S6 Ep. 2 — Inside Refinery: Mike Kadin, CEO of RedCircle

Media Thumbnail
  • 0.5
  • 1
  • 1.25
  • 1.5
  • 1.75
  • 2
This is a podcast episode titled, S6 Ep. 2 — Inside Refinery: Mike Kadin, CEO of RedCircle. The summary for this episode is: <p>On today's episode of Fast Frontiers, host Tim Schigel sits down to speak with Mike Kadin, the CEO of RedCircle. The two discuss strategies for managing high-growth companies, lessons learned in hiring and how Mike met his co-founder Jeremy Lermitte.</p><p><br></p><p>Key Takeaways: </p><ul><li>[01:55] Meet Mike Kadin of RedCircle</li><li>[05:56] Experiences unique to RedCircle's growth and lessons in high-growth</li><li>[09:55] How far out was RedCircle planning their growth strategy</li><li>[11:10] Hiring takeaways and lessons</li><li>[16:38] When and how Mike and Jeremy met</li><li>[18:56] Mike and Jeremy finding common ground and learning from past workplaces</li><li>[23:01] Be Real and Be Respectful</li><li>[25:31] Continuously learning and different stages of growth</li><li>[29:02] What's attracted Mike to podcasting</li><li>[32:25] The integration of technology in cars and the listening experience</li><li>[33:15] How Mike is helping podcasters, and how the medium has changed</li><li>[37:02] What Mike wants podcasters to know about RedCircle</li><li>[38:28] What the future of podcasts looks like according to Mike</li></ul><p><br></p><p><br></p>
Meet Mike Kadin of RedCircle
03:59 MIN
Experiences unique to RedCircle's growth and lessons in high-growth
03:57 MIN
How far out was RedCircle planning their growth strategy
01:14 MIN
Hiring takeaways and lessons
05:26 MIN
When and how Mike and Jeremy met
02:16 MIN
Mike and Jeremy finding common ground and learning from past workplaces
04:04 MIN
Be Real and Be Respectful
02:16 MIN
Continuously learning and different stages of growth
03:29 MIN
What's attracted Mike to podcasting
03:22 MIN
The integration of technology in cars and the listening experience
00:49 MIN
How Mike is helping podcasters, and how the medium has changed
03:44 MIN
What Mike wants podcasters to know about RedCircle
01:23 MIN
What the future of podcasts looks like according to Mike
02:38 MIN

Tim Schigel: Welcome to Fast Frontiers. I am your host Tim Schigel, Managing Partner of Refinery Ventures. In this episode, we're talking with Mike Kadin, Co- Founder and CEO of RedCircle, a hosting platform for podcasts and a Refinery Ventures Fund II Portfolio company. Mike has very interesting career, super smart guy. Went to Brown University, degree in electrical engineering, got his teacher certification, is also a musician. So he spent some time teaching, got into development, joined Uber, was part of the earliest development teams at Uber starting in 2013, where he met his co- founder Jeremy Lermitte. They went on to start RedCircle. My biggest theme or so what, in this conversation that I'd love you to hear about is his experience at Uber and what it meant to build fast and hire people at that kind of pace. Please enjoy my conversation with Mike Kadin. All right. Welcome Mike to Fast Frontiers. So happy to have you on.

Mike Kadin: Yeah, thanks for having me.

Tim Schigel: Great to have you as part of the Refinery team. It's so funny, I tell people the story of how we connected. You and your wife recently moved to Cincinnati and I get a call from our co- investors, from Nick at Epic VC, saying," Hey, do you know about this company RedCircle in Cincinnati?" And I was like," Wait a minute." Yeah. My job was to know everything about Cincinnati at a minimum, right?

Mike Kadin: Yeah, well I think I had been in Cincinnati for four weeks at the time, so you get a pass.

Tim Schigel: I get a pass? All right. Yeah, for six weeks inaudible

Mike Kadin: For not knowing I was there yet. Yeah.

Tim Schigel: Yeah. Very cool. So really look forward to sharing your background and your co- founder Jeremy's background and some of the journey that led you to creating RedCircle. So I was thinking maybe we start there and give folks some of that background, how that's informed you as a founder and as a CEO, and then maybe talk about the podcasting market and space specifically as a next frontier of media.

Mike Kadin: Yeah, sounds great.

Tim Schigel: Yeah, so first off, a little bit about your background leading up to at Uber, when you and Jeremy met.

