RS283: Team Retreat, Personal Branding, and The Long-Term View

July 20, 2023 00:21:11
RS283: Team Retreat, Personal Branding, and The Long-Term View
Rogue Startups
RS283: Team Retreat, Personal Branding, and The Long-Term View

Jul 20 2023 | 00:21:11

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Show Notes

In this solo episode, Craig reflects back on his journey as Castos turns six years old. He also looks into the possibilities and the future of podcasting and entrepreneurship. What do the next two years look like for Castos? What’s it look like when your business is in its awkward teen years? How do you ... Read more
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Episode Transcript

Speaker 1 00:00:08 Welcome to the Rogue Startups Podcast, where two startup founders are sharing lessons learned and pitfalls to avoid in their online businesses. And now here's Dave and Craig. Speaker 2 00:00:19 Hello. Welcome back to another episode of Rogue Startups. This is episode 2 83. Uh, I'm your host, Craig Hewitt. Thanks so much for tuning in, and I apologize that it's been so long since we've been on the mic. Last episode with Joel Kke was out in early June, so it's been kind of just over a month since we recorded an episode. Yeah, just a lot going on, right? Uh, Dave and I have both been busy. We had our annual team retreat for Casto. We went to Athens, Greece around WordCamp Europe. Amazing experience. Really super fun. Uh, amazing to be with the team. Did a lot of cool activities and played for a while. Uh, did some awesome work and planned the next, you know, the rest of this year and into, into 2024. Can't believe I'm saying that already, <laugh>, but I mean, I'll just say if you are a remote team and you're more than a couple of people, if you haven't done a, a remote team retreat, it, it's amazing. Speaker 2 00:01:14 Um, I wrote a blog post all about kind of what we did, how I think about it on, on my blog. So Craig hutt.me. Um, so if you wanna go check that out, it, it's really an amazing experience. Great to get to know your team members on a really deep level, um, to where when you're, you know, on Zoom or in Slack and somebody says something, you're like, oh, that's, that doesn't seem right. That's weird. That's off-putting, you know, whatever. You have the, you have the context, you have the, the background and the history and the perspective. Uh, it's really understand what somebody really means behind kind of a maybe one line comment that they say. So it's just great, right? We leave the retreat, uh, knowing each other better, really focused on what's going on with work, and have very clear guidelines and, uh, and perspective on, on where we're going again for the rest of this half the year and into next year. Speaker 2 00:02:07 So we do annual team retreats every year. They've been in the summer. Um, the pandemic of course interrupted them, but, um, we did last year in Chicago this year in Athens. And I don't know where next one will be <laugh>, but, um, but they're great. We, we typically do two or three days and, and it's about half work and half fun with, with a lot of work kind of interspersed at dinner and walking around and things like that. So yeah, that's been, that's been the real big highlight for me, um, kind of at the beginning of June that, you know, and then it's just summer and the kids are out of school. And we took a, a few weeks to go to Florida to visit some family saw SpaceX launch, which is pretty amazing. But, but all along there, you know, had a lot of time that was kind of async, you know, with, with traveling and visiting family, working mornings and evenings and had a lot of time to think about, you know, kinda where we're going along, you know, all of this. Speaker 2 00:02:59 Uh, Casto turned six years old and, um, that's a long time for me at least. That's a long time to be doing anything. Um, podcast motor for kind of two-ish years before that. So eight years in, in online business. And, um, you know, I've been talking with a few founders about this concept of kind of entering the teenage years of a business and, um, and it's not, it's not nothing. I don't know that there's anything actionable or any kinda, uh, momentous occasion that needs to occur, uh, around the time you get to this age. But I think the big shift for me was, um, you know, podcasting was always really popular. Still is. So that's great. Um, a lot of m and a activity with Spotify and Amazon buying a bunch of, uh, you know, podcasting companies. Um, that definitely seems to have settled down a lot. Speaker 2 00:03:49 Everyone is going through the, the, the dynamic of, you know, money being more expensive. So venture capital and m and a, uh, kind of having less velocity, I'll say. And, and so pair that and the kind of current economic environment with the fact that we've just been at this a while, <laugh>, um, it is kind of making me take a, uh, is making me take a more measured approach to how I view our growth, our kinda how we approach business, the personal sacrifices. I'm willing to make both, both time and money to, to really just dive hardcore into the business. You know, I always said like, we're gonna run headfirst into this wall <laugh>, and, you know, one of two things are gonna happen. We're gonna be huge success and sell the business, or, uh, or we're not, and we didn't sell the business. I think we're still very successful. Speaker 2 00:04:42 We're a seven figure profitable SaaS business. Uh, and by a lot of measures, I think that's very