Business Bites Epi 88: Transitioning a Side Project into Full-time Entrepreneurship

Transitioning a Side Project into Full-time Entrepreneurship

Episode 88 on the Business Bites Podcast

The Gist Of This Episode: Leaving your full-time job to pursue your own entrepreneurial journey can be pretty scary and overwhelming, but there are things you can do while still working at your job to make that transition a lot easier.  Join Rachel as she and Tommy Griffith discuss turning your side project into a full-time business.


What you will learn: 

  • How failures can actually be a good thing
  • How to feel free to keep trying if something doesn’t go as planned
  • What you need to consider when deciding on a side project
  • Why recognizing your shortcomings can help you be more successful
  • and more!

Expand To Read Episode Transcripts

Rachel Brenke: Hey, you, part-time entrepreneur. This episode is just for you. There’s a lot of good information for those that are full-time, but I specifically targeted in on this because this has been a top question in the Business Bites Facebook group, and coming to the inbox. Make sure you guys are in the community, and on the Facebook, and the Facebook group Business Bites, so we can continue the discussion. But until then, this episode is just for you all.

Speaker 2: Welcome to the Business Bites Podcast, the podcast for busy entrepreneurs. Whether you’re an online entrepreneur, or seeking after brick and mortar success, this podcast brings you quick bites of content, so you can learn and grow anywhere you are. Now here’s your host, Rachel Brenke.

Rachel Brenke: Hey, guys. Welcome to Episode 88 of the Business Bites Podcast. I am your host, Rachel Brenke, and I am joined with Tommy Griffith of He has been doing search engine optimization for over 10 years. He’s managed SEO, from big corporate giants like PayPal, Airbnb, and now runs Clickminded. This is a digital marketing training platform for marketers and entrepreneurs. I think many of you are going to enjoy that. What we are going to talk about most is that he started Clickminded as a side project while working full-time at Airbnb. He grew it until it started generating more revenue than his annual salary. You guys are probably hearing either the similar song that you sang, or what you’re trying to do in your current business. He has been two years out on his own, quit Airbnb to go full-time. He’s ran into problems, struggles, successes, and he wants to share all of this with you guys to help you to get from a side project into a full-time business.

I’m going to link all of this at Episode 88, so, to snag the notes, links, and the direct information of all the greatness that Tommy has to provide, but let’s get started with the episode, so Tommy, welcome.

Tommy Griffith: Rachel. Thanks so much for having me. Really appreciate it.

Rachel Brenke: Yeah. I’m excited to have you on. We have only talked briefly, but I have really been encouraged by your story, because I kind of took incremental steps in my own entrepreneurship journey. I told them about, obviously, Clickminded, and how you went from side project to now full-time, but do you want to give them a little bit more context of what that path really looked like for you, and then we can dig into the actionable steps.

Tommy Griffith: Yeah. Sure, so my whole story kind of started, like a lot of internet entrepreneurs these days, by reading The Four Hour Work week. Are you familiar with that book?

Rachel Brenke: Oh, yeah. I love that one. I wish I could only work four hours a week.

Tommy Griffith: Ah, yeah. For sure. I think that book is incredible, but I think the big, dirty secret is that no one, no one who’s touched that book has ever worked four hours a week, for sure.

Rachel Brenke: It does sound good. You keep aspiring to do it.

Tommy Griffith: For sure. It’s a very click bait-y title, but yeah, for any of your listeners that, the uninitiated that haven’t heard of it, it’s kind of dated now, but the general concepts were pretty strong, but it kickstarted a lot of people off onto creating remote businesses, remote ideas, remote teams, and a lot of internet entrepreneurs kind of started by reading that book. I got really into search engine optimization 10 years ago after reading that book. It inspired me to create my first product. It was a very dorky e-book that I wrote, back in 2008, and I basically said, “Okay, how, you know, how do I get this to the top of Google in order to make it all work, right?” Started that way, and my first business idea, I started a company with a friend of mine that failed miserably. We were traveling, and starting this business related to internet marketing, and it just absolutely failed.

I was one of these guys who was very blessed, and I graduated university with no debt. My parents paid for college, and I put myself into debt after university trying to start this business with a friend of mine. It ended up being really, really hard, huge bruise to the ego, came home with my tail between my legs. It was very much like, hey, Mom. Hey, Dad.

Rachel Brenke: I can totally imagine you licking your wounds, so.

Tommy Griffith: Yeah. For sure. Definitely did the knock on the door, and asked if my parents remembered me, and if there was room on the couch kind of thing, so it was

Rachel Brenke: They said yes, right?

