NFT Strategizing – Ryan Duffy

Ryan Duffy:
The biggest missed opportunity was the NFT platform. I’m embarrassed to say that because I’m so not an NFT guy. We were super early to this market that got absolutely massive. We were super well positioned. Definitely would have been ripe for a big acquisition. When stuff was really peaking, we missed the boat. So it’s nice in one way that we like had the right idea, but we folded too early. So that was tough.

Ryan Duffy:
But it is what it is. I don’t think a whole lot about, oh, it could have been one step at a time, just taking it as it comes and not worried much about what happened before.

Dana Robinson:
Exit Plan is a podcast for business owners and those who want to be business owners. I’m always in search of the lesser.

Dana Robinson:
Known stories of entrepreneurship.

Dana Robinson:
In the exit Plan podcast, you’ll hear stories from startup to sale and hear from the professionals who helped business owners achieve their exit. Hosted by me, author and private equity manager Dana Robinson, along with my co hosts and guests, you’ll hear real stories, tips and tools that will help you plan for the exit you want, whether you are still working at a day job or running a business. Let’s get started with this episode of the Exit Plan podcast.

Ryan Duffy:
Our last company, audio company, we had all these podcast producers come work for us and they said, always keep an apple. When you’re recording a podcast, nature is like, gets the juice flowing. It really works.

Dana Robinson:
Really?

Ryan Duffy:
I always have one now.

Dana Robinson:
Does it just, is it just thinking of the apple makes your mouth water and gets the juice flowing? Or do you need to actually take a bite of the apple like you just did?

Ryan Duffy:
It’s just like, no, it’s not thinking about it. It’s, you know, right before you start, you want to lubricate. You want to lubricate the voice, lubricate the mouth.

Dana Robinson:
I love it. That’s great. That’s for. I’ve done some audio productions from my own books, and my partner Corey’s been in audio production since our first venture together over 20 years ago. Have not seen any apples sitting around the studio, so I’m going to take that one to him. The everyone you’re entering this podcast in the middle of a morning of me eating oatmeal and Ryan Duffy from American in England at the end of his Tuesday afternoon having an apple before our podcast interview.

Ryan Duffy:
Hello.

Dana Robinson:
Thanks for coming on at the end of your busy day. I’m sure I’m excited to get your story because you’ve been through multiple cycles of entrepreneurship and businesses that have gone through the sort of evolution that I think is always instructive for other people to hear about that journey. And I’m excited to hear it myself because, you know, you and I have connected on your latest venture, which is in skunk works mode, and we probably won’t talk much about it, but I love to get what got you here. How did this all begin? What’s the origin of the Ryan Duffy story?

Ryan Duffy:
Definitely. Well, I’ll start at the very beginning. I’m born and raised in Miami, alumni of University of Miami, and my first job coming out of college was in Hollywood. I worked for a talent agency called WME. It was actually called a William Morris agency at the time. That’s how old I am. They later merged with another agency called Endeavor to become WME, which is probably what your listeners will know it as today. And that was a crazy first job.

Ryan Duffy:
It was kind of almost out of a book. I got hired as the assistant to an agent called Ed Lamotto, and Ed was sort of the last of the great Hollywood agents from a different era, you know, sort of living old Hollywood glamour in a way that doesn’t quite exist anymore. I was his third assistant, so he was about as successful as it gets. He was previously the president of an agency called IcmDhdem, one of the other big four at the time, and he came over to William Morris, needed a new third assistant. I was in the interview process to get into the mail room, so people have probably heard of the mailroom before. That’s sort of the proving ground for Hollywood agents, where you cut your teeth and get hazed. And they plucked me out of there. I’m not entirely sure why, to have me interview for Ed’s desk.

Ryan Duffy:
And I got to skip the mailroom, which most people don’t. So that was kind of lucky. And I got thrust into a really crazy world. He represented some of the biggest movie stars in the world, and we were working on the biggest movies in the world.

Dana Robinson:
Wow.

Ryan Duffy:
And, you know, the first thing I did or the first thing I learned my first day on the job was how to feed his shark in his shark tank in the office by hand. That’s like a shorthand to give you a sense of what that life was like. And it was. That was an amazing time. I was there for a couple of years as an assistant. I moved my way up all the way to the number two assistant at some point and got a little bit closer to the business. And what I learned there and what I’ve taken away and still think about after all these years is two things. One is client service.

Ryan Duffy:
So the agency business is the ultimate client service industry. Your clients are the most famous, the richest, sometimes the most entitled people in the world, for better or worse. And no is simply not an option. And that’s kind of a trite phrase. Everyone in sales or customer service says that it really is not an option in that business. And the level of service and attention to detail that you’re taught inside of an agency like that, working at the very highest rungs of the entertainment business, it’s like no other. So I compare it to the best banking firms. You will get reamed if there’s a misplaced comma on a financial analysis deck when you’re a junior analyst.

