Episode 594 | Starting Over with the TropicalMBA’s Dan & Ian

Rob: In this 594th episode of Startups For The Rest of Us, I talk with Dan Andrews and Ian Schoen from the Tropical MBA Podcast. We cover the gamut, but we talk a lot about how they’ve started over. They’ve started a new business after selling their physical products company back in 2015, I believe it was. Then, they run their community, the Dynamite Circle, and they have in-person events and a podcast. It’s very much a sister podcast of Startups For The Rest of Us. It’s just that they don’t focus necessarily on SaaS. 

They saw a need within their community. It’s a need that would be really hard for most people to bootstrap because it is a two-sided marketplace, but Dan and Ian have the advantage of having an audience on one or both sides of that marketplace. You’ll hear how we talk through that in today’s episode. Thanks for joining me as always. Let’s dive right into our conversation.

When I introduce you guys, I never use your last names. I always say, do you know Dan and Ian from Tropical MBA? It’s like Tropical MBA is your collective last name. 

Dan Andrews and Ian Schoen are joining me today. Gents, thanks so much for coming on the show.

Dan: Yeah, a pleasure to be here.

Rob: I described the Tropical MBA Podcast, which used to be called the Lifestyle Business Podcast years ago, as a sister podcast of Startups For The Rest of Us. The two of you are some of the few podcasters who’ve been doing it longer than I have. There aren’t many people I meet who’ve actually been cranking on this. 2009, is that when you originally launched?

Dan: Yeah. I appreciate that. I do feel very similar themes and very similar ethics. One is Ian and I are very concerned that our business chops coming from doing actual business is a bigger deal than the podcast business itself. That’s something that you guys have always had. I guess the difference is that 25% of our audience are developers. The rest are ecommerce owners, publishers, and affiliate marketers.

Rob: Courses, info products, ebooks—that kind of stuff. Crypto, a lot of crypto going on in there. That’s how I think of it too. There’s a Venn diagram of overlap. 

But you came with digital nomadism. That was how you started. The Lifestyle Business and then Tropical MBA—when I used to listen to it, I was like, this is super cool. I’m not going to strap on a backpack and head to Chiang Mai, but these dudes are living this pretty amazing life.

Both of you have settled down a little bit in Austin, Texas now. Do you feel like the digital nomad aspect of the early emphasis is still alive and well? Do you emphasize that as much, or do you feel like it’s more of a business focus?

Ian: I think it’s always hopefully been business-focused, but definitely, we had a lot of lifestyle in there. Obviously, COVID has slowed things down. We are both based in Austin, Texas. For us, there have actually been a lot of huge benefits to that. We got to sit down over the last couple of years and restructure our business in the way that we operate and interact with each other. It’s been amazing because we haven’t really been in the same place for this long together. I thank COVID for that certainly.

Dan: I also want to point out that one of the things Ian and I often talk about on our show is that our digital nomad journey was one of necessity because you were a California developer typing up websites. We were California marketers and manufacturers desperate for development support. We couldn’t afford it in California, so we went to the Philippines and Vietnam to hire our first group of developers and marketers. Along the way in the early days, we were like, this is amazing. This is actually a thing. We’re making money doing this.

We started sharing that journey on the podcast. I believe we were the first regularly publishing bloggers or podcasters that owned a physical product’s location-independent business.

Rob: That’s pretty incredible. That’s the thing. To my knowledge, you never sold the Make Money Online courses. You didn’t monetize the podcast like, hey, we know how to do business and we’re going to teach you how to do it. It’s been so much more about building the community. 

You have the Dynamite Circle, which is a paid online membership community that you had long before we had MicroConf Connect. Then, you have started in-person events. Was that because you heard us (Mike and I) talk about MicroConf? Were you influenced by that? I think you launched those after us because we started in 2011.

Dan: In those early days, we were inundated by emails from listeners basically saying, we really want to know who else is out there. Where are you guys? How do we do this?

Ian and I did launch a seminar business in 2012 where 44 students paid us $2000, but we actually way over-delivered. We had people come to an island resort. They stayed with us for 10 days. We did presentations, workshops, and masterminds every day.

Rob: I remember those now.

Dan: Ian and I just were absolutely exhausted emotionally. We realized we can’t help you guys build a business in 10 days. It was interesting and a lot of great businesses came from it. 

It was during those seminars that we were like, what if we just rented a nice hotel and got everybody together? That was the first DCBKK in 2012. We were there and it’s just like a light bulb went off. We were like, people just want to meet each other and we’re getting more credit for their business growth just by throwing a party than we were by doing 10 days worth of teaching every day.

