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We live in a world that celebrates entrepreneurs on one dimension—their financial success. But shouldn't the objective of entrepreneurship be too enrich our lives? How do we measure that? Start-up founders Geoff Roberts and Adii Pienaar host conversations that celebrate entrepreneurs who have used their work to build interesting and enriched lives. Listen in as we seek to inspire you to reorient your relationship with work.
Ep 6 Justin Welsh v. 2
Geoff Roberts: [00:00:00] This is the Life Profits podcast, where we celebrate people that are building awesome startups and awesome lives without compromising one for the other. This week, I'm talking to Justin Welch. Justin is one of the most popular internet creators with over a million fans on social media. Beyond that, he was one of two.
Outside his early customers. And I got a firsthand seat to see how talented of a startup operator he actually is. Beyond that, Justin is just as much of a nice guy, and there's so much we can learn from his story. After a high growth career in tech sales, Justin experienced burnout and rebuilt his entire life and career, more life profits and minds.
Without further ado, here's Justin Welsh. Justin, how are you? I'm doing well, man. How are you? I'm good. What's new and exciting. Anything good?
Justin Welsh: Oh, you know, all the same old stuff, just Rocking and rolling, doing the old content job and enjoying upstate. What about you, man? [00:01:00] Nice.
Geoff Roberts: Not too much. I'm, I'm back in San Diego.
My twin boys turned five last week. So I don't know where that came from, but they're five years old now. Cool. And I'm kind of planning, my wife and I have fallen into this rhythm of every two years, we spend six months abroad and we're, we're doing that again, starting February 1st. In the thick of planning all that.
Justin Welsh: Where are you going?
Geoff Roberts: We're going to be in Barbados, uh, Scotland, Greece, Italy, and Slovenia for a month each.
Justin Welsh: Cool.
Geoff Roberts: So
Justin Welsh: have you been to Barbados? I haven't now. Cool. I've been there many, many times. So if you need any recommendations, happy to share some.
Geoff Roberts: Cool. Yeah, that'd be great. Cool, man. All right. The man, the myth, the Justin Walsh.
Thanks so much for being here and chatting with me today.
Justin Welsh: Of course, Jeff, good to see you, man. Good to catch up and looking forward to it.
Geoff Roberts: So before you became the creator of creators and the solopreneurship guy, you've had a whole nother career, but you sort of [00:02:00] reached a point where you needed to do a reboot and move in a different direction, can you start just by kind of giving us your backstory and what, what led you to this new career?
Justin Welsh: Yeah, sure. My career sort of has three, what I might call distinct phases. The first phase of my career was 2003 to 2009, where I was what a lot of folks are who come out of, you know, college. I was a salesperson and I was pretty immature and not very good at it. My dad was a sales guy for 50 years. I thought I was just going to hit the ground running and I found myself after six years.
Being fired three times. I had no track record. Like I was just had a bad career by the time I reached age 28. Second phase of my career was I got into tech. I kind of finagled my way into an interview with maybe a resume that was a bit over exaggerative, like, like most resumes are, but I was, I talked my way into a job at a company called ZocDoc in New York city, and for some reason, like, I liked the people.
I liked the flow of the city. I liked the product. Like my own maturity level was increasing. Like there was just like this intersection of four things that all [00:03:00] happened at once and it was really good for me. And that became the start of a 10 year career in tech, where I started as a sales guy door to door, and I worked my way up to being the VP of sales at another healthcare company at age 33, eventually chief revenue officer and built that company, the second one called patient pop from zero to a little over 70 million in recurring revenue in just about five years.
You know, I, I don't know if you've experienced it, Jeff, maybe the way that I have, but like burnout to me felt like, I don't like working too hard. I can work hard all day long. Just felt like loss of control. Like when you're at 71 million in recurring revenue, it's different than when you're at 1 million or 2 million or 3 million.
So every day you're just like, you know, things were stacking up and I got, I got exhausted and I felt like I couldn't figure things out on my own. And I just, I was spinning in circles. And so I decided to quit my job, give my company six to eight months notice. They asked for. We talked about six, it ended up being eight.
