Speaker 1 00:00:05 Hey, welcome to Subscription Heroes. I'm your host, Scott Herf, co-founder and chief product Officer of Turnkey. Today I had the honor of chatting with Rob Walling, a serial entrepreneur, investor, founder of Tiny Seed MicroComp Drip, and the host of a number of popular shows, including Stars. For the rest of us today, we'll cover his motivations and process behind his new book, the SaaS Playbook, how he sustained his media empire, and the secrets of his production process, his thoughts on the marketing, like a media approach, how he ran marketing at the startup Drip, and the secrets behind taking care of himself as a founder and operator in super high stress environments. This is a great chat. Hope you enjoy it. All right. The SAS playbook coming out in July, right? Over a hundred K and uh, on Kickstarter. Yep.
Speaker 2 00:00:53 Pretty excited.
Speaker 1 00:00:54 Technically, your fourth book, which you just told me before I locked up
Speaker 2 00:00:58 Yes, indeed. Doesn't get any easier, <laugh>, you think? Think the third and fourth are gonna be easier. Nope. It's actually harder now. I have more to do. You know, I have more companies running and all that.
Speaker 1 00:01:07 It also blows me away, like I switched from non-fiction. So I wrote a book with O'Reilly in 2016, and then that will came out in 2016. And then I, I was like, let's change it up. Let's do fiction, which was just dumb and not exciting and all sorts of things. But, you know, volunteering to go back to the well over and over again is, is impressive. And you're doing the audiobook, which is bonkers to me. Well,
Speaker 2 00:01:29 That's just, that's the fun part, right? Cuz then I get to point out, I get to make a bunch of commentary as I'm reading and of like, Ooh. Yeah. So I would say that differently today. Or hey, you know, make it, making little jokes, poking fun at things. And I don't know that that's fun. Yeah, it's gonna be, it'll be some work, right? Yeah. It'll be probably two six hour days. I bet it'll take me to read, read through it. But, you know, I used to be known for blogging. Like I know that's probably hard, you know, but like 10 years ago Yeah. That's what people knew me for. And then it was like, oh, there's this blogger who wrote a book who is now has a podcast with a thousand listeners. Right. But now people know my voice better than anything. Right. And so it, which is weird for me to say, but like, I get, I've gotten, I've gotten recognized on airplanes and like at Starbucks, people hear me talk and are like, are you <laugh>? I was listening and I was like, oh boy. So I would've a really tough time outsourcing the audio book reading for
Speaker 1 00:02:18 Sure. Yeah. I remember when we got on, um, the first time I, we did the pitch for Tiny Seed disclaimer, turnkey is a tiny seed company and like hearing you in real time was just kind of this weird mindef Yeah. Where I'm like, oh, he is real <laugh>, you know?
Speaker 2 00:02:34 Yeah. Yeah. And it's weird to hear, I've had people on tiny seat interviews, I'll ask 'em a question and they just won't respond and then they snap out and they're like, oh, I thought I was listening to an interview. I didn't realize you were interviewing me. You know what I mean? It's like a weird Yeah. A weird thing. I had the same thing, right? I'm a huge fan of this guy Tom Merritt, who's like a new a tech news pundit. He is Tech News today. Uh, no, no, it's called Daily Tech News Show Cord Killers. And I interviewed him for startups, the rest of us, like two months ago. Same exact thing for me. I was like, whoa, this is so weird. Also, you talk about 50% slower than I thought you would because one five x, you know?
Speaker 1 00:03:06 Oh yeah. Right. Yeah, yeah, yeah. People don't actually, and then, you know, they're, they're dropping all the ahs and ums and you know, they sound so less,
Speaker 2 00:03:13 Less you're edited. Yeah. You <laugh> you sound so much better when you're edited. Yeah. Cuz you and I, you and I and your co-founders have, you know, hung out at tiny Seed retreats and all that. Yeah. And I'm always, I'm always keenly aware of like, huh, I wonder if I sound not as smart as I do <laugh> on the podcast, but what whatcha gonna do
Speaker 1 00:03:28 Well, for what it's worth, you are even more impressive in real life as if you need needed to know that. But yeah,
Speaker 2 00:03:34 Thanks man, appreciate it.
Speaker 1 00:03:35 Back to the, the book thing, the fourth time, back to the, well, I mean, you must have seen something that's missing out there that propels you,
Speaker 2 00:03:44 Right? That was it. Yeah. I'm kind of a, in a weird way, my best works that I've ever done, including like the, maybe the best podcast episodes or the best blog posts or the best books or the be like the best pieces of content I've ever written or created, usually come out of some type of anger. Cuz I'm like, I feel that. Why are, why are I, I, you know, I read 10 books about starting SaaS, starting startups, whatever. And they're shit, they're terrible. And they're so, you know, and, and I get so angry and so I started talking to a good friend of mine, I've been in a mastermind for like 12 years and he's like, well you should write another book. And I'm like, dude, I don't have time to do that. Right? And he's like, well what would it be about? So he totally, he knows me really well.