Rob: That’s the thing. I’ll say before 2009, the old info marketer model—Dan Kennedy and those folks—was always to be the guru. It was, I know the stuff and I’m going to teach you. 

I feel like that model switched with our generation because actually if you go back and listen to early Startups For The Rest of Us, I was trying to be that. I’m like, I know all this stuff. Probably by episode 30 or by the time we got together at MicroConf, I remember thinking that the value here is getting people together in a room like you said. They want the relationships versus no one person here knows it all, contrary to what Internet marketers used to claim.

Ian: Yeah. The guruism didn’t really go anywhere. You can still see that DNA in our marketplace, but I think the transparency allowed this new practitioner-preacher, or we call it the Chops Index. It’s like, watch me do my thing right in front of you every week. That’s solidarity, trust, and peer-to-peer. That’s something that people were probably even more interested in. You want to meet your peers and your people as opposed to kissing the ring of Dan Kennedy if you pay the right amount of money for inner circle access.

Rob: That’s always been something that resonates certainly with me and why I’ve been a listener since 2009–2010 of your show. Why a lot of folks resonate with it is that you’ve always been practitioners. 

While you started the Dynamite Circle community, you had a business manufacturing cat furniture and valet podiums. You sold that business in—I’m going to try to remember this because I believe I heard the episode when I was in an apartment in France with my family. You know those moments where you hear something and it’s like, I remember what the apartment looked like and I remember the kids were younger, but what I don’t remember is what year it was. I think it was 2015, is that right? It would have been fall, September, October?

Ian: I think it was summer because I was in Greece. I remember where I was too. I was on a hotel bed signing these documents. This was the biggest deal that we ever did. I was signing these documents, and then the next day, I got sick. It’s like when all your adrenaline just runs out of your body.

Rob: Yeah. It’s like, I’m signing millions of dollars in documents here. You’re probably doing it on your iPhone with your finger. I did one of those too. It’s the kid’s cello camp and I’m supposed to be in there managing the kid. They’re like, we got to get these docs signed. I walked out, and the teacher gave me a bunch of crap about it. I was like, you need to cut me just a little slack. I am the most stressed I’ve ever been.

You guys sold that business and then within a couple of years launched Dynamite Jobs, which we’re going to talk quite a bit about today. Tell me if I’m describing it right. It’s a job board and an online recruiting help. Those are the two focuses.

I’m quite familiar with it because we at TinySeed proper have used you to help fill two of our roles so far and then a bunch of the TinySeed and frankly, MicroConf companies when they go to hire. I have used your flat fee recruiting service.

This is a lesson I learned. As we were building Drip, I was cash strapped, bootstrapped, and doing all the hiring myself. By the time we got to 10 people, that’s basically half my job for 10–20 hours a week. I was doing it and I hated it. All the recruiters I talked to are like, yeah, 20% of first-year salary. I was like, this is […] insane. 

I was looking all over for a reputable recruiter that I can trust who I can pay $3000, $5000, or a reasonable number because I could have afforded that, but I couldn’t afford $15,000 or $20,000.

When we got acquired, we had two or three in-house recruiters and I was able to basically let them do all the hard work and then just pick the best candidates. I thought to myself, I will never go back. When I leave Drip, if I ever hire again, I’m not doing it myself.

When you guys started talking about it, I was like, this is a baller idea. I believe right now you charge $3500–$3600, a done-for-you recruiting light is how I think about it. You market it, you sift through the resumes, you do the pre-screens, and then you hand the best candidates off. Is that a relatively accurate description?

Ian: Close. The price is a little off.

Dan: We just raised the price. Thanks for the shout-out, Rob.

Rob: How much is it?

Ian: If we do the recruiting for you, meaning we handle the whole process and we place the person in your company, it’s $5500. We do have a lite version of that where essentially, we screen candidates for you, but we don’t actually talk with them on the phone. That’s $2000. Going down from there, we have our posted job offerings basically.

Dan: We do all the promotion. For me, I feel this anxiety when I come to a job board. It’s like, oh my gosh, all the work’s ahead of me right now. I got to compose something that’s interesting. I got to market it. I got to decide whether this is the right job board or not. It’s not like I do it four times a year, so I don’t know if this is the best job for marketers.

I think we tapped into that negative emotion of, we’ll take care of it for you. Don’t worry, just get on the phone with us for 15 minutes and we’ll take care of it for you. That’s this business generation heuristic that we’ve seen over time in our industry which is blank for the rest of us. 

