102: How to Pivot Your Business When You Feel Trapped by Its Success with Jason Van Orden
8 Dec 2025 · 56 min
Jason Van Orden built a successful business that left him feeling trapped, so he took an 18-month sabbatical and eventually moved on. He talks about depression returning during the pivot, finding help through a mastermind group, and using frameworks like the 3Vs (vision, value, voice) and 3Rs (relevance, resonance, remarkability) to rebuild his identity and find what's next.
Questions this episode answers
June 3, 2018.
Jenny mentions 8 million downloads (over ~10 years).
Planned: 90 days (experiment). Actual: ~18 months.
Success trifecta (vision, strategy, execution); refined into 3Vs (vision, value, voice) and 3Rs (relevance, resonance, remarkability).
Chapters
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What's next? This is a question we're all having to ask and answer more frequently. I'm Jenny Blake, your host of the Pivot Podcast and author of Pivot. The only move that matters is your next.
Notes from this episode. Visit pivotmethod.com podcast. If change is the only constant, then let's get better at it. Here we go.
Hello, everybody. Welcome back to the Pivot Podcast. I am so excited to have my good friend Jason Van Orden here today. Jason helps thought leaders reach a larger audience with their ideas, create new income streams from their expertise, and build business models that align with their goals. In September of 2005, Jason Co founded the first ever podcast about Internet business mastery and online marketing. And it quickly became one of the top business podcasts in the world. Jason was there before any of us were there, so I can't wait to dive into that. And his mission now is to help visionaries with impactful ideas reach the people they serve best and the problems they are uniquely positioned to solve. He's also working on a passion project discussing entrepreneurship and mental health. Not to mention has an amazing wife, Melanie, who I've also had the pleasure of getting to know through our mutual friend, Dorie Clark and the most adorable daughter, Jason. Welcome to the show.
Hi, Jenny. Yeah, thank you for having me. This is great.
When we first met, you were going through this self described two year mega Pivot process and I remember you saying that one of the things you were exploring is what to do when your business feels like a prison. Take me to that time and what was going on when you started to feel stuck in this very successful business that you had built for yourself.
Yeah, so this was in 2014 and I was living in Paris at the time. And the reason I mentioned that is that this was the achievement of a, of a pinnacle lifestyle moment to live in Paris with my wife and my daughter. We're talking a goal we'd had even before I knew I'd be an entrepreneur. So there I was, living this moment with a business that was providing for that to, you know, be possible, the flexibility the finances. And as much as I was loving living in Paris, I was noticing that a good string of days, and maybe even some months, weeks and months had gone by where I just wasn't that fulfilled by my business. And it, you know, it wasn't even like. It was this realization that I fully embraced and accepted, even though it was kind of there. It needed to sit and really try talking to me for a while for me to go, okay, wait, something's wrong. I need to listen. And I, you know, I think the reasons I wasn't listening is number one, you know, being afraid of what would that mean for the business, A business that was successful that I had been in for 10 years, a business that was based on teaching other people how to pursue something in life of passion and meaning and fulfillment, based on their strengths. And yet here I was, all sudden a business that didn't feel like that for me, which triggers thoughts of imposterism and being a fraud a bit, right?
And then what does that mean? If I let the cat out of the bag, so to speak, and admit to myself this isn't doing it for me anymore, and yet I'm in the middle of living the lifestyle in Paris that depends on that very business to allow that, right? So that was a scary moment that took a while for me to go, okay, wait, something needs to happen here. And my wife Melanie, who is amazing, mentioned to me, like, she could tell. I mean, she. She knows when things aren't going well, even though I can very much kind of go inside myself and not share as much of what's going on. And she encouraged me to go on a personal retreat, which is pretty fantastic when you're living in Paris and you can just, like, take a hundred euro flight to Rome or Amsterdam or whatever, right? So I was like, okay, great, I'll go to Prague, because I've never been there before. I know when I get out of my element, I go somewhere new, somewhere novel. Something's bound to come up. That is an insight. And an insight did come up. The insight was I need a sabbatical for my business.
Which was scary because I had no clue how that could possibly happen because my business was still pretty dependent on me and my ideas and creating value and ideas on a regular basis. And I didn't dare bring this up to my business partner because what would that mean if all of a sudden I mentioned to him I might not really dig our business anymore. And now that's, you know, you can't put that back in the bottle once that's out. And, like, all of a sudden, he's gonna be like, great. Jason's not invested in the business. What does this mean? So kind of scary, like, have these realizations and to not have any clue of what that was going to mean, it's terrifying.
I remember I also, when I was going through my big. You call it these inflection points that I know you have a real interest in with being kind of moving on past life after college. And I kept. One of the things that my. That got in the way was I kept saying to myself, don't bite the hand that feeds you. And I just felt like what you described, although I wasn't advising people on how to build a business and then getting. Hitting a plateau in my business, which is. That's even scarier, you know, because like you said, that was the very thing funding this big dream that you and your wife had had since you got engaged. But I remember it was very hard to even admit that I was struggling because I didn't want to bite that hand that feeds me. And the same thing happened when I was at Google. How did you get over that? How did you just accept those feelings? That paradox of entrepreneurship that you can get tired of the very thing that you built that got you the success that you have? What were your first steps after having that aha in Prague?
Well, at first, I, you know, I thought maybe I would just somehow fix it and not have to really bring it up or face it, which wasn't going to work. It actually took another two or three of those retreats, which Melanie very graciously encouraged me to. You know, so one in Rome and one in Amsterdam, and one which was fantastic. But every time it was like, yeah, some scary realization coming up. Finally, it just. It was clear to me. It's like, okay, there's only one next step here. I have to talk to my business partner about this.