Speaker 2 00:04:23 You know, when your spouse just kind of leap pulls you along, like he's like that, right? Hey, so, you know, if you were to write a book, like what would be in it? So we sitting there talking on this mastermind, I start jotting down notes. I'm like, well obviously, cuz no one's really talking about building like SaaS team when you don't have 10 million in the bank, right? What if you only have 200,000 in the bank or you have nothing in the bank and you're trying to be, you know, so there'd be a chapter on that. And then how about just something about B2B SaaS marketing approaches and like, which should I choose and why? What's a framework around that? Now we have Traction by Gabriel Weinberg from a few years ago, but it's a little dated and also not focused on SaaS. So each of these things. So as I started writing 'em, I started getting riled up as you can hear me doing now. And eventually he's like, yeah boy the world really needs that book. And I'm like, screw you man. So within two weeks I started writing it. Like he totally, you know, it's like a, you've heard of a hate watching where you hate watching Netflix show. Oh yeah. I kind of hate wrote the first like three chapters really opinionated and then I totally stalled for almost a year actually.
Speaker 1 00:05:18 Yeah, I was gonna ask about your process there cuz so many people, you know, I've seen people start at the end. I've seen outlines just painfully long detailed outlines, book proposals. I, I think the, the O'Reilly proposal took me like a month and a half to get right. But you, I mean you didn't go traditional, so not a worry, right? But, but you just kind of started banging it out.
Speaker 2 00:05:39 Yeah, what I had, so I had done something in retrospect that was pretty smart, is over the past few years, whenever I responded in writing to a long, like a long, you know, 500 word, 1000 word response, whether it was to someone in an email, like someone asked me about how should I be thinking about hiring? It was a tiny seed founder and I wrote this really long email, grabbed it, threw it into a Google doc, and then every now and again I'll respond on indie hackers and sometimes it's short and sometimes it's really long, right? And so I started pulling those and there were questions like, can I compete in a really competitive space with big incumbents? And my answer was, yes, but here are three things to do, you know, here you can't just go unblind. Right? And suddenly I was like, huh, that's a nice little blog post.
Speaker 2 00:06:20 So I started throwing that in. I think I got asked about profit sharing equity and stock options in the tiny seed slack. And I wrote this what turned into a huge, you know, a thousand words. So I pulled that each of those things became the core of like a section or a chapter of the book. So I did, I started from there, I started writing, turns out I wrote about 20,000 words and then I scrapped about 15,000 of them because they were, it was all early stage stuff. It was nice to Oh yeah. But, but that's still, that's like another book that I think I'm gonna do. Cuz really this ass playbook is kind of like you've launched, you have weak product market fit, you're trying to strengthen it. How do you get it and scale up from there and scale up. I don't mean to a hundred million, but a million dollars, 5 million, you know, whatever your goal is. Yeah. And so I actually got stalled and then I hired a writing coach who really busted my chops and helped me, helped me get the rest of it done to, to about what, 45,000 words. So it's still pretty, you know, it's like 210 pages, which is about what I Yeah. Like to push out.
Speaker 1 00:07:12 Yeah. The and and the fun thing is too, you can, that expands the more graphs and pictures you've put in, right? So Yeah. Yeah.
Speaker 2 00:07:19 That would be,
Speaker 1 00:07:20 Have a door stopper if you want. Yeah,
Speaker 2 00:07:21 I know. Well that's, and that's the thing is I hate, I don't like long books. It's unusual that a 450 page business book needs to be 450 pages. Usually it's either padded with bullshit or it is the author not being able to kind of reign themselves in. There are some exceptions I will admit. So founding Sales by Pete Kaji, 450 pages, which for me, when I see a book that long, I'm like, warning sign, red flag, not gonna be good. I started to read through and I'm like, oh, it's, it's long because he covers everything. It's two books worth of material, you know what I mean? He just didn't, didn't break it up into two books. So there are exceptions, but most business books that go over two 50 or 300 pages I think, you know, should be trimmed. They're like, the director's cut and they should be trimmed by 30 minutes. <laugh>.
Speaker 1 00:08:05 No, I feel you on that. I mean I actually have founding sales right behind me and I, I keep looking at it and I'm like, do I really want to start this? This thing is huge
Speaker 2 00:08:13 <laugh>. Well I wouldn't, so I wouldn't read it front to back actually. And Pete, I interviewed him on my podcast and basically he's like, just go to the chapter that you need. It's more of a reference, not a reference like a dictionary, but like the, you know, the first chapter is like, I know nothing about sales, how do I do it? And then there's one about like building your deck and then there's doing a demo and it's like if you already feel like you're pretty good about that stuff, you can probably skim through it. But by the time you get to the last chapters, it's like hiring your first sales person, hiring a whole sales team, hiring your first sales leader, scaling a sales team. Like you don't need those yet. You know, so like I wouldn't, I wouldn't worry about reading the whole thing.
Speaker 1 00:08:45 Is that how you approach this one? Or is it you're an established founder, you're in this exact situation, here's how you go from, you're already at, I don't know, B or C, here's how you go to G or something.
Speaker 2 00:08:56 Yeah, that's really what it is. Mine is much less a reference cuz it is short. I mean you could read, I bet if you're a fast reader you could read this book in like four hours, you know, and I bet the audio book, cuz you're a little slower, will be five or six. Like it won't be that long. And the idea is to try, I was trying to communicate everything that I know about our types of SaaS companies, right? Which is, some of 'em raise a small amount of funding. It's not, not no funding, but it's not the venture track. And it's also not those amazing little lifestyle businesses that I wrote about and start small, stay small, right? Where it's like, I wanna cool little step one, like a Shopify ad on that gets to 10 k a month. Love those businesses. That's not this, there's a reason this subtitle is build in multimillion dollar startup without venture capital.
