Beyond Financial Success with Brenden Mulligan

Beth Davies, host: Welcome to Career Curves, where we talked to people who have interesting careers and explore how they got where they are today. I'm your host Beth Davies. 

There are many people who start their career in one area and then find success in another. These seemingly unrelated moves often make sense once you hear the person's story. That's the case with our guest on this episode, Brenden Mulligan. 

Brenden started his career in the music industry and then stepped off this path to be a startup founder and develop products. Four of his startups were acquired including LaunchKit, which was acquired by Google. Currently, he's head of product at Commonstock and founder of Podpage. 

So how did Brenden get into tech and was it a complete departure from music? Well, I am thrilled to have him here to share his experiences with us. So welcome, Brenden.

Brenden Mulligan, guest: Thank you very much for having me.

Beth: So, let's start by talking about what you're doing now, and I know you've got a couple of things going on, and so let's start with the one that's actually how I met you, which is Podpage.

Tell us what Podpage is and what your role is with Podpage. 

Brenden: Yeah, totally. So Podpage is a very quick and easy way to create a website for a podcaster. I started it and spent a lot of 2020 building it, growing it, being sort of the chief architect / customer service rep. So, I was actually doing the design work, the engineering work, all customer support, which is probably how we met. And the reason I basically did that is if you're going to build something, there's no way to figure out what to build next without talking to users. So, I sort of obsessively talk to users.

At the end of last year, the product reached a level of maturity where I could get some other people to help come on and do some of the engineering work and some of the support work. 

So, it's been great. It's been a really fun project to work on and I love being involved in it. Luckily, I get to sort of hand a lot of the day-to-day stuff off to other people. 

Beth: When you're starting something like Podpage, at what point do you actually start to get others involved as opposed to doing it all yourself? 

Brenden: For me personally, I try to do as much as possible for as long as possible. There's a lot of people that would say the opposite. "Oh, I want to come up with an idea. I want to hire a team to build it. And I just want to sort of help steer it, but not be involved day-to-day." And there are some projects that I would probably do that for. 

For this, it was just like my hobby. I don't have a hobby of like woodworking or any sort of craft. Building software would be my craft. And so it's always just fun. So, when I find a project like this that I just love working on, I don't bring on people as quick because it's just more fun to keep building it.

 The part that I started realizing was when I wanted to spend more time working on different things. And also, once I learned a lot from the community and a lot of the questions were more, I would say, maintenance type questions of just people having general questions about how to use the software, I started realizing the interaction with customers on an hourly basis wasn't giving as much value to me as far as what to build next, and so having some people come on and help with that. 

And then on the engineering side, I'm a decent programmer for very rudimentary projects, but when it gets complicated, I'm no longer very valuable. So as Podpage got more complicated, bringing on people to help build it was necessary because it just needed more complexity that I didn't know how to do. That's how I approach it. 

Beth: So, at the start of 2021, you actually took on a new role at Commonstock and I think building out the Podpage team allowed you to do this. Tell me about the new role that you have. 

Brenden: So Commonstock is a finance technology company. The initial product is a social community that talks about what stocks they're buying and they're selling and their strategies around investing. 

I started coaching the CEO about halfway through last year. We were introduced by one of his investors who was one of my previous investors. And he was looking for help with just structuring how he wanted to build a product, how he was going to build the product team. And so, we met in that capacity and I learned more about the product over that course of time and just built a really great relationship with him. And by the end of the year started talking about coming on full-time and joining the team. 

For me, I think once you've started companies on your own, the thought of joining someone else's company is a little daunting because it's just a very different role. I'd been recruited a lot of times to join more mature startups, be a product manager, and way earlier sort of become someone's co-founder. 

This was just the perfect phase for me, because there's an incredibly motivated, inspirational, experienced founder that kind of knows where he wants the company to go, but he's a first-time founder. And so, the thing that he really needed was someone who's kind of done it before, can see around corners. He had gotten this amazing engineering team to build a really incredible product, but there was just a lot of shortcuts taken because of how quickly they needed to move, and he was transitioning to needing to go a little bit more process oriented and start building out a long-term product team and engineering roadmap that the company could scale with. And that's kind of the sweet spot for me. 

I've always been interested in finance and a lot of investing is evaluating companies and thinking about technology companies, and so for me, it's a perfect fit. 

Beth: How are you going to balance the two different roles, the Podpage and the Commonstock? 

Brenden: Commonstock is my job. It's my 8:00 - 7:00 job. This is one of the reasons at the end of last year, I started handing over the reins to a few other people with Podpage. I'll check in on the customers in the morning and the evening. I'll build some features on the weekend, but I also have other people working on it throughout the week. And so, it worked out really well by the end of the year, the product was in that mature state where I could step away and it wasn't a big loss to Podpage.

Beth: So, you can lead it without necessarily doing it like you were a year ago. 

Brenden: Exactly. There's a balance there and so far, it's been totally manageable, but I told the CEO when I joined, I was like, "if this ever becomes an issue, let's just talk about it," but at this point, its relatively passive.