successful. Um, we haven't grown as fast as we want, I think no one ever does. Um, and, and so, you know, this, this time, you know, I say to, to our advisors and investors, you know, kind of starting the middle of last year, I view the next two or three years. So we have another year or two of that as, as kind of just like empty time for like a potential exit from the business. You know, if, if m and a is, you know, relatively dried up, venture funding isn't as, uh, readily available as it used to be, um, it's a really good time for us just to be heads down executing on the things we need to do and continuing to grow a, a profitable, sustainable, successful business. Speaker 2 00:05:31 Um, and, and so that, that's been, that's been really nice actually, because for a long time it was always just like, I'm doing all these things with an eye towards this future. Um, and who knows what that future's gonna be, right? We never tried to put the business up for sale or anything. Um, but now, like, not even thinking about that, not even worried about it. Now all I'm thinking about is what do I need to do and what does the team need to do this month, this quarter, this year, to put the pieces in place to continue to grow and sustain a successful business? And I'll tell you, like, it's a super healthy mindset to get in. Um, so I don't know if this resonates with anybody else. If you've always said like, Hey, we're gonna, you know, we're gonna grow this damn thing and we're gonna make it successful, um, and we're gonna burn the ships on the way there. Speaker 2 00:06:20 Um, that, that was kind of my, my approach to it. And, and that's not super successful because you can only do that for so long. And at some point you have to take this mindset shift like I've taken now I think and say, okay, well that didn't happen. It's not that it didn't work, cuz we're still left with a, I think a successful business. We have, you know, thousands of customers. We have millions of dollars, we do a year. And the change is just that we are self-sustaining. Uh, we're still growing. We are an amazing team. Uh, I'm personally very happy at work now and the, the trajectory and the path of the business is we'll probably just keep doing this for a few more years as opposed to, you know, one year or two years or something like that. It might be two or five more years, which you start making really different decisions. Speaker 2 00:07:09 <laugh> at that point when you say, Hey, my time horizon, it's not 12 months, but it's five years, right? Like, think about like the product decisions you're making. Um, if you're anything like me, it's like, ooh, what can we do this quarter to make, uh, an impression or make a change in the business? If you're looking at a time horizon of like five years, you start saying, Ooh, okay, well we can take, and you can take this quarter to do a thing that's maybe gonna make no impact on the business, but is gonna set us up to be able to do something else that's gonna have the opportunity to make an enormous impact, you know, in 18 or 24 months. Um, that seems really healthy to me, <laugh>. And, and that's just where I am with, with everything, with product, with marketing, with sales, uh, with team. Speaker 2 00:07:52 And, um, and I think just kind of pairing that with being profitable and default alive, which for the first time in a very long time we are, um, is, is pretty cool. So yeah, just, uh, I'll say like an evolution of mindset for me in the last few months. Um, you know, turning profitable, continuing to grow in a difficult economic climate and, and kind of fully gring the fact that, um, like I don't wanna sell right now. We're not to the point where I would get what I want outta the business. We're still growing, not growing as fast as I want. We never are <laugh>. And, and so just kind of saying, I'm gonna put the blinders on for the next 18 months at least, and we're gonna do some amazing things and I'm just not worried about what that outcome is and a couple of years because it's a couple years away and I don't need to worry about it. Speaker 2 00:08:43 I need to worry about today and tomorrow. I need to get back on this podcast and talk about what I'm doing. Because I mean, 283 episodes now, like this is, this is by far like the single largest body of work that I'll ever do online, right? I've been doing it for six years or seven years, gosh, seven or eight years <laugh>. And, and, and a lot of how I think has evolved on this podcast and a lot of kind of who I am as a, as a business person and a, you know, quote personality or whatever is is here on this podcast. So yeah, it's, uh, it's great to be back on the podcast. I, um, I just missed being here and so wanted to share a little bit of an update for me, um, on the retreat, on, on kind of just how I'm viewing like the long-term trajectory of Casto. Speaker 2 00:09:33 Like, and, and I hope the, the summary there is all super positive, taking a much longer term approach, um, and, and have a ton of hope for both podcasting kind of content and content marketing in general, even in the AI era. I know a lot of you'll be scoffing at that. I still think content is gonna be hugely important. And, and, and you know, one thing that came out of the retreat for us is, you know, several people said it to me and I agree, is we have the right people and the right seats at, at the company. And that's amazing. And that's, that's pretty rare, right? It's not often that you are able to say with a straight face like, man, everyone in