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Episode 444 | Our Biggest Regrets, Feelings of Isolation, Impact of Management Tasks on Deep Work and More Listener Questions

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Show Notes

In this episode of Startups For The Rest Of Us, Rob and Mike answer a number of listener questions on topics including what are their biggest regrets, how to deal with the loneliness of building a startup, and task management.

Items mentioned in this episode:

Transcript

Mike: In this episode of Startups for the Rest of Us, Rob and I are going to be talking about our biggest regrets, feelings of isolation, the impact of management task on deep work, and more listener questions. This is Startups for the Rest of Us Episode 444.

Welcome to Startups for the Rest of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing software products, whether you’ve build your first product or you’re just thinking about it. I’m Mike.

Rob: And I’m definitely not sick today.

Mike: And we are here to share our experiences to help you avoid the same mistakes we’ve made. What’s the word this week, definitely not sick today?

Rob: As bad as this sounds and as much as I hope not to be a pain in our listener’s ears, I actually feel better today than I did yesterday and the day before. You know how sometimes the voice stuff lags what actually feeling bad?

Mike: Yeah.

Rob: That’s how it is now. I’m not 100% for sure but definitely able to record a podcast. I just don’t know if my voice is going to hold, so at a certain point I may just drop off and be like, “I don’t know, Mike. You answer the questions.”

Mike: I’m just going to mute you and I’ll replace you with a text-to-speech converter or something like that.

Rob: Yes, that would be great. But the show must go on, am I right, Mike?

Mike: I suppose it does.

Rob: The show must go on. For me this week, I’m excited MicroConf Europe tickets are on sale. It’s in lovely Dubrovnik, Croatia again at that amazing hotel, where we’re amassing an ocean view, second week October. microconfeurope.com has the full details. Although I just look at it and the speakers are last year’s speakers. We’ll have to get that corrected. We haven’t selected any speakers yet, but know that it’ll be a good show.

Mike: I’m definitely looking forward to going back there although I do remember thinking to myself that because the hotel was built into a cliff right against the ocean, my engineering days came back to me as like I wonder what would happen or what it would take for the whole thing to fall into the ocean.

Rob: I’m hoping that they’ve thought of that. Way to go, Mike, five people just decided not to come because of what you said. I think they’ve thought of that and as far as I know they don’t have earthquakes there. You would never build something like that in California or if you did, you’d really have a lot of supports and such seismic stuff.

Mike: For whatever reason, my brain just goes to those types of things, whether it’s a plane or a giant bridge or something like that. I just think I remember one time, my wife and I were driving back from Massachusetts to New York because that’s where my family is, and there’s this bridge that goes over the Hudson where we stopped on the bridge because traffic was just so bad. We were at a complete standstill and the bridge was popping up and down. Not a lot but it was like four, five, six inches, something like that but you could feel it. The entire car was just bouncing up and down a little bit. All I could think of is that video from grade school or from high school where they show you this bridge that basically just rips itself apart in California.

Rob: It’s in Washington.

Mike: Was it Washington?

Rob: Yeah, in Seattle or that area.

Mike: Oh yes. The Seattle Sound, I think. So that just came to mind. We were out of reason like these giant structures like that is all I can think of sometimes.

Rob: Yeah, I find this as software engineers. Oftentimes, you’re trying to think of everything that could go wrong and when you transfer that into life, sometimes it’s not such an adaptive quality. Sherry will suggest things, “Hey, let’s go visit Mike.” “Here’s six things that could go wrong with that. Again, that’s actually not helpful. How about instead of that, you go on and you select an Airbnb and look-up for the tickets?”

What else? You have a webinar last week, right?

Mike: Yeah, I had a webinar. It was a couple of days ago and I went a little bit longer than I thought I would. I thought it was coming around 40 minutes and it ended up coming around 50–55 just because I went into more depth on a couple of things than I had probably originally expected to. But it was pretty good.

I think there were 46 or 48 people who registered for it. I got their contact information and the list that I got also included their company names, their job titles, where they’re located, the size of the companies, a lot of interesting things there. So, definitely adding those people into my mailing list and working from there.

It was fun. I’ll definitely do it again. It’s just a question of whether or not they would have me and whether it’s applicable to the audience still.

Rob: That makes sense. Did you get any positive feedback or did you get much feedback?

