Choosing Your Risk Portfolio and Finding Your Definition of Success with Daniel Hatke

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Daniel Hatke is an entrepreneur, deep thinker, and friend. I loved this conversation with him because I got to ask him all the questions that I don’t usually have an excuse to ask him.

He has a very unique perspective on entrepreneurship because he’s seen it from multiple sides. He’s lived multiple lives, I guess you could say, even though he’s still relatively young.

He has played the finance CTO Wall Street game as well as the mostly self funded entrepreneur game.

We got to, with that in mind, dig deep into the choices that he’s made to pursue entrepreneurship, how he finds meaning and fulfillment in it, the contrast of his current risk portfolio and stress portfolio against that of his former life in the financial services world, and more!

It was just a great conversation. I’m so excited to bring it to you.

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Software Generated Transcription:

Dan: Daniel, welcome to The Meaning Movement Podcast. So excited to have you here on the show.

Daniel: Absolutely excited to be here too, Dan. It’s a, it’s a, it’s a real honor. Appreciate the invite.

Dan: Love it. The question I’d like to begin with is how do you begin to talk about the work that you do?

Daniel: Um, I talk about it in terms of, uh, entrepreneurship through acquisition, um, that, you know, kind of. Key word or words, um, has gotten more and more steam and more and more popularity in the past, I don’t know, three, five years. And, um, I was lucky to sort of stumble into it, thought it was a cool idea, and, um, And went down that rabbit hole and, um, have acquired one business so far.

And we are continuing to look. Um, but we’re, we’re picky. And I only do it with my own money, so it’s not like, uh, we’re on a big spree. It’s more, um, I talk about it in terms of, um, building a family of small family businesses.

Dan: A family of families. I love it. Um, what, what types of businesses?

Daniel: e-commerce specifically. So we, we have two e-commerce businesses. One, one is more the, the real, uh, operating business, um, right now, and it’s in the sports nutrition, sports nutrition space. So we do pre-workout, post-work, amino acids, that sort of thing. And it’s been really fun. Uh, it’s a, it’s a tiny little company.

Um, it’s just my wife and I run it together and, uh, it’s taught us a lot. We continue to learn. We continue to make mistakes and iterate and, uh, we’ve got some of the best customers in the world.

Dan: I love that. So, great. So I wanna just rewind and just ask the question, like, how did, how did you get into this, you know, this corner of entrepreneurship? And, um, maybe, but maybe I, I wanna maybe ask the question, um, what, tell me like the history of your relationship with being an entrepreneur of, of that piece of your identity.

Daniel: Yeah, that’s interesting. Um, I still wrestle with even being able to have the privilege of calling myself an entrepreneur, right? Like, um,

you know, I hadn’t, I haven’t, I, you know, I didn’t start this business. I, I bought it off of a, a few guys that, um, that are true entrepreneurs and built this cool, cool little business that I now have the pleasure of running.

Dan: Yeah.

Daniel: But how I ended up stumbling into it was, uh, through graduate school actually. So I went to business school and there there is a concept called search funds. Um, and also a thing that’s gotten a lot more steam recently, but, um, It used to be sort of in the confines of, you know, Harvard, Stanford, Wharton kind of thing.

Um, but that’s where I got introduced the idea. Uh, so I kind of explored raising money and trying to find a business to buy. Uh, then I realized more of who I am and who I want to, how I want to live, um, is have more control and more flexibility in my life. And doing it alone was going to be, A much smaller game.

Um, but it was going to be able to afford me some of the things that I wanted that weren’t just money. So that’s, that’s sort of what drove me in that direction and, and that that catalyst of finding the idea, uh, happened to BE’S goal.

Dan: I love it. I love it. Can you just contrast with, for me, you know, for folks who are maybe kinda less familiar with the world, like, uh, with this world, not the world in general, right. , um, uh, like contrast a little bit. Like, cause it feels like a very clear decision to be like, okay, I’m not gonna go that traditional route and.

Like you said, like it’s a, you want a different lifestyle and there’s a trade off there, and so maybe could you contrast that choice, like what your life looks like now versus what it would possibly have looked like if you had gone down that path?

Daniel: Yeah. So, um, my past is in financial services, uh, on the technology side of things. So, um, this is a world where, Some of the things you see on TV are true, most of them aren’t. But, um, it’s filled with incredibly bright, driven people. And, um, if you wanna be, if you wanna have the pleasure of working in that industry, you, you have to be all of those things and show up and be there a lot.

