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As the CEO of Kit, Nathan Barry has a front row seat to what’s working in the most successful creator businesses.
On The Nathan Barry Show, he interviews top creators and dives into the inner workings of their businesses in his live coaching sessions.
You get unique insight into how creator businesses work and what you can do to increase results in your own business.
One of the things Nathan is passionate about is helping you create leverage.
Creator Flywheels let you create many copies of yourself so you don’t get bogged down with the little things in your business. Flywheels will help you reach a place where you can focus on revenue instead of busywork.
Tune in weekly for new episodes with ideas and tips for growing your business. You’ll hear discussions around building an audience, earning a living as a creator, and Nathan’s insights on scaling a software company to $100M.
Learn how to get more results with less effort and:
Grow faster over time.
Work less hard over time.
Make more money over time.
Marshall Goldsmith. Highest paid coach in the world. He looked at his career and he was like the people who I have spent the least time with grew the most. Okay. I think Matt Schnuck is one of the best in the world at building a team to help a creator get to a specific outcome. Sahil was here. Myself and the group encourage him to hire a chief of staff.
He actioned it immediately. His growth has continued to explode. It's just an example of incredible talent. Still needs support at just a little sprinkle and then they can fly. You know, I love coaching and Billion Dollar creator and I'm usually the one coaching someone else. We flip the script a little bit and he coaches me on my creator business.
I have the whole team at ConvertKit, which is 76 people. And then on the personal brand side, 1 and a half person team. Do you identify more as a creator or an entrepreneur? I've got Twitter, which is grown well, book that I'm working on, do a little bit of Instagram, do the podcast. And so I struggle. Should I just put all the time into the main thing, or is there a way to tie it all together?
The quick and dirty way to do this is.
Well, Matt, thanks for hosting us here in Cabo. Great to have you here, man. So we're going to do a bit of a different episode today. We're gonna dive into some of my stuff. your experience on building teams, all of that. But first we gotta give people some context. Yes. So you built and sold your first company?
Yes. Take us through the high level version of that. So that was a web 1.0 company. I moved to San Francisco in the year 2000. The first bubble was about to burst. great. Time to move to the city. Yes. I'm perfect timing for perfect time and with the company that I worked for survived. It was an early company that was pioneering, like trackable customer acquisition.
Okay, they wouldn't have called it an affiliate model, but it was it was like pioneering affiliate stuff. it's called Queen Street. They actually went public. Oh, yeah. Yeah, a bunch of the one smart decision I made there was I went to work for experienced smart founders in a CEO of at the time, like 22 year old starting companies.
I was able to, start a business when I was 25. Kind of based on what I learned there. bootstrapped that it was essentially comparison shopping software that was in the insurance industry, and sold that company to Bank rate in 2011. Worked for them for a year. Sort of life changing, you know, experience and money for me.
And then since then, I have been creating companies and usually doing like tours of duty as a CEO for like a year and a half, getting them going. I've done some acquisitions and now I have a personal holding company that, I oversee. I'm on seven boards, ranging from startups to companies in some cases that are doing 3 billion in sales.
so now at this point, you're doing a personal holding company before, like, now, it's almost a meme on Twitter. Yeah, but you you didn't plan to get into that? No way. You just that's actually like a relatively tidy way to say I'm a serial entrepreneur. And the outcome of being a serial entrepreneur is you end up starting a bunch of stuff, and then in your orbit, you have a bunch of companies that you have, in my case, anywhere between like 25 and 75% ownership of it.
Right. How many companies do you have? At least 25% ownership and. No, for now, and that's funny. That's enough. Yeah, yeah. The we've been talking here about another business you want to start. Yes. Exactly. Yeah. We say that's funny, but yeah, that's a good point. The serial entrepreneur. That's a good point. That's a good point, yes.
You keep going back to the gambling table. Yes. So another thing that you and I have in common is a deep love for really great coaching. Yes. And I think some of that you've done that's interesting is first being a student for a long time. Yeah. And really exploring a lot of different coaching methodologies. And I want to get into that a little bit.
Yeah. But then also coaching, you know if we think about coaching from a $1 billion creator perspective, yes it's a service. It's time for money. Yeah. Now you've taken a different approach. It's always stood out to me of saying like, what if I own the companies that don't operate them, but instead I hire great leaders and then I take all of my coaching talents and learnings and everything, and I just focus on coaching them.
Yes. And so instead of getting paid $2,000 a month to be an executive coach or $10 a month, you say, what if I own 75% of the company? Yes. And I get all of this upside. Talk about that some more. Yeah. So executive coaching is one path, but why not? What I did is I, I've studied almost every great executive coach that I could find who are like the top three that you.