Ryan Duffy:
I don’t support reaming, but it does instill something in you that maybe a less pressure forward environment would not. And that is crazy. Attention to detail and always serving the clients. My boss, Ed, said agenting was about turning a no into a yes. That’s how he boiled down the entire job. And, you know, I can apply to any business, and I still take that one with me, too.

Dana Robinson:
So that’s amazing. That’s what, out of college, you got put into the crucible and taught some valuable lessons by people who did not care to coddle you.

Ryan Duffy:
No, there’s no coddling happening inside of those walls. You know, it might be a little different today. Hopefully it is. You know, Ed was actually great, and, you know, not at some cartoonishly villainous boss like you would see on entourage.

Dana Robinson:
In spite of the shark.

Ryan Duffy:
In spite of the shark, exactly. So it was a great experience, a really lucky one. You know, his assistants who had graduated into the business over the years all have a little bit of a fraternity, so, you know, it’s sort of a built in network that I inherited just by sheer luck. And, you know, I never wanted to be an agent or work in Hollywood specifically. I kind of, you know, I did good in college, but wasn’t the person with an internship every summer who was just on some laser focused track to get to a certain place? I actually had no plan at all and kind of happened into it and got lucky. Didn’t know anyone in Hollywood, but kind of knew somebody who knew somebody. And I heard those were cool and fun places to work, and I was like, okay, I’ll try that out. And it worked.

Ryan Duffy:
So spent a couple years there and then moved to a smaller management company, same idea, but more intimate environment, working with big movie stars. Angelina Jolie, Nicole Kidman, Billy Bob Thornton. Our company produced the first series of Fargo, which won the Emmy that year, which was very cool, and then moved back into the agency world at a company called UTA, which is sort of one of the big three, like WME, and got to work with Al Pacino and Harrison Ford and I, Ewan McGregor and a bunch of other very fancy people doing some of the same work that I was doing before just at a little bit of a higher level. And ultimately, that business is a grind. It’s fun in a lot of ways. It’s glamorous in some ways, but probably not as glamorous as most people would think it is. It’s kind of a hard existence when you’re in client service. At that level, your life is not your own, and you also have no ownership over your own business, so your clients are not yours and they can fire you any day.

Ryan Duffy:
So there’s a lot of insecurity that runs rampant through that world. It’s a little bit like high school, where people from the next company down the street or even the next office down the hall are talking to your client and you’re feeling a certain type of way about it. And that’s just like, not a way that I want to be or I want to live. So I had a goal this time, and I wanted to move out of the agency world, move away from Hollywood, which generally was already a contracting business at that time and has really contracted since then. I wanted to move into consumer tech. I saw a lot of opportunity there. I’ve always followed consumer tech, and I was looking for companies where I could apply this skillset of client service, a network of relationships in Hollywood. And I met the team at a company called Vidme, which was a social video platform in around 2016.

Ryan Duffy:
And they just raised a series A about $9 million off of some very impressive growth inside of the Reddit community. So basically what Vidme was, was the easiest way to share video online. It’s hard to remember this, but back then, Facebook, Reddit, Twitter, Instagram, you couldn’t share videos natively. You couldn’t even do it on sms, on text message. So Vidme basically solved that problem. It was the most frictionless way to share video on any platform or over text, if anyone’s heard of Imgur. Imgur, they kind of solved the same problem for Reddit before it even had native photo sharing. It really took off.

Ryan Duffy:
And after the series A, the goal was to sort of pivot Vidme away from being mere utility into a native platform for creators, one where they could build an audience and monetize their content and importantly, monetize it in new ways. So at the time, if you were a youtuber or video creator, the only real way to make money was by ads, YouTube Adsense. Now, Patreon did exist, so you could have a third party subscription service over here, but it wasn’t integrated into the platform. So that degree of abstraction came with a lot of lost value. And, you know, creators back then would have to funnel their followers and fans from one platform to another. And there’s just, you know, it’s friction. So we wanted to build those tools natively into the player. And my job when I came aboard was to basically kickstart the community.

Ryan Duffy:
So acquire notable creators from YouTube or Twitch or vine was big at the time, and get them to start publishing on bid me, because our goal was to create a destination for viewership as well as a platform for creators to monetize and grow their business. So I started by myself, basically cold calling youtubers. I had some connections via my last jobs to talent managers and agencies and stuff like that. Really, most of it came from just cold calling people, figuring out the pitch for bid me what made us different. Why would anyone want to either move from YouTube, which really was not a realistic proposition. YouTube was. You’d be stupid to move from YouTube then and now. So it was really about convincing people of the opportunity to syndicate their content on vidMe.

Ryan Duffy:
To kind of grow an audience in a new place, use that as an insurance policy. Sorry, hold on. To grow their audience, please edit that up. To grow their audience in a new place, kind of use it as an insurance policy should their account be taken down and their content taken away, to use it as a more native seeming Patreon where they could drive their biggest fans to subscribe directly to them. So it sort of became a destination for premium content for a lot of people who continued to use YouTube. And it started to work pretty quickly. We did some silly marketing stunts that got us a lot of attention and kind of turned that very manual outbound process into an inbound one. The biggest thing was it was on Reddit, and again, that’s where we first found traction as utility.