Mike Kadin: I started, well even before Uber, I had worked at some nonprofits and I was a high school teacher, so Uber was the first real for profit business that I had the luck of joining. And I started at Uber in 2013 when there was some maybe 250 people or so, maybe a little bit less. And the engineering group was 40 or 50 and we all fit in one room in San Francisco, which I remember really well. And yeah, I started there right about at the hyper growth phase for Uber. There was a ton of venture capital behind the business at the time and we grew the size of the employee base from 250 or so, and I started in 2013 to, gosh, I don't know, tens of thousands, by the time I left five years later. And I sort of got, as a result, the ultimate crash course in growing teams and scaling technology and scaling up products. Just got super lucky to have found a spot there. The reason I got the job actually is because I sang acapella with someone who was in the HR department. Don't know if I would've even gotten the gig otherwise.

Tim Schigel: Oh, that's the reason. Okay. You've been holding out. I didn't know that. That makes sense, that makes sense.

Mike Kadin: I don't always fly my acapella flag that high, but I figured here on a podcast is the best place to do it. But yeah, I got the job there. The other funny story about getting the job there is, during my interview, I got asked a question that I was familiar with from another podcast, which is a radio show called Car Talk. I don't know if you've seen Car Talk or listen to Car Talk, but they talk about automobile repair. And every week they have a puzzler, which is a brain teaser. And they asked me a question in the interview that I knew from a Car Talk puzzler and I just pretended that I didn't know the answer and I sort of worked it out on the whiteboard over 30 minutes, and finally. So my hire was under somewhat false pretenses as well. Anyway, I was there as a frontline software engineer in a job I probably didn't deserve, if it wasn't for that puzzler. And really within six months, they looked me in the eyes and they said," You're a fine engineer but you should be a manager." And pushed me into doing that whether I wanted it or not. It was more that I was in a place where the organization was scaling so rapidly that they just needed people to take on responsibility. And I worked on Uber for Business, which is their business product. In the beginning I was part of the core team that founded that product and then got handed this scope of Uber's communications platform. So worked on all of Uber's technology for email and SMS and push notifications. The phone calls between you and the driver, where they can't see your number and you can't see theirs. Also worked on various other sort of marketing stuff like uber. com and also worked on internationalization and localization across the company and all the engineering infrastructure there. So I've really diverse set of different projects that, in the beginning, my team was three people with that scope and by the time we left, depending on when you looked at us, of maybe 40 or 50 person organization of product people and designers and engineers. In just short four years, went from one of the code monkeys on the line to working on a pretty large organization. Not necessarily because I'm so great, but because I was just in the right place when Uber was going through that stuff. I had to be able to swim as the water rose and did my best to do so.

Tim Schigel: What are some of the takeaways, as you know and I think our listeners know, a big focus of ours at Refinery is growth and specifically that there are experiences or patterns that are specific to high growth company that may not exist in a company that's not experiencing high growth. What are some of those experiences that you took away from that?

Mike Kadin: Yeah, excellent question. I mean there are some things that Uber got very wrong. You can go read about them in the New York Times from 2017. There are some things that Uber got extremely right. The speed at which the business was growing required the engineering team to keep up. And in the beginning, when you really quickly transition from a startup trying to get things done to a startup trying to prepare this thing to scale from 1, 000 trips to tens of millions of trips, you really have to put in a lot of energy and sweat, really, to keep the thing up. People don't realize the amount of energy that went in just from humans with hands on keyboards to keep that thing alive on a Friday or Saturday night when we hit our peak traffic. And when you are in an environment where every Saturday night is the biggest night you've ever had, there's only a certain team camaraderie that comes alive in a situation like that where everybody is sharing a common goal towards supporting the business and growing this thing and in making sure that people don't end up stranded at 1:30 in the morning at the airport when they're counting on you or that the tens of thousands and eventually millions of drivers who are depending on our engineering team for their livelihoods, could count on us. Meanwhile, we were duct taping together a bunch of startup code that was barely keeping up. And so when you are facing problems like that, there's a certain cultural element where people really come together to take on tremendous challenge and can accomplish a lot more than they might think they'd be able to do when everybody's got that shared vision and that shared goal. Uber did a really good job in the beginning of having folks really, really aligned on the business goals from the start. Really, really aligned on what we were doing from the start. And when I was up at 2: 00 in the morning because something was broken on a Saturday night, it didn't necessarily feel like some massive burden to my work/ life balance, although it definitely was. But it felt like my duty and something that I was doing for the good of the people around us. So there's just something that happens I think when you're in these growth environments, when you hit, what in the case of Uber, I think is some of the most amazing product market fit that exists and the team rallies around that to be a part of that and to achieve, not just the business growth, but also the stepping up to the technical challenge of rebuilding the engines on an airplane while it's flying.