Mike: Very little feedback. There is one person who submitted feedback out of the people who attended. I also got information about who attended and who didn’t. So, there’s emails that go out to them after where it sends them a link to the video. I’ve got a copy of the video as well. It’s typical webinar stuff.

Rob: We did a bunch of webinars in the early days of Drip. Some of them we found worked really well and others were complete bust and waste of time. You don’t know for another week, another month, depending on who sticks around and listens and who basically stops reading your emails or whatever other way you contact them. Curious to hear a fit, figure if it’s worth your time, and maybe 2–3 weeks I think you have a decent sense of that.

Mike: Definitely. The other thing that I’ve been looking at lately is that I’ve been testing out a new email client called Mailbird. You and I talked about this very briefly before the podcast and we decided to talk about it on the podcast. I find that most of the time I look at my email through Google Chrome and I have most of my different emails from different domains forwarded in there so that I have the one email client.

I was looking at Mailbird just because it has a unified mailbox where you can see and view all of your emails in one place regardless of what IMAP servers they’re coming from and what domains they’re coming from, et cetera, so I can see everything there. I’m not going to have to forward things over if I don’t want to but I could. I could continue doing that, but the one problem I’ve had with that is that the mail servers tend to rewrite the headers. If it’s forwarded in email, then the SPF records are no longer valid because it’s basically being rewritten. It no longer matches the original, which isn’t a big deal because I’m the one receiving them. But it still screws up the reporting staff that they get on a weekly basis about my sent emails. But you said you were assessing out something else as well. What’s that and why?

Rob: Mailbird I can’t use because I’m on a Mac. It’s Windows only. I was going to check it out, I was on the site. I straight-up Google best Mac Gmail client because I like Gmail, I like the paradigm of it, and it’s so slow in my Chrome browser now. I will go to type an email, you know that I know all the keyboard shortcuts, I’m like, “Label this as that, then type five words,” and it’s playing catch up with me. It’s getting worse and worse.

I know everyone’s thinking Superhuman, “Go use Superhuman.” Yes, I will check them out at some point, but I really wanted to consider going back to a desktop client, both for the speed and just the native feel. I found an app called Mailplane and it basically mimics the Gmail interface in a desktop wrapper in a sense. There’s also a calendar you can flip back and forth.

At first I really struggled with the fact that it wasn’t just a tab in a browser, but now I’m starting to like it. I have it on a completely separate monitor than my browser and when I click a link it opens in a browser on the other side instead of opening it in a new tab and throwing me out Gmail for not holding Command-Down and opening a new tab. I started liking the workflow. I like that all the keyboard shortcuts as the same, I label things constantly, I archive things constantly, I delete things, and I snooze or boomerang them. Those are the four most important things I do. Of course I compose and send, but those four things have to be super fast, they have to be keyboard shortcuts, and I do that both on mobile and on my desktop in essence.

The one place where it falls down is it doesn’t have the snooze keyboard shortcut, which is B, and I can’t install Boomerang on it which also has the B keyboard shortcut. I may bail on it, go back to the drawing board, and try out something like Airmail, or I know Spark’s good, or take a look at Superhuman. I struggle with wanting to do Superhuman. I think some of the hype drives me away from it and also $30 a month, obviously, I can’t afford that. I struggle to pay that or something. It’s so stupid because I’m in my inbox constantly and if it saves me any amount of time, it will pay for itself in a day.

Mike: I think it’s probably the price anchoring you have to Gmail, which has been free for 15 years now and you’re like, I don’t want to pay $30 a month for something like that.

Rob: Yeah and it’s also I know that I have to relearn or I’m expecting to relearn a bunch of keyboard shortcuts. While I can totally do that when I switched from Windows to Mac, that was a complete trucking of my productivity at the time. But I got over. It took me two, three, four weeks, and I was good.

I’m sure that if I switch to Superhuman, it will be all good. But I also want to look the product mature a little bit and see what direction it heads because every time I do this switch, I’m always wary of like, “Here they go. They got acquired and now they shut them down,” which has happened with three of the mobile email clients I’ve used, or they themselves start getting slow over time, or things go wrong with the business model and they start showing so much ads, whatever.

