Huge Work (and life) Updates

0:00Speaker A:Hello. Welcome back to Rogue Startups. This is the first episode in a while, months probably, and I have to apologize to you and to kind of everyone who has tuned in many of you for kind of years, following me and my co host Dave Rodenbaugh through our journey as entrepreneurs. And I think like any journey, it's changed a lot. It's certainly a lot in all of our kind of work lives and personal lives have changed a lot in the last couple of years. And I'm mostly talking about AI, like it's, it's just upending everything about how we do business and maybe even how we live our lives. I'll get into AI more in a minute and how I'm working with it and seeing it as an opportunity. But, but I just want to fill in the blanks on what the last, gosh, six months have looked like for me. So, you know, at a business level. So still running Castos, it is still going well. We, we definitely have some challenges, like a lot of product led growth, lower price point SaaS businesses around customer acquisition. The main way we acquired customers for a long time was through content marketing and SEO. And the nice way of saying it is that's really hard these days. You know, I think the reality is from just kind of my work at Castos and then serving as advisor at residence in Tiny Seed and seeing a bunch of other SaaS companies, like 250 other SaaS companies, the best business models are ones who are able to do things like cold outreach, go to conferences, work your network, LinkedIn, DMs selling a higher price point thing. And like at Castos, our average revenue per user is $29. And so that's tough. Like it's tough to make paid acquisition

1:46Speaker B:work at that point.

1:47Speaker A:It's tough to make cold email work. And so we're left with kind of few strategies. I, and I'd love for y' all to prove me wrong, like, oh, you're missing this huge opportunity. I'd love to, I'd love to be told that I'm missing a huge opportunity and that this thing is the growth unlock lever that we've been looking for. But the fact is we don't have that right now and we haven't had it for a while. And so the business has been pretty flat. And I'm not alone here. I know from talking with dozens of you all that in SaaS, a lot of things are kind of tough right now. And so that's, that's been interesting because it makes me kind of look at this and say, like, okay, now what?

2:28Speaker B:I'm 46, I just turned 46 a couple months ago.

