Talk about underselling yourself. Ryan Engel volunteered to work for Peloton for free — just to get in the door as early as possible. That’s how much he believed in the vision of the now-global fitness company, before Peloton even had a prototype.

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Now that Peloton is among the world’s most recognizable workout brands, it’s abundantly clear that Engel’s entrepreneurial spirit, high risk tolerance, and strong conviction paid off. But like most seemingly overnight success stories, the household-name brand has humble beginnings. 

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When Peloton was little more than a pitch deck, the company’s unpaid co-founders, including then-CEO John Foley, weathered “thousands of Nos” from investors. But after a successful Kickstarter campaign that Ryan helped drive, Nos started converting to Yeses. 

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Once Peloton launched its first stationary bike in 2014, the company quickly developed a cult following, thanks in large part to its fleet of invigorating instructors. In 2018, Peloton raised $550 million in venture capital at a valuation of $4.1 billion. Ryan’s volunteer spirit led to a salary, and his ideas helped speed the company’s growth, not to mention his role in business development during his near decade tenure at Peloton. By 2019, the company had sold 577,000 bikes and treadmills, and during the pandemic, Peloton became a household name and a leader in the stay-at-home fitness movement. 

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Ryan’s career ascent started with an email

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As Peloton’s fifth employee, Ryan was the first non-founder member of the team. Ryan initially got wind of Peloton through an investor friend who had the company’s first pitch deck, but he wasn’t actually interested in investing at the onset. Inspired by the pitch deck, Ryan emailed John to express his interest and ended up spending an entire day together in 2012, discussing the vision for the future of connected fitness. Ryan decided then that he wanted to quit his “pretty miserable” job in sales and trading at a small boutique investment firm. 

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Although Ryan didn’t leave that meeting with a job offer in hand, he and John kept in touch for months and in May 2013, Ryan wrote an email with the subject line “Time for a change.” “I said I really wanted to work for Peloton and believe in the business. Even though they had no money, I would work for free until they could pay me,” Ryan says. John immediately responded and said, “You're hired.”

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From there, Ryan helped to build Peloton from the ground up, converting loose ideas into sales engines. His first project was to spread the word about the Kickstarter, even getting his mom to pledge. Fast-forward to Ryan’s first day of paid work, and he and the founders flew to Taiwan to meet with their first manufacturer. On the plane ride home to the States, Foley asked Ryan to conceptualize what would become the future of retail innovation for Peloton.

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Here Ryan tells the story of how he launched Peloton’s initial retail presence in a Jersey mall to reaching a rut where he didn’t see a path forward to landing the promotion that would hoist Ryan’s career — and Peloton’s future — to global scale. Along the way, he reflects on the hard conversation that would ultimately lead him to launching Peloton’s international presence and meeting the love of his life.

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Rachel Star: When you joined Peloton, nobody had ever heard of it. Where you were in life and career at this point — and how did you get in front of Peloton?

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Ryan Engel: I had just graduated college in May 2012. I knew something philosophically was wrong with my job, but I couldn't really pinpoint it. I met with a mentor of mine and started telling him how miserable I was. He said, “Why don't we take home 20 pitch decks that I'm looking at right now?” The first pitch deck on that pile was Peloton’s.

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I went through the deck, called my mentor, and said I'd love to meet with the founder. He said, “I'm definitely not investing in that company, but I'll make an introduction.” 

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I met Founder & CEO John Foley in September 2012. At that point, Peloton was just a paper-napkin idea. After I spent a day with John and hearing about his vision, I called my mentor and said, “You should invest your full allocation.” When he asked why, I said, “I want to quit my job, and this is the company that I want to work for.”

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Rachel Star: That level of conviction is pretty tough to come by. How did you know that you wanted to join Peloton?

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Ryan Engel: I still vividly remember the meeting. I left and was almost in a half run-skip down the street because I was so energized and excited. I was like, “I have to work for this company, and I have to work for this guy.” I was going to do everything in my power to make that happen.

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The reality was, the founders didn't have any money and were raising their first round from friends and family. I think it was a combination of John's incredible charisma and storytelling ability. You could tell he had a really high GTD [Getting Things Done] — he responded to all my emails immediately whenever I had a question. I was helping diligence for my mentor.

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John Foley was on a mission, and you’d feel that energy coming from him in every interaction. Whether in person or virtually, you could very clearly see his vision for the future that he was describing — and he was going to be the guy to bring it into reality.