I know they’re charging $30 a month, so that should mean that, (a) they shouldn’t get shut down or acquired, and (b) they’re not going to do ads. All of the objections I’ve actually brought up are probably not going to happen but I often don’t trust these Silicon Valley startups in these early days because you just don’t know what’s going to happen and I don’t want my whole world to be invested in this single app that is quite disruptive to leave.

Mike: Two things here. One is I was looking at the Mailplane app website and there is something there that says flat-out that they had support Boomerang as a third-party extension, so there might be a way to basically add that into the app itself, maybe as a plugin or an extension or something like that. The other thing is that, it’s interesting that you and I are probably on the same page there where just because it’s a Silicon Valley startup and they’ve got funding, we actually put less emphasis on them being a viable product, versus the bootstrap companies where the largest company say, “Hey, I’m not going to trust you because where’s your funding? You might go out of business tomorrow,” versus I almost feel the Silicon Valley startups.

Actually, it’s the opposite. That’s just the way I view it. It seems like you feel the same way about this and I think it’s partially a function of whether or not they’re charging for their service or it’s a, “Let’s try and get as many users as we can, and try to figure out a business model to make money later.”

Rob: That’s it and since Superhuman are charging, it does remove some of those doubts, but still I’m pretty skeptical on one side. I’m like, “Yeah, you’re going to make me switch over and learn all the stuff, it’s going to make me faster, and then in six months, you’re going to do whatever. You’re going to pull a medium.” Again, anything I can think of is unlikely to happen because I was gonna say, “You’re going to pull a medium and start charging,” but they are already charging.

It just makes me skeptical that they don’t have my best interest at heart and what they have is hyper growth at heart, and they’re going to be willing to sacrifice whether it’s my user experience or whatever in order to further their business. I’m just not convinced. I’m not trying to pick on them. Just in general that’s how I view these startups. I think I will move there, eventually. That’s probably where I’ll wind up. But the fact that you just told me Boomerang is available at Mailplane, I don’t know if I have a reason to move anymore because I just click down extensions, I installed it, and it looks like it’s working. That does change the game for me. Thanks, Mike. I appreciate that.

Mike: There’s a bunch of other extensions there, too. I know you use them, so.

Rob: Yeah, but Boomerang was at the top when I went to extensions. It was literally the first on the list and I just downloaded it while you are talking, I configured it, and it’s looks like I’m all good now. It will be interesting. I like to question my assumptions and one of my assumptions is that I really want to stick with the interface. I’ve been using Gmail since 2006. Is that when it came out? I mean, I was really early on.

Mike: It came out before then because Bluetick I can see where my earliest emails were sent and received and I didn’t get into Gmail for at least a year or two. I think it came out in 2003 but my earliest emails were from 2005.

Rob: And I’m somewhere in there, 2005–2006. It’s not just I’m used to it, but the keyboard shortcuts and the actions all makes sense, and I’m very fast. It’s like using them or using an “old” editor that people move on from, but when you’re really good you can actually be in the command-line the whole time. I feel like that’s how I sync with Gmail.

Obviously, there’s an Outlook mail client or there’s a bunch of good desktop Mac clients for Gmail, but enough of the paradigms or trying to be different, and it’s not just keyboard trope. It’s just the whole interface. When you’re looking in different places for different things, I’m not sure I want to give my productivity gap much of a hit over the course of weeks or months and I’m not just sure it’s worth it to relearn a new tool.

Mike: That’s actually what attracts me to Mailbird was because all of the keyboard shortcuts were the same as Gmail. It’s just like, “Oh, I can just hit the V or…” I honestly don’t remember what the shortcuts are. I just do them at this point, but adding a label to something, or moving it, or throwing it to the trash, those things are just keyboard shortcuts that I just use. I think one of them is Control-Pound or Shift-Pound or something like that, and there’s one, it’s a V and add a label to it and move, and all that stuff. It’s just there and it’s very intuitive, very much alike. Not intuitive because shortcuts are not intuitive, but once you learn them, they just become second nature. For the most part, the ones that I use are there and it’s helpful.

The only thing I don’t like is that in Gmail I have have stars in emails and then I have one’s that are marked important and then ones that basically everything else below that. I have three different sections and it doesn’t have that. It only has two. So, it’s like, “Oh, well.” I mean, I’ll live. It’s not like I’m going to stop using it because of that. It was cheap, so.

