136: Why I Stopped Exploring Selling the Pivot Brand and Business

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The more saleable you make the business, the more you're the one that wants to keep running it because all of a sudden it's even leaner, even meaner, even more profitable. So at that point it's not as clear of a decision. Once you optimize everything you would need to optimize to make it attractive to a buyer, that buyer might be you.

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In the spirit of truth. Walt's Fresh. This is a truth that I would say has been on a low simmer, but one that I've not shared too much on this podcast and that is my process of exploring potentially selling the pivot side of my brand and that part of my business and why I stopped exploring a potential sale of that part of the business. I talked about this a little bit in episode 93, how to sell your online business with my friend Lexi Grant and I shared more in episode 276 of the Pivot podcast. I did an episode called behind the Free Time Pivot where I talk about turning my attentions to this new direction and I still have both. Like right now. These are the two skis of my business. They are the two big umbrella brands. I now describe myself as running a small media company, an IP licensing business because it has become a bonafide media company with two podcasts, two newsletters, IP that I license to companies. That's really the way I'm describing what I do right now. There was a time as I was thinking about going all in on free time that I wondered if I should sell the pivot side of the business. That's what I'm going to break down today and this is really just sharing my thought process. I have no expertise in this area. I clearly didn't sell it. So this isn't one of those. How I landed a mega million dollar exit is really just sharing the research that I did, the pros, cons and considerations, and why I stopped pursuing that path at all. I also feel the need to preface this episode by saying this may be a complete result of my own personal shortcomings and the shortcomings of my business. So if somebody were to come out of the woodwork tomorrow and offer me $5 million or $10 million, you think I would sell that part of the business? I would very much be thinking about it, let me tell you. And so I'm aware that there was a gap as well. It was really more of a curiosity. I was completely 50, 50. I just started to open myself up to the possibility of what would it look like if I were to sell that part of the business and bring in a new operator and a new operating team. And I'll tell you more about why I was even thinking that in the first place. So part of it is that there was this gap between the readiness of that part of the business and what I could sell it for to yield a good enough offer from someone. So the fact that I stopped exploring that option is also partly because it wasn't really a viable option. That's important for me to say that if it was this gangbuster potential sale, we might be in a different position right now. We might be having a different conversation. I guess it just feels important to acknowledge completely my own shortcomings and the business's shortcomings as why I didn't keep going down that route. Even there, you could say, well, you could address those shortcomings. That as well would take energy and focus. And there are reasons that I decided not to pursue even the path toward improving the whole saleability of it. At the start of 2021, I did a lot of thinking, as you know, because we were all doing a lot of deep thinking in 2020 for me, thinking about the Pivot side of the business started a few years prior. I am really proud of everything I built with the Pivot brand and book. You've heard me say it so many times. But just to give you the timeline, I wrote the very first version of the proposal for Pivot in 2013, landed the book deal in 2014. Pivot the book came out at the end of 2016, September 6, 2016 to be exact. Just a month prior to that big old presidential election, Pivot and the Pivot podcast came out a Year prior to that, in 2015. So the podcast has been around over seven years. The book has been out for nearly as many. And the whole way through that, I was writing the book that I knew the pub date. I was building scalable streams of income to support it. I had read the book Build to Sell by John Warlow. I loved it, and I really wanted Pivot to be a viable, sustainable, scalable business. Even with my delightfully tiny team set up, I am so proud of what that book accomplished. It won an Axiom Best Business Book award in the careers category. Google started licensing the material. Other companies as well started licensing or exploring it. The podcast was doing well, was not a gangbuster show, but it was making me a lot of friends. And we had a solid, steady base of listeners. The newsletter had grown to about 20,000. You know, none of these numbers, even the book sales, they were not grand slams, but the book sales are probably in the top 1% of book sales for any given book. So it did very, very well. And as you know, Pivot as in terms of a career, Pivot started to really become mainstream. It was in the zeitgeist in 2020. We were all talking about pivots left and right. It was the de facto word of the year. Something happened at the end of 2018 that kind of shook me up a little bit, and that was the launch of the other Pivot podcast with Kara Swisher and Scott Galloway. I don't know why I found it, but I discovered a trademark for the word Pivot as a podcast that had been filed. And I don't know what it, in my intuitive sense had me even go look that up, but I saw that they had filed a trademark. And this new show of theirs was getting all this momentum and funding and traction, New York Magazine and Vox Media, and they were throwing all this ad money. And I listen, I have listened and