There’s this really established recruiting industry—like you said, 20% of first-year salary—in tech. Everybody knows about it and it’s enormous, but they get so well-compensated for serving in their traditional niche that they’re not going to cross the chasm, come over, and do it for the rest of us.

As our peers mature and become the next generation of business leaders, there’s a big opportunity for listeners of this podcast just to provide professional and marketing services for the rest of us. That’s essentially what our DJ recruiting product is.

Rob: How did you get there? Again, you sold your company in 2015. You’re running a successful podcast. You have an online and in-person community and that’s a business unto itself that is profitable. Where was the spark or the click of, this is what we’re going to spend the next decade working on? That’s a big commitment to this. How did that come together?

Ian: I think the Genesis story of this goes way back to the Tropical MBA, which is essentially trying to find people that we could afford, oftentimes there in other countries, for our business. It was our competitive advantage. Even going back to the manufacturing company back in the day, we couldn’t afford to hire designers, developers, and marketers in California, so we had to look abroad essentially. I think we became pretty good at it and people recognized us as having that talent of being able to find these people. 

There’s another Genesis story, too, which is essentially in DC, which is our community. People were bombing into the forum basically saying, hey, I’m trying to hire somebody. Does anybody know anybody? Hey, I’ve got this job. Would you like to work? It was, in a lot of ways, clogging up the forum. 

There are a lot of different instances of this happening when you own a forum—people coming in and pitching or whatever—but one of the biggest things that we saw there were people trying to pitch job opportunities, so we thought, hey, what if we start marketing these roles for people? That was essentially the Genesis story for Dynamite Jobs.

Dan: We have over 1000 members in there. We were like, if we could just harvest these jobs, that would earn a really impressive audience. Our members are hustling startup founders. They were starting, in some cases, to use our events as hiring fairs. They were realizing that the quality of a remote-first primary candidate, somebody who really understands what we’re doing, is so valuable that they were willing to risk their reputation in the group to build their businesses. They didn’t want to go to indeed.com or other communities that just don’t “get it.” 

We saw that annoyance and that scratch your own itch. People were trying to jump on our bandwagon to leverage our brand to do this anyway. Why don’t we help them turn around and turn an annoyance into an opportunity? 

It was interesting because we just started basically saying, look, we’ll put all our energy into promoting your jobs. Thanks for being clients of the DC private members. We’ll work on your behalf to find great people for you. 

We essentially just did that for years and didn’t make any money. We put a lot of our backs into it and we saw it in the audience. Dynamite Jobs was the fastest thing we’ve ever grown. I always felt like Ian and I were always putting brick after brick after brick. This was really the first thing where we saw some levers. It’s like, oh my gosh, we have 10,000 email subscribers all of a sudden. 

We saw an opportunity during the pandemic to step in with our full-time effort and to try to turn those eyeballs into revenue.

Rob: Got it. Did it start with the job board, then hey, we’re going to allow folks to post and charge a fee, or you weren’t charging early on and you were just promoting?

Ian: We hardly charged anything. A lot of the companies that were posting jobs were DC members so essentially, our value prop to them was, hey, you’re a member of our community. Let us help you find these people that you need. We either charge nothing or very little. 

Looking back, it was amazing the amount of running around that our team did to try and fill these jobs. Our key metric back in the day was the number of jobs filled, which if you look at it is still a good metric. We still keep track of it, but it’s a ridiculous one because half the jobs people post gets abandoned or blown up for whatever reason. As a founder, you change your mind halfway through and here we are, scrambling for basically no money to fill these jobs. 

But it was a really good exercise for us because it taught us actually how to fill a job. That’s when we started to think about the recruiting service essentially. This wasn’t just going to be a job board, per se, but there was a services component behind it.

Rob: What you’re talking about is providing an enormous amount of value for free upfront, more than anyone else would be willing to do. That’s what you’ve done with your podcast. You have hundreds and hundreds of free episodes educating folks, and then you start this job board and you essentially do what anyone else would charge $3500 for a 30-day job posting. They don’t do anything beyond that. It sounds like you just gave value. 

This is one of those things Dan asked me about when I was on your show a few weeks ago. It’s about how I say never bootstrap a two-sided marketplace. You can do it if you have reached into one or both sides of that market. If you already have an audience on one or both sides, it’s much easier.

It’s still hard because you’re fighting a war on two fronts, but you guys have reached into that space and you’re willing to take this approach that not a lot of people are, which is to have staff working to fill these jobs. Nobody does that. That’s why I think this has been successful.

Dan: In 2019, our revenue was less than $5,000.