Tommy Griffith: They said yes. They reluctantly let me back into the basement, but yeah, so that failed. Went into a lot of debt. It definitely sucked, but it was in this position where I had suddenly learned search engine optimization for about a year and a half or two years, and it ended up being right place, right time with PayPal. PayPal was hiring a search engine optimization manager for emerging markets, and that kickstarted the next sort of phase in my career. I spent two years managing search engine optimization at PayPal, and four years managing search engine optimization at Airbnb. The side project kind of came into that moment when I got back on my feet, and got the job, and moved out to the Bay Area, California. I’d had all this debt from the original company, and was trying to pay it off, and Clickminded was probably idea number 15. I tried a lot of different things, kept at it.

It started as an in-person search engine optimization training course, so teaching startups on the weekends, physically in-person, sort of how to do SEO, right, how to get their site ranking higher in Google, and generating more traffic. That initial idea, even though I loved it, I love teaching, and I love SEO, the initial business idea was terrible. It was just, couldn’t scale. It was very, very kind of expensive to run. It took a lot of hours, but I ended up being the right place, right time with this kind of online course, online learning renaissance that we’re in right now. I took this physical in-person class I taught a long time ago, put it online, on Udemy, which is an online course marketplace that was really starting to blow up in 2012, and it took off from there. I worked on it as a side project while working at PayPal and Airbnb, and about three years in, it grew to more revenue than my salary, and about two years ago, I left to go full-time on it.

Rachel Brenke: I love that you talk about the failures and how you had multiple failed businesses. Not that I champion that you had those, but you’re in good company. Look at companies like WD40, the lubricant. The 40 is because that was like the fortieth formulation that finally succeeded for them.

Tommy Griffith: Really. I didn’t know that.

Rachel Brenke: Yeah, so actually, I have been reading… Oh, I’m going to butcher the name of the book, but I’ll put it in the show notes for you guys. Company of One, I believe, and it talks about these ideas, and failed ideas, and somebody else who everyone knows about, Walt Disney. Mickey Mouse was not his first cartoon, and his first creation, so you’re in good company of people that have come before you, and I just wanted to pinpoint that, not to make you feel bad, but because I think many of us, and I’m still like this, and I’ve been doing this for well over a decade now, when something flops, and you’re so excited about it, it’s really hard to not get super deflated, and then you’re like, well, it was a side project anyway, so whatever. Then you just kind of give up, and I see so many people then go back into like corporate America, or stay in corporate America, and they remain unhappy.

I love that you’ve overcome, and continued to push in order to move into a full-time thing. What is something, though, before we move into that transition, what is something you would tell yourself when you were in that first business failure? What would you say? Obviously you can’t say, “Hey, by the way, you’re going to succeed,” but maybe some encouragement when you’re in that moment.

Tommy Griffith: Right. Yeah. That’s a good way to think about it, and actually, Rachel, I’m curious with you, I know your business has gone down a lot of different paths, and you have a lot of different products, and a lot of different angles, but was… Were there a bunch of different iterations to get to where you are now? Did you take a lot of side paths and side routes, and things like that as well?

Rachel Brenke: Yeah, so I’ve had multiple brands. I do have a brand that I, two specific brands that I actually killed off on my own, and then of course, I’ve had failures within those brands. I’ll go and hard charge, and create a course, or a product, and I’m like, the audience has to have this. They’re going to buy it, and then it’s like, crickets. I’m like, what did I do wrong here? My subject matter is a little different, I think, than most, because I’m also meeting people kind of halfway, a little over halfway, because I present a lot of, they don’t know what they don’t know, and that’s what this podcast is for, so sometimes because of that, I’m able to justify to myself, oh, that’s why it’s not failing, because they just don’t get it. You just need to fine tune your messaging, and often times, it’s not even that. For example, I had Blog Legally, and my goal, if you’ve looked at my different brands, they’re all very legal-specific to a different niche.

I was like, I’m going to go onto the blogging industry, because I’m blogging. I’m a blogger, and, but it was super saturated, and it just did not really take off in the way that I expected it to, and so I killed it. I killed it, and moved it into, and wrapped it into this podcast, which ended up launching number six on iTunes, right? For me, it was a failure with a good ending story for that one. In the alternative, I had a membership-based course that was very similar for bloggers, and I was like, oh, I’m going to be able to do this. I know enough people, and it completely failed. I could hardly get enough members in the door to sustain it, and so I just killed it off, and that doesn’t have a good story on the other side, because I haven’t revived it anywhere else. Those members just went on their way, and yeah.

