Episode 485 | Catching Up with Rob (An Interview by Dr. Sherry Walling)

Rob: Welcome to this week’s episode of Startups for the Rest of Us. I’m your host, Rob Walling. This week is a show we do about every three months. It’s a catch-up with me, my wife, Dr. Sherry Walling. She’s a clinical psychologist, a founder, and an executive coach. She comes on the show and interviews me about what I’ve been up to since the last interview. Tracy Osborn interviewed about three months ago. I hope you enjoy this episode as it continues to follow my story.

Sherry is (as I said) a clinical psychologist. She’s also built up a really nice personal brand in the space of helping founders succeed, and helping them stay the same while starting up. You can check her out at sherrywalling.com or @zenfounder on Twitter. With that, let’s dive in.

Sherry: All right. You feel ready?

Rob: Yup. I’m all good.

Sherry: You’re good to go? You’re focused? You’re here? You’re in the game?

Rob: Yup, I think so.

Sherry: It’s so much harder to talk about your own stuff than it is to interview other people.

Rob: I don’t know. Sometimes. I am on the interviewee side probably as much as I’m on the interviewer side. Maybe that’s not still true today, but I’m on it quite a bit, so I’m cool to chat.

Sherry: Do you tend to get the same questions over and over when people are interviewing you?

Rob: Yeah. If it’s a new audience, a new podcast, or someone’s who’s just doing a bunch of interviews with people that he or she doesn’t know. They kind of go with the surface stuff, and they have the same set of questions. They’re all pretty similar. But every once in a while, I go on a one called, What Works, I think it’s what it’s called, and she asked questions about values, imbuing things that you do with your values, and how you do it. It’s just a very different, whole different tact. Those can be interesting, or they catch off guard, frankly. They look at things from a different lens.

Sherry: What’s one of the most interesting questions that you’ve been asked recently?

Rob: That would probably be in that interview. She basically was saying, “How do you pass along your values?” or, “Which of your values do you want to be in the companies that you start and be delivered to the teams that you worked with?” and then, “How do you do that?” It was just a whole path of thinking about that. The reason it was interesting was because I had really not done a lot of thinking about it. I had to think on the spot what those things are and how I do those.

I listened to it today. It came out good. That’s actually the beauty of being asked the same questions over and over. You learn how you think about them. You learn how to answer them eloquently and in a way that’s succinct, not just you thinking out loud and trying to find your way to an answer.

Sherry: Okay. One of the things that I think is interesting about you is that you are working on three interrelated but separate businesses at the same time. The way in which those businesses are growing, they’re all growing and shifting right now. I’m curious how you direct that growth. Of course, we’ll talk about each of them separately. We’ll talk about MicroConf, we’ll talk about Startups for the Rest of Us, and of course, TinySeed. What’s the unifying thread? What are you trying to accomplish? What do you want out of these three businesses as they grow?

Rob: I realized this over the past two years after I left Drip. I was saying, “What should I do next?” I was looking at buying a tabletop gaming website. Just going completely off into a different direction, down a different path I had gone previously. But the more I looked at what I have done all these years for free (in essence), compared to the software products, the startups, and all that stuff that I had started, blogging, podcasting, and starting a conference are either completely revenue-neutral or rounding errors of revenue. But I did them, anyway.

That was a big sign to me that it should be the direction that I had. I realized that the things those had in common and that the three things you’re talking about—MicroConf, TinySeed, and the podcast—have in common is they help entrepreneurs. They help founders, they help us bring us strategies and tactics, but they also bring us together, and they inspire us to keep going.

Startups for the Rest of Us are free. It’s every week. There’s a little bit of community around it because you can tweet about it or be in the comments. You can hear other people answering questions and sending their questions in. But really, it’s a low level of engagement, and the cost is zero. If you take that up one notch, probably my first book Start Small, Stay Small is between $10-$25 depending on which version you buy. There’s no community there but there’s a lot of strategies, tactics, and some inspiration.

If you take it up another notch, then there’s MicroConf, which is our local events will be $99, and our growth is $1000 or $1100. There’s way more engagement. It’s super intense in terms of strategies, tactics, and inspiration, but they all do the same thing. They’re purely to help startup founders. One does it for free, one does it for cheap, and one does it for less cheap. Then there’s TinySeed. You can see the path, the thread that binds all those together. That’s really what I found of everything I’ve done in my life as a professional. That’s the most fun, and that’s the one that I’m most excited about. You can tell because I’ve been doing it for 15 years now. The same thing.

