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  • Writer's pictureZach Servideo

062: Boston Speaks Up with The Operators CEO Ryan Durkin

Boston Speaks Up (BSU) is a podcast owned and operated by Value Creation Labs. Listen to BSU on any podcast platform you choose: SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play.

Ryan Durkin is a serial entrepreneur, operator and product guy who’s interwoven himself into the fabric of Boston’s elite tech talent. Following his latest successful stint serving as head of product at Drizly (sold to Uber for 1.1B), Durkin is now busy building a sports agency for tech professionals in Boston -- The Operators. Durkin’s goal is to represent the top percent of tech talent, and offer them everything that agents provide to professional athletes -- from opening doors and closing deals to creative contracts and fan ownership. Durkin negotiates on their behalf much like a sports agent would, and helps The Operators and founders build strong companies.

Durkin is no stranger to startups. He previously founded Wayfund, HeadstoneHub, and OneGoodMeal. Additionally, he was the cofounder of Dailybreak (acquired by Connelly Partners) and was a product manager at Wayfair (pre- and through IPO).

We got a chance to catch up with Durkin before he hit the road on his motorcycle for a six-month journey around the country. Enjoy.

You can listen to our podcast discussion with Durkin embedded below or on any podcast platform you prefer (SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):

Enjoy an abridged written version of our interview with Durkin below.

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

Andover, MA. My dad’s side of the fam is Irish and all from Lowell. My mom grew up in Amesbury, near Newburyport.

Childhood: Raised by a single parent. Dad passed away when I was little from cancer. I have a brother, Brad. Sister: Lindsey. And step-dad Dave.

Happy childhood. Played outside a lot. Always have liked bikes and athletics.

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 for their entire lives up until I was born. In fact, my dad only had one job from age 16 - 36 (Market Basket). “More for your dollar.” 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 to shit. Me and my brother would get on our bikes and go. Looking back, it’s a little funny thinking now about what my friends or friend’s parents may have thought seeing me and Brad diving into trash bins around the elementary and high school, but who knows.

While caddying, I learned one big thing: To shut the fuck 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 fucked up stories with their wives and kids. You grow up quick listening to a bunch of 30-50 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 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 Balter through 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 (and this is even pre-covid). I remember we through an MITX event that had the CEOs of like 15 Boston companies show up for it to do roundtable dating with up and comers at Landsdowne Pub… and that was something that nowadays I don’t see happening nearly as often.

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 ~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.

And I know the counterpoints: But Doctors and nurses need to go to college. But Lawyers need to go to college to learn. And at face value, there’s a part of me that thinks: “Maybe you’re right.” But I also want a part of you to think: “What if Durkin is right?” Look at what Lambda school is doing right now for engineering… a very, very technical skillset of engineering. They are teaching people to program (for $0 from the student) and literally putting them in companies (at no cost to the company) for a full month and letting them try out the person… again… for free. And then if the person gets hired they will pay lambda school back via an ISA.

ISA’s are the future of education. I firmly… and I mean… very, very firmly believe that.

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.

Okay, let’s talk about your experience and how that’s helped prepare you to run The Operators. What are some of your biggest lessons from your time in particular at Wayfair and Drizly?

Wayfair lessons:

  1. Leadership. Growth. Culture. You assess those three things. You make the most informed decisions.

  2. There is nothing better than a strong CEO and cofounding team. Niraj is the CEO of CEOs in Boston. Steve is an amazing founder, technical, and cares deeply about his people.

  3. Seeing what strong leadership and a strong executive team make or kill businesses. Everyone in a company is important, but if your exec team is fucked or 3/6 suck… you’re fucked.

  4. Growth cures all (ok ok… not everything… but you get my point). Growth creates opportunity… for you… for your peers…. For moving laterally… for moving vertically up…. For gathering new skillsets…. Etc. Always optimize for learning… and the best way to learn is going to a high growth company.