Beth: I think sometimes we underestimate the power of "let's just talk about it. If there's a problem, let's talk about it." 

Brenden: Yes. 

 The only thing I'd say about it is that I actually love when people on my team had side projects, because if you're only thinking about the same kind of problem all day, your brain kind of gets wired into solving that type of a problem.

I love hiring people who do side projects. It's cool to know that when they go home, they're still thinking about software development, which is beneficial to what they're doing during the day, but they're thinking about it for a different market or a different phase. Or when they're at home, they're a designer, but when they're at work, they're a product manager, but that means when they're at work, I can talk to them about design.

 I think there's a lot of benefit as long as you can keep the balance and one doesn't take over. I think it's great. 

Beth: All right. So, let's find out how it is that you got where you are today. And let's go back in time, all the way to your childhood. Tell me about your family and where you grew up. 

Brenden: I grew up on the east coast, small suburb of Baltimore. Middle-class family, but I did come from a family where, when you grew up, you were a doctor or a lawyer. My dad was a bond trader and it was very much like, "Go to school. Get a good degree. Get a good job. Have that job for as long as you need to have the job." People would of course say, "What do you want to be when you grow up?" but it wasn't like dream big. It was sort of like, "Which career do you want to have when you grow up?" 

And so, when I was graduating high school, I started getting interested in filmmaking. When you're on the east coast, all of the Ivy league schools are up and down the coast. So, it was sort of like, "Where are you going to go to college?" 

I went to Vanderbilt in Nashville and everyone was like, "Oh my God, that's another world," but for me, I wanted something totally different. 

And so I went to Nashville, but sort of interested in filmmaking and creative arts and ended up, through my time in Nashville, transitioning over to being more in the music business and Nashville is one of the best cities in the world to do that. 

So, started running festivals, working at venues, working for booking agencies, just absorbing that environment because I had the opportunity to work for these great companies that were right there.

Beth: You mentioned a moment ago that you were thinking that you were interested in film and movies. So, what happened to that part of the dream? 

Brenden: Yeah, and this is one of those areas where I feel like my life could be entirely different had I just learned that about myself maybe a year earlier. I had already gotten into college, and I was already planning to go to Nashville and then got very, very into movies my senior year in high school, but I hadn't planned to go to LA or anything. 

So, my honest plan was I'll go to Nashville and probably transfer out to LA or New York or somewhere for that. And when I was at Vanderbilt, I did as much film as I could do. I took every film class and there wasn't very much at all, but I just fell in love with the school. I made a great group of friends. 

I had always been super passionate about music and so I started seeing a whole side where I could actually work in music and this is the best place ever for it. And instead of being a director, which is very risky, I can be on the business side, so that feels a little more responsible. And so that's what led me to that. It was just the availability of having that all at my fingertips.

Beth: I'm surprised by what you're saying, because as I was getting ready for this interview, I saw that you majored in Human & Organizational Development, which is essentially an HR type of degree. Not music and not even the business side of music. What was going on here? 

Brenden: This is when I will be thrown out by my alma mater. 

So, I didn't know what I wanted to do. I knew I wasn't going to be like an English major. I didn't want to do econ. And that major objectively was the most generalist major I could find. And it was also, and this isn't why I picked it, but it certainly benefited me for all of the extracurriculars I had, it was significantly easier than a lot of other majors. While my friends were doing problem sets for econ, I was thinking about how the brain develops and how that changes how people act in organizations. 

Or they really stressed internships, so they were like, "Get out and have experiences," which people hated because you're spending all this money to go to Vanderbilt, and they're just basically saying, "This semester, you're going to work for someone," and my parents hated that, but for me, it was like, that was the best education you can get. It gave me such a good opportunity to apply everything I was learning to an actual business environment. 

So, I wouldn't think of it as HR as much as the major was structured as think about how the brain develops. Think about how humans do what they do and why they act the way they act. And then think about how organizations are structured. And then think about how these humans actually participate in organizations, and then what works and what doesn't work about it.

I've never had a job since where I didn't apply something directly that I learned from that major, but it had a really bad reputation because there's so much subjectivity to it where every other major was more objective. A lot of our assignments seemed like fluff and honestly probably a bunch of them were. My biggest feedback to some of the people at Vanderbilt was, "This is, I think, the best major you can have, you just need to make it harder so it doesn't have the bad reputation because every job I bring in frameworks and stuff that I've done in my major." 

All my other friends were like, "Cool, I learned a bunch of stuff at school, but I haven't applied it yet. I'm going to have to relearn everything when I get to Wall Street or get wherever." For me, it was like I was using these frameworks on day 1.

Beth: I totally can see that because how the brain works, what motivates people, what drives people... If you're developing product and you want to attract customers, that's all about how do people respond to things? What motivates people? What interests people? What engages people? And that's exactly what you were we're studying.

