Episode 584 | Looking Back and Looking Ahead

Rob: Welcome back to this Happy New Year edition of Startups for the Rest of Us. I’m Rob Walling and this is the first episode of the new year. I recorded a version of this episode two days ago while my family and I were at a resort in Jamaica. I was actually looking out over an infinity pool, looking at the Caribbean Sea, and it was an amazing respite from the cold of Minneapolis, but also just the day-to-day of life.
We were in a place where we couldn’t decide to get distracted by doing laundry, being bothered by how dirty the kitchen is, or going into the basement seeing all the clutter. We were away from it for about eight days. That episode I recorded was just not good. It was really bad. It’s funny. First I thought there would be a bunch of background noise and there wasn’t. As I listened back to it, I thought to myself, this is not helpful, it’s not generalizable to people, and it was quite rambly. I’m re-recording it today with a new kind of tighter focus on a few key points that I had covered in that version of this episode.
This is a prior year reflection on 2021. This is the point where I look back at the prior year and think about what went well? What didn’t go well? What did I not enjoy? What do I want to do less of? What do I want to do more of? Then I look ahead to 2022 and whether you are the type of person who plans, who has goals, or who just wants some high-level ideas and thoughts of what they’re going to do over the next 12 months. That was my process during this time away.
It wasn’t a typical founder retreat. If you listen to this podcast, for any length of time, we call them founder retreats. I actually took this practice from my wife, Sherry Walling, also known as Zen Founder, who has actually written an ebook called The Zen Founder Guide to Founder Retreats. You can buy it, I don’t remember if it’s $20 or $25. It’s so worth the money if you’re going to take a couple of days away and do this kind of deliberate ritual.
Whether you do it twice a year or you do it once a year, it is something that can really help shape where you’re headed long term. It pulls you out of the day-to-day so that you’re not thinking what am I going to do this week? What am I going to do next week? You start thinking, what am I going to do next quarter, next half of the year, and next year?
I know that for myself, I tend to get heads down and relentlessly execute on whatever’s in front of me. Oftentimes, I don’t pull my head up and look and say, where do I want to be one, three, and five years from now? That’s what a founder retreat can do for you. If you’ve never taken one, I highly encourage you to do it.
This one that I did in Jamaica was with my family. It wasn’t a typical I have 48 hours completely unplugged from everything where I’m just thinking through, making goals, and making plans. This was more of an intermittent hour here, two hours there sitting, looking out over the ocean with my feet in the sand with a notebook and a pen, and giving some thoughts to all the things I just said. What was good, what was bad about last year, what do I want to be doing more of, and what are some high-level things that maybe I haven’t given enough deliberate thought to as I look out over 2022?
During that process, I also asked my two kids, just briefly off the cuff, what they were looking forward to either hopes or goals that they have for 2022? I’m going to roll some of that tape here in a minute. Before I do that, I know that some folks like goals and some folks don’t. I get it.
There’s a time and a place for goals given how specific you want to make them. Sometimes they’re like, I want to be at $20,000 MRR by the end of the year. Other times it’s like I want to have written 1000 words a day by the end of the month or I want something maybe more amorphous. I want to be enjoying what I’m doing in my day-to-day work by the end of the year. All of these things have a time and a place. Sometimes you just have a year where you can’t be as specific as you want to be, or you’re going to set some goals where you just don’t know if you’re going to be able to achieve them.
What I will say is that if you’re running a startup, if you can’t estimate your growth over the next year and make that some type of goal, then either you’re too early meaning you don’t have a product-market fit. Before you have product-market fit, before you ever product, it’s so hard to estimate how long something is going to take to get there. Either you’re too early or if you’re past product-market fit and you still can’t have some type of estimate of where you want to be at the end of the year, then it’s likely you’re getting lucky and that you’re going to plateau at some point and not be able to fix it or not know how to fix it right off the bat.
Maybe you’ll figure it out. You’ll probably figure out how to fix it because you’re a smart founder, but you might stay plateaued for potentially a very long time because what I see in startups that work post-product-market fit, as you have escape velocity, is that there really is a predictability to a lot of your numbers.
A lot of your funnel is coming in, you can tell visitors to trial, you can tell trial to paid, you can tell churn, you can see how many new trials or visitors you can get over the next 12 months, blah, blah, blah. Even if you don’t dig super hard into the numbers, it’s more science than it is an art to be able to project out a quarter or a year of where you’re going to be, and you’re not always going to be accurate.
