Episode 307 | Is the Micropreneur Dream Still Alive?

Show Notes

In this episode of Startups For The Rest Of Us, Rob and Mike inspired by a listener question, talk about whether or not the Micropreneur dream is still alive. Some of the topics discussed include reasons to start a business, stages of micropreneurship, and legacy.

Items mentioned in this episode:


Mike [00:00:00]: In this episode of “Startups for the Rest of Us,” Rob and I are going to answer the question “Is the micropreneur dream still alive?” This is “Startups for the Rest of Us,” episode 307.

[Theme music]

Mike [00:00:16]: 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 built your first product, or you’re just thinking about it. I’m Mike –

Rob [00:00:25]: And I’m Rob.

Mike [00:00:26]: – and we’re here to share our experiences to help you avoid the same mistakes we’ve made. What’s the word this week, Rob?

Rob [00:00:30]: Doing pretty good. I think we’re getting ready to send some emails to the MicroConf mailing list here in the next few weeks, because we’ve settled on the dates for MicroConf Vegas next April. If you’re interested in joining us and a few hundred of your closest founder friends in Las Vegas for, either MicroConf or MicroConf Starter Edition, head over to microconf.com and add your email address to our list, and we’ll let you know as soon as tickets are available.

Mike [00:00:55]: Are you saying we’ve actually planned something a little bit in advance?

Rob [00:00:57]: [Laughs] Once every two or three years we do this, and I think we might be ahead of the game on this one – although as I’m saying that, I’m realizing there’s still time for us to slack and get behind the eightball like we usually are.

Mike [00:01:08]: Yeah, cool. I talked a little about it a little bit this past week, about some of the changes that I was testing out for Blue Tick, and hit a couple of snags here and there mostly due to various RFC issues where they’re not real clear about stuff, or they imply things that are just absolutely not true. So, I’ve had to work through some of those, but the testing’s gone really, really well so far. I have a internal launch date that I’m shooting for at the moment, but I need to do a little bit more planning on that before I can commit to that actual date. I have a date in mind. I just want to go through all the lists of things that really need to be done before I can publicly call it out and say, “This is going to be the date.”

Rob [00:01:42]: Is this update just an internal rewrite, or does it add new functionality to Blue Tick?

Mike [00:01:46]: It adds new functionality. It allows you to see all the different emails that have been sent and received regardless of whether they were sent through Blue Tick or not, so when you add in a contact you basically just put in the email address of somebody that you want to add to the system. What it does is it matches that email address up to all the emails that you have sent or received from that person historically, even before you signed up for Blue Tick, and then it will be able to show those to you directly inside of the app. It’s a nice way of being able to mind your mailbox and identify people that you’ve started conversations with, and then they didn’t get back to you, and then – for whatever reason – you forgot about them. The app will have the ability to show those things to you.

Rob [00:02:24]: Cool. Given this, do you have a public launch date? At this point, you’re basically in early access right now, right? You’re getting your folks who’ve pre-purchased from you into the app and honing that and everything. Do you feel like your launch date is within reach?

Mike [00:02:37]: That’s what I’m still trying to sort out. I’ve got a list of all the things that need to be done, and I’m trying to figure out a time estimate for each of those. I know in my mind, “This is the date that I want to hit,” and I’ve got the list of things that need to be done, but I don’t have all the time estimates for all those things matched up and added up so that I can say, “Is this actually reasonable to be able to hit that date or not?” That’s what I’m working on right now, and that’s what the next step is.

Rob [00:03:00]: Mike and I really want to congratulate Glenn Germaine of My Practice. Glenn is a several-time MicroConf attendee. He’s come to MicroConf in Vegas with his wife. They fly up from Australia. He’s also written into the podcast several times, and has just been a supporter, and we’ve really appreciated our dealings and interactions with Glenn. His company was acquired by Best Practice Software, and he actually tweeted it out. He said, “Shout out to all our MicroConf buddies, particularly Rob Walling, [Single?] founder, for the years of advice.” He linked over to the press release, and so we have just a big “congratulations.” It’s such a big step to get to that point. He really grew My Practice on his own, boot-strapped it, and grew it to several employees, if I recall. Didn’t he have ten, 15 employees? That’s a big deal, to be able to exit that. We wish you the best, Glenn, moving forward.