subscribed since that podcast launched, so I have no ill will or anything, but it felt like I had been playing in this sandbox. Maybe I didn't take it seriously enough to the point where this new big brand of the same name comes in. And I started to feel like these big players came to my same sandbox. I also started to feel a little wary or almost embarrassed if I would introduce myself as the host of the Pivot podcast, because all of a sudden there was confusion. Which one? The one that inevitably the person I was talking to actually listened to with Kara and Scott or with mine that had a much smaller listener base. Normally that one thing Alone would not get me to Pivot. See what I did there to change my own direction. Of course I'm not going to blow around like a leaf in the wind. At the same time, when things like that happen, I do take it as a signal to pause and reflect and really consider. Do I still want to double down on this area or is this an opportunity for me to start considering other moves? But the much, much bigger impetus that had me researching what it might look like to have other leadership organizing structures was a result of its success. By the time 2020 hit, I had fully built out the Pivot part of the business. There was the book, the podcast, the newsletter, the licensing. I even had trained facilitators under me within my own business. Under is not really my favorite word, but I had trained people to facilitate Pivot keynotes so that I wasn't even the only one. I had a team of Pivot coaches within companies. I was doing train the trainer. I had all the materials, I had all the scalability in place and I even had a few LinkedIn learning courses that were uber scalable. So any company with a LinkedIn learning license can take one of now five pivot related courses. One of them even got featured on the back of the airplane in the Delta interface, which is really a cool moment. At that point, what Pivot needed was not more creation, more launches, it needed a growth strategy. And that's where I started to feel the ceiling. I felt myself bumping up against this complete ceiling and a wall of resistance that I am really an idea person. I'll put the link in the show Notes to a conversation I recently had with my friend Jonathan Fields for his session Sparked podcast that's part of the LinkedIn network that I've been thinking a lot lately about three types of people. Builders, maintainers and optimizers. If you're a builder, you love taking things from 0 to 1, creating order from chaos, new ideas, trend spotting, harnessing things and then creating something new. Maintainers are really good at maintaining and even growing an existing program or set of ideas. And then optimizers are really good at coming in and seeing something that already exists and optimizing how it's done, creating more efficiency, improving systems, process automation, all that good stuff. The example I gave in that episode was that when I helped co create this drop in coaching program at Google Career Guru, I loved building it. I loved taking it from 0 to 1. But then still as part of my role was now how do you get people to sign up? There wasn't any Awareness of the program. And so my role within Career Guru shifted from co creating it, branding it, launching it, working out all the bugs and kinks of the early people signing up, training the coaches of how to conduct these drop in coaching sessions. The work shifted from all that to marketing. So even when I was in a company, marketing was my Achilles heel. Now it's not about building, it's about spreading the word, creating partnerships, tacking it on at the end of L and D programs, trainings, onboardings, new manager training, marketing, marketing. Marketing is all about communications growth. How do we grow the numbers, how do we increase traction, how do we get the metrics to show more and more people signing up for these sessions and that the sessions are going well. And that just was not my strength. Maintaining, optimizing, yes, I could make the case for that. But part of me just feels complete. I feel complete and I feel ready to move on. Same thing happened with life After College. That was my very first website. I set it up in 2005, started blogging. Seven book came out in 11. But I was done by the time the book came out. I had been talking about life after college for six years. I was ready to pivot. I was ready for something new. I didn't want to talk to college grads for the next 30 years. And I knew I had examples of people around me that did that and had very successful careers doing that. You become the after college person. And for many years in the online world, podcasts weren't even around then when that book was coming out. Not in the same way they are now. I was the life after college person, or some people call me the Google person or the life after Google person. And it took time, it took work to shift my own identity, to even figure out what the heck was next, if not life after college. But I just knew that I could not, did not want to talk about that the next 30 years. I was much more intentional when it came to building pivot because I knew that pivot was about change. And that if there was one thing I could guarantee that I would always be engaged in, that I could reliably talk about for a long, long time was pivoting change. Of course, the word now sometimes the word people cringe cause it's just so overused. But that's what happens. That's what happens if you spot a trend, you're early and then all of a sudden it's ubiquitous and people say, oh, that word. It's so played out. I get it, I get it. Because pivot resonated so deeply and so well aligned with a growing trend and then a massive mega trend wave hitting of the pandemic which none of us could have planned for. Of course no one would wish that upon anyone or any of us again. But it happened and it succeeded.

