Boston Speaks Up with The Operators CEO Ryan Durkin

I recently spoke on a podcast with Boston Speaks Up.

You can listen to the podcast here.

Here are the clif notes below:

Where did you grow up and how would you describe your childhood?

Andover, Mass, My dad’s side of the fam is Irish and all from Lowell. My mom grew up in Amesbury, near Newburyport. I was raised by a single parent after my Dad passed away when I was little from cancer. I have a brother, Brad; a sister, Lindsey; and a stepdad, Dave. I grew up always looking to make a buck. Paper route, selling golf balls, hustling in school, caddying (one of my first companies was “Caddy on Call”, which was Dave’s idea... ), working at the golf course, selling Boston Celtics and Red Sox T’s in college, doing internships, all that.

Paperboys unite! I was an Eagle Tribune paperboy myself. What did those early hustles (canpicking, paperboy, caddy) teach you? 

My family is incredibly hard-working. My mom and dad both worked for Market Basket their entire lives, until I was born. In fact, my dad only had one job from age 16 to 36 (at Market Basket). I learned how to put in the hours. I learned how to be on my own. I learned how to be independent. My mom, being by herself with three kids, wasn’t driving me around town all the time. Me and my brother would get on our bikes and go. While caddying, I learned one big thing: To shut up and listen. You can’t talk on the golf course. You have to be silent. And so you end up listening a lot. About all of the guys and their businesses. About crazy, f--ed up stories with their wives and kids. You grow up quick listening to a bunch of 30 to 50 year old guys on the golf course smoking cigars all day. I’m sure it was another reason why I wanted to start my own companies and run companies.

We each rocked Pontiacs back in the day (R.I.P. my Pontiac “Jean-Claude” Grand Am, two head gaskets and all). What’s your favorite memory about your 1996 Pontiac Grand Prix? 

First off ... most comfortable seats of all time. You could fall asleep driving in that thing. And it was a V6 and had some umph to it. And incredibly reliable (and lucky). I barely put any money into it until it one day stopped working. But I got my money out of that thing.

Let’s talk Boston tech late 2000s, early 2010s. There seemed to be an incredible amount of energy surrounding Boston’s innovation scene back then. What do you miss most about the BostInno 1.0 era (before BostInno being acquired by American City Business Journals in November 2012)? 

Oh man. That was a really special time in the city. I think anyone who remembers that time remembers that the community felt really, really tight-knit and “manageable.” I remember that there was always an event in town (every week). Whether it was at the (Microsoft) NERD center or the CIC or MITX throwing events or LevelUp or at CampusLIVE or at all of the bars around town… there was always something going on and we all knew each other and liked each other. There was the Unconference and (Dave) Balter threw his "tech prom", and there was just a lot of really cool, fun shit. And I’ll also say that getting access to mentors back then felt a lot easier. I remember we threw a MITX event that had the CEOs of like 15 Boston companies show up to do roundtable dating with up-and-comers at Lansdowne Pub. That was something I don’t see happening nearly as often nowadays.

You were recently outspoken on Twitter calling college “a joke” and saying you are “not saving a single penny” for your kids’ college education. Can you explain why? 

I’m 34, one month away from 35. I’m single with no kids. The soonest my kids will potentially go to college is around 19 years from now, and that would assume I found someone tomorrow to marry and have a kid with. I honestly don’t believe college will exist in 19 years. It absolutely will not exist within its current form. I think we can all agree on that. But I actually think there will be so much innovation in the space over the next 3, 5, 10 years that I would quite frankly be disappointed in the human race if we weren’t able to figure out better options. I also believe that many people over the next 3-5 years are going to figure out how to scale trades learning beyond the voc/tech. I know hairdressers right now making $100k a year. I know contractors making $250k+ a year in their worst year…. Who set their own hours and own their own companies. I think a lot of people think that with the trades you have to be the guy banging the nails. Not necessarily. A ton of these guys want people to run their businesses for them so they can do what they like/want to do.

Upon your return to Boston, what will you be most excited to do? 

I want Bitcoin to rip, and I want to hire my dream team. I’ve been planning this team for a decade. All of the stars are aligning. At the end of the day, all I want to do is build something that changes lives for the better, that makes me and all my friends mountains of cash so that we can pay off all of our family’s mortgages, travel around the world, do good deeds, live forever, and party.

If you could change anything about Boston, what would it be? 

I do NOT think that everyone should be starting companies. 97 to 99% of people are not the profile. But 10 to 30 out of 1,000 are — and if those 10 to 30 lived below their means for a number of years, built a small base of dollars, invested it in the market, and surrounded themselves by smart people, they’d be able to start companies by age 30. And my challenge to Boston is for those 10 to 30 people to step up and go for it. That’s why we started Wayfund, and that’s why this is a public challenge to all of the other IPO’d and acquired companies in Boston to step up and do the same thing.

I want to see more syndicate funds and more millionaires putting time and dollars to work. At Wayfund, we have something really special: 25 companies founded by Wayfair alumni over the past three years. There are several hundred millionaires that came out of Wayfair … probably several thousand. Pay off your house, save the money you would be putting to your kids' college education that they won’t need, and put it to work helping entrepreneurs get their shit off the ground. But more importantly, give them your time. They need time more than dollars. So lean in.

I’m sooooooo happy to see consumer companies in Boston winning now. I used to hate it when people said: “Boston doesn’t do consumer.” Like ya, I get it, there’s not as many companies here as in the valley, but I’m pumped that there’s been a number of great wins recently and a lot more are coming. Wayfair leads the way. Then Draftkings. You’ve got a gap, but then there’s CarGurus, Drizly, Pillpack (Amazon). Facebook and Google have presences here. Then there’s Butcherbox, OwnUp, Whoop, Embark, 10% Happier, Droplette, TB12, GoPeer, Lovepop, and a whole bunch more.

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