Rob Walling On How To Podcast For 10 Years Straight

Rob Walling On How To Podcast For 10 Years Straight
Rob Walling On How To Podcast For 10 Years Straight

Jun 11 2020 | 00:34:59

Episode June 11, 2020 00:34:59

Hosted By

Stuart Barefoot

Show Notes

Motivation is a fickle thing. Some days it’s front and center, driving you to produce your best work. Others it’s no where to be found and things that used to be a priority can fall to the wayside.

The rollercoaster of motivation is a central theme in our latest episode of Audience. Craig sits down with Rob Walling, found of Drip and TinySeed, who has produced over 500 podcast episodes. His show, Startups For the Rest of Us, has been on the air for 10 years. Throughout that time, the show has experimented with new formats, went from co-hosts to a one man show, and spurred a successful live conference series.

Given Rob’s passion for and success with podcasting, he’s just the guy to help you maintain or re-spark your motivation. Throughout our interview, he describes his biggest podcasting regret, how to talk ad nauseam about the same topic, and why fostering a community with his listenership is his biggest legacy.

Listen to the full episode to learn how a podcaster with 10 years of experience under his belt finds the motivation to keep going.

How Startups For the Rest of Us Has Changed

A lot has changed in the podcasting industry in 10 years. And the same thing can be said for Rob’s podcast, Startups For the Rest of Us.

Starting out, Rob describes feeling nervous behind the mic. He wrote out, word-for-word, a script of exactly what he wanted to say for each episode. It took about 250 recordings to find his voice and feel more comfortable talking candidly with his co-host. And then he and his co-host hit the complacent years. Both in the midst of building their start-ups and family life, they stopped experimenting and trying new things. They still showed up each week, but had lost the motivation to innovate.

It was just within the last year, at episode 448, that things started to change. His co-host, Mike Taber, decided to take back from recording every episode. And with that shift, Rob rediscovered his motivation to start innovating again.

He ushered in new formats, more experiments, and pushed the show to excel beyond its original success. Now surpassing 500 episodes, Startups For the Rest of Us continues to inspire bootstrapped entrepreneurs.

Talking About The Same Topic For 10 Years

After settling on a podcast topic, the realization that you may be talking about same subject for years to come sets in. If you’ve taken the advice from successful podcasters, you chose a topic that you’re passionate about. But how do you find new ideas and angles about the same general topic week after week?

Rob’s advises to “peel the onion”. The podcasts that make a splash bring new perspectives and voices to the table. Your focus, whether you’re on episode 10 or 100, should always be how can I add something different to the conversation?

For Startups For the Rest of Us, Mike and Rob started building episodes from content they’d previously written about in books and articles. But then episode 30 hit and they ran out of things to say. That’s when they realized listeners had submitted questions via email and Twitter that they never addressed. A new episode format was born and they continued consistently publishing new material.

In the years when their other professional ventures dominated their time, they reduced how frequently they published episodes. Moving from publishing weekly to twice a month helped them stretch out topic ideas. But as growth stagnated, they realized their audience was engaging less.

So they moved back to a weekly schedule with a new found determination to support their loyal fanbase. By introducing expert interviews, roundtables, and hot seat formats, they continued to dissect their entrepreneurial niche by focusing on under-represented points of view.

Our main takeaway from Rob’s answers is the idea of experimentation and innovation. He says he’s not afraid to try new things because it’s not permanent. You can always revert back to what was working before. But when you stop trying new things and put the show on auto-pilot, you’ll inevitably bore longtime followers.

How To Experiment With Podcast Format

Mixing up content styles and formats is a popular way to keep an audience engaged. But what’s the best way to approach it without alienating listeners?

Rob and Craig share the same process because they’ve each found transparency to be key. The relationship between podcaster and listener is a two way exchange. In order to honor that connection, start any format experiment by telling your listeners what to expect.

We do this with Audience when switching between interviews, monologue episodes, and answering listener questions. The new format is explained in the prior week’s episode and again at the top of the affected episode as a reminder. Being transparent can also help with building out the new format you want to try. If you want to include listener participation, put out a call-to-action in previous shows to get more submissions.

Once a new format airs, the work isn’t done. Look to your podcast analytics to gauge how the episode performed. Did total listens remain consistent? Did people consume the entire episode? Did your subscriber count increase?

