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.

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: 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.

Favorite memory about your 1996 Pontiac Grand Prix?

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. Incredibly reliable (and lucky). I barely put any money into it until one day it stopped working. Got my money out of that thing.

What do you miss most about the BostInno 1.0 era?

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. There was always an event in town every week. At the Microsoft NERD center or the CIC or MITX or LevelUp or at Campus Live 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. Dave Balter threw his "tech prom." Just a lot of really cool, fun stuff. 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 for roundtable dating with up-and-comers at Lansdowne Pub. That was something I don't see happening nearly as often nowadays.

Why did you call college "a joke" on Twitter and say you're not saving a penny for your kids' college?

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 assumes I found someone tomorrow to marry and have a kid. 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'd 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. 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 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 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. 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'd be putting to your kids' college education they won't need, and put it to work helping entrepreneurs get their shit off the ground. More importantly, give them your time. They need time more than dollars. Lean in.

I'm so happy to see consumer companies in Boston winning now. I used to hate it when people said "Boston doesn't do consumer." Like yeah, I get it, there's not as many here as the valley, but I'm pumped there's been a number of great wins recently and a lot more coming. Wayfair leads the way. Then DraftKings. Then 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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