And usually I think in these moments, there is some kind of conversation that needs to be had with someone when we're stuck in these kinds of business or otherwise, right?
Thankfully, yeah. I mean, he was very understanding. In fact, he in some ways had been having similar feelings. I mean, we'd been in this business for, like, 10, 11 years at the time. And that for some entrepreneurs, it's a very long time, especially a business that you're very much integrated in yourself, not only as, like a CEO, leader of the business, but it was our ideas and our voice and everything.
So that was a relief and a big lesson was that through two or three Long conversations because he was like, yeah, sabbatical would be great. What seemed like an impossible idea, we found a creative solution eventually and that was here is a way that both of us can have the space to explore outside of the business. What does this mean? Is there other? Do we just need to find some other. What are the possibilities? Like, do we just need to find some other outside pursuits and that'll re energize us and then we can keep the business going too. And thankfully, the realization we had was, oh, there's, there's this woman in the business that we've been working with. She, as a freelancer, she was doing lots of copywriting and all the other things. Like, you know, she know, she knows a lot of the aspects of the business. I bet she could run things if we asked her to. And that's what we did. We said, okay, great, we will just show up to do the podcast because that needs to keep happening, hand the reins over to her and give herself this space. Let's just do a 90 day experiment.
And see how it goes. And that 90 day sabbatical actually turned into an 18 month sabbatical, which was actually quite dreamy. It was like, hey, I was working maybe four hours tops a month on that business and it continued to make the money that I needed to live off of. So in many ways it's like, oh, well, this is kind of what, you know, a lot of us talk about with lifestyle business anyway. Right, right.
So that was nice, what you had been teaching people for years.
Right, right.
And that itself is a great example because we think about taking sabbaticals from corporate jobs and there's a lot about that. But very few people talk about how do you take a sabbatical from your own business? And I love that you and your business partner were able to design that together.
And I was inspired. There's a TED Talk that I'm sure you've seen and I'm forgetting the gentleman who did it, but basically I think he takes a sabbatical from his business like every, for a year, like every seven years or something like that. So anyway, people might want to look that up because it was quite inspiring just to hear that. But the outcome of that sabbatical was that it was exactly what I needed. It gave me the space. I mean, I was realizing I hadn't been giving my, in the business, I hadn't been giving myself the explore my curiosity like I needed to. That that's very much something that fuels me. I'd been getting far Too much tied into just strategy, strategy, strategy. What's the next right answer? To grow the next number to the next level. And it just choked out all curiosity, intuition. I, you know, I was leveling out in mastery and growth because I'd been just been teaching and doing the same things for years and years and years, but by having the space to, like, start exploring, I was like, okay, now what am I interested in? Who do I want to work with next? Or now who do I. What do I love about what I've done in the last decade? And what would I be fascinated to try more of? And by the end of that 18 months, it was clear that I couldn't go back. I was like, yeah.
It was nice that it kept working, but the way that we took that sabbatical, actually, we discovered wasn't completely. We don't have to get into details, but wasn't completely sustainable. And so about 18 months after that sabbatical started, there was like a. A definitive moment, was like, okay, we have to decide, are we re engaging full time with this business to keep it going and grow it again, or are we done? And the answer was very obvious to me. I'm done. I've got other ideas and things that I'm ready to pursue. I'm still not 100% clear on them, but I, for sure, yeah, what I was doing was great, but I can't go back to doing that anymore.
And especially for you, having a podcast and as you said, being so close to it, if your heart's not in it anymore, you can't. It's so hard. I feel like a podcast shows everything. You know, you can't really fake it in that. In this format, it's too intimate.
And to be honest, I think. And we might have even said this towards the end of the podcast, I think people probably, that we said, you probably, you know, we were talking to the listener. You probably could tell the last couple years it's been different. And that's for the exact reason that you. You say right there. And.
It, you know. Yeah, so. So that. That moment of. That moment of truth right there, as certain as I'm making it sound that I was in that moment, two things are still very much on my mind. Number one, I guess I failed this business, which obviously, in hindsight, logically speaking, just ridiculous. Like, it's ignoring all the people we taught, the money we made, the things we did, the impact we had, and for some reason just felt like, oh, I guess I failed that business because. And I had to just you know, emotionally remind myself and believe it's like, no, I am making a decision here to move on. Right. This is not failure. And number two, though, was this identity shift that had to happen. Because in a way, I was like, well, if I'm not Jason Van Orden of Internet Business Mastery, the first business about. The first podcast about Internet business, you know, and everybody knows me for, like, who am I? And that wasn't easy to let go of that.
Those are so huge. The feeling of failure, which, as you said, I didn't share all the stats at the beginning, but you had 8 million downloads of this podcast. What more could you probably even say over 10 years of episodes about creating an Internet business? And in a way, I feel like, again, you. Not only were you not a failure, it was a huge success because it provided the platform for you to grow. And then, of course, you're going to want to expand. Just who you are as a person. As you know, I would call you. High net growth. Wanted to expand beyond that. And it's in my mind, just a huge success. Even how you and your business partner were able to figure that out together.
Yeah, yeah.
How did.
And thankfully in there, that's when your book came out, I think was about this time.
I know that sounds like timing. Good timing. Yeah, exactly. And when we got to meet.
How did this time lead you to this interest and passion you have now in the link between entrepreneurship and mental health?
Yeah. So underlying all of this, I mean, accompanying this, was that there was definitely a depression that was returning. And at first I just thought, oh, well, this is a lack of, you know, just, I'm not engaged in my business, it's not energizing me. And that certainly was part of it. But.
At the same time, and I don't know what all the factors are that contributed to this, but depression is something that I have had struggles with for 12, 13 years. And, you know, I've been able to manage it, you know, for the most part, for a lot of that time. But.