Rob: Yeah and it’s just keyboard shortcuts. I’m sure Superhuman probably duplicated the Gmail ones, but there’s other things. A little known fact, actually, Mike. Before I started Drip, I was actually pretty heavily considering building a mobile email client that was all the things. It was fast and there’s some add-on. I remember you and I talked about it. I was like,“Yeah, this is on my list,” and you’re like, “Boy, that’s kind of a Silicon Valley play.” You’re like, “How are you going to make money at that?” and I was like, “Yeah, that’s what I’m struggling with because it’s not a normal SaaS model.”

I thought for a bit of why I should do basically a SaaS email client and again, make it fast and make it do all the things, build on top of Gmail in a way that they’re not innovating on, and I thought to myself no one would pay for that. They wouldn’t pay a price. I don’t want to charge $5 a month. What’s funny is, I think that was my bias because I don’t want to pay for an email client, but also, it was 2012 and I don’t think Gmail had the problems that it has today with the slowness and all that. It didn’t have that problem in 2012.

I think timing is also a factor. It’s not just that I have the idea, but you also need to be there at the right time and you need to execute on it. The Superhuman guys has done a great job, as we’ve heard years of customer development in essence to get to where they are today, and that was obviously a ton of work to get there. It’s not just, “Oh, you had the same idea and the Superhuman guys did it.” They did a really good job of it, executed to perfection.

Mike: That’s actually a very odd coincidence that you mentioned those specific things about the speed because I think it was about two years before that that they had acquired the business that your co-founder in TinySeed, Einar has. He was building and it was to make mobile search very fast. Then fast forward a couple of years and the search is no longer dog slow.

Rob: Yeah, it’s a trip. You wonder if Gmail, in the background, are they’re innovating and they’re going to basically release something that’s going to makes them superfast and that implement some of the things Superhuman does. That’s the other thing. Since it’s on top of G Suite or Gmail, they have platform risk right now. As an idea like Gmail or Google could feasibly shut them down. It would be a bad move or an anti-competitive move, but we’ve seen this happen with Twitter API restrictions and all that stuff. Facebook do that, wouldn’t put a pass Google and it could be a pretty big issue for Superhuman moving forward if they become a multi-million dollar business, deck a million dollar business. Who’s to say Gmail won’t either just implement the features and it’s still free or screw around with API access and that kind of stuff?

Mike: It’s funny you mentioned that because I’ve actually been going through a bunch of approval processes with Google. I don’t know if I talked about this before, but because I’m accessing customer information through OAuth, I had to go through this approval process and they say…

Rob: You did talk about it. A couple of episodes ago you mentioned it’s pretty cumbersome.

Mike: And I’m still going through that. I’ve sent them a bunch more information and I’m just waiting now to see if anything else that they need and I haven’t heard anything back for at least a week or two. That’s certainly something that could happen, but it’s more of a result of me just accessing things through IMAP. I don’t know how they actually access that data but if it’s through IMAP, then there’s got to be a reasonable way to get access to it because there’s no way I could see that Google could say, “Look, nobody can access through IMAP anymore. You have to use OAuth tokens and et cetera. I suppose I could end-of-life that access down the road but they’re going to have to wait while people, their email clients switch over and add that type of support.

Rob: And that concludes this episode of Gmail Clients for the Rest of Us. That was a longer tangent that I thought we would go on, but I think it’s still interesting stuff. We touched on a couple of relevant points of platform risk, about finding the right client, because if you’re in it so many hours of the day, it’s important stuff, and then switching cost and that kind of stuff.

Mike: With all that said, I think we’ll switch over and actually start doing some of these listener questions that we get them in before the end of this episode. The first one comes from Steven Moon. It came into Twitter and he said, “With so many years of experience behind you, both in the startup space, what would you say were some of your biggest regrets?”

Rob: This is a tough one. I gave it some thought in advance of the episode because it’s not something I think about that much. I tend to make pretty calculated decisions, I tend take longer to makes decisions than some people, and I try to make it with all the information I have at the time. If I make a decision with that and it turns out to have a negative outcome, I don’t consider it a regret because I did what I thought was best at the time. I don’t make many impulsive decisions. Those are the decisions that I would tend to regret, are things that I didn’t take the time to think it through or made an emotional decision instead of trying to look at the data and making the best decision.