Brenden: And why do people act the way they do? Every job I've ever had the end result of whatever we're building ends up being really just the result of a bunch of communication with a bunch of people and getting everyone to work together and be aligned. If you don't have those basic skills of understanding what motivates other people, then how do you motivate them to do the things that the company needs them to do? 

 So, it was one of those majors that the content was also valuable and could it be applied to anything, but you had to really come out and know how you are going to apply it. It didn't prepare you like, "Oh, cool. You got an econ degree from Vanderbilt; therefore, you can work at Morgan Stanley." It wasn't like a good qualifier, but if you came out and found a job, you could usually apply it to anything. 

Knowing that I was going to lean into the music industry, there was no music industry degree and so for me, it was a really good opportunity just to have something that I knew I could apply to a lot of things.

Beth: So then as graduation was approaching, what kind of a plan were you putting into place for how you were going to break into the music industry? 

Brenden: One of the things that was nice about that major is it did require you to spend an entire semester working full-time for a local Nashville company. Through a bunch of activity that I was doing in and out of school, I was able to land an internship in Creative Artists Agency, which is arguably the best talent agency in the world and they have a Nashville office. So that was when I was in school and that's one of those jobs when you have that, you can work anywhere. 

And so, coming out of school, it was really more about I didn't think I wanted to be a booking agent. It wasn't creative enough for me. So, I wanted to try something else in music and one thing I hadn't tried was working at a record label. 

I could go to New York, LA, or there was this outfit in Chicago called Aware Records that was the record label for John Mayer and a few others. This was back in like early 2000. So, kind of a bunch of the hot acts were coming out of this random little label in Chicago and it had a joint venture with Sony, so it kind of had the power of the big guys, but it was a small company. And as you can tell with my resume, I like small companies for the most part. And so that was where I went. 

So, I went and moved to Chicago. I'd never been to Chicago, but I packed up my stuff a couple days after graduation and drove a U-Haul to Chicago and spent most of my twenties in Chicago, working in music.

Beth: I want to ask you one more question about Creative Artists Agency before we move on. As prime as that type of an internship is, do you remember what you did to get that internship? How it came about? 

Brenden: At Vanderbilt, there was a huge music festival every year, and I ended up being in charge of all the music for it. I think I volunteered to be the website guy my freshman or sophomore year. Maybe I made t-shirts. And then I was very organized and I just did that job better than anyone had ever done it. And so, then they were trying to figure out who was going to actually be the talent booker to pick the bands and negotiate contracts, and so I got to do that as a junior. 

When you're booking bands or when bands book a show either you're, you're saying, "I want you to play this night and here's how we're going to split the ticket sales," or you give them guaranteed payment. Colleges generally are guaranteed payments. Booking agents love colleges because of this and bands love colleges. So, I was able to call the best booking agents in the world and basically say like, "Yeah, I've got a checkbook and I'm looking for bands." 

And so that just allowed me to get a very good network relatively quickly. Again, I was also super organized. The festival I put on at the time was one of the biggest in Nashville and we had gotten national news the year before because we booked Nelly on his rise. Again, this is back in early 2000s.

When it came time to do an internship, I was just talking to John Mayer's agent and we were just literally having lunch because we hadn't gotten to know each other, and he was like, "Oh, you should just come do an internship here." It was literally that easy. I don't even think I did an interview. It was just having built trust with someone and he was one of the most well-known agents in the industry at that point. And so, that was it. 

Beth: You've just mentioned a couple of names that I've heard of: Nelly, John Mayer. How do you keep your composure when talking to people who have big names like this, especially here you are a college kid? Where did you get the confidence to step in and have these conversations and make these requests of them?

Brenden: So, to be clear, most of my requests of people were on the business side. It wasn't on the talent side. And so, I wasn't necessarily talking to Nelly. I was talking to Nelly's tour manager or tour manager's assistant. And I think it's not so much about how I kept my composure. I just sort of knew my place.

They weren't there for me to be buddy buddy with them. They were there because we paid them to be there and we needed to make it as easy as possible for them to come to town, put on a show, and get out of town because they had to do it again the next day. 

Beth: What I appreciate though about what you're saying and the idea of knowing your place is that you also knew "I've got something that's of value to them, like the booking, and so I'm going to be strong with the idea that I've got something of value to you. I'm not going to be apologetic about that. I'm offering you something and then using that to open up the door." 

Brenden: Yeah. I mean, for most talent of any kind in my experience, if you do your job well, you don't exist and everything is smooth. And the reason that you get hired or referred to someone else is because they're like, "Oh, I went on tour and the tour really well. There weren't any big disasters," and they're, "Oh my God, who was the tour manager?" Because if your tour went well that's the best thing you could do.

It's not like, "Oh, this guy's great. He's great to drink with." You're there to do the job. 

But I think that's been the same with working in startups and working at Google. The engineers that I recommend did amazing work, deliver things on time, and I interact with them less because they're just doing their job and they ask the right questions and all that. 

Beth: Let's go to Aware Records, so the job that took you to Chicago. What did you go there to do? What was the role that you were going to launch your career doing? 