It started really just rearing its ugly head again during this period and even during that sabbatical. And.
One of the ways it manifested, which was really hard for me, was as just a lack of motivation and creativity when it would really flare up. And so over those 18 months, I had this cycle of, you know, I've got this space to discover. I'm going to follow my curios curiosity. I'd get like, an idea of, like, ooh, this could be an interesting book to write, or let me go to this conference and see what that's about. And then I get excited and, you know, and I'm allowing myself to kind of discover and follow curiosity, do little experiments, which is something you talk about. But here's the problem is, like, I would get an idea, I'd get all excited about it, I would dive in, and, you know, maybe I'd get a week into it, or maybe you'd get six weeks into it, and all of a sudden, just, bam. It was like the floor dropped out of under me. And it was just like, all apathy, no creativity, no motivation. And, you know, the first couple times you're like, okay, so that wasn't the right thing. That's just a sign. I'll try the next thing. But after, like, the sixth and the seventh and the eighth time, I got to this point where my biggest fear was that I couldn't trust my own motivation and creativity anymore. And to some degree, for a while, it felt like, oh, well, maybe that means I've used all my good ideas. I guess that's it. I had a good run and, like, all these weird, you know, in hindsight, seemingly irrational ideas, but that felt very emotionally true to me at the time. And so over all these cycles of that boom and bust of motivation that was completely unpredictable. And when it would bust, it was like, oh, is this going to. How long is it going to take for it to come back? I had no idea. And my confidence was just eroding every time. And so it got to the end of, like, what would it be, 2016? Where, yeah, I was just, like, not only lacking motivation and creativity, but my confidence was just, like, shot because I just. And. And I was isolating myself more and more, not talking about this stuff. And. And so. Which is, like, the worst thing to do when you're. When you're in that kind of.
But it is the impulse, and I.
It is the impulse for me, too.
Losing the confidence in myself was probably one of the worst feelings of the whole thing. It's like, I could deal with so many ups and downs, but when I no longer trusted myself and had confidence that I could do this or that I knew I was on the right track. It's so hard.
Yeah, totally.
And the one thing that I was managing to do, I mean, I was still making, thankfully, like, the money that I needed to kind of keep things going, because by then, like, the other business, because we had, you know, extracted ourselves, it was clear it wasn't just going to keep making the money. It was. And so we were letting that go. So that money was starting to disappear.
And so, I mean, in that moment, with my confidence getting shot and everything, I did ask myself, well, what's. What's something that can still kind of engage me? And the answer was, well, I'll do one on one consulting. Because when I am in the room with somebody and I'm feeling like I'm showing up to help and serve them, like I am able to in that moment, show up and, you know, and get results for them, and then I'll, you know, go back home and feel like crap again. But like, at least, you know, so that's how I was like making money now the whole time, though. And I can touch on that a little bit more in a second. That one on one consulting was actually serving a whole lot of other purposes other than just keeping some cash coming in.
But at the end of the 2016, I finally had to go, okay, something like this, really. And it's weird because it wasn't even like I was fully identifying it as, oh, this is depression coming back. And I was resisting that idea too. And finally I had to go, you know what? This is? Feeling just as bad or as worse as this one summer way back when. And that was. And so finally I was like, okay, I. I'm going to go see a psychiatrist and I look somebody up and I went and saw him and he's like, yeah, I think we should, you know, get you some medication, get you feeling better, and then we can start, you know, looking into other things. And that was certainly, first of all, just like the acknowledgment of that. And then the second of all the, you know, and having a professional acknowledge that. And second of all, you know, medication can be a great help to kind of start turning things back around.
Was. Yeah, that was the moment that things started to get better. But one other thing I wanted to share that happened in that time there was that a friend of mine invited me to go to just kind of like a peer mastermind. Hey, let's go get together in Florida. We'll rent a nice house, spend two or three days there with some smart people and help each other with each of our businesses. Right? And I was like, okay, well, I really feel like crap right now. I have no idea what I'm doing, but I know that every time I get out of my usual environment and in the room with smart people, something's going to come out of it. So I said yes, even though part of me was like, all I want to do is stay at home and feel like, you know, crud.
And, you know, to sum that up really quickly, like I went there not knowing what to expect and kind of, you know, with my list of quote unquote, strategic, tactical questions to ask them. Well, what do you think if I did this? What do you think if I did that? But thankfully, the people in that group, many of whom we didn't know each other when we showed up, just the one woman who had invited us all there, we all knew her.
People in that group opened the door just to crack enough a couple people with comments they made or whatever to allow for vulnerability to happen. Which is, I think, where you get the most out of a mastermind is when it's not just strategic, but you can go to that more vulnerable place.
So it became clear to me, I know what I need to talk about. I need to talk about this year long experience of just being depressed and losing all my confidence and feeling completely crushed and have no idea what's next. And, you know, and I procrastinated until, like, I was one of like the last two people to take my, you know, hot seat thing. Because I was like, I don't want to talk about this. But sure enough, my. My turn came and I just started, you know, explaining, and here's where I'm at, and this is what's going on. And just as I was talking about it, you know, then people started chiming in and saying, yeah, you know, I've actually been there before. Something like that's happened to me. You know, it turns out in a room of 10, like three of us, myself included, had been on medication either at that time or sometime before and had struggled with some kind of mental health. So that was, you know, just the, like, oh, I'm not the only one. Having that reminder is nice. But I think the biggest thing is that by sharing it with my peers, you know, yes, I had talked to my wife Melanie about it. Yes, I talked to psychiatrists about it. But by finally opening up and sharing it with my peers and going from my, you know, lizard brain thinking, no, you can't talk about this because you will die. Because in the lizard brain mind, it's like you say this, people lose respect for you. You are ostracized. Ostracized means death, right? That's what the evolutionary brain does.