With that said, I think that something that I regret early on—this is 2005, maybe 2010—is that I was too timid. I was scared of making people mad. I was too much of a developer to do marketing. That transition actually happened during that time period, but in the early days, even before 2005, I didn’t want to market because I considered it some bad thing. SEO, AdWords, taking out ads. I don’t know adjusting to all that and even doing sales. It wasn’t something that I really wanted to do and I wished that I’ve gotten there sooner. Eventually, I realized, “Oh, this is valuable. A fun product provides value, reaching to people, for who it’s going to have value for, is an important thing.”

I think another thing that I regret is I thought that I could do everything myself early on. Frankly, I did everything myself for a while and then I hit the ceiling on that. Then I hired contractors and VAs, which worked to a point. I guess I don’t have regrets that I did that, but then eventually knowing that I needed a deeper network of people, has changed my world and allows me to do things a lot faster and a lot easier than just trying to go it on my own. These are lessons I’ve learned along the way and I guess my regret is I didn’t learn earlier. I think those tend to be my regrets. I have another one but how about you? You want to weigh in on something?

Mike: I think some of mine are similar to yours. Essentially, they were learning experiences and the one that definitely comes to mind is not really thinking through things before just doing them. I wouldn’t say that I was unnecessarily impulsive in many ways, but I would definitely say that I didn’t pause to look at the big picture enough.

For example, when I was in college, I did not do very well. Even going back into high school, I did very well in high school because it was high school and it was easy to make. But unfortunately, the by-product of that was I didn’t know how to learn things. I either figured it out and just did whatever needed to be done or I just said, “I’ll be able to figure this out.”

What tend to happen is I leave things to the last minute because I want to do other stuff and I wouldn’t spend the time to focus on my studies or actually really trying to understand stuff. It’s either I could do the problems or I couldn’t. I feel like I didn’t have a good understanding of how I learned when I got to college and I really struggled when I got to college because of that, because I relied on me just showing up and being in class to understand stuff. When I didn’t, I had a hard time sitting down and actually doing homework or studying because that was just not how I had wired myself.

That took a really long time to break. It took four or five years to break that habit. I fortunately did when by the time I got to grad school but it took way longer than it really should have. It was because I didn’t think about the longer term consequences of what those actions could potentially be but I didn’t necessarily know what those consequences would be, either.

Rob: Right because you’re 17. I think he was asking in terms of startups. How does that relate to your business? Your professional career? Or does it?

Mike: It does. I have to intentionally set aside time to think about the bigger picture and if I don’t, I could easily find myself just going down the rabbit hole and not thinking about, “Is this the right thing I should be doing? Is this the most important stuff for me to be spending my time on?” I can easily burn a lot of time doing stuff that actually doesn’t move the needle or isn’t very important if I’m not very cautious and conscious of that.

It’s more of being aware that that’s a flaw of mine that I have to keep in mind and being very intentional about setting aside time to come up and look at the big picture. If you look back in my day with AutoShark, that was a huge problem because I just put my head down and kept going. What I really should have done was take a few steps back and look at the bigger picture and be a little bit more objective about stuff.

Rob: That makes sense and knowing that’s your previous position, you should ask yourself that now, what it would look like to take a step back? It’s a rhetorical question but that’s the thing about knowing our strengths and weaknesses is now that I’m older, I know a lot of my weaknesses. I don’t know that I know them all but I really tune in when I start the same things that I realize, or maybe not 100% true, or just an emotional thought, or me just trying to justify what I feel like I want to do, rather than what should be done, and those are weaknesses.

Or when I am a negative self-talker. I talked before if I don’t get enough sleep, I’m super negative and I’m almost look like someone who’s depressed. I’m unmotivated for that day. I’m unmotivated and I’ll just be like, “Nothing’s going to work. This whole thing isn’t even going to work. Why are we even doing this?” I literally have that in my head and I will always say like, “Dude, this is a temporary thing. You’re just in a weird state. Go take a nap.” I’ll come back and I feel better about it, but I didn’t realize that until five or ten years ago. I think that that’s an important thing, to know yourself.

Mike: The way that I deal with it now is I do a lot of journaling and I use that to track whether or not I’m making progress on stuff or getting things done that I need to get done because I will write those things down, but again, that’s just a personal productivity hack more than anything else of make sure that I’m staying aware of those things.