Mike [00:03:45]: Yeah, and Glenn’s been coming to MicroConf since 2012, so it’s definitely been a long-time listener.

Rob [00:03:51]: Yeah, very cool.

Mike [00:03:52]: Yeah, congratulations, Glenn.

Rob [00:03:53]: What are we talking about today?

Mike [00:03:54]: Well, today what we’re going to be talking about is, “Is the micropreneur dream still alive?” This is inspired by a listener email from Scott Underwood. I’ll paraphrase some of the things that he said, but some of the different pieces he went into were the fact that, Rob, you just recently announced the sale of Drip a few months ago to Lead Pages, and it ties into Glenn Germaine’s announcement that he’d sold My Practice and is presumably going to be joining them for a while. Another announcement that came out recently was Patrick McKenzie announced that he was selling Appointment Reminder and, in addition to selling Appointment Reminder, should move on to other things. One of the things he’s doing is moving on to join Stripe as a full-time employee.

[00:04:31] Scott wrote to us and said, “I sent Patrick a quick congratulations email just before he broke the news, but it felt like the day the music died. My heroes are giving up on the dream I’m chasing and going back to being employees. Life’s a journey, a transition, growing families, etc., so priorities change. The Startups for the Rest of Us troops might need a little rally that the dream is still alive and attainable for those of chasing it. Thanks again for all the advice and entertainment over the years. Looking forward to more.”

[00:04:50] A couple of things I wanted to call out in this email snippet that I read out was that, I agree, priorities definitely change over time. But I think if you look at the three stories that I mentioned earlier, with Rob and Glenn and Patrick, the fact of the matter is that all three of these stories – if you look at them very objectively – they are success stories. All three of these were built from the ground up. They were built from nothing and were sold to the betterment of the founder. I think that if you look around at the general, broader community of people who are boot-strapping companies and building them, you can trice that back to MicroConf. You can see that MicroConf tends to sell out very quickly, and it’s aimed directly at this particular audience.

[00:05:30] So, you have to ask a couple of questions. The first one is: Are they pursuing something that’s ultimately going to put them back in the same position that they were in, which is working for somebody else? The second one is: Are they all delusional? The answer to that is, probably not, and I’m hoping it’s [laughs] really not. Certainly for some small segment of them, yeah, there’re some delusions of grandeur, but the reality is that people start businesses for a wide variety of reasons.

Rob [00:05:53]: Yeah. First off, thanks to Scott for sending that. I think it’s an interesting sentiment. I certainly thought it before I sold DRIP. It definitely crossed my mind, “What will people think?” That wasn’t a driving factor in the decision either way, but I did wonder how that would feel, and it’s interesting that there has been quite a bit of transition recently, and I bet just beyond Glenn and Patrick and myself, I bet there’re other folks here. I know there’s a lot of folks selling their aps and moving on to other things.

I think the thing to think about is – I don’t want to speak for Patrick or Glenn – but for me specifically, the micropreneur dream was to not work for someone else in a capacity that I didn’t enjoy, and to be stuck with that until I retired. These are the things. I didn’t work till I was 65 for someone, just trying to cram money into a 401(k) and just eke by and do the 9 to 5 and work my way up the corporate ladder. If you get fired or you leave that company, maybe you can do a lateral move. Maybe you won’t have as much trust. It’s kind of the rat race, right? I didn’t want to do that, and I didn’t want to work till I was 65.

[00:06:52]: So, while you can say at this point in time, this snapshot, “Yes, Rob now works for someone else again.” – something I haven’t done for about eight or nine years, I think, since I’ve been an employee at another company. But I ask myself: a, am I forced to do this until I’m 65? The answer is no, and that’s based on the financial means that happen from the exits and other things that I’ve had. The other thing is I’m working very much in a capacity that I really, really enjoy. I’m given this creative freedom. I could go into the specifics of it later, but I’m basically a product person. I’m doing what I was doing on DRIP anyways, but with a lot less headache and little to no – or, a lot less, I’ll say – financial risk. When you’re running your own company, you’re waiting to get just swatted by your competition, or to run out of funding, or to run out of money, or whatever, and that’s gone.