2:31Speaker A:And Castos an amazing business. I really love it, I really love our team. But I kind of look at that and say like, this is probably not the thing I'm going to do forever. And what do we do as a company? What do I do personally? And what does kind of all this look like into the future? And the short version is I don't know. I don't know what the answer is. I think you have to look at AI and say, this is the big pivotal moment of our generation, probably. I remember when we first got aol, I was about my kid's age, so it's literally a generation ago. That was a big deal. Aol, you know, when I was in middle school, so like 93 maybe. And then real like online business and commerce and Amazon and Zappos and all that kind of stuff came a handful of years later. AI is definitely that big of a change, right? And so I think we all need to be looking at our careers. If I'll say that as entrepreneurs and say, like, if we're not participating in the AI space in some way, there is an opportunity cost to that. I won't say you're like missing the boat or you're screwed or what. The thing you're doing right now is worthless because I don't think that's the case. And I just look at CAST as like, provides for me and my family, provides for our team. And I think what I look at, and this, this thought process has taken a while. What I, what I, what I look at is not rotating out of it because I don't want to do that. Like, it's a really great business, it provides a lot of value and it's not going anywhere. Right? Like, AI is not going to replace podcast hosting. And a lot of, you know, folks would say, like, things like podcasting are more valuable now than they were before because of AI. Because the thing that we all want is genuine human connection. And so podcasting is one of the great ways to do that. I can talk, y' all can listen, we can form this connection, and I can share in a, you know, long form format. What, what's up with me? I, I think one thing is really for sure though, which is across the economy, so much of our mind share is taken up by AI. And so I think people, companies just don't have mental bandwidth to think about doing other stuff right now. I think that's one of the big problems. There's a lot going on with headwinds in my business, I think, but I think one of them is just that podcasting is not that important to people right now. Maybe I'm wrong, maybe I'm kind of negatively biased, but I don't think that's wrong. And, and I hear other people saying similar things. So I think that as we look at our businesses, we should not fight against the tailwinds that are AI or the headwinds that are AI, but take those headwinds and turn them into tailwinds. Right? How can the fact that AI is taking up so much mind share with the world? How can we turn that from a negative to a positive? And so it's things like, hey, how can we position our product as some sort of complement to AI? That's cool. I think just like slapping on a chatbot to your product probably isn't the answer anymore. Right? That's 2025, you know, style. So. So, but I think like, hey, how can we use our own first party proprietary data and AI to serve our customers better? That's cool. That's something we're looking at Castus like, hey, we have a bunch of data about our customers and their content. How can we use that to help them create better content? And so this is one of the moats I think of AI of businesses in the AI era is if you have good first party data and that first party data over time makes your tool more valuable to customers. That's huge. I am still coaching. I have a handful of founder clients who I'm coaching and it's really fulfilling. So our coaching engagement, I haven't really talked about it much on the show. Here is I work one on one with founders. We talk every other week for an hour. And really it is, hey, what's going on in your business and what do you want to talk through? What are you having challenges thinking about, Thinking deeply about? Like, what have you talked to Claude about? And don't entirely believe what it says. And I think, like, as an aside, I actually think talking to Claude about your business problems is pretty dangerous. I've done it a lot and I don't often find it to be really helpful. This is not a plug for, you know, me and coaching. I just think that maybe now with Fable, I think the models have a hard time getting the big picture, zooming down into a thing and then kind of going back up to get the big picture again. So I'm actually pretty bullish on coaching as, as a business model, maybe for myself, but. But I think that as more of us use AI more, the human element will become more and more important, and there's really just no substitute for people. I went to a dinner a couple weeks ago up in Boston with just a handful of other founders, and it was amazing. Like, just drive up, have dinner, talk about stuff. There's no one in the world who gets what we do like other founders. And that's why things like microconf are so valuable. And. And I think that the human element will continue to be more and more important over time in any kind of business that we do. And so maybe if you're looking at your business saying, like, hey, AI is. Is this big thing on the horizon that's a threat, maybe maybe look at it and say, like, hey, how can we be more quirky, be more weird, have a stronger brand, really stand out? How can we leverage in person or individuality? One of the folks that I'm coaching, their whole growth strategy right now is just getting on calls with customers, and I think that's pretty cool. I think that's pretty cool because, like, it doesn't scale on paper, it doesn't make sense, but sure enough, it's working. And they're getting a lot of data, they're getting a lot of feedback about the product and the brand and know customer support and everything. But they're also building really strong relationships with their customers, and that goes a long way. There's nothing more valuable than strong relationships with your customers. Since the last episode of this podcast, I embarked on my A hundred days of AI journey on YouTube. So I published a YouTube video every day for a hundred days, all about AI. That was amazing. I learned a lot. I did a lot of work. It cost quite a bit of money, but I went from basically 0 subscribers to 24,000 subscribers as of today, which is pretty cool. And I've been approached by some pretty huge brands like Ahrefs to do sponsored videos for them and do sponsor segments. So making a little bit of money through sponsorships on YouTube, AdSense on YouTube just isn't anything really. Like, on a really good month, I'll make a couple hundred dollars maybe, so it's not really worth it. Maybe if I can pay the editor for my AdSense revenue, that. That's cool. I'm really liking YouTube. I realized a couple of weeks ago that I've gotten myself into a trap, though, which is my YouTube channel is all about AI and I don't want to be an AI bro. I don't Want to have to record a new video every time a new model comes out, or Sam Altman is suing Elon Musk, or Apple sues OpenAI for stealing proprietary secrets. I don't want to be on the hype cycle. And so the channel is in the midst of a transformation and that's challenging because I'll go from thousands and tens of thousands of views. I have a video, I have a couple videos around a hundred thousand views, to changing the positioning of the channel to talk more about content marketing, sales and being a founder, which is really like me. That's, I guess where we're going with all this is like, you know, someone asked me the other day, like Craig, if you could do whatever you want, what would you want to do? And I said I would coach about a dozen founders. They would pay me well, I think, and every quarter we would go on a retreat together. And that's what I want to do. That's what I want to do. And so that's kind of what I'm optimizing my life for. So I want to have about a dozen founders, you know, probably SaaS agency, maybe, you know, some kind of digital service. They're doing a million, 2 million, 3 million a year. I have a coaching client that they're going to do 20 million this year. And honestly, the problems that we all have are similar at 1 million or 20 million. They're slightly different, but not orders of magnitude different. The thought process for me as a coach and how coaching works with those kind of clients is actually pretty similar. And the value I bring is having seen and done like kind of a lot of stuff and giving an objective third party perspective on it.