And don’t be afraid of talking to your audience directly. Rob recounts a time chatting with a regular listener. He asked for their constructive feedback about the new formats he was testing. Up to this point, Rob told his listeners he was following a content calendar to rotate through multiple styles. Thinking the schedule would be beneficial in managing expectations, the feedback he gained said the opposite. The listener said liked the episode variety but he preferred when Rob went rogue and didn’t follow the rotating schedule.

Feedback in hand, Rob realized he didn’t have to follow a methodical calendar. His audience was ready for more variety and came to enjoy it more than his old approach.

Advice For Beginner Podcasters

There’s a lot to learn from someone who has been podcasting for 10 years. Starting when the industry was just emerging and creating two new shows within the last year, Rob is here to stay. But what advice does he have to beginners?

He starts with the biggest misconception. When he hears people say the space is too crowded, he has a rebuttal. He says there’s always room for novelty, innovation, and opportunity for new perspectives to speak on evergreen topics. If you feel there’s a gap in a niche, go for it but ask yourself how your show is different.

Begin with picking a few shows or interviewers you want to emulate in tone, style, and format. Use your favorite episodes as inspiration and a starting point to find your own voice. There’s no shame in paying homage to the podcasters before you.

Rob continues on this point. He says, “If I were to start from scratch today, I would cut my teeth with a hobby podcast that’s aimed at a super tight niche. Like a B-tier TV show where no other podcast exists, and you can watch the show as it comes out and talk about it. Learn how to edit and learn how to publish. And people who like that show will rally around it and find your feed.”