I remember saying, if I really reveal where I'm at, my clients, the law of attraction, even if I didn't call it, that will stop working. I'll have this magnet that repels people. Clients won't come, I won't have any money. I can't feed myself. I'll be even more depressed.
Totally.
Until you die.
Yeah, until you die. It does. It feels like it's going to be death. But I didn't die. Like, I shared that, and I got empathy, I got recognition. People witnessed my struggles and my pain, and it's like, wow.
That vulnerable moment. I didn't die. And then right after that, we each had our own room with a bathroom in this big, nice house we'd rented. And I just went and had this huge emotional release I hadn't had probably since my daughter had been born five years before. And so that was a turning point. It wasn't like it all disappeared in that moment, but it was like, okay, wow. Okay, so this, you know, hope started coming back in. And so that was, you know, that was just a key part of all this. For whatever reason. Like, that was part of something that needed to happen for me in this pivot process. Now that every pivot process learned, you know, leads to a mental health crisis of sorts. But, you know, it's. In this case, it did come along with my experience, and that was an important piece that I had to start unwinding to really open up to.
The next iteration of next evolution of my career.
Well, there's so much power in truth and speaking your story. And as you said, the moment you were, you did take the risk to do that. Not only could people say, oh, me too, I've been there, and you felt less alone, but they could probably relate. And I bet everybody in the room gained something. I don't know. I don't know about you. And your wife is so bold in this way. She's talked about her experiences leaving the Mormon Church. And just when you speak your story, it's like. And that deep truth, just the room, there's this beautiful silence and wrapped attention and people. It's what we crave.
And yeah, absolutely.
Just one more thing. And then speak to both. But I can't remember which publication, but there are several articles that I've read about how entrepreneurs do tend to experience.
I don't know if we could say more mental health issues, but certainly their own variety of a constant sense of anxiety or stress or things that of course you're gonna like. Not of course you're gonna fall into depression. But it's very scary when your entire, as you said, your entire identity and ability to provide for yourself hinges on your work. I mean, it's. Everything's wrapped up in it now for many Entrepreneurs in a way that wasn't in the past, or at least it has shifted. So, Anyway, go ahead.
100, 100. And that's. Yeah, I mean, I want to look and see what kinds of numbers I can find. But I mean, it. Just after that moment, I started having a lot more conversations.
With people and bringing up and sharing. For 10 years, my business partner didn't even know that I had struggled with depression. This is just not something I wanted to share for all the reasons we already said. And so as time went on, I started getting more and more comfortable with sharing that. Which has now led to the mental health podcast that I want to start. Because I started having. I was like, okay, three out of ten people in that room. And then I started having more conversations with other entrepreneurs and more things started coming up. And I do think that, you know, because mental health can lead to maybe challenges of operating in the status quo because, you know, maybe, you know, it's just hard for you to, you know, conform to whatever models of, you know, corporate life or whatever. It's just like, I'm gonna go do my own freedom thing so that, you know, at least that stuff doesn't trigger my mental health. But then entrepreneurship itself, yeah. Brings up all these other things that can aggravate, instigate, trigger as well. And so, yeah, it's a conversation I want to see people having a lot more. And so whatever I can do to catalyze or bring that conversation would be great. Because first of all, if people can just hear the stories and go and be reminded that, no, they're not the only one that is that deals with those kinds of things. And number two, maybe they'll go, okay, this is happening to me, and there are things that can help, so let me go figure out what's going to help me. That would be great.
How has the identity piece, that big fear of who am I, if not Jason Van Orden, the host, co host of the Internet Business Mastery Podcast? How is it now, a couple years later, while you're still developing? I know you have two new podcasts in the works, and of course you're doing so many other things. I want to get into your strategy design process soon as well. But how is it for you being in this identity interim?
Yeah, so.
There was a lot of fog there, as. As there often is. And it took, you know, it was somewhere in the middle of last year where I started being able to look, not only, like, see some of it clearing ahead of me, but looking back and seeing the breadcrumbs behind me.
And I mentioned that, you know, I've been doing that consulting as cause I was like, well this is a way to bring in some cash so that I can. Because that's another thing that I needed to mentally extract myself from. My last business was just knowing that like I have another way I'm bringing in money. So whatever happens with that, it's not weighing on my, my mind. Right. And making my anxiety even worse. The consulting did some interesting stuff. You know, my last business I didn't do any. It was all digital courses and you know, group online coaching. Far more arm's length. But by showing up in a room like doing things like VIP days and one on one calls with people, I started getting all these really interesting. There was a feedback loop that started and I think maybe even you talk about feedback loops in your book or something like it, right? It was like I started having this reflection to me of where I created the best value for people, how I showed up, what kinds of strengths they appreciated in me. I would show up, you know, prepared to do one thing in a VIP day thinking, oh, this is what they're paying me for is all this, you know, we're going to figure out, outline all their emails. But in the end then finding out, oh, it was much more about following my intuition and asking good questions and just pointing out this one thing that they kind of knew but they needed somebody else to reinforce, you know, it's just like, you know, good coaching skills. But then in like very specifically me, what is it about how I see the world, about how I see people, about how I ask questions, about how I show up that people appreciate. And so that that started helping me eventually rebuild that confidence, discover new realms, new layers of my unique genius as we call it, or strengths.