Sherry: But you’re a teacher. You’ve always been someone who learns something thoroughly, and then wants to explain it to someone else.

Rob: Yeah, there’s that element. That’s how it started with the blogging, the podcast, and the book (I guess). The interesting thing is it did not occur to me until a couple of years ago when it really hit me. I saw myself as a facilitator, getting people together to learn, and in the early days it was all about the tactics and the strategies. Then about (I’d say) seven years ago, we realized, “Boy, it’s much more about the relationships in the community,” and then a couple of years ago, I realized I really am bringing people together, like that’s the most important piece.

Sherry: It’s interesting to hear you say that as something that came to you later because in my life with you (which began 20 years ago), we identified ourselves as gatherers when we were in our early 20s. People would be at our house.

Rob: Yeah. That was always something we did, but you and I did that together. I didn’t know if I could do it on my own, if I should, or if I’m good at it. Then you looked at the track record of it. The interesting thing is when I actually looked at what I’ve done. There’s a certain amount of being successful, whether it’s as an entrepreneur or not, and it’s knowing myself. The more that I’ve learned about myself and removed those blind spots, the more I feel like I’m able to manage my own psychology, manage my own pros and cons, and strengths and weaknesses.

When I look back, I’ve had this blind spot of, I didn’t realize how much I wanted to get people together. You and I did it naturally (again) 20 years ago. One of my favorite parts of the podcast—which is a very unidirectional medium, is basically one or two people talking in the mic while everyone else was listening—are these Q&A episodes, where we get all the listener questions, feedback, and the voicemails. We can rally around that and feel like if you listened to five or six listener questions, you know, “Wow, it’s not just the two hosts that are answering this. It’s five or six other people.” Every month we do an episode. You hear they’re being people, even in the medium that is designed to not to be.

In my first book, I was going back and reading that, and I used a bunch of examples of Ruben Gomez, Ted and Harry from Moraware Software. I don’t remember who else, but even at that time when I didn’t need to do that, I realized that bringing other folks into the mix only benefits all of us. We are all smarter than me.

Then of course, MicroConf. Is that and TinySeed much more intense and much smaller scale? Having the batch of 10 founders is this super in-depth and intimate community.

Sherry: Let’s do a little bit of a deep dive into the podcast. There’s been some significant shifts lately. Mike is not on every week anymore, still part of the podcast but is not the weekly co-host. And you’ve made some other personnel changes by hiring an assistant producer. How’s that going?

Rob: It was touch and go at first. It’s just kind of scary to be on a show that has had a certain format for 450 episodes. Then there’s suddenly turned that over and say, “Can I do this? Can I really keep this going at a level that it deserves (given the audience), and just giving all the stuff we put out there?” Right now, it feels like since then, there were some touch and go moments, but pretty much everything feels up and to the right. I feel really positive about it.

I have a renewed energy around it, and I think people can feel that. I’m also, every week, thinking, what can I do differently this week? What can I mix up? The novelty of that, of even trying different formats, I’ve tried some that just don’t work out well, but people were like, “That was an interesting experiment. Have you thought about doing it this way?” It’s almost like customer development. Try something new and try something new, and just keep the variety going.

The interesting thing is when you do that, it takes a lot of time. You just don’t show up every week and talk for 30 minutes like we used to. That’s where the assistant producer comes in. I find myself spending more and more time each week just going guest research, writing questions, trying to find folks, and just doing all the stuff—calendaring, moving MP3 files from here to there, et cetera. It’s just all stuff someone else can be doing, so that’s really where I started looking for someone to help out and take that burden off because I wanted to keep doing it.

This is why podcasts stop. People can come up with great ideas and want to do them, but real life gets in the way. Running MicroConf and TinySeed, then having this podcast as well, there’s a lot going on in doing day-to-day stuff.

Sherry: Just a lot of admin, too. Moving files around is not that fun. You tried this discussion format. Did you enjoy that? Was it fun? What were the pros and cons of that?

Rob: Yeah. It was a news discussion show-type thing. It kind of worked. It mostly worked. It was super fun to record, but I think I want to put some tighter reins on the couple of the topics, and try to make them more current events. I also think that having three of us on the mic or even four at once and doing round-table on topics, I think it could be really interesting. I know a couple of other shows that do that. They focus on news topics like startup news or tech news. You hear a variety of voices from a variety of perspectives. It’s really interesting.