[00:07:38] So, I’ll just preface that by saying the fact that currently at this point in time I work for another company, given how different it is – so ten years ago, the last job I had, compared to now, it’s just night and day. I was basically a programmer just slogging away in a corporate environment. What I’m doing today is night and day, and I owe that to my entrepreneurship, and to the micropreneur journey. So when it’s like; Is the dream still alive? It’s like : Yes, it changed my life completely. Night and day. If I had not done that I would be in a completely different situation, with a completely different outlook and, again, I’d be slogging away, putting a couple hundred bucks a month into a 401(k), counting the days until I could retire and be in control of my own time. So, that’s kind of my initial thoughts, and we’re going to now dig into all matters of thinking through what this looks like.

Mike [00:08:23]: A couple of points that you made there which fed off the initial point, which was people start their business for a wide range of reasons. Some of these reasons are negative, and that’s because they want to move away from something. Then there’s other reasons why someone would start a business which have a more positive slant to them. They want to move toward something. Just to illustrate a couple of those examples, somebody might hate their job, or they hate their boss. There’re definitely reasons to start your own reason that have that negative slant. It’s because you’re trying to move away from a current situation. Rob just talked about the fact that he didn’t like his job. He was sitting there slogging away as a programmer, didn’t enjoy it. Those are the types of things that somebody would say, “I don’t like this. I either want to find a new job.” and that’s what the vast majority of people do. The other option is to start your own business to create a job that gets you away from that.

Then there’s the flip side of that, those things that you’re trying to move towards. It’s not to say that there’s only one reason to start the business. A lot of times these things factor into each other, and there are multiple things at play. You might want more money, or you might want some sort of financial independence. You might want to travel. You might want more time available to work on your hobbies, or spend with your family. Those are the ones that I talked about that have a much more positive slant to them. You’re moving towards something. Those are goals that you’re trying to achieve.

Rob [00:09:37]: Everything you have in this list are things that – these were goals that I wanted to achieve by getting out of just the salary employment of being just a 9 to 5 developer. So, I think this is really poignant, and I bet these things resonate, I would bet, with the majority, if not all, of our audience. The thing is I achieved all of these. Within a few years of even DotNet invoice, and in the early days, pre HitTail – these are all these little $2,000, $3,000, $4,000 apps. I hated my job, so I quit it. I hated my – I didn’t hate my boss – but I didn’t enjoy working for other people, so I left that. I did have a little more money. I definitely had time to travel, and I definitely had more time with my family.

[00:10:14] Then things change, right? Two years later, I personally got a little restless and got a little bored and wanted to have more impact on the world and do more interesting things, and working the four-hour work week wasn’t as interesting after a couple years. But it was amazing for the couple years that I did it. So I think that’s something to keep in mind. I don’t think you’re going to find your end state and be like, “Now I’m here, and I’m a micropreneur, and I’m independent, and I’m done for life.” None of us have done that. You look at Patrick McKenzie’s journey. You look at Jason Cohen’s journey. You look at my journey. Just everybody continues to evolve, because we’re entrepreneurs, and we’re ambitious, and we’re curious, and we need to constantly be learning. That means you have to do new things, and often those new things have to be bigger and scarier challenges, and oftentimes that may not look like you think it’s going to look. It may not look like raising a round and starting a big company. Maybe it means exiting your company and working for someone else to see if you can have an impact.

Mike [00:11:06]: That just kind of illustrates that the reasons that people exit their businesses is just as varied as the reasons that people start them, and some of those reasons overlap. For example, if you want more money and you want more financial independence, one of the ways to get that is to sell your company, to essentially get rid of all the responsibilities and the things that go along with it and essentially give yourself a financial reward for that that allows you to go do other things. The reasons you start the business can overlap very much with the reasons that you exit it.

[00:11:37] Now, I think that the biggest question to ask out of all of this is, “What is the end game for you?” I don’t think that there’s any right or wrong answer here that’s generally applicable to everyone, but it ties back to the classic “Rich versus King” argument. There’s two different variations of this. One of them comes from an article – we’ll link both of these in the show notes – but one of them comes from Noam Wasserman, who is a – I forget whether he’s at Harvard or MIT, but he’s a professor there who teaches about entrepreneurship. He talked about the idea of “Rich versus King” being a founder’s dilemma where you are trying to decide whether or not you’re going to take external funding. Are you going to try and build a business and make it huge and be rich because of it, or do you just want to grow it to the point where you are king of that particular industry, but you don’t necessarily don’t have a ton of money, because you didn’t take all the money, and you didn’t take any of it off the table.