Speaker 2 00:09:36 Right? That's the point. And so it's exactly what you said. It's like if you've launched and you have some semblance of like, I've kind of built something people want, but maybe it's still a little fuzzy. Or if you're doing half a million a year or a million a year, I still think like the SaaS playbook has, cuz there's a bunch of stuff about hiring, there's stuff about expanding your marketing approaches. There's things about which metrics you should track. I'm pretty opinionated about that because so many founders don't want to track their metrics. And it's like, you should track something. Let's not go blind. You know, go in blind meaning, and cuz I've seen founders who who build up to half a million a year and they're like, I did it without any analytics. Just like Basecamp said, I don't even look at it. And it's like, well good luck when you plateau cuz you're gonna have no clue what was working and what wasn't. Right. Having some type. So that's the kind of stuff where like, I think at, at most stages, as long as you're in that, the tiny seed MicroComp, like mostly bootstrap SaaS mindset, I think there's stuff in, in here for you.
Speaker 1 00:10:28 I'm excited to check it out. I mean, uh, I read Blitz scaling and um, I got Ben Horowitz's book and, and uh, you know, I'll name all the other ones and the, the high growth mindset or whatever, but I, um, I can't remember the the writer, but all these are the lexicon is, is borrowing from what made Facebook successful. And you know what LinkedIn used and it's just not applicable to b2b sas. I mean, they'll mention they'll throw us a bone every now and then, but the lexicon is completely different. So it's kinda like you're reclaiming it, right?
Speaker 2 00:11:01 Yeah. I just want there to be a resource. Look, this will not, and this won't sell us as well, I won't sell as many copies as the books you just named because those are more applicable to the broader venture space. The venture space is bigger than our space. Yeah. And I, I'm under no illusion of that. But what I wanna do, much like with my prior books, they're, they're niche focused, but I want them to be best in class, you know? Yeah. Otherwise I shouldn't put it out. And so yeah. I do want, there isn't a resource like this as playbook. That's, if there was, I wouldn't have written it. So funny story actually about let's say 10 years ago, I don't remember exactly when it was, I had this whole outline for a book and I was like, what if there was a book where each chapter covered one like marketing approach that I know of Right?
Speaker 2 00:11:42 Mostly, mostly b2b basically. And each chapter had like a case study or how to do it or how to think about it. 20 chapters ish. And I started pitching it to a friend. He's like, I love that. That's the most do that, right? Yeah. So I started thinking about it, I started hashing out how I was gonna do that. There were some limitations cuz I didn't know all of them. And the leap that I didn't make was to realize, well I should have just interviewed people who were good at each of those. Right. For the other chapters within six months a year Traction by Gabriel Weinberg came out and that's exactly what that book is. And I was like, thank you, thank you for making me not write this book. So it, there was already a perfectly Right. So then I didn't try to write a similar book similar with SAS playbook.
Speaker 2 00:12:23 Like the stuff I put in here is not, is not anywhere else. I mean maybe it's in some YouTube videos that I've recorded Right. Or some of my podcast. But like, it doesn't just borrow from like other people's work and it doesn't borrow from one success I've had. Right? It's either the multiple successes I've had or it's the, um, you know, I'm invested in like 149 SaaS companies now, right? And across tiny seed and, and privately. And there's just a ton of examples in like learnings and frameworks and rules of thumb that I'm pulling from, from that corpus. That's where perhaps it's a unique take. And if, again, I don't, I hate saying stuff like this cuz it makes me feel weird. Cause I'm tend to be pretty humble. But like a friend of mine said, it's the same one who talked me into writing it. He said, our community needs this book. Like, as I started describing it to him, he's like, you need to write this because there's nothing out there like this. Right? And so that's where I was like, all right, I ha I have to do this. It really did feel at a certain point like, yeah, I will regret not doing this. You know,
Speaker 1 00:13:16 And that's the kind of stuff that sustains you through the, uh, the middle, messy middle of writing a, uh, and throwing out 15,000 words, you know? Yeah, I know that. Ping,
Speaker 1 00:13:29 Let's take a little break to tell you about Turnkey. The ones making this podcast happen. Now. I think turnkey's awesome, but I am super biased because I'm a co-founder. But I love what we're doing for subscription companies. You might look at your churn numbers and think there's gotta be a way to turn this around. There's gotta be someone who can improve retention and help us track down why people are leaving your product. And that's why Turnkey's here, Turnkey's the only platform that fixes every type of churn for you. We handle retention for customer obsessed teams like Jasper Fair Drop, AI, dungeon and Casto. We lower cancellations by up to 42%, recover up to 89% of failed payments and even increase customer LT v by 28%. And we do it with our user-friendly, customer centric, cancel flows, modern failed payment recovery and AI driven feedback analysis. So if you want to run a healthier subscription business, head to turnkey.co to get started. Is there a reason why you went Kickstarter and not like a traditional book deal?
Speaker 2 00:14:32 Yeah, yeah, there is. Well, so I wouldn't do a book deal because I mean, book deals, they're rough these days, man. Um, they are, I know you published, you know, 7, 7, 8 years ago, but even my wife went through a publisher for her most recent book called Touching Two Worlds. She and I self-published her first book, which we co-wrote together. And then she went through a publisher and frankly they didn't do much <laugh>. Yep. They just didn't do much. And they, you know, and your royalty is, I don't, what is it 7% or 10%? I have all the reach into this audience, right? Right. I have tens of thousands of people on email, on YouTube and, you know, whatever. So I had no desire to do traditional. The the real choice was do I just publish it? Like say start small, stay small. My first book I self-published through Amazon Print on Demand, but I, I launched it to my list with just a landing page and I said, pre-order the book or pre-order two of 'em.
