In this episode of Startups For The Rest Of Us, Rob reflects back on his goals of 2019 and shares some lessons that are broadly applicable to founders/entrepreneurs. He also shares how he “unplugged” from the internet/devices while on a recent vacation with his family and the benefits he experienced.
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I’m going to cover a couple of things today. I want to talk a little bit about unplugging, based on recent experience that I had going to the Dominican Republic with my family. It was my first time there. I unplugged, we unplugged for half of the trip. It was four days with no wifi and no Internet at all. I want to talk a little bit about that experience and the impact that it had on me, something that I want to make a habit of in this coming year.
I also want to revisit my 2019 goals. I know often around this time of the year, Mike and I revisit our prior year goals and we look ahead at the next year’s. I’m not going to do something nearly so formal, but I did want to talk through quickly, some of the goals that I had set for 2019. I have some other reflections on 2019, some lessons that I learned, that I think are pretty broadly applicable to founders and people doing hard things, ambitious folks trying to build something that is difficult.
If nothing else, I hope that you leave this episode with a sense that we’re all going through the same thing, we all experience these same thoughts, and experiences are very similar ones as we do these. It’s this feeling of, “Wow, I’m not moving fast as I want,” or, “I’m not very good at this,” or, “This is scary and I don’t really want to do this anymore. How am I going to fix this?” that type of thing. As I reflected back on stuff that’s happened over the past 12 months, it has been an absolute whirlwind. I want to talk through some of that today.
To start, over Christmas and New Years, I spent eight days in the Dominican Republic with my family. As I said, I had bever been, my kids had never been, but Sherry had, either spoken in an event or been in a retreat there earlier last year. She booked eight days for us and the later half of that was completely off the grid.
It was scary at first. I will admit. It’s weird, I’m not on Twitter and Facebook all the time, and I’m not in Slack all the time. I don’t need that constant dopamine rush of an app giving me feedback. It’s just not how I’m built. I shouldn’t say that’s not how I’m built because I have been there at times, but I’ve been very deliberate about not allowing myself to fall into that trap. Yet, I found myself frequently thinking of something, wanting to just know the answer right then, and wanting to Google it. Realizing, “Oh, I want to listen to that book,” going to Audible and not being able to download it. It was this slow grind on me, this realization of how reliant I am on external inputs.
I’ve always consumed a lot of media, typically reading books, listening to books, listening to podcasts. I do that because it gives me new ideas and fresh perspectives that allows me to view my day-to-day job in a different way, but it also allows me to come on this show and not say the same things over and over, to have an evolving perspective.
What I also realized is if anything, I consume a bit too much. Even though I feel I have a pretty good balance of consumption in production, in producing things, podcasts, conferences, accelerator or whatever, I realized during this four-day Internet fast that my mind wandered in glorious ways. I got so deep into topics that I just wouldn’t have stumbled upon, how I not had this time.
This wasn’t a retreat. I’d like to take a retreat once a year, maybe twice a year if I really need it. Typically, it’s a once a year cadence where I ask questions, then I sit down and write stuff. This was and that. I was with the family, I was not asking specific questions, I was really casually moving from one topic to the next, and it led to some real ground breaking insights, to some problems, or just issues that MicroConf expansion over the next 12-18 months, has a lot of logistics and a lot of things that we’re thinking about. How can we do this well? How can we make this better? I just had a lot of thoughts on it that didn’t have the space to come out in my day-to-day and creative ideas bring seemingly from nowhere, but they weren’t from nowhere. It’s all the thinking, the note taking, and just the 10,000 hours of going through this process. I think it was a real reminder for me to do this more often.
As I said, I only want to do a retreat every year or so. I actually think I want to do this off the grid thing quarterly. I feel like I could do it once a month, in all honesty. It was calming and soothing to just go away, turn off the Internet, and think about things. You can tell it rock my world, so that’s something that I want to try to do in 2020, is do this off the grid.
Bill Gates used to call it “think weeks” and I think he only did it once a year, but I wouldn’t necessarily go out with the intent of reading a bunch of books and synthesizing information. It really is, what are the broader issues at hand that I want to think about, but it’s also just let your mind wander almost in a meditative state, let the issues show themselves, let the thought show themselves, and let these creative insights come. That was a bigger realization for me.
If you already do that, I’m impressed. If you have never done this, obviously, it’s easier said than done given how busy all of our schedules are. It was pretty eye-opening to me, it is something that I believe is a practice that I am lacking in and I want to do better. That was unplugging.
Second topic I want to cover are goals that I had set for 2019. Really, I had four goals that I had set about. The first was exercise two or three times a week. I mostly achieved that. I was way ahead of it for a while. Once winter came, travel got in the way. I have absolutely fallen off the wagon. I feel that’s mostly a thumbs up-ish for me and it’s something that I need to keep doing especially as I get older. My birthday was just five day ago, so I’m another year older and I need to keep thinking about it.