I don’t know. When I, I guess, to answer my own question, like I said to you, when you’re failing in something, what would you want to say to the person or to yourself, then, when they’re in the midst of the failure, and I don’t know. For me, though, I don’t really let failure bring me down in a way. It almost pushes me further to really find a way in, when looking for that glimmer of light in a different area, reaching in the darkness, so, yeah, [crosstalk 00:10:57] too, and I’m glad you asked me that. I try to be as transparent on this podcast as possible.

Tommy Griffith: Yeah, and that’s really interesting, and it’s funny, too, because I think the big, dirty secret about a lot of this stuff is, when… We have this vision, first of all, that our own story is way more important than everyone else’s, right? That’s the first thing, and then the second thing, though, is that it… Whether you succeed or whether you fail, it’s always going to be spectacular, right? You’re either going to be a massive success, and go public, or get bought by Google, or whatever, right, or when you have a failure, it’s going to be like a devastating, catastrophic, comet hitting the earth kind of failure, and everyone’s going to be weeping for you, right? The reality is, things die with a whimper. Things quietly sort of disappear, and it can be really depressing. That was just… I think it was a funny, a really interesting moment for me.

I’d spent a year and a half working on this initial business, when I was 22 years old, with a buddy of mine, and when we finally ran out of money, and finally… I finally decided to hang it up. I was flying home, and I had, was building up this story in my head of what I was going to tell my friends, right? It was so important to me, kind of that the narrative I had to my friends, or what people thought. I was young. I had just failed. I was really embarrassed by it, and sort of the whole story that I had, and the explanation for why I was failing was really important to me. I remember that plane ride back home was so brutal, and I was just replaying what I was going to say in my head over, and over, and over again. When I finally got to see my friends, and family, and hanging out with them, one of my friends inevitably asked, “So what happened? What happened over there?”

I started telling the story, and it’s like a year and a half long, and how do you tell a year and a half long story in a little bit, right? I started telling the story, and within 20 seconds, one of my other buddies spoke over me, and was talking to someone else in the room, and said, “Hey, what was the score of the Red Sox game last night?” Then the conversation just changed, right, and no one brought it up again. It’s really interesting, because at first, I was super mad. I was like, oh, my god. Why don’t they care? This is the greatest story of all time, right? What I realized later on is that I was actually so grateful for this, because it made me realize that, and I hate to say this. This is going to sound a little brutal to a lot of listeners, but nobody cares about you.

Rachel Brenke: Yeah. You’re inconsequential, really.

Tommy Griffith: Right, and I mean that in the most empowering way possible. It’s like, no. Everyone’s so obsessed with themself, and naval gazing, and looking, and staring themselves in the mirror for so long that the reality is that this can be the most freeing sort of realization you could ever have. Nobody cares, and it sort of frees you to do what you want to do, and work what you want to work on, and fail as many times as you want because the reality is, people are thinking about going to the grocery store, or getting their kids to school, or whatever it is. It’s just like, they don’t actually care about your struggle, so it was one of these weird moments in time where yeah, I thought it was going to be this big, grandiose failure, and everyone would be talking about it, and the reality is, I didn’t even get past what was the score of the Red Sox game. You know what I mean, so.

Rachel Brenke: [inaudible 00:14:36] Red Sox. That’s pretty bad. No. Just kidding. Just kidding. Yeah. No, and I’m glad that you bring that up, because I… There’s like a, like you said, freedom, and there’s a freeing feeling of freedom to fail. You always hear about failing Ford, and all the other cliches, but the reality is no one actually wants to step up and say, “Hey, I actually failed,” or actually look like I had to look at a brand and go, this is costing me money. Why am I doing this? Just cause I think the idea is good doesn’t mean it truly is, and actually, I think sometimes, those kind of doubts keep people from turning a side hustle into full-time. When you built this side hustle… I guess I shouldn’t use the word hustle. I apologize, but there’s all sorts of opinions about that word, but this side project, how convinced were you that it was going to work, or did it just quote unquote “happen?”

Because it didn’t just happen. There’s elbow grease that goes into it, but what did it look like?

Tommy Griffith: Yeah, so I think, and I have a lot of strong opinions on this one, so like I said earlier, Clickminded was probably like idea number 15, and a lot of the motivation initially was, get out of this big pile of debt I had created for myself. One piece of feedback that I have for anyone that’s listening that’s thinking about this, I remember, okay, so here was a fun example. I had this one idea before that, and it was an iPhone app development, lead generation site, right? The idea is like, okay, it was 2011. The iPhone was obviously hitting peak adoption. People were still picking them up. If you were a company that didn’t have an iOS app yet, you wanted one. A lot of people were getting interested in iPhone app development. They wanted to create them, and so the idea was like, okay, I’m going to make a site that’s ranking on Google for iPhone app development cost, and iPhone app developers San Francisco, and things like that, and sort of capture all those leads, and then maybe sell the leads, right?