  5. A strong brand matters, for two reasons: 1.) Most strong brands have great distribution and great products and there’s learnings there, and 2.) Most people do work for products they love.

  6. Role matters. You have to dig the work you’re doing on a day to day basis. I went to Wayfair to learn product from legit people, and it’s the best career decision I ever made. And people took a gamble on me. I owe a lot to Paul Toms and Krista Toms and Josh Berg who got me in the door there. Josh was an amazing boss and has a phenomenal gut for product (beyond being super analytical and a good person to me). I love product and building things.


  1. Highly regulated markets: Jeff Bussgang gave me really great advice when I was thinking of leaving Wayfair to go to Drizly. He said: “look to highly regulated markets. If you can figure out the regulation, growth will come.” He pointed to Uber and what they did in the taxi medallion space, and a few healthcare companies and what they did in healthcare. And he was 100% right. When I joined Drizly, <1% of alcohol was sold online. Today… it’s a lot more than that… and Drizly is a massive part of that (the #1 leader in the space).

  2. Go after big markets. “Fish in big ponds” was the advice I got. And that’s something that I know Carmen Scarpa was right about and that I believe.

  3. 10xers exist. Retain them and win. Don’t and lose. The 10x engineer and the role of Data Science and the power those guys unlocked. There were a few engineers at Drizly who I know are 10xers.

It seems you (like me) believe strongly that talent is consistently undervalued and underpaid. Is that something you experienced personally? Can you elaborate or give some examples?

  1. Power to the People: I’m a big power to the people guy. I believe that there is a tidal wave of activity right now that is pushing power into people’s hands. This past year socially has shown you a lot of that, and not with

  2. I believe in 10x employees. I just do. In the same way I believe Tom Brady is the GOAT, that Michael Jordan is/as the best basketball player of all time (and Lebron now). There are outliers who are the superstars. And there are also another tier of players that can come together to win championships: Paul Pierce, Garnett, and Allen. So…. why do sports teams pay millions of dollars for top players? Tech startups often have just as much money IF NOT MORE than they do. Players… Operators. Teams… companies. Why the differential?

  3. Companies don’t take into account the following when thinking through comp:

    1. Cultural add: Cultural addition and the value that brings towards motivation, inspiration, and position energy.

    2. Network: An employees network and the value that brings to hiring. If you hire Ryan Durkin to lead Product or People Ops, you don’t just get my skillset… you get my network… which I believe is probably 10-1,000x more valuable.

    3. Risk.

    4. The influence one phenomenal person can make.

  4. Creator / community economy & crypto: The community economy and creator economy are going to change this.

    1. Basketball players owning teams.

    2. Celebrities tokenizing their music and art and making commissions.

    3. Operators angel investing and VCs leaving their firms to start their own.

    4. People are starting to take the power back… and with it… money.

  5. Comp data I have: I have the best compensation data I know of in Boston. I don’t know anyone that has more information than I do directly from the horses mouth. When I compare what I have for their data vs. what I see in all of these studies… there are big differences.

  6. Overpaying: One last point: I think a lot of people are overpaid in Boston as well. I see it A LOT. And it’s really unfortunate.

  7. Product Designers: Ex: A+ Product Designers in Boston are almost nonexistent. I know 10 who I would trust to build my own products. I know 1,000 soldiers, and I know 10,000 who I wouldn’t let anywhere near anything I’m building until they develop their skillset. Product Designers are the most underpaid people in Boston. In California, it’s a different story… they put their Product Designers on a pedestal. Not in Boston. That needs to change.

  8. People Ops: Ex: People Ops leaders don’t get the credit they deserve. Old school thinking: Hire a Head of People somewhere between 75-100 people. Newer school thinking… hire them around employee 30-75. My thinking: If you’re not a charismatic CEO, you should hire someone as your Head of People in your first five hires. Why? Because if you fuck up at the foundation… it will be close to impossible getting out of it. Think of all of the things you can fuck up from the beginning:

    1. Overpaying executives / fucking up the cap table.

    2. Early disputes amongst cofounders that don’t get resolved.

    3. DEI and equality issues from the getgo.

    4. Not having someone early in the process to focus on the entire employee lifecycle IMO is as bad as not having all of your employees focused on your customers. If you don’t serve your customers… the company goes nowhere. Same with employees.