Rob: But you had the DC basically. You had staff working on the podcast in DC and were able to see if it was that compensating.

Dan: That’s right. Our membership is a profitable business, so we thought, this is a really interesting marketing and services arm. We’re providing these services on behalf of our members from their dues. We have a full-time person trying to maximize the number of placements. That built a lot of relationships on the side.

I do think it’s interesting though. Things changed when Ian, myself, and our CTO, Simon Payne, got involved. That was probably late summer, fall 2020. 

Our website fundamentally looks similar to what it did in 2019 from a passerby. It’s all that stuff that’s happening below the website. That’s a message for makers. Getting on the phone with your clients and having that calendar link front and center, those conversations ultimately led us to our monetization paths. What we’re able to do with that service’s revenue is pump it back into our platform in building technology for our users.

Ian: If you back up a bit, number one, Rob, we cite you all the time. In our meetings, we’ll be like, Rob said not to do this, man. We probably shouldn’t be doing this two-sided marketplace. That still comes up all the time. 

But if you back up and you take a look at Dan and myself, we’re not software guys. We never have been. We’ve tried a couple of times and this is our first go at it. 

If you look at the history of Dynamite Jobs, it was a service-based company. We started with a WordPress site and we started literally running around trying to solve people’s problems. That’s been an advantage for us because we couldn’t just go off and write software to solve these problems. We actually had to physically do the work and figure it out. 

It did get to a certain time where we brought Simon on, our CTO, where we figured out, hey, we’re starting to connect these dots, have a platform, have these profiles, and make it easy for these candidates to apply to jobs. This stuff all makes sense. At a certain point, as marketers, we couldn’t do that. We’re starting to see a lot of these software opportunities, but a lot of these are still very new to us because we’re not software guys, per se.

Dan: We’re the guys that the Airtable people are like, oh, they’re an interesting user.

Rob: You guys are software guys now. You have a CTO who’s writing custom code and I believe you have at least one more developer. You’re running a software company here real soon.

Dan: Yeah. One of the things that I thought of before this conversation is that we and a lot of listeners of this show aren’t in a position to not have premium developers working for you. The market is a bloodbath right now for technology people, it’s competitive, but you got to find some way to step up and get quality people in because we really missed out on a lot of quality development this year by pitter-pattering around with some junior folks.

Another big argument for TinySeed funding is to just be able to enter the market with confidence and not to lose 6 or 12 critical months. 

Ian and I are going back to the marketplace on Monday to hire our third developer, and we’re not screwing around. I don’t sit in Golang every day or I don’t understand what Tailwind is, the nuts and bolts, so I want to hedge my bets because I want to be a responsible entrepreneur. 

I think one of the lessons I learned this year is there are places where it’s worth cutting corners, and your development resources in a startup aren’t really one of them. I know that sounds obvious, but it’s harder to say I’m going to write this check and then you’re on the line to go and create the revenue that will support it responsibly.

Ian: I’ll give you an example of how we really screwed that up in the last year. Dan had a great idea which is essentially a services marketplace. If you look at remote work and the future of work in general, there’s a lot of services overlap, meaning, essentially, employees will be replaced by services at some point because there’s a lot of efficiency in that. We’re already starting to see this happen. We have clients come to us and they’re like, hey, I’m thinking about hiring a senior marketer. I’m thinking about hiring this firm. That’s a decision that people are making these days. We’ve seen and done this in our own businesses. 

We launched the services marketplace on the side of DJ because it’s like, hey, I’m trying to solve a problem here. Maybe we need a person, a service, a consultant, or a freelancer, but it’s all the same thing. It essentially didn’t work big time, but when you look at the amount of development resources that went into that project, it was easily six months. 

It’s something that we just wiped off our screen the other day. The buttons are completely gone. Sad to say, it wasn’t a good idea, but certainly, the timing wasn’t good, we didn’t have enough resources to market it properly, and people don’t really understand it. There are a lot of reasons why it didn’t work in the context of DJ, but in terms of our resources, it put us behind in making that decision. 

That’s going to happen to us a couple of other times, but trying to figure out how to properly deploy our factories so they’re making the right things that are pushing us forward is really difficult. It’s also really powerful. 

Dan and I can sit here as non-technical people and order the team around to be like, hey, wouldn’t it be cool if we had a services marketplace? Everybody’s like, yeah, it would be great. It’s like, well, now we’re back 12 months.

Dan: Good idea, boss, who doesn’t know anything about this.

