Success Story: How to Scale a Coaching Business to $1M+

You've gone from no revenue in the business to $1.1 million, and to do that in 4 years is absolutely phenomenal. My guest today is globally recognized career strategy coach and workplace expert Tiffany Newman.

Any creator or coach even that's looking to build their business and really scale beyond the $500K mark, it's about looking at what's bringing the most value in their business, but what's also creating some risk for them. For me, that was the key man risk where it's so attached to you actually helping, or is it holding you back? In our case, I felt like it was a limitation.

Something that I hear you talk about a lot is the 4 pillars that you've used to really scale your coaching business.

The 4 pillars, first and foremost, is coaching. The second pillar is the media side of things. The third pillar is events and experiences. The fourth one that really is now starting to tie it all together is—

was there a particular tipping point or a breakthrough that happened where you're breaking 1.1 million?

I really challenge myself to think bigger picture. Where do I want this to be in a year from now, 2 years from now, 5 years from now? And use that to reverse engineer back what changes need to happen. I'd say one of the big shifts that helped and was very much needed in the business was—

Tiffany, something that I hear you talk about a lot is the 4 pillars that you've used to really scale your coaching business. And I, I'm so excited to dive in behind the scenes on how you run your business and so much else. But let's start with what are those 4 pillars?

Yeah, sure, Nathan. Happy to jump into that. And I will say that back in 2024, that was really the year that we kind of really outlined that for ourselves. So the 4 pillars, first and foremost, is coaching. That's been the primary revenue driver for us since the inheritance of the business and where we started back a little over 4 years ago. And that's really where our customers learn firsthand the practical guidance and coaching support that we give. The second pillar is really the media side of things. And so that's where content has always been at the heart of the business. And this year, we are also bringing to life our YouTube video podcast that is going to really elevate us as the authority in our space and really bring light to incredible storied careers of industry leaders and the movers and shakers within the consumer brand and tech space where we really choose to focus. The third pillar is much more around events and experiences. Our community, our clients have been craving that. And up to now, we've done a lot of that online. Through workshops, and that's been very successful for us, typically delivering 6-figure to multi-6-figure launches consistently. But this is really the year where we want to take that offline and bring more of that in-person experience and plan for our in-person events starting in the spring. And then I'd say the 4th one that really is now starting to tie it all together is B2B, and that is where we are going on the inside of the companies, the very companies that our clients either aspire to work for or already work within, and do the work that we've typically done for them individually inside out. And we've been able to do this with some really major organizations, some with companies like Microsoft, and are already seeing the really tangible impact and that practical guidance that they just don't typically get in the way that they can lead their teams and drive that growth. And so for us, that's really helping to fuel this flywheel back into the coaching and the bigger mission of the business.

Yeah, well, you can't say the word flywheel without me wanting to learn so much more. So we'll get into that.

Sure.

But first, what's the transformation that you're creating for your clients?

Yeah, I love, you know, the episode you had also with Ali Abdaal really spoke to me because you talked about being in the business of transformations. And that's something we live and breathe like every day, quite literally. We've seen so much transformation in helping them unlock their fullest potential. Like, simply put, that's what we do. It's how we coach them. It's what they learn in terms of the skills to deliver on that. Whether that is, you know, more fulfillment, more happiness, more income, more growth. You know, for example, we had one of our clients who had a really negative workplace that had just crushed her confidence and helping her rebuild that and go after the role that she absolutely wanted. And now she's thriving there. And those are really the transformations we love to see and really nurture for them to bring out their best self.

You know, there's so many people who talk about needing to leave that company to get that transformation. You know, if you were to read a Reddit thread, right? This is always like, the threads are something like, my boss did this, or this interaction happened at work, what should I do? And it's like, quit that company. Or if it's something like, oh, my spouse did this, divorce them, you know? And so you're saying like, no, we're like, within the current circumstances, without like blowing everything up, you're saying, no, we can create a transformation right here.

Oh, 100%. And don't get me wrong, there are going to be moments where that change is going to be needed, but you're so right, Nathan. I mean, there's a lot of that narrative around, you know, corporate is the worst. We have to escape that. It's a rat race. And I think that's what really fuels what we do because I genuinely loved my time in corporate. I loved my time with L'Oréal. And there are ways to navigate that. You just need to know how. And so our big thing when it comes back to the transformation is making sure people have options, that they don't feel like their back is against a wall and it's like, OK, I guess exiting is my only plan. That might be the right choice for them, but we want them to feel really empowered in making that choice confident.

Yeah, that makes sense. Okay, I want just a little bit of background of your time at L'Oréal and then what it looked like to move into, you know, being a creator full-time.

Yeah. Oh, I love that question. So, you know, I get that often because it was a really fruitful path for me at L'Oréal. Could have stayed there long-term. And when I look at what I had achieved and especially what my teams had achieved, it was a lot around accelerating growth and problem-solving. And just like you're saying, Nathan, you know, when you're in that environment, you're getting you're going to be faced with challenges, you're going to be faced with hardships. And the way that I kind of grew myself and our teams was something I actually loved doing the most. And so that was a huge spark in really building the business from the get-go of taking a pretty bold move at the time. It was scary, but there was this drive that just was pulling me to make a bigger impact, and I knew I needed a platform to be able to make that impact. And remaining there wasn't going to be that option for me anymore. So that was really the catalyst of taking what I did there very well and being able to make a bigger, bigger flow with that with other people, even outside of, of that organization.

So did you leave L'Oréal and immediately start your creator business?

So I did a little bit actually while I was on maternity leave. So the plot thickens because I was on maternity leave with my second child at the time and I had wanted to start something even years prior to that and just kind of got in my own way, you know, talk myself out of it. I was like, no, I feel like I've got a good thing going. I shouldn't ruffle any feathers. But then when that second one came around, it was just this drive that I'm like, no, like, Tiffany, come on, like, give this a shot. What do you have to lose? And I really gave myself that maternity leave as that runway to just like not have a plan B. I— that was always my mindset at the beginning. I'm like, do this as if you don't have a job to go back to. Do this as if your life depends on it and failure is not an option. And I really think that's what helped me get it off the ground so quickly and built enough traction. But by the time it was time to choose to go back, I made a pretty confident, bittersweet decision to do it. And honestly, Nathan, like, I have not looked back since.

