Not Your Average Founder Spotlight: Ryan Durkin, Founder of The Operators

Welcome to “Not Your Average Founder” with Ryan Durkin, Founder of The Operators. We write these pieces to give a glimpse into what Wayfair alumni founders are building, but to also get to know them as people.

Q: Durkin, give us the scoop on what you guys do at The Operators?

Durkin: We’re operators building the premier sports agency of tech in Boston, the city of champions.

Let me ask you something: Lebron James has an agent, coach, and manager. Why don’t you?

It’s our opinion that you should…. and that you will.

And we’re building that reality.

I wrote this post in early 2020 detailing what I’m building, but you can think of it as taking what exists in the sports industry today and bringing it to tech. Sports has teams… we have companies. Sports has players… we have operators. Sports has owners… we have founders. Sports has coahes… we have mentors. Sports has agents… we have connectors. But in tech, I believe there’s not enough emphasis and power in the hands of the Operator. We aim to give power back to the people.

I believe the best Operators (and founders) will be represented, managed, and coached by the best, most experienced tech operators within the next five years. And I believe that those who don’t will have 1/10 the opportunities presented, 1/10 the L&D opportunities, and 1/10 the financial freedom. I believe this so much so that I’m betting my career on it.

Picture a world where you could focus on your craft (Product, Engineering, Marketing, Sales, etc) and not have to think about managing your life and career. What if you had Jerry Maguire to open doors and close deals for you? What if you had a VP Marketing/Product/Design/(insert domain discipline here) at Airbnb, Wayfair, Amazon, Shopify, Google, etc, coach you. And what if you had the most elite, forward thinking finance leaders managing your finances? Experts in crypto, in employee stock options, tax accounting freaks. An arsenal of support.

The recruiting industry has been ass-backwards for years, with companies selling, selling, selling roles and opportunities to people. We’re flipping this world to be consumer first and approach someone’s next job through the lens of planning out the next 30, 40, 50 years of their lives and aligning the “next best thing” towards those career goals. And our agents are operators. That’s one key difference. Everyone on our team has a background in a domain discpline (ex: I have a background in Product, and I represent Product people. My other agent who is an engineer represents engineers. My other agent who is a Marketer represents… you guessed it… Marketers). Domain discipline matters. Why? Because it allows you to assess people. Our world is about access and assessment. And it’s the key to transforming this industry.

The rise of the superagent operator hath begun.

Q: How do you plan to scale? Is there tech?

Durkin: For the past 18-24 months I’ve been focused on one thing and one thing only: Helping my Operators win. This means mapping their careers, opening doors, and closing deals (negotiating) on their behalf. I will continue to do that on a larger scale. I now have tech behind the scenes that helps me optimize, repeat, and learn. This in and of itself could be productized for other agents. Longer term there could be a forward facing product. But I always remind myself one big thing: there is a graveyard of founders/companies who have tried to reinvent the recruiting / executive search industry who raised venture, built tech, and spent more time maintaining that tech than solving the actual problem and helping people. I learned at Wayfair the importance of focusing on the customer not the tech, and that’s what I’m going to do.

Q: Has COVID helped or hurt the business? What are the biggest trade winds helping you in your favor?

Durkin: I cofounded my first venture backed company in 2008 during the financial crisis, and my third going into my first full year in a pandemic. For me, as someone who likes choatic environments, I think it helped me. It challenged me to go above the rim and perform. It motivated me. And in a world where I am helping build this new future of recruiting, it allowed for me to carve out a new approach in a changing industry. I wrote this post at the start of the pandemic: “The Rude Awakening for Boston Tech, and the Need to Create Now” stating there is not better time in human history to start a company than right now. And I firmly, FIRMLY believe that. Every industry is changing. What would have existed in 2031 will now exist in 2024. It’s an amazing time.

As for my customers… at the end of the day, all people want help figuring out what will make them happy in their lives. People want support (professionally, personally, all of it), and that’s where I come in. And, all companies want A+ talent. So as long as I stay in the premium / A player range, nothing changes. Even if the economy tanks 3x as worse as in March 2020, consumers still want help with their careers, and companies will still want and need A players.

In terms of the big trade winds I’m seeing affecting my business… there’s a few interesting affects some of these have had:

• Work from home has brought San Fran talent and NYC talent to Boston. It’s exciting. Both of those cities have super strong talent, and I’m happy to bring them to my city. Boston has almost a dozen companies I see IPOing in the next 2-3 years in town. There’s real opportunity here.