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So as we turn the corner at the end of 2020, I became clear that with a lot of my speaking gigs and client work dissipating in 2020, I had the confidence to try to go all in on a new direction of ip, a new book, a new brand, a new podcast. I share more about that exact decision and the courage giving myself permission to move in this direction, where I'm speaking more directly to small business owners in episode one of this podcast. So you can go back and listen to episode one if you want. Suffice it to say that my energy was so strong for this new direction of free time that I didn't know what to do with the Pivot side. Because Pivot had succeeded and I had succeeded in building a very scalable model for how it could grow. But what it needed from me was then to go seek more clients to build a better process of landing new big corporate clients, landing the next five licensing clients, or the next 15, the next 25, however much it was going to grow. And I didn't have that energy in me. I didn't have an ounce of feeling in my body that I could do a bunch of sales calls, that I wanted to do outbound sales at all, that I even wanted to Onboard five more licensing clients. Don't get me wrong, if they knocked at my door tomorrow, you know, I would. But I was feeling really conflicted that I felt the timing, that this new direction, that's where my energy needed to go. And I'm very, very intuitive about how I run my business. That's why sometimes I joke that it's a hobby, because you cannot always point to strategy on paper. For me, like my books, my big ideas, it is just often comes from instinct and intuition, yes, that I train and hone as well by all the content that I read and curate. But I felt bad. I started to feel bad. I have this beautiful product and brand and book, and I had started creating the moat around that IP because it had taken off. It did get traction, all of it. It was succeeding. So it was all there. It was ready for growth now. It needed somebody who wanted to grow it and who wanted to scale it. Part of me was just thinking, you know, what is in the best interest of this IP itself? Not even just me, but do I want Pivot to reach further and more people? Of course I did. And there was a big part of me that felt like it had so much potential to do that. That is what got me to start at least exploring the idea. What would it look like? I felt that I had, let's say, four options. Option one, do nothing. Let it carry on in a steady state. I was a little nervous about that because maybe that would dilute my focus too much. Trying to chase two rabbits, as the saying goes. As I even said to you at the start of this episode, it's as if I'm standing on two skis right now. Skiing is super fun, but when you start going too fast, your skis can get tangled up. And one leg twists one way, the other one goes the other way. It's a little trickier than having one snowboard that's taking you downhill. Is it, though? See, I could make the case either way. Option two, I could shut it down. I could just say, if I don't want to do it, no one's going to do it. And I could have even changed the Pivot podcast feed into free time and just hope for the best. Even though not all Pivoters are technically free timers. Yes, there's a lot of overlap, but free time? I'm speaking directly to business owners, and not all Pivoters care or want to run their own business or have a side hustle where a lot of this content is relevant. Even though I think they could find ways they'd have to kind of shift what I'm saying to apply their situation. So I could have just shut it down and say, all right, I'm done here, close up shop. But the thing is, I'd already built it and it was largely passive and scalable, already running. So I definitely didn't want to just shut it down. That did not seem to make sense. Option three, I could bring in a CEO or president. In episode 51 of this podcast, I interview Michael Bungay Stanier, who did exactly that. For two years, he trained and transitioned Box of Crayons, the company he built for two decades, over to Shannon Minifi, who took over as CEO. And in episode 115, I interviewed Shannon about her side of that experience and what it's like carrying the company forward today. So, you know, I'll put all these links in the show notes. That was option three. Trying to find the right person, bringing them in, training them, and then staying tangentially involved, but not hovering or micromanaging. And that felt like a big hill to climb. Finding the right person, training them, trusting them, structuring it, and then trusting that I could either not be involved or that I could have the energy to be involved at whatever capacity they would even want. It just felt like years of work. Option four was, did I have something valuable here that someone would want to buy? I heard Andrew Wilkinson, who is this brilliant guy, he founded a company called Tiny. You can