Speaker 2 00:15:22 You know, it was just a very simple kind of, here's a landing page Stripe link Yep. To, to pay for it versus Kickstarter. That was my real debate. I wanted to do Kickstarter one because I like doing new things and I wanted to see is this a good decision or not? I love learning, right? I'm a founder, right, right. So I gotta, I gotta keep doing interesting things. So that was one decision. Second part is I really did want a bunch of tiers and the more I went into it, the more I realized, you know, $30 tier for just the book plus, you know, the physical copy plus an ebook version all the way up to 5,000 to come hang out with me in Minneapolis this summer for a couple days, found a retreat and there's like seven or eight tiers. And the further I got into it, I was like, is there a platform out there that makes this easier?
Speaker 2 00:15:57 Because that's gonna look really weird on a landing page to have eight tiers. You know? And then even pre-ordering, like there's questions about the legality of taking someone's money and then shipping them a book six months later. You're not kind of not supposed to do that with credit cards. Right. <laugh>. So, and at the time we were gonna print in Hong Kong and it was gonna take six months. I later we're gonna print in the US now, but it's uh, cuz for time it's twice the cost, but it only takes like six or eight weeks. So we did change that. But that was another thing is like, is there a platform out there that's designed for pre-ordering? You know, and that, that became another aspect of it.
Speaker 1 00:16:30 Right? Yeah. And you got the flexibility of, of the bundling. Like I had to Yeah. I want you to do the bundling as well. And I had to do become my own reseller through O'Reilly.
Speaker 2 00:16:40 Yeah. Cuz they don't want you to Right. To bundle the audio plus the this or the Pia or the Kindle or whatever. Right. Absolutely. I that, that amount of control drives me nuts. And in fact, friend of mine just wrote a nonfiction book in the startup space that you would know the name of. I don't wanna mention it here for obviously for what I'm about to say. But he was super frustrated because he was like jealous cuz I, he's like, you're doing a Kickstarter, you're doing bundles. Yeah. You're doing, and I was like, yep. And he's like, I can't do any of that. They won't let me, you know, cause it's a major, major publisher. So. Right. I would've a tough time I think dealing with that. No. If I didn't have the audience in the space, you know, whatever. Right. I would hope they would help me. But it's like that's, I was able to hire a designer and hire a copywriter, you know, and hire a videographer like everything I needed to do. Again, being a startup founder, like you just kind of get it done. It's just another project.
Speaker 1 00:17:26 Right. Totally. Speaking of audience, I want to talk about, I mean, you're a one man media machine and it's constantly impressive to me. You're consistent, sustained output. I mean like how many hours per day are you recording or writing? <laugh>
Speaker 2 00:17:42 <laugh>. It's a funny question. Uh, this week a lot because, so here's the hardest part, man. So you're right. 52 YouTube videos a year that are basically me in front of a camera, 10 to 15 minutes each, 52 episodes of startups for the rest of us, which is me for full-time, 30 to 40 minutes and then 52 episodes of the MicroComp podcast. But that's just, I do intros and we pull in audio from other things, but I still have to record intros, you know? Right. And then there's about 10 to 12 episodes of Tiny Seed Tails a year, which is actually pretty involved. And then interviews like this. Right. So the hardest part for me is when I, if I take a week off, like next week I'm in London, well I'm not off, but I'm doing a MicroComp local and then a tiny seed kickoff.
Speaker 2 00:18:22 That's when I have a lot of time this week. Right. Cause I have to, I have to make up for that week. I can't, I can't miss it. Right. Um, in a standard week, man, honestly, startups with rest of this episode, one hour tops and that's it. Right. If and if it's a solo episode, it's almost live to tape. You know this so where I'm just talking. Wow. Yeah. I mean there's editing involved, but I pretty much, usually I have a whole tr Right. I'll have these topics that come to me during the week when I'm listening to other things and then I just go through them, the listener questions q and a, people are surprised. I, it's rare that I review the question before I read it live on the air. Like that's at the level. Cause I'm, I'm almost 700 episodes in. Yeah.
Speaker 2 00:18:56 So it really has become, I wasn't like that when I started, you know, but I've been doing it now for 12 years. So it's a few hours a week. It's probably less time than you would think. The YouTube videos usually spent 20 or 30 minutes outlining and then almost live to tape with mess up. So if it's a 15 minute video, I usually record for about 20. So it's like an hour for one of those videos. Now when I started doing this, like YouTube especially six hours, seven hours for that, like it would eat a whole day to record one. Yeah. It was crazy. And I was terrible at it. And the lighting's off and my performance is bad and, you know, all the, and the videos aren't that great. Yeah. But oh, we got like a hundred subscribers this week. That's cool. Like a hundred more people might hear about this, you know, and then it rashed up now it's like right at this moment it's like a thousand new subscribers on YouTube every 4.5 days. That's been our cadence this year. It's just bananas.
Speaker 1 00:19:46 That is, that
Speaker 2 00:19:46 Is, and that's how I keep the motivation, right? Yeah. Because what we're getting at is like, how can you sit in front of a camera this or a microphone this often, you know, for that much time. It's because the feedback, it's not, if no one was listening, I would've stopped.