Ryan Duffy:
I won’t get too in the weeds, but at the time there was this thing called the YouTube adpocalypse. Basically, YouTube was demonetizing a bunch of creators videos. All the creators were mad at Mommy and Daddy, at YouTube. It was a lot of drama. So that was good for us. We sort of seized on that opportunity. We made this video kind of speaking directly to that audience of disenfranchised youtubers and we touted Vidme and that video went to number one on all of Reddit. I don’t know if that’d be possible today because Reddit’s about 100 times bigger.

Ryan Duffy:
But even back then, it was still a pretty huge deal and we got massive, massive inbound. So that kind of changed everything for the business overnight. I remember staying up, I stayed up all night that night, just replying to emails, helping people get onto the platform. And it was like that for weeks and weeks after. So for a while, it was the kind of cool YouTube alternative, not like a gross right wing crazy one like that, that’s really fringy or conspiratorial. And if you’re into that, that’s cool. I’m not. That’s not what we want it to be.

Ryan Duffy:
There’s actually a great business there, it turns out, because other platforms have done, well, kind of seizing that audience, but it was a place where youtubers could come and genuinely make some money and genuinely build a new audience. And it was working. But there was one very important problem, which is it is about the most capital intensive business you could possibly imagine starting, when you’re processing and storing hundreds, thousands, hundreds of thousands, millions of hours of hd video in perpetuity. You know, as we grew, the infrastructure costs grew and unfortunately, we just couldn’t reach escape velocity. To use a really tired bit of startup jargon, it just, it just wasn’t going to be possible. And same thing happened to the original YouTube. They were also mired by a lot of lawsuits from record labels and media companies. We didn’t have that problem, at least yet, but it was really about infrastructure costs and the same forces that started this YouTube adpocalypse, which was basically to boil it down, an increased concern around brand safety for user generated content from the biggest ad buyers in the world, mostly the agencies that represented Fortune 500 advertisers that worked against us because our platform, just by virtue of being newer, smaller and less sophisticated than YouTube, had even fewer tools to capably moderate all of the content that was coming on board, did a pretty good job.

Ryan Duffy:
There was just an industry wide allergy to user generated content at the time. And ultimately, the only way Vidme would have worked was by monetizing via ads. So even though we started helping creators monetize differently, that was the path to success for the business as it is for really any video or media platform that’s not a subscription service. We ultimately sold Vidme to Giphy in an asset sale. So that allowed our team to stay together. We did not go in house at Giphy. Giphy was soon after gobbled up by Facebook or meta, and we sold a bunch of money in the bank from our previous fundraise. So it was about.

Ryan Duffy:
We found ourselves in a really interesting position where we had money but no idea. It’s like the opposite dilemma of every entrepreneur. And we took months trying to figure out what we would do next. And, I mean, we were, it was like everything. If you remember that, you know those face masks that, like, moisturize your face, they look like little, like a little paper plate you put on your face. They were really hot at the time, and we were like, oh, like, let’s do our version of those. But they’re for guys, this is just like, whatever. But we, you know, we took these ideas seriously and we.

Ryan Duffy:
We kind of ran them down. I’m glad we didn’t do that one. We thought about, gosh, home Std tests.

Dana Robinson:
Okay.

Ryan Duffy:
Because we were like, you know, people are embarrassed to go to the doctor and they don’t, they don’t want to, you know, confess that they think they might have some disease. What if we can send it to them? That seems like a good idea. Turns out it was because someone else did that and they’ve been very successful. Didn’t do that subscription Christmas decorations. I mean, just everything. Random stuff. Ultimately, what we settled on was a web three company, but it wasn’t called web three three back then. It was called crypto still, okay.

Ryan Duffy:
And it was actually one of the first NFT platforms. And so this is back in 2017 to 18, literally before anybody knew what an NFT was. I don’t even know if the term NFT, like, really existed or had been, like, adopted in the sort of ecosystem yet. Maybe it just had been. But either way, nobody who wasn’t spending their time obsessing over crypto knew what. Can I curse?

Dana Robinson:
Yes.

Ryan Duffy:
Nobody knew what the fuck an NFT was, right? But we had this idea to start this NFT company, and it wasn’t my idea. Honestly, I did not get it. I was like, what are we doing? But I was like, okay. We had toiled long enough trying to figure something out. It was different. Let’s see what happens. So we launched digital objects, and at the time, there was only a couple of these platforms around, one called rarebits, which isn’t around anymore, super rare, which is opensea, a couple others. And we were actually, you know, one of the more well known ones at the time.