Well I think people worth really looking at. It's worth looking at Marshall Goldsmith, who was one of the early like, pioneers in performance based executive coaching. So he'll coach like fortune 50 CEOs, CEO, Pfizer CEO, Ford. I think that luxury is an interesting one to look at. Him, I would say, is one of the more respected in the VC backed world.
So he initially coached Naval. Yeah. And Naval then introducing to Sam Altman Sam Altman then introduced to... And then I also think it's really interesting to study coaches in other disciplines, like why is Gregg Popovich a great coach? I like to pull from all of those disciplines. I've been heavily influenced by Doctor John Gottman, who could predict divorce with 91% accuracy because he identified, you know, these four patterns of conflict.
They're toxic. I went to go study with him, and I realized those are the same things that kill a company culture. Yeah, turns out people are people. Yeah. And it doesn't matter if it's a business relationship or a romantic relationship. Yeah. So I've trained myself to become, I think, coaching as a tool that then allows you to be a really effective entrepreneur or acquirer of businesses or.
Yeah, to be in a situation where, I'm either owning or advising or coaching CEOs, but I'm doing it for the upside, which feels more fun. Was that clear to you early on of like like, did you ever consider executive coaching as a business yourself? Yes, I flirted with it because there's a part of my mind that made me successful as a bootstrapped entrepreneur, which is like, how do I make cash flow early?
I have personified that person. I call him Uncle Ed because there was an uncle I had that started a family business who was just like, I had to be so scrappy. I had to I had to figure out how to make this work. And I have a little bit of that in me, and that's very effective. Like when I started my first business, it was nights and weekends until I got to 20 grand a month until I could leave my job.
That helped me do that. Uncle Ed at times were like, you're a talented executive coach. You can just charge for money that could cash flow over time. I've had to like, learn how to, you know, put that part of me in its place because otherwise I just sort of stay in small mode. That was that was the right advice for a certain season.
That's right. Yeah. That's right. So I have thought about it, but I ultimately were what I ultimately decided not to because I just have more fun. And I like the risk and the upside of aligning in deep partnership with me is something that I think you're remarkable at, that we we talk about often is finding that talent. Yeah.
And that how you develop talent, you know, both for your own companies. Yes. Then you've also found a lot of talent for. Yes, a lot of our friends. Yes. You know, you help them get a chief of staff in place. Yeah. What's kind of your process and thought process around that. So one of the companies I started, so after I sold my company, the first company, one of the next companies I got involved with was for profit but had a real impact mission.
so it was actually a company focused on hiring, in sub-Saharan Africa. Yeah, it's called Short List, and it does large scale hiring programs and now also executive search. And so I went deep on the science of hiring prime outcome. One of my biggest takeaways work samples are just the most predictive of is somebody going to work out well.
So I really look for can I look for a signal in their past or can we do something small together that shows those signals to tie back to coaching? Marshall Goldsmith. So I reviewed his career and he said something that stuck with me and kind of haunted me. He looked at his career and he was like, the people who I have spent the least time with grew the most.
Okay? And he's the highest paid coach in the world. He gets paid like six figures sometimes for a session. The people I've spent the least time with. Yes, in some cases, not all. Yeah. Grew the most. Yes. Wow. did you take away the take away from him? Was there are people who have so much potential in talent, they really just need a little sprinkle, okay?
And when they get a little bit of sprinkle in the right direction, they can fly. I look at my own portfolio, I look at my own history. There are times in which I was just as good of a coach, mentor or whatever. Yeah, and the harsh truth was, I could get a lot of my identity wrapped up in fixing the situation or the reality was that leader wasn't really able to get there.
Right. And so I would say how I've developed or seasoned is try to internalize that feedback. And I look for, can I give somebody a little bit of feedback and how well do they respond to that? Okay. you know, that could be in, a little case study, right? I get I get a case study back in an interview, and I ask for a little bit of a revision in this direction.
And if they totally get it initially, right, that's just awesome. Right? Or, I mean, we've seen it in this group at the inflection silo was here a year ago. And myself in the group encourage him to hire a chief of staff, given the fast growth of his opportunity, all the things that he's doing. Yeah, all he did is a here that once he actioned it, immediately he found a candidate.
And like his growth is continue to, explode. It's just like that. That's an example of, incredible talent. still needs support and some guidance, but just a little sprinkle. So when we dive into that chief of staff and thinking about that role, that's something that a lot of people have, you know, been coming to you for advice.