I hate exercise. I just don’t want it. I never liked it. I was always an athlete in highschool and college, so I didn’t need to exercise, because that’s just what I did. It was built into this routine of, you go in your practice for two hours and you’re in this amazing shape, but that where I’m at. I have to set this goal for myself, otherwise, I don’t do it. That was number one.
Second one was to continue pushing TinySeed forward. It was to get the first batch chosen. It was to get the first batch to have a noticeable impact on their growth and not just me, obviously, but the program itself, the mentors. To make TinySeed essentially the preeminent accelerator for bootstrapper and for folks who don’t want to shoot the moon and who want to build this ambitious yet sane stuff for startups. I feel like that is on, or ahead of schedule with everything that I had envisioned and spoken with my co-founder, Einar. That feels like a win to me.
At this point, things are continuing to roll and frankly accelerating, both with TinySeed and the applications for batch two. We had a lot more folks with revenue, we had a lot more folks with tractions in the second application process. With MicroConf expansion, the way the podcast has continued, even though Mike has taken a step back, a lot of things are hitting on all cylinders. It hasn’t been easy and I’ll get into that a little later in this episode, but in taking stock on what happened in 2019, I’m pinching myself a little bit.
It’s interesting. I got an email last night actually and it was from Squarespace. It said, “Hey, your website, tinyseed.com is about to renew on the annual plan.” I emailed Einar and I said, “It was only a year ago that we started our first application process and that we had a website.” Before that, we did a landing page or something for a couple of months prior, but that’s it. It feels like it’s been two or three years based on how fast things have moved and how ambitious we’ve been with it, but how things have come together.
Not everything comes together, that’s for sure, but there was so much work to be done when this Squarespace site went live and we started taking applications. It’s that sense of we didn’t have a bunch of systems in place. We didn’t have much of employees. We didn’t have a bunch of funding. It was the two of us and we are raising enough money to trying to do the first batch. We didn’t have an amazing application process. It was a Google form that fed into a Google Sheet, that when people ask, “Hey, I’d love to get a confirmation email.” I sat and thought, am I going to write some code to make it to this? Am I going to have to go back and hack PHP, or learn Ruby to make it do this?
Of course, I remembered Zapier monitoring Google Doc and say, “That was it, it was just gum and bailing wire, and you’re just trying to keep it together,” but the outward appearance was not that. The fact that I was sifting through 880 something rows in a Google Sheet, trying to sort things, interview people, and doing 70 something calls, it’s the image of that duck that’s on the water. From above, it looks calm, but underneath you’re just paddling like crazy. This is as much as startup is as anything I’ve ever done in terms of the uncertainty and just the scrappiness that you have to do.
In that startup life, I used to work with a guy who would say, “In startup world, a week is a month, a month is a quarter, a quarter is like a year, because you’re moving so fast.” That’s been a big reflection of me. I think something I’m pleased about with 2019 is, I don’t work a ton of hours. I don’t work 50-hour weeks. I work normal work weeks. I take time off to reflect, and I feel like that.
My advice to you if you’re not already thinking this way is that’s how you play long ball. That’s how you do this for 15 or 20 years because being an entrepreneur is very, very hard. As we know, it’s extremely stressful. If you work this 50–60 hour weeks, you can do it for a short period of time, but over time, it degrades your ability to produce. Anyway, that’s the reflection on TinySeed. I’m going to talk a little bit more about MicroConf in the podcast in a couple of minutes.
My third goal was to not not freak out when the stock market crashed in 2019. That just didn’t it happen. That was more of a prediction than anything. I’m not sure if that was actually a goal.
The last goal that I completely failed on was to write, or re-write a book. That one has been on my list for years and it’s always been a Plan B, that if I have time, I really want to re-write Start Small, Stay Small. I still get a lot of emails about it. It’s still 90% applicable, but it’s dated. Some of the links don’t work and there’s just certain tactics that don’t work. I’m at the point where I kind of throw my hands up, like is this something I think I can pull off in the next year? I just don’t know. I need to get more thoughts to doing that.
The interesting thing for me is my day-to-day work, not my personal life, but work life has really come down to three things: MicroConf, this podcast, and TinySeed. I’ve already talked a bit about TinySeed and what we did last year. A question I get (actually often) is, “How do you get so much done or how do you run all three of these things? They seemed very time consuming.” It’s often hard. I’ll answer, “Well, I have a Trello board and I have a process, all these and all that,” and that’s part of it, being efficient, being fast with email, and delegating all these stuff.
I think the biggest thing that has saved me hundreds of hours, if not thousands, is this division of responsibilities to extremely capable people. It didn’t happen by accident, but it’s something that I’ve learned over the years. Some people get here really quickly. Some people immediately think, “I need senior project thinkers who can get things done.”