And that's when I started writing on the internet. And so for the last five and a half years, I've been writing about [00:04:00] whatever I've been going through. Healthcare tech, you know, writing on social media, writing about writing on social media, building my first business, so on and so forth. So those are sort of the three distinct sort of phases of my career.
Geoff Roberts: So I want to dig into the burnout specifically, because you kind of had this high flying career. You know, most people listening to this, frankly, probably work in tech and would love to have a CRO position and that zero to 70 million run that you had talked to me about the burnout itself. You said it wasn't hard work induced.
What do you think contributed to the burnout? Like, what did you feel? What were the factors that? You think in retrospect actually led you to burning out?
Justin Welsh: Yeah, I think burnout to me, the way that I've sort of best figured out how to describe it is if you've played the game Tetris. So if you go through the Tetris levels, the pieces start falling faster.
And at some point you reach a level where the pieces fall so fast that. No matter how [00:05:00] good you thought you were at the game, they just start stacking so quickly that you cannot dig out from underneath that stack. And that, to me, is what burnout really feels like. It's where you fix one problem and ten more appear.
You fix three problems and fifty more appear. And so for me, it's just loss of control. It was the inability to get my head above water when my team needed it most. And I think that was just lack of experience. Right. I took the job as VP at 33, which is pretty early. By the time I was sort of burning out, I was reaching 37, 38, still pretty early for, for sort of those C suite roles.
And I think I lacked some of the experience necessary to delegate effectively, focus on the right things in the business, leverage all the tools and people I had at my disposal. And so I felt like I was just like constantly trying to climb out of this hole, and so that became really, really difficult.
When that happens, [00:06:00] you know, especially maybe it's just me as a person, but like my pride was on the line and I always felt like, especially not now that I'm older, I don't think this way, but like at that time I felt like asking for a lot of help meant swallowing my pride. And I think if I were, I'm 43 today and I still have a lot to learn, but I think if I were re thrust into that situation, maybe six or seven years later, I may have handled it more effectively.
Sure. That makes
Geoff Roberts: sense. I think there's also an element of, you know, it's the inherent nature of sales to some extent. Even if you hit your quota today, that's what you did for me today. What are you doing for me tomorrow? And also just the environment that is often fostered and venture backed software companies, particularly ones that take off, you know, as good as you're doing, it's always, can you do that much better and be the company that makes the VCs portfolio and that kind of thing.
So. I think there were a lot of environmental factors probably there too.
Justin Welsh: Totally. And also like, I think it's a combination of environmental [00:07:00] factors and just who I am as a person. So I would describe myself maybe as a people pleaser. Like, I liked when the VCs or my CEO was pumped about the role that I was doing, right?
The job that I was, I was performing. And so I did everything in my power to kind of go above and beyond all the time. I mean, I remember hitting 16 straight quarters in a row of our, of our bookings target. And that was like four years without missing a quarter. And like, you know, cause we burned the midnight oil down to the last minute of every quarter.
And like, I got pumped by that and I kind of get some energy off of that. But after a while, like, it's like trying to sprint a marathon, like at some point in time, you just, you just get exhausted. And so that was that contributed as well.
Geoff Roberts: All right. So you reach this point where you say enough is enough. I need to do something different.
What are the things that you are specifically trying to avoid in this next career of yours or, or things that you're sort of ideas that you're purposely [00:08:00] running towards?
Justin Welsh: Yeah, at the time when I started, The only thing that I really wanted to do was do something easier. That was like in the beginning, that was like, that was what was on my mind.
Right. It was like, take a break, do something that I, you know, I could do in my sleep, which by the way, sounds great in theory, like, Oh, work is easy, but it's actually not very fulfilling. Right? Like if you do things that are in the, in this one, maybe circle back later in the conversation to what I'm doing now, uh, it's not quite as fulfilling as when you're solving unique challenges.