I love that. And just taking this, you know, moment of big life change to say like, okay, no, there's actually one more change that I want to make as well.

I know, right? Throw it in. The baby's not enough. Having two kids under two is not enough. It was a big one. Start a business. And, you know, I mean, I think that's, you know, so relevant for creators out there because it's all about the choices that we make. And I worked my ass off that first year. I mean, you know, you know, having young kids at one point too, like you're scraping for hours in the day. But I was working the nights, the weekends to do what I needed to get that off the ground because I was committed to the bigger purpose and the mission that we still hold true to the business to this day of bringing that practical guidance, empowering incredible professionals to bring out their best and potentials. So it all kind of ties back to that. And it was a grind, but I think well worth it.

Is there anything that you would say to someone who's in that position of maybe even, it could be broadly like a big point of transition, but maybe even very specifically of on maternity leave and saying, hey, I actually want to make this other change. You know, I want to launch a business here as well.

Yeah, I mean, I say like, be bold and take that chance because you really have nothing to lose. I think that was something I kept in the back of my mind. And especially for someone that might be coming from a company setting, a corporate setting, it's not going anywhere. You can always go back. And I always knew that at the heart of it, that if things changed and I made a different decision, I could do that. But when you have that drive in you to take that chance, like, that doesn't come every day. And if you don't nurture that and pour fuel on that, it can easily disintegrate. And so recognize those moments would be like my biggest advice. If you feel like there's been that side hustle that you now really want to fully go full-time on, or something has shifted in your life and you're like, I owe it to myself now to do it, take that chance because your future self will like really thank you for it.

Okay, so you said there's nothing to lose. I feel like it's actually a pretty risky decision. Now in this case, you're saying that you can there's nothing to lose because you can start the business while you're out on leave from the company. And then at this moment when it's time to go back or not, you can say, I'm actually going to come back because I didn't get as much traction as I thought. Or, you know, no, I'm going to go all in.

A little, yeah, a little bit of both. I mean, I would say especially if you're starting it more as a side hustle and it's something that you plan to maintain and grow and keep going without detracting from the role that you go back to, that's a great option. That was always an option I had in my mind. I just chose to kind of bite the bullet and do the whole thing at once in making that call. But I would also say, you know, obviously don't be rash about it. Like you wanna be able to have some type of financial stability and security. I, you know, had really supportive husband, an entrepreneur husband who knew the grind that it took and watching him build his business was an incredible inspiration for me of what was possible. So I think your community and circle is a big one of having the right encouragement to make that decision as well. But make sure that you are outlining what those variables are for you. Is it financial? Is it an emotional pull? Is it something bigger for a longer-term vision that you have for you and your family? Whatever it is, try to think about what that criteria might look like and use that as your decision-making rather than just making a rash decision in the moment.

That makes sense. And then for someone who's in that place of building a business while they have young kids at home, which I have done, it's challenging. I may or may not have gotten shingles from stress, you know, doing that with two young kids. Any advice or things like, was there, you know, one or two things where you're like, oh, this actually got me the time and space to be able to work on this or the, the sanity or peace of mind to be able to do it?

Oh yeah, it's such a good question. I'd say in my particular case, and I hope this is, you know, a good guide for others listening, is try to compartmentalize what you can. Meaning, you know, for me, part of the joy of actually building the business, despite it being, you know, a lot of that grind at the beginning, was being able to be there for my family and my kids at that young age and actually absorbing those moments. And so I was I was very strict with myself around in these times of the day, like, it's not business focused, it's family first. But then I would also be very, very self-disciplined around as of these hours, like, that's mommy time. Like, I gotta do my thing. And I think as a parent, as you're building a business, it's actually really inspiring for your kids to see it because, you know, it ties a lot in the coaching that we do and what we talk about that there's so much we don't learn to really thrive in careers, whether as a creator, corporate professional, you know, whichever way you look at it. And so as we're raising children to see what careers can look like and seeing that drive in you as their, as their role model, that was something that really fueled me, that even if I was taking time at night, even if I had to take some time on the weekends, I was, I was showing them what it meant to build something great. And that really stuck.

Yeah, and I think letting your kids watch you pursue a dream is such a special thing. And then if there's any ways that you can include them in it is, it's just fantastic. And that comes as they get older, that sort of thing. But like my son and I this morning, uh, were sitting on the couch and I was showing him how to do some stuff in Figma, how to do basic design and that sort of thing.

I'm like, okay, this is fun, right? Cause he's at that age now where he's probably appreciating it a little bit more. And it's like, oh, this is really what daddy does, like in the day to day. That's amazing. But it really is about involving them. And I think that's the fun part with careers. Especially in the creator space, like anything is possible. Like you can do really what you want. And so to have that vision from your parents setting an example that doesn't feel as traditional, like what a cool time to be able to do that.

Yeah, I love it. Okay, so for the most part, when we look at a creator's business, we get to see the website and we get to see the posts that go out on social media. In both cases, I was going through yours in detail, right? The website's very polished. Oh, the, um, YouTube Shorts and all of those, right? They're very, very polished and all that. And that's what we see from the outside. And you've been so generous in this case to say like, yeah, absolutely. Like, I'll let you all come in behind the scenes into the business. So sort of work up from really over the last, I guess it'd be the last 4 years, right? That you've built the business.

Yeah. Entering year 5 now.

You've gone from no revenue in the business to $1.1 million last year.

Yeah.

That's, and to do that in 4 years is absolutely phenomenal.

Thank you.

Take us through that journey.

Yeah, it's been pretty wild. I mean, it started, uh, really from the ground up, from zero. I mean, as a creator, I, I didn't know anything about that space. Um, I was actually pretty private before starting a business, and I, I don't shy away from public speaking or, you know, presenting, but I think—

and you did a lot of that.

I did a lot of that in my work at L'Oréal. So I think that, that prepped me in like what that required of me, but it's still a really different ballgame.

Something that I've noticed is a lot of these creators who come out and have a lot of success quickly, right? Maybe an extreme example of this would be an Andrew Huberman.