Tim Schigel: So it sounds like what you describe is that there was a tremendous amount of market pull happening. It wasn't like you were having to work hard to make that happen, it was more of trying to keep up with it. Is that accurate?

Mike Kadin: Especially on the engineering side, yeah. For me, we were responsible for sending out the text messages for verifying your phone number when you sign up or the receipt that you would get after or the password reset if you forgot your password. And those things were critical for the fundamental operation of the business, not necessarily it's growth. And so for us it was like," Gosh, we got to figure out how to get a text message delivered in Azerbaijan." Or we've got to figure out how we're going to, if we're in the situation where the email vendor goes down, where we're not down for three hours. So a lot of engineering problems that were associated with supporting the business's growth, because in reality that marketplace flywheel was spinning pretty hard even by the time I got there and there's inaudible

Tim Schigel: Yeah. How often were you, or how far out were you planning? It sounds like it was week to week. Did you ever have the luxury of thinking, what's going to happen a year from now or six months from now?

Mike Kadin: Definitely not. I mean maybe towards the end, we started to have a little bit of formalization of our product planning process, but for the first two or three years, we were really going and using our intuition and using our whatever telemetry we could have, to make the best decisions we could make that were sitting in front of us at the time. No business ever has software engineers falling out of their pockets where that's not the resource constraint, so. Even the biggest and fastest growing ones. But on the other hand, you still have to be really thoughtful about how you're using the couple of people that you have, even while we're hiring and bringing on people all the time. I started that team, it was three people, we had all the scope that I described before. We got up to 40, so a lot of time was spent hiring obviously. Even then, when there was just three of us, we had to be extremely thorough about what we paid the most attention to, because there was no way to fix everything that was broken all the time.

Tim Schigel: What did you learn about hiring in that process?

Mike Kadin: A ton. So Uber did the Amazon thing called bar raisers, where there was somebody from another team on every interview loop that was there. Not necessarily to quote, unquote," raise the bar," even though it was called that, but to sort of be an accountability mechanism between teams, because Uber's hiring mandate was very strong. It would be easy to just hire up lower quality talent and let managers build up big organizations and use that as a way to get promoted instead of actually hiring great people. And so there was of accountability mechanism and I participated in that program. And so in addition to hiring from my own team, I was also doing two or three interviews per week for other teams. And so I don't know the exact number, but I've done 500, maybe more, interviews during my time there. And so I learned a ton about hiring. I got to see the people we hired and who was successful and who wasn't. What things we should be looking for and what we shouldn't. And so I learned a ton and I'll tell you a couple lessons that are really important to me from that time. First of all, I don't buy into the Silicon Valley software engineering ethos of a hazing style interview that has brain teasers and high pressure tactics. There are occasional fire fights and maybe at Uber a little bit more than others, but the fact is, most of the time, in the case of software engineering, and I suppose this is true in other functions too, you're sitting there doing your work with your hands on your keyboard in a relaxed and comfortable environment. And what we want to simulate, as much as we can in an interview process is, what's it going to be like to work with this person in a real environment? How are they going to collaborate? How are they going to be able to perform when they are relaxed and using their full brain instead of just having 50% of their capacity of their CPU overwhelmed with the anxiety of the interview itself. And so I tend to ask interview questions that are not that challenging, but there's always extensions that make it so that the person can never succeed. So I have a set of interview questions where it starts easy and it gets harder and it gets harder and it gets harder and you're never going to get it. I've never gotten the last question. So it's more of a conversation that goes on, but you start with something easy and you build confidence on the other end of the interview table, until the person is able to really show you who they are. And you should make it fun, you make it personable and you're going to learn a lot more about who's on the other side of that. The other thing I'll say is that I think interviews are extremely blunt instrument and really rough as a way to measure people. It's the only tool we have I guess, but it's pretty rough. And so we still believed in, and I still believe in to this day, having people either write code or do code reviews as a software engineer, as a part of the interview without somebody breathing down their neck. Something in their natural state. A short project where you go out and build stuff by yourself. The last thing that I'll say is that I learned really early on that hiring is a business process. There's a transaction happening here, but in the end of the day, I can't treat hiring decisions in a fully cold and business oriented way. It's a human decision, who you bring onto your team and you have to take that really seriously. I hired someone who I had a feeling was not the right fit, but the team was excited about, and I don't want the lesson to be like managers should go against their team, but I sort of had a strong feeling that this was not the right fit, but the team was excited about the candidate. I brought them on, and within a few weeks, it was quite obvious they were not ready to be there. And you've done the calculus in my head. It's like," All right, the team wants to hire this person, I don't. If I'm going to hire them, I need to be okay with letting them go in three months if I'm right." And at the time that calculus was like," All right, that's a business decision that I can be okay with." But that person who was a new college grad, started off their career with a really rough spot, when I had to let them go not that long after. And that's going to have long- term impact on their career, and maybe it was a fine move for the business to take that risk. But in the end of the day, part of hiring is a human decision and you have to think about the people on the other ends of these calls as well. So to this day, there's the whole idea of, comes out of Netflix I think, that we're not a family, we're a team. And I subscribe to that idea, but only to a point. I think in the end of the day, these folks are not your family, if you're a team leader, but they are real humans that you got to treat that way. They're not just resources to be allocated.