So in the beginning, my sort of test for like, is this going to be good, was can I do this quite easily? That, that was what happened. As I recognized that ease is not an indicator or doesn't lead to joy, right? Then things started to change. And what I started to focus on as I did more meetings and did more consulting work early in this sort of new job, Was I actually just really wanted my time back and not so much that like, Oh, I don't want to, it's cliche to say want your time back.
I didn't mean like not spend time working. It [00:09:00] meant less obligations that I didn't look forward to or being able to craft and develop my calendar and schedule. To meet my needs, not somebody else's needs. And that's really hard when you're building a consulting business, because in essence, a consulting business is really meeting other people's needs on their time, unless you kind of build it in a very specific way.
So as this business morphed from consulting and advising to being a social media creator, I started to go away from, let's just do easy things, and I started to move toward let's do things that are scalable, repeatable, have some automation, and allow me to spend more time with my wife, do things I want to do on a Tuesday, go out to lunch on a Friday.
Those are the things that became more important to me as this business has kind of morphed over time.
Geoff Roberts: Got it. And a big impetus of everything that you've done since was social media, starting with writing on LinkedIn that evolved into writing on Twitter. You've got this, you know, huge following now, people recognize you from social media.
[00:10:00] What is your relationship with social media
Justin Welsh: today? It's different than maybe when I started. When I started, everything was upside. I had never been like a popular person on social media. I didn't have followers. I didn't understand how that worked. I saw people with lots of followers and I thought, I have absolutely no idea how to do that.
And so as I kind of cracked that code a little bit, that became interesting and it also became validating, right? So like there was this validation point behind having 10, 000 followers or 20, 000 followers, even though it's really not validation of almost anything except for your ability to market yourself, which is really what it's validation of, or potentially to add value, right?
There are, there are other things than just simply marketing yourself, but that's a big piece of it. That went from being exciting. To over time, it can be somewhat of a burden because as you to this really large net in the beginning, it's cool. You get like a hater and you're like, Oh, forget it. I'm marketing myself [00:11:00] hard.
If you don't have a hater by noon, you're not, you're not marketing yourself hard enough, all that kind of like old school marketing talk. But when 1 percent of people who are haters become 1 percent of a million, it becomes loud and it becomes noisy and it becomes. And so those are things that I started to fight over time as I grew my brand, you know, large amount of just negative noise, which by the way, like everyone, I'm a human being.
So like negative noise impacts me the same way it does almost anybody else. I have thick skin, but like it's still human, right? So it can hurt, but that kind of stuff started to hit. And then my wife was building her brand and like she got some of that same kind of stuff and that's even worse when you're seeing your loved one kind of go through that.
So over time my relationship with social media soured a bit. I'm able to sort of reboot my love for it. By kind of finding myself on a, a creator versus consumer plane. I used [00:12:00] to create and consume today. I really just create, I spend very little time actually consuming. I don't have LinkedIn on my phone.
I don't have Twitter on my phone and I'll Instagram on my phone. So I don't spend a lot of time scrolling those things. I share what I think is valuable that I think my readership and my, my audience will enjoy. I post it out there. I interact for a bit every single morning and then I, and then I'm off social media.
And if people are shit talking or being negative over the next 20 hours, I'll never see it.
Geoff Roberts: Something I've heard a lot in talking to people with large social media followings is. Their goal increasingly is actually to get offline and it sounds like there's a flavor of that in what you just said, although it's focusing on creating rather than consuming.
But where do you think that comes from? Is that just like a flavor of social media burnout? How do you think about that?
Justin Welsh: I think it's, I mean, I can't speak for like other creators, but for me, it is this idea that I have a shelf life of [00:13:00] about five years in everything that I do. So like if you, if you look over the last two phases of my career, which were the, the more successful ones, let's just kind of throw away that first phase.
Sure. In two, in 2009, I started at Zocdoc and by 2014, even though I had an incredibly successful career at that company, I was done, it was ready for something new. In 2015, I started at PatientPop. I went all 20 15, 16, 17, 18, and 19 was there for five years. Right. Done with that, this is my fifth year doing this.
