Episode 1: Launching a drone photography website

Posted on December 31st, 2019 by in History Read Times.

Benjamin Doolittle U.E. | FourtyBee

Launching a drone photography website
Interview

 
00:00 / 5:48
 
1X
 

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Items mentioned in this episode:

Transcript

Rob: In this Taberrific episode of Startups for the Rest of Us, Mike returns to the show. This is Startups for the Rest of Us episode 458.

Welcome to Startups for the Rest of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing startups, whether you’ve built your fifth startup or you’re working on your first. I’m Rob.

FourtyBee is an outlet to publish aerial photos, videos, and stories about the evolution of drone technology, documenting ongoing land encroachments; residential and commercial development. We capture images, videos and stories from landmarks to people, we research the history of Grand River Country (and beyond) from a Mohawk perspective.

Mike: And I’m Mike.

Rob: And we’re here to share our experiences to help you avoid the mistakes we’ve made on our journeys. Mike, it’s been a long time.

Mike: Hi. Yeah, it has. What? 10 episodes?

Rob: Ten episodes. I don’t think either of us realized that it would be that long. Just so listeners know, you and I had literally not spoken verbally. We’ve texted since that episode, but we have not spoken since episode 448.

Mike: That’s true.

Rob: We’re not talking that much. We tend to text and email a lot.

Mike: I hear that from people when I talk to them at MicroConf. They have the expectation or the inclination to believe that you and I talk either everyday or at least a couple of times a week. That’s totally not true. We’ll email back and forth. We will sometimes go for a couple of weeks without talking at all.

Rob: Yeah, if we don’t record the podcast. Ten episodes. What have you been doing with the enormous amount of free time you had not had? Showing up every week to record this and all that.

Mike: I’ve come to the realization that I was probably recovering from a pretty massive dose of burnout. I feel like I’m at the tail end of getting over that. How do I put this? There were times where I would just take an entire day off just because I felt like I needed it. Then, there are other times where I would just sit at my desk. I really wouldn’t feel like I was getting any work done. I would say that was the early stage when I started to take the time off.

I got to the point where I realize just sitting at my desk wasn’t actually doing anything. If I wasn’t actually being productive in any ways to perform, I’ll just get up and go do something else. What’s the point of sitting there if it’s not doing me any good? Because then, I’m just going to feel bad about it later and that’s not good for me either. It was rough to get through, but it was probably necessary, too.

Rob: It’s nice to have the luxury to be able to take that time and did not have to show up everyday for a season. It’s like over the course of years, you need to show up everyday in general, but when you’re burned out, you have to take time off. There’s really no other way to get around that. You have to get away from it. It’s hard to show up even once a week and be like, “All right. I’ve got to sit there and talk on the mic about stuff that I don’t really feel great about.” I’ve gone through months of time when I felt that way. When I listen back to the show, I can hear that in either one of us at a given time when they’re burned out.

It’s great you have that time to step away. You just got to give yourself permission to do that. That’s the thing. I often feel guilty when I do it, but you come back the next day or the next week assuming it’s not a long term depression or a chemical imbalance, which is totally very valid and real thing. But assuming it’s not that and you are just burned out because of the work or whatever it is, it’s super valuable. Each of us should give ourselves permission to do that.

Mike: Yeah. That was a good realization for me is just giving myself permission to walk away then come back later either when I felt like it or maybe the next day if I didn’t feel like it. Sometimes, there were definitely a couple of periods where I would take two or three days just because I didn’t feel like doing anything and I wasn’t being productive. You can’t beat yourself up all the time because that’s really what was happening to me. I don’t know how long it was going on, either.

When you’re sitting there trying to get work done, it’s like you’re concentrating more on beating yourself up about why you’re not getting things done, not focused, and not moving at all forward. Then, you are about taking a larger view of things saying, “How long does this been going on?” I try to forgive myself, I guess, for those periods of not being able to get stuff done. Like I said, things just has gotten a lot better over the past month or so.

Rob: We’ll dive into that. That’s the whole point of this episode. I have a couple of questions for you before we get into what you’ve been thinking about, how things have been with your health, your progress, and what’s going on. Have you been listening to the podcast?