Speaker 1 00:19:58 Yeah. I mean, and I, I admit this is like a bit self-serving cuz you know, obviously the context here, but I, I completely agree. Like the, the immediate feedback loop would be so nice to get. Cuz it's just, it's just, I mean it's human nature. It's dopamine hits, it's, oh wait, people are actually getting value out of it. So Yeah. Are you optimizing that channel at all a thousand sub subs every couple days or few days? We
Speaker 2 00:20:21 Are. I mean we're, yeah. We're optimizing it. Yeah. Yeah. We, we went from publishing long form videos on our YouTube channel. So you go to go to microcomp.com/youtube if folks are interested in seeing it. And if you go way back, you'll see we published our conference talks. We had all this great content, Jason Cohen, Heaton, Shaw, Stelli fd, like just SAS luminaries, right? Yeah. And we would publish this 40 minute talk from them that was just so good. And it would get 500 views, 750 views. And I'm like, this deserves so much more than that. The problem is those are, those are not YouTube native YouTubers don't tend to watch long form talks are slow to get going. You're clapping, you walk on, Hey, I mean by the time the content starts, you're two minutes in. No one on YouTube has time for that. Right? No.
Speaker 2 00:21:03 So we did, we hired a consultant and we started really doubling down. And she was like, you, if you're gonna do this, you gotta go to YouTube native. You cannot repurpose stuff. Cause we also tried to repurpose podcast interviews, startups, the rest of us interviews, even tightening them down, you know, cutting 'em from 30 to 15 minutes. She's like, yeah, still not really there. So that was when she started saying, here are the types of titles you need to use. Here are the types of thumbnails, here's the types of descriptions, and then you need to record good video content. Mm-hmm <affirmative>. And that last part was the hardest was just figuring out how do I, how do I get good at this? Cuz I was not, and that was just reps. Right,
Speaker 1 00:21:38 Right. And I remember you telling me that. It even comes down to the thumbnail, you know, and, and the, the title. You gotta kinda just like be immersed in the the YouTube culture. Yeah. You know? Yeah.
Speaker 2 00:21:48 It's like SEO where if you're really good at seo, you just, you start getting this sense, right. And you go to hres and SEMrush and you're like, I kind of know how to target this keyword. Like in YouTube it's similar. We could have learned it and in fact I started learning it and then at a certain point we're like, oh, we found a consultant who's better at it than me. And they're not that expensive. You know, like, I'm gonna, right. We're gonna hire them to help us instead.
Speaker 1 00:22:09 So is YouTube now one of your, your biggest channels? Or like, I remember you mentioned reels a few months ago was taken off a bit.
Speaker 2 00:22:16 Yeah. Is that the shorts? YouTube shorts? Yeah.
Speaker 1 00:22:19 Yeah. Oh yeah, yeah, yeah, yeah. I'm messing up my
Speaker 2 00:22:22 Uh, I think Rio's Instagram. I'm not, yeah, I'm not super social media so I don't actually know all the difference. Um, yeah. Shorts have not performed well for us, but that's probably a separate discussion. Yeah. YouTube is certainly our fastest growing right now and it's that interesting thing. But I would say that the podcast startups of the rest of us is the still continues to be the most engaged. Cuz it's 30 minutes, just me and you and you're doing the dishes, whatever you d if the first few minutes are boring, you probably don't skip the podcast. You probably give it a few more minutes. If the first 20 seconds of my YouTube video are boring, you probably skip me because you have a hundred more in your queue. So it's much more, I'm one of many in, in YouTube in addition. Like if I say, all right, 25,000 subscribers to startups, the rest of us 20, 20 to 30, it's really hard to know for sure.
Speaker 2 00:23:08 But let's say that's the number. What I mean by that is I received 20 to 30,000 downloads of every episode new within X amount of months. Right. So subscribers kind of means downloads, which let's say means listens. It won't exactly. But we'll just say means. Listen, when I'm on YouTube and I say we have 52,000 subscribers, which I think is probably what we have today. If I put out a video that doesn't kind of catch the algorithm, it gets like 1500 views or 2000 views. Wow. Does that make sense? So it's very much YouTube starts by showing it to probably our most loyal subscribers or whoever's online at that point. And if the engagement's there, cuz YouTube makes ad, makes ad revenue, so you need engagement, otherwise they don't make the revenue. So they start showing it to people and if it catches with them, they show it to more and more and more. And if it doesn't, they just shut it down. So you can have this big subscriber base and just have low view counts If the video, each individual video doesn't perform. So it's much harder.
Speaker 1 00:24:02 Wow. And then you just toast. Like it's, it's like a dead asset move on.
Speaker 2 00:24:05 Pretty much. Yeah. Yeah. So luckily we don't have too many of those, but um, yeah, it it's just a different, yeah, it's a different game. And for us it's new. I mean we're only, you know, we've had the YouTube channel for two years but really did the double down and started recording a, a new video every week like just about a year ago, maybe 14 months. So I kind of still feel new to it, but definitely seeing growth there that I haven't in other channels,
Speaker 1 00:24:28 Are you still seeing growth on Twitter?