And so for me, it's, it's less about like what I would call social media burnout. And it's more about just like, I like the idea of this multi career life. Where every five years or so you just, you don't burn it to the ground. You're just like, Hey, it's time to do something new. You take a break, you pivot and you reemerge as somebody completely different.
Like to me, that's really fun and exciting. And I think overcoming those beginning challenges and kind of going zero to one is like the most fun part of doing almost anything.
Geoff Roberts: I like that idea of the five year [00:14:00] shelf life. I am 15 years into building SaaS startups now. And I have said very publicly many times, when I, whenever I'm done with Outsetto, whenever that happens to be, I will probably not work on another SaaS startup and people are surprised to hear me say that.
And it's not that I dislike the work. I like the work very much. I'm very happy doing what I'm doing today. I just feel like it would be very one dimensional to spend, you know, You know, more than 20 years doing a single thing. And I have that, that same feeling, but very much myself.
Justin Welsh: Yeah, man. Like, I'd love to like, okay, I've got a career as like building tech companies.
And then it's like, Whoa, that career pivoted. And now he's like a creator online. And then that career ends someday. And like, maybe next time I'll pop up like running a brewery or building a, you know, a destination resort. Like the, I just want to do something different all the time because. I think that by involving yourself in different industries and different roles, like holistically, you actually become a better person and a better business person, regardless of sort of what industry [00:15:00] you expose yourself to.
Completely
Geoff Roberts: agree. I want to move a little bit to, I actually have this written down as a topic to discuss with you. And then you tweeted something about it early this week, which I thought was funny, but it's this idea of. And when we have enough and how do we recognize what enough is in our lives to start, why do you think people struggle so much with this concept and specifically hyper successful people, every hyper successful person I see, you know, they sell a company for 20 million and then they're right back on the treadmill, trying to sell one for a hundred million dollars, like, why can people not Grasp this concept and, and live with enough.
Justin Welsh: Well, I don't know. I think that some of us are just naturally wired to be competitive. And by the way, like, I don't actually think that selling a company for 20 million and then trying to build one and sell it for a hundred million is like, I wouldn't say that's a [00:16:00] negative thing. I don't, I don't. But when I, when I wrote the article or the tweet, when is enough enough, it wasn't in response to people's ambition.
And so I think ambition is a really, really good thing. I think where ambition becomes dangerous is where we throw out what we objectively know to make people happy, spending time with loved ones, volunteering to something bigger than ourselves, being inspired by faith. Like, there are so many things that, you know, objectively have been measured to lead to joy or happiness, however you want to sort of talk about it.
And if you push those things all aside to only focus on monetary ambition, I tend to think that those people are the least happy folks that I've met. I know lots of people worth a hundred million dollars or more who I would describe as miserable. And so that to me is no judgment from me. When I wrote that article and when I wrote that tweet, it wasn't advice or a how to.
[00:17:00] It was me talking to myself, me literally writing a prescription to myself to remind myself that money and status and followers and all those things are worthless if your personal life, your health. Your relationships are in the trash. And so that's, that's why I wrote that. And it's something I try and think about almost every day because I'm addicted to like the, the traditional levers of what you might call success.
Geoff Roberts: That's an interesting comment. You're addicted to the traditional levers of what you might call success. So you, you purposely need to create space for yourself and remind yourself that there are these other things that you should be pushing your ambition towards and pushing your. Motivation towards to, to reel you back from getting sort of sucked into the Common measures of success.
Justin Welsh: Correct. I require a lot of external conversations to [00:18:00] make sure that I'm not moving in the wrong direction. So up here in Hudson Valley, I've got a really cool sort of support group of other interesting entrepreneurs who happen to live here in the Hudson Valley, because they're probably trying to do some of the same things I am, which is like chill out a little bit, right?
And so I surround myself with really cool people. Like one, one that comes to mind is Steve Schlafman. He runs down shift. He's up here. He's my neighbor and we'll get together and just have dinner and talk about like, you know, really being laser focused on the things that are most important to us and lead to that joy and that happiness and having those things kind of regrounds me because there are times where like, I get really focused on, That hedonic treadmill or like the business has to get bigger and better.