Resources Mentioned In This Episode

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Episode Transcript

Speaker 1 00:07 Hello. And welcome back to the audience podcast. I'm your host Craig Hewitt from Castillo's this episode I'm joined by Rob walling, founder of drip, the popular email marketing automation software, and more recently the founder of the tiny seed startup accelerator program, which Castillo's participated in last year. Rob is also the host of the startups for the rest of us podcast, which talks about online business, entrepreneurship, and software. And they're currently celebrating their 500th episode, 10 years of podcasting. That's a lot, uh, no matter what space you're in or where you're coming from. And Rob and his cohost, Mike have learned a ton about podcasting and those 10 years of, of doing the show. And this episode, we talked through a lot of those highs and lows and the things they've learned, both good and bad, and those 500 episodes. And I think there's a lot here for all of us, whether you're just a beginner podcast, learning how all of this works, or whether you've been doing a show for a while and are looking forward to your next hundred or 200 or 500 episodes. Speaker 1 01:09 But before we dive into the episode, I wanted to make an announcement about some things that are going on here at Castillo's. I wanted to share some good news that we're currently hiring. We're looking for someone to join our team as a director of podcast or success you might ask what is a director of podcast or success. And that the short answer to that is it's somebody who talks about podcasting. A lot. This person would, would run this podcast. They would run our YouTube channel. They would create a lot of content for our blog to help podcasters be more successful, whether those are people who are just looking to get into this medium people who are using our tool and wanting to be more successful with it. People that are looking for advice about how to run their show, how to monetize it, how to grow their audience and of every aspect of, of being a podcaster. Speaker 1 01:54 Uh, the person in this role and our company will be there to help support and encourage and guide pod-casters all along their, their journey. And we're currently accepting applications for this. If you head over to <inaudible> dot com slash jobs, you'll see the job posting for this role, and I'd love for you to check it out. And if you have any questions, please let us know. We're currently accepting applications and will be for the next couple of weeks. Uh, and we'd love to hear from you if you think that you're a good fit for this role. Uh, we'd absolutely love to hear from you <inaudible> dot com slash jobs to check out more about our director of podcast are successful. In the meantime, I hope you enjoy this episode with Rob walling from startups over the rest of us. Speaker 1 02:41 So Rob 500 episodes, uh, I'm, I'm really kinda envious. I mean, we've been at this show for a while now and my other podcast has 220 episodes. So I may be halfway there across my whole portfolio, but I mean, 500 episodes is, is a mountain of work, uh, for you, your cohost, how does it feel now to do the podcast versus not at the beginning, but you know, halfway through the journey has a lot changed in the last half of your kind of podcasting life. I feel like it's a bit surreal to even say 500 episodes. You know, this is it's like anything you do for a decade, you just kind of at a certain point, accept that. That's just what you do. And you just show up every week and you talk and you ship this thing into the world. Um, I think that, I think the biggest change in the past five years, which essentially we're a weekly show. Speaker 1 03:34 So five years, about 250 episodes, I feel like early on our voices, especially I'll speak for myself like my voice. I just hadn't found it yet. And I was nervous on the mic and I was a blogger and a writer. And so I would almost write out word for word the entire podcast, which makes it sound really stilted and like a reading. And, but at a certain point 30, 40 50 episodes in kind of found, found our voice. So by two 50, I almost feel like we were a bit complacent and we weren't, we weren't experimenting anymore. And we weren't trying new things. And, and I look back on that time five years ago now in our defense, like we're both in the midst of growing startups. I had a, an email service provider that I was in the midst of growing and selling. And it was a very stressful time in my life. Speaker 1 04:23 And so I didn't have that much time, that much good glucose to dedicate to experimenting, but then about a year ago, um, my cohost stepped back from the podcast. So I now call him cohost emeritus and he comes on the show every couple months, but that was a big catalyst almost didn't. I mean, at the time it was, I was quite scared actually, um, that I wouldn't be able to kind of keep it going and keep it interesting. Uh, you know, cause you have a formula that you record for 448 episodes and then four 49, you get on the mic and you have no cohost. And so that spurred me to get to really dig in and I started investing more time into experiments and new show formats and all that. So if anything, I would say that was a spark, you know, it lit a fire under me to try all types of formats, like round tables and hot seats. Speaker 1 05:10 And, you know, we don't, we've always enlisted her questions and some teaching, but I think I have like seven or eight different show formats that I rotate through. Now I want to get into, to kind of the recent change in the podcast and the experiments that you've been running in the different formats and things like that in a minute. But I think a lot of people ask this question as they're getting started of like, am I going to have to talk about this topic for 10 years? And how am I going to do that? And, and I, I project a lot on the show. I talk about my, my fears and my concerns. Cause I think I'm kind of a, a bit representative of a lot of our listeners to say, like, you know, for the show, how, how am I going to talk about podcasting every week for years? Speaker 1 05:50 I mean, there's in a sense only so much you can talk about. And I think the key is finding ways to peel onion and finding new angles to talk about. But I mean in 500 episodes, did you and you and Mike get on the sh on the