I would say that the other major regret I have, I’m not sure if I label it as a regret but being under the belief or assumption that I would be youthful forever. I definitely found that as I’ve gotten older, things do not heal nearly as quickly as they used to, I need more sleep that I used to, and just a lot of stuff with my personal health that I was like, “Oh, I’m invincible. I’m twenty-something years old and nothing will ever happen to me.” Fast forward 10 or 15 years and your body starts to give out on you in certain ways and you’re like, “Huh, that sucks,” and there’s nothing you can do about it.

Rob: That makes sense. The other regret I can think of is that I didn’t take good enough care of myself while growing Drip. There’s self-care. What’s funny is it’s what my life talks about all the time. That’s what ZenFounder is, about taking care of yourself. There’s a certain point where I was just bearing the burden of a lot of stuff. I wasn’t working on the things I liked but I knew they had to get done and it’s that recipe for burnout where I’m capable of doing them but they don’t bring me joy and I didn’t want to interrupt anybody else’s day because everybody else was either selling or onboarding or writing code and that’s what’s needed to push the business forward.

If I pulled anyone else into it, this is a fallacy. You tell yourself like, “I’m just going to grind it out. The business is going fast, everything’s working. Why would I screw that up, pull people off, and move slower than these other things?” Anytime I got budget, I hired a support person or a developer or someone else to move the business forward and really should have made some different decisions there.

I didn’t take good enough care of myself, I did start to enter burnout at a certain point, and that sucks. There were a few times in my professional career and the most recent one was during Drip. I think I want to avoid it for the rest if possible, because it takes toll on you and your relationships is the problem. You can recover but if you’ve damaged relationships, it takes a while to repair those.

Mike: Moving on to our second question. This one comes from Dick Polipnick and he says, “What do you think of buying a small company that already serves your target customers and building your SaaS idea on top of it?”

Rob: He’s saying buying a small company that is not a SaaS company, right? It’s either one-time download software or it’s an info product? What do you think he’s implying here?

Mike: I think it could be either one of those. It could also be a services business of some kind? I wouldn’t say it’s as big as an agency. I think the implication here is it’s a small company that’s probably one person or maybe it’s just a book or something like that. That seems odd. I don’t think that’s it, actually.

Rob: If it’s a small consulting agency, I wouldn’t buy an agency unless I wanted to do agency work. Going from agency to product, the work is hard. Ask anyone who’s trying to do it because you have so many things going on. It’s a well-worn story. It’s possible, but it’s a slog. I would not invest money into acquiring an agency. If it’s like an ebook or a one-time downloadable software and there was an audience there that you felt like could buy a SaaS or would be interested in something that’s pretty a direct path to it, I’m not opposed to the idea of it.

The concern I have is, if you spend this money—let’s say it’s $30,000, $50,000, $100,000, it’s a chunk of change—then what if you’re wrong? What if now you have this info product that you don’t really want to run or you have this one-time download software that you don’t really want to maintain and they don’t really want the SaaS? You can’t ask them now because you don’t have access to the audience.

I’m not saying don’t do it, but I’m saying how can you prove that I bought this or disprove that hypothesis without spending the money? Can you work with the current owner to survey the audience to find out if they do want the SaaS? Or maybe you do? Maybe if it’s a one-time software and you buy it, and the SaaS doesn’t work out, you’re okay with that. One-time software is not terrible. I mean, I had done it, it was for years, and it was a great revenue stream.

So, I’m not opposed to it but I do feel like you have to answer a lot of questions. Even if you answer, I would ask, “It’s like acquiring yourself into the stair step?” which is something that I did and very few people do, but I didn’t intend to build SaaS on top of the things I acquired. Those were really just income revenue streams. So, not opposed to it, but I do have some questions that I want answered before doing it.

Mike: I think the piece that’s probably the most important is how you validate that is the right move and that those people are going to want to purchase a SaaS? If there’s already people who are purchasing the SaaS products in that particular target market that is similar to what it is that you want to build, then great. Are you buying it because of the company and what it offers? Or you buying it because you want to plug it in and you see it as a new channel that you can tap into because they’re offering something that nobody else does in this particular market?