Again, that’s logistically a lot of work, to find those people, to find the time that works for everybody, then get all that audio files. Just get everything together. Writing the show notes, finding the topics, on and on and on. The shows I’m talking about are either the people who literally do them full time or they have full time staff doing them. That’s what I’m looking at. I’m expanding into that one because there’s no one doing that in our space. They do it more in the Silicon Valley or in the tech news space.

Sherry: Did you try a show format that you weren’t such a fan of? That you didn’t like? Or you didn’t feel like working well?

Rob: I don’t know. I did a couple of hot seats. I got mixed reviews or really I would ask people, “What’d you think of the hot seat?” They’re like, “Oh, you did a hot seat?” I was like, “Yeah. I went through this, this, and that.” Someone’s like, “Yeah, I don’t remember that episode,” which tells me it probably wasn’t memorable.

Sherry: It felt like an interview, maybe?

Rob: Yeah, I don’t know. I’ve also heard people say, “The ones where you go through with an entrepreneur, your troubleshooting things, and trying to think through, those are the most interesting ones,” which essentially are the ones with Mike and the ones that are hotseats. That’s always the issue. You only have a handful of data points in any of these things.

Even when I call for feedback and say, “I’m going to try this interview, call everybody back for a Q&A, and try this thing out. Give me your feedback.” I will get 5 or 6 people who sent me an email or tweet me out, or maybe it’s 10 or 12. But it’s not so many data points, that it’s not an end of 100 or 1000. I will often get two that say, “Yeah. That was really good.” And two that say, “I was kind of bored.” What do you do with that, at that point?

Sherry: You keep going.

Rob: Yeah, no doubt.

Sherry: Which is what you’ve done for 10 years now. The 10-year anniversary of the podcast is next month. Is that true? Is it really 10 years? That’s crazy long!

Rob: Yeah. March of 2010 was our first episode.

Sherry: Wow. Almost 500 episodes.

Rob: Yeah, that’ll be in June, that 500th episode.

Sherry: Dude, you’re an old podcaster.

Rob: It’s just really ancient in podcast years, yeah.

Sherry: In podcast years, that’s OG for sure.

Rob: Yeah. It’s a trip. To me, the 500th episode is a big milestone. 10 years and still super interesting. I don’t know if I’ll do anything fancy for that but 500th episode, I’m trying to wrap my brain of like, what do you do to celebrate that? What do you do that’s different not just the same episode that hasn’t been done before?

Sherry: What are you going to do?

Rob: I don’t know yet. I’m still thinking about it. I have some ideas.

Sherry: If you could live podcast while skydiving.

Rob: I could do that. I think the audio quality would probably not be great. Imagine that. “I’m your host Rob Walling.”

Sherry: It’s just like a long scream.

Rob: That’s the thing. A bunch of the formats that I do here, Mike and I did a live podcast recording at MicroConf Europe for our 300th episode. It’s okay. As a podcast, live podcasts are not that interesting. They’re always my least favorite. If I’m listening to a series and I do a live show, I’m sure they’re great fun to be there in person. There’s that energy, but it’s not as interesting. People are either… I don’t know. I don’t even want to conjecture why that is. I just know that I’ve listened to 10–15 live episodes from different podcasts that normally record in a studio. They’re just off their game. I can’t think of a single one that was better than just the normal episode that I normally record.

Sherry: I’m curious what the audience would recommend or would want to do with the 500th episode.

Rob: Yeah. I’d be happy to take suggestions either at Twitter @robwalling or questions@startupsfortherestofus.com. Definitely open to ideas and ask a few close friends of mine who listen to a lot of podcasts, what are the best episodes you’ve heard. Again, I have some ideas. I’m just trying to whittle it down and figure out what. I can come up with ideas that are really, really, a lot of work, and I’m trying to figure out how to either pair that down or make it happen or whatever.

Sherry: If work, money, time, and resources were no option, what would you do?

Rob: No limit, I would have 500 startups experts, founders, or people we respect answer a question, ask me a question, or something outrageous.

Sherry: That’s a really long podcast.

Rob: Well, that’s the problem. I can’t do that.

Sherry: 24 hours of Startups for the Rest of Us.

Rob: Right. Wouldn’t that be a stunt? Wouldn’t that be crazy?

Sherry: It would be a stunt, that’s for sure.

