Team-Building Expert: 4 Steps to Building a Personal Brand Team

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 encouraged 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 is just a little sprinkle and then they can fly.

You know, I love coaching in Billion Dollar Creator and I'm usually the one coaching someone else and 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, 1.5 person team.

Do you identify more as a creator or an entrepreneur?

I've got Twitter, which has grown well, book that I'm working on, do a little bit on 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 gonna 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.

Perfect timing.

Perfect time. But the company that I worked for survived. It was an early company that was pioneering trackable customer acquisition. They wouldn't have called it an affiliate model, but it was pioneering affiliate stuff. It was called QuinStreet. 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 sea of, at the time, like 22-year-olds starting companies.

Right.

I was able to start a business when I was 25, kind of based on what I'd learned there, bootstrapped that. It was essentially comparison shopping software that was in the insurance industry and sold that company to Bankrate 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, uh, I oversee. I'm on 7 boards, uh, ranging from startups to companies in some cases that are doing $3 billion in sales.

Hmm. So now at this point you're doing a personal holding company before, like now it's almost a meme on Twitter, right? Yeah, exactly. But you didn't plan to get into that in a way, you just—

No, 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 in.

Right. How many companies do you have at least 25% ownership in now?

4 now. And that's plenty.

That's enough.

Yeah, yeah.

Though we've been talking here about another business you wanna start.

Yes, exactly, yes.

We say that's plenty, but—

Yeah, that's a good point.

The serial entrepreneur.

That's a good point, that's a good point, yes.

You keep coming 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 something that you've done that's interesting is first being a student for a long time.

Yep.

And really exploring a lot of different coaching methodologies. And I wanna get into that a little bit.

Yeah.

But then also coaching, you know, if we think about coaching from a billion-dollar creator perspective.

Yes.

It's a service. It's time for money.

Yep.

Now you've taken a different approach. It's always stood out to me of saying like, what if I own the companies that, and I 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 $10,000 a month, you say, what if I own 75% of the company? 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've studied almost every great executive coach that I could find.

Who are like the top 3 that you—

Well, I think people worth really looking at, it's worth looking at Marshall Goldsmith, who was one of the early pioneers in performance-based executive coaching. So he'll coach Fortune 50 CEOs, CEO of Pfizer, CEO of Ford. I think Matt Mushari is an interesting one to look at. I would say is one of the more respected in the VC-backed world. So he initially coached Naval. Naval then introduced him to Sam Altman. Sam Altman then introduced to him. And then I also think it's really interesting to study coaches in other disciplines. Like, why is Greg Popovich a great coach? I like to pull from all of those disciplines. I've been heavily influenced by Dr. John Gottman, who could predict divorce with 91% accuracy because he identified, you know, these 4 patterns of conflict that are toxic. I went to go study with him and I realized those are the same things that kill a company culture.

Yeah, it 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 toolset then allows you to be a really effective entrepreneur or acquirer of businesses or— Right. Yeah, to be in the 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, 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 it 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 could just charge for money. That could cash flow. Over time, I've had to learn how to put that part of me in its place because otherwise I just sort of stay in small mode.

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 decided not to because I just have more fun and I like the risk and the upside of aligning in deep partnership with CEOs.

Something that I think you're remarkable at that we talk about often is finding that talent. And then how you develop talent, both for your own companies. Then you've also found a lot of talent for a lot of our friends. You've helped them get a chief of staff in place. 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 Shortlist and it does large-scale hiring programs and now also executive search. And so I went deep on the science of hiring. I would say one of my biggest takeaways, work samples are just the most predictive of is somebody gonna 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 it back to coaching, Marshall Goldsmith, who 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 6 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.

So the takeaway?

The takeaway from him was there are people who have so much potential and 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, whatever. And the harsh truth was I could get a lot of my identity wrapped up in fixing the situation. And the reality was that leader wasn't really able to get there. 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? You know, that could be in a little case study, right? 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. Sahil was here a year ago, and myself and the group encouraged him to hire a chief of staff given the vast growth of his opportunity.

All the things that he's doing. Yeah.