mic sometimes and say like, what are we going to talk about this week? Like, how do you find new ideas of new angles when you're talking on the same general topic every week? The answer is yes, there were, there were weeks when we would show up and really just skin of our teeth get an episode done in terms of not knowing what to talk about and neither of us having the energy to do it. Um, and, but we always had backup plans where it's like, well, I'm literally going to head over to hacker news or growth Speaker 1 06:35 And I'm gonna look for an article that we can read and talk through on the show. So that was like our plan. See, I don't, I don't love those episodes. I don't think they turn out. They're not our best format, but it's was better than skipping a week if that makes sense. Um, so that was that's one thing is we, we did, when there were two of us, we did trade off outline. So every other week I had to put some thought into it, but every other week it was taken care of. I literally just showed up, talked for 35 minutes and walked away, you know, so that made it easier. Um, but I think, I think the other thing is exactly what you said. It's peeling the onion and it's learning to think about the topic from a lot of different angles. Um, and not just like I recall the first 20, 30 episodes we had all this, I was pulling content from my book and all this teaching that I had done. Speaker 1 07:23 And then we kind of ran out of things to say, and we actually switched for, we started going every other week. Cause it's like, we just don't have anything new to talk about, but then we did figure out, Oh, listeners are sending in questions. What if we do a Q and a episode every month? And that became a recurring thing, you know, that we still do to today. And then historically we have not done very many interviews, but that's of course another way to mix it up, you know, to get another voice on and another, another perspective. Hmm. Hmm. Do, do you attribute the, the frequency and the regularity of publishing, uh, to, to be kind of one of the biggest drivers of your shows like listener growth? Yeah, I do. In fact, we shop every week. Yeah. Yep. I think we saw that, um, when we were, we were weekly for the first several months and then when we stepped back to, to every other week, the growth just stagnated. Speaker 1 08:17 And that was the only time we've experimented with that. I've thought from time to time about going twice a week, but that would, that would be a whole other, that would become a part time job at that point. Um, but yeah, I think that frequency and consistency are, are such that such a big piece of it. I mean, there are ways I've heard of people like trying to hack podcast growth, but I just haven't heard at work. Anything, anything that works besides showing up or, you know, potentially like you've talked about, um, it, I mean, it's building an audience, building social media, following getting people to share, getting some reviews. It's all the stuff that we all try to do. And then, you know, you've talked about buying ads in podcatchers, which I think is interesting. But beyond that, yeah. I think it's either being early to a space or having a really unique voice, um, you know, like, uh, like, uh, uh, Joe Rogan, right. Speaker 1 09:01 Where he's just so different and he, and he was relatively early. I mean, he was not early to podcasting per se, but to this whole interview format as this wave of podcasting has really built over the past, you know, I mean, it's been building for 10, 12 years, but I mean, it's really accelerated, I feel like over the past two or three years. Um, so yeah, I definitely, I think inconsistency is absolutely a huge negative impact on growth. Yeah. And just to, to kind of drill down on that for folks who kind of, haven't heard me preach about this previously is it is what for me, what consistency does, is it, it relays a degree of kind of confidence and dedication from your perspective to the podcasts that your listeners see or your prospective listeners, see if your listeners say, man, Craig just doesn't show up every once in a while. Speaker 1 09:48 And so they only get two or three episodes in a month and then they miss three weeks and, and all this, I'm not going to invest my precious podcasting time in a show that isn't giving a hoot enough to show up and publish an episode every week. Whereas, conversely, I think they see the opposite when a show like startups for the rest of us who say, man, Rob, or Rob and Mike show up every week, I'm going to kind of give them the courtesy of, you know, listening to the show because they're putting so much into it. Um, I think it's definitely this two way trust and dedication street that that listeners see really, really clearly if it's not there. Yeah. It's a really, you build a relationship. Yeah. Right. And I think that relationship has to go, it has to go both ways. I'm kind of talking about the, the, the pivot in the show and the change of format after your cohost, uh, took a step back after 440 ups, 48 episodes. Speaker 1 10:43 Um, that had to be pretty scary for you. Cause I know this is a big part of your identity. I mean, professionally and kind of socially, probably, um, your podcast is a big part of, of kind of who you are and what you do was what was the emotion like as, as that kind of unfolded, it was a mixed bag in terms of, I was scared. I was like, I was frightened that I wouldn't be able to maintain the level of just the content quality. I felt bad for my cohost who was basically taking a step back and I knew that was a hard choice for him. Um, so there was a bit of sadness. I mean, I think there was mourning from both of us to, you know, again, you get on the mic and recorded every week for nine years to suddenly realize why next week I'm going to record without him was it's, it's a bit of a loss, you know? Speaker 1 11:27 Um, at the same time, like on the positive side, I was also highly motivated to do it. Like I find, you know, as an athlete in high school and in college and I was motivated by competition and I was motivated to achieve and to win and to, you know, as a, uh, a hurdler, right. I was a track runner and I feel like that sense of competition like came out in me when this, when this moment happened, where I didn't say, Oh my gosh, curl up in a ball. I can't do it. I thought I can beat this. You