That was the product idea. I got the site up. I got it running. I got it ranking. It started to work. I started generating leads, and every weekend, when I went to wake up on Saturday morning to go work on it, I just hated it. I had no interest in the topic. I was just bored by it, and even though it was working, I was so miserable running it, right, and so shut it down. One piece of advice I would have is, a lot of people… There’s this cliché. There’s this trope in Silicon Valley around markets. I think it’s venture capitalists. I think it was Marc Andreessen or someone like that, he said like, “I’d rather have a good market, a mediocre product, and a mediocre team in a good market than a great product and a great team in a mediocre market.” I understand where they’re coming from, and when you’re talking about billions of dollars in venture capital money and things like that.

If you’re starting a side project, and your first goal is that first thousand, or first 10,000, or first $100,000, the single biggest asset you have is your own personal interest in this thing, right? You are the engine that’s going to drag this thing across whatever finish line you’ve determined for yourself. I don’t subscribe to that great market sort of mentality, because if you take that to its natural conclusion, the best markets are like oil, and like space exploration. You know what I mean?

Rachel Brenke: Right. Right.

Tommy Griffith: It just doesn’t make a ton of sense when you are the engine that’s going to get this thing off the ground, and so I was in this position where I loved search engine optimization. It feels like a video game to me. I really like it, and I also love teaching, and Clickminded was this thing I just really enjoyed doing, even though the business didn’t initially make sense at first, so I highly recommend if you’re thinking about this, to really focus on where you have unfair advantages, and where… There’s another sort of trope going around that I really like a lot, though, where it’s… What you’re working on every day should look like work to other people, but feel like play to you. Right? You just can’t… It’s really hard to lose that way over the long term if you’re working eight, 12, 16 hours a day, if other people are working eight, 12, 16 hours a day while you’re playing eight, 12, 16 hours a day, you’re just going to win over the long term, and that’s what ended up happening with me.

Rachel Brenke: You know what’s funny is, because, and I… There’s some listeners that are probably in similar fields to me, where there’s this old school mentality of how you have to do things, right? I’m supposed to be wearing a suit and sitting in an office, and I’m not supposed to be wearing a nose ring and ripped jeans to the office. I’m not supposed to be sitting on a beach somewhere recording a podcast. I’m not right now. Wish I was, but because I hear this a lot from other attorneys, who will always… My point, what I’m getting to, is it looks like play to them, because they always say things like, “Oh, can we send you clients,” or, “Oh, how’s business?” I’m like, homie. Business is really good. I have a wait list. Can I send some to you, your way? Because it looks like play to them, but mine also started as a side project. It actually was a solution for, to give me back more time.

People were asking questions all the time, and then the blogging, and the consulting, all that, just really helped to monetize my time, and then give me back time, and make it efficient to distribute content. For me, the defining was it quote unquote “just happened,” right? For me to make the decision to go from side project to full-time, I knew I wanted to do that eventually, and it sounds like you, obviously, with having the failed businesses before, always had the idea of wanting to go into business. For me, though, it really just… I hate to say it just happened, but it was like… It wasn’t like I said, “Oh, I’m going to quit my full-time corporate job this date. I’m going to have this much money in the bank.” I was a little logical. I had some of that, but it wasn’t like a drop dead day. Finally, one day, I woke up, and I went, whoa. I’ve replaced my income and then some. I can quit. I can walk away.

Tommy Griffith: Right. Wow. Yeah, that’s pretty awesome, and it’s a similar story as well. I’m curious with you, Rachel, because okay, you are… Yes, I would definitely view you as not a typical attorney, or legal consultant.

Rachel Brenke: Good. Thank you. That’s what I’m going for.

Tommy Griffith: You have ripped jeans, and nose ring, and all, but the other thing that, too, is interesting to take kind of what I just said, and overlay it on your situation, I really like this idea of unfair advantages, and finding things where you just feel more natural, and yeah. I got to admit, most attorneys I know aren’t podcasting, and aren’t creating a lot of really good media, and video content, and that stuff… You seem like a natural at it, and I don’t know if you enjoy it, but you… Seems like you do, and that seems like you sort of found your unfair advantage. You know what I mean?