Mike: I’ve not. I’ve gone into hermit mode.

Rob: Yes. You haven’t been on Twitter at all, right?

Mike: Aside from logging in very briefly on Twitter and Facebook just for authentication purposes for a couple of different things, I haven’t gone on either one of them. Nothing. No social media. I don’t even really watch the news or anything like that. There’s stuff going on. I’m just like, “I have no idea what’s happening in the world.” It’s just hermit mode.

Rob: Mike, do you miss it desperately and feel like there’s a huge Twitter-shaped hole in your heart?

Mike: No, not really.

Rob: Not at all?

Mike: I do miss some of the playful interactions and stuff like that. At the same time, I know they’re also distracting for me. I miss reconnecting with people just to shoot them a message here and there, and just make a comment on different things that are going on. At the same time, a lot of those doesn’t necessarily add any real value for me. I guess there’s a social contact, but I’ve tried to find personal social contacts outside of the internet.

Rob: That makes a lot of sense. I find it fascinating you have been listening to the podcast at all. The listeners who’ve been listening, they know the format. I’ve changed the format. I’ve been doing a lot of interviews, really trying to dig in and not just do the same old. We never wanted an interview show. There were enough interview shows. I’ve been trying to dig into people’s stories and the struggles. Done several Q&A episodes. I did a Q&A episode where Tracy Osborn came on and co-hosted with me. Jordan Gal came on for one.

That’s been actually the cool part for me. It was almost an excuse/motivation/force to me to figure out how I run the show on my own. It forced me to innovate. It’s the mother of invention to sit here, stare at the mic, and be like, I don’t just want to do what a lot of solo hosts do which is interviews. I don’t just want to monologue on the mic. Heaven knows I can sit and talk for 30 minutes. How do I try to up the game?

I’ve been spending a lot more time on the podcast than I used to. Over the course of the last several years, we show up and we talked about on the mic, but I’ve been trying to be really deliberate about trying to craft stories, just experimenting with new ideas, and new formats. It’s been cool. You can go back and listen to them now, I think your hermit mode is great, and it’s probably what you needed at this point. Someday, go back and listen, and let me know what you think.

The response I have asked in some of the episodes for folks to write in, or write me personally, or tweet, or somehow give their thoughts on the new format are overwhelmingly positive. I probably got 20-25 responses saying, “Yup, this is great.” “Keep being creative.” “Keep changing it up.” Some folks have mentioned that they missed the Q&A episodes probably the most. We used to do it every other episode, this Q&A.

That’s easy enough. I did one that went live today when we’re recording this. It was just me doing Q&A. I listen through it and it’s good. I think that works. I also like bringing experienced folks like Jordan Gal or Tracy to co-host with me on the Q&A. I think I’m finding my groove here in a way to keep it going.

Mike: Yeah. It’s interesting that you bring up the forced innovation. There’s a couple of things that come to mind in terms of just the podcast in general. I call it a general success and general longevity. The fact that we show up all the time, I guess until 10 episodes, we show up every week. Then, the past 10 has just been you showing up every week. The fact that it’s there and people can rely on it is not just a testament to the show, but it’s one of the reasons why it has been successful.

The other thing that you look at is you can continue to do the same thing over and over again, but eventually, maybe it gets boring. Maybe you decided that there’s other things that you want to do or there’s other ways to innovate on this show or whatever it is you’re working on. Those things don’t get done sometimes unless you force it because you’re either afraid to make changes or you decide, “I’m comfortable now. I don’t want to go through the…” I don’t want to call it pain but the uncomfortable mess of trying to change something that is already working. That applies in not just the podcast but in a lot of other places, too.

Rob: I would agree. I actually have a snippet from one email that we received from […]. He had a couple of comments, but one thing he said, it was indicative of what a lot of folks said. He said, “You asked for feedback about the new format. I’m really enjoying the in-depth nitty-gritty interviews with entrepreneurs who are in the trenches and openly talk about their successes, failures, and what they’re currently working on. It’s so valuable to hear what people think through the challenges, problems, and decisions. You’re a great interviewer because it doesn’t feel like you’re an interviewer, if that makes sense.”