Yes. And this one that I'm considering hiring at ConvertKit. You know, it's it's a little less of a creator chief of staff because of the scale of ConvertKit as a business. But then they need to play in both of those worlds. I'm curious as you you're thinking about, you know, all the creators listening who might be at 500,000 year in revenue.
Yeah, a million, 2 million a year in revenue. At what point would you recommend that they hire a chief of staff or a head of ops? And then what should that role look like? Yeah, one of my favorite ways to help any growing creator or entrepreneur think through this is with the Zone of Genius framework from the Conscious Leadership Group, originally from, Jay Hendricks.
And the quick and dirty way to do this is take the last two weeks of your calendar, and perform what's called an energy audit. Look at what you're doing, and mark each activity as either red or green by the simple classification of did this activity give me energy or did it drain me? And if it's in the middle market, rep okay, add up your time.
The goal is 80% green, but almost nobody is there. Early. but the general thesis is, the more time you can spend in your zone of genius, the better your, you know, your business will grow, whether that's creating or otherwise. And Zone of Genius quickly is just defined as it's something that gives you energy, and it's something that you're also world class at.
So the first step is like getting clear. What is my zone of genius auditing? where am I in terms of how much time I'm actually spending there? And this is super common in any entrepreneurial growth story creator growth story growth happens. And then just like problems of success happen and then all of a sudden you're dealing with lots of stuff that you have to deal with, and you're not spending time on the things that actually you're great at and drive the business forward.
So whether it's a chief of staff, whether it's honestly any role that's going to help you, you want to basically delegate and customize the role to essentially support you to stay in that zone of genius or what's helping you grow the business best I like it. What are some things that you've seen of the way that people have have done this?
You go to directions either the like creators that have had big unlock because they found this is the result of genius, and they hired you after this, or are you go the other way of someone who, like, really struggled with that first hire because they didn't? Yeah. So especially if you're if you're whether you consider yourself a creator or you're like, I identify myself more as a CEO who has sort of come to learning about the power of creating.
One of the number one challenges is how do you stay consistent, like consistently putting out content in the way that the platform wants in order to keep growing? That's right. I've never struggled with that. Yeah. No. So that's one of the I mean, I've faced this pothole and one of the things I, I've seen running these retreats where now there's 60 or so like high level entrepreneurs who are pursuing the strategy.
Almost everyone has dealt with this at some point. And also the people who have the fastest, consistent growth curve have figured out the consistency thing. And that consistency thing is because they've invested usually in team and systems that have helped them do that. Yeah, I just recorded with Nick who's here and he's yeah, you know, he's showing this is my exact calendar for when the nine companies get rotated through every 21 day.
You know, you're like cool. There's nothing complicated about it. Correct. But I would say one out of ten successful creators have a system of that level. And being consistent as a creator, there's a whole side of it that's like just a ops challenge. Yeah. And that happens to actually be different than the creative challenge of making good content.
And sometimes there are people who are good at both of those. That's pretty rare. So but if you can hire for and this is what do you call it, a chief of staff or a creator or CEO or a head of content. When you're ready, that can just be a huge unlock of just ensuring that somebody's full time job, that you're staying consistent.
And so what are some of the missteps that people make when hiring these early roles? The problem with hiring for that role is there's there's not a lot of talent who have had the experience, right. They're going to either need to get trained up or they're going to need you. you want to ideally look for somebody who has some experience, who has grown some kind of social following that account, either their own or helping somebody else.
I mean, that's, that's, that's helpful. Or they, they at least have the raw skills or aptitude to do this. Yeah. So what are some other obstacles that you see creators face around being consistent? A huge obstacle for me. And I think, you know, I'm 46, so people who didn't grow up with social or even the idea of being a creator is actually getting comfortable sharing your ideas online on a consistent basis.
In my case, I had to go through a lot of honestly like inner psychological work to get comfortable posting ideas on a consistent basis attached to my name that then the entire world can sort of respond to and judge. Yeah, and everybody has to go through their own journey on that. But like, if you don't get comfortable with that and you don't get support to do that, that is a huge pitfall that stopped me early at certain points.
And, I mean, literally, I leaned on my coaching background in awareness of things like graduated exposure therapy and just knowing, like, I'm going to need to expose myself to this a little bit more. I created documents like the sickest Burns, like Hall of Fame, like like like the like kind of like Jimmy Kimmel's mean tweets. Okay. and like basically the shittiest things people said, they said about me to what I would write.