11:03Speaker B:So coaching, something I really like, I'm pretty good at, I have a lot of experience. But I think like being a good coach isn't about knowing the answer, it's about asking the right questions to help bring out the right answer in your client. Because my, my job as a coach is not to tell the answer or be prescriptive, it's to understand the situation, to ask the right questions, to help my clients come up with the answers and the direction of the strategy on their own. So really enjoying coaching. Want to have five or six more clients ideally, and then frankly kind of work my way up market from there. So I have some clients who are rather early on want to be working with, you know, a lot of clients in that kind of five to $50 million range because I think I still add a lot of value there. I've not been there But I've been kind of close enough to know what business looks like at that place. I couldn't coach someone who's, you know, running a publicly traded company and kind of don't want to, but really love working with founders. That's. They're my people. So if you are a founder and you're like, hey, I'm a solo founder. I don't have anybody to talk to about my kind of business challenges. Talking to Claude is weird and wrong sometimes. Reach out. You hit me up on the socials. There'll be links like in the description below to connect with me and. Or you can just go to craig hewitt.com, have some information about my coaching there and then like, what's the future of this podcast? Well, I have a couple of different formats that I think we're going to explore. The next episode after this is going to be an interview with my friend Steve McLeod, who has just written a book. So it was a really interesting discussion. We recorded an episode, honestly, like a couple weeks ago at this point. But Steve has a lot of really interesting experience around product and, and that's what his product does is kind of get feedback and help businesses understand what they should build next. And I think in the age of AI, that's even more interesting is like, hey, we can do anything. So what is the right thing to do? Super interesting. So my conversation with Steve around, like, what he's learned there is the episode coming up and then going to do a trial stunt, honestly, with a new co host. And so I'll leave that as a bit of a teaser for what is coming next. But I do think that you'll enjoy it. It's a discussion with someone who I have known for a long time, has

13:20Speaker A:been on this podcast before, and is

13:23Speaker B:a really sharp mind around everything, Business content, strategy and how those all kind of tie together to get real results from content that we're all creating. Because I think that's the big limitation these days. If I look at my own business and I think probably a lot of yours, I was chatting with another founder recently and they were like, you know, these were the easy days and we didn't even know it when we could just write words on a page and Google would pick it up and give us traffic and customers from it and, you know, SEO and content marketing. And that's hard. That's harder than ever right now, speaking from personal experience. And so I think, like, looking at

14:01Speaker A:what

14:03Speaker B:if that's hard and harder and that's not the alpha right now. The opportunity, then what is the opportunity? And I'm kind of exploring that for myself personally, and I think a lot of you probably are too. And so that's going to be kind of a running theme of a lot of my content. And this podcast is, hey, how can we do better with content that we all can create that makes a difference for our business?

14:25Speaker A:And that's kind of the meta level

14:26Speaker B:theme of the show and kind of where I'm spending a lot of my time these days. So. But we'd love to hear from you.

14:32Speaker A:What?

14:33Speaker B:Now that we're back on the mic,

14:35Speaker A:what do you want to hear more of? What do you want to hear less of?

14:37Speaker B:What questions do you have? Hit me up on socials and fire away. Like ask questions or suggest things that you want to hear here on the show. If you're on YouTube, just drop a comment in below. Would love to hear from you. And we will be back next week with another episode and my interview with Steve McLeod.