Speaker 2 00:24:30 I think the, the most recent couple things, I had a couple tweets that kind of went viral and then I, the SAS playbook launch for the Kickstarter I think added a few thousand. And I only have like, I don't know, 29,000 or something. 28, 20. So I'm not a huge, it's not like I have a huge account, but I think I added 10% more, which is probably the single event that has increased my Twitter following like by the most in, you know, since I signed up for it. So I'm still seeing increases. I'm not on Twitter that much. I mean, I'm on a couple times a week and that's fine and I respond, but like, it's not my game. Right. I wish I didn't have to be on it is my honest, honest answer. I don't love Twitter, but it is, I'm investing in startups. I have a community and an audience. So how can, and it's tech, how can you not be on Twitter? Right. You know? Right.
Speaker 1 00:25:13 Well that means you're on Blue Sky now too, right?
Speaker 2 00:25:15 Not yet, but uh, I am what's called a, let's see, remember the early adopters, you remember crossing the Chasm? Mm-hmm. <affirmative>. Yep. There's like the, I forget what they all are. I'm definitely not a laggard, but I'm kind of the early majority probably I will wait. Like I didn't sign up for Mastodon cuz I was like, I don't think it's gonna work. And turns out probably right, but not, it, it's not gonna work is usually the right answer with new social networks. <laugh>. Cause most of 'em don't how you think of Clubhouse, you think of um, what Te Periscope and the, you know, the, those ones that were fighting that out a few years ago. But here's the downside to that is like, I heard about Twitter in 2007, right when it was early and I didn't sign up till 2009 cuz I was kind of like, eh, don't really wanna do it. So I did miss out on early growth. There's a reason I only have 20, you know, 29,000 followers, is that I probably missed those first two years of growth. So if you vouched for Blue Sky, I'll think about signing up, but until then
Speaker 1 00:26:08 Yeah. It, it, it feels like the Wild West. I mean, it, it's almost like Jack reliving 2006, but with Better Tech, you know? Yeah, yeah. And is, if it's any constellation, I signed up for Twitter, I think in oh six. Wow. And I'm like, user 6,000 and I only have 6,000 followers. So <laugh>
Speaker 2 00:26:26 All right. Well
Speaker 1 00:26:26 I did, I did something clearly did something wrong there. Right. I wanna shift to just media in general and how it applies to, to SaaS and, and this whole notion of marketing like a media company. I think HubSpot wants to claim that they, they coined it, but I'm sure it's been around longer. I mean, do you think this is still a good approach for B2B SaaS and growing mind share and distribution and all that?
Speaker 2 00:26:49 Only if you have millions and millions in the bank. I think if you've raised 10 million and Yeah. And you know, at a high valuation and you have, you can hire a media team. Yeah. You know, to produce amazing YouTube content. Now think of HubSpot did this, right? They bought the hustle and then they've kind of always been inbound marketing was their big thing. Dharmesh blogged and then they created a video. They're, they're good at it. Rand Fishkin did this with s ema with his Whiteboard Fridays really good stuff. If you go back and watch it. Chris Savage with, or Wistia in general, right? They did a lot of this. They are a video company. So realistically they should have been, what's the commonality in all those companies? They all raised cajillions of dollars, right? Right. Like MAs raised, I don't remember what the number is, it's like 30 million maybe, and Wist are raised 15.
Speaker 2 00:27:34 I don't know, it's a lot. And Wistia specifically is in the media space, right. So it makes sense that they would, right. They were video hosting. So I think if that's in your wheelhouse and you're really good at it, fine. It's much like freemium, like having a freemium model where like it pushes revenue down the line. Talk about five stages of awareness, you know, of like, hey, someone's like not even aware they have a problem and then they're aware they have a problem and then they're aware that there are solutions and they're aware of your solution and then they're an expert, right? Media company is like the very first stage, not even aware you have a problem. We're just gonna talk about startups. Like, you know, you're turnkey, right? It's like, yeah, we're churn software, we're solving it for subscription, you know, for subscription companies.
Speaker 2 00:28:11 But you could go write articles about entrepreneurship in general. Here's how to become an entrepreneur. Like that is what being a media company is like is, it's so far up the funnel. It's not that you shouldn't do it, but there are, if you're a bootstrap founder or you have half a million in funding or less, you have much, much more important things to be focused on than going and dumping a lot of money into this. I'm not saying don't start a podcast cuz I do, you know, you obviously have a podcast. User list, has a podcast. There's a bunch of tiny seat companies with podcasts, there's some with YouTube channels and they are interesting channels. But stay close to the money in terms of you wanna be lower down in that funnel or lower down in the awareness. Meaning, you know, not producing, uh, I guess it's like, you know, Netflix type content, which a lot of, like, a lot of Wistia stuff was very like a lot higher up in the funnel. And same with, same with HubSpot, but they can afford to do that. Right?
Speaker 1 00:29:00 Right, right. It's not, it's not just two or three or four people talking into a camera. It's, yeah, there's camera movement and you have a set and all that stuff's
Speaker 2 00:29:08 Expensive and it's time consuming and it's amazing content. And over years it will build a brand and it will push customers. But when you're at 5k, m r r 10 k m r R and you're trying to, it's like, no, no, no. Do marketing <laugh>, do outbound, do pay-per-click, do seo, do you know, whatever it is go to in-person events. Like there's way better B2B marketing approaches for small scrappy companies. Small then becoming, you know, becoming a media brand. But becoming a media brand is fun. Especially for, you know, if, if you wanna do it right. Like that's, that's the fun part. And that's the, it's the spinach is your pay-per-click ads and your, you know, whatever else. All the grindy marketing approaches that actually move the needle and ice cream is, I wanna get on a microphone and record a YouTube video. You know, and that's, it's, it's a siren song. Yeah. And
Speaker 1 00:29:52 Buying the new gear is fun and Oh yeah. You know, all that. All the shiny bike syndrome.