And then not only that, but because of that really close association with people and seeing inside of their businesses. Well for one, being reminded that as much as we think everyone else has it figured out, guess what? Everyone's business is a mess. Okay? Yours business is not the only one that's a mess. So I've seen inside a lot of businesses last two or three years and everyone's got their messes. So that was nice to be reminded of, but then to go, oh, this is what people are really struggling with right now. This is the unmet need. These are the questions people are asking and getting ideas about how I would be most excited or could best answer those questions, meet those needs. And so my identity started to restructure and reform. And so now one Thing I tell people is, like, when they're like, man, I'm lacking clarity. You know, besides saying, hey, I've got a great framework for that to help you restructure your business and find clarity, I say, look, go have a lot of conversations with people, follow your curiosity, maybe even think, as counterintuitive as it might be, go back and maybe do some consulting or something like that, even though it's not scalable or whatever, because you just. Yeah, so many great insights come out of following your curiosity, having these conversations and doing this consulting. I guess that's three Cs. That works out really nicely. I know you're a framework person, Jenny, so everybody does that.
I love it.
Three Cs of clarity, conversations, curiosity, and consulting. Oh, content. That was another thing.
I started creating brilliant four Cs.
Yeah, I started creating. Yeah, I started creating content again and discovering new.
Aspects of my voice and just really exploring with that. And, you know, this is like another, you know, year from that moment moving forward. But, like, yeah, the identity started restructuring, and those are some of the tools that helped me. And now I would say, like, you know, I've discovered a part of my voice I never knew was there before. I am leveraging strengths that I had either ignored or even hadn't even fully realized were there. And, you know, I consider myself somebody pretty. Tries to be pretty aware about my strengths and infuse those, but there's always more you can learn about yourself. And, yeah, I have this level, new level of confidence about what I want to say and do in the world. And certainly at that moment in depression, it seemed, like, impossible to refind that. But.
Bit by bit, following the kind of process that you talk about in your book, little experiments and taking stock at key moments and feedback loops, the identity did a new identity, one that I even embrace and feel even better about, that builds on what was there.
Emerged. It showed up.
Yeah, that's what gave. I had a huge smile as you were saying that, that you were able to find and reconnect with parts of yourself that weren't even expressed in the last business. So it's not like you're trying to rebuild the exact same holy grail that was stumbling upon podcasting super early in 2005. But in this new direction, there's so much gold to be mined. And I just loved hearing you say that you feel even more yourself now on the other side, which is, I think, the gift for going through this hero journey of entrepreneurship gift.
Discovering these new parts of me, I knew that were There. And number two, which is, you know, kind of the cliche, cliche thing that people say. But that struggle of the last two or even three years now informs my business in so many ways. Like, that extreme lack of clarity has helped me now.
In being better at helping entrepreneurs who are also now in an inflection point, find that clarity. Because I've been there in these depths and brought back these tools and insights. And I feel like it's also given me a new level of, I don't know, compassion and empathy and ability to see and serve, having gone through this gauntlet of whatever this abyss of. So, yeah, it's a nice Phoenix metaphor, new identity. But then also, like they say, like, the stuff you go through then allows you to bring that forward and use that in ways that bring a lot of value to other people.
Absolutely. It's as if life hands you the missing piece. Like, oh, you're a business strategy consultant for 10 years and you're leading all these people. Well, here's something that might be missing. And that's what I found too, that going through the struggle, just like you said, I now that time showed me what's missing actually in the market. Because why did I struggle so much? Why was it so hard? And that gave me an opportunity to create something new out of that as I solved that for myself. One thing that intrigued me from your website, you talk about the size, the success trifecta. If one or more of these three things is lacking, your progress and growth will slow or even stall completely. So now I'm dying to know what is the. Why can't I say that? What is the success trifecta? I encourage you to try. That's a tongue twister.
That is a tongue twister. So here's what's funny is you're gonna have to remind me what the success trifecta is, because I probably changed the name to something else and forgot that I used to call it that.
That is so funny. Well, I don't know, because that's all that I wrote down, but I know that you do have, like, another thing that you've said. And so maybe we can just zoom this out to what do you find? Having worked with entrepreneurs for over 10 years, approaching 15, what do you find is missing for people who seem to have successful businesses from the outside, but they hit these growth plateaus and can't seem to take it to the next level?
Yes. Okay. And I actually found on my site. And see, this is so interesting because this is. I can see how this was like early stuff that's now developed further into the frameworks that I teach in the workshop I have now. But, yeah, I like the question you asked. And for those who are curious and dying, the success trifecta was actually vision of where you're going, strategy for getting there and then frequent execution and doing the work to execute according to the plan. So it is a useful framework sometimes to go, okay, if you're feeling stuck. Is it that the vision is unclear? Is it that maybe you need to change the strategy because that's not working for you? Or is it just that you haven't really been consistently executing on the strategy that you've chosen? But even further to the question that you asked, yeah, here's what was missing for me. So, like, my workshop focuses on helping people do a deep dive and realign in three areas. Number one is going back inside of themselves and checking in again. And this is kind of some of the stuff that you do in your book too, like checking back in with. And what I call it is a 3V. So this trifecta actually kind of turned into some other things, the three Vs, which are vision, value, and voice. So. So vision is checking back in with where you want to go. And sometimes especially quick start, fast hustle entrepreneurs, we start executing on a vision and don't realize maybe that vision has shifted or that we have drifted away from it. And so we always sometimes need to check back in with, where was it that I was headed again? Why did I want that? Sometimes that's a quick little check in. Sometimes it's a big one. Right? Voice is really important, especially I work with a lot of thought leaders. And now these days.