I would just like, document that and put it in like a Hall of Fame document. And for me, it was just like a mental trick to be like, let's just actually find this funny, right? instead of having that be the thing driving writer's block for you, you're like, I could write this. I know, but I'm immediately hearing in my head, yes, what the mean tweets would be.
Yeah. So maybe so I would like, imagine myself a year from now being like, how great is it going to be to have this collection of just ridic, all this like harsh, toxic stuff that's been said about what I write and what wouldn't be funny to laugh at that? Yeah. So little things like that in my case. But I think actually a lot of people who didn't grow up, perhaps with social like, you're going to have to navigate that in whatever way that works for you to also stay consistent, even if you've got the team thing figured out.
And I think it's a really important thing to do because, you know, I'm on seven boards, I'm on, I'm on one board, big company, thousands of employees. The way the CEO communicates with his employees is by sending out a PDF that he's hoping gets read and posted in a break room. There's you know, no social presence. There's like, he's not meeting people his team where they are, write and read.
Send out a video. Yes. You know that can be linked to directly off the email or something. So my journey actually into creating was as somebody who kind of grew up in web 1.0, felt like I got to learn how to use these tools, because if I'm going to be a modern leader, you have to learn how to use these tools.
So it's a question I actually have for you. Yeah, I'll ask you. I'll answer it for me. Okay. Do you identify more as a creator, a CEO or an entrepreneur? For me, I'll just say I identify more as an entrepreneur who has felt like he needed to learn and wanted to learn how to create and realize, oh, through creating, I can have impact.
teach and help more people. But it's fundamentally I'm still more of a of an entrepreneur. at these retreats, we've had the spectrum of hardcore creator first, hardcore entrepreneur first. How do you answer that? It's a good question. I'm just thinking about it's somewhere between creator and entrepreneur. Okay, those are the two that overlap the most. CEO is very much a skill that I am in the process of learning.
Yeah, I guess it'd be worrying or worrisome if I was like, I got that mastered and like that is clear evidence that you don't have that, you know, maybe 75% creator, 25% entrepreneur. And do you feel like ConvertKit? I know it really serves creators right, but how do you think about it? I think about for your business a little bit on this, this continuum.
I think there's this huge opportunity for CEOs and business leaders who need to still learn these tools who are like sleeping giants, who are not not doing this stuff at all yet, who need to learn from creators. I continually at these retreats and blown away by the power of the audiences that these attendees have. So you're talking about the CEOs really diving in on the and like becoming a creator within either, well, not just within their company, but but far beyond that.
Yes, because people are far more interested in following people, not brands. Correct. Which then means the leader has to be show up, show up as a person, as a person, and that is a brand. Yeah. You know, so so one of my theories is a modern CEO. Or they could also have an audience co-founder or somebody on the senior team.
Right. It's got to have 10% of their time spending and creating an example of that would be the company Ahrefs, which is the SEO company. I'm trying remember the founder and see his name, I think. Dmitri. Okay, maybe very, very technical, brilliant guy, brilliant coder, but the kind of person that, you know, goes and builds a product that indexes the entire internet just because it's fun, you know, and then maybe, like, rewrites it a few years later just for the heck of it.
Tim, who's the CMO of Ahrefs, is the face of everything, not the original founder. But to your point, there needs to be someone that everyone's like, oh, that's the guy. You know, Tim has built a very effective personal brand. Another example would be Cameron Harold. From what I got John, I just had him on the podcast a couple episodes ago.
Call and he's the one, you know, he built this massive personal brand that he used to help grow the company substantially. So there's there's definitely examples of of people doing it. One thing that I struggle with is, you know, being originally creator first, may we balance I can work it's brand versus Nathan. Very brand originally Nathan very brand relatively speaking, is much bigger convert.
You know, I'm using that to grow ConvertKit. And there's sort of this middle season where my brand and my content fell to the backburner. And then ConvertKit has become so big, even to the point I was doing a trip to Denver. This is maybe 2018, 2019, and looked up some of our top customers in Denver, send them emails, and hey, I missed that.
I found in ConvertKit. I'm going to be in town. I'd love to take you to coffee or lunch or something and just meet up. And I get this email back from this woman who runs a, big popular photography, community and, and all that. And she replies and goes like, yeah, I'd love to, but like, there's a couple days between the reply and I was like, all right, sure.
And so we meet up and she goes, you know, I have to tell you something that when you emailed and you said you were the founder of ConvertKit, I was like, oh, you're not. ConvertKit is founded by a woman. And I was thinking about like, where did that come from? But it's because, we have this amazing creator on our team.