Rob: A three to four hour podcast. Maybe don’t do 500. Maybe just do 10. You can just see where it goes. I have to arrange that and figure out who to ask, get the files back, and all of that. And it has been done. I kind of have enjoyed some of those episodes we’ve done it ourselves. Our 100th episode was basically asking a bunch of people a question. We’ve got, I don’t remember, it was like Shawn Ellison, Andrew Warner, and a bunch of people answering questions that we tied in. That was a fun one. But, do that again for 500?

Sherry: I don’t know. I just know that the need to do something novel or new with that big pizzazz is maybe the best way to celebrate 500 episodes. I mean, 500 episodes is just relentless execution which is the Rob Walling theme. I don’t know about this pressure to do something new.

Rob: It’s possible. We did it for 400. We have a lot of these out. Four hundred was just an episode Mike and I recorded about being consistent. That was the whole thing. We looked back, and we talked about our metrics changes, audience listenership, and how we have shown up every week, why we show up every week, just all that stuff. We have done that, I’ll say, but I certainly could revisit that theme for sure.

Sherry: Well, that would be consistent.

Rob: Indeed.

Sherry: Right alongside this monster anniversary for Startups for the Rest of Us, you also have a new little baby podcast, the TinySeed Tales. I have to tell you, every time I see that title, I think about the DuckTales, a Disney show that existed when I was a kid.

Rob: That was an awesome show. That show holds up.

Sherry: It had this really cool song. So TinySeed Tales. How’s that going? You launched season one.

Rob: Yeah, season one went out. It was a podcast I wanted to do for years, but it took a lot of time and a lot of money because we have to pay a producer who’s producing it at a pretty high level, voiceovers, scriptwriting, and all that stuff. That was a cool experience to see how that’s done. You haven’t heard any episodes right?

Sherry: No. Confessions of the wife.

Rob: I know you don’t listen to my podcast and I listen to yours. Let’s put that for the record. If you listen to nothing else, you should listen to TinySeed Tales. It’s 8 episodes, they’re 20 minutes each.

Sherry: Why should I listen to it, Rob?

Rob: Because it’s good radio. It’s really good.

Sherry: What makes it good radio. I know it’s not just the production value, the money, and the time. Why is it good?

Rob: One part is you talk for 40 minutes then you take the best 15 minutes of all that audio. You pack it together, write five minutes of voice-overs. That is inherently going to be more interesting than a 40 minutes interview. You just get better tape. In addition, I really started doubling down in my interviewing skills right before that because I didn’t want it to suck. You know me when I’m new to something or feel like I’m not good at something, I dive in pretty deep.

Probably some of my best interviews I’ve given are in TinySeed Tales. The first season was with Craig from Castos. He’s also very thoughtful, he’s really good on the mic, it was a very natural fit for him to do. He wasn’t nervous. I could imagine doing it with somebody who hasn’t podcasted before, and I think it would have been a lot more challenging. Then there’s cool music, too.

Sherry: Oh, as long as there’s cool music. Is it the Tiny Tales theme song like DuckTales?

Rob: No, but we should’ve done that now that you said that. Dude, you’re mocking it. DuckTales holds up. It’s one of the cartoons from the 80s that’s considered to be very good.

Sherry: I’m not mocking it. I am singing along. You misunderstand me, sir. I’m not mocking it.

Rob: They’re redone it; Disney just redid it. The new one has Chucks, too.

Sherry: Have you been watching Disney Plus at night while I’m sleeping?

Rob: No. Maybe Finn has.

Sherry: Okay. One last question about the podcast. I know there’s lots of other things that you’ve been working on that I want to ask you about. What is your growth area in podcasting?

Rob: What do you mean? What growth area?

Sherry: You’ve been doing this for 10 years. What are you working on getting better at? What are you continuing to learn about and press into as someone who is guiding Startups for the Rest of Us?

Rob: Two things, you’ve heard me do intros and outros or solo episodes. I want to be able to do those almost without editing. When you and I are here talking, I’m not starting and stopping 20 times for five minutes of response. It’s just a natural conversation that flows. When I sit down to intro and outro this episode, Josh, our editor, is cringing right now thinking of how much he has to edit those two minute or three minute intros. Something about it when someone else’s not in the mic, I get stuck. It’s weird. I’m trying to work through that.

The other thing that’s more visible to the listeners is every interview I do, I’m trying to become a better interviewer. I’m trying to get better asking the right questions, asking them in a way that brings out the interesting answers, that touches on the emotions, but also brings out tactics and learnings. There’s a lot to be learned there. That’s what’s still exciting for me about the podcast. I think once I peek at anything, most of us, once you peak and you’re like, “That’s it. I’m the best there is,” it’s only downhill from there. That still feels like I can see a lot of mountains up ahead of me that I haven’t climbed here with podcasting. I think I can only get better in a lot of ways.