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Chris Marty: I love that your story hits the point home about the importance of a charismatic leader and vision that you can get behind. You describe this instinct that I think everybody who joins at this early stage should feel. When you joined as employee number five, you joined in a role that wasn't perfectly specced. Can you tell us about the capacity in which you joined and what that turned into?

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Ryan Engel: My initial title and role was director of business development. I effectively was working directly for John when I started. We had just launched this Kickstarter campaign and my job was to get the word out to as many people in my network as possible. I think I helped sell the first five bikes that came through on Kickstarter, and my roommate and I bought one. I had my mom buy one and a couple of other friends, but we sold, I think, 188 bikes through our Kickstarter campaign.

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Rachel Star: As the Kickstarter went on and you thought about your role within the company, how did you carve out specific projects for yourself to work on?

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Ryan Engel: On my first day of paid work, we flew to Taiwan. It was me, John, and Tom Cortese [co-founder and now chief product officer]. We went to meet with our manufacturer there at the time to go green light the first production run of a bikes that we had just sold on Kickstarter.

We got to the manufacturing facility and John was like, “All right, we're ready to ship.” Tom and I looked at each other and Tom is on the bike and he's able to move the bike with his hands because the stabilizers on the bike were not stable. There was still obviously a fair amount of retooling that needed to happen before we were ready to ship.

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On that plane ride back he woke me up in the middle of the flight from Taiwan to New York, and says, “I really don't think we're gonna be a pure-play e-commerce business. I think we really need to think through what brick-and-mortar retail looks like, and I want you to figure that out. And then left me.

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This is just how John's mind works. Whenever something comes to him, he will either call you immediately or, when we're in the office, he would immediately come to your desk and tell you exactly that idea. He wouldn't sit on anything ever, which is a fantastic quality of a founder.

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Rachel Star:  I guess you had your work cut out for you, huh?

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Ryan Engel: I started crafting this kind of entire go-to-market, brick-and-mortar retail strategy. My immediate thought was to open a kiosk in Grand Central Terminal or Chelsea Market, and the concept was going to be Peloton bike, some kind of one of those signs that you can unfold that, you just set up a trade show and an iPad. That was the idea. I put together the whole business plan on the plane.

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I went to chat with Tom and our other founder and he said, “I don't think our consumer today is necessarily in New York City. I've been talking to Short Hills Mall in New Jersey. We were thinking about maybe doing a pop-up store. Why don't you go check that out?”

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I grew up on the Upper East Side of Manhattan, so I'd never been to a shopping mall until that point in my life. I drove 45 minutes out of the city to Shore Hills Mall in New Jersey. I got to the shopping center and it's the greatest retail experience ever.

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It's a 15-minute walkable experience with super-luxury brands — Prada, Apple, and Tesla, and LuluLemon. I'm like, “we wanna be around all these brands.”

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I went back and scrapped the idea of opening pop-up stores in highly photo-trafficed areas around New York and pitched this idea for a pop-up store in Short Hills Mall. I think my budget was like $10K.

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I said, “Give me a space that’s already built out, where I don't have to do anything to it, where I can just throw some signage and furniture and spikes in.” And that was the concept of Peloton retail to begin with.

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Rachel Star: It's so cool to hear that evolution. For folks who are familiar with Peloton, I think we know that the retail presence is such a big part of the business today. I'm curious at that point in time, how did you think about your role within the company? You didn't have a background in retail, so what was that like?

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Ryan Engel: Did I think that, when I joined Peloton, I was going to help expand our retail business? No, not at all. But it was my first project that John tasked me with, and then it very quickly became something I could have real ownership of.

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It was exciting, exhilarating, and then deeply depressing at times because there'd be days where not a single person would walk into the store and that was really deflating. But when you would sell a bike, it was incredible. Every bike I sold, I would call John and then he’d send an email to the entire team. It was true startup days.

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John and our other founders and engineers would come on the weekend. These were not your best bike salespeople, so to speak, but the passion and energy from every employee was there and everyone would sell on the weekends.

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To be honest, I knew when I first joined, I could be helpful to the business. I knew I could sell bikes. I just didn't know what the right channel was at the time.

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I was really excited about just working for John and being tasked with any kind of project that he wanted to put me on. And just so happened one of those first projects was that retail business, and it exploded and was super critical for the early days of the business.