• People are taking steps to make an impact 10x more in their professional lives than in 2019. They are thinking longer term. And with the emphasis being put on mental health, people are putting more emphasis on happiness and well-being… which means not going to some companies that have shit leadership, shit growth, or a shit culture.

• Cyrpto, decentralization, and the creator economy are putting power back into the people’s hands. I’m super excited about everything this represents and how it will transform the working world. I could go on and on about this, but needless to say it will play a big role in what I am building.

Q: Biggest accomplishment to date?

Durkin: I’m incredibly proud of the fact that Drizly recently sold to Uber for $1.1 Billion (shameless flex). When I joined Drizly as their Head of Product in 2016, we were a Series A company doing $20 MM in GMV with <1% of alcohol sold online, and about 40 employees. Today the company is doing 20x+ that in GMV, has brought alcohol online in the multiple single digit % points, and is several hundred employees. I was hired to build and lead the Product team, BI team, Data Science team, Merch team, and Category Management teams from scratch. Those teams did not exist prior to me arriving and I really enjoyed hiring and leading those orgs. Having been at Wayfair pre-IPO and post-IPO, I knew I could take my learnings from there (and roster) and plug and play and MOVE fast. The acquisition by Uber is the start of what can be a massive empire. That said, I think Drizly could be a $30 Billion company on it’s own (considering only 3-4% of alcohol sales are online today), but I think that Uber + Drizly is better than Drizly alone and better than Uber alone. I’m excited to see the impact the two companies will make together.

Q: What has been your proudest moment?

Durkin: My proudest moment has nothing to do with me. It was watching my brother receive his Eagle, Globe, and Anchor at Parriss Island, and officially become a Marine. Beyond having insane respect for our military servicemember, it was a very emotional moment for me to see my brother reach that goal… something he had wanted for years. Work. Ethic.

Q: What got you into Product, and what tactical advice would you give someone going into your domain?

Durkin: I cofounded a company out of college with my two friends Jared and Boris. It is called Dailybreak (formerly known as CampusLIVE). It still exists today, 12+ years later (wild).

After four years running that company, I decided I wanted to triple down on Product Management and go to a company where I could be apart of a company with (1) Experienced founders, (2) An experienced exec team, (3) High growth, (4) Super talented people, (5) A strong brand in the market, (6) Pre-IPO, and (7) Be working in product. Wayfair fit the bill, and I’m forever grateful to Paul Toms, Krista Toms, and Josh Berg for bringing me in.

As a 26 year old who had founded a company but who had little formal training in Product, they took a gamble on me. Maybe someone will take a gamble on you if you put in the work.

To those looking to get into Product, a few things:

1. I wrote a 100% free guide to becoming a Product Manager on my website. We call it “Operator U”. It will take you about six months part-time to do on your own. So ya… that’s a good start. (Thank you to the other Product leaders who helped with this). We pulled together all of the best free online courses we saw on Product Management and have other recos in it.

2. Build shit. I mention this in the guide, but if you want to go into Product, you have to build shit. There are a thousand local construction companies, hair salons, restaurants, etc that have shit websites. Websites that look like they were built in 2001. Go and build them a new one… for free. Squarespace. Wix. Weebly. Etc. All tools you can learn in a day. Build them a new site. Copy other sites. Start to understand UX patterns and how a website flows. Include CTA’s. Forms. Contact info. Fuck with copy. Practice. Rinse. Repeat.

3. Surround yourself with strong Product people to learn from… but get creative with it! Go on Linkedin and pull together 10 names of people you want to meet, and invite all 10 of them out to a steak dinner on you (or a lunch). In a world of zoom, pick a restaurant near them and get COVID checked so you’re not sick and so you don’t freak them out. But ask them out. It’s rare that someone will turn down a steak dinner… especially if they don’t have a family and kids to spend time with at night. Send them a list of quesitons beforehand that you want them to think about and answer to help guide the convo.

4. And if you have a few years of Product experience looking to level up, check out what Balfour is doing with Reforge. I love their approach. Check it out.

5. You can also check out Lenny’s $950 course of getting into Product. I’ve heard very good things. And subscribe to Lenny’s newsletter. He and it are awesome.

Q: Most interesting nerdy thing you’re learning about right now in the world of design?

Durkin: I read about crypto, blockchain technology, and in particular web3 and future dapps, for about 1-2 hours a day. Ryan Selkis (twitter: twobitidiot shoutout) got me into Bitcoin in 2014. Financially I’m motivated by it, but at the end of the day, I’m a Liberitarian at heart and I believe in the decentralized world that the blockchain provides. I could go on and on and on about Bitcoin and ETH and that whole world, but I won’t. If you’re interested in learning about crypto, I’ll simply point you here, here, and here. Read all of it. It’s the future, and you’re going to regret it BIG TIME if you don’t. Trust me.