Sherry: Are you going to be doing this in 10 years?

Rob: I don’t know. I would say yes because that’s my personality, to just do things forever. I said that on purpose. I said it on purpose because I knew you’d laugh. Every software company I ever started I have not done forever.

Sherry: I know. That is absolutely not true, Rob Walling.

Rob: That’s the opposite, yeah. The Interesting thing is with books, blogs, podcasts, conferences, that stuff, I have done for a very long time. That was the signal a couple of years ago where I was, “I keep coming back to these things,” and podcasting is one. TinySeed Tales, while it’s been on this feed, I’m setting up another feed for it, and it’s going to be in seasons. But really, I have two podcasts now, and I could see having another. I enjoy it that much. I enjoy consuming podcasts that much, and I enjoy creating them a lot.

Do I think I will be podcasting in 10 years? I do. I think it might be Startups for the Rest of Us, but who knows? So much can change. If you think back 10 years ago, I hadn’t started Drip. I hadn’t bought HitTail. I hadn’t started this podcast. So much was different, so when I think 10 years ahead from now, where could that lead?

Sherry: Speaking of things leading places, let’s shift gears, move down the funnel a little bit, and talk about MicroConf. It has been a huge year for MicroConf already. You did this big announcement talking about reorganizing the schedule and structure of MicroConf. We are getting ready for MicroConf here in Minneapolis in just a few months, which I’m very excited about. So, 2020 compared to 2019, what are the significant changes that you’re implementing with MicroConf?

Rob: As you said, it’s a huge change. In 2019, we did three in-person events.

Sherry: Which was Growth Starter in Europe. Now, what’s 2020 looking like?

Rob: We’re doing seven in-person events. It’s Growth Starter in Europe, and then four were local events.

Sherry: You just sent me all the calendar invites in these events yesterday, and I was like, “Holy crap, you’re basically gone most of the month of October traveling around doing the MicroConf Roadshow.” It’s what I’m going to affectionately call it.

Rob: Yup. That’s exactly a good name for it. We went to seven of those, then we were doing the State of Independent SaaS reports. I’ll say we’re doing it. We did the survey, issued the report, did a live stream, which is I’ve talked about was quite an endeavor and a little bit nerve-wracking.

Sherry: A little bit nerve-wracking? Are you kidding me? You were sweating that for weeks. I haven’t seen you that stressed about something. Maybe the Drip sale or the decision to leave Drip, but you were like, “Which outfit should I wear?” It was really occupying a lot of space. Why do you think it was so challenging?

Rob: Probably because I wrote this blog post here years ago called Terror of First. I said that the first time you do anything, it terrifies you. Then, you just do it until you get numb to it. Pretty soon you’ll get better at it, and you’ll get more comfortable with it. First time I ever published a blog post, I was freaking out. First time I ever published a podcast episode, I was freaking out. First time I ever did a talk in front of people, I was freaking out. On and on and on. Each of those I have become more comfortable with. I think most of us do, and that this was one.

Doing a 30-minute live stream where you are standing, looking at a camera and nothing else, is not the same as standing on a stage at a conference and talking to 500 or 1000 people. It’s crazy how different it is. The energy is different. It’s a skill and it’s something that, if you’d ask me what’s my personal development this year, a lot of it is that it’s getting better in front of a camera. I’m not nervous. I don’t get the sweaty palms, hair standing up at the back of my neck, and throat closing. I don’t get that. You just get awkward naturally. The camera just doesn’t feel like a natural conversation because you’re talking to no one. You’re […] an abyss and trying to have a personality, and  I don’t think it’s a natural thing for us to do, at least for me. I’ll speak for myself.

Sherry: Oh, no. It goes against every part of our brains that’s geared towards interactive communication.

Rob: Yeah. No one’s nodding. No one’s saying, “Uh-huh.” You’re not getting any positive feedback, which in an event, I can be nervous, get up, start doing a talk, I start talking about things, I see people in the audience are going with it, they’re smiling, and I’m like, “Yeah, yeah.” You feed off that energy. You know that feeling.

Sherry: Oh, yeah.