[00:12:29] There’s another one a year after that, in 2009, by Jason Cohen, who talks about this particular dilemma as it relates from the standpoint of selling a company. Do you want to build a company and just run it as a lifestyle business – and “lifestyle” in air quotes, because Oprah’s got a lifestyle business, and she has quite a lot of money [laughs]. There’s different ways to look at that, but the idea is that you want to own that without giving up any ownership. That is your identity. You see it as an extension of yourself. The flipside of that is taking funding, going big – which may or may not work out – but it’s a risk. All these are about tradeoffs, about whether or not you’re going to take that external funding, give up some control. Again, it’s the classic rich versus king argument for that.

Rob [00:13:09]: Yeah, and the thing to keep in mind is as you go through this journey – I mean, I already touched on it for myself – but this journey of entrepreneurship is just that. It’s a journey. It’s a path, and your perspective is going to change. Whether you get married, whether you have kids, whether you start to travel, you’re just going to – that’s all going to shift you. It’s going to shift your priorities and your focus and the thing that you really, really value the most. To be honest, your current situation is going to heavily serve to shape your motivations. So, if you think about how things are going to change over time, let’s throw out some stages of entrepreneurship where step 1 is like, “Well, I hate my job. What can I do?” You go, and you find MicroConf, or you find this podcast, or one that – Justin Jackson, or Patrick McKenzie, or just somebody, and you follow them, and you figure out, “Oh, this is actually possible.” Right? Then maybe you validate an idea, and step two is building an idea, and three is launching, and four might be some growth.

[00:14:03] The, after that – let’s say you’ve quit your job at that point – what is the endgame? What is step five? Is it to just die with the most money? Is it to just sock money away? Is it to have freedom? Put yourself in the shoes of someone who has come from exactly where you are, and you’re working a salary job, and in your mind just getting out of that salary job is it, and you feel like you’d be happy for the rest of your life. That’s not what happens. Over and over, we see that it’s really good to have that motivation – for it to be strong – but once you get out of that salary job, you’re going to be super-happy for, I’ll say, a year or two, maybe three, depending on your disposition. Then you’re going to get restless, and you’re going to start thinking about, “What else could I be doing? This person over here’s doing something interesting. Maybe I should launch another product.”

[00:14:45] Or, you could perhaps even feel instability in your revenue. When I had HitTail at a certain point and Google tried to kill it two or three times accidentally, I suddenly realized, “Boy, I could lose my whole micropreneur dream that I have going right now overnight if Google decided to just nuke all the key words,” or whatever. So, certain things come up that then start making you think about, “What is next?” “What is next?” I think being in a steady state of just making eight grand a month, just enough to live, and trying to do that for 20 or 30 years – I don’t think any of us are going to be happy with that, and I don’t know how particularly stable that is. So, you have to start thinking about that. What is next? Is it to go bigger, or is it to diversify your revenue? Is it just to enjoy a few years of super-relaxed time and then think about what’s next? There’s a lot of thought that goes into this.

[00:15:30]: And you don’t need to think about that until you get there, to be honest. If you still are in a salary job and you don’t like it, your number one goal should be to get out of that. It should be to make enough money to get out of that. Once you get there, enjoy it. Live it up, and then when you do get bored, just think back to this episode and come re-listen to it. It really does come back to the arrival fallacy, right? You’re going to think that you will have arrived once you’re free from the 9 to 5, but it’s a fallacy. That doesn’t mean you shouldn’t do it, because it’s awesome to enjoy it for the time that it’s going to keep you happy – and that will be, like I said, one, two, three years, depending on your personality. Then you’re going to look at the next thing, and that’s how we grow as humans. We evolve over time.