this company is doing the job they should be doing and, and it's awesome. Yeah. So, so feel really fortunate that that's the case. Speaker 2 00:10:22 Um, it's not an accident, right? We've been working very hard and very intentionally to get here, but, um, but yeah, feel really good about kind of where the company is at today, um, and, and where it's going. So that all is, is really great. Uh, I'll share, and I'll be talking a lot about this in the future, so if this is not for you, I apologize, but, but I'd like to hear, so shoot me a message, uh, shoot me a message on Twitter, I guess. So I'm the Craig Hewitt on Twitter, but you know, one of the, one of the places I am focused on these days is, is something I haven't done much of at all aside from this podcast and my other podcast with Andy Baldacci called Seeking Scale. So Andy and I did seeking Scale for about a year and a half, kind of mostly during the pandemic. Speaker 2 00:11:08 And then that came to like a natural, um, a natural ending where we kind of had talked about what we wanna talk about and, and get to like this, this point where we just kind of don't wanna <laugh> don't want to dwell on the, those aspects of business anymore. But, but podcasting has been how I have created and tried to grow my personal brand. Um, so I think personal brand is something that you hear a lot about these days. Um, and, and, and I think, you know, there's definitely a lot of kind of blowhards out there <laugh> that are talking about personal brand for all the wrong reasons and they're just trying to make money teaching you how to grow a personal brand. And, and like, whether that's right or wrong, I don't know, like, I think there's probably, there's probably some value in that because if you can do it effectively, um, the, like, the saying I like to say is it's, it's like playing the game on easy mode versus hard mode. Speaker 2 00:11:58 You know, think about if, if you're a founder and you are trying to launch a product or grow a consultancy or do whatever, and you, you don't know anyone, you don't have an email list, you don't have a following on social, you don't have a podcast with 283 episodes, you don't have any of that stuff. Um, how, how hard is it to go from zero to one or, or from one to 10, you know, say one to 10,000 or to a hundred thousand a year or, or whatever it is. Um, it, I'll tell you, it's really fucking hard, right? And cuz I did that and this podcast was the way that I was able to, to grow a brand to, to whatever degree, and I don't, I don't care, I guess like the, the, the magnitude of that brand, but I met a lot of interesting people. Speaker 2 00:12:42 I got my very first customers, uh, for podcast Motor through this podcast. Um, I became known again to whatever degree, uh, in, in our space because of this podcast. And, and I think for a long time I discounted the value of that, or I didn't appreciate the value of that. And now, you know, I'll just be honest, like Casto has reached a, a place where we're growing less quickly than we were before. And it is because we reached this kind of equilibrium of our existing customer acquisition channels and marketing channels with like the natural churn that a SaaS business has. And our SaaS is very, very, very fortunate to have very low churn. And, but, but even then, you know, people churn, people stop podcasting, people get sick, whatever. Um, and, and so we've gone from growing, you know, at a pretty good clip to growing at a less good clip. Speaker 2 00:13:37 And so I'm sitting here thinking, okay, we need to develop another customer acquisition channel. And, and I think maybe some of the, the frustration you sensed in my, my previous segment about how I'm viewing the business and, and, and kind of my perspective on, on what we're doing and taking a longer time horizon is because we, we kind of beat our head against the wall for, for about two years with, with trying different things. And, and some of them worked and some of them didn't. Um, and at this point I'm kind of saying like, man, we, we tried a bunch of stuff and, and none of it was like this thing that unlocked exponential growth. And so I kind of go back to the drawing board and say, what do I like? What am I good at? Uh, uh, what do I want to do and where do I want to focus my time? Speaker 2 00:14:22 And, um, and I think a lot of those do point back to personal brand and me being a marketing channel for the business. And, and I think a lot of people might scoff and say, oh, you're too big of a company and you should be, you know, running all these sophisticated, you know, campaigns or funnels or something like that. And, and that, that may be true. But I think the simplest way to again, go from like, maybe not zero to one, but one to 10 in, in developing a new customer acquisition channel is for me to be a bigger voice in the kind of creator and podcasting space so that people know, like, and trust me more so, and say, Hey, when I need a podcast host, I'm gonna choose Casto. Or when I need someone to edit and produce my podcast audio and video, I'm gonna choose Casto Productions because I hear Craig talking about how great their team is, and I see all of these examples of, of how their, their product I service does great stuff for customers. Speaker 2 00:15:24 I just think that's not that big of a lift, right? It is not, it is not some complicated, difficult thing that we have to hire a bunch of consultants for. It is me doing one or two things very consistently and hopefully very good over