Ryan Duffy:
And my job you know, before we became well known in this very small world was to get creators to publish their artwork on digital objects. And that’s one of the hardest things I’ve ever had to do professionally because I’m out there going to these artists, like, trying to explain what an NFT is. And if you think about it, it’s like, it’s digital, but, like, you own it. No one can copy it. It’s, you know, like, people are like, what? You could see their eyes roll back into their head, and a few people got it. And, you know, maybe no surprise, some of them went on to become super rich once these things exploded a couple years later because they just always saw the vision. But I ended up hiring some help. We got a consultant to come in who is at a very fancy New York City gallery that specialized in digital artwork.

Ryan Duffy:
She helped build some bridges for us, was super valuable, and we got things going a little bit, but at the time, there just was not a market to support a venture scale business, not even close. So had we stuck it out, we would have done amazing. But it just wasn’t. It wasn’t there. We were too early. It’s like the classic startup dilemma of bad timing, which you can also say was true for Vidme, because a few years later, it would have been more valuable in light of TikTok and TikTok maybe getting banned and stuff like that. So we wound down digital objects after less than a year. I think, you know, was kind of disheartening, but also validating to see the NFT space blow up a couple years later.

Ryan Duffy:
It’s like, damn, we were really onto something. Too bad. We call the quits a little bit too early, but that’s okay. It’s like, that’s what happens. You know, there’s more stories like that than the people who stick it out and, you know, end up striking gold. So the next project was a company called knowable, and our insight at the time, we’d always been interested in e learning. E learning was definitely growing fast. If you remember back then, 2018 ish podcasting was also hitting that inflection point where everybody was starting one, and definitely everyone was listening to one.

Ryan Duffy:
We just had this insight, like, okay, every course platform is video first. There’s a ton of topics you can learn that don’t require video. So let’s make the audio course platform. It’s not like the most genius idea ever, but it didn’t exist at the time, not really, at least not in a sophisticated way. So the goal was to build essentially like udemy for audio. There was an example of this in the market out of China. There was a very successful, very valuable platform called Chow Chow, I think. And basically that provided a place for subject matter experts to create content and distribute that content and monetize it.

Ryan Duffy:
And by virtue of that platform success in China, we were able to raise a seed round from Andreessen Horowitz, the partner who invested there was a consumer specialist in the chinese market. So saw some parallels and a similar opportunity in the states. And that’s what we started building. So we were suddenly in the course business creating courses. We were kind of insecure when we started about one thing, which is that at the time, no one was habituated at all to paying for audio. It was just not something that was common. And courses feel more valuable theoretically when they’re on video. So we’re making you pay for something that feels less valuable.

Ryan Duffy:
And that was a problem that we thought we had.

Dana Robinson:
Dana Robinson here plug for my book, the King’s Flyswatter.

Dana Robinson:
You can see it here behind me. If you’re watching this, I’ve got it in my hand.

Dana Robinson:
It’s a beautiful hardcover book, printed to.

Dana Robinson:
Make it giftable, something that you can share with a family member buy as a gift.

Dana Robinson:
So this latest book, it’s a fable about a person who has a really crappy job. Let’s just start there. This is a book that most people can relate to because we’ve all had crappy jobs.

Dana Robinson:
This is the story of Ubar, a.

Dana Robinson:
Servant in the court of a babylonian king who masters his boring, monotonous job and then learns to listen to the king, hearing him rule the kingdom while quietly swatting flies behind the cane. Eventually, Hubar becomes the wisest and most successful man in the kingdom. The story is fun, and it’s easy to read, but it’s not mythology. It’s my story. And as I shared the idea with colleagues and friends, I learned that it was their story. And guess what? It’s your story if you’re at a job of any kind, one that you love, one that you hate, one that’s just enough to get by. This little book gives fresh perspective on how to leverage that job to get you something greater than a paycheck. The lessons in this parable are entrepreneurial lessons, but not what you might think from the current entrepreneurial zeitgeist.

Dana Robinson:
If you or someone you know are looking for a real pathway to entrepreneurship, here’s the secret. Your job is the way out of your job. It’s counterintuitive but once you see how it works, you can’t unsee it. Learn the way of the fly swatter from the parable of Ubar and from the stories I share from my 30 year business journey.

Dana Robinson:
You can get a free copy of.

Dana Robinson:
The King’s fly swatter by going to danarobinson.com.

Ryan Duffy:
And to mitigate that, we basically tried to make these courses as long and comprehensive and dense as possible. You get a book with it, the startup course, you get stripe atlas, and you get all these little resources and tools for free. We just want to pack it with as much value as possible, which is like a good principle for someone creating a product to abide by in general. But it turned out we really overdid it because what people actually wanted wasn’t longer, they wanted shorter. And in fact, this very long runtime and just like this extra complexity was a reason for people to kind of like, say no and choose not to purchase, which we learned after not too long. So it also made it hard to recruit experts onto the platform because, you know, they had, it’s like, hey, you want to come here? You gotta write a three hour course and host it by yourself on a microphone. No one wants to do that. And, like, even people who were very fancy professors or business people and on this public speaking circuit or whatever, they would get in front of a microphone by themselves and just like completely lock up.