I really appreciate that piece because I’m trying to deliberately do that. I’m not trying to be an investigative journalist. I’m trying to be a founder who’s just having a conversation with another founder much likely we would have whatever, at a bar, or at a conference in hallway track or something.

Back to his email, he says, “I also appreciate how you introduce the guest’s background yourself so you can go right into the good stuff with your guest.” That’s been very deliberate. The first 2-3 minutes, I hammer through their history so that we don’t have to sit there for 20 minutes talking through, “So, when did you become an entrepreneur?” Nobody really cares about that, in general. We really want to know what’s this pivotal piece of your story and let’s dig into that; that element of it.

His emails continues. He says, “I’ve learned so much from the topic-focused/listener-questions episodes as well.” That’s some more of the older format. “There’s so many concepts I’ve incorporated into my own thinking that have made me vastly more productive and effective.” It’s cool he rattles up a bunch. He said off the top of my head, relentless execution, road blocks versus speed bumps, almost all decisions are reversible, good glucose, moving a business forward, I could go on. He says, “I like the new format. I like the new voices, I like the stories, but the previous format is also great and it has taught me a lot.”

I appreciate that email. That was in general, indicative of the feedback that I saw. There was one person who wrote in and said, “I like the old format better.” That’s not super helpful without more description, but yeah, in general, it’s been a fun adventure.

Mike: That was cool.

Rob: How about the website? Have you been to the website? I’m about to announce it today, but about a week-and-a-half ago, brand new, Startups for the Rest of Us website went live.

Mike: I did see that.

Rob: It’s a new WordPress design. I’m sorry that I had to deprecate our 9½ year old WooTheme that we customized. Oh Mike, the humanity.

Mike: That was so hard to work with.

Rob: It’s not because it’s a WooTheme, it’s because it’s 9 years old. It was so crafty. Everything was breaking. We have plugins that were deprecated six years ago. Thanks again to Rich Staats at the Secret Stache who jumped in. The podcast feed would have died three months ago. We weren’t able to get new episodes in. He jumped in a day’s notice and hacked something in a plugin to get that going. That was cool. It keeps us going.

I don’t know if you know, but we’re now on Seriously Simple Podcast hosting which is Craig Hewitt’s WordPress plugin. We were in ProdPress and it hadn’t been touched in six years. Craig did us a favor, jumped in, and spent several hours migrating us over. We were just bailing the water out of the boat, in essence, to keep the podcast going. That’s cool. Now, we have a new theme. My hope is that we’re in a much better situation now.

Mike: Yup. In 2027, we can update it again.

Rob: It’s the thing I was thinking. It was like, “Oh my. We need to do this a little more often.”

Mike: It might be a good idea, but I think we both just got busy doing other things. It’s still work and it’s functional, it’s a little along the priority list.

Rob: Yup, that’s right.

Mike: That happens.

Rob: I was motivated by the fact that the momentum carried through were I was like, “Okay, here I am doing this show on my own, setting up interviews.” I kept going to the site and being just like, “I’m so bothered by this website.” The copy’s out of date. The greatest hits ends at 220, it’s like half of our podcast feed had been analyzed for greatest hit, and just the design and everything. It’s never fun to redesign a site, but it’s fun to have redesigned it. Now that it’s done, I’m glad that it’s all taken care of.

Mike: Now that it’s over and it looks nice, then it’s much better off.

Rob: Yeah. Episode 448 really struck a nerve. We received north of three dozen comments on that episode, tweets, emails to myself, emails to questions@startupsfortherestofus.com. It is the episode that received the most feedback, perhaps, of any episode in our 450 episode run.

Mike: Yeah. You can probably at least add 50%-75% to that. I’ve got a ton of things that came directly to me through email as well. I don’t know if anybody has tweeted at me. If they did, I apologize because I have not logged into Twitter since 2½ months ago. On top of that, I’ve got a ton of personal direct emails to me, as well.