I loved it for the time in my life that I did it. Um, but I also, you know, there was a point where if I wanna have a family and I wanna see the kids more than. hours Monday through Friday, um, I was gonna have to make changes. Right. And, uh, so that’s the main, that’s the main catalyst that, I mean, that’s the main reason or push for me to have explored different ways of doing things and sort of bucking the trend of more and more.

Dan: Yeah. I love that. Um, I mean, I think like that’s such a necessary trend to to, can you say to Buck, that’s not how we usually use that phrase, but, but uh, like

Daniel: Well, it’s a

terrible, it’s a terribly tough balance, right? Like, uh, and also like you can step out on your own and find yourself working even more. Um, Because the buck stops here kind of thing, right? Like, I’ve gotta put food on the table. I’m not a w2, I can’t just collect the paycheck. Um, so there’s, there’s added stress.

There’s no, there’s no, like, this is the way everyone should do it this way. It’s more, um, I thought I had some skills and some ability to go do this and it’s worked in my favor so far. That doesn’t mean it will always work in my favor. Um, S you know, I, yeah, I took the dive. I’ve loved it so far and I hope I continue loving it.


but for the, for,

Dan: glad, you did. Do you ever have, do you ever have those nights when and when you’re like, did I make the wrong choice?

Daniel: um, , well, obviously

Dan: I say nights. I say nights because I, I wake up at 3:00 AM sometimes and I’m like, what am I doing with my life? Did I, where did the last 10 years go? You know? Um,

Daniel: There’s that, or like a terribly large unexpected expense or, um, looking at the past two years, a huge shift in the world, uh, that you can’t plan for or, um, try to get ahead of, and you just find yourself, uh, in a very different situation than, than what you had imagined for yourself. Um, and that’s, that’s definitely a situation that we’re, that we’re in now.

But, um, you know, we, you, you just, Keep at it

Dan: Yeah.

Daniel: as you, as you would with, I mean, you know, if you have a regular job, you could get fired tomorrow.

Dan: Yes.

Daniel: Uh, so there, it doesn’t matter, uh, which route you go, there’s gonna be challenges and it’s more about how you, how you react to them and, and how you think about them and how you talk to yourself about them, um, to get through it.

Dan: I love it. I love it. Um, I, I just think it’s such a good, such a good point that like there’s, there’s always risk and it’s easy to point at, you know, the W2 and the, the, the, the Capital J job.

Daniel: Yeah, there’s an

Dan: say that that’s safe, right? Yeah. Yeah. And to say that it’s safe or more reliable or, or whatever might be the case when the reality is it’s just a different set of risks.

And so you just kinda have to choose, choose the risks that you’re willing to tolerate, in my opinion.

Daniel: Risks that you’re willing to tolerate or what sort of mission that you’re on in this particular season in your life and um, and what plans you have for the next season kind of thing.

Dan: Yeah. Yeah. I love that. Um, I think of. The financial services space and like as you’re talking about, you know, the, the, you know, Stanford and like these, you know, the, the nba, the NBA , I don’t wanna say like the NBA guys because they’re not just guys, but traditionally, you know,

Daniel: but, uh, yeah.

Dan: yeah, like there’s like a definitely a stereotype there.

And it also, but it feels like, I don’t even know, I don’t even know what my question is around this, but I just wanna get your perspective on it. Like there’s this small. Of extraordinarily wealthy people or people who have this, the right set of skills, the right set of access, the right set of network to become, uh, extraordinarily wealthy.

Um, and they kind of run the world in a lot of ways, um, which I’m not, I don’t think it’s like a conspiracy or like a, maybe an oligarchy or something like that. But, um, I’ve always, you know, since that, that feels very far from my world though, it, I guess, maybe runs parallel in some ways as far as entrepreneurship.

Um, it is a very different path towards entrepreneurship than I’ve been on, which is much more scrappy. Um, emphasis on emphasis on scrappy . Um, and I don’t know, I’ve always just felt like, um, I don’t, I don’t know. I almost wanna say it’s unfair, like the amount of power, um, that, that. Those people have. Um, and there isn’t a question here other than like, I know that you, you brush shoulders with, with that demographic and I’m curious your thoughts on, on that.

Daniel: Yeah, I, I have many of the same thoughts even having been inside the

system. Um, you know, I come from, I come from small town Indiana. Um, I knew one kid in high school that had got accepted to Yale and, um, he didn’t go, um, The Ivy League was not, or even more than just the Ivy League. Those, those schools weren’t sort of even on my radar.


It wasn’t what my family talked about. Um, it wasn’t what I had access to. Um, so I went to, you know, the school in my backyard. It’s a big state school and um, and then, I dunno, I worked a few jobs locally after, after school, and then I had some friends in. Um, they called me up and said, Hey, let’s have you move out here, kind of thing.