Yes.

Right, who comes in and you're like, from no podcast to one of the most popular in a handful of years.

Yes.

But then you realize like, okay, extreme credibility coming into this and extreme expertise.

Yeah.

And a whole bunch of skills that really matter, right? And so in your case, It's not like, you know, you're the recent college grad or someone else, you know, you've no experience.

I want to build a coaching business.

You're not trying to, you don't have to learn tons and tons of skills.

Yeah.

Right? You have to learn a lot of creator-specific skills and a lot of business skills.

Yeah.

But you're like, oh, being on camera is not that different from the boardroom presentation.

Of course.

Or those things. And you're like, I already, I did my time learning that set of skills.

100%. Yeah, and I, I feel really lucky to have had such a strong business savviness coming out of L'Oréal and managing multimillion-dollar brands. Like, that prepped me well for that side. But to your point, I think the creator part of it, of what does it take, what does it take to build a content, you know, fueled business and build an audience, build a newsletter, like, and that's just been so much fun along the way. So I would say back in 2023, that was really the year that we broke through, uh, our 7-figure mark from a lifetime revenue standpoint. So the first 2 years were were the buildup, reaching, you know, multiple 7-figure— multiple 6 figures, I should say, in those first few years. And then 2023 was the year that really brought us over that point. And then last year, I'd say one of the big shifts that helped and was very much needed in the business was improving our operations to really scale further. And so that's when we brought in our COO, who had previously ran his own business sold his business. He had bootstrapped it from $50K to $75 million in 7 years with just 5 people across 5 continents. And so we were very fortunate to bring him on and just see the business from a different lens. I always kind of say it's moving away from like my coaching hat to the CEO hat and like, what does it really take to build the machine that builds the machine?

And if you were to break down like 2 columns What does the coach do and what does the CEO do? And like that, that, you know, what shifts did you have to make?

Yeah. Oh my gosh. How much time do we have?

Coach Tiffany would do one thing.

Yeah.

CEO Tiffany now approaches this a different way.

I'll give like a really concrete example. I think Coach Tiffany was all about like delivery, delivery, delivery of the client experience, which by the way is still extremely important for us. But now CEO Tiffany is is what can we do to elevate the experience? What team members do we need? How do we operationalize the delivery? How do we further build the retention of the business model? And so it's thinking a lot more strategically of the ways and strategies to get us there rather than feeling attached to the execution of it. And so I think that was a huge shift, whereas a lot less about me, now it's about the team and what we can do together to really build that. And then I think even just from like a content standpoint, you know, the coach, to the CEO is, and I think that's also one of the things I really loved about your episode with Ali that you guys really reinforced was, you know, it's not really just about you. Like, it's about you're, you're the guide, right? You're the one that's helping elevate the customers and they are the story. They are the ones that are really the heroes of it all. So that's been a big shift of really putting myself more on the back burner and allowing that to shine through. In building it. So a lot of shifts, I would say. I think another one is being much more operational in identifying where our biggest constraints are as a business. That's been a huge shift in putting on the CEO hat of not just doing what I want to do, but doing the hard things, making the hard calls, and identifying where our biggest roadblocks are and solving for those problems.

What's an example of one of those constraints that because you were stepping, you know, out of the business, like working on the business rather than in it, that you were— what's a constraint that you were able to find and then solve?

Yeah, I'd say probably a more recent constraint was on the delivery side of the business because again, having previously been the coach, there was a lot of my involvement in the client experience. And so building out our team over this last year and a half has been instrumental because now our clients come in for an amazing experience with us and it's not just about me, nor do I want it to be just about me. I want it to be about them and get them the resources that they require. So we've been very intentional about building an incredible team industry-first-led team with the practical guidance that is going to help them unlock that fullest potential, with one of our recent hires really being an incredible tech leader that's bringing a lot of amazing insights. So that was a huge constraint because for me to be able to do more of that CEO work, it can't be so attached to the direct delivery of our experience.

And then was there a particular tipping point or a breakthrough that happened to take you from the revenue that you did in 2023 up to 2024 where you're breaking $1.1 million?

Yeah, I would say like operationalizing it was a big one and also thinking longer term. I think when you kind of have that coach hat on and for any creator, you know, that is in a coaching business, it's easy to think very short term, you know, weeks, months, few short quarters. But I really challenge myself to think bigger picture of where do I want this to be in a year from now, 2 years from now, 5 years from now? And use that to reverse engineer back what changes need to happen. And so that tied a lot with some of the operational improvements that we made, the team building that we brought into it, and making sure that we are providing not just a best-in-class experience for our customer base, but really pouring into that community. And that goes back to those core pillars, right, from even building up our newsletter that we publish 2 times every week and just bring like immense practical value, or now shifting into more sides of the media with our video podcast and bringing more of that community and in-person experience. It's all really playing into that longer-term vision that I probably wouldn't have really been thinking about as actively if I just stayed kind of stuck in that, you know, multi-six-figure type of mindset as a, as a coach that was doing the same things over and over again.

So in And like, I'm trying to figure out what's different from that, you know, say $300,000 to $400,000 a year mindset and the, you know, the million scaling to $2 million and beyond mindset.

Yeah, I'd say the big one, Nathan, was really solving for my constraints, like proactively all the time.

So you're anticipating the constraints that are coming.

Anticipating and not shying away from it. I think the trap that I used to fall into, quite honestly, was I liked what I liked and I wanted to do more of that. And that was serving me to a degree, but it was probably holding us back in the growth that we could have. Whereas making that shift, especially back in like late 2023 and into 2024, I was like, I can't work like that anymore. We need to be a lot more problem solving and make sure that I'm identifying what those roadblocks are, identifying what these constraints are. And you know very well, I'm sure, and with the creators you speak with, once you solve one problem, another one new one comes up, and then it's like, okay, well, now let's solve for that. And then it's another problem. So I, I think just really building that muscle of being okay with that, and that the problems don't mean something bad about you as a founder or CEO, but it's— but what's doing best for the growth of the business has been a huge shift, like, very much mindset-wise, but also the way that it's translated in how we show up as a business.