Rob: That’s cool. Thank you to everyone who reached out, honestly. I’ve responded to a lot of them, but I read every single one of them. I know you did as well, the stuff that came to you, Mike. In general, it was just super encouraging. There was a voicemail last episode that I felt like it had a couple of questions. He had a piece that I felt summed it up nicely. He said, “I wanted to take Mike for his immense courage in being so open and vulnerable in sharing his Bluetick blues with the podcast community. As a fellow, still struggling in Boston area, B2B SaaS founder, I empathize with him in the challenge he’s facing and I deeply appreciate his willingness to share them in public. I wish him the best in deciding what’s next.”

I felt that was, in general, like, “Thanks for coming in the mic and doing this, both of you.” “Thanks for diving into this difficult topic in front of 20,000 listeners,” and, “This is helpful.” That’s what I keep hearing is, “This is helpful for me to hear as a founder to know that I’ve gone through this, I am going through this.” It really humanizes it and a lot resonated with a lot of people that we were able to dig into that for 40 minutes, 10 episodes ago.

Mike: Yeah. When that episode went live, I got inundated with a ton of emails upfront. Then, they just kept trickling in. They tapered off after three or four weeks. It was hard for me because I wanted to respond to every single one of them, but I just really wasn’t in a place where I could. I apologize to anyone who I didn’t respond to. I started replying to them and I got to a point where I just couldn’t. It was like I was seeing the same things over and over again to people which is continuing to beat me down, I guess. Apologies to anyone, but I do want to say, definitely, I want to thank anyone who did email me. I did appreciate it.

Rob: Mike, when we last left our hero, we were talking about […] of things. I have seven or eight bullet points here to cover and revisit. You don’t need an answer to all of them. Some of the answers maybe. I don’t know. I haven’t figured that out yet. To take 2½ months off and expect that everything is thought through, everything is fixed, I don’t think is realistic. I am curious and I’m sure the listeners are, too. Did you give this particular bullet a thought? What’s your conclusion? Where do you stand now? Where do you see it heading over the next months and years?

To start high level, a question I brought up a couple of times in that episode was, “Do you still want to be an entrepreneur?” and you said, “The answer is absolutely yes.” That’s cool. The other question towards the end, “Should you be an entrepreneur? Do you feel like this is what you should be doing? Or do you feel like you should—not want to, but should—take a step back? Do some consulting? Build up the bankroll? Take a salary job?” because healthcare is so expensive. I know salary jobs make both of us sad. They make me depressed, but they are so stable, they’re so much less stressful, and there’s less need for that intrinsic motivation. Did you have a chance to think through that stuff?

Mike: I did think about it. Coincidentally, it was maybe four or five days ago, I got an email from a recruiter who was asking me. He’s like, “Hey, I saw your job experiences and stuff on LinkedIn. There’s a position over here at Amazon that you’d be really good for.” I looked at it and I thought for eight or ten seconds, “Oh my God, No. I just can’t do that.” Not just the fact that it would be all the way up for in Summerville. It’s taken me an hour to get there, so no. Absolutely not. That’s part of why I went out on my own anyway.

The thought of going back to a full time employment, there is an attraction from just the healthcare standpoint, but at the same time the lack of flexibility. The past couple of months, we’ve been able to make things work because I’m working at home. My wife’s got her business. She’s in and out. We just tag team on all the stuff with the kids during the summer. It’ll be so much harder if I had a fulltime job. Yeah, I could probably make it work if I were working remotely, but it’s still just the hassle of working for somebody else.

I saw this Dilbert comic. My wife and I actually talked about this, me going back and working for somebody else. I remember coming across this Dilbert comic very recently that really summed it up. The boss comes in and he says to Dilbert, “Hey, good news. We just won this nationwide contracts to roll out a wireless network.” Dilbert says, “Newsflash: We don’t know how to roll out a wireless network nationwide.” The boss says, “How hard could it be to not roll out wires?” That completely sums up exactly why.

Don’t get me wrong. Not every company is like that. But there are some things that I see that companies done where you’re just like, “This is the dumbest thing ever.” Yet, it’s hard to say something in those situations. Then you come off as an adversarial employee, you’re not working with the team, it’s just like, “Come on. This is a dumb idea. I can’t believe you don’t see it.”