Um, so I moved to New York with, uh, carryon. Um, and from there it’s just a string of luck, really. Anybody who’s not, um, citing luck as some portion of, of their successes lying to you or themselves kind of thing. Um, It was a crazy time. Didn’t have a job, didn’t have a plan, had signed up for a rent bill that was, um, you know, three x what my parents’ mortgage was and, uh, just had to, had to make a go of it and was lucky to have found a job in hedge funds. Um, there was a guy that I interviewed with that, you know, to this day I credit him with having taken a chance on me and I ended up getting a great mentor and friend out of it.

Um, worked under him for. Over, over five years. Five years. Um, and, and that’s what got me into this, I don’t know, crazy world called hedge funds that people don’t really understand. Um, and popular culture paints a picture that is not necessarily, um, accurate. Most hedge funds fail. Most of them are tiny. Um, you know, and the ones I worked at, I’ve never worked at a place with more than like 30 people.

Dan: Mm.

Daniel: are tiny businesses. They just happen to have, they manage a bunch of money, but really the business itself is, is rather.

Dan: Mm.

Daniel: Well funded, but small. Uh, and I don’t know from there, like I love the job. It was, like I said, you know, bright, driven, all those things. Um, and super intense big personalities. You don’t get to the top of, you don’t get to go start your own head fund back in those days without, even now, probably without, um, being super type a, driven, networked, all of those things, right. And so then, then came another sort of, how do I call it? Cause I don’t want it to be negative. It’s just like this feeling, it was mostly in my own head of if I wanna be on a different side of this business rather than being a cost center, um, you know, I was the guy making the, the servers work and, um, making sure the data flowed and, you know, all the, all those sorts of things If I wanted to be on another side of the business. It, I felt like, and I was telling myself the story that I too had to go get this kind of pedigree. Um, and which I think is now like in retrospect, a terrible motivation for trying to, uh, spend a lot of money on a

Dan: Yes, We all have our reasons. I could tell you my story of, of, of, you know, but it was what, what needed to happen for me personally at the time,

Daniel: Exactly. Exactly. And that’s still how I look at it. So, um, you know, my experience at B School was, was awesome. Just surrounded by amazing people. Um, all of them doing amazing things and have gone on to continue doing amazing things. And it’s, it’s a fantastic institution. Um, or my feelings of it, having participated in it, right?

And, you know, everyone was super nice and helpful. Um, it was collaborative. All of those things. But, but yeah, I was, I was driven to basically say to those around me like, you don’t think I can do it, but I can. And um, and I did. I got, I got accepted to Columbia. Um, And it was, yeah, it was a absolutely wonderful experience and, and somewhere in between, you know, studying for the GMAT and getting all that ramped up, I, I’d left that first job after five-ish years and, um, became CTO at a different hedge fund.

That was a very, very, very different place from the one that I’d come from, both in terms of like what they invested in and how they invested to the culture. Um, it was just, it was fun to, I don’t know, just take a complete. It wasn’t a 180, but it was very different. Um, and again, met a bunch of bright, driven, awesome people and worked for a guy who I still admire today and it was great.

So anyway, that takes us all the way up to sort of like me finishing our experie, my experience with New York and experience with Columbia and experience with hedge funds. And then there’s this kind of, I dunno. Strong, dark, dark line in my timeline.

And, um, after graduating, marrying my wife and then, I don’t know, a few mo a handful of months later, uh, quit everything in New York, packed up boxes.

And then, um, flew to Milan and my wife and I traveled for a year, uh, which was. A total privilege to be able to do. Um, but that time was what allowed me to sort of put separation between me, my own ambitions, the story that I had been telling myself, um, to find a different story and to be more true to myself and make different choices on, based on different motivations.

And, and that’s it. Like you can see that play out in my life.

Dan: Wow. Um, yeah, maybe. I mean, I love everything that you just said and thank you so much for sharing, you know, so much of, of your story. Um, I’m curious just about like the, like the, the story this, you mentioned, the story that you, you were telling yourself and how that, how that shifted. Could you contrast those two stories for us?

Daniel: yeah. Um, You know, I, I didn’t, I didn’t grow up in, um, a moneyed environment. We didn’t do poorly. Um, but my parents both worked hard for what we had. And, um, and I wanted to work hard too, but I wanted to make more.

Dan: Mm.