Brenden: Oh, so dumb. This was 2003. So, iTunes had just come out, but most people were still buying CDs. Amazon was just getting started. And if you were an independent artist, you couldn't sell your CDs online. Aware had seen this opportunity and so they set up online stores for their artists. This was not easy to do at the time.

And so basically as Aware started selling their own CDs, a bunch of Aware's circle came to them and said, "Hey, can you sell ours too?" And so, they actually set up a whole business that was an online store. It was called the Awarestore. 

And so, for me, I just wanted a job at Aware. And so, my first summer was an intern at Aware. An unpaid intern, packing boxes, shipping CDs, and fulfilling orders. That's what I did. My dad was not thrilled with the result of my college education, but for me it was just like I got in, to be able to meet more people, and again, just do this one thing really well. 

I was interested in technology, so some related to that. I can't remember how long I did that for. I think it was the first year and then moved on to be the assistant to the founder of the label. So was one of his assistants. 

In the entertainment history, the assistants are like the gold position. You really get access to everything. You get to learn really quickly. It's all crappy work for the most part, but there's no closer place to be able to learn as quickly. 

Beth: Yeah, and at that stage of your career, that's everything. 

Brenden: Exactly. 

Beth: Now on LinkedIn, it actually shows that you go from Aware Records to Awarestore.com. Now you kind of just clued us in to the fact that those kind of were the same company or... 

Brenden: Well, originally it was the same company and I worked for Awarestore, which was just part of Aware Records. And then, when I left Aware, Awarestore had been kind of separated and sold off because the business had gotten big enough and it was so different than what Aware was doing that they just needed to be different entities. 

And so, I did go and help the head of Awarestore for I think it was about a year. Again, it was like I was interested in technology and so it was a good opportunity to go and just play more in the tech space.

Beth: You went into Awarestore with a pretty big title, as VP. And you're, if I'm calculating right, still about in your mid-20s and you're carrying this big title. How important was a title like VP to you at this point? 

Brenden: To an immature 25-26 year old, it felt important, but it was a sign of immaturity.

I was actually having this conversation with someone the other day. A CEO is a good role to have when you're doing a startup, because someone needs to be clearly in charge. And if they have a co-founder that's a technology person, a CTO I think is an acceptable thing because you have two co-founders, one shouldn't be a C and the other not a C. But outside of that, I think startups just shouldn't have titles in general. 

My title right now is Head of Product. And what does the Head of Product? It doesn't really mean anything, but it does mean if there's an issue with the engineering design or product function at our company, it ultimately is my responsibility.

Chief product officer is a dumb title when there's not a big org underneath. At that point though, in my career, it was everything. 

Beth: Did you get a different reaction this time out of your father? 

Brenden: You know, he had a very traditional career. Go to work at a Wall Street company, do things with money because it was a good way to make a career.

I can't remember the timing, but I decided to go back to business school. And I remember when I went back to business school, one of the main things I was excited about was telling him that I was going back to business school because it would sort of make sense to him. He passed away about 10 years ago, but at the end of his life, I remember, he still was a little confused as to what this whole music industry thing was, but he knew I was happy and I wasn't asking him for money. 

But yeah, I think at this point he'd be proud. You know, when I was interested in tech, tech was like this weird new thing. I think at this point, he'd be like, "Wow, you were interested in the thing that was on the horizon." Where he thought I was interested in the risky thing, it ended up being something that paid off. 

Beth: Well, you just mentioned exactly what I wanted to ask you about next, which is your interest in tech. When did you start to notice this developing and what was it that was catching your imagination?

Brenden: I have been sort of more into computers than most of my friends since high school or since middle school, and a lot of it has to do with my stepdad who is similar. He doesn't come from the tech industry, but he's always been just obsessed with whatever the next greatest gadget is. And so, he got me into that, too.

And so, in high school, I was one of the few kids that had a computer of my own in my room and I was on message boards, and I was like a logo developer. All of this stuff. I was just interested in technology and so that sort of kept its way through a lot of what I did. 

So, when I joined the music thing, I was the website person at first. And when I joined the record label, I worked on the website and then did the record label thing and then ended up leaving being a traditional music industry person to build out a piece of software for the music industry. And so, it just kept coming back. 

Beth: Tell me about the software you built for the music industry.

Brenden: So, the honest thing was when I was working as the assistant, I spent a very large amount of my day updating content all over the internet, which was new. There were about fifty Myspace copycats. We didn't know which was the most popular and so we had to keep content up to date with all of them. So, like, as an example, if John Mayer got a new batch of tour dates, I would spend a day keeping them up to date everywhere and updating his website.

It was so much and so that's the specific problem that I saw that I thought should be solved some way. I didn't even know what a startup was. I didn't know the difference between a startup or a website. I just knew there's got to be an easier way to do this, so I partnered with someone on the technology side of a label that we worked with, and we started building out a solution for this.

It was just like, "Yeah, let's solve this problem however we need to solve it." 

Beth: You mentioned a moment ago that you started an MBA. Why did you make the decision to go for an MBA? 