Rob: It’s tough to know what’s going to work. I think it’s Tim Cook, CEO of Apple, who says, there will always be many more good ideas than we can possibly implement and we just have to figure out which one or two we focus on. That’s the trick of all businesses probably but software especially because if you don’t focus, then you do that. You wind up building entire features that no one uses and you lose months of time. It’s especially challenging when you’re writing code.

Dan: And you got to babysit those features once you build them. They don’t just hang out. You got to constantly be improving and fixing bugs. We’ve been really focused on this concept of pushing deeper. Why doesn’t everybody just have this […] grin the entire time they’re using our job board? 

These are the sorts of concepts that we’re focusing on right now to find opportunities in the details as opposed to I think Jordan Gall calls it CEO bombing. You just come into a meeting and you’re like, hey, I had a dream last night, everybody. Job board is the future of work. It’s like, how about the future that a button doesn’t work on the other browser? Let’s talk about that.

Rob: Yeah, totally hear you. You guys have a couple of frameworks that I think are really interesting. One is the thousand-day principle. Dan, do you want to define that briefly? My question is, where is Dynamite Jobs on that journey? Where are the two of you on that journey with Dynamite Jobs?

Dan: The thousand-day principle, I first heard of it from a mentor of mine named David McKeegan who runs a wonderful business, which is also a for-the-rest-of-us business. It’s tax consulting for digital nomads.

Rob: Greenback Tax Services?

Dan: Yeah. This was in 2012. I was in my 20s. I was like, why isn’t everybody here? We were hanging out at some villa in Bali and I’m like, they read the blog post. Why aren’t more people joining this entrepreneurial revolution? It seems like this amazing opportunity.

He said, I think the thing that people aren’t willing to traverse or understand is that they’ll have to make less than they would make at their professional careers for three years or about 1000 days. I think most people can’t get through the 1000 days, and that’s why they won’t join.

I just thought it was clever, interesting, and sticky, so I started just asking what normally happens in the first year? What normally happens in the second year? In the third year, you have this feeling where you’re like, now I can hire people to run the business for me and I make as much as I made previously in my professional career. 

I’ve just seen this pattern happen time and time again since that time that cultural context has changed, but the basic process of suffering for three years in order to get your vision out into the world is a decent rule of thumb or at least a decent way to set expectations for what the journey might look like.

Rob: Yeah. That’s a line I often say, think in terms of years, not months, especially if you’re bootstrapping because people read TechCrunch. It’s like, it raised millions and they have millions of users. It’s like, it just doesn’t happen that way.

Dan: For me, this idea of emotionally plowing through plateaus is really frustrating. When we came back to Dynamite Jobs, I had a little bit of rose-colored glasses because we had already had a “successful business,” and then feeling that pain again of, okay, we’re back here. It’s the 14th Wednesday in a row that our revenue is the same, we made a bunch of mistakes, and it just feels like there are all these problems. 

That’s a lot of what growing a business is. It’s not always positive feedback every day. You’re hanging out at plateaus until you break through to the next level. It’s been interesting to have to eat some humble pie, come back, and go through the process again. We’re not immune to these struggles, challenges, and doubts of sustaining yourself for months and years at a time when things aren’t always up and to the right.

Rob: You guys have built so many assets that you can lean on. You’ve built the audience, you’ve built the community, and you built a stream of revenue to be able to basically fund yourself. As long as you’re motivated and interested, you have an infinite runway effectively. That’s something that you’ve earned through 13 years of podcasting and community building.

Ian: That’s the other thing about the thousand-day principle, not only have you replaced your income from a job at the end of those three years hopefully, but now you have an asset. 

We’re just starting to be at the point where we’ve reached our 1000 days with Dynamite Jobs. The first year or two though, Dan and I were just throwing a bunch of cash at it. We weren’t paying much attention to it, meaning, we were doing the CEO bomb. We have all these good ideas and we had some cash to deploy, but we didn’t really have our finger on the pulse. It’s been about 1 ½ years of our full-time concentrated effort on this.

Rob: In 2019, Dan, you mentioned that you think you had about $5000 in revenue and you’ve been public about this, but in 2021, you had $500,000 in revenue, and in 2020, some number in between that. Do you remember what it was?

Dan: I think it was something between $50,000 and $80,000.

Rob: That’s a huge jump. That’s almost 10X from 2020 to 2021. What do you ascribe that to? 

Ian: There are a couple of things. Number one is Dan and I started putting our full-time effort into it. I think that there was a big change when that started to happen.

Dan: Let me just underline what that is because a lot of it is emotional bravery. Like you said, Rob, we didn’t need to do this. We were trying to get real with ourselves about what we want our careers to look like over the next five years, what goals we want to take on, and why we are going to sit in front of our desks and go through the pain of having difficult client interactions and of looking at competitors who are outperforming us. 