Tim Schigel: Absolutely. And you are on a journey together, a life journey together, where hopefully people are transformed in some way or improved through that process and learn.

Mike Kadin: Yeah. And that person who I mentioned, they came out okay, they found another job somewhere. And people that I've let go or not hired along the way, who've been frustrated at that time, I check back in to see, is this person on the street? And they never are, right? Everybody's on a journey of their own and they're going to find the right way to get where they're trying to go.

Tim Schigel: Some great learnings. The bar raisers I actually hadn't heard, so I liked that. That's a very good technique. So tell us about when you and Jeremy met.

Mike Kadin: Yeah, so Jeremy Lermitte, is my co- founder at RedCircle. And Jeremy was on Uber's marketing team. He started as an on the ground marketer in the New York City office and was part of that real early Uber sort of hustle culture. And made his way, eventually, to San Francisco to be a part of the marketing team. And again, my team on the engineering side was responsible for email and SMS and all these different marketing channels. And so his team was consistently asking for stuff from my team and me being an engineer trying to keep the lights on, and an arrogant person, mostly thought they didn't know what they were talking about and wasn't really doing a lot to support what they were asking for. And started actually building a bunch of stuff that wasn't what they needed. And as a result, Jeremy and I really didn't get along. He was trying to get stuff from me. I was saying no, there was a lot of tension there for a long time. And the business really understood that our team had some really good ideas. The marketing team needed more technical support and that something was missing in the organization for us to be able to push marketing forward and use all of Uber's technology skills and what we built to be able to drive our marketing program forward. And some smart people put together a bunch of folks to try to figure this out. And eventually the result of that project was they stuck Jeremy, this guy who I didn't really get along with, on my team as my product manager, which I didn't have. I thought product managers were stupid and I can tell you they're not. And that's how it started. They shoved us on a team together and we didn't really get along. And over the course of a couple years, we really came to respect each other's views and our ability to disagree was really strong. And it was a big part of building out this communications platform team that we ended up building out to a much larger size and built a bunch of really cool products along the way. And so when I left Uber a couple years later and started looking around for new jobs, I decided I didn't want to do any of those. I wanted to start RedCircle instead. And Jeremy and I had lunch and by the time we were done doing that, we were doing it together. And I'm glad, because at the time, was kind of lonely trying to decide if I was going to do this crazy thing, and at least there was one other person that was willing to be as crazy as me.

Tim Schigel: So were there some shared lessons between you and Jeremy that you said," Hey, these are things we want to make sure we do that we learn from our Uber experience and these are some of the things that we don't want to do." Or mistakes that you don't want to repeat?