Ryan Duffy:
It’s crazy. Yeah, really surprising. It’s like one of the things I remember most from building that company is like, how are you not okay doing this? You do this all the time. It’s just different. People freeze. So we kind of reshaped the format, really whittled it down, simplified the process for everybody. Ultimately, it became a lot more podcast like, and, you know, that’s what started to click a little bit. And meanwhile, pandemic hits, elearning blows up like crazy, and clubhouse comes along.

Ryan Duffy:
And Clubhouse was kind of doing exactly what Andreessen wanted knowable to do. It was this like kind of viral, self perpetually growing platform of knowledge sharing and expertise. You know, literally like the coolest, smartest, most impressive people in the world were going on clubhouse every night during the pandemic. Like, you know, former CEO’s of the best companies, like Virgil Abloh, the designer and artist. Like, he was always my dream knowable teacher. He was just on clubhouse every night. I would have paid him. You know, I didn’t have enough money to pay him, but, like, it was just kind of like, damn, they’re getting for free what we would give our right foot to have.

Ryan Duffy:
And, you know, they were also an Andreessen company, so, you know, sort of, they won the audio race for Andreessen portfolio companies at the time. And, you know, we did okay, but it just definitely was not comparable growth wise. So we were in a position to maybe raise the next round or run an acquisition process, and we went with the ladder. We’re actually kind of a little burnt out on knowable. It was a lot of work and, you know, every startup is, but I think collectively we were all sort of ready to turn the page a little bit, even though it was just a couple of years. So had a lot of interest for a lot of really cool companies and ultimately ended up selling noble to medium. And I thought that was a cool opportunity because medium kind of missed the podcast wave. Like, they could not have been more well positioned to capture a lot of value.

Ryan Duffy:
They had all this access to distribution, all this access to subject matter experts. They could have been a big player in podcasting and they just didn’t, for whatever reason, it wasn’t in focus or whatever, nothing like against them for not doing that. It’s easy to, in retrospect say they should have, but I wasn’t there. So hopefully knowable would help kind of bring them into the audio space in a new way. And that was the goal, and it was going to continue as a standalone product, and we were excited by that. But unfortunately, pretty soon after we went in there, Ev Williams, the Twitter co founder who founded Medium, he left and then a new CEO came in and priorities changed. And knowable is out of focus, which was okay. And then I stepped into a new role set of growth marketing there, and was surprised that for a platform as well known as medium and big in terms of user base, there was a lot of fundamentals and hygiene on the marketing side that wasn’t really there.

Ryan Duffy:
So it was surprising, but also great opportunity to just totally reshape how things were done. And that’s what I got to do. And it was very successful. And it’s the first time you’re building startups, it feels like you’re shouting in the wind sometimes. It’s like, oh yeah, like 50 people listen to this knowable, you know, mini episode today. Awesome. At medium, you’re talking to millions of people like that, and that feedback loop is so much stronger than, you know, anything I had ever, you know, been privy to at any point in my career. So that was definitely gratifying to be able to have a big impact, learn really, really fast and make big changes that help the company.

Ryan Duffy:
Okay. I feel like I just talked for 20 minutes. Cool.

Dana Robinson:
No, that, you know what? I think that’s a super fantastic journey. And the, I’ve got some questions. I’ll walk you back to them. But the, so many people, I think get, get the idea that if you just get the funding, then you win. And so that, you know, sort of debunking the myth that so many new entrepreneurs have, that if they just could get that series A or seed round or pick your phase of funding, that they’re set, you know, because the often when you get that round, you, as, you know, stakeholders can, can even evaluate what your, what the value is of your, of your equity based on that, you know, fundraising round. So people get really excited about the idea. And I love a story that shows you how much, how much work it is, you know, how much risk there is, how often it doesn’t go, how you planned, and sort of the movements throughout. But let me ask you, when you go back and sort of think about your origins and how that shaped who you are now, I think of your time at the agency.

Dana Robinson:
Do you think that if you hadn’t done that, you wouldn’t have been ready for the vidme experience? I mean, in what ways do you think you leveraged the things you’d learn the lessons from your agency years? Because clearly it’s kind of a career change, right? You’re going from a guy that could have continued to be in cat fights, poaching talent from one agent to another, playing Hollywood games, and he made this pretty big move. But I see tendrils, I see threads that tie these things together. I mean, maybe you can draw those strings better than me.

Ryan Duffy:
Yeah, it was definitely a big change, but that was a deliberate one. So I knew that this skill set and network that I acquired inside of these agencies would be valuable at the right startup. So it’s just about finding the startup that saw the value in that. And luckily I did. So could I have ever even made it to vidme without that experience? Probably not. But more broadly, a main thrust of my role across vidme digital objects, knowable even a little bit at medium. It’s all about creator acquisition. We were starting new platforms, marketplaces that were fueled by creators posting original content.