There are all these emotional difficulties of doing this work. For Ian and I, we had to have a rock-solid communal goal of why we were going to do it. That’s how I’m interpreting that point of getting our fingers on the pulse. It’s a lot easier just to put something on the Internet, have some Wi-Fi money coming your way, and just ride your bike or something.

Ian: Another way to say it is we had to engineer our backs being up against the wall, which is a unique position to be in. When we first started our business way back in 2007 or 2008, our backs were literally up against the wall. We had no choice. This time, it’s like we had to throw ourselves to the wolves when we weren’t necessarily in a position where we had to do that, per se, but we wanted to do it.

Dan: One of the critical next steps was stepping up, genuinely hiring people, and recruiting people who were better than us. For example, our CTO, we had this friendship happening over the years. We watched each other’s projects and supported each other. We were Internet friends, but I wasn’t confident enough to say you should change your life to come work with us. That was a problem because I didn’t have a vision. 

Ian and I weren’t on the same page. We didn’t decide what that was. The moment we decided that, hey, we’re going to go for this, and here’s how we’re going to go for it, we were able to recruit a CTO. We were clear about the vision. We were able to recruit a senior recruiter, both of whom have skill sets that are far beyond Ian and myself. That was a watershed moment. Now, all of a sudden, we can sell $6000 products. I can’t evaluate candidates to a $6000 level. Our senior recruiter has been doing it for 15 years.

Rob: It sounds like you committed to the business at a certain point in 2020 where you’re like, oh, this is what we’re going to do and went all-in. I know you still have all this other stuff going on, but you went all-in on it and that gave you the confidence to bring on people at that level. Is that right?

Ian: Yeah. I’d say it was the confidence of going all-in, but then once we started hiring professionals—and I don’t think we’ll ever go back from this now—and people that are truly better than you, it really changes the scope of what’s possible. 

Even in our product manufacturing business that we sold in 2015, everybody was pretty good at what they did, but no one came into that business on fire and the best in the business kind of thing. I feel like we’re starting to cultivate that over at Dynamite Jobs. It’s certainly inspiring for me to come to work every day and watch people perform on a stage that they’re professionals at.

Certainly, it’s expensive. That’s one thing to notice. If you’re going to build that kind of organization, it’s not cheap, but the things that we’re going to be able to achieve with these A-players are going to be pretty cool.

Rob: What’s interesting once you get on this side of it—because I’m there as well and I’m going to give a couple of examples of how I made the same mistakes of hiring junior people and really wasting time and/or energy—you’re like, my early hires are all going to be senior people. They’re all going to be better than I am at their particular job. Suddenly, the case for raising funding makes a lot more sense. 

I know when I was bootstrapping and I hear people say, I’m bootstrapped and that’s all I do, that’s great, but you don’t have money to hire senior people. 

In the early days of Drip, obviously, Derrick Reimer, you guys have seen him do Drip and then SavvyCal. When I met him, he was 23 years old, but he had the chops of a super senior person. But everyone else we hired were these people out of code school and out of three-month code academies because I didn’t have the money to hire them. It worked out, but it took us way longer and there was a lot more headache to get there. 

The moment that we got acquired and had all this venture funding to spend, it was game-changing for us. That was another moment where I said, I’m not going back, much like you guys have decided. You’ve seen the other side of it.

Now, we hired Tracy to run TinySeed America. She’s a type-A who keeps these trains running on time. She’s a way better integrator than Einar or I. 

Xander runs events better than I ever could. We used to run them and they were successful, and then Xander started helping us in 2014. I was like, wait a minute, this guy is really good. This is a hard-learned lesson because I’m cheap. I think we’re all cheap.

Ian: I don’t think you’re necessarily cheap, but part of the bootstrappers’ curse is being resourceful and clever. You get in this clever pattern and then you don’t realize what you’re missing out on because we’re all super clever to get our businesses to this point. Then now it’s like, well, am I going to keep being clever and maybe cheap, or am I going to actually go for it?

Dan: I’ll be transparent. Earlier in the year, we did this clever thing, which I think was a mistake, where we hired multiple developers that were junior and basically pitted them against each other. We were transparent about that element, but the thing about those salary levels, Rob, is you’re already at 60%–70% of what the premier would cost. 

We ended up spending more money and wasting more time in the long run than if we just went out and got somebody senior. I’m really passionate about these pivotal lever moments. As an entrepreneur, it’s like, okay, you were clever about cutting costs. What about being clever about your business model? Why can’t you pay top-of-industry? Maybe there’s some thinking to be done on the upside and the margin side. 

