Riding the Wave: Helaine Knapp with Pau Sabria
Helaine Knapp, founder and former CEO of CityRow, chats with Pau Sabria, co-founder and CEO of Remotely on episode 106: Riding the Wave.
In episode 106 of Venture Everywhere, Pau Sabria, co-founder of Remotely.works—a platform helping companies hire software engineers in Latin America—talks with Helaine Knapp, founder and former CEO of CityRow, a rowing fitness franchise that was acquired. Helaine reflects on how her career in tech startups at Buddy Media and Olapic gave her the foundation to build a brick-and-mortar fitness business. She discusses writing Making Waves, using brutal honesty to tell the entrepreneurial story most founders won’t share, and navigating the in-between as host of Step Into Next, a podcast about walking together from what was to what’s next.
In this episode, you will hear:
Adapting startup playbooks to the physical fitness business model
Insights into the rise and fall of Connected Fitness, and lessons learned
The power of honest storytelling during a company’s challenging exit
The real challenges of entrepreneurship: navigating legal battles and team dynamics
Reimagining success and personal growth while transitioning between ventures
If you liked this episode, please give us a rating wherever you found us. To learn more about our work, visit Everywhere.vc and subscribe to our Founders Everywhere Substack. You can also follow us on YouTube, LinkedIn and Twitter for regular updates and news.
00:00:04 VO: Everywhere Podcast Network.
00:00:14 Jenny Fielding: Hi, and welcome to the Everywhere podcast. We’re a global community of founders and operators who’ve come together to support the next generation of builders. So the premise of the podcast is just that, founders interviewing other founders about the trials and tribulations of building a company. Hope you enjoy the episode.
00:00:32 Pau: Welcome to the Venture Everywhere podcast. I’m Pau Sabria. I’m one of the founders of Remotely.works, where we help companies get software engineers in Latin America. And I’m here with Helaine Knapp, welcome.
00:00:45 Helaine: Thank you so much for having me. What an exciting conversation we’re about to have.
00:00:51 Pau: I’ve personally known Helaine for a very long time, and I’m very happy to have her today on the podcast. This will serve as a personal catch up, so it will be great to know what you’ve been up to as of late.
00:01:03 Helaine: Brief introduction before we take it 15, almost 20 years back. I am the founder and CEO of a company called CITYROW in the fitness space. Had a really, really awesome 10-year build that I’ll talk about in a little bit. I’m currently in between projects, which is really interesting.
00:01:23 Pau: You’re currently living in Austin, Texas, but you’re originally from New York. Tell us about your background and growing up and how you got to meet the best founder ever, aka me.
00:01:34 Helaine: Honestly, it was definitely the highlight of my career. I’m a New Yorker. I started my career actually in magazine publishing. I was one of those infamous Conde Nast interns that was worked to the bone for $28,000 a year.
00:01:50 Helaine: Learned a bit about the ad sales world before finding my way into tech startups and was really fortunate enough to be at the forefront of helping brands understand social media.
00:02:02 Helaine: 2010 is when I first got into the space. I joined a company called Buddy Media, one of the fastest growing tech companies in New York at the time. I got to wear a bunch of different hats from project management to accounts and watch that industry grow and really was at the forefront of social media marketing, Buddy Media was.
00:02:25 Helaine: I was there for two and a half years. It was an insane ride. We sold to Salesforce.com in summer of 2012. It was an unbelievable exit. It was such a fun ride, but we all know with acquisitions, things don’t always work out perfectly for the team. I lasted six days at Salesforce.com.
00:02:45 Helaine: I was a youngie with a ton of energy. I went to a mutual friend of ours, a boss, a mentor of mine, Dan Reich. And I was like, Dan, I’m not going to make it at Salesforce, what do I do? He’s like, I’d love for you to meet these three guys that just got out of Columbia Business School. They have something really cool.
