly, I’m sure the legalized marijuana has something to do with it. Especially with start-ups. People like it and they’re going to do it; why not go where you don’t have to worry at all? It’s just the right environment right now. Anyone can get a job. You can be dumb as hell and be an executive. People are pissed off. I mean, Denver is the new California. We do what you do, but better.
With so many companies already over there and more starting up, is it a buyer’s market? I mean, do you feel confident in your ability to jump to another company if the start-up you work for goes under?
Well, it is flooded, but, based off your skills, you can do alright. In two weeks you could probably get a new job. I work in a very niche department, so I’m okay in that I don’t have competition, but the openings are lower. The bigger problem is that what I do, which is basically training, is usually one of the first to be let go in a downturn. Honestly, it’s probably the first things that goes. But I do customer education as well, so I deal with the whole training aspect, internal and external. It’s very easy to go from company to company if you wanted to. I wouldn’t because my goal is to be CLO, which is Chief Learning Officer, and I’m on the path to do that on Apto. Plus, like I said, I don’t plan on working too much longer. My goal is to retire by 40 or 45. I probably won’t jump ship anytime soon.
How likely do you think you’ll be able to do it?
So, with the cost of living being so cheap and the kind of money you can make, even with no degree, it’s kind of crazy. Think of the gold rush, but with apps, and weed, and everyone is getting rich.
Do you ever encounter any issues with being a young professional? Do people respect you? Is there a hurdle you have to get over?
Well, not really. Most guys at the start-ups are this young. Thirty is actually old for my company. And my customers, I can deal with customers all the way up to 80 years old. The real-estate profession tends to attract the older crowd, so a lot of the brokers are older. And yes, they respect you because you have knowledge and you’re sharing with them what they don’t have. As long as you know how to engage your audience, that’s all that really matters. Most of the guys I work with are in their twenties. I tell them how life is.
What’s next for you? Any big plans after your early retirement?
Hah. I want to open a club called Kinetic. Have you ever been to an oxygen bar? With the hoses? I want to do something like that, but with vaporized weed. It’ll be called Kinetic because the floors will be hooked up with pressure sensors that generate electricity. I want the whole club to be run off the dance floor.
So, when the lights start to dim, you have the DJ play?
Right now? It’d have to be D-Lo. Everyone start jumping! Hah.
We had made it to the restaurant and had already begun on our second round when Starrling got a phone call. He apologized, gave me a one hundred dollar bill to cover the food and an Uber back into Berkeley, and got up to leave. I asked him if everything was alright. He took a moment, looked down, pointed at his marvellous shoes, and said, “It’s always alright.” With that, he left. I ordered another beer for myself and contemplated my $40 Vans and previous life decisions. Our mutual friend had told me earlier that Starrling had never been to college. He’s also only three years older than I am. The world is a curious place.