visit their website@tinycapital.com. i had heard him on a bunch of podcasts and I loved his philosophy. I loved how they were buying and selling, mostly buying, acquiring tiny businesses. When I saw that they had acquired a brand called GirlBoss, many of you will be familiar. This was a best selling book by Sophia Amoroso that then she turned into an entire platform and business. Now, she had gotten venture funding for that business for Girlboss early on, and she has shared an interview she's done of the ups and downs and trials and tribulations of getting venture funding at all. I think now she doesn't have venture funding for her New Direction business class because of how complicated it made things that changed hands several times. So I believe that she had one exit. Another company, interim company, purchased it and then Tiny purchased it from that interim company. But I kind of looked at Girlboss and I thought, okay, it's similar. There's a book, there's a brand, there's a podcast, and there's potential for a platform, whether it's in the case of Pivot, could be a job board, job exchange. It had all the IP and the brand differentiation going for it. When Tiny acquired Girlbras, they replaced the podcast host, so it was no longer Sophia, it was someone new. There's always risk when you do things like this, but. But clearly they were willing to carry the torch forward into the next phase of that brand and that platform. And that allows someone like Sophia to step aside, do her next thing, but ensure that Girlboss doesn't disappear entirely. So, as remote a possibility as it seemed, that's what had me at least binge a bunch of Andrew Wilkinson interviews. Funny story about that in a second. And then I also started reading tons of books because so many books and podcasts talk about starting a business and so few talk about exiting them. I binged a bunch of episodes of John Warrilow's Built to Sell Radio. I read books like the Automatic Customer that he wrote. He also wrote the Art of Selling youg Business. Right around when I was researching all this, I read a book called Finish How Great Entrepreneurs Exit Their Companies. On top of that actually talks about, from Bo Burlingham, a lot of the emotional impact of selling a business that if the entrepreneurs didn't have the next thing they were going to, many of them got really depressed. Buy Them Build is interesting to read about the other side. So Walter Diebel talks about why you should buy a business, not always build from scratch. So I was kind of learning what makes an appealing business to buy. I read exit rich, the 6Pmethod to sell your business for huge profit and Lost and Founder A Painfully Honest Field Guide to the Startup World by Rand Fishkin. He also talks about just the, ooh, the big rollercoaster of all of this. I mentioned Lexi Grant. She also has a new platform and podcast. They got acquired so they have a great newsletter. And again, she was episode 93 of this podcast so early 2021. I was just doing so much research. At the same time I was working on the free time book proposal because I didn't know if I would work with a big publisher again for that book. I was also researching all of this. What does an exit look like? What would I need to do? Where do I need to get the earnings? What makes for a sexy saleable company? The main things that help a company be saleable. And again, I'm not the expert and I haven't even done this, but my understanding of it was that recurring revenue is the holy grail. I did have that for every single stream of income. And I'll put in the show notes the link to the episode where I share my five main recurring revenue sources. So recurring revenue. They definitely don't want key person risk. If it appears that the founder is so inextricably linked with that revenue, that's not a good thing. So the founder needs to show that the business can succeed without them. And I had a little bit of or a lot bit of key person risk because I was still the main messenger for the brand and running the podcast and such. They want to see revenue from a diverse base of clients. So in terms of licensing I didn't have probably enough clients. I had a handful, but that is not as compelling because if any one goes away, the business is at risk. And then another main consideration is just overall revenue for the business. In the case of tiny capital, it was clear that they were looking for businesses that had about a million dollar annual run rate. You'll hear people throw around the term ebitda. I find it kind of an annoying word, just sounds annoying to me. But EBITDA stands for Earnings before Interest, Taxes and Amortization. And for some reason this is the main phrase. People talk about measuring company profitability and how you can compare, sort of compare apples to apples. So who even knows what my EBITDA was or is, but I could just basically share the numbers of top line revenue and then what my operating expense revenue was.