Brenden: Initially, my girlfriend and I were looking at potentially moving to San Francisco. I'd been doing my own little startup for a while and it was going well from the standpoint of the users loved it and it was becoming important in music industry. It was going poorly as I had no clue how to monetize it and I was going into debt. 

And so, we were thinking about moving to San Francisco and I thought, "Well, I probably shouldn't do this startup thing full time. What do I want to do next? I don't really know. So maybe I'll go back to school." And honestly there was that hint of, "I think dad would love it if I went back to school. Right?" And it seemed like, "Oh, I'm not good at this business thing, so maybe it'll help." 

And so, I applied to Stanford and Berkeley. I think I was wait-listed at Stanford and got into Berkeley, and I went to full orientation, paid a deposit, and then we ended up staying in Chicago. I sort of in my mind was already going to business school. So, I was like, "Oh, I'll go to Kellogg," which is an amazing business school. Total waste of money for me, but an amazing business school on its own. I just didn't really want to be in consulting or marketing. That just wasn't really what my passion was. And it's a great business school for those things, but it's not good for startups or it wasn't 15 years ago. And so, I went back and completed half a degree. 

Beth: You completed half a degree. What happened here, Brenden? 

Brenden: A lot of people that would go to business school, the money came from their current employer. A lot of times you would be working your way up in your consulting company and there was some sort of a ceiling where they said, "Cool, you've gotten promoted, but in order to get the next promotion, you need an MBA. You go back to Kellogg; we'll pay for it. Then you come back and work for us for a few years." so that was, I think it still is, a very traditional way of people getting their MBAs. 

I was a startup guy with my own company, so I was paying for it with government loans and student loans. And so, I was acutely aware of how much I was spending on every class and at Northwestern at the time, it was 10-week classes, one night a week because I was in their part-time program. I think it was $4,500 and it was three-hour classes. So, $4,500 a class. So that's $450 a class. So, $150 an hour. 

I was going into a lot of debt with my startup and so to go into another set of debt with school, I was really meticulous about making sure I was getting value out of it.

And so, two things happened. One, after about a year and a half, I just didn't feel like the subject matter I was learning was actually helping me at my company. And I had spent a year and a half being like, "When is this going to kick in?" and it just never seemed to kick in. It would have been great if I was a consultant or at a more traditional job, but for me it wasn't as valuable. And so, I was starting to feel like every time I forked over money or basically signed to go into more debt, I couldn't justify the debt that I had already gone into. 

And then, as my startup got more complicated and I had to do more travel, I started missing classes. And so, I started being like, "I'm the type of person who's clipping coupons to save five bucks or going down to dollar burger night at the bar to get dinner yet I'm fine skipping a $450 class?" Like I would never burn $450, but then there were some nights that I was just working on my startup, that I would just not go to class. And I was like, "I would never just waste this money," so I just realized how little I valued it. And after about a year and a half or two and a half years, I forget how long, because it's a night class so it takes a lot longer, I just realized that I wasn't getting the ROI for it. 

That was a pretty easy decision because it was sunk cost. I'd already spent the money. So, it was a "Do I want to go another $50,000 into debt or do I just want to cut it here?" So that was an easy one. 

Beth: So here you are. You're dropping out of business school. You're doing a startup that is going more and more in debt. And so, tell me what happened next? How did you pull yourself out of that? 

Brenden: I got, I wouldn't say totally lucky, but the startup although it had not been financially successful was enormously popular within the music industry.

And so even though it was costing me a lot of money, I was speaking at a ton of conferences. Everyone knew it and it was being used by record labels and it was being used by independent artists. I think it had 50 or 60,000 artists using it. 

Beth: What was it called by the way? 

Brenden: It was called ArtistData, about the least creative name that you can put for a data company that deals with artist data.

So not a great business, but a great brand from a standpoint of people thought it was awesome. The people loved it. And I started monetizing in a really complicated and dumb way, but it started making a little bit of money, which was nice. Ultimately what happened was another small music company came along and bought it.

I remember people being like, "How much did you sell it for?" And it was a life changing amount of money for me. It was life changing. It basically just got me out of debt. I basically had spent all this money on this startup education and at the end of it, I was pretty much at zero, but me being at zero is the best. 

I have a friend investor who kind of went through this and he was like, "The best feeling I've ever had was when I got to zero. It wasn't when I made my first million bucks. It was when I got to zero." 

Selling it to this company, it was called Sonicbids, they were based in Boston. They wanted a West Coast presence. I wanted to move to San Francisco. So, I got to sell the company. I got to move to San Francisco. It was great.

So, it was a, it was a very, very good outcome. 

Beth: You mentioned earlier that there's a real difference between leading a company that is your idea, you're building it, versus working for somebody else with it being their company, their idea. And so now with this acquisition, you're going into this company and you're really working for them and their idea.

So, what was that experience like for you? 

Brenden: It was good. The nice thing about being acquired, depending on how an acquisition works, is it was important to them because they had a name to maintain. They didn't want to just kill ArtistData. They wanted ArtistData to be part of what they were building.