This is not the time to say we’re going to 10X in the next year and to set goals that maybe you’re not going to be able to achieve. What I’ve found is that folks who do look at it pretty realistically and say, look, at our current course, we’re going to go from 1 million to 2 million this year. At our current course, doing what we’re doing today. Who can then say, well, what would we need to do to triple, to get to 3 million? Assuming that’s something we want to do.
I’ve talked about lifestyle entrepreneurs, and if you do want to be a lifestyle bootstrapper, awesome. You do want to put it on autopilot maybe or just back off and just do the minimum amount of work and get from one to two million, that’s amazing. Power to you. That’s a great business.
If you are looking to be more ambitious with your startup and with your growth, to ask yourself this question of, well, we can get from one to two, given our current trajectory, what does it look like to get to three or four? What would we have to do?
We’d have to hire ahead. We’d have to have two marketing efforts that really clicked or one that clicked really well. There’s just all these answers and all these questions that come about if you look at this as something that you’re aspiring to do, and some people are motivated by that. In fact, as much as I don’t really love the process, planning, looking ahead, and doing a lot of stuff that’s not just working in and on the business, this high-level stuff I found to be a necessity for me over the years growing as these companies get larger.
When I look around at the founders who I see who are doing really well and getting that fast growth, some are lucky and a lot of others are planning, they’re looking at these goals, looking at these the projections, or they’re looking at the goal and then saying how can I get there? Whether they hit it or not, it matters less than if they set that, they execute on their plan, and they do their best to achieve it. With all that said, I’d love to roll the tape of my 11-year old. I asked him what are some goals or hopes that you have for 2022.
Son 1: I’m working hard in school, but I want to work harder. I want to take care of the animals we have in our home because that’s important. I want to live with screens, but in a controlled amount be healthy. I want to have fun with the family. I also want to work hard on the violin and maybe improve on that. I want to help people when they need help. I want to live a good life. I guess that’s broad, but yeah.
Rob: I asked my 15-year-old the same question. I’ll roll that tape in just a couple of minutes because something that I was quite pleased with during these moments that I was thinking about or reflecting on in 2021 was just how much that my team and I have been able to accomplish in the last year.
It gave me the sense of I think gratitude, but also pride. Just pride in the fact that we closed TinySeed Fund 2 and are on our way to closing our EMEA Fund—Europe, Middle East, and Africa that we funded two more batches. We’re almost to our 60th company, and we ran six MicroConfs, two were remote and four were in person. Just to run in-person events this year. We hadn’t run them in so long. Shipping 52 podcast episodes, doing 20-something live streams.
There’s all this stuff that you forget in the day-to-day. Until I wrote it out, it just hadn’t sunk in how much we’re actually able to accomplish in 2021. Even though the first half we didn’t have vaccines. I got my second dose in May of 2021. Before that, it was still mostly lockdown-ish depending on which state I was in. We’re back and forth between California and Minnesota.
It was just 2020 and the early part of 2021 kind of all blended together for me and I think for a lot of us because it was kind of like pre-vaccine and post-vaccine. That’s when things started to change. As I looked at this list of what we were able to accomplish as a very small team, it made me realize the potential that we have to accomplish in 2022 in terms of running even more events and being able to fund another 40–60 companies across multiple batches. We’ll have two in the Americas and one across EMEA.
I was able to celebrate those wins and get excited about the year ahead. I was also able to reflect on probably some things that I should have realized earlier—mistakes or at least miscalculations, things I could have done better. One thing that I’ve been mulling over and trying to kind of hire for five, six months is to hire a podcast and YouTube producer who can help with this podcast, the MicroConf podcast, potentially TinySeed Tales, although I do have a good producer on that already, and our MicroConf YouTube channel.
I realized over this break and upon reflection that I should have gone after this more aggressively. I probably from the start should have made it a full-time hire. First, I was trying to do freelance, part-time, and then I was like, well, I could do full-time freelance, or maybe I could get multiple people. It’s just this dilly dally. I talked to some agencies and I see that as a process that didn’t go fast enough upon reflection.
I realized now that it has been slowing producer Xander and I down to still have too much going on in the day-to-day of these things. There are people out there who can produce this content really well. When I say produce, I mean, I’m still the host of Startups for the Rest of Us and the emcee of MicroConf. There’s all of that, but there’s all the behind-the-scenes stuff that needs to get done.