Daniel: That got, that was, that got put in my brain somewhere very early. Um, and moving to New York and. I had a fun job and you know, I was definitely on the side of the business that, um, didn’t make gobs and gobs of money, but it was New York City and money’s different there. And, um, I did okay and, uh, and I was very motivated by that. Um, and that story hadn’t changed or really updated. Right. Um, so. Given two different opportunities. And this is, this is kind of, this is kind of a real, um, a real moment that that happened to me. Um, being on an interview doing well and being told what the offer would be from a company that was exploratory and curious and um, was more creating content and doing some consulting. It would’ve been a really fascinating.

And I think I would’ve learned a lot, but it would’ve been a pretty significant pay cut. And, um, I didn’t take it cuz that’s the, you know, the track that I was on and what I was motivated by. Right. And, um, and I still clearly, I, I remember that moment. I, I still think about it. Um,

Dan: Mm

Daniel: and, and I don’t know, you just, you have to be more, uh, It’s a privilege to be more honest with yourself, but also just try to be more honest with yourself.

Right. Um, so those seeds have been sewn at some point. I knew it but didn’t know it. And, um, yeah, I, you know, I don’t, it’s, it’s sometime during that year off where

Dan: Yeah.

Daniel: I didn’t imagine myself wanting to go back and doing hour long commutes and, um, and being in the office. Seven to seven or more. Right. Um, yeah, I don’t

know. That’s

that’s kind of where, yeah.

Dan: Do you feel like it was just like your experience of life outside of the office that caused that shift to happen? Or was it like, it, it feels like something in you kind of, uh, I don’t wanna say woke up, but like there’s your lens changed and, um, what invited that change for you?

Daniel: Yeah. Um, I, I don’t know how else to say it other than being more honest with myself, right. Like, I think, and that’s why I tell the story about the, the, that one, that one interview, that one piece of, another piece of luck that I didn’t chase, right. Um, Because that shows that at that time in my life, I wasn’t necessarily being honest with myself. And at some point I, you know, like you said, woke up, right? Like I started listening or there were other things that were more important. And I started actually giving them the chance to have priority rather than saying, you know, of, of these five, 10, whatever things, um, I’m focused on this one right now.

Um, and trying to open up that portfolio a little bit. Where, where do I want to go? Why, um, what meaning is there, um, what are your motivations? What’s, what does an end goal look like?

Dan: Yeah.

Daniel: And, you know, listen, I still don’t have answers to many of those things, but

Dan: Yeah, but, but

Daniel: you’re, they’re being updated daily,

Dan: I love that update. I mean, you said like that your story hadn’t updated and it just kind of, I just remind me of, you know, I, I, I have a Mac and I’ll get like, you know, a new update. You click the button, it downloads and like sometimes. Stuff happens and you don’t really see it a lot, but then like over time, like things change, it’s like, oh, there’s a new icon there.

Or they’re like, oh, there’s like, I don’t know, there’s new features or whatever that like, um, I thought it’s just a really great way to think about like our, the stories that we tell ourselves, like, um, that one, they should be updated, you know, intentionally revisited and, and asked like, is this the story that we want to be choosing to follow or, or, or, you know, guide our lives in accordance with.

But then two, You just to kind of take, take stock of like, okay, the story has updated, but is my reality. Does my reality match? Um, match the story? And um, so I think it’s just a really, a fun metaphor to kind of play with.

Daniel: Yeah. Yeah, totally. And there was um, uh, a book that my brother gave me recently. It’s called, Chatter by Ethan Cross. I think he’s a professor at Michigan or something like that. And he talks about like the stories that we tell ourselves, the, the way we talk to ourselves, right? Um, and I only read this recently, but I can imagine like if I had, um, read the book a long time ago or something changing the, I, I’m being able or more empowered to make some of these changes earlier.

Dan: mm-hmm. Yeah.

Daniel: And because he talks about like addressing yourself in the third person, that’s the main

idea to take away from the book, is addressing your in your own thoughts when you’re talking to yourself, addressing yourself in the third person, separating yourself for a little bit. And it allows you to be able to, um, be separate from oneself.

But really, like many of us are really good at giving our friends advice.

Dan: Mm-hmm.

Daniel: But we’re not necessarily good at giving ourselves advice. Right. And this technique kind of helps that a little bit because then you can go and talk to yourself in a completely different way, and it’s pretty cool.

Dan: I love it. I love it. I had, um, I’m, I’m blanking on his name. He’s a running, a running coach on the show, which is great for me to, to geek out, out about running. Um, but he’s, he’s talking about this idea and, and some of the self talk, cause I asked him like the question like, how much of running is actually just mental versus like, your body, you know, and he’s like, oh, it’s like 90%.