Her name is Issa, and she taught all of our webinars. And so the perception was that to someone, you know, loosely paying attention was that she founded the company even to the point that, you know, this customer's like, who's this guy who's like, Posie? What the what is this? And then she looks at me, oh, I understand what's happening.
I guess all that to say two things. One, having people who within the company build that profile and, are well followed. And then two ConvertKit, you know, ConvertKit brand really eclipsed mine. And so now what I'm thinking about is if we looked at act three and should I really scale the personal brand Books podcast, you know, training courses, all of that to really get my methodology curriculum out there, to really get ConvertKit into all of the rooms that we're not in now.
Like, hey, I have a software company that's doing 40 million a year in revenue. Can I go on your podcast? Sort of like, I don't know, maybe, but I have this book coming out. I'm on book tour. Can I go and absolutely line them up? You know, and so I'm thinking about that balance of what does that look like?
And I'm curious some of your thoughts. Well, commerce follows trust okay. And trust if you study the science of trust, which John Gottman has, has he wrote a book on it? Yep. You know, trust you can lose in an instant. But trust doesn't get built in one grand gesture. It's it's actually tiny repeated motions over time that generates it.
Right. And that's one of the opportunities that consistent creating and just I would say doing more with your personal brand. Right. I think it's going to be a big opportunity if you do do that. I mean, you already built an amazing start to that. And the foundation is there. Yeah. And if you if you scale, that and you have so much to teach from your experience.
Okay, let me dive into the four like idea that I have. Tell me. But before that, you ask the creator entrepreneur CEO that question. And what I'm wondering is what's the question behind that question? Like, is there something that, depending on the answer to that would take you different directions? Yeah, identity is I mean, so I would argue the most powerful force in like the human personality and I was curious about it for you, partially because as your business grows, you've been serving, at least as I understand it, people who have their identity as creators, I think there's a potential huge opportunity still serve them extremely well.
Yeah, but what about entrepreneurs who are more like me, who still identify that way? Or leaders? Yeah, but like need to add a sprinkle of creator into their identity. Yeah. and they need a lot of guidance tools, and support where how to welcome them into the group and build tool because there's an enormous business case for them.
Right. But that's interesting because I'm very much focused on the pure creator. That's right. Right. How do we scale that? How to which is fantastic. Because if and that's also for me, why I want to work with ConvertKit more as the identity of the entrepreneur. Let's go with the platform that has solved it for the people who are doing it, who are the best basis yet.
Well, I think the world is still relatively asleep to is, how important integrating aspects of being a creator into modern business leadership. Right. And there's a meaningful budget there. And everything very I mean, business case. Yeah, right. I'm intrigued by that. I think there's a version of, iteration of Paper Boy and the newsletter growth agency that we take where it's like doing more of this for you.
Yes. To make it take the content you already created in your business or something, because, yeah, a CEO is like, I'm going to hire a team. I hire a team for everything. If I'm going to do this creator thing, seriously, I'm going to hire a team for it. And so if you could, it could be that team would be interesting.
I mean, you have it, you have a team. Now, maybe talk a little bit about what your team is that supports you in the level of creating you're doing today is and then what you would, might, yeah, might need to envision if you go after this big sway. I have the whole team at ConvertKit, which is 76 people I think right now.
And then more contractors beyond that. But that's that's our core team. And then on the personal brand side, what I'm doing is I've got a book that I'm working on a flywheels course that I've done, I've got Twitter, which has grown well, but kind of stalled out as I haven't been consistent with it. Do a little bit of Instagram, do the podcast, and all of that is supported by I have a head of content and she's fantastic.
She does a lot of writing. She knows my voice very, very well, and we'll co-write a lot of things together. things like when I did the flywheels course. She's the one that will interview me and we'll talk through it a whole bunch. And then she'd be like, okay, now here the everything we talked about here, it is organized in four lessons, you know, or and in sequence like that.
and then I have an agency that supports me on the podcast. They do the editing, the clips, the promotion on, you know, Instagram and YouTube and that's it. That's the entire. So it's very lopsided, right? If we think about it, actually, if I think about the results that I'm getting on the personal brand side versus the results, I'm getting, ConvertKit like it kind of like this is a 76 person team and is adding, you know, many millions and millions of dollars a year in revenue.
And this has a one and a half person team and is kind of stalled out. And I guess that like that points to some of the problem. And if you were to take the bigger swing, what would be some of the key pieces you would imagine adding to that team to be more consistent? And, you know, hit this goal five books in five years, like all this?
Yeah, I have so many like, so many ideas for content. Yes, because I write these flagship essays that I spend months on, get all my friends to help, like critique and co-write and, you know, all of that. And they get reference for years. people are like, this essay is better than rich dad, poor dad. And like, just needs.