know, I can, I can do, I can not only make it as good, but I think I can make it better. And it stoked that flame in me, you know, to do that. And I think that was probably a bit of a coping mechanism because, you know, you heard that there were negative emotions and then how do I, how do I turn this into something that's not so hard? Speaker 1 12:17 Yeah. Yeah. From a, from a strategic standpoint, there must have been a lot that went into yup. You having to be responsible for the show every week and you having to organize with the editor and you having to outline the content and arrange the guests and, and all this kind of stuff. Can you share a bit about the things that, that you did as you kind of absorbed all of the work of the show, uh, you know, from a, from a, like a day to day and kind of boots on the ground perspective? Yeah, sure. I mean, so we did a good job. We've always had an editor. That's basically, we just put the files on Dropbox and the show is published X days later, you know, it's every Tuesday morning. And so that really didn't change. What changed was the hardest part was coming up with the ideas for shows every week and to not be satisfied with the old format, which a lot of times was my cohost and I getting on the mic and running through our thoughts on like tactics and teaching. Speaker 1 13:19 And I just, I don't think that works with one voice. And I think it's just a lot harder, you know, you can do them every once in a while. I do a, you know, a solo show every three months or something, but I think trying to maintain that 52 weeks a year, and it could be a real challenge and take a unique individual. Who's not me. So yeah. What, what did Linda my plate was just like, okay, what do I do next week? That's not the same as last week. I do not want this to be an interview show down there already, too many of those. How can I sprinkle, you know, get creative with this. And as you know, like creativity is the hard part, right? It's how do I do something novel, but not every other show is doing. So what I ultimately ended up doing was hiring an assistant producer who helps with she got the podcast production, the whole process, and now in notion, and it's an, a calendar. Speaker 1 14:06 And then there's, you know, that Trello like the card view of it. And so she has taken over even I'm still coming up with the content, but all the nuts and bolts are literally now just handled, including the social media, you know, creating audio grams. I mean, just all that stuff is handled by someone else. So I, I mean, I guess to answer your question, it's like in the near term, once I was solo, the biggest thing was like scheduling guests and coming up with content ideas for the next week. That was probably the biggest burden that fell on me. A question that we get a lot is around mixing up the content styles and having different formats of shows. And I always tell people, because in this show and in my kind of personal podcasts, we mix up the format a fair bit between, you know, like you're saying two, three, maybe four different types of formats. Speaker 1 14:54 We don't do six or seven like you do, but I always say, go for it, let your guests, let your audience know, you know, Hey, we're going to be trying this different format. Please let us know what you think. We'd love your feedback because we're, you know, kind of doing all of this for you. If you love it, we'll do more. If you don't like it, we'll do less. Is that kind of how you approached bringing a new format to, to the show and was that scary? It wasn't scary because I, you know, as a, as a startup founder, I view a lot of things as experiments that are easy to undo. And so I didn't have fear. It's like if I put a show out that nobody likes, so I have 498 other episodes, you know, it's one, it's a blip, it's one it's one week. Speaker 1 15:37 Um, but I absolutely, like you said, I, I would throw out the show type and say, Hey, this week I'm gonna mix it up. You know, I'm trying something new. Please do, let me know what you think, positive or constructive. And I started, I did start getting emails and tweets and such saying, Hey, I like that. Or this one was boring or whatever. And that helped me shape. And, and you know, I'm an engineer. So like at first I was like, I'm going to do a Q and a episode, every four episodes. And I'm going to do a Rob individual one every 90 days. I mean, I literally like had this whole schedule. And then I was at an event. This was pre COVID, obviously, but I was at an event and there was a group of like eight or 10 people who listened to the show and we were all talking. Speaker 1 16:13 And one of them said, I was like, what do you, what do you think of riding? He's like, I love the variety. He said, but I don't care. I don't need it to be on a schedule. He's like, you call out that, like you do this every so many months. Like, I don't care about that. I love that just on Tuesday morning when I pick it up, I don't know what to expect. That's the best part for me is that there's this variety. And there's almost this surprise of like, what's Rob, what's he going to do this week? You know? And so that, that was helpful for me to hear that, although in my head and on a calendar, I can try to try to engineer it to be at these intervals. I don't think people really care that much. Did you get a lot of negative or constructive feedback about different types of episodes? Speaker 1 16:52 Formats? Not really. I've gotten some negative about like one of the formats, and then I've gotten a really like ambivalence or just no reaction to this one that I was calling like a founder hot seat or a founder deep dive where I bring someone on and try to troubleshoot something with them. And I did let maybe three of them and got no positive or negative feedback. But when I asked again, some folks I know who listened that I saw in person, they were just like, yeah, I don't remember those episodes. I don't remember. I'd have told them, no, it was this guy. And we troubleshoot. Exactly. And they're like, yeah, I have no memory of that. And it's like, okay, then. So I really haven't done any since that conversation actually. And maybe, you know, I'm not saying that the format is bad. Maybe I'm just not, not as good at it yet, or, you know, there's ways to tweak it. Speaker 1 17:36 But, um, surprisingly very little negative feedback. One of the