Ryan Duffy:
And my job was to partner with these creators and get them to use our brand new platform. There’s always a risk to do that. New platforms come and go. There’s opportunity costs with every new one you join, yada yada I thought about these partnerships, not like, oh, I’m getting users. This is user acquisition. I thought about it like every single one of these people were clients, especially in the early days. I treated them with the same level of care and attention as I would when I would write an email to Denzel Washington that my boss was copied on. And if there was one error, it would be a bad day for me.

Ryan Duffy:
So every email I wrote to these people was just as exacting, every communication was just as meaningful and honestly, like high pressure for me. That’s just like how I am. And thankfully, mister anxiety, I guess. But it definitely paid off. And I think it makes a difference when you’re trying to sell something new and unproven, when you’re genuinely putting the attention toward these people, making them feel special and unique, which they are, but making them feel that way and just generally being a good steward of the relationship.

Dana Robinson:
Thank you. In fact, it’s funny. It brings to mind a business that I’ve backed. I’ve mentioned my partner who’s been on the podcast, Corey Vernere. We’ve been in the audiobook space for a long time, so we know audiobook publishing, but we have a platform called Zoundy.com right now, and it’s in its incubation where we’re just trying to get the very same people, basically anyone who has an audiobook, to use the platform as a promotional tool to give away or sell the audiobook so they can build funnels. And as I think about it, I think, let me just ask a practical question. How much of what you had to do with curating those relationships because we’re trying to do the same? How much do you need someone like Ryan Duffy? Or how much can you hire someone else under Ryan Duffy? Is it a scalable business or did you really have to do this one at a time on your own?

Ryan Duffy:
It always started with me by myself. Vid me was the biggest we got as a team. I think we were somewhere in the mid twenties at our peak, and I had a team under me. They were young and sort of taking a bet on this startup, and it’s trainable. I don’t know if that deep rooted philosophy that I just have by virtue of circumstance is trainable, but you can teach people to be as careful and to take as much time to get things right. And I actually took pride in helping instill that. And younger people who worked for me and, you know, hopefully they’ve carried that forward even if they didn’t like it at the time or felt like they were being micromanaged, which they definitely were. It makes you better.

Ryan Duffy:
And at least one of them, only one of them has told me years later they really valued that and appreciated it. They all did. But only one.

Dana Robinson:
I love it. Yes, mentorship is not highly rewarding, and it is about like one out of ten of your mentees come back and thank you for it. But we know, we know. I know from being a mentee that I probably don’t go back and thank my mentors enough for what they’ve contributed. So I’m just going to state the obvious for anyone who’s not paying attention, big deal. That you leaned into a skill set that you had when you made this leap to vidme, right. You took the things you knew, the tools you had that gave you a stepping stone, and a lot of entrepreneurs. And as a lawyer, even, I’ve had so many entrepreneurs over the last 25 years that want to start something based on some passion, some whim, some wild idea, something.

Dana Robinson:
They woke up and said, I’m going to solve a problem. And they really don’t have a foundation for that. They’re not leaning into a skill. They’ve acquired a knowledge base. They have a network that they have the sort of relationship capital. The instincts that you brought to that business probably gave you some confidence that you could do some things that you didn’t yet know.

Ryan Duffy:
Yeah, I think I saw it as the path of least resistance. What’s the most valuable asset that I can bring to a company? Coming out of working in Hollywood for whatever it was, six, seven, eight years, and that was the network and the understanding of the landscape, the negotiation, and the relationship management. So a lot of people, they say, follow your dreams. Do whatever you want. I don’t love that advice. You work so you can follow your dreams. You don’t, like, follow your dreams as you work there. But I’ve actually been pretty lucky to work on projects that I really cared about and would probably use or at least be interested by as a consumer medium is definitely one of them.

Ryan Duffy:
I used it for a long time before I worked there. It’s really important to know what you have to bring to the table and leverage that it’s all about leverage. And especially when you’re raising money, you know, if you’re a lawyer starting a startup and, you know, you’re doing, I don’t know, like home food delivery or something, and you’re trying to raise money there, people might be like, well, why are you the guy to do this? But if you’re doing something more aligned with your experience that just, you know, kind of makes more sense on its face. It’s just all about the path of least resistance.

Dana Robinson:
I love that. You mind talking a little bit about the wind down and the. I want to ask you to look at that time in your life, did this feel like a failure at the wind down between you and the team? Was there a lot of commiseration, or is it sort of like, hey, we’ve accepted the fate of this, and we all need to pivot to what’s next for us, and, you know, talk about that crisis?

Ryan Duffy:
Well, we went through it a couple times, like, you know, vidmi ending was really disappointing because there was a minute where it was like, damn, like, we really have it. This is a rocket ship. And it was in certain ways, so when that bubble popped, it was hard, but. And, you know, we had to let people go and, you know, just all the hard things that come along with failure and, I don’t know, we just. We never really wallowed in it. It was always just like, okay, what’s next? Kind of, there was never a long term plan, really. I mean, yes and no. At that point, there wasn’t.