But I can't like gift the essay to my son for high school graduation if I can. You know, rich dad, poor dad. Right. And so I yeah, I have all these ideas. Five books lined up, to write. I there's a lot, I think the one that I'm really wrestling with the most is what to do with the flywheels content, because there's two versions of it.
One is honestly the half assed version worthy. My priorities are in other places version, and that's like, make the course like finish it out. You know, record it with a fantastic video team and all of that, taking 25 people through the cult, through like the live cohorts as I've created. So finish that, put it live, sell it for $1,000.
So it's, you know, a premium or 1500, it's premium price point and then just have that exist. And then the other option is turn it into like a substantial program, like a group coaching program that people are paying 5 to $10,000 a year to be a part of. It's a course that deep dives into all of this. Maybe there's a, call every other week where I'm working through, like, teach you flywheels live.
Because the thing is, like, it requires that hands on application, you know, people are like, oh, I watched them, too. I kind of got it. And then I said, like, okay, let's make your flywheel. And we map it out and they're like, oh, now interest and everyone else watching is like, now I get it. I have all these friends like, Mike Brown, Dan Martell and others who have built these coaching programs that do millions of dollars a year in revenue.
But even that, even if you build that coaching program to $3 million a year in revenue, like ConvertKit, you know, is that $43 million in revenue right now. And so I, I like struggle. Should I just put all the time into the main thing, or is there a way to tie it all together? I don't know, it's a big open ended question that I'm wrestling with here in Cabo at a mastermind.
I mean, I'm not going to claim to have the answer. And by the way, one of our principles at these masterminds is experience year over direct advice, which I think is also like, I'm down for direct advice to anything, but yes, but I think what I'm more torn on is your time investment related to the bigger coaching piece and all that sort of stuff, right?
What I will say, what does really resonate though, on my journey of stepping in to create or like I have really leaned on the support of basically like cohorts, peer groups, and effectively I cobbled together what you're describing. Right? And it's been absolutely essential. it's absolutely a need. And I can see how it's synergistic with ConvertKit. What I worry about it.
Is it being a time vampire for you? Right. So then the quote, one of my favorite questions, I don't know where I got it. I don't know if it's from, Dan, my coach from reboot or something else, but very question is what would have to be true. So what would have to be true to do all this content creation that I'm talking about.
Right. Like I look at people like Nick Uber others who. But the power of the audience is just insane. And I experience that every day. You know on a smaller scale, you know, I have 100,000 Twitter followers instead of 4 or 500,000, but for recruiting, for fundraising, everything, it's so much easier. But going back to the question, what would have to be true in order to like, fully maximize the personal brand, go all in and have it be a 5 to 10 hour a week endeavor, maximum.
I think one of the biggest lessons of entrepreneurship, as an aside, is not spending enough time on the right questions. And that's such a good question because it just immediately like you've already now framed up, like, I want to lean forward into answering that and it sparks for me, certainly at least 1 or 2 more senior hires, right, who are going to help you both on the content and the app side of this whole operations, and who also are going to have budget and authority to, manage some people underneath them, I mean, at minimum at a high level.
Right. because otherwise you're not going to hit your 5 to 10 hour mark. The other thing that comes to mind to me is it feels like you could teach the core curriculum via video and then certain, like strategic drop ins and coaches could be trained to do that in my methodology. Yes. Yeah. And I think still provide a ton of value.
I mean, from a flywheels perspective, if you did it in that way, the other thing that would be cool is from the program and the students themselves, their questions, challenges, whatever. Yeah. Your feeds the flywheel, right? Because it's like, what are the biggest questions from the community this week? Or what are we going to address in the group coaching?
You know, on that call maybe I'm on half of them, I don't know. Yeah. someone is presenting their flywheel. Yeah. Other people are saying, oh, but you're actually like number three. You didn't quite implement that. What if you had this tweak or asking, hey, what step in here has the most friction? All questions that I've taught people to ask.
But then that's happening live without requiring me to be the one person doing it. Like if you do it, I think you should solve it with the constraints of your question. Right? yeah. Be very clear because I, I like threw them at that out there as hypothetical constraints or like, you know, something like this, but to say, no, these are the concrete.
Yes. You cannot deviate from yes to the content team. Whoever I hire, it's like I am accessible on these exact time. Exactly. You have this amount of time for me to record content. Yes. You know, and it's not like, oh, sorry, we weren't super prepared. And so I guess we'll run long, right? Like, you might not hit your content goals this week because, yeah, we sat down to record and you didn't have script ready.