I am going to be looking at hiring someone full-time to help with all the things I just mentioned—podcasts and YouTube. It’s time to do it. We put out so much content kind of on the side. It’s on the “side” and I don’t mean our main events that producer Xander is putting out, all the MicroConf stuff, but everything else has just always been a side project. I wished I had realized that sooner.
If you are someone who listens to the show, you’d probably be a perfect fit. If you are either audio or a video editor/producer, someone who can weigh in on content decisions and help us ship more stuff, I’m going to be putting a job description together. Please do reach out to me at rob@microconf.com because I’d love to have a conversation.
One of the other things that I reflected on that I would have done differently in 2021 is when we decided to schedule the MicroConfs, we clustered them together and kind of a roadshow. There are going to be four of them in four weeks. Then we had to relocate to London, so it’s going to be five in five weeks. We couldn’t have London because of Delta, so we wound up doing four in four weeks. It was a ton of work and it wasn’t something that I think we’ll do again because spacing them out is fine. No one else cares.
Attendees coming to one event don’t really care that there’s another event the next week, but it did put a ton of pressure on producer Xander, who’s trying to basically plan all these events all at one time, and then it was a lot of travel in a short time span, which is obviously hard on some of us and hard on me because of the family back home.
This wasn’t one that I feel like is—I wouldn’t say, oh, it’s a mistake. It was an experiment. So many of these things in startups are experiments. We just made the call, we got excited about it, and then when we did it, it was like, huh. Xander and I looked at each other, let’s not do that again.
What we’re looking at in 2022 is making a change and it actually gets me excited to look out and think, okay, well what if we had one event almost every month in 2022? There’ll obviously be our flagship growth events, then we’d be looking at some local, which are the one-day events, and then a couple of remote events as well. I have a couple more thoughts for you, but I want to roll the tape of my 15-year-old when I asked him what are some of your hopes or goals for 2022.
Son 2: I’m hoping 2022 is finally going to be the year that COVID ends. We drop the mask mandate and I can walk around the school again without masks, social distancing, and stuff. That’ll be nice. It’s also going to be the year that I turned 16 so I’m hoping to get my driver’s license. If I finally stop procrastinating, finish my book.
I’m also hoping to get a good gaming computer, not the one that I have now, so I can run stuff on high graphics without my CPU spontaneously combusting. I’m also going to try and expand my Warhammer 40,000 collection. I own a decent amount of stuff, but no complete armies yet. I’d like to fill those out.
Rob: By the way, if this format feels familiar, you’ve probably heard it on Zen Founder. Sherry’s the one who has actually done a lot of interviews with our kids and bringing them into the podcast episodes. I’ve never done it on Startups for the Rest of Us, and it was just so easy to do. These interviews or these short clips of the boys were actually recorded while we were in Jamaica, and that was one of the advantages of being there with a family with a microphone in hand.
I want to leave you with one final thought about the power of focus and the idea that most of us have shiny object syndrome. Most of us take on too many things and continue to work on things that aren’t working. Maybe we don’t know they aren’t working because we’re not measuring the right things. We’re not evaluating the data, or maybe we do know that they’re not working but we do them anyways out of a sense of obligation because we just don’t take the initiative to stop doing them or because there’s some kind of emotional attachment to doing these things that we feel like if we don’t ship one blog posts a week, even if we’re getting no traffic to our blog, that somehow we are failing as a founder.
In my experience, the things that we decide to stop doing or the things we decide not to do are as important as the things we decide to do. As you reflect on 2021 and 2022, or even if you’re listening to this a year or five years from now, I encourage you to think hard about what’s working, what’s not, what do you want to do more of, what do you want to do less of, and what do you want to stop doing in the new year?
Thanks so much for joining me, not only this week but this year. I know this is going live shortly after the new year, but it is technically the last episode of this show recorded in 2021. I look forward to being a part of your journey throughout this new year, whether that’s through strategies and tactics that I’m able to pull from guests or share from my own experience, from the experience of the founders that I work with, inspiration from the stories told on this show, or through the mental frameworks and almost the more philosophical topics that I sometimes cover in my solo adventures.
I just look forward to being on this journey with you. My hope is that you enter a prosperous and happy new year with you and your family and with you and your startup. It’s great to be along on your journey. As always, I’ll be back in your ears again next Tuesday morning.