I mean, you can’t like, put aside the body, but. But he, he, he was stating that like, so just some of the mental game of running and, and, um, like that third person piece, which I had never heard before. So it’s the second time that that’s been point out. And he also said like, talking to yourself out loud and saying your, your own name, addressing yourself in the third person out loud takes those stories, takes the things that you’re saying and just it gives you more, gives them more power, more weight, um, which is just really, really fascinating stuff.

So I love it. I love

Daniel: yeah. It’s cool. I mean, yeah, I wouldn’t, you know, you could do that. Um, walking down my little suburban street and people are probably thinking You’re crazy. But on the streets of New York, New York City, it’s just, you know, it’s fine.

Dan: well just keep your, keep your earbuds in and they’ll just think you’re on the phone.

Daniel: that’s, yeah. We’ve all got covered now.

Dan: Yeah. Yeah. And everybody’s crazy I love it.

Dan: Uh, I’m, I’m curious just about, you know, that the end goal, and I know you, you don’t, you don’t, You know,

Daniel: Yeah, I dunno,

Dan: to say you don’t, you don’t know,

Daniel: paint a picture.

Dan: yeah, but what do you, what do you know?

Daniel: Um, what I know is that I wanna keep this flexibility. I wanna be a present father and husband. Those are super top priorities for me. Um, I’ve got a daughter that’s almost two and a son on the way. And, and those things are, Really important to me. Um, but I also know that I have to provide for them.

Um, I wanna be able to pay for the college if college is still a thing

16 years from now. Um, and, you know, all that goes with it, right? And, and I’m, you know, happily admit that like, I like nice things and you know, all the, all the stuff, right? So it’s, um, I wanna do well by, by myself and by my family.

Dan: Hmm.

Daniel: But in order to do that, I look at it in terms of instead of, instead of just looking at, you know, your W2 and saying like, I make a bo load of money because I work really hard and I’m never around more, just a bunch of different income streams.

Slowly build them up, pay attention to them, you know, water, the flowers if you will, and um, and do right by customers and clients and all that sort of thing in order to. Provide value. Um, I’m in the business of providing value to, to people and um, as long as that is working, they should stick around. We should have revenue, we should be able to keep the lights on.

And if there’s, you know, extra money left over and we keep our lifestyles as mini reasonable, but you know, don’t let them

inflate. Yeah. Then, um, then we should be able to turn some of that extra cash into assets and the assets will appreciate and, you know, but,

Dan: Yeah.

Daniel: To me, I, in my mind, this is super simple and I understand that it’s like gonna take years and lots of work.

And to some people it’s not simple or they haven’t been exposed to these ideas. Um, and that’s one of the things that a friend of mine and I are trying to work on is like exposing more people to these ideas. Um, so the people feel that they can enable themselves, right? Even if, I don’t care how much you make, right?

If you’re able to sock away some extra.

Dan: Yeah.

Daniel: things that you can do with that money. Um, and you also might find some fulfillment in it, right through different, you know, creativity or you know, that like say you do well and you’re like, this thing that I’m gonna buy every dollar it makes is gonna go straight to this charity I care about a lot.

That’s something like,

there’s no wrong answers.

Dan: Yes.

Daniel: Find ways to do it and, um, the pie just, you know, it’s not static. You can, the pie can be grown. So, um, I dunno that, that paints the picture of the path, maybe, um, where it ends up. Who knows, you know?

Dan: Yeah. Yeah. I love it. It’s like, uh, it’s like you can see the pie, the pie tin, and you’ve got like a couple slices in place and you’re just kind of filling out the rest of the pie

Daniel: some apples in the backyard. We

Dan: Yeah. Yeah.

Daniel: Yeah.

Dan: That’s a good way to think of it. I know where the trees are, at least then I can go pick the apples from, just gotta figure out to get there.

So. That’s, that’s so good. So good. Um, I know we’ve talked, we’ve talked about some of my framework of, of the four piece, um, which are, you know, the people, the process, the product, the profit, and, you know, so I’m always using that lens as I’m engaging with people’s stories and, um, I, I hear that very present in I think, some of that shift in your, in your life.

Um, but I’m curious just how I know you’ve, you’ve been kind of thinking through that framework a little bit. Um, curious to hear some of your reflections on, on those four areas.

Daniel: Yeah, I mean, I thought it was a really useful way to think about all these things, um, because those are, those are the main drivers. Right. You know, I wrote some notes down just to make sure that like, I’m thinking about some of the things that have happened to me and, um, you know, going back to that like stark line in my timeline, right?

There’s, there’s, there’s the before and there’s the after and, and thinking about that four P framework, the, you know, the stories and the things that I wrote down are very different from, there’s things that relate to one another, but they’re very different. Um, but you know, I thought about the process part in my prior life because there were things that like, you know, day to day, like I got to do interesting things, right?