I started with a very limited budget because I was a bootstrapper, with basically no budget and a salary for my day job. I went for a work week route in 2007 and started hiring VAs, which are very task-based people. You need heavy process. That worked for that stage, so I hung on to that stage too long, that stage of task-based people.
That was really right before Drip and it wasn’t until Drip where I realized, “Wow, hiring project people, where they can handle an entire project, even if they need some training, they’re more expensive than task based, but they’re such a step-up in terms of how much you can delegate, much you can give and expect results.”
I think the next step up is a product person. Someone who isn’t just working on a project and managing that in timelines and dates because you can find a lot of project managers, but how many product people can you find? By product, I don’t mean software, I mean a podcast, if you think about it, is a product. A producer could produce it in a way that’s really at a high level. That’s better than someone who, you’re just like, “Okay, these are the dates and these are the timelines of the podcast. This is who needs to be on.”I was actually thinking about how do I make this better, how do I think ahead and add things to this.
The same thing with your software product that you’re managing. Obviously, it’s a product. The same thing with MicroConf. That’s a product if you think about it. It’s a bunch of different smaller events. Now, it’s online stuff. It’s the state of indie SaaS report and the live video stream that’s going to come along with it, the Slack channel and all of that. It’s all really product-based thinking.
While I could sit down with someone and outline, “Hey, week-to-week, month-to-month, this is what needs to happen and someone could logistically do it.” How do you find someone who’s one layer above that? As a product thinker, something with TinySeed as an accelerator. It’s a bit of a luxury, but it’s a realization I’ve had that there is no chance that MicroConf, TinySeed, and the podcast could all exist at the level that it does, without many product-based thinkers.
That started off as Einar and myself, and then Tracy joined the team to be thinking about TinySeed. It’s not just how do we run TinySeed, but it’s how do we make it better constantly and new suggestions of how do we improve this process. I talked about our application process for batch one, that was bailing wire and duct tape. When the second one came around, Tracy evaluated all these tools, just went off, and made recommendations to us. Basically made a decision to make this thing better and more manageable. It is, it’s better. We look at it as v2.0 of our whole process.
As we expand, because we’re going to fund more companies with this second batch than we did in the first, obviously, batch three, four, five will expand from there. These things have to get better. I think that the scrappiness of that initial one of just getting it done is what a lot of us founders are really good at. How can you find a person if you’re not good, I’m not great at, then putting that into writing, communicating a process, and improving upon that process constantly iterating, that’s not my strong suit. But that’s okay because you can find people, you can hire people, you can work with people who can help you with that. That’s where you’re really going to level up, is where you figure out your strengths. You double down on those and how do you backfill against your weaknesses.
Speaking of the podcast, I have to admit, I haven’t talked about this on the show. With episode 448, when Mike and I had a really intense conversation about him stepping back, focusing on Bluetick, and whether or not he should, that whole thing (again, if you haven’t listened to that) is one of the best episodes of this entire (almost) 500 episode run, in my opinion.
I was kind of scared after that because how do you take something that has been running for close to 10 years with two people, has a very defined format, we have not iterated very much on the format, and how do you reinvent it in a way that hopefully: (a) isn’t the worst, (b) isn’t just as good but is actually better, how do you do that? That’s a task that I was faced with back in that May–June time frame. It’s close to seven months now.
I’ve done some experiments. I’ve tried different show formats, Q&A with different people. Obviously, have been doing interviews but trying to do interviews in a different way than everyone else does, hot seats, there are some solo episodes like this, but there was a lot of uncertainty there for me. I certainly felt more trepidation and angst about keeping it going and I how I would do that. I was also highly motivated.
There’s this interesting thing growing up. It was not an option for me and my siblings to quit things. I don’t want to sound like the old guy who walked uphill both ways in the snow, which I did not do (I rode a bus to school), but being in school, I was one of the scholar athletes where I got straight As and also played two sports. It was just a given, that I got on the bus at 7:30 and my parents pick me up after football practice at 7:00 or 7:30. It was just 12-hour days and I never once thought this is hard, I shouldn’t do this. It was just, this is what we do as scholar athletes or as entrepreneurs. We do the hard things. I think it’s almost easier when you don’t question them. There was, of course, a certain point you can drive yourself to depression, there’s health issues, there’s a bunch of stuff.
When Mike took a step back, I never once thought, “Well, I guess we should shut the show down. I guess we should end the podcast,” because it’s just not an option to quit. Again, there are exceptions. It’s an option to quit if your startup isn’t working, you’re going bankrupt. There are things, there are ways, but in these scenarios where it’s not everything falling off a cliff, but it’s like this is hard, or this is a mental challenge, or a physical challenge, for that matter, which is what it was growing up in highschool and college. It was hard workouts, it was staying up then to try to finish homework, it was being tired a lot, that kind of stuff. Again, it’s just wasn’t an option not to do it. I think that’s a skill. That skill of hard work and the ability to not just question things, I think has served me well.