Mike Kadin: What we built at RedCircle is a podcast platform for podcasters that distribute their content and stuff, and then also for advertisers to be able to buy ad space on those podcasts. And so the advertising side of what we do is not all that different from a lot of the marketing tools that we built for marketers. And one of the cool things that we learned at Uber is that, when we originally built a bunch of tools for marketers, we didn't spend a lot of time investing in the user experience of those tools, because we're like," All right, there's maybe 1, 000 marketers at Uber, spread around the globe. This is not a core customer that we need to spend a lot of time making sure their job is easy or that the web app looks pretty or things like that." We just figured that we should prioritize instead, its functionality versus its usability, because the customers were internal. And that was a bad idea. The customers didn't like it. They decided those weren't the right options for them. There were other third party services that they were using before and we were trying to force them to start using our stuff and it wasn't going well because it wasn't a pleasure to use. And so what was the really fundamental thing for me to learn, as a software engineer, I'm used to, I'll just type into a command line interface. I don't need anything that looks good or is really that easy to use, to find value in it. I think typical customers and especially marketers who are technical but also have a more artistic and creative side to their work, they need to have products that don't just do good, but feel good and you need to be able to show them the value, not just through its functionality but through its usability. And so for us on the advertising side of our business, you can look around in the marketing, in the MarTech world or the ad tech world, and there's a lot of really bad UIs, that sure, there's very powerful functionality on the other side of that. But instead what we decided to do is really focus in on making the advertising side of our platform just as usable and amazing as the consumer side of our platform, which is oriented towards podcasters. And it's been great. Advertisers when we demo the thing are like," Wow, this is awesome. I really understand it and I can..." So it's got a lot of value just upfront and then it's got a lot of value when advertisers put their hands on it as well. Some things that we won't do. So at Uber there were a bunch of cultural challenges. The company scaled extremely fast, and as a result, I think what we did, was we hired a bunch of people, who came and represented a kind of cultural index fund for Silicon Valley. That's the way I like to think about it. People came from Google or Amazon or Facebook and they showed up there and they brought the pieces of their culture that they wanted to bring. And when you end up with just a big hodgepodge of different cultural stuff, you're going to end up in a place where there is no well- formed culture or where the culture takes a turn that you're not intentionally building. And in the case of Uber, you can read about some of the negative stuff, that there's also something really important that needs to be done early in a company to set the right moral foundation for the work that's happening as well. So one of the things we did way earlier than I think other startups do, is define a set of cultural values for the company that we have built together and have on paper and everybody knows, and when we do performance reviews, they're built into it. Which Uber didn't have, you can believe it until 2016, when the company had thousands and thousands of people and was doing probably billions in revenue or in GMV. So really learned a strong lesson that if you want to build a culture that's powerful and an asset for your business, you have to spend a lot of time being really intentional about what you do to build that versus just letting the people who show up bring whatever they want and take the culture from you. So we've been really thoughtful about that.

Tim Schigel: Do you have any examples of any of those values that you established that were put to the test so far, early on in the first few years?

Mike Kadin: Yeah, I mean the first two values that we have, are in conflict on purpose. The first one is called Be Real. And this goes to that sort of not a family, not a team, but somewhere in between idea, where we want people to have a work personality that's, if not exactly the same, very similar to their home or friend personality. We want people to be real at work. Not necessarily tell us everything about what's happening in your life. It's fine if you want to do that, but that you don't have some separate way you talk at work or behave at work that isn't the real you and we feel like that's important. It's this bring your whole self to work idea. On the other hand, what comes with that is that people need to be honest and be direct sometimes. And Uber was famous for very confrontational culture. One of their values when they eventually established them was called toe stepping or principled confrontation. These were some of the values. That's a little strong. I think Be real is a little bit better. It's like," Okay, bring yourself to work and if you have something that you believe or something that you disagree with someone about, let's not beat around the bush and do politics. Let's be direct and be real with people." On the other hand, the second value that we established right after that is called Be Respectful. And that doesn't mean you have to be everybody's best friend, but if people don't have enough psychological safety and expectations of respect from their peers, then it becomes really hard to be real with each other. And so these things we establish early and it's hard. We ask people to give direct feedback to their peers. We ask people to receive really hard feedback. We ask people, who are used to from working at other places, putting a corporate veneer over themselves where they're talking about circle back and all these kind of jargon and nonsense, whereas I'm cursing every three words and being myself. I think sometimes it takes a lot for people to adjust to that and some people they never do. And if that's not the right fit for the culture, then there's some other place that might be a better fit for them as well.

Tim Schigel: That's a great example. The size of the team so far is... Trying to remember now how many we have.

Mike Kadin: Just under 30.

Tim Schigel: Have you seen that some folks work at certain stages of the company? They're a good fit for when you're under 10 people, when you're 30, when you're 300?