You know, I started a podcast in 2005, and that was novel and new and cool and took off into a business because I was there first. And the podcast itself was kind of the thing that made it interesting. We're out of the wild west now online, like these channels. And yes, there are. There's new channels emerging, but, like, things are a lot more saturated, these things. Like, you're not going to start a podcast, and by virtue of starting a podcast, be cool and new and interesting anymore. Now you got to, like, really know what is it you're saying, who you sing it to and why does it matter? And so, you know, that's where I really challenge people to get specific about, like, you know, not just having a vision of where you're going, but knowing, like, why. Why is that vision important to you and why is it important to the people that you you serve through your business. And knowing, you know, voice is something that like artists talk a lot about. But I think it's important for, well, anybody who creates and certainly thought leaders and entrepreneurs. We, we create. And so like there's a perspective to what we do. There are values that drive it, there's a motivation. And that's probably, I mean, most definitely connected to past experiences, probably some of our hardest, deepest, darkest past experiences and challenges we've been through.
And so being aware of that, but then also infusing it into your work and making sure your audience knows, this is why my business has meaning. This is why it matters. If my business went away tomorrow, here's why it would not only be a bummer for me, but for the world because here's this thing that needs to be said. And so that's the voice piece. We could do a whole episode just on that. And then value is kind of that unique strength, unique genius stuff is getting a lot clearer. And you know, there's a lot of great assessments out there and we take those assessments sometimes. StrengthsFinder 2.0 and these are great. But I also find that a lot of times we take them and we go, wow, that's cool. Like I just read my horoscope or something, right? And then like three months later, it's like it's drifted out of our consciousness and it's never managed to really seep into our messaging and our systems and our business and the way we spend our day to day. And so, you know, like, not only is it important to unlayer new elements of your strengths and unique genius, but then to be very deliberate about remembering, like, this is how I show up best in the world. And so the decisions I make about my business, the product offers, the marketing, the messaging, the sales, what I focus on in the business, team systems, like they all need to hinge on the fact that this is how I and I call it. The best self exercise is like here's 10 statements of how you show up and create the best value in the world and refer to those often when you're making decisions or else you are robbing yourself and the world of value that you could create and fulfillment you could have. So vision, voice, value. And then very quickly check back in with the audience. And this is three Rs. Relevance, top of mind, pain. This is just marketing 101. Are you solving a pain? What's the unmet need? And is it something they're actively looking for, willing to pay for it? But then resonance is understanding, well, what is Motivating them? Why is that the top of mind pain? What's the language they use to describe that pa? What's their perception of why they have the pain and the problem? Because often there's things that they've got wrong about that. What solutions have they tried, what have they failed at? And so now they're frustrated. It's like really understanding the deeper needs and motivations underneath that pain so that then when you speak to it in your content, in your marketing, in your speaking gigs and things like that, you're using language and stories and values that really resonate and don't just go, oh, yeah, I have that problem and I need that. But go like, oh, my gosh, it's like, I've been waiting for this person to tell me how to solve this pain. And then the third R is remarkability, which is more than just unique value proposition. And, you know, this is more. This is about. And we won't go into this, but this is about knowing. It's like, okay, well, what. You got to be novel enough for people to stop and pay attention. We're in an attention economy. And like, the easiest, the thing that they really want to do, when they come across your brand for the first time, your content, your idea, whatever your ad is, they want to be able to go, yeah, that's not relevant, or, yeah, that's relevant, but been there, seen that, done that. That just sounds like 500 of the things I've seen. It's like, how in the way you show up, are you making it? So it's like, whoa, okay, wait a second. This isn't, you know, five years ago, Paleo was novel. Now Paleo is not novel. There's a lot of Paleo coaches out there. So how are you making Paleo different? Just to give a concrete, like, so vision value, voice, relevance, resonance, remarkability. And those are two phases. And the third phases. Now let's look at the business model and go, what's out of alignment with those three Vs and those three Rs? Let's look at the messaging. Let's look at the channels you're using to communicate that messaging. What's the value proposition, the services, the products, and the way you deliver those services and those products and just all the pieces that make up a good business model. And very quickly you start going, oh, kind of like I did. It was like, oh, my last business. Yeah, totally out of alignment with my unique strength. It reached a point where it was no longer. That piston wasn't firing anymore. No wonder it wasn't doing it for me anymore. So just as one little example, and that is then how on a regular basis you can hopefully, whether it's a little pivot or a big pivot, reclaim some of that clarity and that confidence of the next evolution of your career as an entrepreneur, your business model, your pursuits, your body of work even. Because I love working with people like, what am I creating here? What does this all add up to? And so that's what I think. Those are some of the things I think people need to be thinking about, especially in today's online climate, if they want to create something meaningful, stand out, be fulfilled, create the greatest value. And hey, heck, you'll probably make the most possible money going that direction too. And there's nothing wrong with that either.
So good. Jason, I love hearing you just riff. This is so many great gems in here about the three vs, Vision, Value and Voice. And in that section, I loved the exercise on value to write down the 10 ways that is your personal, highest and best use in the world and to keep that top of mind because it is so easy to let our calendars or schedules or email inboxes get away from us where we are stuck doing things that don't make it onto that list of the ways we have the most value. You also mentioned standing out and the attention economy and shout out to Dory Clark for standout. I love it.
I'm really curious. I did not. I think I hardly knew what the word blog meant in 2005 though. I was just launching my first website, let alone podcast. So this is a two part question. How on earth you stumbled upon podcasting in 2005? And just why? How did you. I mean, I think no one can ever know when you're about to stumble on, quote, the next big thing. But what interested you? And then now it can be intimidating because there are so many. Like the New York Times not just has one podcast, maybe 10:15. They have the, the daily that, that I know I have many friends who listen to. It can be very intimidating for a new creator, even for myself that I'm a couple years in. We're suddenly competing with the biggest celebrities, the biggest brands, and then Those brands have 1015 podcasts within the brand like Vanity Fair. And so what do you advise people to stand out or even to just encourage them to keep going knowing that attention is so dispersed now over 10 years from when you started?