All he did is hear that once. He actioned it immediately. He found a candidate and like his growth has continued 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 been coming to you for advice on. It's one that I'm considering hiring at ConvertKit. It's a little less of a creator chief of staff because of the scale of ConvertKit as a business, but they need to play in both of those worlds. I'm curious as you were thinking about all the creators listening who might be at $500,000 a year in revenue, $1 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 Gay Hendricks. And the quick and dirty way to do this is take the last 2 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, mark it red.

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 gonna help you, you wanna 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.

[Speaker:NATHAN_BARRY] I like it. What are some things that you've seen of the way that people have done this? You go two directions, either the creators that have had a big unlock because they found this is their zone of genius and they hired a chief of staff to do this. This, or 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, 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 showing, this is my exact calendar for when the 9 companies get rotated through every 21 days. And you're like, cool. There's nothing complicated about it.

Correct.

But I would say 1 out of 10 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 an 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 whether you call it a chief of staff or a creator COO 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 gonna either need to get trained up or they're gonna need to, um, you want to ideally look for somebody who has some experience, who has grown some kind of social following, an account, either their own or helping somebody else. I mean, that's, that's that's helpful or that they at least have the, the raw skills or aptitude to do this. Yeah. 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, like 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 could sort of respond to and judge. 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 and awareness of things like graduated exposure therapy and just knowing, like, I'm gonna 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. Uh, and like basically the shittiest things people said, 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.

Yeah.

You're like, I could write this. Ah, no, but I'm immediately hearing in my head what the mean tweets would be. So maybe let's not.

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 ridiculously like harsh toxic stuff that's been said about what I write and won't it be funny to laugh at that? 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 gonna 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 7 boards. 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 no social presence. There's like, he's not meeting people, his team, where they are, right?

And at least 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 and teach and help more people. But it's fundamentally, I'm, I'm still more of a, of an entrepreneur. Uh, at these retreats we've had the spectrum of hardcore creator first Creator? Hardcore entrepreneur first? How do you answer that?

It's a good question. I'm just thinking about, it's to be somewhere between creator and entrepreneur. Those are the two that overlap the most. CEO is very much a skill that I am in the process of learning. I guess it'd be worrying or worrisome if I was like, I got that mastered. It's like, that is clear evidence that you don't have that. Maybe 75% creator, 25% entrepreneur.

And do you feel like ConvertKit I know it really serves creators, right? But how do you think about— 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 am 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 show up, show up as a person, as a person, and that is a brand. Yeah. 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 gotta have 10% of their time spending creating.

An example of that would be the company Ahrefs, which is an SEO company. I'm trying to remember the founder and CEO's name. I think Dmitry, maybe? He's a 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, ah, that's the guy. You know, Tim has built a very effective personal brand Another example would be Cameron Harold from 1-800-GOT-JUNK. I just had him on the podcast a couple episodes ago. COO, 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 definitely examples of people doing it. One thing that I struggle with is, you know, being originally creator first, maybe if we balance like ConvertKit's brand versus Nathan Barry brand. Originally Nathan Barry brand, relatively speaking, is much bigger. ConvertKit, I'm using that to grow ConvertKit. And there's sort of this middle season where my brand and my content fell to the back burner. 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, sent them emails and said, hey, I'm Nathan. I founded ConvertKit. I'm gonna 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 all that. And she replies and goes like, yeah, I'd love to. But like, there was a couple of 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, no, you're not. ConvertKit is founded by a woman. And I was thinking about, I'm like, where did that come from? But it's because we have this amazing creator on our team. Her name's Isa 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 was like, who's this guy? Who's like posing? What the, what is this? And then she looks up and goes, 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's brand really eclipsed mine. And so now what I'm thinking about is if we looked at act 3, should I really scale the personal brand, books, podcasts, training courses, all of that to really get my methodology curriculum out there, to really get ConvertKit into all of these other 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? It's sort of like, I don't know, maybe. But I have this book coming out. I'm on book tour. Can I go on? Absolutely. Line them up. And so I'm thinking about that balance of what does act 3 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 wrote a book on it. Yep. Trust you can lose in an instant, but trust doesn't get built in one grand gesture. 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 gonna be a big opportunity if you do do that. I mean, you already built an amazing start to that.

The foundation is there.