  9. Ex: I think the best PM’s start in BI and/or engineering.

  10. Ex: I think engineering will become more commoditized over time + the ability for more people to product MVP’s on their own without engineers will become more and more prevalent. So many creator economy tools are being produced to help non engineers run their companies. And so much focus on education is pointed towards STEM now (and we need 100x more of it) but it’s turning the ship in a good direction.

What was the catalyst for you founding The Operators, and what is your vision?

  1. Vision for the company: Our mission is to empower Operators to reinvent the future.

  2. Mission: We empower operators and build Dream Teams.

  3. Why recruiting is fucked: believe the recruiting industry is completely fucked. I think it’s backwards and I’ll explain why.

  4. Creator economy and community economy are coming hard.

  5. I love everything crypto and the world of decentralization is here and it’s not going away. Power to the People.

  6. When you look at the similarities to sports, it’s so beautiful.

    1. Players/Operators

    2. Teams/companies

    3. Coaches/a need for coaches.

  7. People don’t know what they’re worth.

  8. People don’t know how to negotiate.

  9. People don’t know what companies in town are good or bad.

  10. People don’t have enough information to make decisions.

  11. People are unhappy.

  12. People need a Jerry Maguire and a Jiminy Crickett.

  13. And I think I’m the guy to do it. I have 13 years of experience building companies on the Operator side. My career has been in Product. I’ve managed Analytics teams, Product Design teams, Merch/Category teams, and People teams. I’m a Finance guy who can build financial models (college + I’ve run all of my own company finances for a decade). I understand the business side. I can interview candidates. I have a good network. And I have a good gut. Interesting point: men without dads in their lives become increasingly good at reading people.

Do you have any formal relationships with companies (in a recruiter-type capacity) or are you purely representing individual talent?

  • The long term vision for the Operators is to be ISA focused. I think the industry is heading there and there are many companies right now helping build out and prove that market. I love what they are doing and I applaud them.

  • Today, I have partner companies who pay me if I send them a good candidate that they hire. I call myself the “Pre-Executive Search.” AKA…. before you go hire an exec firm $150k and equity for a hire, ask me and I’ll connect with my squad and see if there may be a fit. I let all companies know I’m not a volume guy and don’t do any proactive hunting. At the end of the day, I spend the majority of time helping my Operators with their lives. Sometimes I make money. Sometimes I don’t. But I know where I’m headed, and since I am not raising venture and am self funding, I’ll do this on my own terms on my own time horizon.

  • One massive add for companies is that the people I represent I am there for… for life. Like… life, life. You got a question on equity? Hit me. You want an intro in town? Hit me. You got a problem with your manager and want advice? Hit me.

Who are some of the people you’re representing at The Operators?

Pat Twomey

Brendan Caine

Meredith Mahoney

Mike Brown

Jen Raines-Loring

Dan Smith

Adam Conrad

Colleen Tartow

How do you approach negotiations on behalf of your clients?

  • First off… I really push to know my clients, and we are VERY honest with each other. I get to know where they are strong and weak. I get to know what matters to them and what doesn’t.

  • And I have really good data on market comps that is my own proprietary set of data.

  • There’s always a win, win.

  • There’s base salary + bonus + equity, but then there’s also much more creative stuff:


  • Trends I think you’ll start to see from other companies (that I have implemented with my own company).

    • Contract year terms. This is a two year contract with a one year player option.

    • Up front agreeing to the raise amount each year.

    • Up front agreeing to how much the player option will be.