So, thanks for the question. The next one that we have is from Daniel Fellows and he says, “Question for you. How do you deal with the loneliness of building your startup?

Rob: I think that’s the reason I started my blog back in 2005 was the loneliness of trying to do something that I didn’t know if anyone else was doing it. I didn’t know if any other single founder software startups that were raising funding. There was nobody.

I starting blogging and trying to find other people. That turned into my book, then this podcast, MicroConf, so I deal with the loneliness by having this community. Whether I have been part of building it like we have been or whether I just became a part of it later, I rely on this community as much as anyone to keep me from feeling that loneliness. That is a reason.

We did the podcast for a number of reasons, but I think part of it is to be able to talk about this stuff, both with you and with the audience, and to get questions and comments and all that stuff is helpful.

Going to MicroConf basically three times a year in essence is a big one for me and I always get a bump from there, realizing that there’s a bunch of other people doing this with us. On their own but with us. And then of course, Mastermind groups. That’s been a huge thing. I have always been a proponent of it years and years. That gives you that touch point every other week or however often your do it, to know that there are people that are in your corner.

I didn’t do this when I was growing startups because I was so focused on grinding out day to day, but finding founders, entrepreneurs locally, Sherry’s been doing a good job of that here in Minneapolis of finding local entrepreneurs and having them over for dinner once a month. We’ll just get two couples over here and have a nice dinner. Sometimes the conversation involves work and other times it doesn’t, but having that shared ethos of being a founder makes conversation super interesting and cool. How about you?

Mike: I agree with everything you said. The one other thing that I would add is finding something that is outside of your business where you can use to socialize with other people that is not work- or business-related. I think that’s something that I definitely neglected that early on in my career where it’s just I worked all the time and beyond that I didn’t do much else.

I didn’t really have a life outside of the business and I think that’s probably, I wouldn’t say a huge regret but it’s definitely something that I probably should have done a little differently if I were really thinking about it or thinking about the future. I think I’m definitely on the right track there these days, but it’s something that I would probably emphasize a lot more if I were to go back and do things over again.

I feel like having time away from your business when you’re not thinking about it and you’re not talking to people who are also running their own businesses as helpful just as a way to recharge. If you’re spending all of your time thinking about it, it starts to creep into places where it really shouldn’t, like when you try to sleep at night and you toss and turn just because you’ve got business on your mind at all times.

There are always interesting problems but it’s helpful to have something else that is completely distracting and completely irrelevant to your business that you can do that will take your mind off of it. I find a lot of times that there are problems that I’m working on where the solutions just come to me very quickly if I’m not thinking about it.

Rob: It’s a good point. It’s something I didn’t do until the last 2–3 years actually. I believe I was doing some tabletop gaming before that, but before the exit in 2016, that I really ramped it up after that. That’s something that I’ve enjoyed having as a hobby. I really neglected my hobbies for a decade plus and I don’t regret that actually and wished that I have done more hobbies because I did take that time and I got stuff done.

The reason I was able to put out as much content as I did and we’re into all the multiple things as I was thinking about them a lot. Eventually, that can take a toll on you. I think having maybe one hobby that’s not super time-consuming can be helpful. But since I didn’t do it, that’s not something I can necessarily recommend. I know it’s best practice, but I think the other stuff we’ve talked about with masterminds and such is that’s what I did, so that’s what I feel better about telling people with a straight face. Not to just do what I say now as I do, but you can do it as I do and I think just to keep from being lonely.

Mike: For our last question of the day, we’re going to take one from Graham Blake and he says, “As a single founder whose business has succeeded, I find I have less time to do the things that made it succeed. I delegated a fair bit but the management of a bunch of small areas reduces the time I have to deep dive on stuff. How do you organize things? You can still do the most valuable work while keeping the machine running smoothly. My biggest difficulties are that most of my valuable work involves deep focus, which is generally writing a video production. I have to give feedback on work that is being done for me, but if I ignore this for too long, it creates bottlenecks.”

Rob: This is a hard one. It’s the maker’s schedule versus the manager’s schedule from Paul Graham’s writings where the manager is interruptive, you’re responding, you’re trying to keep people going, and the maker is where you need deep focus. Trying to be both of those is very hard. I don’t know that there’s a great answer to it other than to hire someone to manage all the little ins and outs so that you are no longer a manager. Trying to be both is hard.