00:03:02 Pau: You then went into Olapic, into my company, and you did a fantastic run. I remember talking to Cabo, one of my co-founders, and saying, I don’t know how we pulled this off, but we just hired someone awesome.
00:03:14 Pau: What a lot of people have later come to me and asked, why did you build in New York and so on and so forth? I think that a big chunk of the success of companies comes from recycling people that have seen it before.
00:03:27 Pau: We implemented tons of things. I would go to you and say, “hey, Helaine, what should we do here?” And then you said, “well, at Buddy Media, we did this, this, this.” “That sounds like a great idea.” And so you then decided at some point to leave us. What triggered that itch?
00:03:43 Helaine: It was never something that I was actively exploring. I actually was really happy in my career. I love sales and client services for tech companies. I’ll play this game all day long. I think we were in the hottest industry ever at the time.
00:03:56 Helaine: Pau’s being very humble right now, but Olapic was really cool. For me, coming from a company that had tons of bells and whistles and probably the best PR of any company I’d ever been a part of… and I still think that what they did at Buddy Media was some of the best PR ever.
00:04:12 Helaine: But then you start to peel back the layers of the business and there were challenges from a technology perspective. The second I saw Olapic, I was like, well, this is beautiful. I was like, if you’re telling me you put this technology on the product detail page of every single company, we can’t get out.
00:04:27 Helaine: I fell in love with, not only the stickiness, but the vision. You were just such a fun, collaborative CEO that I think one of the things, you are very self-aware and you had a very clear understanding of what you knew and more importantly, what you didn’t know.
00:04:41 Helaine: You really allowed me to come in and help be a part of shaping Olapic’s future. It was really, really, really fun. I remember coming over to your desk multiple times, you being like, “so how did you do this?” That story resonates very clearly for me.
00:04:55 Helaine: On the personal front and how I ended up starting CITYROW is by complete happenstance. I became a big fitness junkie, working out a lot. I was a bit of a chubbier kid growing up so fitness became something that was really important to me.
00:05:08 Helaine: After being in that space for a while, I found myself very injured. I was confused about it. When Pau first hired me, I think I had a back brace for a while.
00:05:19 Pau: You had a personal affinity towards the company, which then pushed you into this inner feeling of I have to do this and it’s now or never or something like that?
00:05:30 Helaine: Exactly. I actually felt like the timing was terrible because Olapic was on this insane upward trajectory. I had just brought on board some of the people that would follow me everywhere. All of a sudden, I was at this moment where I was like, I have to do this thing now, the moment in time in the industry.
00:05:46 Helaine: But at the same time, I remember my dad being like, “what are you doing? You have this amazing career ahead of you in enterprise SaaS.” He was finally like, I got this kid off the payroll and now you’re going to go open a brick and mortar location in fitness and you know nothing about it.
00:06:01 Helaine: But, I had one of those moments where I was like, you know what? I think I could always go back here and I have to try this thing or I’ll regret it forever. So I think I quit probably 12 years to the day today.
00:06:16 Pau: At least I know from on my end, when I went into starting Olapic, I had all these visions of grandeur. Like, oh, this is going to be amazing and all the things. Then life hits you in the face big time.
00:06:27 Pau: I went into entrepreneurship having no clue whatsoever about anything, whereas you at least had the experience of having seen other companies scale to some degree, obviously with Buddy Media with a very, very big degree and a very big exit. How was it for you building the company? What surprised you of the path of CITYROW?
00:06:47 Helaine: There were surprises at every turn. There’s a part of me that wonders what it would have been like if my first entrepreneurship journey was in the tech space, because that I think I knew very well. And as a result of that, I actually applied a lot of tech rules to a brick and mortar business that didn’t always make sense.
00:07:05 Helaine: But it’s what I knew, even the fundraising and thinking about the cap table and the payback. It would have made a lot more sense if it was actually structured kind of like a restaurant in the beginning, in that first entity.