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I was on shaky ground in all of these regards. I could have made the case either way and I think somebody who felt really passionate about this story part of the business could have seen a lot to like. There was also a lot of room to grow and it's not like I had already installed a CEO, someone who was operating the business without me. What I liked about Tiny was that they really left it up to the founder, whether the founder wanted to stay involved and operate the business even if they weren't the full owner anymore, or whether they wanted a full, free and clear exit. I liked the fact that I didn't have to know that to even explore this path. Ultimately, in all the areas I just described, I was just south of having it be really saleable. And the reason that's important is that it wasn't worth it to me to sell it for too low of a multiple. That's also something that you'll hear thrown around a lot is what multiple? Whether you're listening to podcasts about this or reading books, it's what multiple of EBITDA can the business yield if they were to sell it? When I had Greg Alexander on, he talks about if you're basically a quote body shop, you're a service based business that requires people to run it and it's not as scalable. Sometimes those will only sell for 2x3x multiple of EBITDA or 12 month trailing revenue. What was your revenue the last 12 months? Or you could average that out over the last two years. Contrast that with SaaS, businesses, software as a service and those could sometimes sell for 10x or more multiple. Imagine that averaged out I was earning, let's say $500,000. While a 2x multiple, if I was lucky, would mean selling the business for a million dollars, that still felt a little low to me because there would be a lot of work involved and the value of that business, if I just kept it in a steady state, could be a million dollars over the next five years. I now a million dollars is nothing to shake a stick at either, don't get me wrong, but it wasn't having me spring out of bed to spend the next two years preparing for a sale and the year after that handling the transition of a sale, it was still feeling a little low. Often when I'm talking with fellow entrepreneurs, we'll say what's your number? What is your number that you would sell something you've worked so hard on, you've built for so many years? What would you sell it for? So let's say if you were to sell something for $5 million, well, even a 5%, very conservative annual return, 5% of $5 million is $250,000. So that's where you start to get into that. The interest, your base principal money that if you invest that money wisely, the base interest every year can kind of pay you a salary. If you say it's $10 million. Amazing. Okay, well, a very conservative 5% annual rate of return may be $500,000. Now, we're starting to get really, really abundant with what's possible at those numbers of an exit. In my case, I did write to Tiny, they were not interested. So I at that point realized that I would either need to heavily invest in finding and training a CEO or heavily invest in cleaning up the business to make it more saleable. And the irony that a lot of these books talk about is that the more saleable you make the business, the more you're the one that wants to keep running it, because all of a sudden it's even leaner, even meaner, even more profitable. So at that point, it's not as clear of a decision. Once you optimize everything you would need to optimize to make it attractive to a buyer, that buyer might be you. Just as they say that within a long marriage, you're almost remarrying the person several times. Looking back now from pausing my decision to do anything at all related to selling that side of the business, I see it as remarrying my business, remarrying that brand, the Pivot brand, and book and podcast and courses and licensing everything I built. And now that we're even a year and a half, almost two years past that time where I was considering selling it, I have remarried it. You know, I started publishing weekly podcast episodes again, and I'm still as proud of what I built. So that's why I didn't talk too much at the time about potentially selling it, because I don't even want my community to think I have one foot out the door. It's almost like all this talk of quiet quitting you. I didn't want anyone to think I was quiet quitting that part of my business. I just needed to figure out, can I run both? Can I do Pivot and free time at the same time without negatively impacting either one, without diluting my focus too much? That remains my biggest open question around all this. The other thing that had me pull back from just thinking about the money, what could I get for this? I didn't quite put it into words until I recently heard a podcast interview of Marc Maron on Stephen Bartlett's the Diary of a CEO podcast. And this came in toward the end, really. I would say 30 minutes from the end. I'll put the link in the show notes. They were talking about existential questions. Mark was saying that society has become so affluent and comfortable that we're all confronted with this why? Question much more and more prominently, who am I? Why am I here on earth? What am I meant to do? Is this the best use of my time? He says, these are really effing hard questions to answer. To me, it's a very silent cost of our affluence and comfort. The host, Stephen said, one of the most destabilizing moments in my life was the day someone offered me financial freedom. Then what? I'm trading off my purpose for this big pile of cash. Steven says he had a bit of an existential crisis. And then Mark said, and I found this so interesting that he had a very similar experience after Subtle Art took off, which has been a mega bestseller like one of the goats, the greatest of all time, probably of our recent decade, that he had these massive royalty checks coming in. And he said for 10 years before that, my big goal in life was to become a best selling author. I want to be one of the most popular authors and bloggers in the world. Then it happened and all this money showed up and it really effed with me. He said, I sat on the couch, I played a lot of video games. What now? Any book I write is not going to sell as well. So that's not super exciting. Grinding on my Internet business, which I've been doing for seven or eight years up to that point, suddenly I have more money than I need. So what am I really doing this for? It comes back to earning that. Why?