Yeah, what popped into my head is Ryan Holiday's book The Obstacle Is the Way.

Yes, oh, I love that book. I love Ryan Holiday. I love Ryan Holiday, and that is an incredible book.

But just that thing of first being able, putting the systems together in your life so that you have time and space to even figure out what the obstacles are.

Yes.

And so that looks like setting aside one Friday afternoon a month where you go to your favorite coffee shop and there's no computer.

Yeah.

And you're just saying, okay, what are the problems? You know, and like, going to a different level.

Yeah.

And then the other thing that you mentioned is shying away from it. Like, I think mostly we go, when we see the obstacle, there's one lens of it where it's like, oh, there's a giant boulder in my path. Like, I'll figure out how to climb over and go around or whatever.

Yeah.

I think often we see it instead as like, oh no, there's a scary monster. Let's go the opposite direction.

Yeah. Because it's so easy, right? Like, it's, it feels hard and it is hard. Um, I'll like, I'll give a really quick example, you know, in our our business model, one of the constraints that we had also found was that the onboarding of our client experience wasn't optimal and that we could easily bring more value to our clients very early on in coming into our coaching membership by making some improvements directly in those first 30 days and how we ran that. And so we've been doing that now for several months and it's been like a game changer in their impression of their experience, the referrals that we've gotten from it, the renewals that we've gotten from it, just from improving those first 30 days in experience and really overdelivering. So prior, I was like, oh, you know what, onboarding is great. Like, no, it's perfect. We're getting them all set up. They're ready to go. And that just, you know, again, was one of those things that I had to be very critical with. And that ties back to that CEO mindset of, like, focus on the things that aren't working. It's great to, you know, recognize the things that are going well and continuing that, but don't shy away from the hard decisions that need to be made.

Yeah, I can give a very concrete example, uh, from my time building Kit is that we would talk a lot about the amazing team that we're recruiting and the, the, you know, we are hiring A-players and, and all of this stuff. And the reality is we weren't. We were in some cases, but the thing that I was shying away from, like the real obstacle where I'm like, no, that's a, that's a scary monster. I don't want to go there is real feedback and true performance conversations. And even when we would do those, then we would give so many chances. Like, oh, but this person is so invested in our mission. And like, it's easy to realize that, okay, I need to let someone go if they are not bought in or undermining the mission. And you're just like, why are you here? You know, or if they, you know, maybe they're bought in all of that, but they're just not trying. The hardest ones is when someone is bought in, they're trying really hard, and they're not able to, you know, even with the help and support and all that, they're not able to level up, you know, their team, their job, that sort of thing.

Oh, absolutely.

And so I, like, just shied away from that. And I let things go on for years that shouldn't have. And so that was the scary monster that I had to say, if I I'm going to be honest. If I'm saying I want this goal, you know, and I want to achieve this growth for Kit and this impact for our customers and all of that, then I have to actually upgrade certain roles. I have to have the hard conversations. I have to let people go that I really truly care about and I've worked with for years. And I need to go in and recruit replacements. And there's this quote that I absolutely love. And it's from Rudyard Kipling. And he says, you can have anything you want in life. And if you don't get it, it either means you didn't really want it or you tried to bargain over the price. And I was here saying, I really want this. I want to build a company that has massive impact. I want to get to $100 million a year in revenue. I want to do all of those things and I can do it in this way. And he's like, no, you're bargaining over the price. And so what ended up happening is because we had the necessary conversations, the performance plans, letting people go, putting in the hard work that sometimes takes 6 months or a year to replace some of these key roles. And we have recruited people that are absolutely phenomenal. And so those are the kind of things, like when I think of the difference between like operating as a coach or a designer or a leader in the business versus really taking a step back. Yeah, and saying, okay, what are the bottlenecks? What are the things that I'm scared of and avoiding?

Absolutely.

Like, that was a huge one for me.

I mean, well, kudos to you, because I, I, I know how hard that is. And it's— it almost is that, like, feedback is a gift. Like, as much as we sometimes shy away from it, it's doing them a service. Because if, if it wasn't ultimately the best for you, for them, it's probably the right thing in the long run. And it allows you to make space for the people who really can be at the level that you need them to be.

I want to get into really speaking to the, you know, the creator, the coach, the entrepreneur who's stuck at that, you know, $500,000, $700,000 level.

Sure.

And the breakthroughs that come, like what needs to change in order to get to that $1 million and beyond mark. But before we do that, I want to have a little bit better of a grasp of your business.

Sure.

Would you be up for breaking down like some of the core revenue streams and, you know, where income comes from.

Yeah, absolutely.

In your business.

Absolutely. So our primary revenue stream is from our coaching membership. We have our flagship product that's been there from the inception of the business, but we've definitely grown it over the years.

Like what's the price point and the packaging on that?

Absolutely, absolutely. So it's about $7,500 price point for about a 6-month membership. Okay. We do have renewals and alumni options that are quite popular, but the base is at the $7,500. Price point. We also, that's about, you know, 70% of our, our revenue coming in. I'm also a LinkedIn Learning instructor with over 900,000 learners. So we have some, you know, definitely royalty income coming in from that on a yearly basis. We do also have our B2B engagements as well. So as I was saying, that's much more of a bigger focus coming into this year, but prior in In last year, it was a smaller portion of the business. Uh, so that's definitely another anchor that, uh, that's been fueling the revenue. Yeah, yeah.

Okay, that helps a lot. And then the, the leads for the coaching business, right, for people who end up signing up, you know, for the flagship offering, uh, where are those primarily coming from?

So that's coming from a combination of my newsletter. Uh, we have a very engaged community. Uh, like I said, we publish our newsletter 2 times every week. Our our Peak Performers issue and then our Friday Inner Circle issue. So that's been just a great way of building trust and nurturing our audience there. We do also do live events every month, every several months.

Are those webinars and workshops?