Yep. Yeah. So hard constraints. What else? I mean the the other I think feature of the problem that you're solving that these platforms and just the job of a creator like it's such a dynamic marketplace. And while there's timeless principles to what you're teaching from a flywheel standpoint, like the craftsmanship of how to apply those principles to the current state of the art right is in constant flux, given the dynamism of it is.
And and so there's tremendous value of community and coaches who are just basically on the edge of what's happening and what's actually like doing regular breakdowns of what actually works, because there's so many times that I see something working and I'm like, oh, there's a flywheel there. But then it takes me a while and a few iterations to be able to clearly define the steps of the flywheel.
I'm like this. Yeah, I know that that loop closers not quite there. and then, you know, some of the few other times I come back and I'm like, that's it. And then I can explain it. Well, and an example of this, my partner, Silas Bloom, I, he's just told me interesting stories of big time, huge creators from like five years ago who are now reaching out to him on helping understand what's working right now, what's working right now.
It's evolved. And they don't they don't know. And there's value to being on that edge. And that's that's a real need. Going back to one of the earlier questions on the core company. Yes. Versus the personal brand. Like this is what I wrestle with. And I think I have an answer, but clearly not with a ton of conviction of is the personal brand the best way to grow the core company?
And it's not either or, but but like, is it worth it to take that time away from the core company? Or is it like, no, I think it's capped. I think if it's capped at 5 to 10 hours, yeah, a week, which may be a lot for an average CEO, but you're also in a business that's like serving creators.
So like yeah, yeah. Like living and breathing our own products, our own methodology. Yeah. Like I, I'm not sure Sam Altman needs to do that. Right. but, you know, Sam Holman has a pretty big personal brands that he's like his personal brand was essential in navigating that. The whole board. Right. so yeah, because there's so many people who are like, I don't know what happened, but I trust Sam.
Yes. And you're like, why? Well, because of personal brand that's built up over the last 15 years. You know, I remember with the caveat that I generally lean more towards the direction of go big or go home. I like the idea of keeping it super constrained for your time and going for it, and then having there be like clear markers, like it's got to have x, Y, and z progress.
So that. Right. Yeah. Well that's interesting. It's something that I notice a lot of people do, and I do it myself, is to put things on two ends of the spectrum where it's like capped out on my time, or go big or go home. And something that I always try to do is go, okay, what if those are two different instead of a single axis?
What if those are two different ones? How much time does this take and how big is this? And you're like, okay, what exists at I guess it'd be all the way down here. The least amount of time and the maximum output. And so if I said the constraints are, go big and ten hours a week, then that brings us right to team, you know, and instead of saying, okay, we need more of a budget team, they're just managing social, all of that.
It's like, okay, we need real a players and probably a, you know, instead of going from one person to two, we might be going from one person to 5 or 6 to run this. And then that begs the question of how do you work into that? Is there like gradually iterate, you know, hey, we're going to make an additional hire.
And then six months later, we're going to evaluate where we're at and make maybe make another one. We're going to start with some, you know, one more full time hire and a contractor. Or is it like, no, we designed the full blueprint to the best of our knowledge right now, knowing some of it will change. And we're going to make five A-plus hires right now.
What do you think my quick bias going back to your time constraint is the first additional hire might not need to sit at the top. You might already have that person. Yeah, but it's the first additional hire is more senior than junior. It's probably one senior higher. Yes. And then and then part of their job will be to iterate through whatever reasonable sequence versus if you if you iterate into a junior hire, then you're going to kill your time constraint.
Right? There's that I was laughing, I was thinking about random constraints. Like I would immediately get a designer in not full time, but on a contract, because it's a very easy thing to have brand style guide set. This is the way we do it. And then work with these designers. But I was laughing because I still do a bunch of design because that is my core original skill set.
And here's the mini. Like that is the fastest way to blow through your hard time gap. You know, it's like, go, do you know, $100 an hour work as a designer? Oh, so you might also need as part of the solution. I know you already invest in coaching, but you may need somebody who can essentially, hold you accountable for not diving into the which is the hardest thing to do, you basically spending time on that design love that you would love to do.
Yeah, because it's the it's fun. And it's one of those things that I'm very, very good at and it's just not a good use of my time because there are people who are not that expensive in the grand scheme of things who are just as good as I am. Yeah. So a question I would maybe leave you with is who or what system could hold you accountable for that risk related to, you know, your time goal?