things that, that I think about a lot and have conversations with new podcasters about is, you know, how am I going to know, like, if this is working, how am I going to know if my podcast is quote successful? And I think the answer to that is probably different for everybody. Um, but, but for you guys with, you know, 500 episodes, obviously you've determined that this is kind of worth your time and worth the investment financial and, and kind of personal and time investment that you're putting into it. But, but what did that process kind of look like to say like, okay, this is important. I need to keep doing this. Especially when a lot of stuff got mixed up with your, with your cohost kind of taking a step back. Yeah. So, so you asking like how I've evaluated, whether to keep doing it or what makes it work? Speaker 1 18:28 Yeah, I think both, like when did you realize that it was an important part of what you do as a content creator and then, and then kind of, how have you ensured that that's still the case more recently? Um, yeah, that's, that's super interesting question. I'm not sure I've ever thought about that. I think that I would ha I don't know if we had these conversations when we first started, but I would have to imagine in my head, I was thinking, let's try this for six months and see what happens like that that's tends to be my mentality. It was a decade ago. So I don't remember thinking that, but that if I were to start something today, that's what I would think. And it would be six months. It's not going to be two or three months and you're going to get a bunch of traction. Speaker 1 19:05 You know, now I happened to have, I had worked for five years prior to that, uh, blogging and building an audience there. And I had a smattering of an email list. So when we launched, we didn't launch to crickets. Um, we were also really early, potentially the first, you know, podcast out there that was talking about this kind of stuff, like bootstrapping software. So there was a bit of an advantage, but also there were so few podcasts listeners out there. And my memory was that we, after six or nine months, somewhere in there, we had like 600 listeners, 700 listeners. And that felt like a win at the time. Of course, now that would, that would not be for me that wouldn't, that wouldn't be success, right. Because now I'm further along and just have a larger audience. But, um, I remember thinking we can keep doing this, especially once we hired out the editing and it literally became, you know, outline a show every, uh, every other week show up every other week for 35 minutes and talk. Speaker 1 20:01 And I think that it became fun. I think that's the thing is don't look at this as work. It's rare that I think I need to record the podcast. It's pre it happens, but it's pretty rare. And I think that helps right. That it, I was listening to so many podcasts. I'm a fan of so many podcasts, still that being able to create something is, you know, is still fun. But to your other question of like how, you know, over the past year, uh, you know, especially as my co steps back, why would I keep doing the podcast? You know, why not just shut it down? I think it's maybe the, you know, the question you're thinking about, and I guess since I do enjoy it so much, and since it is a part, as, as you said earlier, it's a part of my identity, you know, and it ties in with a conference and, and just my whole kind of personal online presence that maybe I should have asked myself that question more, you know, with more seriousness, but I can't honestly say that I considered shutting it down. Speaker 1 20:57 It just seems I would miss it is the bottom line. I would miss the moment that I stopped, I would regret and I would miss doing it. Yeah. I feel the same way. I mean, I think it's a, it's a great way for me to kind of express myself. It's about the only really creative thing I do. And cause I don't blog that much. We do YouTube a fair bit, which is cool. And I like it, but it's a lot more kind of strictly about business, but even this show, I just feel, yeah, I feel more creative doing this show than I do doing YouTube video, which is about the only other kind of media that I produce on a regular basis. And I think it's just the medium, I think video is, is just so hard. And so in a way like black and white, like everything is really set, but on this, we can record this for 45 minutes and we can cut out a 10 minute section and it's fine. Speaker 1 21:44 And nobody, nobody knows. I think that that kind of graces from a medium perspective, like one of the really cool things about podcasting that you can go try a bunch of stuff and a bunch of it won't work and that's okay. I just, I feel different about the, yeah. The style, like the format than anything else. Yeah. I think video is taxing and video makes me tired. I've recorded quite a few videos and I leave feeling more tired than when I started. Whereas podcasting, sometimes I'm more tired, but a lot of times I'm energized and a lot of times I'm energized to hear, I can't wait how this actually comes out. You know, I can't wait to hear how that sounds. Especially one where I feel like we just hit it on all strides, you know, all the cylinders were firing and I actually literally get excited. Speaker 1 22:27 It's kind of, maybe it's a weird trait, but I get excited to listen to my own show the next week because I'm like, Oh man, this guest was so cool. Or that round table, I felt like, you know, really just resonated. And I like to hear if that's true or not, sometimes I'm wrong, you know, sometimes it's not as good. And then I learned to improve and other times, um, it's just, you know, you can be proud of what you make, I think. Yeah. Proud of your art, you know? Yeah. So, so, you know, 500 episodes in, um, for folks out there that are just getting started now, what kind of looking back at what you've learned and seeing the podcasting landscape from the lens that you see it both from being involved in a lot of tech companies and in the space, um, and as a podcast of yourself, like what, what do you think about getting started with a new show now? Speaker 1 23:13 And what advice might you give someone? Yeah, I mean, you know, it's always five years ago was always the best time to start a startup or start a podcast because there was less competition and, and on and on and on, and, you