So those are webinar and workshops format, and those have typically brought in anywhere from, you know, low 6 figures to multi-6 figures depending the type of focus that we have for each one. We try to switch it up, and this year of course, we're moving into in-person that we're, we're really excited about just to elevate that and bring a more immersive experience with industry leaders right there in that, that in-person setting. So that's been a huge driver for us as well. And then I would say there is the referral piece that plays into the balance. And I mean, when I say content, I think LinkedIn is also playing in because we've had quite a few that have found us specifically through my LinkedIn courses, whether promoted from their companies and they're like, I think you can help me, or other ways around. And now what's happening is also from the B2B approach where we are bringing immense value to the companies that we partner with, like Microsoft, and their employees are wanting more. And so whether we're either supporting them from a B2B standpoint or more on an individual standpoint.

Yeah.

So those are the 4 key ways I would say that they're, they're coming into our ecosystem. Them.

I like it. Okay, that's good context.

Okay.

So now let's speak to that, you know, stuck.

Yeah.

You maybe 3 years in a row.

I know that feeling.

$500,000, $600,000, you know, somewhere in that range. If you were talking to a coach who's in that position and they have this ambition to scale, because we can just name that if someone wants to run a $500,000 a year business and continue that, like, you've won. You're doing awesome.

Yeah, nothing to shy away from.

And this podcast is all about about like growth is for the people who have, yeah, uh, you know, wild ambition and all that. So of course, what are some of the questions that you would ask if you're helping someone figure out, you know, the key bottlenecks and how to get them unstuck?

Yeah, I would really try to identify with them what's bringing the most value in their business but what's also creating some risk for them.

Yeah.

So I, for me, that was an exercise that really helped me identify where our biggest constraints were. For instance, um, key man risk. Like I identified that in our business because we started it as a personal brand and very much knowing very well the coaching space. I'm in the career coaching space, but it extends across that. A lot of it can start that way. And so it becomes this balance of, is the key man risk where it's so attached to you actually helping or is it holding you back? Sometimes it could be either which way. In our case, I felt like it was a limitation that was preventing me from from initially having the team that I wanted or the structure and operations. So I would try to ask some guiding questions at the beginning around the types of risks. Is it around, you know, the key man risk?

Yeah, well, let's dive into key man risk for a second because creator businesses have inherently the most key man risk. So that basically what you're saying is that like for any Uh, what I would imagine is any top-of-funnel content requires you, the management of the business probably requires you, and then the delivery of the product, if it's a coaching product, yeah, requires you. Is that what you're experiencing?

Pretty much. And I think like a very tactical shift, just for our listeners, was, you know, a lot of my content prior was about me and like the story of me and the growth that I had in my corporate career and how you can achieve the same and how, you know, we'll help you do that. And I got to the point where I was like, no, it has to be about the stories of those that we've supported.

It's that hero versus guide shift.

100%, 100%. And so that was like one of a very tactical shift, like in the day-to-day that moved away from that key man risk. But I think also just in the way that we speak about our business, you know, It's a we, it's the team, it's our team of experts. And I think as any creator or coach even that's looking to build their business and really scale beyond the $500K mark, it's about looking at the team that you have and really shining the light on them and showing that there is a team behind this. I know that's something that our clients have really appreciated, that yes, I'm still there, I'm still, you know, making sure it's at the standard and quality that I hold us to, but there's trust in the experts that we have and the team that we have because it's vetted through the personal brand, right? And so there's ways that it ties together, but it's an interesting way to think about it so that the dependence is reduced on you and that key man risk, but also very tactically in the day-to-day of how that comes to life because you'll still be doing a lot of the content, especially if you're a video content creator. I mean, I still do my video content. It has to be my face. So that's one thing. I think it's what builds that trust and authority and credibility, but then it's finding other ways of offsetting that so there's a nice balance. And I think that's been a key shift. So that's one of the areas I would definitely look at with a creator at that point of seeing what are their goals, what are those aspirations, and really trying to identify where those, those risks are, but also what's bringing a lot of value for their business and trying to pour more fuel onto that because sometimes Sometimes it's not as complicated. It's just doing something even better than what you're already doing right now.

One thing that I could see a lot of people saying or thinking right now as they're listening is like, but it's a coaching business. I have to be the one delivering the coaching and the product that we ultimately sell. So how do you go about bringing in, you know, other facilitators and coaches and going from, you know, a single brand to, you know, to a team without making it feel like you're settling or devaluing the product or something like that?

Yeah, it's such a good question, Nathan. I think that's a very common limiting belief, I would say, as a coach-led business. And it's one I honestly thought for quite a while. Like that first 2, 2 and a half years, I was like, no, it has to, like, I have to be the one. People trust me. Like, it's based off of, you know, the story that got me into this business. And so it was really this like tug and pull of how do I make that shift? But then you really kind of come to realize that if you are building the team that is, of course, inspired by your mission and is living and breathing your mission and executes on that mission, there's no devaluation because now you are doing what you need as a CEO to build the arsenal, to build the experts around you who are going to deliver an amazing experience. And so that's how we frame it. And it's something that's been very well receive that we want you to have all the support to reach that target outcome, whatever that is for you, right? And so if it's just me, yes, we'll get you to a certain degree, but I want you to have a multitude of perspective, and I want you to have designated individuals who can help you in these very targeted pain points and challenges in a very practical way. Because again, it always comes back to us for that practical guidance to unlock their fullest potential. So I think that's an interesting way way for creators to start thinking about it, that it's actually a bigger value add when you see what are those missing links that can actually elevate the experience and perception from, from possible prospects and clients as opposed to something that will actually devalue the business.

Yeah, that's something that I've thought a lot about at Kit is where, you know, if I'm talking to someone who wants to join the platform, maybe they're someone who's really influential, like an author who's sold millions of copies of their book or something like that. I need it to feel like when I talk to them, you know, and when I hand them off and introduce them to someone on our team who's way more capable at like bringing their newsletter to life and doing the migration, all that, it has to feel like, has to feel like an upgrade. It has to feel like they're not like, oh, well, Ethan doesn't have time for me, so he just dumped me off on someone else. And so some little things that we've done, is one, hire amazing people and, you know, retain them for a long time. Like that's, we have a very long tenure in our company, but every chance we get, we elevate the team members and their expertise. So deliverability is like this very niche topic in the email marketing space. And two of our team members who run our deliverability department, they have a podcast called Deliverability Defined. Where it's now the industry-leading podcast in this small niche.