00:07:17 Helaine: It gave me the confidence in some way. I think working in all these startups to know that I could wear a lot of different hats and that I was a bit of a jack of all trades. I could bet on myself to problem solve because I’d seen myself do that over time. And so it really gave me that foundation.
00:07:31 Helaine: But man, was it a total shit show at every turn. It was so insane. And I felt like there actually weren’t enough people talking about how hard it was that I wrote a book, Making Waves, about the CITYROW journey, because people need to be able to see with a little bit of a deeper level of vulnerability how hard it is.
00:07:53 Helaine: Everything from lawsuits to people that you thought were good friends suing you, to challenging investor conversations, to telling the board that you’ve run out of money and you have to shut down, to throwing Hail Marys, to learning crazy structures.
00:08:09 Helaine: We got hit with some crazy winds, particularly as COVID hit an emerging brick and mortar fitness franchise that also had a Peloton-like business to it. I think back and I’m like, how was I building all those businesses at the same time? And also, how did I survive?
00:08:29 Helaine: But it was a crazy journey. I told the story in a book because it was cathartic for me. It was the ride of a lifetime.
00:08:36 Pau: In that catharsis, I guess that you were thinking about the next phase. The beginning of the podcast, you were talking about you’re in this in-between phase. Was there, to the book, something more than just a venting out or was it more about a stepping stone toward what you may be doing next?
00:08:54 Pau: You, Helaine, have been one of the people that I’ve known that have this always positive energy. Everything was energetic. I can see how someone faces that, gets punched in the face, stands up and then goes back at it again.
00:09:05 Pau: Even throughout the different struggles that you’ve shared with me about building a company, you always found a way to pick yourself up and just go against it when a lot of people would have quit. What are you trying to do with this?
00:09:17 Pau: Which, by the way, I find it super amazing. Put yourself out there again with a book, which is, again, difficult to write. You have to promote. Then this is the hyper competitiveness. But business books without an audience necessarily, it’s hard to pull off. So what was that like?
00:09:35 Helaine: The resilience is definitely there. When it comes to the book, the initial impetus was COVID and I was really bored. I had someone working for me that was an author and she got to know me really well. She was also a fellow fitness founder.
00:09:53 Helaine: She was like, you have amazing stories. Let’s tell the stories. She’s like, you’re also a really good storyteller. I think it’s time to write your book. I was bored. We were all in lockdown. I was like, okay. Fine. If you want to listen to my stories, I love talking. Let’s go.
00:10:07 Helaine: I wanted to tell the story of CITYROW right before we had raised our series A because I thought that I read so many books and I listened to so many podcasts of How I Built This, that when you’re telling this story after the event, things are jaded.
00:10:26 Helaine: I knew so many founders that had gone through an exit and things were either they had golden handcuffs, they hated the company or they were fatigued on it. And also the second half of the story always got a little bit more spotlight. And I thought it was important to tell the early sides of the story. I was like, okay, that’s cool.
00:10:45 Pau: The scrambling at the beginning.
00:10:47 Helaine: Yeah, those are interesting. That scrappiness, I thought was always really fun and it was much more creative. So I was like, let’s tell a story. Startup to series A from the perspective of a founder that hasn’t made it yet, but probably will… was the initial impetus.
00:11:02 Helaine: And then as COVID started destroying our business and negatively impacting every single aspect from employees to franchisees to our subscription model, to our investors, I actually pulled the book and I was like, this is a dark book.
00:11:18 Helaine: We’re going to go dark. I want to tell the underbelly. I want to talk about the board meetings where I cried. These are the things that actually are happening. If I’m going to tell the real story, I want to cry and tell people about it because that’s actually what happens and no one’s telling that story.
00:11:34 Helaine: Then to your point, I actually started writing the book almost in real time. We already built out the first framework of, okay, here’s the initial story. I was able to tell what was happening in real time to my book collaborator.
00:11:47 Helaine: That was cathartic to be able to process in real time and then weeks or months later go back and be prompted to be like, well, how did you feel in that moment? I was like, that was horrible. It was one of the worst moments of all time.