know, four years ago was the second best time in three years, but it's like, you didn't, if you didn't do it, there's still, I believe amazing opportunities to start startups and to start podcasts. And there's actually a lot of overlap between the two, um, or a lot of similarities, I think. So when I hear people say, Oh, I tunes is too crowded or there's XD zillion podcasts out there. I always think, but there's there's room for innovation, there's room for novelty. And there's a room for a unique voice, a unique voice to enter almost any space. So I mean, my advice is if you want to do it, I I've started to more podcasts now. Speaker 1 23:58 So I have three of them, you know, and they're not all weekly. And, um, but I did it because I feel like I felt like there was a gap in, in our space, can, you know, kind of the, the bootstrapper self-funded, um, startup space to have a really high quality production, like a, this American life or a Gimlet startup type feel. And I wanted to do that. And so, yeah, I guess the proof is in the pudding, right? If, if you ask me, should you start a new podcast? It's like, well, I've just started to move more in the past year. So yeah, I think there's, there's always room, but think of it as how can I innovate and be novel. And maybe you do start by, I was going to say copying, but weren't paying homage, paying OMA hanging in Omaha to, to a podcast you'd like, or a voice, you know, or a, an interviewer or a whatever that you like, but it's developing your own style. Speaker 1 24:47 I think that's going to get you, um, in the, in the earbuds of more people, rather than just doing the same thing everyone else is doing, it's really hard right now to stand out. And, but I think as you're saying, that's where people are being really successful. Uh, you hear of some of these weird formats or things that people are talking about or angles that people are taking on a topic and they're the ones that are being successful. And the people that are not coming with an audience already into podcasting or having a hard time getting traction, I would say maybe that's the one other places. If you already are a blogger or a YouTuber or have an email list or something, you should start a podcast because people want to connect with you in a different way. And that's cool, but starting from scratch into podcasting, doing the same thing as everybody else talking about the same thing in the same way at the same frequency is, is just a super uphill battle. Speaker 1 25:38 Yeah. Yeah. And I would, I mean the way I totally agree that if you already have an audience, this is a great way to extend it. If I were going to start a podcast today, personally, I would probably cut my teeth on a hobby podcast that is aimed at, at a super tight niche, like a TV show that doesn't already have. You know, I wouldn't do game of Thrones, right? Not just cause the show is over, but because there were already a bazillion of them, but like what show is like a B tier show that maybe no other podcasts exist for it or one other podcast exists. And you can watch that show as it comes out and talk about it and cut your teeth and learn how to edit and learn how to publish and people who like that show will rally around it. Speaker 1 26:14 Right? Cause you can go to the forums and the Facebook groups and if they search for it in iTunes, when they accidentally looked, think they're searching for the show itself and they're in the podcast tab, they'll find your feed now, are you going to make a living out of that? Probably not, but that's, to me a great way to get experience and to start understanding what it is to do a podcast in a way that I do think you could get. I think you could get hundreds of listeners pretty, pretty quickly, um, doing that. Versus if you start up a business podcast today with no audience, I don't know how you would stand out, you would need to do some pretty outrageous, you know, stuff to try to break through that noise. One of the things I wanted to ask you about, cause we've known each other a long time now, and I don't know that I've ever kind of heard the story from start to finish, but you have created a, uh, an event and a successful business from your podcast. Speaker 1 27:05 MicroComp is a multi-time yearly. Oh, the bill coronavirus, uh, in person event that, uh, as I understand, it kind of came from the podcast. Can you kind of talk about that kind of journey and, and what kind of lessons do you think are applicable to other folks that might want to kind of bridge that gap between like having a podcast and then doing something with it from a, an event or a business or a following kind of perspective. So I feel like you guys have done that really well. Thank you. Yeah. Yeah. I really do think that MicroComp would not exist as it does today and would not have been as nearly, nearly as successful without the podcast. I questioned if we would've kept doing it, it would have been, I think we could have thrown an event. I just don't know if it would have been that great. Speaker 1 27:49 And I don't know if it would have made enough money to make it worthwhile and it doesn't certainly doesn't make buckets of money, but we always had to justify our time, you know, when you spend hundreds of hours producing an event and it breaks even, that's probably not something I'm gonna, you know, I'm going to be doing. Yeah. It, it really spring out of, I mean, I think the steps in my head are once you build an audience, whether it's podcast or blog or video blog or whatever, then what we did w it was kind of at the same time, but like, we then built a community. So it wasn't just disparate people listening who didn't know each other today. It would probably be, you know, you probably do a Facebook group or a Slack group back then. It was an online community. It was like forums plus, um, teaching educational material around bootstrapping startups. Speaker 1 28:33 There was really quite, literally almost nothing on the internet about how to do that. And so we created all these, like this curriculum, but then there were forums and people started meeting each other on the forums and getting to know each other. And that was the next step that I think made the event an easier sell, so to speak because we did have people that were already paying us for something. They knew us, they liked us, they trusted that we would deliver on