Rachel Brenke: Mm-hmm (affirmative), and I think that’s really good for the listeners because if you look around, for me exactly, and I hate to keep talking about myself, because I brought you on for this, but I’m not really… I’m not sharing anything novel. I don’t make the laws. I’m not sharing any content that you necessarily can’t find elsewhere. It’s the way that I’m doing it, and that’s what allowed me to turn a side project into full-time, was because there was a demand to consume in a certain way, and lawyers aren’t hacking it. They’re just not. They’re old school. You got to come sit in my office. I’ll wear a tie. We’ll meet for an hour. Then you go on your merry way, and if you don’t call, you’re going to die. [crosstalk 00:22:35] … Towards my profession whatsoever. Let me ask you, out of all of this, what was the hardest lesson you learned about it being a side project? During that time, what was the hardest thing for you?

Tommy Griffith: Yeah. I think the most brutal sort of revelation came a little bit later, when I was figuring out when to leave, and I… Same as you, I left. I didn’t have a hard, did the Excel math, and had a drop dead date of when I was going to leave. I was in a weird situation where I was working in an awesome company. I was very blessed to have gotten into Airbnb at a crazy time. None of my friends had ever heard of it when I joined, and everyone had heard of it by the time I left. There was 100 something people when I joined, and 2,000-something people when I left. My first week there, the State of New York subpoenaed Airbnb for their data, and then the last week I was there, the last week I was there, we worked on a Superbowl commercial, and Beyonce stayed in one, right? It was just like a wild sort of time to be there, so I didn’t leave right away. I had passed my income on the side project for a while, and I continued to work there.

Still wanted to stay there. Had personal stuff. I loved all my friends, and was dating someone, and so I just wasn’t… It wasn’t like a hard date where I needed to eject, but what I did, I was pretty over the city of San Francisco. I was a little sick of San Francisco, and so I was getting ready to leave, and I was eventually starting to plan my escape. One massive thing I did, one massive problem I made, I had, was I planned too much, and this might seem counterintuitive, but I gave myself way too long of a runway to figure out the next steps, and what that ended up doing was it set my expectations absurdly high for the next phase of my life. I was really excited to get out of San Francisco, do this digital nomad thing, where people are building businesses and going remote, and I’m not going to lie, Rachel. I spent way too much time browsing people’s Instagrams, looking at…

Like on the beach in Bali, with the laptop, the most attractive people you’ve ever seen in your life, drinking coconuts all day. I was like, I had set the bar way too high, and so when I eventually left, all these massive problems happened, right? I invested all this money in the next phase of the course to expand it. I got to Bali. The first day I get to Bali, I get robbed by the police, right?

Rachel Brenke: Oh, my god.

Tommy Griffith: Within the first week, I got food poisoning, and I was throwing up everywhere, and then I had recorded this whole next version of the course, and it was raining really hard on the warehouse we had rented, so all the audio was messed up. I spent $15,000 on filming everything, and all the audio was messed up.

I’m sitting in an Airbnb in Bali. I had just been robbed by the police. I was throwing up everywhere. I’m clutching this external hard drive with $15,000 worth of garbage footage on it, and I just… I’m looking up at the sky, thinking about unlimited breakfast, lunch, and dinner at Airbnb, and the MacBooks, and the beanbag chairs, and all that Silicon Valley stuff, and I’m just sitting, looking at the sky, thinking, what am I doing? Why am I here? I think, look, a lot of people, they’re very hesitant to make the jump into entrepreneurship, and it’s really reasonable. It’s really reasonable. Startups are hard. Most startups fail, and it can be absolutely brutal, but the other aspect of it that is worth thinking about is your own expectations for how it’s going to go. I gave myself way too much of these really high expectations, and when it didn’t go absolutely perfect, and absolutely according to plan, I was absolutely miserable.

The one thing I would say to keep in mind, if you’re going to make the leap, is just to keep your expectation as close to rock bottom as possible, because it’ll make your life a lot easier going forward.

Rachel Brenke: You know what? I think that’s pretty manageable for most people, and not… Your success line moves, and unless you’re… At least for me, and one of the clients that I work with is that you’ll… They’ll get to the line, and they’ll go, okay. Now let’s move it again, and so they do this incremental, and I don’t know if it’s because there’s a fear in it, or what the approach is, but for me, maybe I did… I had no expectations, and that was why I kind of say, I woke up one day, and there I was. Didn’t really. I put in the elbow grease and got there, but I didn’t really have a, I have to hit this metric by this date. The kind of pie in the sky goal was support my family, and what does that look like? I had a number for that, and kind of things that I wanted us to do, but it wasn’t, like I said, had to be this date, this time, and so yeah. I had relatively low expectations, was that…

That wasn’t an intentional thing. I just think it happened because I really wasn’t sure if I was going to be able to make it happen. Maybe there was just an element of failure in the back of my mind. I don’t know.