Yeah, there's, yeah, there's a couple really great insights I think I can share here. Yeah, quickly, the story on podcasting Was that I was online and I was selling, you know, what people sometimes call information products. At the time, it was an information product I created that was direct marketing course for real estate investors. So how to use direct mail to find sellers and buyers and put deals together successfully.
And I needed a way to sell this. And it was like a binder of printed out PowerPoint stuff and CDs, physical CDs I had to burn. So this is like 2004 going into 2005. And so I was just like, I was looking for, you know, at the time, there's none of the social media I was on. I was posting articles on forums. Is what I was doing, like actual, you know, forums like they used to. I guess there's probably still some forums online, but. And so I was just. I had my ear to the ground, like, what are some other ways to promote this stuff? And I happen to be on this one newsletter still because Melanie and I used to be in a band. We're very serious about it. And we'd followed this guy.
Bob Baker, who taught guerrilla marketing for musicians, which included online stuff. And he had a newsletter I was on email newsletter that came and it mentioned the word podcast. And so I was like, what is this podcasting? So I entered it into Google. I was living here in New York City, this is beginning, very beginning of 2005. And Google immediately tried to correct me. Did you mean. Because Google didn't know what podcasting was yet? And anyway, I came across some blogs and things, and it was actually just like this very geeky stuff at the time. Guys talking about rss specs and MP3 enclosures and the new specifications that allowed for. And now I have an engineering background, so I understood the technical aspects. I have an audio background as a musician. I understood the recording aspects and the digital audio of MP3s and how all that worked. I was already a marketer and an online content creator, so I saw the business possibilities of it. So it just happened to be this nice combination of my and the teacher in me. I love teaching. I'd been a teacher. The reason I got into consulting and information marketing is I love teaching. So it was just like this bam of all these things that intrigued me. So it was very much, like I said earlier, a following my curiosity thing now I'd like to say immediately is like, this is going to be huge. I'm doing this. But it was actually probably six months. And finally Melanie going, I can tell you're really interested. Just try it out. Just do it right. And I Felt like it was such a huge thing. But I did. I finally put a website online about podcasting because I was like, you know what? There's no good tutorials. In layman's terms, this is all a bunch of geeks geeking out on this. What about when the other people show up and want to create podcasts? And it turns out that that site took off in Google, got the attention of a publisher who asked me to write a book. I started speaking at conferences. So that's the podcasting story now, but here's why. Another important insight here, when I was in this moment of rediscovering my next, you know, where I was going to go, and I started getting some clarity. And like I said, I was doing some consulting. And, you know, I had a good reputation and network, but, you know, you got to start, you got to do a little bit of selling to get people to sign up. And one thing that I really struggled with, and it was a friend. I don't know if you know, Michael Roderick, a friend of mine, Michael Rodrick.
Yeah.
Again, through Dory, he pointed this out to me because I was telling you, like, I'm having. There's a sticking point when it comes to selling my services. Like, I keep talking about this amazing stuff. People keep saying, oh, man, Jason, there's something about your way, your brain works. I really want to work with you. But they don't sign up. And, you know, and what it came down to, I was. It wasn't really selling. I wasn't really saying, this is how you can work with me. This is how it works. Like, and I think this is what you need. So, you know, here you go. Call to action, sign up. And I had this weird blockage because two times in a row, I had created something.
And people just showed up because it was the timing and the quality of the thing or whatever. And the one was launching that podcasting site and because it was needed at the time, and I happened to follow my curiosity and that tutorial site took off. Boom. Audience publishing deal, speaking gigs, consulting courses. Launched as an experiment, Internet business mastery to just kind of figure out the podcasting thing. Turns out that took off because early to the game, nobody else talking about Internet business on a podcast. And so in my psyche, I had this belief, like, I'm the guy that just creates good stuff and people show up. And so I had this weird. I don't know if you call it pride or whatever of, like, actually having to, like, pound the pavement and sell.
You know, and the truth of the matter. This is what a lot of entrepreneurs have to do and struggle is like figure out how to sell your thing. That's like the first thing step that you have to do. Well, I'd gotten lucky in my two, two of my earliest things that I had created. And so the point I'm making there is when you go through these big pivots, sometimes things you thought.
You'D overcome, like imposter syndrome or whatever, like those show up again and then also lessons that maybe you actually never really learned, like you might be a, in my case, 12 year experienced entrepreneur and for whatever reason way back when you didn't learn this one lesson that a lot of people have to learn.
And I had to relearn that lesson about kind of like you know, pounding the pavement sales on the phone. And not just I create good stuff and people show up when they want to buy from me. Right. So there's a couple insights I wanted to share there to answer your question and also say like whether that's, that's probably, you've probably seen this too in your research about pivots. Like that those are phenomenon that are going to show up and people need to be aware.
Yeah. And for me, I'm always striving anyone who's in my private momentum community, it's for side hustlers and solopreneurs. I think half the people are there because I don't do things I don't feel like doing. Some people are like I'm hiring you as my coach because you don't like social media. So I also find it very interesting that and in momentum my motto is always, I'm always saying on our Q and A call calls, let it be easy, let it be fun. What types of getting the word out resonate for you? What speaks to your heart? What would be easy? What would be fun? Like, I just don't for me, kind of similar to you, I probably got spoiled early on by having a blog that got to a book and, and so on. But I still, for me, I don't believe in like pounding the pavement in a way that feels like sandpaper to my soul.
I'm glad, yes, I'm glad you made that distinction.
A lot of, of advice that's out there. I end up almost purposefully having a smaller platform though I do believe in a nonlinear universe where those practices that can still lead to the perfect sized audience for me. So who am I to know? And, and I just love what you said and I think when you are tuned in to all those Things that you help your clients with about voice and remarkability and value, then the right people will come around. But it takes that work that you help people do. It's not just about the marketing, which I know wasn't the point you're making, but it does require more specificity.