Amazing.

Where they're talking about it and all of that. And so anytime I'm introducing to either Alyssa or Melissa, it's ironic that—

that's a good tag too, right?

The alliteration they have in their names. Um, but you know, I'm saying like I might link to a podcast episode where they talk about the topic that this creator is dealing with.

Absolutely.

And it's like, oh wow. Well, I mean, you could talk to me about it, but why would you do that when you could talk to the industry experts on it? Or another example is we launched this newsletter for Lil Jon recently. He had, it's called Wellness Wednesdays and it's, you wouldn't expect this. I was surprised. I was like, oh, Lil Jon wants to launch a newsletter on Kit. That's amazing. What's it about? And they're like, wellness and meditation.

And I was like, oh, unexpected twist.

Unexpected. All right, I'm in for it. But Morgan, who's on our creator growth team, who really did all the work behind the scenes to bring this to life. When we did a launch video, it's her here in Kit Studios talking about, you know, here's how we brought it to life. Here's the work that happened behind the scenes and all of that. And so when we put that live, it's not me as a CEO being like, look, we got famous creator.

Yeah.

It's, you know, really the team that did the work. And so now, when I have another famous creator that I'm working with and I'm introducing them to Morgan, I'm saying, oh yeah, she's the one who launched Lil Jon's newsletter. And I'm linking to that Instagram reel that Lil Jon has also shared to his million followers. Right. And it's, it's transferring all of this credibility and expertise to Morgan, which is 100% deserved. And then it starts off on a great foot because then someone's like, oh wow, I got, you know, I'm getting help from someone who's truly amazing at this.

Yeah, I love that. And it just goes back to So, you know, bringing that all together, it's such an important piece of recognizing and edifying the team, you know, because you're building a team of great people. And so, by just having your endorsement of them and then having these assets, like we do the same with our team because, again, it's industry-first expertise. So, they're from the Fortune 500 space, the Fortune 100 space, the Fortune 5 space. And so, when you're coming in, having access to these people, You know, it's almost like it makes the job a lot easier because as the CEO, you can choose who those people are. You could be selective and make sure it is the right people in the right seats as opposed to just having a team for the sake of the team. So I think as a creator's thinking about that and building out what those other resources are, whether they're people resources or something else, it's actually about really edifying the right people and making sure that their story plays into the mission of what you're delivering. That just makes it so much easier.

Yeah, that makes sense. At this creator level, right, we're talking, you know, hundreds of thousands into the millions and all of that. Like the conversation is really a lot about team and culture and systems and, and all of those things. But you said limiting beliefs earlier, which I think is such a key topic.

Yeah.

Were there other limiting beliefs that you had that you had to overcome in this, you know, breakthrough beyond a million?

Yeah. I mean, for me, I think it was, Yes, the key man risk was probably the biggest one. And then I think also around bridging out into other paths for growth for the business. I felt like because for such a long time it was really founded on coaching and the coaching membership as our key driver, that I didn't put enough emphasis on some of the other areas that I think I knew deep down, like, could work and work really well. But I worried that it would distract when in reality it's actually all about about creating that kind of flywheel effect. And so that was a limiting belief I initially had at that breaking point around, oh no, actually this is something that is going to help. I have to see it as part of our longer-term vision, as a catalyst, as opposed to something that would be any type of setback. And so that was definitely something that had to work through a little bit, um, but I'm really glad that I did because it's, it's just served us quite well.

Yeah, that makes sense. Okay, so you said flywheel again. So let's go back to the B2B pillar of your business. Sure. Because that's, you said that that could really, you know, you're seeing it grow into the flywheel that drives the whole business.

Yeah.

So how is that flywheel, how does it play out? Like what are the steps of the flywheel?

So, you know, for a long time in our business, we've, as you were asking before around how we get, you know, our clients and people coming into our ecosystem, webinars, workshops has been a big driver. Driver for us. And what we've seen with some of the B2B work that we're doing is it's almost like webinars and workshops, but directly, like, with a full audience of people that are our people, that the ones that we want to serve. And so it's been really interesting to see how that can actually bring us a different area of exposure, whether again, if it ends up being a B2B type of engagement that we're happy to support on and have a longer-term stint there, or simply give exposure to people who might not even have known who we were before, and then have them come into our ecosystem. Either which way, it's giving us those options that prior had not been a huge focus for us. So that is really a great kind of exposure and lead generation that we're really trying to pour more, more energy into.

Okay, so if you wanted to make that flywheel spin faster, yeah, what's the activity that you have to do?

So we're doing a lot more outreach. We are leveraging more direct outreach for leaders, you know, getting those connections going. Relationship building has been a big strength of mine over the years, even in my own corporate career. So we've leveraged a lot of our own network that we have and just using that and the brand. And so this is where, like, the key man does come in handy because it brings more credibility to form those connections with industry leaders, from major organizations, and we love offering, you know, an option to train their teams, sometimes even as an option to get in there without necessarily an initial investment and kind of build a relationship from there based off of trust and credibility.

Yeah, and one thing as you're doing, you know, outbound sales and that outreach, I find the media portion of the business, if we go to that other pillar, makes a huge difference.

Huge difference.

Someone's like, I don't know, are they relevant? Click through. Oh, okay, this is polished. They know what they're talking about. This is a real brand. Oh wow, they work with Microsoft. You know, like there's all these things that come through and like media makes a huge, huge difference.

Yeah, so that, that's a big part of it as well for us, which we believe is going to help really solidify that authority and create more of that visibility too in a way that will get on their radar. So it's all kind of tying in together that that we believe is going to help fuel that even more for us.

Yeah.

Yeah.

Something else I've seen this breakthrough to a million, um, I've never run a coaching business at scale, but, you know, if I have run a SaaS company at scale in the software industry, the biggest thing to be able to break through a million dollars in annual recurring revenue is you have to fix your retention. Churn matters so much.

Oh yeah.

You have this leaky bucket and all these people coming in and they're just churning out, that is a huge problem.

Yeah.

And so is that true as well in the coaching world?