The last little bit I want to share with you is that Mark said, when you're coming up, it's really exciting and very easy to know what you're gunning for. You've got nothing to lose. I started broke, I'll be broke again. Let's do this. But once you get there, he said, I've got contracts, an agent, an audience, a team. Suddenly there's a whole lot to lose and it becomes a lot harder to know what are you gunning for? What's the next mountaintop? He told Stephen that the year after Subtle Art came out was probably the most depressed I've been since I was a teenage. This really landed with me that just because you even can exit a business, if you've built it to a point where you have the option to exit, doesn't mean it's going to make you happy. Just because you get millions of dollars coming in, whether from a best selling book or selling a business, doesn't mean it's going to make you happy. As I considered selling the pivot part of the business. First of all, there's also reputation risk. I might be too controlling and perfectionistic to let someone else run that brand completely because it still has my name attached. But moreover, why give away this thing that I've worked so hard on building that's not guaranteed to make me any happier? Whereas if I can continue to nurture if and again, this thesis is still open to questioning. But if I can hold both pivot and free time. And the reason I don't talk too much about life after college is that is one form of pivoting, so that kind of rolls into the pivot part of the business. If I can hold both, maybe I will find that joy and meaning in nurturing both tracks, at least for a little while longer. Because I could tell you that my joy and meaning was not, at this stage of my life, going to come from training, mentoring, onboarding a new owner and doing all of that. I could just feel that although that might be, on paper, the prudent thing to do, that's not in my strengths. It's not in what energizes me. And I decided that I would rather have the business kind of chugging along, even though it could probably grow much faster with someone who was growth oriented and wanted to double down on sales, that I could keep it as part of my broader ecosystem, keep having such meaningful engagements and interaction, and keep exploring where both podcasts can go than to do anything dramatic. So this is a long, winding road, as my friend Travis has a podcast called the Winding Road. A long winding road of what from the outside looks like nothing at all. I did not sell the business. I have no buyers on offer, nothing at all. Just a lot of internal thinking, researching, processing. And I have to say, I'm so grateful for everything I learned about what it does look like to exit a business, what other founders have shared. There's tons of podcasts about this topic as well. I'll link to those in the show notes as I remember more and more of them. But I loved learning about not just the building and the struggle for the growth, but also the different forks in the road once you get there, keep growing, close something down. Exit. Do I envision passing this on to other people even after I turn into cosmic stardust? Again, I don't know. And so those questions were really fruitful, even though again, from the outside there was no outcome that any of you listening would be able to see. It definitely enriched my understanding of the path and journey of entrepreneurship and running a small business with a delightfully tiny team. As always, if you have thoughts on anything I've shared in this episode, leave me a voice memo@itsfreetime.com ask thank you so much for being here. Listening everybody. Thank you. If you're a longtime pivoter, a life after colleger, a free timer, I wouldn't be here doing this without you. Thank you so much for listening. Have a beautiful rest of your day.

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