And I think a lot of that comes from the sales background too, of growth year over year, month over month, quarter over quarter growth, and that's the way that you're judged as being successful. And so I bring a lot of that thought process and that those expectations to my own business and that can be dangerous.
Geoff Roberts: Yeah. My, my co hosts, uh, for this podcast, who's not here today, his name is AD. [00:19:00] He wrote this book called life profitability and he talks about, you know, you're the entrepreneur of your business. But you should also be the entrepreneur of your life or said another way, you've got ambition that you can apply towards your business, but you can also apply ambition towards other aspects of your life.
And you need to make sure that there's a balance there, which is. Ultimately, what this, what this podcast is, is all about. Yeah, I agree. Back to the concept of enough. You've had quite a run over the last five years. You've made a good chunk of money. You've talked a lot about having a wife who's also financially savvy.
So you're a financially savvy and literate family. Mm hmm. What is enough for you? How do you define enough yourself? Is it a number? Is it a feeling? Is it?
Justin Welsh: It's a really, really good question. I think it, it has different, there are different slices of this pie. So kind of off the top of my head, if I was trying to think about how to define enough.
One slice is just, unfortunately, a [00:20:00] number part of it is like, sure. You have to have a certain number that you feel comfortable with. I think that number. ebbs and flows through the lens of like, how do you actually spend your money effectively? Versus blow through your money, right? Which is, which is what we, we try and be more, more sort of mature and responsible about our financial decisions.
So part of it is a number where I think we can live effectively, happily, we can do the things that we want to do and our money can make money while there's less pressure on me to hit that. A daily or weekly or monthly number with the business. So there's a number in there somewhere. I think another part of it is just like me being able to spend my time exactly how I want to spend it.
And so for me, what I'm trying to think about is like, at what point can I wake up in the morning and. If my business quote unquote has a poor performing day, it has zero impact on me. Like that, that is [00:21:00] like when I get to that, that's almost what is enough for me. And I think if I'm thinking about it through maybe another slice of that pie, I would think about enough is like my ability to throw myself into a new hobby.
Without feeling the pull to have to monetize it. One big issue that I struggle with is like a lot of my friends have cool hobbies that they do and they do them because they enjoy them. And I have found the more I've thrown myself into business, that business has become my hobby. And when business is your hobby, everything revolves around KPIs and metrics and revenue.
And like, I would just like to get to a point in my life where like, I'm doing something because It's the number one thing that I think about when I wake up in the morning. And if I make absolutely zero money doing it, even if I lose a little bit of money doing it, and I'm [00:22:00] happy with that result, that to me is enough.
I'm sort of trying to like ad lib this off the top of my head. Those are the things that come to me as like, you know, money, freedom, and just like the ability to enjoy oneself for the sake of enjoyment.
Geoff Roberts: Interesting. Would you say, just using a hypothetical example here, and you could have no interest in the sport of golf whatsoever, but would it be fair to say, just based on what you said, that let's say you decide to pick up golf as a hobby, it would be hard for you to be the golfer that is out in nature, enjoying the walk and the stroll with friends, and you would be the golfer that is Trying to lower their score obsessively.
Justin Welsh: Yeah, it's actually not even lower my score obsessively, like to give you some insight into what kind of a weird person I can be. It was like, like I would probably like pick up the golf club and hit the ball and be like, You know, man, there's probably a really cool like software that we could, like, it's just like my first thought always goes like, like, how can I build something related [00:23:00] to the thing I'm doing?
Like my wife gets really annoyed with me because we'll like be driving to dinner and she'll be like, what are you thinking about? And I'll be like, I was thinking about like this really cool idea I have. We're like on each one of my newsletters. She's like, stop. It's like seven o'clock at night. Like I can definitely be that annoying guy.
And by the way, that's just like how I'm wired. I it's, it's, I don't know that it's necessarily worth it to fight against it. But I think I think about business a lot because I put a lot of pressure on myself and I would love to see the finality of enough be like a day where I don't feel like I'm under a ton of pressure.