Speaker 2 00:29:56 Right. Exactly.
Speaker 1 00:29:57 I wanna talk about Drip and how distribution when you were running Drip is different than, or the same as distribution today. I mean there, there's the, like you mentioned the, the template or the pressure or the coming from, you know, HubSpot and the media company crew. But I mean, did, did you approach distribution with the R framework at Drip? Or was it your own invention? I'm, and I'm sure you've written about this and I missed it.
Speaker 2 00:30:24 Yeah, no, that's fine. I mean, for folks who don't know, drip was a SaaS app that essentially became kind of an email marketing tool like MailChimp and then it became marketing automation like Infusionsoft or even like HubSpot has a lot of marketing automation and I grew that, bootstrapped it to 10 employees, sold it in 2016. And we had a lot of success. We were growing fast. We always to commented, cuz I had startups with the rest of us at that time and I had MicroComp right at in-person events, a community and such. And I would talk with my team, like, should we start a drip podcast? Should we start a drip in-person event? And we ne and I was always like, this is not, there's no ROI here for us. Y'all Like we we're gonna get so much more leverage out the big five, big five marketing approach is what I call them.
Speaker 2 00:31:04 And these are the five most common B2B SaaS marketing approaches. It's content, seo, cold outreach, integrations, partnerships and ads. And usually pay-per-click, right? Usually it's Google, sometimes Facebook or Insta. Those were the first five that we dove deep, deep into with Strip. And that provided the vast majority of our growth. I also did, I had a little bit of a personal brand, not like I do today, but I did podcast tours and you know, I would go on shows and stuff to promote it. But realistically our content, our inbound cold outreach was break even for us. It was not a huge mover, but our integrations were huge. We did 30 something integrations in about 18 months and really drove a lot.
Speaker 1 00:31:43 Oh that makes my, that makes my head hurt 30. It
Speaker 2 00:31:46 Was, it was nuts. But we got really good at it. We had one guy, Ian, who could do an integration in less than a day at a certain point, as long as the API was good, we had the whole framework built such that it was like plug, plug, plug, get a few points in and we'd launch a V1 integration with it. Like wouldn't have OAuth, it wouldn't have all the end points, but we're like, let's see if anyone uses this and the key, let's co-promote, right? So we would reach out that, would we do that first? Actually we, someone requested Send Owl, right? Which is like a kind of, I think like a Gumroad competitor. And so we'd reach out to Send Owl and we're like, Hey, we have like 10, 15,000 on our email list, would you be willing to co-promote? And that was a huge driver of momentum in the early days.
Speaker 2 00:32:24 So all that to say, your question was, do I market, you know, do I spread the word about micro conf and Tiny Seed in the same way we did Drip? And it's like, no, cuz Drip is B2B sas and if you're doing B2B sas don't, don't be a media company if you're starting a startup accelerator and a community online and in person like MicroCon become a media company. Yeah. Like that's the best way. Or if you're selling info products, honestly, you know, like, oh yeah, people should know, like, and trust you build an audience, it's great. But like B2B SaaS is, is not, I don't, I have this number of the companies we've funded at Tiny Seed through the accelerator, less than 5% had any kind of audience before they got successful. I think it was like 4.5%. Like it's a tiny, tiny number. But when you go on Twitter, it seems like everyone who's successful has anu. Right. It's like this weird Exactly. You know, survivor ship buys is not the right word, but it is a weird kind of obfuscation of what's actually going on there.
Speaker 1 00:33:15 Projection, right. You know, or in some way. So one, one thing I love about your advice is that you are willing to be vulnerable in how you deliver it. So we send you investor updates every month and sometimes we'll say, eh, I'm feeling a little burned out right now. And you're like, guys, take care of yourself. Take it seriously. And you opened up about this, I think pretty recently about after you sold Drip and your biggest regret was you didn't take care of yourself, you didn't sleep, you didn't exercise, you know, managing emotions. What does taking care of yourself look like these days for someone who's building a, a business but also maybe, maybe you're just, maybe you're not the founder, but you're an operator, have, have things changed there? Are the basics the same? Any new fancy tools you're using for that? I, I don't know.
Speaker 2 00:34:02 You're right. With Drip, I almost kind of imploded both personally and then almost imploded my family, you know, which is unreal. Such a, such a weird thing because my whole goal, my like three guiding tenets for my professional life are, I want freedom to work on what I want. I want to have purpose to work on really interesting things. And I wanna maintain healthy relationships, freedom, purpose, relationships. That's my, that's my mantra. And yet there I was basically unraveling, you know, the third one, once I sold Drip and left, I made the decision that I would never get myself back into that hole again. The whole of burnout and the whole of just unhappiness and grindy. My business was growing 17% month over month for 20 something months in a row. It's like the absolute Cinderella story of what everyone wants. Yeah. And I was fucking miserable, you know?