Ryan Duffy:
It was like, okay, we need to wind down this company, responsibly sell it, and then, you know, use the capital that we’ve raised from investors and diligently put it towards something that has a chance of success and returning their investment. So it was always just kind of about like one step at a time. Then digital objects happened, and that was not that disappointing because I was always kind of like, what is this? This is crazy. So it wasn’t like the shocker of the century. When it came time to pivot again, it kind of was shocking. Once nfts really blew up, I’ll say. I was like, big wrong on that one. And then when noble happened, yeah, that one was just so much work, and we were all learning entirely new skill sets, building the plane while learning to fly type of thing.

Ryan Duffy:
And, you know, it wasn’t the, you know, we got acquired by medium awesome. It wasn’t like the huge windfall of the century, like, you know, people might assume when they hear the word acquired. So, yeah, we were kind of ready to move on at that point, so. And it was exciting to go into a new company that we admired and, like, actually used as a product and to build something that, like, we cared about and had experience using as consumers. So that was kind of exciting. But then, you know, when you’re ahead basically operating independently for six or seven years, whatever it was, building startups accountable to each other, yourself, your investors, and your board, aka no real boss situation, then it’s tough to go into a bigger company and you have bosses. And medium wasn’t huge. It was like 100 something people when we got there.

Ryan Duffy:
But that’s just enough where it’s like the bureaucracy is showing its face and the politics are showing their face. And it’s actually, it’s like, I actually think it’s a bad size for a company in a way because it’s big enough that you get that stuff, but then it’s small enough that, you know, organizationally, everything isn’t totally dialed in. So, like, career ladders for young people are not established, and there’s ambiguity, which is never good for morale. Certain processes are not codified, and that creates a little bit of extra back and forth that can be annoying, stuff like that. It’s an awkward teenager size of a company, I guess. Then it’s also about finding your place, because we went there with the goal of building audio for medium and keeping knowable up and running. And then that changed pretty fast when the new CEO came in. So I was like, okay, what’s my place here at this company? And that was hard.

Ryan Duffy:
Some of us, four of us two, kind of fell right into their place and took me a little bit longer and took one of the other guys a little bit longer. We eventually found our places, but there were moments when it was a little bit like, oh, I’m on an island. Does anyone even know? I work here? Because, like, I’m not on a team, really, and I’m just sort of, like, doing my own thing over here, which can be nice if you want to, like, hide and collect paycheck, but that’s never been me. I wanted to contribute, so, you know, those were all transition pains, growing pains, but we got over them.

Dana Robinson:
Now, are you, like most entrepreneurs I’ve met, you’re. You’re permanently broken from the ability to work long term for big company. It sounds like, at the medium confirmed that your later career trajectory is not going to be working your way up in a. Or running a big company.

Ryan Duffy:
I never say never. So, you know, I’m just. I’m out here in the world and letting things happen to me. I never had much of a plan in my career. You know, the one strategic decision I made was kind of moving from Hollywood to tech in a very specific way. Beyond that, it’s all just been like, here’s what comes next. I’m going to take it as it comes. So, you know, we’ll see.

Ryan Duffy:
There’s a lot of great things about working in a big company. You know, you have a specialized role. You know what the scope of your job is. You’re actually not supposed to, in most cases, go outside of that scope. So it’s generally, like, easier and more relaxed in certain ways in terms of workload. But at the same time, it’s messed up for me, but I get anxiety when I don’t have something to do and I’m not working. My partner does not love that. My parents don’t love that.

Ryan Duffy:
But it’s just kind of how I’m built. My dad understands it because he’s the same way, you know, working in a quote unquote nine to five, I don’t know what I would do with, with myself, because even at medium, like, okay, biggish company. But it still felt like startup mode in a lot of weird ways. It was not easy in the way that, like, you imagine, oh, my company got aqua hired by Facebook, and I’m gonna kick my feedback for a few years, invest my stock, and not do a whole lot. It wasn’t like that. We were working hard.

Dana Robinson:
Interesting. That’s great. Along this journey, like, if you look back, I tend to look back, and my initial reaction to past decisions is because I’ve been through a bunch of the same kind of things that you have with things that went sideways, things that went flat, things that were a base hit, things that you thought were going to take off that didn’t. But that wasn’t horrible because you at least got through a transaction or, or something. But I do have a first instinct of saying, well, I should have this, you know, I should have held that. Just a simple, simple example. I should have held that piece of real estate I sold for $2 million because now it’s worth eight. But then my wife’s very wise about this, and she’s like, well, you know, the thing you were going to buy with the gains was, you know, it was like a strip mall that would have gone down in value by half.

Dana Robinson:
So, you know, you can’t go back and second guess because the things that you did got you to where you are right now, what you’re doing right now. I’ll invite any observations on that from you and ask you as you head into the thing that’s next for you. What’s your hindsight 2020 on Ryan Duffy?