a long period of time. And, and that will drive eyeballs and attention to our brand Casto and hopefully customers. And I'm trying to keep it as simple as that. <laugh>, I'm trying to keep it as simple as I'm gonna post content on YouTube and I'm gonna post content on LinkedIn. And as much as I think everyone listening to this podcast probably prefers Twitter for, for kind of growing their personal brand, one, it's a super unstable platform right now, I think, um, and in terms of like where it's going, it, it's not gonna die. I don't think that threads is gonna overtake Twitter or anything like that, but I just don't think it's where I want to invest my time right now. Speaker 2 00:16:20 And especially if you think about growing a productized service that's 1500 to $5,000 a month, uh, LinkedIn is a hundred percent the place where, um, where I should be focusing my time and energy because businesses are there and businesses are the only people that have the budget to spend that much money on creating, you know, audio and video content for their brand. And so that's my hypothesis is that, um, kind of me having a stronger, more impactful and um, kind of higher reach brand will positively impact the business. And I'm already seeing kind of beginning signs of that just a few weeks into it really is, you know, more stuff is happening, more leads are coming in for castes productions, more website visitors. We're starting to see, you know, social be a, a blip on the, on the radar in Google Analytics. Don't even get me started about Google Analytics for, but I think this is like a, a, a lesson maybe. Speaker 2 00:17:15 And, and we always try to take an abstract away lessons that it's not just me and Casto and what I'm seeing and learning, it's what can you all take away from this and apply to your business. And maybe it is that creating content within your name and, and on your personal brand on behalf of the business can be very impactful. I think no matter where you are in the, in the journey of your business, um, it may be, um, you're just getting started and it's really one-to-one, I'm gonna do this to get customers. It may be kind of slightly higher level or leverage, um, where, where you're building a brand that is kind of been one to many and you hope to bring in, you know, dozens or hundreds of customers. Or you may be to the point of a, uh, Andrew Wilkinson or Alex Orey or a Rob Walling where you're saying like, I'm gonna build my personal brand and extend my personal brand because I want to raise money or get deal flow or be able to hire amazing people. Speaker 2 00:18:16 Um, I think the reason that your personal brand is an asset to you and your business changes over time and changes as your business progresses and evolves so early on, just customers like one-on-one customers, the next stage may be, um, one to many customers or channel partnerships or things like that. And then after that, it's uh, you know, the real kind of visionary stuff that if you are, you know, past the point of kind of in the day-to-day operations of your business are really important to you, like hiring and funding and acquisitions where, you know, I'm not quite there yet, right? But, but having a strong personal brand certainly won't hurt <laugh> when I get there. So I view it as, as a huge and investment, um, and a very worthwhile investment. And we'll be talking about it a lot here and hopefully kind of debunking some of the bullshit myths of like the, the Twitter bros and stuff, uh, and, and really trying to give like some some very practical things that I'm learning and lessons and hopefully kind of tips and tricks for y'all to kind of implement this in four year brand to grow your business and be successful. Speaker 2 00:19:26 So, a bit of a ranty episode, but glad to talk about, uh, our retreat in Greece and why, you know, company team retreats are so amazing. Talk about kind of where, where the business is and how I'm thinking about it as we enter our teenage years. Um, and to talk about, you know, personal brand and why I think it's important even for a kinda mature, successful SaaS business, uh, and how it could be a growth lever that you maybe could pull in your business. So I hope you enjoyed, if you're enjoying this, I, I will just kind of plug also, I'm writing a newsletter on my personal site as well. So if you go to Craig hewitt.me/join, um, founder Insights is, uh, the newsletter I publish every Saturday and it's like a near real time, uh, learning experience that I've had in the business in the last week. Speaker 2 00:20:14 So every week I'd write about something that I learned recently and I hope that you find it helpful if you subscribe, I promise it won't be lame <laugh>. Um, and, and that it brings value and maybe gives you something to think about that you can implement in your business to grow and be more successful and more sane and, uh, happier on this journey. So this is the first solo episode I've done in an extremely long time, and it was really fun, but would love to hear what y'all think, you know, maybe hit me up on Twitter. Uh, I'm the Craig Hewitt, or shoot us a message [email protected] and we'll see you soon. Speaker 1 00:20:48 Thanks for listening to another episode of Rogue Startups. If you haven't already, head over to iTunes and leave a rating and review for the show. For show notes from each episode and a few extra resources to help you along your journey, head over to rogue startups.com to learn more.

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