    • Retention grants. Upfront agreeing to these. Wealthfront popularized this in 2013. At the 2.5 year mark, you’ll get a retention grant and every year thereafter.

    • Tokenization. We’ll have an Operator token that can be traded on exchanges on day one.

    • Guaranteed severance.

    • Dollars for hires you bring into the business. When I joined Drizly, I brought in 20+ people to the company in 3.5 years. That’s a lot of value. One could say that as an executive you’re expected to do that, however, the closest executive brought in maybe 2-3 hires. That’s a big difference.

    • I think negotiations will be made public. Shark tank negotiations are public. Why not individuals. Today you say: “That’s crazy!” But why? It could happen.

You’re about to get on your motorcycle and tour the country for six months. What are some of the places you’ll be visiting and how do you plan to mix work and play from the road?

  • I’ll go through all this fo sho.

  • Quick gist: Virginia. NC. Miami. New Orleans. Austin. New Mexico, Arizona. Hawaii. Upper Cali. Utah parks. Montana. Boulder/Denver/Colorado Springs. Nashville. Back up east coast. Living in NYC through EOY. Then who the fuck knows. Boston. Europe? Not sure. The world is my oyster.

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 want to see two things:

  1. I want to see more people rolling the dice.

  2. And I want to see more people ACTIVELY supporting those taking the risk.

Note: I do NOT think that everyone should be starting companies. 97-99% of people are not the profile. But 10-30 out of 1,000 are. And if those 10-30 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 10-30 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. We’ve funded four companies in our first year and there’s 25 other companies now getting help. Step up to the fucking plate and do the same. It takes 1 hour a month per member, and managing it all is like five hours of my time a week doing the bare minimum. If you don’t have a girlfriend and don’t have kids yet, like me… step the fuck up and put in the work.

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 and save the money you would be putting to your kids college education that they won’t need, and instead 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. There should be a hubfund, a logmeinfund, a toastfund, a draftkings fund, a this fund a that fund. Etc. The Endecca team. The Vistaprint team. The Compete team. There’s a bunch of companies that spawned off a bunch of entrepreneurs. I want to see more of this. Us as Drizly alumni are starting one. And I have the blueprint… the template. And I’m giving it away. So whoever from these other companies…. If you want it…. Come and get it and I’ll teach you what to do.

I also think we need a revolution when it comes to space in the city. I’d love for companies to open up their offices and joint share their office space. Get Drift and Drizly and TB12 and a few other companies down on Boylston to share their offices and let people bop around. Let’s turn restaurants that went out of businesses into coworking spaces that serve salads and pizzas. Let’s open up the number of venues people can go to to talk tech. This is what friends of mine in the valley have always said about the beauty of San Fran: everyone is talking tech. Well… let’s play this out… I live next to North Station. What are my options to go to talk tech or overhear tech. The Harp? No. Hurricane O'reilly's? No. The Boston Garden? Maybe, but probably not. There’s a WeWork at One Beacon but you have to work there to get in. I want like 20 District Halls. Throw in a coffee shop and a bunch of tables and chairs. Take some of this infrastructure dollars everyone is talking about and instead of fixing Summer Street, build innovation hubs to increase IQ and tech progress so that we don’t have to pave the roads again in 20 fucking years but instead invent a new solution that goes over the roads so we never have to pave roads again. I want a venue where I can go dancing at a nightclub and bring my laptop and do work at the same time. I want to be able to feel so overwhelmed with places I can go to talk to people about big ideas that my head fucking explodes. Today… (even in a noncovid world) there ain’t much other than bars. It’s kind of funny… Justin Robinson (cofounder of Drizly) and I go to Tavern in the Square at North Station and bring our laptops and just work and drink beers. I’ve never seen anyone ever do that. I want to see more of that.

First off, 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. You’ve got 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. I think PerchHQ is one of the companies to watch in Boston. I like the space they and Thrasio occupy. You’ve got Klaviyo rocking. Toast rocking.


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