Self imposed or not.
Geoff Roberts: That makes sense. And I, and to be fair, I think a valid criticism of frankly, like podcasts and content like this. Is for a lot of people, business is their hobby and that's okay. And if they're kind of obsessed with it, that so be it, if that's their interest, that that's great. That, you know, not everyone needs to be painting, you know, it's, it's okay to have different interests.
So,
Justin Welsh: yeah. Yeah. And, and [00:24:00] like maybe just adding one more thing to, as I, as I'm thinking about it, it's like, I love to write. It's like one of my favorite things, but my business now revolves around writing. And like, there's no better way or easier way to destroy creative fun than to monetize it. And so it would be really cool to have a creative outlet that was completely unattached to monetization.
Like, I just think about that a lot.
Geoff Roberts: So moving on to just this concept of life profitability in this, this podcast, something you publish about a lot online is like, I've bit off this new career. So I can have a long lunch and go on a hike with my wife and, you know, You know, work out when I want to, et cetera, et cetera, et cetera, playing devil's advocate.
There are people who read that and we'll say, you know what, to sort of realize your full potential as a human being, you need to throw yourself into something more feverishly and intensely. And if we're all taking this, you know, lackadaisical attitude [00:25:00] towards our work and trying to work less, that's net negative for society.
What would you say to someone making that, that argument? First of all,
Justin Welsh: I can only talk about what works for me, right? So like, I try and write about how I'm feeling. My writing is not prescriptive for other people. It's not like you should all do X because I say so. But I'm also would be lying if I said I didn't have a different part of my life.
Like the first, when I started working at ZocDoc in 2009 until I kind of got out of patient pop in 2019, those 10 years, I would, I would put that effort up against nearly anyone, like those companies were notorious for being very, very difficult to work at. And we work, you know, 60 to a hundred hour weeks.
Like that was what, especially ZocDoc, like that, that place was crazy in a good way. I enjoyed working there and drank the Kool Aid and. Worked hard and stayed up till one in the morning and did all those things. Like those were all part of that, that culture. And so like, I agree. I think lots of people should find themselves in [00:26:00] positions where they're like exceeding what they think they can do from an effort and hard work perspective.
I'm not against those things. I'm just not there in my life right now. And so like, so I try and talk about what's happening with me. And then the second thing I might say is I find it depressing that like, One would be considered lackadaisical because they built a life where they could take their spouse to lunch, right?
Like that's, that's a sad statement, I think. And, and I think, I think a lot of that is culture and expectations and things that have been ingrained in our society is like, it's like job hopping. Oh, you must be bad. Or it's like, no, not showing up exactly on time at nine o'clock. Oh, you must be lazy. There's a lot of like.
Oh, you must be because you X type of thinking when like. I don't know. I think, I think most people who are really, really excellent at something can outwork an 8 hour person in 90 minutes. So, like, I look at value and, and quality [00:27:00] versus, like, I'm punching in the time card at, you know, the right time and punching out at the right time.
So, that, that's maybe how I would think about it.
Geoff Roberts: Yeah, I really like Bringing this back to your previous point about chapters in life and, you know, five year periods there's nothing to say you can't have a five year period that is super intense and then one that's a totally different pace that's, that's a concept Aaron Francis has talked about is like his, his try hard era he's in the middle of that right now and I think there's room for that too.
Justin Welsh: I
Geoff Roberts: also
Justin Welsh: think there's like Interesting chapters, which is like, I thought my, and by the way, like, just to be candid, like I work very hard. Like I, I work hard at this job because it's my business and I like doing it. Right. And I kind of described, but like the intensity that I worked with at ZocDoc and patient pop, I probably don't have that as much just because I'm older and I'm a little more tired and I'm, You know, working on my own business and things like that.
But I also, I don't believe that's gone. I also believe that tomorrow I could throw my hands in the air and say, I'm taking a two year sabbatical and two years from now pop up at age [00:28:00] 45 and have a second intensity spell in my life and be really, really happy. And I'm freaking excited for that.