Rob: Did you just quote a Dilbert comic as a reason not to get a full-time job?

Mike: I think so.

Rob: I hear what you’re saying. Honestly, if you were to get a job, it should be for a startup. It should be for 10, 20, 30, person company. Probably, with funding so they have good benefits and it should be remote.

I get it. I’m not saying you should do this, but I think that not wanting to go back to the cubicle form or the hour commute, I get that. Neither of us should do that. But I don’t think you need to in this day and age.

Mike: Yeah, I totally agree. I could probably find something that’s remote. I thought a lot about it. Even if I had all the money in the world, I would still build stuff. The problem with that is that money isn’t necessarily a main driver for me. That’s the problem that I’ve run into. I have enough money in the bank and I have enough income coming in where I don’t have to work my ass off in order to have the things in life that make me happy. The problem is I’m not really making a ton of forward progress on a lot of things.

It really comes down to an existential question of, “What is it that actually drives me if it’s not money?” It used to be money because I was the only one in my household who was working and now I’m not. My wife is able to help out with the income side of things. It’s great because now I don’t have to push myself nearly as hard. But as a direct result of that, the question is, if I don’t have to work nearly as hard, why am I doing this? What’s the point?

It’s something I definitely struggled with, to be perfectly honest. I don’t have a great answer for it yet. I’m still working on that, but the reality is, that is what stopped me or prevented me for going full speed on a lot of stuff because I haven’t needed the money, so what’s the point?

Rob: That makes sense, although you’re not independently wealthy. You do have to work. If you stopped working altogether, it’s not like you can take five years off. When I was in your shoes, that was my motivation. It was to get to a point where I could take years off or the rest of my life to achieve financial freedom. It’s an overused term and it’s almost devoid of meaning at this point, but I wanted the ability to never have to work again. That was a big motivation for me. Does that not motivate you?

Mike: I feel like the runway’s long enough. It’s not like a hardcore motivator for me, if that makes sense. I’m not under the gun. I don’t have two months or whatever to make ends meet or I’m done and I have to go find a full time job because that’s not the position I’m in. I’m fine for probably several years. That’s not a big deal. The problem is that there are going to be points along the way.

Let’s say Bluetick completely went away, for example, I lose that income. Yeah, I would probably be in a little bit of trouble, but I would still have plenty of runway left to figure out what I was doing at that point. The question is how do I address that? What do I really want? What am I really looking for?

I don’t necessarily have specific answers for that. I’m still working on those. I agree that the financial freedom aspect of it is a good and worthy goal. The question is, what is it that I’m really looking for above and beyond that? If I have that, what am I going to do? What’s going to drive me and motivate me? Even if I achieved that, then what’s next? What’s going to prevent me from just saying, “Okay, now what?”

Rob: That’s so interesting. I hear you, but I would get to that point then say, now what? I have gotten to that point a number of times. For me, quitting a salary job was this huge goal of mine. I quit it and went full time contracting, remote, consulting, in, let’s say, 2002 or 2003. I remembered being like, “Oh my gosh! This is it. I’ve dreamed of this for 20 years since I was in high school. I wanted to have this remote job.” And I did. Six months later, I said, “Now what?”

You know what “now what?” for me was? It was, “Huh, I’m bored of working dollars for hours. I want a product. I want a product to support me.” Then, in 2008, I’ve got a full time income from products. I remember loving it for about a year. Then, I said, “Now what? I’m bored. I needed to do something bigger.” That was podcast, conference book, Micropreneur Academy. Then, it was HitTail. It was like, “I need to level up.” Then, after that it was Drip. After Drip, it was, “Now what?” Now, I spend more time in the podcast than I do in TinySeed.

Your and my motivations do not have to be the same thing. That’s not what I’m saying. I do think that the best entrepreneurs I know have a driving motivating factor. It is either to create—to build stuff that people use—or to achieve. There are a bunch of folks who just want to build a big company. They want to build the Amazon, or Google, or the Uber. That’s not my motivation. My motivation has always been to create interesting things that other people can use. I’m sure there are other motivations.