Tommy Griffith: Interesting. That’s interesting.

Rachel Brenke: I feel like I’m laying on a psychologist’s couch right now, [inaudible 00:28:06].

Tommy Griffith: Sometimes we all need that, right? Entrepreneurs need to figure out what is wrong with them.

Rachel Brenke: Right, so you’re talking about side project, going full-time on the project, but what happened in like the first three months of going full-time? You just shared with us about the expectations being super high. You had to bring them down. That was all within the first three months, right?

Tommy Griffith: Yeah. That was it. Those were the… That was sort of the brutal realization that I had left, and it’s also very interesting, too. There’s a lot of writing and thinking around this now, around having skin in the game. I don’t know if you’ve read that book by Nassim Taleb, I think is his name. He’s got this really interesting idea around how… It’s basically you shouldn’t be taking advice from people unless they’re, unless they have skin in the game, unless they’re actually out there doing it. I had this pretty brutal realization that some listeners might come to as well, which is I love search engine optimization. I originally got into it by being like a self-practitioner, but then I went into Silicon Valley, and did, was doing it at these big companies that have a lot of these massive advantages.

What I realized was, I was giving… I was getting way more credit than I deserved, right? Doing search engine optimization at these big companies is a very different thing than going back out, and doing it on your own, and so a very brutal realization I had when I left, and finally went to go out and do it on my own, was I started doing research, and looking at competitors, and looking at all the stuff I had glossed over over the last few years. I suddenly realized, oh, my god. All of these other guys out there that I’ve never even heard of are way, way better at this than me. I had been given more credit than I was due, working at Airbnb, and that happens. The people sort of naturally believe this sort of… It’s like this sort of arm’s length testimonial you get when you work at a big company, and so that was pretty brutal, but we…

I started to get back into it. I started to create the product, had all these mishaps at the beginning, and just continued to power through it. We eventually ended up launching sort of the next version of the course, and had a bunch more spikes and valleys. Again, we had this… We pre-sold everything, and we expanded the course from just SEO to seven different types of digital marketing courses. We had this huge run up in sales when we did a presale, and then everything crashed again right afterwards with a bunch of mistakes we made, so it’s just this kind of massive journey of big pockets of a ton of revenue, and then a devastating failure, for probably the first year. It was pretty tough.

Rachel Brenke: How do you manage that, though? We’ve talked about failed businesses, and just kind of like, for me, killing brands, but your… It’s within your business, so you’re like riding the ship as you go along. You’ve got little pockets of stuff, like you said. How do you adjust the ship’s course after that occurs, especially when it’s a big monetary outlay? I share this because those that are listening, who may still be on the side project side of the fence, they may be worried about what happens if there is failures once I take this big risk.

Tommy Griffith: Yeah, so there were two big things that happened, and both were… One was pretty controversial, so the first one was, I came to the realization that I wasn’t up for the job. I was sort of the kind of guy who, I was able to get the first 10,000 users, and was able to get the company to the first $100,000 and all that, but the next phase of it, I wasn’t good at. I wasn’t good at processes, and a lot, some of the hiring stuff, and looking at a lot of our metrics, and trying to optimize them. I was kind of the guy who goes from zero to 100, and not 100 to whatever. You know what I mean? I ended up… This is pretty controversial. I ended up bringing a co-founder on, on my fourth or fifth year into the business, and it was a guy… I do a lot of the apprenticeship model. I used to teach at a university in San Francisco, and at the end of every course, I would always grab one apprentice at the end of every course, would offer it up, and say, “Hey, this is like a very low paid sort of internship, but you’re going to learn more with me than you ever would anywhere else.”

Every one of my apprentices went off to do great, interesting things in Silicon Valley in digital marketing, but one of them was this guy, Eduardo, who was my apprentice for a while, and we worked together for a little bit, and then I basically sent him this desperation, hail Mary email when, in between throwing up in Bali and trying to fix my audio. I basically… We had worked together for a while, and I said, “Hey, man. Here’s the situation.” He had a good job in New York, and I said, “Here’s the situation. What do you think?” We worked on some things together, and then I basically offered him a co-founder role, and it was really interesting because everyone I asked said, “Don’t do it.” The reasons why they said, “Don’t do it” were very logical. It was exactly what you would, the conclusion you would come to when you open an Excel sheet, right, and do the numbers.