Speaker 2 00:34:49 And it's like, how, how did I let that happen? That's what I always wanted. So these days, I mean you laid out the fundamentals. Honestly, sleep is a big one, right? I now, I sleep eight, nine hours a night. I exercise twice a week, which I didn't do for like a decade. And then the third thing for me was I started going to therapy pretty intently like twice a week for a while until I could, I could pull myself out. Cause I was in a head space that, you know, man, I don't know if you've ever experienced any type of depression that lasts for a while or, or like high, super high anxiety where you're almost like, I might need to be on medication. Like to that point or just any, any of those things. My dad has o c D really bad. So that's in our family, like any of these kind of mental illnesses I'll say, they almost warp your perception of reality a bit.
Speaker 2 00:35:32 And they warp your perception of yourself. And that was something I had to like, how do I get back to who I actually am so that I can see my, my relationships and I can see myself as who I actually am instead of this negative view of everything. So I went pretty intently into therapy. And then during that time I realized like, I can do whatever. I can retire, never work again. Right? And I realized if I'm going to work again, I can never be this upset. I can never put my family through that. I can never put myself through that again. And so I made a decision at that point and it was a willpower decision. I was, I was not burned out anymore. And I had stepped away and I just said, I'm not gonna be stressed about things anymore like that. So like svb, good example, I used to be stressed about everything all the time.
Speaker 2 00:36:17 I turned every speed bump into a roadblock. Just was this catastrophe. Oh my god, Russian spammers act, us <laugh> we're done, the company's done. And then we'd fix it in two days. But I would have two days of just sleepless nights and just misery that I put, I inflict it upon myself and I realized, no, I'm doing this to myself. And so like four or five, well maybe it's two months ago now, Silicon Valley Bank implodes, we have literally millions and millions of dollars there. <laugh> and a and r who you know, is, is texting me. He's like, oh my God, this is so stressful. And I'm like, yeah, we'll be okay. You know, I'd, I just made that, it's almost like a, if you've seen off office space where he gets hypnotized, you know, and then they snap, right? And he's like, I don't care about anything.
Speaker 2 00:36:56 And suddenly his life was great. Mine didn't happen that suddenly. But I did have to step back and say, don't be dumb. Like you're being dumb. You're, you're let, and this was through therapy and my therapists telling me this, but it's like know you're manufacturing a bunch of shit that isn't real. And now what I see it's real is like, I'm gonna be okay because I always figure it out. Right? That's kinda how it is. It's almost like a little, a little mantra. So even though today we deal with way more money, way more risk, I talked to founders about getting sued, being hacked, we receive, you know, ourselves cease and deci, you know, we, the stakes that I'm at now are way more, yeah. Way higher than they were then. And yet I'm just like, that's okay. It'll be all right. So it was a big mental shift for me that, you know, hopefully if you feel like you're where I was, you know, if you're listening to this and you're where I was a few years ago, that it's like, get help man. Cuz I didn't, I didn't until 2018, which was mm-hmm. <affirmative> just years, you know, years later,
Speaker 1 00:37:47 Man, that's, that's so powerful. And I'm frustrated that there's such a stigma around mental health and therapy. I've been in therapy, I dunno, I went for four or five years after we were the first acquisition Tinder made. And that whole journey was like very taxing. And then suddenly you're thrust into this environment that you have to figure out how to navigate on the fly while performing. You know, it just wrecked me. I gained like 30 pounds, you know, just self-destructive behavior. And it was therapy that brought me out of it and saved my relationship. So double recommendation for therapy. Yeah. I would not be married with kids today or doing turnkey or doing this if I hadn't done it. So yeah, it's pretty incredible. Yeah. All right. We're almost at time. Two final questions I wanna ask you. The first one is, what's something you've read lately that's had an effect on you?
Speaker 2 00:38:36 I was super impressed with Dan Martel's book, buy Back Your Time. Oh, I've read a lot of, that's a lot of time management books. And Dan himself was a startup founder. And this is specifically for founders and I, again, I go into these books skeptical, usually most business books are not good. And I have a pretty high bar. I started reading it and I'm like, this is super detailed. It is not the high level BS that a lot of business books are to the point where he's like, hire an assistant and here is my exact system in labeling scheme in my Gmail account that she uses to triage all my emails. And I'm like reading through this with diagrams. I'm like, this is gold. So I Oh, that's awesome. I was impressed with the quality. It actually made me up, you know, I was just finishing Sass playbook when I read it and I was like, oh, this pumps me up. I need to, I need to do even better. Cause it's, it's just a really, it's a really well written book.
Speaker 1 00:39:27 Oh yeah. I'm gonna check that out. And then what's the craziest thing you wish you could do right now, but probably can't.
Speaker 2 00:39:33 I think that I could kind of go fully remote and just travel perpetually, you know, especially when it's cold. And here in Minneapolis where I live, maybe I don't wanna be on the road all the time, but I would love to be on the road quite a bit. But frankly, my job <laugh> being in front of a camera every week, you know, and, and on the mic. And then I do have a family. I have kids, you know, teenage kids that are in school and I don't feel like they're keeping me from that. But I definitely feel like it would be, it would complicate my life in a way that I, I don't want the complexity and my youngest moves out in five years and maybe my wife and I'll, uh, we'll do that when the time comes.
Speaker 1 00:40:11 Rob Walling, unleashed,
Speaker 2 00:40:13 <laugh> on the world. I'll just show up in a city and be like, let's hang out <laugh>.
Speaker 1 00:40:18 I love it. All right, thanks Rob. Good to see you, man. Appreciate you coming on.
Speaker 2 00:40:22 Always, man. Thanks for the invite.
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