That’s something that Ian and I have really been exploring intellectually over the past few months as we really focus on this new developer we want to hire. We want someone this premium that loves autonomy, sits on top of our candidate side of the marketplace, and just digs into these problems on a daily basis. That’s different than saying, here’s how much we think we can afford. It’s scary, too, because now we have to go out and find a way to pay for it. 

I agree that we talk a lot about control. If you raise a little bit of money, now, all of a sudden, you’re not 100% in control, but that also means that your business can morph outside of your immediate skillset and ability to come to work every day. I’m all in favor of opening up the floodgates a little bit and getting better people involved earlier. It’s almost like a self-respect thing, too. If your time’s worth it, you should be dealing with your peers and people that you look up to.

Rob: The two of you run a job board and a recruiting agency. When you go to recruit, you’re going to hire a developer starting tomorrow or next week. What is it that you have learned that you do differently than someone who doesn’t know what they’re doing? How do you find great people? What is your pull into that from your learnings?

Ian: We’ve learned a lot. Hopefully, we’re good at what we do when we go to hire a developer, and I think we are. 

There are a couple of things that are going on right now. One thing that’s going on right now is a candidate’s paradise essentially. All these candidates have multiple offers on the table at any given time which is a unique point in history. It’s not generally the case, but right now it is. All these companies are going remote. The companies that have been remote are frustrated, I think.

Rob: That used to be our advantage, right?

Ian: Yeah, exactly. Now, you look at Latin America, Asia, and all these different places. They’re coming up as well because now, everything’s flattening and there’s becoming a lot more transparency around the marketplace, salaries, and whatnot. It’s like, hey, I’m a developer in Latin America. Shouldn’t I make just as much as a developer in the United States? I have the same skill set. Here’s my portfolio.

The costs are going up for everybody. Those are some of the unique things that are happening in the landscape today.

Another thing that is happening that we should point out is you can’t just post a job in most cases on any given job board and find your candidate. Essentially, what we do over at Dynamite Jobs is we post at Dynamite Jobs, and then we post in a lot of other places on the Internet where we think that these people are hanging out because it’s very fragmented. It’s good. 

Not everybody back in the day go into monster.com and find their perfect candidate in five days. It’s hard. You got to dig around and find these people, especially these candidates that are A-players. They’re not necessarily hanging out on job boards. 

What does that mean? Maybe that means a cold approach. Maybe that means finding them in these weird places, seeking them out, and then trying to figure out what their motivations are. This is where an A-player recruiter comes in to have conversations with candidates in terms of their motivations, like what’s going on at your job right now, are you happy with your income, what moves are you trying to make, and try to suss out basically where these candidates are and where they want to be. 

There’s actually a thread on Hacker News the other day about why you should always talk to a recruiter. There are a lot of reasons why you should. They can be your advocate as a candidate, they can help you make moves, and they can let you know what’s going on in the marketplace in terms of salaries. They work both sides of the aisle which is, in a lot of ways, good.

Dan: But most recruiters suck which is why that article went to the top of Hacker News. The way I’m thinking about this is because the world’s completely fragmented now, you need to tell a founder-level story to candidates. With geographic constriction or before the pandemic, you could be like, we are this kind of agency. We pay this much. We’re in this city. This is a job, apply. 

There’s a lot of implicit narrative there that candidates can buy into. Probably the lowest cost, highest leverage action for founders is telling that founder-level story in your job post and to the candidates. Candidates can know right away if they’re an A-player and they’re talking to a B-level recruiter that doesn’t understand their situation. That’s a huge turnoff. That’s basically what we’re trying to emulate. 

We talked to Greg on the phone. He understands our client stories at the founder level. He understands why they started the business, what kind of opportunity it is, and what direction it’s going. He can communicate that up here to A-players. 

Most recruiters are just playing the numbers game essentially. That narrative of what you’re doing as a business is in our DNA. That’s how we’ve always hired, we’ve told the story of what our business is doing. I think it’s expensive to do and is why 90% of our job posts don’t have a compelling company narrative.

Rob: Yeah. There’s advice that I always give to founders, and it’s that you’re not a big company. Don’t write a job description that acts like a big company. Don’t go read the Target, Best Buy, and General Mills job descriptions because they don’t have the same things to offer. What they have is their salaries are probably higher and they have more benefits, but we used to call it combat pay because you have to put up with all the […] at those companies. You’re kind of in combat, so you make more, but you hate your job versus if you’re a 5-person company or a 10-person company, what do you actually have to offer? What is your advantage? How can you use that against a larger company?