Like we had a budget. I got to buy big pieces of equipment and make new cool things happen for the business that made everyone’s lives better, their productivity higher. They were able to spend more time thinking about things that mattered rather than moving numbers around for, because there was no better way to do it, that sort of stuff.

Right? And um, so I was always driven by that. That was always a lot of fun. But I also, I really did a good crisis and, um, and there were, there were no shortages of crisis crises. of them imagined, but some of them are real. Uh, one of the places I worked at, we, I don’t know, we were 15 yards off the Hudson River and when Hurricane Sandy came in,

uh, you know, our whole first floor was on three feet of water and our server room was where.

Dan: Oh no.

Daniel: Um, and, you know, the market shut down. So we were fine for a little bit, but like, it was supposed to open on Wednesday or something like that. So, you know, I’m standing in water, we’re doing extension cords and moving servers up and um, but you know, in, in a good crisis you see people coming to play ball, team players come out, creativity goes up, you gotta solve problems.

Um, so those are things I really enjoyed. Luckily, there’s not a lot of crisis in my life now. They’re mostly dull and frustrating rather than those sort of acute,

uh, sense heightening experiences. Um, but then, yeah, I, uh, and, and then people, the pe like something I struggle with now is sort of not being alone, but like it’s my wife.

If there’s no other coworkers, right? I don’t go to an office and like, talk about the latest TV show. Like there’s a, there’s an aspect of social life that compounded by Covid. Um, you know, the world kind of got small and it’s getting better, but like, um, our life just looks different. Plus we had a baby.

Like, there’s so many

reasons, but, um, yeah.

Dan: is a, it’s a recipe for, a recipe for loneliness.

Daniel: Yeah. So that’s like the, the people side of it now is like less amazing. But, but in my past life it was amazing. I, I, I’ve worked with amazing people and, um, and I should do a better job of keeping in touch with them. That’s, that’s the thing that’s popping into my head now, but, um,

Dan: I mean, the flip side of that is you do spend time with your wife and your daughter that you otherwise wouldn’t, so there’s

Daniel: yes.

Dan: trade off there. Yeah,

Daniel: a trade off and we’ve already talked about it. Like

what, what way I went, uh, on that and I don’t, no regrets there. It’s just some, you gotta spend time reflecting on some of these things, right? Making sure that, you know, if my cup isn’t at least half full, then I’m probably not bringing my best game to my family too.

So like there’s, you know, trade offs no matter what you do and you just gotta. You know, do your, continue to do your best. Um, but then, you know, now it’s definitely, you know, my life is more driven by like product and profit. Um, and I really like the way you talked about profit too, because people hear profit and that, and immediately it’s just a dollar sign.


Dan: Yeah.

Daniel: And, um, if I had continued chasing the life that I had been living, profit would probably be higher in the, in the dollar sign category. But now I have tons of flexibility and I get to do, you know, my in-law’s flying to town, we hang out. Um, I, you know, fly to hang out with my parents. We unfortunately don’t live near either sides of our family.

So those sorts of moments are important to me in two weeks. Vacation is not gonna cut it. Um, for how many times I will likely be able to see my parents in person for the rest of my life, right?

Dan: It’s

Daniel: so those. That’s a, you know, I keep coming back to it. It’s clearly an important piece. Um, but then, yeah, concentrate on making sure that our current businesses and any future businesses that we acquire are providing value.

They aren’t just churning more junk into the world. That’s, that’s another guiding principle for us. Um, as part of, you know, that’s inside your f.

Dan: I love it. Really, really great analysis. Thank you. Yeah, thank you for that. I’m curious as you’re, um, and you can tell me if this is a true contrast, but I’m just thinking of you, you know, being, going from the hedge fund life to, to the, you know, the acquisition entrepreneur life and, um, like it feels. It could, could be a movement towards, and I already, I already used the word scrap scrappy entrepreneurship to, to describe myself.

Um, I’m curious, I’m curious if that’s, if that feels true of your, of your transition as well. Like, do you feel like you’ve had to get more scrappy

Daniel: Yeah, a hundred

Dan: and, and, and Is that hard? Is it hard to move that direction? Cause I feel like a lot of people try to go the other direction.

Daniel: That’s true. Yeah. I mean the, uh, there is an ease to the other direction, right? Like, going back to like, I had. Fun at my job. Cause I had a budget, I could go buy nice things that provided value to, to my clients, my fellow employees. Right. Um, and it feels great to be able to do that.

And it also feels great to like buy the thing that, you know is gonna work,

Dan: Yeah.