Ryan Duffy:
Well, I think the biggest missed opportunity was the NFT platform, which I’m embarrassed to say that because I’m so not an NFT guy, but we were super early to this market that got absolutely massive. We were super well positioned. Definitely would have been ripe for a big acquisition when stuff was really peaking and, you know, we missed the boat. So it’s nice in one way that we, like, had the right idea, but we, we folded too early. So that was tough. But it’s not like you don’t think about that. It’s like, it is what it is. I don’t think a whole lot about, oh, it could have been.

Ryan Duffy:
I wish I had a cooler, more philosophical answer to that question, but I just, like I said, I just kind of one step at a time, just taking it as it comes and, you know, not worrying that much about what happened before. You know, there haven’t been any huge disasters, luckily. So if there were some of those, I probably would want those back. But everything has been mostly good.

Dana Robinson:
I love it. And you know what? The entrepreneur journey that you’re on is probably the more common journey than people who strike out and have big failure as well as the people who hit a home run on their first shot. The sort of like, Epic started this business and it took off and I sold it for $100 million is super rare. So I love hearing your journey as sort of the meandering through opportunities that leverage the assets that you have garnered along the way. And we don’t need to talk in detail about it, but your current startup is in a phase where you are. I know it to be leaning into more of what you know well and, you know, and in a couple of years might have the story that you wouldn’t have been able to do the thing you’re doing now had it not been for this journey over the course of the last, you know, 1015 years to get to where you are right now.

Ryan Duffy:
Definitely. It’s, you know, the platform we’re building is called Stack. It’s sits squarely in the creator economy just as pretty much every startup I’ve worked on has specifically the expert economy. So a lot of overlap with knowable and medium. And, you know, I’m excited by it. It’s sort of a big idea, a new model, new business model, and monetization model being introduced to this world of online business and mentorship. So, yeah, it’s, you know, we’ll see what happens. It’s insanely early, so I wish I could talk about it more, but, you know, that’s about the, like, highest level picture I can paint.

Ryan Duffy:
I’m excited. You know, I’ll say this that coming out of medium and having been there for a couple of years, it’s so, so nice to be back at this super early stage just figuring shit out. Like, literally from negative one, it’s not zero to one, it’s negative one to zero and then zero to one. And I really feel like that’s where I thrive. That’s where I’m happiest. Maybe that’s psychotic, but I think it’s fun and everything’s on the table at this phase, and it’s all about just figuring shit out. And I think that’s one of my superpowers, is figuring shit out. I like to do it.

Ryan Duffy:
So I’m happy to be back in this sort of crazy early startup grind mode. And you never know what’s going to happen, but, you know, if it works, it has a lot of potential and, you know, if not, then we’ll figure out something else cool to do next.

Dana Robinson:
I love it. Yeah, that’s great. Sort of. What’s the equanimity about what you’re doing, Ryan? I’ll just make that observation as we wrap up. The ability to take what you have leaned into over the past has given you some really good habits of mind that give you. You’re not a guy in anxiety the way a lot of startup members are. You’re a guy that sees this for what it is and is going to be able to walk through with some equanimity and discipline and enjoy the ride.

Ryan Duffy:
Yeah, that was mostly true. I have a lot of anxiety, but it’s predictive of anxiety.

Dana Robinson:
Well, I can’t. I can’t sense it in your voice or see it in your face, but thanks for the admission. I’m sure everybody else out there appreciates that as well. I, too, sometimes have anxiety, but appreciate the honesty. Partying shots, anything that, you know, obviously you’re. As everyone seems to be who’s in business of any kind. You’re on LinkedIn. Ryan Duffy.

Dana Robinson:
D u f f y. Yeah. Other parting shots that you want to fire off before we wrap up?

Ryan Duffy:
Yeah, no, not that big on social media, so nothing to plug. Don’t have an album. But once again, thank you for having me. It’s fun. I don’t love talking about myself, but it’s nice to once in a while and get an opportunity to reflect and think about some things that have happened, good and bad. So hopefully it helps somebody.

Dana Robinson:
I agree. I agree. I think I needed stories like this 20 and 30 years ago, and I share them for that reason. I think people need to hear our stories. Not because we should be famous for being the geniuses in the room, but because there’s a bunch of Ryan’s adanas that are 20 something and 30 something that are trying to figure their shit out. So, everybody, thanks for joining me and Ryan Duffy on the exit plan podcast. And as always, reach out to me. Hello@danarobinson.com. Thanks for coming on.

Dana Robinson:
Ryan.

Ryan Duffy:
Thanks, man.

Dana Robinson:
Thanks for joining me on this episode of the Exit Plan podcast. I’d love to hear from you. Feel free to hit me up with questions or comments by emailing me at hello@danarobinson.com or leave comments and questions by calling 858-252-7785 call 858-252-7785 and leave a message.