Now, that's an excellent point. I'm glad you made that distinction because it wasn't about pounding the pavement and grinding. Because actually, that is a lesson I've had to learn more. Because another thing I was doing in that pivot moment, in that pivot moment is I kept looking for the next right answer. And what I meant like the equivalent of, oh, if I just put up a site about this, my next thing will take off. If I just launch a podcast, it'll take off. Like, what was the equivalent now in, you know, 2017 at the time, 2017. And it doesn't always work that way, but I had to kind of extract myself from this. Oh, just find the right answer. My engineering mind, like, give me the variables, I'll solve for the answer and I'll pursue that answer. Right. It's like, no. I've had to come to a much more intuitive ease. What's. Follow my curiosity. What feels good kind of place. And it. And it has now served me well. But that's been a learning process for me to become more comfortable with exactly what you just described there.
I'm not a huge. Like Gary V. I don't actively read or follow his stuff that closely. However, one thing he talks about is documentation rather than the finished product. And so I do think that nowadays too, it's more about being open and sort of creating content and sharing your story. And that feedback loop that we talked about, that if you can just let people in on the process, the thing is going to build itself. Like the right answer will build itself, but not up front. It's like you almost have to build into it organically while the audience is there hanging out with you 100%. That's certainly how I feel about my podcast probably. I think think some people momentum too are like, we probably see where it's going more than you do. And I know for sure that's true.
Well, you referenced a blog post I wrote, I don't remember, maybe a year or two ago. And that was like the early form. I couldn't even remember what that was because that was like the early form of what it's become now. And yeah, Gary Vee's great. Not my style. I don't follow him a lot either. So I'm gonna recommend, and this is something I bring up a lot lately, is Austin Kleon's book Show youw World Work. Same principle, just a little easy. You can read this book in like an hour and a half. And it's exactly what you just said. It's like you got to freaking show your work.
Love it. Jason, I could talk to you all day and we didn't even get into a fraction of your business mind that is just so sharp. Like even hearing you fire off the three V's and we came up with today the four C's to be added in and the three Vs. Oh, my gosh. So good. I can completely see why people just left spending time with you to figure out their business. I always like to leave people with one small piece of homework. And I know you're very practical as well. So if. When people are finished listening to this conversation, what would you encourage them to do?
Choose one of the Cs. Either conversations or curiosity. There was a couple other we mentioned, but I'm going to say either conversations or curiosity. So either ask yourself, you know, whether things are going really well, you're really stuck right now. Just like, what am I really curious about right now? Now? And then go do something to experiment or dive into that or block out an hour in the week of like, yes, this is going down the rabbit hole and it's not immediately going to pay off. But I'm curious about this right now because there's something there and your curiosity is a compass. And somewhere down the line in a few weeks, few months, a couple years, it is going to add up to something. Or conversations. If you're. Look, I'm an introvert and I talked about. It was actually a lot of work for me to come out of my comfort zone and go have a lot of conversations. But they paid off. And it just. I try to. I don't let a week go by if I can help it, that I don't have at least one really good conversation with somebody in my intended audience, my ideal customer base, just to hear again, listen for that relevance, listen for that resonance, the unmet needs or just going and talking to colleagues. Conversations are so just rich in insights and reminders. And so conversations and curiosity are just ongoing tools that I'm always using to answer the question that you and I both love. Jenny, what's next?
I love it. I love it. I also am glad you said the piece about rabbit holes and curiosity. I hereby grant permission to.
Go follow a curiosity that happens. You Cannot tell right now what it has to do with anything at all. Like, go to that curiosity. There's probably some spark that just seems so far off the beaten path that I found. Those are the ones I have the most fun following where it's not like what am I curious about in my business model? No, it's something that has nothing to do with that. And to just have the permission to say it's worth me investing some curiosity time in this, even if I have no clue where it's taking me.
Yeah, it might be an improv comedy class and it has no seeming immediate application to your business, your career or anything. But yeah.
And where can people find you if they want to keep in touch? And I know you have a couple different programs like a Mastermind and the courses, as you mentioned, so let's let people know where they can find you.
Yeah, the two places I love to interact are, I mean go to my website, Jason vanorden.com I have a newsletter.
I send out my newsletter actually quite often and then some. It's not just like your once a week newsletter, but if any of this stuff has resonated with you today, like when stuff sparks for me all of a sudden, you might get an email a day for me over five days. But that's because I've got, I'm showing my work. I got something freaking awesome I want to share and I don't want to. I promise not to waste your time, but you're going to get the kind of stuff that we've been talking about today or on Facebook, jasononfb.com that'll take you to my Facebook page, jasononfb.com and that's another place that you can follow along if you're interested in the. Yeah, the new strategy podcast that'll be starting the mental health podcast that'll be starting the strategy workshop that I the three V's and the three R's and the business alignment that I do regularly. So those are the two places you can follow with those kinds of things.
Also, that's so you to have a domain name that will redirect to your Facebook page.
I love it. Jason, thank you so much for this enlightening conversation and I can't wait for your podcast. So thank you. Thank you for being here today and sharing so much with us.
Absolute pleasure. Really love this conversation. Thank you. Jenny.
Thanks so much for listening to this episode of the Pivot podcast. Make sure you don't miss an episode or my insider tips and templates by signing up for Pivot List, a curated twice monthly newsletter where I share the inside scoop on what I'm reading, watching, listening to, and the latest tools I'm geeking out on. Sign up@pivotmethod.com pivotlist get show notes from this episode@pivotmethod.com.
And connect with me on Twitter @jennyblake.
Remember, build first, then your courage will follow. Hasn't it always.
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