Rob: And you don’t get that with the thing. That’s where, standing for 30 minutes with no script, no cue cards, talking, and knowing that there’s really no cutaways, even to get a drink, there was not enough time for me to stop and get a drink of water in the middle of that. I could have, but people would literally be waiting on a live stream while you do that. That’s a new experience for me. I’m sure over time, it will become more comfortable just like now on stage. If I need to stop and get a drink, the deafening silence that you hear…

Remember the first time you did a talk whenever you were quiet? It sounded deafening like you should be feeling the silence. Everyone was waiting for you to say the next word. Then, the 10th or the 20th talk you do, you’re like, “The silence helps.” It gives people space.

Sherry: Yeah, the silence is fine.

Rob: Yup. That’s where doing a live stream like that, I was like, “Which rules apply? Which don’t? What do I have to adjust here? How do I get in front of this many people?” It got recorded and now it’s on YouTube. I think it’s 2500 or 3000 views. I’m going to be seen by 3000 people on the camera. How do I make that interesting for them? How do I make it provide that value of 3000 people giving me 30 minutes of their time?

Sherry: Why was it so important for you to do this State of Independence SaaS? To do the report, to do the study, then to do a live stream? Why is that significant?

Rob: The report for me is like a passion project that I’ve been wanting to do for years because there just hasn’t been data in our space. We see all these reports about venture capital raising companies, their stats, and their benchmarks. I’ve just been so curious because people asked me, “How many people go to MicroConf have raised some kind of funding?” I was like, “I think about 10% but I don’t know.” I was super curious to hear that. I have all these rules of thumb like what your churn should be, what’s good, bad, and great churn, trial-to-paid conversion ratio, just all these metrics that I have developed the rules of thumb over the years, but it’s just from seeing a bunch of apps. It’s beyond anecdotal. It’s not that I had an end of one, but I had an end of dozens, I’ll say, that I’ve combined, and I wanted to see how those held up.

It wasn’t just a personal thing. I want this whole space. I think this is the future. I believe that this space is the future because venture capital can only be invested. It’s like 1 in every 100 startups or something; it’s a really small number. We’re “for the rest of us.” We’re startups for the rest of us. We’re the other 99%. I believed as we move forward (and had believed this for a long time), we are the long tail of startups, so where’s the data on us? Where’s the stuff to help us? Where’s the stuff to give us some type of benchmarks?

Sherry: How do you see the information in this report and in the live stream impacting an individual founder?

Rob: The live stream was 22 minutes, plus Q&A of me just walking through some high-level findings, and it was to get people interested enough in it to read the report. The report itself is 65-80 pages, depending on which version you get. There’s a lot more in the report. You can think of the live stream almost as an advertisement to download the report. Just to be like, “Hey, look at this thing. This is interesting and these are my thoughts about it.”

Sherry: It’s an abstract.

Rob: It is, that’s a good point. An abstract, like an academic paper. Whereas the report, if I was the founder, I would be looking, “Oh, where am I? What percentile am I at with my churn, with my trial-to-paid, and with my hours worked per week? With how many years I’ve been in the business versus growth?” There were just all types of findings in there that I think it depends on your situation that we can benchmark ourselves to. In addition, there were some interesting findings with which marketing approaches, which advertising approaches, are working best for you right now.

We now have a ranking on that in our space. We have payback periods for Facebook and Google Ads. You can see it. My gut was always, “1–3 or 1–4 months is where we want to be as bootstrappers, indie-funded, self-funded, founders.” That was the majority (I think) or maybe it was 40% or 50%. Again, it reinforces some stuff that I already knew. If I hadn’t already known that or if you’re just coming new to the space, you’re just trying to figure stuff out, you can just look through, and be like, “Okay. This is the sanity check range of where most people are.”

Sherry: And on some really, really, concrete things that affect choices that founders make every day. What’s this MicroConf Connect? More Slack channels for me to deal with? Oh my God, why would I do that?

Rob: Yay. I’m totally going to invite you. That’s another thing. It’s the State of Independence SaaS live stream. We’re doing a MicroConf Remote, which is a remote event here in (I think it’s) July or August. I don’t know if we have the date nailed down yet. Then, we have long been asked like, “I want to stay in touch with folks from MicroConf year round; there’s no way to do that,”  because would set up a Slack channel for an event, use that as a communication method, then we shut it down 30 days later. The reason we did it is because managing a Slack channel is a lot of work. You need to moderate it, keep it healthy, and there’s all kind of stuff to be done.