So, the year that I spent with them was majority focused on integrating the key parts of ArtistData into their system. And so, although I was a part of someone else's thing, I kind of was still running this tiny little thing. I was working with the same team I had always worked with to integrate it. I was working with the same customers to integrate them. So ultimately, I helped somewhat with their strategy. 

I think I had a dumb title there, too. I think I was like VP of Product Strategy or something. And I think that was equally as important to me at 29 as it was when I was 25. Stupid.

But I would say that I was definitely working for him, the CEO, but most of the time it was like, "Keep working for your users and your customers." The goal was they wanted all those customers to become Sonicbids customers and so it was let's make this transition easy. 

 I stayed for a year to help with the transition and then moved on. 

Beth: Tell me about the move on. Where'd you go? What'd you do? 

Brenden: Let's see. That would probably be like four and a half years after starting the business and so I just needed a break. So, I did some consulting, but really spent a few months just living in San Francisco. Meeting tons of people. Just enjoying the change. 

I wanted to spend more time learning to code and design and just kind of be a little bit more self-sufficient because up to that point, all I knew how to do was ask designers to design things and ask engineers to build things. If I wanted to start an idea, I needed a team and I kind of didn't want that. 

And so, I spent a few months learning to code and ended up launching a small product called Onesheet, which was focused on musicians. It wasn't intended to be a startup, but that ended up becoming really popular and I did that for about a year. And that was basically a website builder for musicians. That was kind of like Podpage. It was just basically a side project for a year while I was figuring out what I wanted to do next. 

Beth: That small side project you worked on for a year, Onesheet, it got acquired, didn't it?

Brenden: That got acquired by a more traditional website builder for musicians called Sitezoogle. It's sort of like a Squarespace focused entirely on musicians, or it was at the time. And so, for them, they saw it as a great acquisition channel because my thing was way easier to use than theirs. And it had very few features and so they saw it as a good steppingstone into what they were building. 

Beth: What is that personal experience like?

Brenden: I don't know. It's different. I remember talking to my executive coach about it and it was like, "You just have to mentally prepare for the closing of a chapter that is in your past now. You're publicly saying it's over and you must mourn that loss, even if it's something that seems like a positive experience. It's still a loss and there's still some sense of mourning that you'll go through." 

Beth: That's just so wise because, of course, everybody else around you is slapping you on the back and congratulating you, and yet internally there's a whole different experience going on. 

You started two more companies after ArtistData and Onesheet that were also acquired. One of them, LaunchKit, was acquired by Google. Similar experience? 

Brenden: Selling the company to Google was probably one of my biggest professional accomplishments. But that process was probably one of the worst, worst things I've ever been through, just because of all the emotional turmoil that you have to go through when you’re negotiating. When you're negotiating, the other person is basically saying, "We're going to try to convince you you're worth nothing. As little as possible." Right? And you have to say, "We have to convince you we're worth something." And it's just months of tiny details. 

There's a picture my wife took of me. We went to Mexico right before I started Google and it's a totally empty beach and you can barely see, but I'm just lying flat. And I think her Facebook caption was "He finally found the peace he was looking for." 

I feel a physiological change even talking about it years later because it was just such a process. There's so much ego wrapped up in it. At any point, it feels like the deal is going to fall apart. It's a long process. 

My co-founder and I still have a drink and talk through how awful those months were, but that ended up leading to something that was really wonderful. But it's hard. 

Beth: With the acquisition of Launchkit by Google, this meant that you went to work for Google. 

Brenden: Yes.

Beth: Clearly the largest company you had worked for. Tell me about that experience. What did you do there and how was that for you? 

Brenden: It was a great education in a totally different area that I had never had experience with before, but also a total destruction of self-identity and having to rebuild a self-identity in a totally different environment.

I went into Google as a CEO, as a designer, as an engineer. I'd actually never been a product manager before. And as an acquired CEO, you kind of get put into the product management ladder, unless you're the technical co-founder or something like. 

And so I went in thinking, "Cool, I can be a PM, but I'm going to still build stuff. I'm going to still design stuff." And I had to sort of realize that at these bigger companies, the role is a lot more defined. There's a lot of power in not doing the designing or engineering, but for me it felt like my superpower was being stripped of me and the only thing I was left with was product management, which is not something that I had formal education in. 

So, I felt a little helpless. I was like, "No, no. The reason that I'm going to be good is because I can do all this other stuff," and it was like, "No, at this company, you don't need to do that stuff. We have thousands of people to do that stuff." And so, for me, it was a lot of just sort of learning how to operate in a big organization, which was an amazing education for me.

I don't think that that's my place in the world. I am a little more impatient when it comes to how quickly I like to build and ship things and how decisions are made. All that stuff. I think I'm very competent in a big company, but it's not where I love being. 