100%, Nathan. You know, we talk about leaky buckets often, and that was actually one of the leaky buckets we had recognized back in like late 2023. And especially before we brought on our COO, that it felt like we were like chasing a lot, like constantly going after new, like constantly having to do workshops, constantly having to do all these things to bring new people. Whereas, you know, we had a better job to do of retaining the ones that we had and bringing more recurring value for them to make them want to stick around.

Right, to renew.

Yeah, and so some of the key shifts that we've done following that turning point was kind of both on the front end, midway, and back end of the experience. So I talked a little bit about the onboarding, which has already set a really good tone for us of bringing more value right up front, helping them get amazing wins, building that confidence, and making them more inclined to stay on and continue to continue with us, but then also on the back end of having really viable, exciting options for continuing and building more alumni types of offerings that would actually bring the value, not just have something for the sake of it. And I think that a good way for creators to think about this, at least this is how we've thought about it in our space specifically, the way that we're serving our clients is, you know, you evolve, your career evolves. An, an always-on type of engine, right? So it's not the type of thing that you need support on once and then good luck, you're on your own. We want to be that resource, that authority, that support for them at every phase that they're navigating. And so part of that's been a shift in our marketing and our strategy so that they recognize that. But that's also gone really hand in hand with the, the options that we provide to be able to continue. So I would say that And that's been a pretty strategic shift around not just focusing on the now and the short term in that client experience, but what can that look like longer term for them and for you as a business? And so that's been helping very much so in the retention, avoiding that leaky bucket, and not feeling like you're constantly having to go after new, but actually building on what you have already.

Yeah, that makes a lot of sense. I think there's also business models or niches that you can choose that have of like automatic churn built in. So I was talking to a software company a few months ago where they're amazing for creating these detailed reports and all of that, but it's something that you do like once every couple of years.

Oh gosh, okay.

And so people continually sign up, do the activity, and then use it for a few months and then cancel.

Oh no.

Even though they achieved remarkable success, like check, Did it meet your needs and goals? Oh, 100%, it was killer. And why'd you cancel? Because I don't need it anymore. And then they'll come back a couple years later when they need to do that again. And I would imagine there's businesses very adjacent to yours, like job seeking, right? Transformation that you're trying to create in that world is you're like, hey, I'm going to help you get your dream job and coach you to that point. Well, that transformation, amazing that you achieved, it, but it has built-in churn of like, thank you so much.

See you next time. Success.

Like, see you in 5 years, but hopefully never because maybe I'll be at this company forever.

Yeah.

And so, how do you think about that of building a business that can transcend the particular transformation? Because you're also not in the business of like, well, we want to help them mostly, but not fully. So they always, right? Right, like, no, we're trying to create the transformation, but we want to be able to keep them as a long-term client.

Yeah, 100%. I think what's been interesting, and you could kind of look at the business in two different ways— I'm speaking just generally in terms of creator business or coaching business— is kind of solving for pain but also solving for possibility. And we kind of have this nice balance, I would say, in the way that we structure it, where there's the pain of the immediate opportunity that they need in terms of their growth growth, feeling stuck, feeling like they need to get out of their workplace, whatever it is, and supporting them in that transitional moment of finding something new. But then the possibility is where, when you learn the right skills in a workplace to thrive, that's what creates the corporate flywheel or the career flywheel in that kind of setting. And so we focus actually a lot more energy there because that's what's bringing the true confidence, fulfillment, and happiness. And so I think, you know, as a business owner, as a creator, if you look at your business in a similar way of maybe what's that kind of immediate need that definitely will bring them in and support them, but how can you actually see a few steps ahead or maybe several steps ahead around what does that journey look like and how can you continue to support them? Because if you do have a business that's really kind of like churn is baked into it, like job searching, yeah, like once they have their job, they're not going to see the need for it anymore. And that's okay if you're okay with that as a business owner and you're all right with that. That approach, that's fine. We've just always thought of it very differently. And I think that served us well in having a fairly high retention rate and renewal rate and referral rate from our members.

Yeah, that makes a lot of sense. Are there other business models or other topics in coaching that you've seen that have that built-in churn where if a, if a coach is stuck, you might be like, hey, if you're in this industry, then yeah, you're going to have to to totally overcome that.

I mean, I would say, Nathan, anything tied with kind of like one-off services. So I'll use job searching as like an example, right? Like, you know, if it's a resume service or an interview prep service or whatnot, it's, it's very poignant. It's very much like a need I have right now, but it's kind of missing some of the bigger picture of the what, what follows that, what comes after that. And so I think even from other types of business models, if you're solving for a very situational-based need or something that is very much immediate, that can run the risk of falling into that trap of automatic churn. Because again, it just comes back to that recurring value. If they're not going to see a recurring value of what they can get from you, they'll probably find someone else who can give that recurring value for that phase of their life or career or whatever it might be, right? I mean, if we think of, you know, exercise, Right, like our fitness coach as an example. If you're helping someone to build the right type of exercise regimen, that's great, but there's probably other things. What about the nutrition? What about keeping good habits? What about having dedicated ongoing accountability? So if you're intentionally planning for what that cycle looks like and building out a plan that will support them in that, they're going to see the value, but it doesn't happen by accident.

Now, another big topic is operations and systems. And we can't talk about systems and operations in 2025 without talking about AI.

Oh, yeah. Dumb, dumb, dumb. Yeah.

So, all right. I was just thinking a quick aside. I went to— I was in Thailand a few weeks ago and the thing about the elephant in the room.

Yes.

And we went and did this elephant excursion. Where you got— it was at this sanctuary where they really raise and care for these elephants and particularly working with breeds of elephants that are going extinct if they're not, you know, really cared for and all that. And we were listening to this, they were explaining things to us and they called an elephant over because the elephants are insanely smart. So they call the elephant over and it like comes into the little canopy area that we were talking And the guy in his broken, you know, English Karen that he's speaking, he's like, "The elephant?" And we're like, "What?" And he goes, "The elephant in the room." And we're like, "Oh, he's joking. The elephant is in the room." So in this case, the elephant in the room is AI. And so what are you seeing in the industry as, you know, AI plays a big role in the coaching world?