Mike Kadin: I don't know about 300 yet, but we're on our way. What I would say is, there are people who are zero to one people for sure. And there are people who are more process oriented and more willing to get into weeds that the original builders don't care about and don't want to care about. And I think that's supernatural. And I can tell for myself, I've had to really change what I value in the work over time as well. It was a lot more fun when I was spending 70% of my time with my hands on my keyboard writing code, building this thing from the beginning. Nowadays when I sit down with a financial model or I'm designing a performance review questionnaire, these things are extremely valuable, but far less easy to get any immediate feedback and any kind of quick wins and help you feel good about the work you're doing every day. And so if you take that and generalize it to employees, some folks, especially more senior folks, are used to that. That long feedback cycle and the ability to build something over six months or 12 months and feel good about it. Whereas I think some of the early builders at the company, were way more excited to ship a feature today and watch that graph go up today and do that every day until the graph is 100X where it was before.

Tim Schigel: Well it seems like the important part of that story is that you are growing as well. You're not expecting others to grow with the business. You're having to stretch yourself and do some maybe the work that you wouldn't normally want to do or consider yourself good at, but you've had to do it and will continue to have to do it if you want to keep growing.

Mike Kadin: I mean, 100%. The skills required for this job are so different after four years than they were when I started. And I'm sure they'll be super different in four years from now again. The control planes that you're controlling and the telemetry that you're looking at is all extremely different. In the beginning when you're just trying to get a couple percent of the right graphs each week, it's a lot easier to steer a speed boat. But now that we're kind of like, I don't know, maybe a luxury yacht, we're not a super yacht or an ocean liner yet, but we're big enough where you don't turn on a dime. You really have to change your approach and change your way of thinking. And it was really interesting you just said that. I work with a CEO coach, which I really encourage people to do and he really helped me realize at one point that I had been doing so much stuff that I don't like doing, whether it's the financial operations or spending a ton of time on stuff that's non technical. I've become an advertising sales leader, which I never thought I would be. And some of it I ended up really enjoying. Some of it, not so much. But as a CEO of the company that's fast growing and that you have to steer slowly, even while it's moving fast, you have to step up and take on things that you might not like, but you've got to be able to grow and adapt and take those on either way.

Tim Schigel: Well, you're doing a great job. So let's talk about the industry you're in and the podcast industry as a fast frontier, as a new frontier in media. What attracted you to it and what are some of the dynamics that you're witnessing today?

Mike Kadin: Yeah, I mean what attracted me to it is that I'm just an auditory learner. I remember being 11 years old and getting my hands on a bunch of books on tape that my parents had in the bookshelf and understanding what those were and putting a Sony Walkman under my pillow and I was going to sleep and playing some James Michener novel. From the very early ages, I knew I enjoyed being talked to, to learn. And so I've been a podcast listener for forever. And when I quit at Uber, I was really thinking about what I was going to work on next. And I don't necessarily think Uber is a fundamental bad for the world, but I'm also not convinced it's a fundamental good. And I really wanted to be sure that I could be proud of saying the next thing that I built was going to be something that really, I could be proud to say I was working on. And so I went and started looking around and I got some job offers at some standard places. I got some not job offers at some places I would've liked. And I really got inspired by some companies in what, today, you would call the creator space. Then that wasn't even a term then really. And I really got inspired and that's kind of what put things together. I've been a podcast listener for forever. I've been inspired by these creator oriented companies. I started building a podcast platform that was really a way for me to write some code before I went and did a bunch of interviews, because I hadn't done a lot of that as a manager in a while. And eventually it just went from the back burner to the front and I became increasingly obsessed and I found myself up at 2: 00 in the morning reading a trade journals podcasting and trying to understand customers and what they needed. And that's sort of how the company was born, why I chose it. I'm not a podcaster myself. I am a musician and a creator in other forms, but I'm a podcast listener and just a podcast obsessed person. So that's kind of how I chose it. I wasn't super intentionally choosing the market out of some recognition that this was some great place to build a business. I wasn't that smart yet. I was just really interested in podcasting and had just had this crazy run at Uber. I wanted to get back to building. It turns out though, that I chose something pretty awesome. Back then, the total advertising spend in the podcasting space was something like 300 million, and last year is 1. 4 billion. It's only been four years. The speed and growth of this market is incredible. And during the course of that time, listenership has continued to increase to the point where now 41% of American adults are listening to a podcast every month. And we still have a ways to go. The radio is somewhere between 80 and 90 still, so there's definitely a lot more engagement for Americans to have with this medium. But in 2013, 2014 it was so 13%, 14%. Was the thing for nerds, and now it's 100% sort of mainstream medium. And so again, I didn't choose the market because of the momentum, but luckily chose wisely.