We now have the resources to do that. So, that’s what it is. It’s connecting founders, it’s an online home for the MicroConf community, founders and aspiring founders who want to build these ambitious startups, as I often say in the intro of this podcast.

Sherry: All of this stuff and change that’s going on with MicroConf in it, it is all rebranded and packaged in a great website now. You have that all redesigned and redone.

Rob: That feels really good.

Sherry: It looks so much better.

Rob: It was a side project. That’s the thing. The podcast and the MicroConf were literally side projects of Mike and I. We both felt like these should get more do. These are good things that should be treated better, look better. It feels good to finally have a logo that (I think) will last us a long time on a website and all that stuff. That’s been the big push since we brought Sander on full- time here about six months ago. It’s just getting your ducks in a row, how these all fit together, and how do we expand this in a way that helps more founders.

It comes back to that whole thing, why am I doing this? Because it excites me. I want to be in the space. I want to help founders. So, how do you help more founders? You do stuff that’s hopefully cheaper because a lot of people are bootstrapping, and you try to reach more people. That’s where you get the remote and local events where we roadshow out to folks, so they don’t have to travel.

It’s been a fun experience to try to brainstorm how to do that, how to accomplish that.

Sherry: What founders need.

Rob: Yeah, and how to do it in a way that’s economically viable. If you think about MicroConf being three in-person events per year, you can’t just expand that infinitely. It doesn’t scale. You can’t do 100 events per year. You can’t easily switch to that. How do you do that and expand it in a way that’s intelligent? Intelligent but somewhat scalable. That’s a balance we’re trying to strike. Some online stuff, some in-person.

Sherry: You just need to see it grow up. I think Startups for the Rest of Us, MicroConf, as you said, they were side projects. They were things that you did on the evenings and weekends when you were running your real company. Now that you have more time and energy to devote to them, they really are starting to look like that, and reflect that this is some of the core of what you’re doing, what you’re working on, and the ways that you’re serving the founder community. I love how they look. Both the Startups for the Rest of Us and the MicroConf websites are looking good.

Let’s talk a little bit about TinySeed. Since that is (I guess) your “real business” now.

Rob: Yeah, for sure.

Sherry: You’ve closed the batch two, right?

Rob: Almost there. We’ve made offers. We’ve had verbal yeses if everything goes through. You never know what’s going to happen when you get due diligence and paperwork, and we’ve basically in the midst of that right now, so sending docs, getting some stuff signed.

Sherry: Is that the least fun part?

Rob: For me, yes. The due diligence. I think for everybody, probably. It’s the due diligence, trying to get docs signed, and just all the questions.

Sherry: Paperwork.

Rob: Totally. Papers and paychecks. It’s been really nice to have Tracy around because she’s spending a lot of time that I spent last batch. She’s focusing on that and then Einar’s, working with her on that. Given the podcast expansion and the MicroConf expansion. It was like, “I can’t do that again.” You can only do so many things at once. That’s been the reason I haven’t been able to focus more on these other things.

Sherry: Is it the hope to bring batch one and batch two together in Minneapolis right around MicroConf time? Just everything converges?

Rob: Yeah, it does, which is kind of cool. That was by design and it will be by design. Since we are remote, there’s not a ton of overlap between the batches. It’s neat to be able to have the batch two meet batch one, and hang out. There’s the alumni association, so to speak. That’s a big factor in a lot of these accelerators. It will be in TinySeed, where the alumni help the next batch get acclimated, and can offer some mentorship or some guidance on a number of fronts. I think that’s the value.

Sherry: Yeah. They become mentors of sorts.

Rob: Exactly. That’s such a big part of the value of being an accelerator and not just being a fund. When you have a fund, you write checks to companies. Oftentimes, they never meet. They don’t really know each other. They’ll know of each other but they won’t hang out together. The batch part brings people together in such a tight community, and even across batches, being able to propagate that, and to have—by the time you get to batch three, four, or five—them reaching back to batch one who (a lot of those companies) will be wildly successful at that point. I’m willing to wager and have been willing to wager. They’re able to then continue to learn from them and also get introductions and work on the networks. The network of TinySeed founders will expand naturally each year.

Sherry: What changes have you made between batch one and batch two?

Rob: The process for batch two, the application process was more streamlined. It was just a better process. Of course, we tweak the application questions a lot. It was good to have three people who weren’t just myself. Actually, you were involved more on the first one because I have someone off questions. This time, Tracy took a lot of the third person role to weigh in on things. That was helpful.