The feedback I’ve gotten on the new podcast format has been overwhelmingly positive. I’ve loved the constructive feedback I have received and I’m making tweaks to the show format, the week-to-week stuff. I plan on once again continue to double down on the show in 2020. My love that I have, the freedom to experiment with things, and sometimes they work and sometimes they don’t. I love that I have the time to do it.
I know I have a limited time, given everything else, but it is in line with MicroConf and even with TinySeed, the ability to do TinySeed Tales. I wanted to do TinySeed Tales for five years, that high level of NPR production. Didn’t have the time, didn’t have the budget, and this moment is essentially was an excuse for me to do that. We are certainly looking at a season two of TinySeed Tales. Plan to keep doing that based on the feedback I received.
One more reflection on 2019 I wanted to share with you before I wrap is once again that reinforcement, that running something on autopilot or doing something for the second, third, fourth, fifth time is not that hard. But launching new things is extremely time consuming in way more than you think it’s going to be. This is the reason why I always advise people who say, “Hey, I’m going to try to launch or grow two pruducts at the same time, even two info products,” to don’t do that. Grow one, get it to a plateau, auto-pilot it as much as you can, and focus on the other, because launching two things is time consuming, it’s mentally taxing.
With MicroConf, we’ve done 19 of them, our 20th, and our 21st are here in a couple of months. We’re pretty good at them at this point. Obviously, we can always improve, but it’s not a decision point of everything of what should the format be? What should the meals be? What should the schedule be? Really, it’s a known quantity. Even if we revamp it and tweak it each year, that’s a known quantity. It isn’t as time-consuming as something that you think is going to be pretty quick. Like the example that I’m experiencing, that I just spent five hours yesterday working on, is a state of independent SaaS survey and report. I literally thought that I could hire a designer, hire a statistician, then draft a survey, and hand most of it off to be done. That has not been the case.
We are literally hundreds, hundreds of person hours into this, including the designer statistician and my time. It has been so much more of my time than I estimated or anticipated. It’s worth it. Like the results, I’m starting to see we have versions of the report now that we’re tweaking and it’s absolutely worth every minute and every dollar that we’re spending on it. But it is that reminder to me that everything is new, everything is a decision, and everything has to be thought through from square one, about how we word things, the look, the feel, how we analyze, and what assumptions we’re making. It’s just that everything is new.
That’s the same thing when you’re building a product. You don’t know what features to build next, what customer to listen to, and everything is new. You don’t know if your pricing is off, you don’t know if your messaging is off, you don’t know if your positioning is off, you don’t know if your brand is off, or all of those things is on and only one os off. It’s just so hard, there’s so many variables, so many decisions to make. This is why launching new things is time consuming, it’s mentally taxing, and it really takes a founder mentality to do it.
You can’t hand off a task that requires a founder to a project person, or oftentimes, even a really good product person has a tough time doing something from scratch. There’s this very unique skill set that takes something from zero to one, in that sense, from zero to existence. It’s really hard. I do believe it’s something that we get better at the more you do. I also think that it’s one of the hardest things that I’ve done over and over.
There’s this old marketing adage, you launch a new product to an existing audience or existing products to a new audience, but never do both at once. That means a new product to a new audience. Frankly, at some point in your career, you have to, because nobody starts out without an audience or a product and that is the hardest part. As you’re grinding it out, as you’re struggling through these decisions, the uncertainty of what you’re doing, rethinking your pricing and thinking, “Wow, everyone else has this figured out, why don’t I know what to do? Why don’t I know the right answer?” The answer is, no one else really does either.
In closing, I’m not sure if there has been a year in recent memory that I have looked forward to more than 2020. For me, personally, it’s a lot of friends. I’m enjoying the podcast, loving, doubling down on that. I’m loving the way that TinySeed is expanding and I’m super stoked, honestly, about MicroConf in the expansion. It’s just everything that I’ve been working on for 15 years has come together in a way that I don’t think I could have imagined. It makes the hard days and the set backs so much easier to fight through when you have the winds along the way and when you have good people, talented people that you really enjoy working with, and that essentially you’re constantly collaborating with to make whatever it is that you’re working on better.
With that, I’ll wrap up this episode, I wish you a prosperous, a successful, and a happy 2020. Thank you so much for being a listener of Startups for the Rest of Us for all these years. In a couple of months, we’re going to be at our 500th episode, 10 years, and it comes even before that point. It’s just a pleasure to be able to get on the mic and talk to you every week.
Thank you so much for listening. Thank you for all your support, your feedback, and your comments. I’ll see you next time.