Tim Schigel: Well with the integration of technology in cars, I would expect that podcast listening in cars, well I know, that's going up as well. So that potentially starts moving radio out of the way because it's asynchronous nature. Choose whatever you want. I know every road trip, we binge on podcasts.

Mike Kadin: Yeah. I can't tell you the last time I listened to the regular radio, and I think that's probably true of a lot of millennial folks like me. But whether it's the car or the AirPods in your ears while you're doing the dishes or taking the trash out or when you're at the gym or wherever, people are finding more places within their life to interact with on- demand audio. And I love music, like I said, I'm a musician, but sometimes I want to listen to music and sometimes I want to learn something or be informed. And that's where podcasting is just continuing to grow.

Tim Schigel: Let's talk about how you are helping the podcasters and maybe some stories of how their business as podcasters has changed.

Mike Kadin: Yeah, absolutely. I mean, the realization I had when I started to investigate the market, was that most of the ad deals that get done in podcasting, to this day, despite the fact that podcasting is a technological form of distribution, they're really just done with emails and spreadsheets and checks in the mail. I got a check in the mail yesterday that I had to deposit for an ad that we ran. And I mean, it's just insane. It's 2022. Podcasting is a digital medium from the start. The fact that these deals are all coordinated in the style of radio, just creates so much friction and complexity to getting an advertising deal done, that as a result, most of the deals are done on the largest podcast to make the management of those campaigns feasible for those that have to do it. You'd much rather buy, if you're the marketer working on this, you'd much rather buy on one large podcast than on 50 small ones, because you're going to be the one coordinating all those deals. And so as a result, most of the money in podcasting is going to the top 500 or top 1, 000 podcasts, but there are four million out there, there's half a million monthly active. So there's just tons of people out there creating content, many of which would like to grow and monetize, but just don't have access to that. So our business is about helping make sure that it's not just Joe Rogan or the New York Times or whoever that's up at the top there, who's making money from this expansion in consumer habits. And so what we do is we help podcasters to get matched up with advertising deals. And rather than using emails and spreadsheets, we have a fully automated and very complex workflow software, that makes everything really simple for the podcaster, where they get a deal, they click yes, they record an ad, and they're done. Or, extremely powerful on the advertiser side, where they can pick and choose the right podcast that they want to deploy on. They can measure and understand their spend, and they can deploy a podcast advertising campaign to 100 plus podcast in five minutes just by clicking on which ones they want. So that's what we built and it's really a Robin Hood play. It's a make sure that the money goes to the people and not just to the people at the top. And so far so good. The other insight that we didn't know when we started the business, but that we've learned as we've gathered more data, is that more than half the listening is happening down in what we call the fat torso of the market. It's not the head, it's not the long tail, it's the big middle, like the one I have. And it's where most of the listening is happening and where a lot of podcasts, we believe, are underserved. And last thing I'll say is what you said before, there's podcasters that use our platform that depend on this as their livelihood. Maybe it's part of a collection of internet creator stuff that they do to get paid. Maybe we pay them out 10 or$20, 000 a year and it's part of their collection of different revenue sources that they have by being an internet creator. But we are really proud to be doing the work to make that possible for them so that their art can be something that they live off. If you have 10,000, 20,000 people listening to your podcast. 20, 000 people, that's how many people fit in the Oracle Arena where the Warriors play. We have folks on the platform who have 20, 000 people listening to their podcast every week, who barely made any money off it before they came to us. And so just thinking about the disparity between those two things, how much commerce is happening inside Oracle Arena versus somebody showing up every week to literally have you whisper into their ear. That's got to be something that has value and we're really happy to help those podcasters unlock it.

Tim Schigel: That's great. So if anybody here listening is a podcaster, what do you want them to know? What should they be thinking about and how should they think about RedCircle?