But the reality was, it was so comically obvious that I needed him, to me, because I just knew… I know my strengths, and it was just one of these things where I gave, I pushed a lot more into his corner, and he sort of ran with it, and just everything, everything started to improve after that. One of the things, and I’ve found so many people doing this, they get too much into these logical Excel sheet sort of ideas, and they, just to be frank, there’s not really another word for it, but they’re just a little bit greedy, and they don’t… There’s just a huge difference between… Okay, the first conclusion everyone comes to is to say, “Okay, there’s a problem. Let me hire a consultant, or let me bring someone on for 10 hours a week, or 20 hours a week to fix things.” There’s something very different when you bring on someone who’s ready to go to war with you.

It was like, he quit his job. He moved, he flew to Europe to be with his girlfriend, and he decided to spend 50 hours a week for two years on this thing with me. That’s very… It’s really hard to put a price on that kind of thing, and so that was the first big thing, was having a… Having someone to share the struggle with really changed a lot of the dynamic, I guess, is sort of what happened there. The-

Rachel Brenke: That’s what I was thinking about, when you were talking about bringing him on as a co-owner, a co-founder, I’m thinking, well, why didn’t you just get a business manager to fill that role, but this is circling back to what you were saying earlier about skin in the game, because I have also gone down the path of almost offering ownership before, and I freaked out. I’ve also, on one of my business, I am a co-owner with somebody else, and so I see the pluses and minuses on both sides, but I love the skin in the game idea of, and I am glad that we’re sharing this. This may be a little longer in the future than most people are listening that have a side project, but never count it out, because when I initially started, I never ever had the mindset that I would ever sell my businesses. I was like, no way. They’re my babies. I’m never going to do that. No way. I’m never going to [inaudible 00:35:40] to anyone else, but like I was talking about earlier, the success finish line keeps getting moved as you progress, and as you mature, and you grow.

I think these sort of things also evolve, and change, and grow, and just to keep an open mind, and the whole skin in the game idea. When someone else’s neck is also on the line, in a decision they’re going to make, they’re going to really look at that decision as opposed if they’re just an employee punching the paycheck, I mean punching the clock to get a paycheck.

Tommy Griffith: Right. Yeah. For sure. Not only does it change their sort of… Yeah, their psychology, but I think the other thing to keep in mind, and you’re right. If you’re just in the early phases of this, this might be a little long in the tooth, and too far out, but the other thing to keep in mind is where you have your advantages. I think it’s like… It’s just, even at the top tier of this thing, most Silicon Valley founders don’t… I don’t know if it’s most, but a lot of them don’t take their own companies public, because it’s in a… You have to become an entirely different person from the first 10 employees, to the first thousand employees, to when you’re becoming a public company. You have to do quarterly earnings reports for… You’re an entirely different skillset, so I don’t understand why it’s so crazy to think that that also, that’s also true on the lifestyle business level, right?

It was pretty easy for me to… Not easy, but it was fairly natural for me to get the company up to kind of the first six figures, and then Eduardo was just one of these guys who wouldn’t give him as an asset that’s as traffic generating, and emails coming in every day, and people that are buying the product, he was the guy that can optimize it, and tweak it, and kind of double revenue overnight sort of thing, and so that… It was just the… It looked crazy to everyone else, and it was so hilariously obvious to me, that, but I think it still comes down to where you have your unfair advantages. I didn’t realize this at the time, but looking back in hindsight, we were accidentally really good at this, at just being relentlessly focused on honing in on our unfair advantages and letting everything else drop to the wayside. You know what I mean?

Rachel Brenke: Mm-hmm (affirmative). Mm-hmm (affirmative), so within the context of all this, how’s Clickminded doing now? Obviously if we’re talking about it, are we in the throes of success? Are you still learning? Where are we at? Where are you at?

Tommy Griffith: Yeah, so it’s been great, yeah, so Clickminded now has transformed from the dorky, Saturday morning in-person SEO training course to a full sort of comprehensive thing. We have seven different courses on digital marketing, right? It’s all online. We kind of focus on entrepreneurs, in-house marketers, or consultants and agencies that want to use digital marketing to grow their business, and our model is, we try and find world class people that do this stuff every day to teach it, right? For example, our social media course is taught by the former head of social media at Airbnb. The content marketing course is taught by the former content strategist from Lyft, and we try and get sort of the expert opinion on all these people, and teach it in our courses. It’s been a lot of fun.