Oh my gosh. I mean, it's huge. It's having a real impact on career years, most definitely, um, across industries. And it's so funny you say it because I was just reading an article yesterday that came out, uh, featuring David Solomon, the CEO of Goldman Sachs, and he was saying that now 95% of their IPO prospectus are being written within minutes from AI agents, whereas prior—

yeah, we were probably spending hundreds and hundreds of hours.

Oh yeah, amongst 5 to 6 team members per, right? And weeks, weeks of work. And so— Right.

This is an industry where it's like you say weeks of work and they mean 100 hours a week per person. Exactly.

They work in weeks, not hours. But yeah, 100%. But, you know, all that said, what was really interesting from the article is he emphasized that that 5% is really what still matters. It's that human expertise because everything else, in his words, is, you know, has become a commodity. And I love that. It resonated so much because when we think about our business specifically, that 5% is exactly who we're serving, right? It's the people who are bringing that expertise, who are elevating not just their own development, but the value they bring for their organizations and are really instrumental in that. And so much so that we've been really proactive around bringing in AI concepts into our business model. We've actually just recruited recently our newest team member, who is also one of our co-coaches now, and she is a former VP and leader at a Fortune 5 company.

So, uh, so we can guess which is it.

Yeah, I mean, uh, let's just say it's a pretty recognized household name globally. We're so, we're so happy to have her, and she is an amazing leader when it comes to AI and tech. And so a lot of our goal in bringing that on and having her expertise is not just from her lived experience, and again, always coming back to that practical guidance, but how you can really use AI in your career to elevate it and amplify it, not detract from it or or be seen as something to fear. And I think as creators, it's such a fun way to think about it too, of how do we bring AI into our businesses so that not just from, like, an operational standpoint, but how we can use it to elevate a lot of the things that we do or improve the community or to build an even better best-in-class customer or client experience, whatever it is. So we've been very intentional about that. And I'm excited about where that goes because it is something we need to embrace. Like, it's clearly not going anywhere. It's the news coming out every day. It's hard to keep up with almost. But those are definitely some key shifts that we're seeing.

So I want you to share one specific example, like as tactical as possible, that another coach could clone into their business of how you're using AI. And while you're thinking about that, the thing that I've noticed is along the lines of what the CEO of Goldman Sachs was saying, is that it elevates everything you're doing. It lets you do the most important work, right? So people are seeing, you know, someone building an app, using Cursor to code an app and do it so quickly and all of that. And it's like, and they're saying, oh, this will replace developers. And I'm like, it's not going to replace great developers. It's going to make it so that great developers are spending their time on like, how do I build something that really scales and doesn't have security vulnerabilities and all of this, or like it's going to elevate the jobs of someone who's great at copywriting, user experience, and bringing something really compelling together. Because it's going to say, it's going to force you to focus on the most important 5%.

Oh, that's absolutely, I love that way of thinking of it because we're taking a similar approach as well where very tactically it's about finding those time gains in many ways in, in the work that you're doing for our clients or, or any, customer, right? Where are those efficiencies that you can gain that it can actually help get more out of what you're already doing? Whether that is improving, you know, a report or helping optimize some of the follow-ups that we do as a business, you know, automating a lot of that and still having that level of personalization, but faster speed to get it out or to support our clients in that way versus having it be more manual. So there's just that fine balance that we're really working into both the operations of delivery, but also in the ways that very tactically our members can use that in their day-to-day work and shine, like really shine and impress their leaders in how they're using it and not like shy away and say, I haven't used it, but showing how you're using it and why that's actually helping you perform even better in that top percent bucket.

Yeah, I love it. So what's something that, you know, a workflow or a system that you're using in AI that another coach could clone into their business?

Yeah, for us, it's a lot of our lead follow-up is something that we're leveraging it for right now. So something in terms of both categorizing our leads and having more types of flows around which leads are falling into which bucket, which prospects are most likely to likely convert into our membership. What are the cues that we're picking up from the answers that they might share in initial questionnaire? What are the trends that we've seen from past customer and client data to identify those patterns and then help us fuel that automation so that it can really recognize that much more proactively. So that's one concrete thing that we're definitely working through in our lead generation flow and follow-up strategy.

Yeah, I love it. Are there any specific tools that you're using to implement that?

Uh, we're using part ChatGPT in terms of seeing both NotebookLM and ChatGPT have been pretty good instrumental tools for us right now. We've used a bit of code as well. Notion is one of the softwares that we'll use in part for that, but we also love integrating even more automations with what we're seeing with Kit too and just inspiring that for a lot of our segmenting and filtering there from our community that we've built because it's one of our largest communities right within our Kit community.

I love it.

Yeah.

There's a tool called Lindy.ai.

Yeah, we just started checking that out actually.

It's a lot of fun. You can put together these workflows. That follows and says when this happens, you can have it make phone calls for you.

Yeah, I know.

It's wild.

We were just talking about that, me and my COO, last week actually. And we were saying the same thing. I'm like, yes, we need to look into that and see how we can bake that into.

Yeah, I love it. Well, I'm blown away with what you've done with your business to scale to the level that you have as fast as you have. And I think just looking back at those breakthrough moments, right? We're talking about limiting beliefs. Yeah, talking about building the systems and operations, right? Like leveling up the team, all of these things. Oh, and retention. Like retention is such an important thing.

It's a big one.

And you have to look at, are there systemic reasons for the churn in your business? And those things matter so much. So thank you so much for coming on. Where should people go to follow your content and follow the rest of your journey?

Oh, thanks for having me, Nathan. This is so much fun. Uh, definitely I would love to connect with our listeners who checked out today's episode. You can follow me right on LinkedIn, send me a DM, uh, let me know that you've checked out this episode, what some of your takeaways were. Just Tiffany Uman, easy to find, it's the only one. Um, you could also check out my website, TiffanyUman.com, if you'd like, and on socials, Tiffany.Uman.

Sounds good. Thanks for coming on.

Thank you so much.

If you enjoyed this episode, go to YouTube and search The Nathan Barry Show, then hit subscribe subscribe and 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 just who else you think we should have on the show. Thank you so much for listening.