Mike Kadin: Yeah, look, there's a million places that can use to distribute your podcast to Apple and Spotify and everywhere else, and they all have affordances and they all have constraints. Frankly speaking, that market is somewhat commoditized. There's a million places where you can do it and it's not a very complicated technical problem. I was done with that in six weeks once we started the business, before we even started the business. So you can choose any one of those you want. Everyone has its own affordances, and here's what ours are. So we focus on growth and monetization. If you're a VC and you're listening to this-

Tim Schigel: That sounds complicated, Mike.

Mike Kadin: Well, yeah, if you're a VC and you're primarily interested in just distributing your podcast and you don't want advertising, then we're probably not the platform for you. If you are a creator who's looking to make real money on the work and not pull your hair out while doing it, let me pull my hair out instead. I've probably lost half of my hair on my head over the course of building this business, but we take care of that in a fully automated fashion for you. So that's the reason you'd want to choose us. If you're interested in growing your audience for which we have some amazing cross promotion tools or if you're interested in monetizing through advertising or through listener payments, our software can really help you pull that off. Whether you have 500 people listening or a million. We have some podcasts that are up at that size as well.

Tim Schigel: Terrific. And what's your view of the future of podcast? What do we have to look forward to over the next five years?

Mike Kadin: Yeah, I mean, the podcast market is very fragmented on the listener side. You can listen on Apple, you can listen on Spotify, you can listen on a cornucopia of smaller and more interesting apps. And even Amazon entering the space, Google entering the space, there's talk of YouTube getting more active and sort of trying to treat podcasting as a first class thing. And so we as an independent company, that relies on the open nature of podcasting's distribution, which I'll skip the technical details of, but podcasting is amazing in that anybody can create one and anybody can get it into these listening apps very easily. We are excited about a future where there is more and more innovation and competition in the listening app between different businesses. Apple has had a sort of monopoly on that for a long time. Spotify has come and challenged it, but it's still the underdog. But there are other larger tech companies and tons of independent apps that are coming and making that experience more dynamic and there's more competition, which we think is great for consumers. So I anticipate more things will come there, whether it's more video, more transcripts, more social interactivity, more ability to share. Those things I think are going to be amazing for listeners and really help to improve the experience of listening to podcasts. And what that does is great for the ecosystem for companies like ours, because it keeps podcasting open and it enables innovation to happen. For a long time, there hasn't been a lot moving forward in podcasting, and that's really because it was just Apple running most of the show.

Tim Schigel: Yeah, no, I love that. Love to be able to dig deeper in some podcasts when I'm listening, not always, but sometimes. You want to explore more and not get too far afield, and I think there's a lot of room for improvement there.

Mike Kadin: And a transcript that kind of is intelligent, can start to help you understand what the content means and how it can be linked to the rest of the world, can really start to open some doors. Then on the back end, for companies like us, we are less interested in the actual listener experience and more in what we can do for podcasters. And I think as that ecosystem evolves, we're going to be wanting to think about all the different ways that we can help podcasters make money from their work and grow their audience. And so there's lots of other places to go just besides advertising. We already do listener payments. There's a group that's trying to figure out how crypto fits into all of it. There's merchandise, there's live events, there's lots of ways podcasters can grow and there's lots of ways that they can earn, and we want to be at the forefront of making that happen.

Tim Schigel: Perfect summary. If you're a podcaster and you want to make more money, talk to Mike.

Mike Kadin: Sure. Yeah, send me a note.

Tim Schigel: Mike, thanks for being on Fast Frontiers, this was a pleasure and I'm sure our listeners are going to get a lot out of what you shared and your experiences. Thank you.

Mike Kadin: Yeah, thank you. This is fun.

Tim Schigel: Join us next time when we bring you my conversation with Bernadette Butler, CEO and co- founder of StoryTap in Vancouver, Canada. StoryTap is a video platform that helps brands give their customers and employees a voice by sharing video stories to increase brand engagement, conversions, and retention. Thanks for listening to Fast Frontiers. If you like our show and want to know more, check out our website fastfrontiers. com. If you've enjoyed this episode, please share it with others and leave us a review on your favorite podcast platform. The Fast Frontiers Podcast is brought to you by Refinery Ventures. Our producer is Abby Fittes. Audio Engineering by Astronomic Audio, and our podcast platform is Casted.


On today's episode of Fast Frontiers, host Tim Schigel sits down to speak with Mike Kadin, the CEO of RedCircle. The two discuss strategies for managing high-growth companies, lessons learned in hiring and how Mike met his co-founder Jeremy Lermitte.