Geoff Roberts: Likewise.
Awesome. I want to shift a little bit to some more life oriented topics. You had a career that took you from New York to LA to a bunch of different places to live. And as you kind of rebooted your career, something we talked about prior was you, you sort of went looking for a new place to call home. And I'm curious.
First of all, tell us, you know, where, where you went and what you were looking for, but it, it seems like you found that in, in Hudson Valley. So bring me on a little bit of that journey. And then I, I want to hear specifically, you know, what you'd like about Hudson Valley so much and describe it to people who haven't been there before.
Justin Welsh: Yeah. I mean, the first place when I, I was living in LA when I started my business and then the pandemic hit and like, I didn't know if this was going to be successful, I had no idea. And so my wife and I originally moved to Nashville because, you know, We made a spreadsheet and that's what came out on top, which is not a great, not a great [00:29:00] process for picking where to live.
And Nashville was fun. It wasn't the right city for us. It's the right city for lots of people. It just wasn't right for us. And when we went to leave Nashville in 2020, we were trying to figure out where to go. I've lived in New York twice, LA twice, San Francisco, Boston, all over the place. And we just didn't know where to go.
And we came up to visit a friend here in Hudson Valley, which is a very large part of upstate New York, directly north of the city, about two and a half hours is kind of how I would encapsulate the Hudson Valley. And we sat on his 12 acre property on his patio and we grilled steaks and made a bonfire and drank wine and it was awesome.
So we came up here five or six more times. And what we were really looking for was a few things. We were looking for space. And when I say space, I don't mean like property space. I don't mean like acreage. I mean, just mean like. Space like space to. Move around and to be free and to not feel the chaos of living in the city.
I wanted peace, right? Maybe peace is a better word than than space. The second thing I wanted [00:30:00] was a really cool entrepreneurial community. And like the thing about Hudson Valley is this is the second home for many New Yorkers. And so lots of my really good friends up here are lawyers, doctors, VCs, entrepreneurs, CEOs.
And they live here on the weekend. Some live here full time, but a lot of them are weekenders. So I get this exposure to these really smart, hardworking, talented people in an environment that is much different than say New York city, right? On the flip side, New York city is two and a half hours away. I can drive, I can take the bus, I can take the train.
I can be down there in two and a half hours and I've got. everything at my fingertips and I can get home that very same day. So if I want world class healthcare to go to the airport or to try some sort of new ethnic food, I can do all of those things. But Hudson valley is really a creative space. And so if you come up here, you're going to find a lot of these people on their second mountain, right?
Entrepreneurs who are now running a coffee shop, you know, VCs who are now coaching high performers, like they're kind of finding that [00:31:00] second mountain of theirs. And it's cool to be around people who are in what I'm kind of calling their second mountain, which is they're happy. They're excited. They're joyous instead of being like ground down, stressed out.
And so this environment is really great for that. Now, add to that, it's beautiful, has great food, the produce is excellent, the hiking is world class. Like, it's just a great area. I love it.
Geoff Roberts: Yeah, I, I grew up in New England and, I mean, spent tons of time in the mountains in Vermont, New Hampshire, and Maine, and last year when we had lunch was really my first time in the Hudson Valley area, and I was blown away.
Very impressed at how beautiful it was, how nice it was. I feel like it's, it's flying under the radar even still.
Justin Welsh: Yeah. And, and where you and I had lunch, like that was, you know, 10 minutes from my house and so that's, that's the beauty of the area I live in and I, I don't know. It's great for, it's great for being creative.
Geoff Roberts: This is the time of year to the, the fall is, uh, really tough to be
Justin Welsh: looking good right now.
Geoff Roberts: Yeah. All right. So, you know, from [00:32:00] our, from our conversation also, to be honest, you can feel it more and more in your social media posts. You are, again, kind of maybe encroaching on this point where you're looking for something new and, and something different and something that might come next.