Yeah, and if you scale that and you have so much to teach from your experience.

Okay, let me dive into the full idea that I have. But before that, you asked 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, some 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 to still serve them extremely well. But what about entrepreneurs who are more like me who still identify that way or leaders, but like need to add a sprinkle of creator into their identity. And they need a lot of guidance, tools, and support.

Right, how to welcome them into the group and build tools.

Because there's an enormous business case for them.

Right, oh, that's interesting. 'Cause I'm very much focused on the pure creators.

That's right.

Right, how do we scale that?

Which is fantastic because if— and that's also for me why I would 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 on a professional basis. Yet what 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 else.

Very mean business case. Yeah. Right.

I'm intrigued by that. I think there's a version of, um, if it's an iteration of Paperboy, the newsletter growth agency that we take where it's like doing more of this for you.

Yes.

Um, to make it take the content you're already creating in your business or something. Cause yeah, a CEO is like, I'm gonna hire a team. I hire a team for everything. If I'm gonna do this creator thing seriously, I'm gonna hire a team for it. And so if you could be that team, it'd be interesting.

I mean, 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 might need to envision if you go after this big swing.

I have the whole team at ConvertKit, which is 76 people I think right now, and then more contractors beyond that, but 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 on 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 will 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'll be like, okay, now here are the, everything we talked about, here it is organized in 4 lessons, you know, or 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, And actually, if I think about the results that I'm getting on the personal brand side versus the results I'm getting in 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 1.5-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, 5 books in 5 years, like all these things.

Yeah, I have so many, like so many ideas for content.

Yes.

'Cause 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 referenced 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. But I can give, you know, Rich Dad Poor Dad, right? And so I, yeah, I have all these ideas, 5 books lined up to write.

There's a lot.

I think the one that I'm really wrestling with the most is what to do with the Flywheels content. 'Cause there's 2 versions of it. One is honestly the half-assed version or the 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. I've taken 25 people through the live cohorts as I've created it. So finish that, put it live, sell it for $1,000. So it's a premium or $1,500. So it's premium price point. And then just have that exist. And then the other option is turn it into a substantial program, like a group coaching program that people are paying $5,000 to $10,000 a year to be a part of. It's the course. Deep dives into all of this. Maybe there's a call every other week where I'm working through like teaching flywheels live. Cause that's the thing is like it requires that hands-on application. You know, people are like, oh, I watched the material and I kind of got it. And then when I say like, okay, let's make your flywheel. And we map it out and they're like, oh, now I understand. 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 at $43 million a year 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 shares over direct advice, which I think is also like a good—

I'm down for direct advice too, anytime.

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— what does really resonate though on my journey of stepping into creator, like I have really leaned on the support of basically like cohorts, peer groups, and effective— 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 is it being a time vampire for you, right?

So then 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 favorite 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 Huber, others who like the power of the audience is just insane. And I experience that every day, you know, on a smaller scale. I have 100,000 Twitter followers instead of 400,000 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 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 'cause it just immediately, like you've already now framed up, like I wanna lean forward into answering that. And it sparks for me certainly at least one or two more senior hires who are going to help you both on the content and the ops side of this whole operations. And who also are gonna have budget and authority to manage some people underneath them. I mean, at minimum, at a high level. Uh, 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 in my methodology. Yes.

Yep.

And I think still provide a ton of the 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 feeds your—

feeds the flywheel, right? Because it's like, what are the biggest questions from the community this week or what we're going to address on the group coaching? You know, on that call, maybe I'm on half of them.

I don't know.

Um, someone is presenting their flywheel. Other people are saying, oh, but you're actually like law number 3, 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. 'Cause I like threw them out there as hypothetical constraints or like, you know, something like this. But to say, no, these are the concrete constraints. You cannot deviate from this. To the content team, whoever I hire, It's like, I am accessible on these exact times.

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. It's like, you might not hit your content goals this week because we sat down to record and you didn't have scripts ready.

Yep.

Yeah. So hard constraints. What else?

I mean, the, the other, 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 is in constant flux given the dynamism of it. 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 are 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 closer is not quite there. Uh, and then You know, sometimes a few other times I come back, I'm like, ah, that's it. And then I can explain and teach it.