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Chris Marty: This is such a perfect example of the early-stage experience as an employee — where you don't decide what you do, the business does, and you need to be comfortable with that. At this point, you’d been at Peloton for a couple years. How was your mindset around your career shaping up and what were your considerations as you thought about either your future at Peloton or elsewhere? 

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Ryan Engel: Three, four years into my journey, I was really specialized in my career and the business was really starting to grow. It was at that point where we started bringing in really experienced senior executives who had 10, 20 years of experience.

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I had only had four or five years of experience at that point. I knew it was the right decision for the business and as a shareholder in the business, so I was excited to be bringing on this talent, but my career trajectory was dampened by this idea of getting layered.

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In February 2018, I had been at the company for about four and a half to five years, and I was really close to leaving. I actually sat down with John and said, “Do you see me here for another four years?” 

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I laid out three roles that I was really excited about and John said “Those all sound great, but I wanna encourage you to forget about them. I know what you're going to do. You're moving to London and help launch the international business.” 

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And it was. It was like going back to the early days of Peloton, where I went from specialized to thrust into this massive generalist kind of role. Every day I was up at 5:30 in the morning and working until 11 at night. I was jumping out of bed every day because I was so excited. 

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And I'm so glad when I look back on that conversation with John. For months I was afraid to have the conversation with John because of what his answer might be. I was asking a pretty open-ended question: Do you see me here for the next four years?

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He could have very easily said, “no, I don't.” And that would've ended my career there. It was a very scary conversation to have, but if I didn't do the hard thing, I wouldn't have been on John's radar to become employee number one in our international business. You gotta have the hard conversation. I forced myself to get into that uncomfortable place and it resulted in this massive unlock in my career.

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Rachel Star:  It's almost like you had that experience of being an early employee twice within the same business. What advice do you have for folks who are early in their career and looking at your path and thinking, “That's what I want to do.”

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Ryan Engel: I don't pretend that there was not a massive element of luck, in my choosing to join Peloton. And it's really hard to have that outcome — most startups, in the world of venture, fail.

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People are incredibly important, especially in the pre-seed journey. As much as I was betting on the idea of Peloton, I was betting on the team as guys who were really going to figure this thing out. Picking people is really important at that early stage if you really want to go join a startup.

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My other piece of advice is when things get really hard in your role or within the company, try to exhaust every kind of lens that you're looking at that problem. I was really close to leaving many times when it got really hard.

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It was at those moments that I really just tried to dig in. I think people underestimate the switching costs that happen; tenure is a really powerful thing.

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When things get really hard, that's actually where all the growth happens. And you don't realize it in that moment, but I promise you'll realize it if you choose to stay and stick it out. Two years later you'll say, ‘Thank God I decide to stay.’”

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I look back at that inflection point, at year four, when I really wanted to leave and I had that conversation. So much growth happened in that six months that, if I didn't have that conversation, didn't stick it out, it would've been a terrible mistake.

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Rachel Star: To flip to the other side of the table for founders or hiring managers who are looking to build their early team, what type of person do you think makes a good fit for an early-stage company?

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You have to be really good at the lane you're swimming in whether it’s product, engineering, sales, marketing, BD, whatever it may be. But the expectation should be that you're going to be wearing a lot of hats, right?

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I think back to the early days of Peloton when our backend engineer was coming to the store in Short Hills and helping me sell bikes on the weekends. You want folks who are going to be all in and excited. It's incredibly stimulating work in those early days, and you've just got to be doing it for the right reasons and making the sacrifices without actually talking about it.

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Rachel Star: What an amazing run you've had at Peloton. What are you up to today?

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Ryan Engel: I'm super excited to take my experience as a operator and apply that to investing full-time. I am going to be in the process of kicking off my fundraising now actually raising a $25 million early stage–focused fund to invest into consumer and enterprise businesses broadly. I would say connected hardware, software businesses will definitely see a lot of those and health tech as well.

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I think we're in a really interesting period in the ecosystem in general. You're seeing this pretty massive talent unlock that we haven't seen in a very long time.

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Some of the big technology firms have had this stranglehold on the top engineering talent. As we go through this cycle of folks leaving, I think there's gonna be this incredible time of new things that are getting started and folks that have been percolating ideas.

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To be an investor over the next 12 to 24 months, it's gonna be an incredible time. The firm's called Cade Ventures. And I'm really excited about it.

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