Rachel Brenke: That’s awesome, and I love the fact that we kind of probably went a little beyond in the big picture that we wanted to for this subject matter, but I think it’s good, because all of you guys listening, whether you’re in a position of, I have a side project, and I want to grow this full-time, or you’re like, oh, well, I have a side project. I’m happy with my corporate job. You just never know where that side project will go. You never know if you’re going to need this information. It could be the next big thing. It could be the next Airbnb. You don’t know where it’s going to go, and so having this, and having someone like Tommy to be able to come, and just transparently share all of this, I greatly appreciate. Is there one last tip that you want to leave with someone who may be sitting there with a side project, and a full-time corporate job right now? However direction you want to take it, just one last tip to leave them with?

Tommy Griffith: Yeah. Sure. I think the biggest thing… Actually, I have two. The first one is the thousand day rule. This is going around in a lot of entrepreneur circles now, and the basic idea is it takes about 1,000 days to get your side project up to where your current income is. It is scary how accurate this thing is. I’m actually curious if you know what your count is, Rachel, but for me, it was like, I heard this number, and then I looked back, and it was like 1,040 days, or it was very, very close for me, but that’s pretty brutal if you’re just thinking about it now. That’s about three years, and a lot of people, they-

Rachel Brenke: That’s about what mine was, yeah.

Tommy Griffith: Yeah. Interesting. Yeah, and so a lot of people, they’re on Instagram. They’re on Pinterest. They’re following influencers, and they think they’re going to create a drop shipping site that’ll be like a million dollar business by tomorrow, and the reality is the struggle is a little bit longer than that. The last thing, one of my buddies, Dan Andrews, he runs an entrepreneur group I’m a part of, and he coined this term that I really love called exit velocity. The basic idea is, people… You’re doing things in your everyday life now, at your job, that you probably are generating advantages from, and you should use that on your side project, right? Just pulling… I have the definition here. I just pulled it up, so exit velocity is the amount of professional and entrepreneurial momentum you have when quitting your job, and starting a new venture.

Momentum can come from a variety of sources. Investment, capital, experience, anchor clients, industry knowledge, and connections, AKA unfair advantage. The idea here is, okay, maybe you’re a corporate lawyer for 20 years, and you’ve been doing corporate law, and then all of a sudden, the next day you’re going to go sell crossfit jump ropes, right? You have no exit velocity when you do that, right? Let’s say you’re a doctor, and then you want to go suddenly start doing a paleo carrot cake recipe website. Okay, if you love these things, that’s fine. Of course, go do your passion, but you’re probably doing things every day in life now that can give you an unfair advantage on your side project. For me, my first business was a really dumb idea. I had no unfair advantage, but the one that finally worked, Clickminded, I was doing enterprise SEO at PayPal and Airbnb, and then teaching SEO on the side. I was using my own side project on my, at my current job, and I was building up the revenue to the day that I left.

I had accidentally generated a lot of exit velocity, and I’d highly recommend anyone listening, if you’re working on something now, and you enjoy it, think about the ways that you can leverage your current situation to get exit velocity for when you inevitably leave your current job.

Rachel Brenke: I love it. Great. You guys have gotten more than you bargained for in this episode. Tommy, thank you so much for coming on to talk about side project to full-time. If you guys want to learn more about Tommy, I’m going to put all the links in the show notes, and also with the transcript at Also make sure you jump into the Facebook group. We’re going to be having lots of giveaways and stuff coming up as the end of the year comes about, and maybe Tommy will join us in there. We can see more about what he has going on. I know that this episode is going to be a hit, because so many of you have reached out and asked me this very specific topic. Please, go back and listen. A lot of great info. Go check the show notes. Make a list. Make notes, and please, enjoy the beginnings of your business. You guys know I love the very beginning, so enjoy it. Learn lessons, and I look forward to seeing you guys on the other side.

Speaker 2: Thanks for joining Rachel on this episode of The Business Bites. For show notes, a list of recommended tools, or referenced episodes, you can find them at Until next time.

Featured Guest & Resources

Tommy Griffith has been doing search engine optimization for more than 10 years. He previously managed SEO at PayPal and Airbnb and now runs ClickMinded, a digital marketing training platform for marketers and entrepreneurs.

Tommy started ClickMinded as a side project while working full-time at Airbnb. He grew it until it started generating more revenue than his annual salary. Two years ago, he quit Airbnb to go full-time on it and ran into a number of problems in trying to grow the business from there.


You can find Tommy here:

Hi, I’m Rachel Brenke

Rachel Brenke

As a mom, team USA athlete and cancer-survivor, I want a real life while I have a real business.  This is why my resources don’t promote hustle-culture, rather tough-love and no-holds-barred tips to achieving both.  In addition to this website, I have a top-ranked business podcast, been featured in places like Forbes and work 1:1 with so many of you.

Enough about me though. I am proud of you for pursuing entrepreneurship. It is rewarding and amazing.  Keep at it!

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