Mike [00:16:06]: Yeah, I think the point of all that is even after you have, quote-unquote “arrived,” your life is still going to continue after that, so you still have to find things that are going to be interesting. Relating back to what you’ve said about the different stages of the micropreneurship, and the fact that your current situation is going to shape what your motivations are, in the early stages your focus is much more on yourself and your own needs : What are the needs of you and your immediate family, so that you can pay the bills and keep a roof over your head? Then it extends past that, and as you grow the business you extend that. It extends out to your family, or friends, or your co-workers, or employees. It extends out to your customers, and eventually to different parts of the region that you live, or the country, or the world that you want to have an impact. Over time, that impact is going to grow. The question becomes: How far is your reach? How much of an impact are you making?

[00:16:59] The goal of entrepreneurship is really to make an impact in whatever way is most appropriate for you. That question you need to answer for yourself is what do you want to have an impact on? I think I saw on Twitter Michael Pryor, who is the CEO of Fog Creek, had tweeted over to Patrick McKenzie – after he announced that he was going to be going to Stripe – and he said, “This is the perfect place for you to maximize your effective output on the world.” I think that’s a very poignant quote because of the fact that Patrick McKenzie is in a position where he probably doesn’t necessarily have to work for anyone else. But what is ultimately going to make him happy? He could go back to consulting. It didn’t seem to me like he particularly cared for that, although he could make a very successful career out of that if he wanted to.

[00:17:42] But the reality is that he comes from the bootstrapping world. He likes dealing with entrepreneurs. Looking at that from an outsider, I look at that and say: I agree with Michael. I think that going to Stripe and working with them to help entrepreneurs around the world, and small businesses, to succeed, that fits Patrick – from what I can tell – to a T. I mean that’s a perfect fit for him. With Stripe’s backing he essentially has resources that he can bring to bear on a problem that he sees as a worldwide problem of helping people to succeed with their businesses. The ability to bring Stripe’s resources to that particular problem – that is a huge impact for him. I think that, looking at that, if that’s his goal is to make an impact, I can’t think of a better way for him to do it. This relates back to the question of: What is it that you want to have an impact on. What are your goals? How do you achieve them? Even once you’ve achieved them, what’s next?

Rob [00:18:34]: Yeah, and there’s actually a pretty interesting chapter in Chris Guillebeau’s book. It was his first one. It was like “World Domination,” I think. He basically talks through entrepreneurship and some other stuff, and then late in the book he talks about legacy. He said at certain point, you got to start thinking, “What’s my legacy?” I remember reading this when it came out, which was probably – I don’t know – maybe 2010. At the time, I wasn’t ready to think about that. I remember dismissing that chapter out of hand, just being like, “I don’t even know what he’s talking about. I’m never going to think about that.”

[00:19:05] Then, lo and behold, a couple of years later I started realizing, “Wait. There’s something more here for me. Running businesses making $2,000 a month for the rest of my life is probably not the best use of my abilities. It’s not going to have the maximum impact. It’s not going to help people. It’s not going to help me and my family in terms of financially and freedom and all this stuff.” There’s so much that goes into this decision, and so I think at a certain point, as I said, you will probably start to shift and to think about your legacy.

[00:19:32] You know, there’s one other thing I wanted to bring up. I was thinking about Joel Spolsky and Jeff Atwood. I remember both of them just blogging in the early days. Joel Spolsky – what – around 2001, I think, started; and Jeff around the time I did, which I think was 2005. I watched Jeff move from a salaried employee to then working with Joel on Stack Overflow to then leaving Stack Overflow. Then they raised funding, and then he left and went to start his own – is it Discuss? Is that what it’s called?

Mike [00:19:56]: I forget what the company is called, but the product is Discourse.

Rob [00:19:58]: Discourse, yeah. Then the same thing with Joel. Joel was all about bootstrapping a real software company, and he built Fog Creek with Michael Pryor, which was awesome. Then when they started Stack Overflow, I was just totally shocked. I just thought he would run Fog Creek forever. Then when they raised funding, I was like, “What? But Joel always said don’t do the funding thing.” But then if you listened to his rational, it really made sense. They just had started a different business. He wanted to do something bigger. There was all this stuff that went into that decision to do it.

[00:20:24] So I think that’s even another story. I remember seeing that and hearing him talk it through, and being like, “That actually makes sense.” “That makes a lot of sense.” It didn’t tell me, “Oh, man, I don’t want to start a Fog Creek now,” which before I had wanted to start, like a software company. It didn’t make me think that I didn’t want to go down that path. It just made me think, “Wow, he’s just entering another chapter of that journey, and maybe I’ll get there someday.”