something. And so when we did go to sell tickets to this, uh, event, back in 2011, it was still really hard. I think we only wanted like 180 or 200 people. We wound up selling about 70 tickets. And then we wound up giving away a bunch of tickets or like charging like 200, like at cost just to fill a room. Speaker 1 29:12 So we had about 105 people total, including speakers. So it wasn't nearly the turnout that, that we wanted, but I don't think it would have been nearly that without not just the podcast, but also that fact that we had started connecting people. And I think that's something that people often overlook is there's more value in you connecting your audience to one another, just like you've seen Craig at, at Microcom, there's more value in that, in the interconnections and that kind of the network, the hallway track, we call it. Then I think just hearing me talk on a microphone every week, you know, are being broadcast to and not knowing one another. And so that's to answer your question, like that's where the value comes, I think. And so if you want to start a business or start charging for something, yes, of course you can sell courses and you can sell eBooks. Speaker 1 29:58 And that's a great way to do it too. And I've done that. But I think the longterm value that we built is this is the Microsoft community. That's the thing that has existed and has been timeless and has been evergreen. And to me is more of my legacy and more of my value that I brought to the world. And perhaps anything else I've done, that's really interesting. Yeah. I, I love the community aspect of, of content podcasting or blogging or whatever it is a core of courses and events. And I think this next step of community is not a bunch of people coming to our Facebook group and, and talking and me, me talking with them, but them talking and getting to know each other, uh, is that, that second level. Um, and when that community then goes and does something on their own, you know, like starts a thread in your group on their own, without you prompting them to do it, or, you know, your community starting their own community may be, uh, you know, talking about like these TV shows that start podcasts and communities around them and stuff like that. Speaker 1 30:58 We had a guest on the show previously, Jack reciter who his community and his fans started their own discourse channel, I think on they're all on their own. And that's like, the ultimate for me is if you can get a, a community that is that engaged with what you're talking about, and you've found that degree of fit with people wanting to discuss more about your topic, that they are able and willing to go online and spend their time to, to invest their time and resources into kind of furthering that community without you poking and prodding and encouraging those things along. I think that that like kind of critical mass is, is where it really gets interesting. Yeah. Yeah. I would agree with that. And in the early days of our online community, it was me answering all the questions on the forums. And I was, you know, I was the senior at the table, so to speak or just the, the mentor to, to all the people in there. Speaker 1 31:55 And that changed within, you know, a year or two, which was great. And now when I go into Microsoft connect, which is our online, it's a, it's a Slack channel for startup founders. I will go into a thread that's been up for an hour or two, and a question about pricing, blah, blah, blah. And I'm like, Oh, I have thoughts on this. And I go in, and there's 10 responses from a bunch of people, great answers. And I'm just like, my work here is done. I don't need to do anything. I don't even need to weigh in because these answers are great. And that's, that's, it's exactly what you're saying. Hmm. Hmm. Interesting. Um, kind of last question I wanted to ask is, is looking back 500 episodes. What is the one thing you wish you would have done differently? It's hard to, it's hard to think of only one, but I think, I think I, I do have a regret around the podcast and it's that there were times when we were busy with other things, with life, with running companies, with whatever, and we got complacent, like I said earlier, and our growth stagnated, like I think the show could have, you know, twice as many listeners today, if we, I, or we had been more creative and more dedicated along the way now we were dedicated enough to put a show out every week, but was it our best material? Speaker 1 33:05 You know? And, and was it, was it where we giving it our all and the answer is no, there were entire six month, one year threads where we were, we were kind of phone phoning it in is too strong, right. Because we still, we showed up for 45 minutes every week and that's, that's something to be sad. But I think if there's one thing is I would have continued to innovate and not kind of rested on our laurels of, um, you know, just the organic growth that was coming through. I would have liked to be more serious about it, I think. And that's hard, it's hard to stay energized to, to innovate and always challenge yourself when the podcast is not your main thing. You know, whether it's for your business or your hobby or your church group or whatever. I do think it is tough to not just say, okay, I have, I quote, have a podcast now. Speaker 1 33:55 And it is, it has so many listeners and it is growing. Um, I'm just going to keep doing this thing. I don't think that's wrong. I understand that. Like now looking back, you say, man, if we wouldn't have kind of taken those months or years as a breather, the show might be a little different, but, but I don't think that's wrong. I think that's really understandable. Um, when it's not your main thing, no, it's always hard to it's hindsight, you know? Yeah. Yeah. Cool. Um, awesome, Rob, thanks so much for sharing everything about the podcast that you did here. This is really cool insights for me. And I think for everyone listening, um, for folks that want to kind of check out more about you and kind of what you're up to in the podcast, where is the best place to start ups for the rest of or any podcatcher district, you search for startups. And we're typically in like the top three or four. Awesome. Thanks Rob. For coming on the show today. I really appreciate it. This was a lot of fun. My pleasure.

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