00:11:58 Pau: It’s interesting because… well, for one is when people ask me what it was like, I tend to remember more of the struggles than the part where it was more like the… more repetitive. Your brain smooths it out all as a big chunk of just going to the office.
00:12:14 Pau: Whereas at the beginning, when you’re really, really struggling and you have to come up with creative solutions for things, those are the things that you remember. The team is smaller. You remember the people. You can tell the story much better.
00:12:26 Pau: It seems like in your case, it was throughout the company was like that. It was at the beginning, maybe because it was fun. You were creating something from scratch. But then as COVID was making your company implode, it stayed that way in terms of uniqueness of the situation.
00:12:41 Pau: After you published the book, have people come back and pointed their fingers at you for things that you said about crying in a board meeting? Has there been a consequence to that or did you think about that? And if I go out and publish these things, will people come after me somehow after?
00:12:57 Helaine: It was definitely something I was worried about, particularly with certain partners. Everyone was painted in a fair way, but I was very worried about it. I definitely had a lawyer read it for libel.
00:13:08 Helaine: There are stories that did not make it in. There are stories that involved legal that I was not allowed to talk about that I think were really important. For instance… we’ve all had this, the disgruntled employee who was fired, thinks they shouldn’t have and comes after you.
00:13:23 Helaine: So that was one of the worst experiences I had as a CEO. Couldn’t talk about that. Couldn’t talk about intercompany relationship that shouldn’t have happened. Couldn’t talk about that. Couldn’t talk about the lawsuits with landlords. And so I really did pull those things out.
00:13:40 Helaine: But I was worried about it. At the same time, one, not everyone’s going to read your book. It was hard. I even thought about you guys. I was definitely working both jobs for a little while and I was worried. I had so much guilt about even the nights and weekends that I was working on CITYROW while working for you.
00:13:58 Helaine: Now, that’s a little bit of a me issue. I also knew at the same time that I was doing a fantastic job. But there was a lot of emotion that went into a lot of different pieces to it. And yes, I was afraid of what people might think.
00:14:09 Helaine: But at the same time, I felt stronger that people were going to resonate with the story. That kept me going alongside what you were getting to earlier, which is that subconsciously the book project gave me a beacon of light to look forward to when I knew that CITYROW was going to end.
00:14:30 Helaine: CITYROW threw us for an insane curveball. It basically killed all of our franchisees. We had sold 70 and opened 11 in the… three months before COVID hit. Our digital business, it was booming. But Peloton, that was at an $8 billion market cap. There was a massive Connected Fitness hangover. We hit the same tailwinds.
00:14:51 Helaine: I knew that it was going to end and that I could be depressed. So I think that the book was a project that I kept at. One, a lot easier than I thought to write a book. But then the CITYROW landing of the plane took a ridiculously long time. Our acquirer pulled out after six months of Latham and Watkins on the closing call.
00:15:11 Helaine: I had to email my publisher being like, hey, I have a material change to the end of book. She was like, you can change these three pages. I was like, okay, but the book coming out five months after the actual acquisition, sure. This is a tragedy, the story of CITYROW in a lot of ways.
00:15:28 Helaine: But I think the book kept me from going into a depression. It gave me a project that I probably subconsciously kept going, knowing that it was something to celebrate. I remember when I decided for myself a book launch party, I had this duality and I know this is not true. I recognize this.
00:15:46 Helaine: But there is a natural feeling of a failure when the thing that you’ve been working on for over a decade does not succeed in the way that you thought it would. I had a lot of issues with that because I very much stand by my word. I told people that this was going to be successful. And then it wasn’t. That was very, very hard for me to grapple with.
00:16:04 Helaine: I forced myself to celebrate the book as a bit of a relaunch. And it really, really helped prevent a depression.