Daniel: set it up and deploy it. Right. Um, whereas now it’s totally different. Like there’s not a budget for anything. Um, I have a ton of ideas and no money to go chase them. So it’s, it’s finding ways to be able to push that ball with as minimal dollar input as possible.

Um, And, you know, I’m clearly not the TikTok influencer type, uh, or you know, great. Yeah, yeah, yeah. great at self promotion and all those sorts of things. But like, I, I now have a way better under, like, way bigger appreciation for those, the, the kinds of people who are able to, to drum up audiences out of thin air.

Right. Um, and they don’t have to pay $2 and 60 cents per click to Google. You know, there’s, there’s some heavy costs in trying to get in front of people. Um, but anyway, you learn and you try and, um, and, and the thing that I’m constantly trying to work on myself and tell myself is to not get down about the limitations that you currently have and just continue to focus on the opportunities.

Dan: Mm.

Daniel: Because it’s real easy to just be like, well, if I had 20 grand or whatever, whatever that particular project cost, right? Um, uh, yeah, really easy to just sort of like throw in the towel right there and say like, well, I’ll get there,

but there might be otherwise.

Dan: Mm, that’s so good. And talk to me about, um, like how do you wrestle with, uh, Like, I dunno, I discouragement the loneliness of entrepreneurship. Like the, the like being like when there’s a problem or when something’s not working in the business and it’s. It’s just you and your wife. Like, I don’t know, I, I’m just curious how, um, this is, this is a selfish question.

This is Dan. This is the Dan, the Dan Cumberland self-help hour. Welcome. Welcome everyone. . Cause this is just a question for me cuz it’s something I do struggle with and it’s like, man, things are not clicking right now and I’ve gotta figure this out. And I mean, like, I know that that’s life to some degree.

Um, but it’s also very acute when it’s entrepreneurship and. Literal families, you know, uh, happiness, not happiness, but health and, and safety

Daniel: Bread on the table.

Dan: everything. Yeah. Um, I’m, I’m curious. Yeah. Just how

Daniel: Uh, it’s a total, it’s a total struggle, um, struggle here too. There are, um, dark days, moments, streaks, weeks, you know, they happen. Um, and my wife can attest to that. Um, there’s, I mean, the most important part is we have a super strong relationship. We’re super open and honest with each other. Um, the other thing that I think that I have. Speaking of luck again, uh, lucked into is she’s from an entrepreneurial family and there are certain aspects of this life that are already sort of baked into her normal. Um, whereas I can imagine if it wasn’t, this would be even a bigger, bigger

struggle. Um, so there’s that, there’s a baseline there of that.

I’m just lucky to.

Dan: Yeah,

Daniel: outside of that, yeah. Go back to that book or that the, the talking to yourself. Bit going nice long walks when the sun’s shining here in Seattle.


Dan: Exercise. Get it out

Daniel: exercise, uh, get out of the rain and gray at some point during the winter. That’s tough on me. Um,

Dan: same.

Daniel: But yeah, I don’t know.

There’s no, you know, I hear you and I, um, I empathize

Dan: Yeah,

Daniel: it’s, it’s the same. Um, and there’s no Yeah, no right answer, but it’s finding your, your toolkit to go find space or find ways to sort of get yourself out of any of those doldrums.

Dan: yeah. I appreciate that. And um, yeah, I think just what you said about, about your wife just. Makes it, makes a lot of sense. And I think, you know, my, my wife’s not from an entrepreneur family, but her, her, her dad is a pastor, which is not, not an entrepreneur, but like, she’s very used to like living a minimal life.

And that’s like, so, so being scrappy with our, with our household budget and things like that when necessary, like is. You have that support. And I think that’s the, I think the bigger piece is just having, having a partner in life that, um, understands your goals and is on board with them is, I don’t think that, I don’t think I could do it otherwise.

Um, because it takes, it takes a toll in the family, um, that you both have to be on board with. So, um, so yeah.

Daniel: I’m gonna, I’m gonna turn it around on you a little bit. So like, let’s say Dan Cumberland hits a huge, and not huge, not like, um, you know, sell Instagram for whatever it’s sold for.

Huge. But like, you know, you end up doing extremely well and your kids, um, You know, are some years ahead of where they currently are and they now live a completely different life.

Li Diff different than how you and Sta grew up, how you’re living currently. How do you, do you think about how you would instill some of those values Well and perspectives in them, even if the world, their immediate world around them shifted.

Dan: Yeah, that’s really interesting. Like if they had all the resources and more that they could ever want, how would I, how would we teach them to be, to be scrappy? Um, yeah. I honest.