Well, and an example of this, my partner, Silo Bloom, he's just told me interesting stories of big time, huge creators from like 5 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 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 like, is it worth it to take that time away from the core company or is it like, no, we're gonna go business.

I think if it's capped at, 5 to 10 hours 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'm not sure Sam Altman needs to do that. But, you know, Sam Altman has a pretty big personal brand that he's like, his personal brand was essential in navigating that. The whole board.

The whole board.

Right? So—

Yeah, 'cause 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 been built up over the last 15 years, you know, or more.

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 gotta have X, Y, and Z progress so that Right. Yeah.

Well, that's interesting. 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 on my time or go big or go home. And something that I always try to do is go, okay, what if those were two different— instead of a single axis, what if those were 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 10 hours a week, then that brings us right to team. 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 instead of going from 1 person to 2, we might be going from 1 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 gonna make an additional hire and then 6 months later we're gonna evaluate where we're at and maybe make another one. We're gonna start with some, you know, 1 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 that some of it will change, and we're gonna make 5 A+ 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, I think you do.

But it's the first additional hire is more senior than junior.

So it's probably one senior hire.

Yes, and then part of their job will be to iterate through whatever reasonable sequence versus if you iterate into a junior hire, then you're gonna kill your time constraint.

[Speaker] Right. I was just laughing, I was thinking about random constraints. Like I would immediately get a designer in, not full-time, but on contract, 'cause 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 'cause I still do a bunch of design because that is my core original skillset. Skill set. And he was immediately like, that is the fastest way to blow through your hard time cap, you know, is to 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, you may need somebody who can essentially, uh, hold you accountable for not diving into—

right— the—

which is the hardest thing to do. Yeah, you're basically spending time on that design love that you would love to do.

Yeah, because it's the— it's fun, and, 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 your time goal.

Yeah, so we're kind of coming to it from a few angles. One is clearly define 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 we sit down and record, that kind of thing. And then from there, that's one side, then go to the other end and say, okay, what does go big look like on this? Because we can't mess around with a little $500,000 a year 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 worth it. So, small time constraint or very clear time constraint, very big goal. And then these pieces start to come together and it's like, 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 gonna be like, dude, don't, 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 10-minute video update once a month of how the personal brand stuff is going. And they'll be able to tell me like, oh yeah, what'd you spend your time on?

You know, like, I mean, you could probably send a 5-minute Loom once a month to Nick Huber, and he would send you back a, like, 2-line text to tell you what's up, you know? And, um, that's one solution that would probably work really well.

You'd 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 it 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.

I think you just send it to the Camp Cabo. There you go.

Do that. And then there's a solution, right?

Yeah. Here's the, the monthly update on how it's going. The other thing that I was realizing is I can separate the creation, like I need to identify the difference of the creation versus the maintenance. Because some of these things like the Flywheels 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've reposted them multiple times 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 added like 25,000 followers because I like, I took my foot off the gas and I didn't have the system in place. Oh, which I guess is ironic since I teach a course on flywheels, but it's one of those, like one of the lessons of flywheels is they're not perpetual motion machines. They still require some level of input. 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, then you come back a while later and you're like, why'd it stop? It's like, well—

And you may need to build in some 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 5 hours for that week.

Right.

Right? But that's different so long as it's in service of getting to that goal over time.

How it all fits together. In those key hires, any thoughts or insights on how to go about vetting that talent and what to look for?

It's gonna 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's a good fit for this, which you could delegate, but But yeah, go to work product immediately, 'cause there's gonna be a lot of people who are excited, you know, we're gonna have way too many applications for this role. And what made Sahil's 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 start with. And you actually did a monthly update to the Camp Cobo text thread, the ships would be burned.

Right.

For better or worse.

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, um, and, you know, all the goodwill that comes from that.

And I mean, you are a world-class learner. Yeah. And I mean, yeah, you are a 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. And I love that.

Matt, this has been fun.

Really fun.

Not just this episode, but, you know, Camp Cava was a pretty good time too.

Excited to see where we are a year from now. 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 @MattShnook. And we hit, Sahil and I have some things coming soon at theinflection.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.