Yeah. So we're kind of coming to it from a few angles. One is clearly defined. The time constraints and set the schedules right. This is exactly how we can show up. This is when I write. This is when I meet with the team. This is when I sit down and record that kind of thing. And then from there, you know, that's one side.
Then go to the other end and say, okay, what is go big look like on this? Because we can't mess around with the little $500,000, your creator business, because that's a waste of time. But if you can get to a $5 million a year, or even a $3 million a year creator business that really feeds ConvertKit, then that's where it hit.
So, you know, small time constraint or very clear time constraint, very big goal. And then these pieces start to come together and say, okay, what team has to exist to work within this? And then we go to what are the traps and pitfalls that are likely. Now, how am I going to know if I'm falling into those? And who's going to be like, did duh, you know, but don't do that right?
You know, whether it's a coach or, more of a peer mentor who's saying like, hey, why don't we do a once a month call or you send me a ten minute video update once a month of how the personal brand stuff is going and they'll be telling me you're like, oh yeah, what did you spend your time?
You know, like, I mean, you could probably send a five minute loom once a month to Nick Huber, and he would send you back a like two line text to tell you what, you know. And, that's one solution. Would probably work really well. You get a profanity filled audio memo back, do all of this differently and these exact things.
Yeah. And I think, like you and I can both really want to feel like we've methodically thought through a lot of things, which is both a beautiful strength, but also in some of these areas can like there's a downside to it. And, so whether it's him or not, I'm sure he and he, you know, you do it.
He would totally do it on here. You just send it to the camp. There you go. Do that. And then there's a solution, right? Yeah. Here's the the monthly update. Yeah. How it's going. Do you think that I was realizing is I can separate the creation and like, I need to, identify the difference of the creation versus the maintenance, because some of these things, like the flywheel, of course, is a good amount of creation work, but not that much maintenance work.
But then there's other things where, you know, I got to the point that I've got 30 to 40 threads that I wrote on Twitter that do really well. I reposted that multiple times and and it's done great. and that's how I grew from 30,000 to 100,000 followers in a year. And then the next year I had like 25,000 followers because I, like, I took my foot off the gas and I didn't have the system in place, which I guess is ironic since I teach a course on flywheels, but it's one of the like one of the lessons of flywheels is they're not perpetual motion machines.
They still require some level of. But it might be the equivalent of standing there with two fingers to just barely keep it spinning. But if you stop and you walk away and you come back, while later you're like, why did it stop? That's like, well, and you may need to build in some like slack in the system, compassion for yourself, what have you in the beginning to make that initial creation investment that might not be able to look like five hours for that week, right?
Right. but that's that's different, so long as it's in service of, you know, getting to that goal over time, how it all fits together in those key hires, any any thoughts or insights on how to go about vetting that talent and what to look for? It's going to be such a fun journey to be part of this team for the right people.
Right. And so I would do a little thoughtful design of what's a case work sample that you can do that would help demonstrate somebody is a good fit for this, which you could delegate. but we, I go to work product immediately because there's going to be a lot of people who are excited, you know, going have way too many applications for this.
And what what made sales chief of staff who's kind of leading an effort like this, be such a great fit? He basically had years of work product that he could look at, right? You know, you don't have to go that far, but at least get a taste there. I would say. and yeah, I think that's one of the just like the key things to, to start with.
And you actually did a monthly update to the camp cargo text to read the ships would be burned right? For better or worse. Yeah. Well, I mean, I like it because I know that that business really thriving, the books being written, all of that would grow ConvertKit in a huge, huge way, in a way that our competitors can't touch.
Yes. Right. Because they're doing things, you know, copying features that we come out with and all of that. But like, they can't really copy the curriculum without it being obvious. They can't copy the content that builds all this trust. and, you know, all the goodwill that comes from that. And, I mean, you are a world class learner.
Yeah. And I mean, it's like, yeah, you are world class learner. That then feeds being able to be a world class teacher. Yeah. And this allows you to bring that with more scale and support into the world. That is yet another thing that competitors can't touch with you, right? I love that man. It's been fun. Really fun. Not just this episode, but, you know, camp covers a pretty good time too.
Excited to see where we are a year from. A year from now. Yeah. Where should people go to follow your content and learn a little more about you? I'm, most active on Twitter and LinkedIn at Matunuck. and, we hit sale and I have some things coming soon at the inflection.com. Sounds good. Thanks for hanging out.
Awesome. Thanks. If you enjoyed this episode, go to the YouTube channel. Just search Billion Dollar Creator and go ahead and subscribe. Make sure to like the video and drop a comment. I'd love to hear what some of your favorite parts of the video were, and also who else we should have on the show.