Daniel: I mean, to be scrappy is one thing, but also just to, to recognize that, That there’s multiple ways of living, growing. Um, our way isn’t the only way. Um, things were different for us at one point. I don’t know. It’s so, it’s so ephemeral because

Dan: Great.

Daniel: their world is so, you know, small up into a certain age.

Dan: Yes, yes. I, I do think about it. Um, I mean, one of my goals, you know, financially, which is it’s just one piece of the puzzle, but, um, is, you know, I want, I want them to be able to have a safety net where they can take the risks that they want to take, um, in life. Whether that means, you know, go, go into grad school or if it means, um, uh, Bec being an entrepreneur and starting something or, or whatever.

Like I’ve, I’ve found, you know, just so much, there’s so much flexibility that comes from that and a piece of that. And I think some of it is financial literacy. It’s some, some somewhat similar to what I think what you’re talking about with, you know, with your friend and doing some education around is like, by learning to live with less and being okay with less, you. Open yourself up to more possibilities than you otherwise would be available to you. Because, because your burn rate, you know, your, your, your monthly budget is, is so much lower. It it takes a lot less to, to, to hit those hit, hit those goals. And so then you can experiment and try different things. And I think that my hope would be that.

I could teach them that piece. Cause I think, I think that’s a big, a big part of it. And then beyond that, as far as like, I think the identity piece of are, are we entrepreneurs or are we W two? You know, like, I’m not as concerned about that. Um, I want, I mean, I, I’d love for them to be entrepreneurial. I think that, um, there’s a mindset that comes along with that.

But whether they’re doing that in a job, Outside of a job, it, it doesn’t concern me as much. I just, I, I just hope that I’m raising kids that are, um, that understand that like, change in the world only happens if they, if they keep their hands on the steering wheel and, and, you know, drive, drive, drive their life where they want it to go.


Daniel: Hundred percent.

Dan: yeah, those are some of my

Daniel: Exercising some of their own control and showing them that they have,

they have power.

Dan: control. Yeah. And I think that that’s a big piece

Daniel: feeling like they don’t.

Dan: Yes, yes. And we can, we can talk more about this, you know, um, off offline, but like some of the decisions we’re making around school and like, um, my oldest is in a, we, we started him in, in a hybrid, like homeschool public school.

It’s a public school program, but it’s, it’s part homeschooled. And so it’s a college schedule and just how much more freedom he has over his time, which I think is like, I, I’m really excited for him to not just be, uh, experie. Not that there’s anything wrong with the classroom, with public school or whatever, but there is this bit of mentality of like, you just give your time.

You just do your time and.

Daniel: And then the check boxes are.

Dan: Yeah. Yeah. And that’s not necessarily the way that, like, that’s not how my life works. That’s not how your life works as we’ve already spoken to. Right? Like, there’s other ways that we, we check the boxes, um, and sometimes it takes more time. Sometimes it takes less time. Um, but to have that kind of built in to the mindset part of, of, of his schooling, um, Of his day in, day out routine.

I’m really, I’m really excited and hopeful, you know about that. We’ll see, we’ll see how it goes. We’ve just, we’ve just like a, a weekend so, uh, ,

Daniel: week. Yeah, that’s what I was wondering. Yeah,

Dan: but, uh, but I’m hopeful,

Daniel: That’s cool. I really like that idea though. There was some school that we, uh, she and I were looking at and um, it had something to do with like a week off every month, but the go year round, it was, again, we have baked flexibility into our lives. I don’t need a three month summer.

Right. Like, so it was an interest.

Dan: yeah,

Daniel: Um, little bug that got planted on our brain.

Dan: yeah. It sounds like a cool model. I love it. I love it. Well, this has been just super fun, Daniel. I know we can, um, Yeah, go on. Go on indefinitely. And we will, I know

Daniel: yeah. we will.

Dan: it, but, but

Daniel: Kids will be running around us at the

time though, so , I’ll be chasing mine with a potty. Yeah.

Dan: Yeah. Oh boy. We’re, we’re always, always, always tripping over potties, in our house. Um, for folks that wanna, uh, folks that wanna follow along with you, connect with you, is there anything that you’d like to invite people?

Daniel: Yeah, sure. Like I don’t have a huge footprint, but, um, you know, I, I, I love Twitter. I’m mostly a listener, but, uh, my handle’s Daniel Hake, d a n i e l h a t k e. You can find me there, you know, I’m on LinkedIn and, um, you know, anybody ever reaches out, I’m happy to reply.

Dan: I love it. Thank you so much, Daniel. It’s been really fun to, to connect here.

Daniel: Thank you.

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