The thing that I’ve seen, if you ever heard of the Enneagram, it’s a personality test. It’s like the Myers-Briggs or whatever. It’ll tell you, “This is what motivates you and this is what doesn’t.” I’d be fascinated for you to take that. Whether you talk about it on the show or you just take it for yourself to get some insight into your likes, dislikes, your pros and cons, strengths and weaknesses, and your motivations.

I think that until you know that, it’s going to be a challenge for you to really be motivated to launch products because this […] is hard. That’s what we’ve experienced. It is hard to do this. Without a real drive of, “Man, I need financial freedom,” or, “I need to create stuff that a bunch of people can use,” or, “I just need to escape this inner voice in my head that probably my dad or my mom put in me.”

These are the motivations that I’ve seen drive entrepreneurs to do really interesting things. I don’t even mean great things, you don’t have to build a multimillion dollar business. That’s not what Startups for the Rest of Us is about. It can just be about shipping cool things into the world that people use and showing up everyday to do it.

Mike: Yeah. Part of my question that I’m kicking around in my head is, what is it that I want? All of the things you talked about are like, different people have different goals. Some may want to build the next Amazon and for you personally, that doesn’t resonate. It’s not what you want. But when you’re talking about your journey from going to self employment to building a product then to HitTail, Drip, and TinySeed, that whole journey is a series of challenges that you’re undertaking.

In my mind, what I’m really struggling with is what is the challenge that I actually want to tackle? What is it that I personally want to do. That’s not something that comes over night. Especially, if you have the time to figure out what it is you want to do rather to be in having some forcing function that makes you decide within a week. Within a week, that’s a time constraint. You have to deal with the constraints right there and then versus I’m in a position where I can take some time to figure out what it is I actually want, reflect on exactly why that is, and why it’s going to make me happy. If it’s not going to make me happy, I don’t want to do it.

Rob: You’re right. Until you’ve been there, it’s hard to understand how saying, “I can move and live anywhere,” actually makes it a lot harder. It’s tough to say, “I can build or do anything. I have a few years of runway,” makes the choice a lot harder because there is no forcing function for you to make a decision. There’s not a ton of things pressing on you to do it. I hear what you’re saying.

It sounds like, “Here’s what I’d like to do with this because this is really an interesting topic.” I noted, “What is the challenge that Mike wants to tackle? Why is he doing this?” I want to revisit this. I think that you should give a thought, do a retreat, do whatever it is that you’re going to do to figure that out. Take the Enneagram. I’ll just put the link. It’s not a silver bullet. Take it. Take some personality test and do some thinking and stuff. Think about what it is you want to do. This is a time to be deliberate about these things.

The mistakes that I’ve seen some founders make, it’s a founder I have in mind in particular, he sold a company and sold it for several hundred thousand dollars and didn’t have enough to retire, but he could take time off. He didn’t take time off. He made a quick decision that said, “I got to get right back on.” He launched this next thing within a few weeks. It was a mistake because it was almost like a rebound, like a rebound startup or like a rebound idea.

You’re not in a position to where you’re shutting Bluetick down and looking for another thing. You are in a place where you have the luxury of taking a month or two, set a timeline so you don’t take a year or two, but figure it out. That’d be my advice. What do you think? Do you think I’m full of BS?

Mike: Well yeah, but no. That’s a great way to phrase that question. I like that. An excellent point about the fact that when you got a blank slate, you can live anywhere, and you can do anything, what is it that you’re going to do? When you’re facing the problem, there’s all those constraints. It helps guide you in the right direction. But when you have no constraints or very, very few that makes it a lot harder. That’s the position I’m in. I have much fewer constraints on me now than I probably did five or six years ago.

Rob: The paradox of choice.

Mike: Yeah. I’m just trying to make sure that I make the right choice for myself, go in a direction that is going to make me happy, and that’s actually what I want to do. I remember a time when I was a kid. I was like, “I want to do this. I want to do this. I want to do this.”

Fast forward 30 years and you don’t have time in your life to do all of those things. The question I’m trying to answer for myself is, in 10 years, or 15, or 20 years, when I look back on my life, what is it that I want to have achieved? What would make me happy? Or what do I believe would make me happy? That’s what I’m trying to figure out right now.

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