Usually, the way I’ve done it is to almost think of the job description a little bit like the sales letter, not go over-the-top Dan Kennedy style but to be unique.

Dan: You’d be better off to do Dan Kennedy style honestly. Be careful who you copy because there’s this big implicit story in a job post for Best Buy. You don’t need to write it. Everybody sees a Best Buy job post and they can tell their own story. 

I look at our site and I see these brands that I’ve never heard of before. There are 15 employees and it’s a genuine life-changing opportunity, but the founder’s not taking the time to describe that. I understand why. It takes a lot of energy, but I feel like that’s the number one piece of advice right there.

Rob: Last question for you guys today as we wrap up. Another framework that you’ve called out a lot is Rip, Pivot, and Jam. It’s where you see an idea, you rip it which just means you take it, you pivot so you change it, and then you jam on it. You basically execute on it. 

Whether it’s the job board side or the recruiting side, did you actively rip, pivot, and jam because I can see some ripping, pivoting, and jamming happening? It’s like you had the traditional recruiter model and you took it, tweaked it to make it flat-fee (it’s less expensive), and you focused on startups and digital nomads type of folks. People are building businesses but not big companies. I can see it on the job board side as well. What’s your take on that?

Dan: The fundamental idea of Rip, Pivot, Jam was how can you not be so intellectually challenged to get started in business? It sounds very intimidating to me to come up with a business idea and you realize that you’re surrounded by 10,000 business ideas every day. 

In other words, you could say, well, scratch your own itch, find a problem, or whatever, but how about just look at the business? That business is working. Go and talk to the people who run it and make sure it works. This recruiting business is a $1 billion industry and it works. 

The pivot part is why don’t people do that for this or this for that? That’s just the basic pivot. There are a bunch of different ways you can formulate a pivot. In our case, it was simply like, this service is valuable, it’s profitable, and it has a track record in the world, but there’s none of it for our people, and our people need it too. That was simply it. 

Then, the jam part is the thousand days. It’s not going to work on month number one. We had some momentum early but then you got to hire people. You got to backflow that revenue stream. You got to hire a boat line and you got to keep plowing to those plateaus. That’s the jam portion.

Ian: When I look back at our business success and failures, most of our failures were what we thought were the best ideas. It’s like, here’s a brand-new idea that’s never existed before. Let’s put this into the marketplace. Thud, it doesn’t work. 

The ones that do work are like, hey, this has been around forever. Why don’t we just change this a little bit? 

Rob, there’s a lot of that going on in DJ. These things have existed. Job boards have existed forever. Recruiting has existed forever. Now, it’s like, how are we going to pivot this? How are we going to make it 5% better this year or this month, repackage it, and present it?

Dan: Yeah. There are a bunch of different methodologies that come across in Startups For The Rest of Us where you can find that pivot. 

We’re certainly not fans of copying anybody’s work. Originality is important, but you don’t need to be original about the conception of how to make money online. That’s been proven out. 

The question for founders to determine is what’s the thing that you can do differently that other people aren’t willing to or technically able to do? In our case, we were willing to cash flow essentially a recruiting service for the price of a job board. There’s no job board in the world who’s dumb enough to do that, but we were like, we’ll do it for two years because we can afford to and we were in a unique position to have a perspective on these cool jobs that our members had that no other job boards had access to. 

We were able to build these relationships. That was our pivot. It’s like, okay, there are job boards, but there’s nobody willing to do this. If you come to Dynamite Jobs, a person talks to you about your role and figures out what’s best for you. That’s a necessity because other job boards are established and they sell based on trust. We had to earn that trust in a different way. That was our perspective in pivot, and it got us to where we are now. Hopefully, we keep going.

Rob: You almost 10X last year and I hope to see a 10X this year. If folks want to keep up with you guys, you are @anythingian on Twitter, @tropicalmba as well on Twitter, and of course, Dynamite Jobs if folks want to check out what you’re working on. Thank you so much for coming by, guys.

Dan: We appreciate it, Rob.

Ian: Thanks for having us.

Rob: Thanks to Dan and Ian for showing up. I could talk for hours and actually, I do talk for hours with those guys whenever we get together. Last time I was in Austin for MicroConf Local in September, I had dinner with them and had such a great time with awesome conversation. I hope to have them back on the show again soon. 

Thank you for listening every week. If you haven’t subscribed, do that. If we’re not connected on Twitter, look me up @robwalling. I look forward to being back in your ears again next Tuesday morning.