The cool thing about working for Google is it's like 50 companies in one and so when you feel like you're not in a great role, you can transfer to a different role. And in the real world -- I was on developer tools -- I couldn't be at a developer tools startup and then just transfer over to a self-driving car startup. But you can do that at Google, right? If you can show that you're just a good product manager, everyone's happy to have you on their team. So, I almost ended up working for Waymo. 

I ended up choosing to work in the G Suite enterprise world and I'd never worked in enterprise. So, I got to learn all about enterprise software. I got to learn about developing for big companies. I tried to find the opportunities within Google that I wouldn't be able to just do on my own elsewhere. So, it was great. 

And I spent three years there and it was a good three years. And then I was ready to get back to building. 

Beth: I was going to say, so what caused you to finally decide, even though there's all these opportunities and you can move to other products. What made you finally decide it's time for me to move on? 

Brenden: Functionally, when you go in through an acquisition, you typically have some sort of an earn-out and that earn-out is usually a bonus that's paid to you on a yearly basis. I get why they do it because they want to keep you. They want to spread that out over a bunch of years. 

I think the mistake with it, the way that they structure it -- and this isn't Google, this is almost everyone -- is that it gives you these very specific points where you have to think really hard if you want to stick around for another 11 months.

As an acquired founder, I think most of the time it's over four years. I knew I didn't want to stay for four. I was pretty sure. And around two and a half, I was like, "I've already spent half of the year here. I might as well stay for the other six months." And I kept adding value, but I think that I probably would have left a little earlier, had I not had that very specific date.

So, at three years I was like, "well, I'm definitely not going to stay another year, so I should get out now as opposed to waiting a day longer because I don't get rewarded for staying any longer." 

Beth: So far, you've talked about a couple of startups that you were involved in that all were acquired. Have you been involved in any that didn't have that same outcome and maybe even went the other way, which is they failed? 

Brenden: In total honesty, I would say that startup wise I've always managed to right the ship and end up with a good outcome. So, like I said, the first one, huge failure from a financial standpoint, but ended up being net zero, which some people would think is a failure. I was thrilled with it. But other people would be like, "Well, wait. So, you worked for five years and you ended up just not in debt?" So, some people could say that wasn't a successful exit. I thought I was great. 

So, I would say that the Cluster was generally a failure when it comes to turning it into a venture scaled, consumer success. But with building Cluster, we learned how to build Launchkit and that ended up being successful. So, Cluster was basically a failure, although it still exists and has millions of customers and people still love it. From a startup perspective, it was not a success.

And then over the past year, I built 10 or 15 different products. While I was building Podpage, I was building a ton of different stuff. And I think 14 of them, I would say, would be total failures, but they weren't intended to be big things anyway. They were more little experiments. 

So, plenty, plenty of failures.

Beth: When you left Google, I think this is pretty recent. This is about 2019, if I'm right. 

Brenden: Yeah. 

Beth: So, what were you thinking you were going to do as you left Google? 

Brenden: The part of me that I had been building at the beginning of the decade was learning how to build. Learning how to launch. Taking an idea from zero to one. And I kind of had lost that because I'd worked at the same startup for years and then Google for three years. So, I felt like that muscle had atrophied. 

So, I left with the goal of, I didn't have a specific number, but I want to build something new every month. Basically, it was like, I can't build anything that should be venture funded because that tends to be more complicated. So, it had to be super simple. 

Some stuff I built literally in the course of a few hours, but I just wanted to get back into the routine of: Identify a problem. Come up with a solution. Simplify the solution. And then launch it to the world. And I just want to do that as many times as possible. And so Podpage was I think number four of 12, but that was the goal. 

And I said to my wife -- I think I left in August -- and I was like, "By next August, if I have not figured out what I want to do next, I will immediately start looking for a job. That's the deal." I took a little bit of money and put it into a savings account. And I was like, "This money will pay these three expenses for us and so we shouldn't worry. It'd be better if I was working, but the thing we don't have to worry about is running out of money for our mortgage or whatever. But by August, we'll need to start thinking about that. So, my commitment to you is give me a year." I did a ton of consulting and other stuff too, but "Let me be lost for a year and then by August, if I still am lost, we will make some changes." 

Beth: This is a pretty powerful move that you made, because you mentioned that one of the things for you at Google was that you had kind of lost yourself. And so, giving yourself this time to rediscover yourself, find your footing, pick up some things that you had left behind is really smart and kudos to you for doing it. 

And so, one of these was Podpage. You are not a podcaster. At least I have not seen that in all of these things that you've done, I have not seen that you're a podcaster. How did you find this problem to solve? This idea that podcasters need an easier-to-build website?

Brenden: This isn't that interesting of a story. I'd built this before for other creators. I love helping creators. I have some friends that have podcasts. They don't have websites. I spent a day looking into it. 

The most powerful thing about podcasts is that the data actually is public. Like when iTunes or Apple Podcasts reads it or Google or Spotify, they're all reading a podcast feed, and that feed already has all the content in it that you really need to have a website. And so, for me, I was like, "Oh, this is really cool." The hardest part about building software is getting a new user to sign up and then enter a bunch of data, and so this was done. 