At the end of the day, I was always a nerd in high school and college. And my crypto passion is probably my biggest nerdiness. But I also ride motorcycles and can rip it on the dancefloor… So maybe I’m not so nerdy afterall. 😉

Q: Tell us something people don’t know about you.

Durkin: I’ve played the piano since age five. Hand me a piece of sheet music and I can (probably) play it… or at least used to hahaa. But also a weird thing… I’m tone deaf and if you take the sheet music away… I can’t remember any songs and play them by ear. It’s really sad. I’ve always idolized people who can play by ear. I can’t. Sucks.

Q: Personal goals in 2021?

Durkin:

1. Scaling my business and 3xing the number of people I help/represent 2xing revenues.

2. Motorcycle across the country.

3. I want to learn to fly helicopters. I’m watching youtube videos each week, and my buddy is going to take my flying in late summer. I’m pumped. I’ve been in a helicopter three times, and I’m also super afraid of heights. Not sure why I like it so much given my fear. Go figure.

4. I want to learn how to officially solve a rubix cube. I can solve all the way through to the last step and then I forget the last one. I’ll get it.

5. I want to become relatively fluent in Spanish and get by on a trip down south.

Q: Favorite place to zen-out and relax and why?

Durkin: Nahant Beach. It’s my happy place. Always has been. I think it’s the gem of Boston and such a cool spot. I also tried kiteboarding and want to continue learning and I get super jealous watching all of the people kiteboarding there on windy days. Such a great spot, and only 25 minutes from Boston! Woo woo!

 Q: College. Did you go or not? Still worth it or not?

Durkin: I went to college. And while college was great to me in the friends I made and mentors I met and learned from, I think college today is a complete waste of time and money. I am not saving a single penny for any of my future kids college education because within 20 years, I believe college will not exist. Anyone who knows me knows I’m very vocal about this, and it’s the area that I often get the most flak for. But hey… I am who I am and that’s what I think.

I side with Elon Musk on this topic: anything you want to learn you can learn on the internet via YouTube, Reddit, Wikipedia, Khan Academy, and for 100% free.

I think that the ISA model Lambda Schools of the world are the future. I think that all colleges today should be free, not taught by professors, and that campuses should be massive venues that resemble the tech campuses of Apple and Facebook today.

I think that socially people should still congregate in areas together to “grow up,” which will allow for boy-meet-girl, girl-meet-boy, or gender-meet-gender and meet, exchange numbers, date, get married, party, have kids, etc. But no, I hate the idea of college, and I think that we should decouple “socially interacting” from “educating” and quit with the lame excuse that “college is good for people because it teaches them how to survive on their own.”

Q: Outside of The Operators, what are the biggest innovations you're following right now and why?

I invest my time and money into four areas:

1. Companies transforming the future of work

2. Crypto

3. Longevity, living to 150, & mental health related tech

4. Ecommerce and consumer marketplaces

Other areas I like to read about:

1. Pre-K education and transforming the education system from the source.

2. Financial services transformation

3. Space travel for the purpose of exploring earth, not mars. I think that when rockets can get us to China in an hour rather than 24, the ability for humans to explore this world’s cultures is going to magnify x 1,000 and I think it will be great for humanity and understanding one another.

Q: Favorite book and why?

Durkin: How to Win Friends & Influence People by Dale Carnegie. Next question.

Q: Who inspires you?

Durkin: I think all men who grow up in single parent households need some good men in their lives to look up to. Here are mine:

• All of the Operators I surround myself with and founders who are executing at a high level.

• Musk: For his curiosity, learning, ability to dream and most importantly… for his ability to execute like a ferocious animal.

• Denzel: For his smoothness, belief in God, and taking chances.

• Forrest Gump: For his love of people and ability to give up control and live a great life.

• The brother’s from the Boonedock Saints: Because it is a reminder that nothing is more important than family… and because you shouldn’t take other people’s shit.

Q: First place you're going to vacation post COVID?

Durkin: American road trip to explore/work as a digital nomad for a few months. 10,000 miles of open road baby. Leaving May 1.

Q: Anything else?

Durkin: All I’ll leave you with is that my fellow Operators and I plan on building the best team in tech that Boston has ever seen. Period. I want people to look back 10, 20, 30 years from now and say: “Remember the 2004 Patriots? The 2008 Celtics? The 2025 Operators?” It’s coming.

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That concludes Not Your Average Founder Spotlight. Thank you Durkin!