We did change the funding amounts. We tweaked them very minorly. The version two terms, I believe, are the same. I don’t think we changed that term at all. Then batch two, we’ll tweak some stuff with the calls. We’re going to do fewer retreats. We did four retreats this year and our feedback was…

Sherry: Too much time in Florida?

Rob: One, too many retreats. Yeah. We’re going to move to three in-person gatherings which feels good.

Sherry: It’s nice to have some space to implement all of that retreat content between time.

Rob: Yeah, that’s the idea. What we found is you learn a ton in the first couple of months, let’s say, 3–5 months, 3–6 months. Then you really know where you’re headed after that. You have some small questions beyond that but it’s not the huge directional shift. Like in the first two months, we had multiple people that needed to completely redo pieces of their business. You’re charging three times too little or your on-boarding is no good. Your entire pricing structure is off. Let’s help you figure out how to tweak that or your copy is this. There’s some major changes. While those continue to happen in some former fashion, it’s not to the extent of the first few months of a program like this. There’s actually less of a need as you get through the program.

There’s a reason why a lot of accelerators are three months. You can provide a lot of value in that time. Of course, their goals to raise around haven’t really raised funding. That’s not our goal. We do think that SaaS, we know that takes a lot longer. We do want it to be longer than 3 months, but we also think that a call every week for 12 months is probably the initial hypothesis. It starts to feel a little heavy as you get further and further in. It’s like, “Do we really need two mentor calls a month still?” Even if there were 8, 9, 10, months into this. Or, am I just focusing on needing to implement right now? It’s almost accountability mode. I need someone to keep me accountable to sanity checks and stuff, to just keep me accountable to continue to implement these plans that I’m trying to get done by month 12.

We really have seen a shift in a lot of the thought process and the stages these companies are at, which is good. It shows there are emotions. A lot of folks came in relatively early stage and you hit a point where you don’t need all that anymore. You’re just plowing forward, blocking, and tackling, as they say. Just implementing.

Sherry: What are you most excited about a new batch, another round?

Rob: I think that with any startup founder (which I still consider myself), we’re implementing some things differently. I’m excited to see how that works out and don’t work out. I’m excited to get to know everyone. The relationships that I’ve had with batch 1 founders are truly valuable to me. And I don’t mean monetarily. I mean, I would call so many of these folk friends. Certainly, deep acquaintances but people that I enjoy hanging out with that I truly wish a lot of success on. I truly wish that they have a lot of success, purely because I think they’ve worked hard. Building new relationships is probably the best way to say it. That feels exciting. It’s exciting to me to be able to help people. It’s another group of folks.

Sherry: Yeah. It’s a deep investment in humans.

Rob: That’s what it is. That’s the part that excited me the most. Just in general, investing deeply.

Sherry: Well, you have a big year. Has it been two years since you left Drip? Almost two years?

Rob: Yeah, almost two years.

Sherry: There’s been phenomenal change in growth, the development, the inception of TinySeed, all the way to now, your second batch. It’s amazing to see the pace which you’ve moved, but also, you’ve been executing on these ideas and these materials for many years, at least 10 with the podcast. Again, we have that dichotomy of 20 years to overnight success.

Rob: Yeah, that’s how it feels. It’s that thing of showing up every day. It’s relentless execution, but what’s funny is that it makes it sound like you work to the bone constantly and work 60 hours  a week. That’s not what I do. Not really what I’ve ever done for any stretch of time. You can build it up, as you’re saying, but you do anything consistently for 10 years. You’re going to make some progress. You’re going to get better at it. You’re going to build something.

Sherry: Thanks for letting me take over your podcast today.

Rob: Yeah, it was great. I enjoyed the conversation. It’s cool to be interviewed by different people because they think about things along different axes, lands in different questions, and looks at progress along different axes, I guess, to say again. Yeah, I really appreciate you taking the time to come on the show.

If the folks want to keep up with you, you have your own podcast called ZenFounder. You are @zenfounder on Twitter and sherrywalling.com on the Interwebs. Thanks again to Sherry for coming in the show and look for another Rob catch-up episode here in about three months.

In the meantime, if you have questions for me or other guests who appeared on the show, please send me an email at questions@startupsfortherestofus.com. We also have a voicemail line people use from time to time, (888) 801-9690. As always, voicemails and audio files go to the top of the stack. If you’re not already subscribed to Startups for the Rest of Us, head to your podcatcher, search for startups. We’re typically in the top five. Thanks for listening. I’ll see you next week.