Mike [00:20:46]: If you look at examples of not just Joel and Jeff, but lots of other people in the bootstrapped world, as people grow their businesses, as they do things like that – they launch companies, and they exit them – it feels to me like they do bigger things over time. Nobody sets out to do something smaller than the last time. They want more challenges. They want to do things that are interesting to them, so the next thing always seems to be bigger than the last. It’s because people want to be challenged. Nobody wants to do the same thing over and over and over again. So, I think that what you’re seeing is as people move through this journey they start doing things that, to you, are unexpected, and it’s because you’re not necessarily in that situation. You don’t see all the things, and you don’t see the challenges that they’re having as boring. You look at them and say, “That’s exciting. I’d love to experience that.” But they’ve been through it probably numerous time, and they say, “I don’t want to do that anymore. Let me do something that’s completely new.” That’s why it makes sense to them, and from an external standpoint it really doesn’t sometimes.

Rob [00:21:41]: So, this is some stuff to think about, and this specifically relates to Patrick and myself and Glenn. The cool part is I think, a) this legitimizes this entire path of starting small. If you want to just stay small forever there are examples of people doing variations of that, where they just stay as the micropreneur, the micro [ISP?], and that’s totally cool. If you get there and you decide you want to do that, fine. But if you get there and you decide you get bored, this is the path. Look at what Patrick’s done. Look at what I’ve done. Look at how other folks have stair-stepped their way up.

[00:22:11] So, I think this: a) legitimizes it, but b) I think it’s cool that we’re still able to comment. We still have so much in common, right? Even when I was growing DRIP and we’ve been acquired now, I can still comment, I feel like, pretty intelligently on the early days, and how to – thinking about ideas and how to validate and how to find a market. I actually feel like I have more knowledge of that now than at any time previous. Just because I’m further away from it doesn’t mean I still don’t have a finger on the pulse of what’s going on there. Maybe over time, maybe in a decade, I won’t anymore. but right now I think the stuff we say on this podcast is still valid for a wide range of people, all the way from just trying to seek their idea, to building into a seven-figure SaaS business. I think there’s no question about it.

[00:22:57] The other good thing is there’re always people that’re kind of coming up behind us. You know, people who are currently earlier in the journey. So, you look at maybe Justin Jackson, [Kai?] Davis, maybe a Jordan [Dahl 00:23:09] from the Bootstrap Web podcast, Ryan Battles – I mean there’re people out there who really are focused on the early-stage stuff, and I think that that’s the cool part. This stuff’s all in flux, and people are at different stages. So there still is a lot of good information being created at all stages of this bootstrap journey.

[00:23:29]: So, the question I think we want to leave you with is: How far is your reach now? How much of an impact do you make, and how much do you want to make? The idea that entrepreneurship is – the goal of it – is to have an impact on yourself, on your family, and then maybe on the world? I don’t want to sound too grandiose, like starting DonNetInvoice had an impact on the world, but it certainly had an impact on my own life which allowed me to then change things, and change our lives. So, the question you want to think about as we leave this episode, I think, is: What do you want to have an impact on long-term? What do you want to start having an impact on? Maybe that starts with yourself. Then maybe the next one is your family – meaning you have more time, or you can travel with them. Then beyond that, that idea of legacy. How do you want to impact those outside of your immediate sphere?

So, thanks again, Scott, for the question.

[00:24:09] If you have a question for us, Mike and I very well may discuss it on the show. You can call our voicemail number at 888.801.9690; or email us at questions@startupsfortherestofus.com. Our theme music is an excerpt from “We’re Outta Control” by MoOt, used under Creative Commons. Subscribe to us on iTunes by searching for “startups” and visit startupsfortherestofus.com for a full transcript of each episode.

Thanks for listening, and we’ll see you next time.

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4 Responses to “Episode 307 | Is the Micropreneur Dream Still Alive?”

  1. Wow guys. This is the episode I’ve been waiting for. I’ll have more thoughts later, but I just wanted to say I’m glad you recorded it!

  2. Still living the dream!

  3. Wish I had a time machine to get to April Microconf

  4. Great episode. Thanks guys!