There’s really two solutions here. Step away from the making, hire somebody to do that, or step away from the managing and hire someone to do that. I realize neither of those is easy nor straightforward, but we’re entrepreneurs and we do things that are not easy or straightforward. That’s what I would look to do longer term if I look out six months or a year, I would look to get completely out of one of those or the other and you need to ask yourself which one you want to do.

We’re bootstrappers. You can do what it is that you want to do. That’s why we design these businesses around us and then figure out a path to get there. It may not be hire one person to manage everyone right from the start. Maybe it’s someone with enough skill that they can manage part of your team, part of the contractors or whatever. But you need to remove yourself from the deep dive if you don’t want to be doing that or you need to allow yourself to deep dive if you want to.

Mike: I think it’s really hard to cross that line because there’s a chasm between what you’re looking for from people versus what you’re actually getting. Until you get to a certain scale, it’s hard to put people in there if you can’t afford to hire managers, for example. I think that getting to the point where you’ve gone one direction or the other is the difficult choice the most people have in front of them.

I’m sure you’ve run into this in the past where you’ve got something that you’ve outsourced to someone and then they come back with it, but you still need to spend time going through it and looking at it, making sure everything’s right. Really, the only short-term solution I see for that is time-blocking in some way, shape, or form so that you are not trying to do too much context switching between the creative time versus that management time.

If you try to slot it in on a daily basis, it’s just not going to work. I’ve found that if I allocate time for it once or twice a week or something like that, maybe Tuesdays and Fridays or something along those lines, you can get more done because you’re not context-switching between those things as much. Anything else that comes up, you have to be diligent about making sure that those questions don’t come into a channel where it’s going to be disruptive to you.

I was constantly telling people, “Hey, don’t send me a Slack message. Send me an email and I will review it when I get it. Otherwise, that Slack message is going to be disruptive for me. It’s going to screw up my schedule of being able to work on this stuff.” You just have to be diligent about making sure that the expectations are that you will review stuff on Friday and you’ll go over it with them on Tuesday, for example. That way, you can email them, say, “This is what my thinking is,” or, “Here’s a short video of what my thoughts are.”

Got something else I would rather recommend is trying to cut down on the synchronize time that you have to spend with people. If you can do a short recording of it and send it to them as feedback versus getting on a call with them so you both have to be available. I find that calls tend to be disruptive just because if it’s 20 minutes or half an hour before the call, you’re really hesitant to start on anything that has any level of involvement because you know you’ve got a call coming up and you don’t want to have to stop. It’s about being conscious of where you’re time is going to be wasted and these are going to waste half an hour of your time before and after the call.

Rob: Those are all good points and I really want to highlight the one of just changing the expectation of communication and saying, “By default, use email because it asynchronous. By default, let’s not schedule calls. Maybe use Voxer where we can leave a voicemail and go back-and-forth on that, then turn off alerts, and check it twice a day or something. But if stuff is urgent, then you can text me or Slack me and interrupt me. If it’s super urgent, you are blocked, and you need an answer within, let’s say 10 or 15 minutes, then use an interruptive medium. But if not, don’t. Just use Slack for everything.”

That’s always when I would onboard new people. Anytime, actually, with TinySeed, with Drip, with whatever, that’s my thing. It’s like, “Let’s not Slack by default. This is dumb. Let’s not text by default. I don’t need to be interrupted and you’re interrupting what I’m trying to do.” That could be a first step. We just don’t know if it seems using Slack for everything is just throwing them into a loop, or you can say, “Hey, everybody. I’m going D&D. Do not disturb for the next two hours. I will not get back to you. If the building is burning down and the site is completely down, then break my D&D. Otherwise, do not expect a response.”

Frankly, if you’re a software video production company, that should be the default. I think two or three hours every morning, two or three hours every afternoon, everyone should be doing that. Now, that doesn’t work if you’re a manager and you have blah-blah-blah. Yeah, I get it. But that should be the default and you should be able to break that rule if you have a specific role, or if you have a specific week, or you need a lot of collaboration or whatever.

I can’t believe my voice at a certain point that I thought was not going to make it through this episode, but I’m glad you were talking at points because it gave me a chance to recharge it. I’m feeling good. We answered a bunch of listener questions today.

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