00:16:12 Pau: And now you have a podcast. Are you building a media company? Is that the new Helaine? Are you coming up? Was the CITYROW your cocoon? Is this now the new blossoming of a new flower? Is that what your strategy is? It’s like going through the dark ages and coming out on the other end?
00:16:29 Helaine: Yes. I launched a podcast last year. It’s called Step Into Next. It talks about the liminal space in between when something really big ended and the next thing hasn’t yet started. We want to normalize what it feels like to be in that space before you step into what’s next.
00:16:44 Helaine: I definitely plan on coming out of the other end. I think maybe I already have. I’m actually not even sure I went into the dark ages. Part of what I’ve been trying to do is just keep myself interesting and interested during this period of time.
00:17:00 Helaine: It is so much harder than I thought it would be to be in between things, especially when the thing that I did for a decade, I was really proud of. I loved answering the question, what do you do? It was interesting. It was engaging. I had agency. I could use my creativity.
00:17:17 Helaine: And then all of a sudden I’m thrown out into the real world and have to start from scratch. It has been the hardest thing I’ve ever had to do. In some ways, harder than CITYROW.
00:17:27 Pau: It’s funny, because when you say about it, I remember having this conversation with Luis and Cabo, my co-founders of Olapic. Part of our worry after the acquisition was, what are we going to tell our kids that we do now? It is part of the drive that pushed me into building other things. And so how are you tackling the ”what’s next” now?
00:17:48 Helaine: I didn’t have the luxury of waiting or thinking because, spoiler alert, CITYROW was not a win. I put everything I had into it. When I asked investors to throw the Hail Mary and put their last 25K in, I put my last 25K in.
00:18:04 Helaine: So I had to very quickly turn around and make sure that I had some consulting work to pay bills. That was just a forced entrance into consulting that I didn’t have a choice. I was like, okay, what can I do? What are my market values?
00:18:20 Helaine: I ended up doing a lot of consulting with friends and stepping into roles that I knew I could do in my sleep because I was really burnt out. I gravitated towards people that were building cool things that I could be supportive in. I learned what I didn’t want to be doing.
00:18:35 Helaine: I know I probably can’t work for that many people. I learned that I need to be with other A players. I don’t like being the smartest person in the room. That’s for sure. You can get paid to do that. But I don’t love it.
00:18:49 Helaine: I don’t think I’m necessarily building a media company, but I do think that I’m trying to surrender to what’s coming my way and why. I’m not exactly sure what’s going to happen yet, but I don’t have the idea yet. The CITYROW idea came to me by accident. So I’m not going to try and force something. In the meantime, I’m dabbling.
00:19:11 Pau: For what it’s worth, maybe it’s the European approach to it, but I decided that I think that ideas need to grow over time. What you need is to create a field in which you can plant a few things and water them from time to time and see and take a much more patient approach. The ones that grow and compound in your head then magically get better the more you look at them from different lenses.
00:19:34 Pau: Those are the ones that eventually self-select themselves into being pursuable ideas. It’s something that when I force the machine, like saying, “oh, this now,” especially hurried, those tend not to work as much.
00:19:50 Pau: I see the podcast, the book as a way of not only keeping yourself busy, but at the same time, putting yourself out there to maximize serendipity and create an audience. All of those are pillars that you’ll for sure use in some way or fashion when that idea comes back into life.
00:20:13 Helaine: You’re spot on. That narrative of patience and nurturing the ideas is something that I wish I saw more of out there in the world. I think it’s part of why you’ve been so successful, is that you’re methodical as a founder. I actually think it’s a very rare quality.
00:20:32 Helaine: A lot of us are a little bit more like Cabo. We run a million miles a minute. You always had a slightly different energy, which I think made you very unique as an early stage founder and CEO.
00:20:44 Pau: I think you need that nuclear engine of an energy. I’m more of a sloth. I move with very few movements but those have intent.