So, I basically asked a friend of mine who had a pretty popular podcast if I could use his as an example... Actually, no, I don't think I asked him. I just did it. I spent, I think it was less than a day building him a basic website that was powered by his data. I asked him if I could put his domain name and that was it. It wasn't intended to be a real thing. 

And then I showed it to some other people. I built sites for other people by using their feed. And then it was very organic. People said, "Oh, I want to change this," and I was like, "Oh, I don't have any way for you to log in and do that. I guess I should build that." 

Or, "I want to add a custom page." 

"Oh, I guess I could do that."

I will say when you build product, it is way better to have a clear idea of what you're going to build and build it right from the beginning. It definitely is the best way. I've never experienced that with a product, because most of the time you need to have a bunch of customers to tell you what you need to build.

And so Podpage has just been this winding road of feature request after feature request, and getting to know the community, and just being there to answer questions, and listen to them. 

Beth: I'm very grateful that you built Podpage. 

Brenden: Once you start building something and the audience that you're building for is so vocal about how needed it is, it makes it a lot more fun to keep going. 

There are so many products I built in the past year and a half that I thought are amazing. I bought this travel guide product, which I love. No one wanted it. I expected people to be like, "Oh, this is really cool. I want to use it." 

Everyone was like, "This is so stupid." 

You get so much feedback when you put stuff out. 

I launched one thing that was going to help startups measure some data and I literally thought it would be my next startup. I was worried that it would get too big too quickly. And the day I launched it, I think two people signed up. And I was like, "Oh, maybe the messaging is wrong," and then after doing a bunch of customer interviews, it was like, "No, it's just isn't needed." 

But with the podcast stuff, everyone started flocking to it. Podcasters are a hard community to get in front of because there's not a place they all gather, and so the marketing and the distribution is hard. But once they saw it, a lot of them were very excited. As soon as I saw that, then it was fun to work with and continue to build out. 

Beth: We've now gone through your journey. We are now where we started, which is talking about what you're doing now.

So, I just have four more quick questions. We call these the lightning round. 

And so, the first question is what would you say is the smartest move you made whether intentionally or accidentally? 

Brenden: Smartest thing I did was move to move to San Francisco. No one was doing startups in Chicago. No one. And if I had lunch with someone who was slightly connected to entrepreneurial-ism once a week, all I did all week was look forward to that lunch. And with one flight, I got to a place where every single person spoke my language and I never felt more at home somewhere in my adult life. 

I don't think you need to do that anymore, but if you want to work in tech, it's still the best place to be, in my opinion.

Beth: If you could have one do-over, what would it be and why?

Brenden: Not to beat a dead horse, but I would have moved to San Francisco sooner because I think the first startup I did was fundamentally flawed from the beginning. And I think if I was here, I would have had more people poking it and helping me understand that I shouldn't spend three and a half years on it.

Beth: If you could go back in time to the young Brenden and give him one piece of career advice, what would you tell him? 

Brenden: Don't worry about being in charge so early. I mean, it's funny now, as I enter my forties, I'm like happy to take a job for an inspiring founder at an amazing company. And I think that Commonstock will make everything I've done in the past seem so tiny compared to how big we're going to grow this thing. 

I think 15 years ago, I would have been like, "I'm not going to join someone else's company. I want to be the boss." Right? I wanted to have the VP titles and all that stuff was important to me. 

I coach and talk to a lot of younger product managers, and usually what I say is, "If you have an idea that you're super passionate about, like can't sleep, do it. But if you just want to do it to start a company, go work for any company that is growing. Or go work for Google for a couple of years and then leave. No matter which of those you choose, go somewhere for a few years. Soak up it's like and then leave, and then start your own thing if you want to do that."

But I think I was really focused early on, “No, I want to be the entrepreneur. I want to be the person," and like I said, I'm very happy with how my career is turned out, but I was way too in my own head around needing to be in charge. 

Beth: And my last question, how do you define success?

Brenden: For me, it's just enjoying how I spend my day. 

I was talking to someone a couple of weeks ago. He was interviewing me for something and I just joined Commonstock and he goes, "Oh, so you're doing the day job so you can enjoy the side project." 

And I was like, "I love both." 

And he was like, "Wait, you get to spend all your day working on something that you really enjoy and then at night, you have a side project just because you like it?" 

And I was like, "Yeah, it's great." 

I've been very lucky. I have friends that have been far more financially successful by working at a job that they didn't particularly love, but checked a lot of boxes when it comes to great ways to make money.

And I've always put am I inspired by what I'm doing? Am I feeling like my days are spent well? I put that first. So, for me, that has ended with potentially less financial success in some ways, but I've never had a job. And as soon as I stop liking what I'm doing, I generally try to change course.

Beth: Brenden, thank you so much. I'm really appreciative of your spending your early evening with me because I have a sneaky feeling you've got to go off now and do one of your two jobs. 

Brenden: It's no problem. Thank you for having me. I really appreciate it. 

Beth: Thank you.