How would you describe generally where you're at and what does that search for what comes next look like today? I
Justin Welsh: would say I'm like, I'm lost and looking to wander a bit. Like, I don't know if you know Paul Millard wrote a great book called The Pathless Path. And I don't remember if it's his words, so I don't want to misattribute it to him.
Um, But he makes me think of it, which is like this idea of sort of wandering and kind of allowing yourself to be exposed to many different things of interest. And so I'm still full force ahead of my business. I love running my business. I love running my business less than the outcomes I like getting for people, right?
Like, okay. As you know, as I told you, I have a five year shelf life. Like I, I definitely at some point would like to do something new, but like what gets [00:33:00] me coming back is I get about five emails a day of people are like, I worked at this job and then I built my own business using your stuff. And like, I'm just made my first a hundred grand and I'm so excited.
And like, that stuff keeps me going. That's like the fuel to this. Sort of five year shelf life fire that I'm trying to like, keep burning. Right. Is like the fuel that I get from other people telling me that I was in some way, shape, or form helpful. But I do think like in the next two years, I'll probably wander a little bit.
I'll probably take a sabbatical, expose myself to a bunch of interesting and creative projects that are probably hyper local here in the Hudson Valley. My wife and I don't have children. So the community is sort of our next big thing. I want to invest in the area that I'm living in. And so part of me is like, how can I be a better member of this community?
And I think just simply by exposing myself to a bunch of different opportunities here in the Hudson Valley, what will probably happen is I'll get excited about something. And then the old, like, how do I turn this into a business? We'll, we'll start to happen. And that could be a really cool [00:34:00] sort of next chapter.
It also might not happen. One thing that I have that I'm happy that I have is confidence in myself. That like If two years went by and I didn't find anything and I needed to get a job or partner with a friend and build something else, like I'm pretty confident that I could do that. And so I don't feel any panic around that.
Geoff Roberts: Awesome. You have a, you know, you said you're in a bit of a wandering stage. Maybe I know that you've done a bit of wandering over the last year or two. And just in terms of traveling, you know, I'm an avid traveler. Tell me, tell me somewhere you've been that made an impression that you really loved.
Justin Welsh: Hmm, it's a really good one.
Surprisingly, I went to Italy for the first time. I had never been to Italy. Tuscany made a huge impression on me. I thought it was far and away the most visually stunning place that I had been for no reason other than I thought the flowers and the rolling hills were just incredible. I love that and like a favorite of [00:35:00] mine, which I've been to now 12 times, I think is Mexico City.
That's like, okay, that's my probably one of my favorite places to go just from an experience that It's just so distinctly different from what I had stereotyped it as and was afraid to go quite candidly back in 2017 or 16 when I first went and had such a good time that like I've brought so many people back there and I just really, really enjoy that.
And, and then maybe last but not least is just, I love anywhere in Vermont. I just love it. Okay.
Geoff Roberts: Yeah. It's tough. Vermont's great. My sister lives there. I spent tons of time there growing up, but. Mexico city, it's got to be at like the very top of my list. Now it's a place I've never been. Everybody keeps singing the same song that you're singing here.
So I, I got to get myself there.
Justin Welsh: Cool. If you ever want to go, let me know. I've got like multiple pages of documents on where
Geoff Roberts: to
Justin Welsh: go. I appreciate it.
Geoff Roberts: That's all I got for you, Justin. Thanks so much for coming on. We really, really appreciate it. And just appreciate the song that you're singing online and [00:36:00] the motivation that you're, you're giving to other people trying to build their own businesses.
It's really cool to see. So thank you.
Justin Welsh: Yeah, I appreciate that, Jeff. And congrats on the podcast, man. It's always great to chat with you and look forward to catching up again in the future. All right. Take care.
Geoff Roberts: To me, Justin is an awesome example of no matter how much success you have in one field, you can always reinvent yourself and often for the better.
So whether you're climbing your first mountain or your second, I think Justin poses a great question. What can you do to free your calendar of all the clutter and make sure that there's only things on that calendar that you're actually excited to
do.