00:20:52 Helaine: Totally. I could wear a little bit of that hat, like I have a very high EQ. I can be patient. I can listen. It’s an interesting place to be in that post exit, whatever the exit looked like. Any one of our fellow founders who’ve been through it have probably a lot to say.
00:21:08 Helaine: I think for me, given how CITYROW ended, it’s taken a long time for me to thaw out. I don’t think it was until this past summer, which was a year and a half after the final handoff, that I was like, oh, am I bored? That’s so interesting.
00:21:24 Helaine: And then, you know, there’s this recalibration of like, okay, well, what are my best gifts out there into the world? Then there’s a retraction of just like, well, a random company doesn’t just get me. I’m like eight people. I can have eight jobs. I was like, do I just take multiple CEO jobs kind of like Dan Reich and see what happens?
00:21:44 Helaine: So there’s a lot that goes on in the post founder CEO conversation with yourself about what to do. Then there’s this element of like, well, if I just got a real job, am I failing? Am I settling?
00:21:57 Helaine: I’m going to probably offend people when I say this. But is that boring to get a real job? I was like, should I go work for like Sequoia and do investing? I want to talk about that, though, because I think it needs to be.
00:22:08 Pau: It’s great someone is bringing those types of conversations and authenticity. It was already true back in the age of user generated content that we proved that authenticity was good. Now with AI, it does feel like every day, is this really true?
00:22:21 Helaine: Should we run Olapic back? Is it time for a resurgence?
00:22:24 Pau: Maybe. It’s great that you’re taking these steps. As a former investor of CITYROW, I’m happy to see you alive and kicking and giving a second chapter to Helaine Knapp.
00:22:37 Pau: We’re going to end with a speed round of questions. What book you’re reading or podcast that you’re enjoying?
00:22:45 Helaine: I love the Surrender Experiment. I can’t listen to that enough. If you have not read or listened to that by Michael Singer, I thought it was the most life changing book that I read in the past year. I’m also obsessed with the Acquired podcast. It’s just four to five hours of learning crazy things. Coca-Cola, Trader Joe’s episodes. Can’t get enough.
00:23:05 Pau: If you could live anywhere in the world for one year, where would it be?
00:23:09 Helaine: I’d probably live on the beach in Tel Aviv.
00:23:12 Pau: Favorite productivity hack?
00:23:14 Helaine: I’m obsessed with Wispr Flow.
00:23:16 Pau: Me too. I started last week. I stopped typing. I just yell at my phone.
00:23:21 Helaine: Me too. I DM the CEO being like, “Yo, we’re onto something. Do you want to hire me?”
00:23:26 Pau: I’m going to make sure that the show notes have my referral code.
00:23:29 Helaine: My referral code too. They can choose. We’ll see who did a better job based on the referral codes.
00:23:34 Pau: Where can listeners find you?
00:23:36 Helaine: I’m all over. Helaine Knapp on Instagram, LinkedIn. My book Making Waves is available on Amazon. I also narrated the audio version if you just can’t get enough of my voice.
00:23:48 Pau: So we’ll end the episode with probably the most weird ending anyone has ever heard in this show, which is I’m going to dedicate the last few minutes to Helaine’s mom. When Helaine was my employee, I would send report cards to Susan telling her how much of a great job Helaine was doing. I’m going to tell Susan that Helaine is doing fantastic and that I’m very proud of her and that she should be too.
00:24:18 Helaine: That’s adorable. Thank you, Pau. This is awesome.
00:24:23 Scott Hartley: Thanks for joining us and hope you enjoyed today’s episode. For those of you listening, you might also be interested to learn more about Everywhere. We’re a first check pre-seed fund that does exactly that, invests everywhere. We’re a community of 500 founders and operators, and we’ve invested in over 250 companies around the globe. Find us at our website, everywhere.vc, on LinkedIn, and through our regular founder spotlights on Substack. Be sure to subscribe and we’ll catch you on the next episode.
Listen to more from Pau Sabria on the Venure Everywhere Podcast episode 31: Remotely Engineered.