Personal Finance for Entrepreneurs | Elliott Zelinskas | DS637

October 05, 2026 • 00:24:43
Personal Finance for Entrepreneurs | Elliott Zelinskas | DS637
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Personal Finance for Entrepreneurs | Elliott Zelinskas | DS637

Oct 05 2026 | 00:24:43

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Show Notes

Elliott and I geek out on personal finance, saving, and early retirement. Not financial or legal advice, talk to professionals.

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00:00 Personal Finance Kickoff

01:06 Early Money Lessons

03:53 First Investing Wins

07:29 Accounts and Simple Portfolio

10:22 Work Versus Jobbing

17:03 Spending Money Struggles

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Episode Transcript

[00:00:00] Doug: Hey, what's going on? Welcome to The Doug Show. I'm Doug Cunnington, and Elliot Zelinsky is hanging out with me again. How are you today? [00:00:08] Elliott Z: What up, Doug? I'm good. Thanks for [00:00:10] Doug: Yeah, really cool to, uh, catch up with you in the last, uh, few minutes. We've-- we're recording two straight here, but I want to talk about personal finance. It's a hobby and interest for both of us, and I got in deep, um, over the last few years. My wife and I retired early, and it's been pretty fun. A-actu- it's been a huge blast. I, I don't wanna undersell it. It's fucking awesome for me, and I think some people are like, "I don't know if I wanna retire early. I wanna be more productive." I mean, it's not like you have to stop doing everything. It's just, like, you could choose what you wanna do or take a break or whatever. But I don't know much about, like, your background in personal finance, your overall goals and stuff like that, and we're just gonna kinda go back and forth. And feel free, Elliot, to ask me questions along the way here. But yeah, what's your story with personal finance? Did you get into it, like, as a kid and that kind of thing? Early Money Lessons --- [00:01:06] Elliott Z: Totally. I was in large part raised by my grandparents, and by the time that I was, like, not a little kid, my grandpa was retired. And because I spent so much time at my grandparents', I sort of sat on the couch with my grandpa while he just read The Wall Street Journal and, like, watched the news basically on mute, but he would just read the ticker symbols for hours. And I just, I, you know, I was really close with my grandpa, so I just sat there. And I would be like, "What's this? What's that?" And he literally just, like, gave me a mega education on kind of investing and personal finance and things like that. And, um, so that's, like, definitely where it began, and he had, like, a very stoic, logical way of thinking. And so I sort of take his mentality. And then when I was in college, I was coming home from a skateboard trip from Arizona, and I was at the airport, and I was early to my flight, so I walked into the bookstore, and randomly I found this book called How to Live Well On Less by a guy named Fred Brock. And I don't know why, but title just really resonated with me, and I bought it and then read it just in one sitting, like, at the airport and on the flight. And it was just like, oh my God, like, I had never read a personal finance book or like that, but for whatever reason, I was just super entranced by what he was saying. He and his wife used to live in New York City, and he worked for The New York Times. And then once they retired, Fred was like, "Why are we paying so much? We're retired. We don't even need to be here in New York. We love it, but our dollar can stretch further." I think they moved to Ohio, I was just like, you know, it just broke down, like, how important cost of living is, especially, like, your monthly burn. And I feel like I had a good base, a foundation. And then from that, I mean, I've read, I think, nearly all of the, you know, personal finance books. I mean, that's a big statement, but I've read a lot of them. And, and I did this in my 20s. I started investing as soon as I graduated college. Uh, right after I got my first job, I think my my first job was, it's called a paraprofessional, so it's like a teacher's assistant. And I was living in San Francisco as a teacher's assistant, just, you know, living in the Tenderloin, for anyone who knows where, what that is. Pretty sketchy neighborhood, but that's kind of I like the vibe. And, uh, yeah, and my first paycheck, I just opened up a Vanguard account. I think I was 22 years old, and I've just been dollar-cost averaging basically every month First Investing Wins --- [00:03:53] Doug: How old are you now? Yeah, after about, uh, I don't know, 10 or 15 years, then you're like, "Oh, compound interest is fucking real." Like, is-- Yeah, did, did it kick in around that time where you're like, "Oh, sh- shit"? [00:04:11] Elliott Z: Yeah, at some point, I'm trying to think, it probably was after yeah, probab- it probably was around, like, 10 or 15 years. I was kinda like... I, I remember when I first hit 100K, and then I was like, "Whoa, I feel like I'm totally probably the only one of my skater friends who, like, has this." it's like one of It felt your first, like, six-digit thing in your account. And, and then I feel like after 100K it really starts to [00:04:43] Doug: Yeah And do you know, like, what your savings rate was back then? Just if you happen to remember ballpark, and then what it is, um, now-ish [00:04:58] Elliott Z: Honestly, I do not remember. I wasn't keeping track of my finances like that. I just sort of had enough, and then I would put, you know, maybe like $1,000 in or something. But I, I'm assuming that... I mean, I've just, like, lived so frugally and never even thought about it. I was just... I'm like, you know, like, uh, we mentioned in the f- you know, the last episode before when I was a teacher, like, I didn't own a, you know, a laptop. I didn't even have a phone. When I went to graduate school, my professor was like, "Everyone write your phone number down. We're all gonna take a field trip, so if anything happens, I can call you." And he's like, "Elliot, where's your phone number?" And I was like, "I don't have a phone, dude." And, like, so um, so, like, what I'm saying is, like, I was just, like, a very happy camper with, like, sunshine and a skateboard and, like, living in San Francisco, and I just wasn't spending that much, but, like, not trying at all. Just, like, [00:05:52] Doug: Yeah。 [00:05:53] Elliott Z: uh, so my... I just always had leftover money, and I was like, "I gotta do something with this." And so I kind of read a couple books, and I was like, "Oh, Vanguard index funds, ETFs, okay." And I've just been plugging away since then. But as far as the percentage yeah, I'm not sure. You know, that was n- you know, nearly 18 years ago. But I think these days... Dang, I could do the math. But I think my... Well, know, the percentage I can't really just do in my head, but, you know, if I'm making very solid 15K through these internet ventures a month, I, I think I'd 100% live off less than 2,500 a month these days, but it's probably a [00:06:37] Doug: Got it. Perfect. Yeah, and I mean, it's a thing that some people keep track of. I never kept track. I, I have no idea what it was or is at any point. , The closest I could come is like, well, like I, I think my wife and I roughly made about the same for several years, and I'm pretty sure we were saving like more than like one of our salaries. 'Cause like to your point, like we are-- things got more expensive, inflation and, and whatever, like small amount of lifestyle creep, but largely we kept things in check and, [00:07:11] Elliott Z: Totally. [00:07:11] Doug: and savings rate, some people obsess about it, so okay. Very good. And then, so you started investing, you had a good foundation, read a bunch of finance books, started when you were 22. So that's a huge thing. It's just like if you can stay in the market for a long time, it's probably gonna work out okay. Accounts and Simple Portfolio --- [00:07:29] Doug: do you-- did you have a philosophy around like what you're putting into like a 401or a Roth or post-tax? So, you know, for us personally, at some point we were like, you know, we realize we can, um, get to the money when we're 15, 59 and a half, but that's a little too long, and now I've actually learned that you can get to the money a little bit sooner without penalty. You gotta jump through some hoops, but it is possible. But through ignorance, we just started investing in a brokerage account, which is post-tax. You don't get some of the advantages, but, um, it gives you a large amount of flexibility. So how did it break down for you? Roth, 401, there's like the teacher's, uh, type program, and then post-tax. So talk about that. [00:08:18] Elliott Z: Totally. So as a teacher, I never had a 401, and I always worked at private schools except for a few substitute positions. I actually really believe and love for... I, I love paid education. I think it's, like, something I'm down to pay for, um, and I think it's like... I think it's really cool, I guess, that there's, like, free K through 12, but I think it's kinda crazy. But anyways, I never, I've, I've never had a 401, and so that w- And I always have felt a little bit a- anxious around money, and that's kind of, I think, where my, I don't know, speed in learning about it came from. I was like, "Dude, I'm not gonna have a 401. I work at a private school which doesn't have these kind of public pensions. I need to do, do this on my own." And, uh, so that's how I started. yeah, as far as the accounts go, I probably have about 3% in crypto. I bou- I bought that pretty early on, like maybe 2017, and then dollar cost averaged, like, basically since then. That kind of game is l- pretty crazy but, like I said, it's like 3%. I f- kind of feel like it's crazy to not have anything. But yeah, the majority is Vanguard index funds. Uh, so yeah, I have Roth IRA, and basically I do... And then I have a brokerage, and max out the Roth IRA first and foremost, and then, uh, the brokerage is kind of like a three three-fund portfolio. Just straight up I use VGSH, VTI, and VXUS. And, uh, it's, you know, do pretty much, like, you know, couch potato investing. It's pretty simple. Almost split by thirds, but I have the majority in the total [00:10:01] Doug: . And that's like, the other one is, uh, the international stocks, right? So X is like the non-US, okay. Yeah. Standard, yeah, that's what I have too. So, okay. And [00:10:13] Elliott Z: Yeah [00:10:13] Doug: pretty easy and straightforward. By the way, like, uh, n- this is not financial advice. We're just telling stories here, so, um, very cool. Work Versus Jobbing --- [00:10:22] Doug: Now, the other question is, so you read you know, these finance books. You have a strong interest. And, you know, for me, I didn't really enjoy my job, so like I said, at some point I was like, "All right, I'm not gonna keep working for... As soon as I can get out of this, I'm probably gonna do that." Wasn't as bad as some of my friends who were like, "How can I retire as soon as possible? Like, I'm losing my mind," and they're having, like, uh, some crisis or whatever. For you, was that on the horizon once you, like, started doing the math and you were like, "Oh 4% rule," a couple other things. You're like, I live pretty cheap, and, you know, you're, you're a happy dude, so you don't need as much stuff or whatever. So was that on the horizon where you're like, "Oh, I could actually, like, stop working when I'm, uh, whatever, 40"? [00:11:12] Elliott Z: Definitely not. I think it's crazy to stop working. I don't ever wanna stop working. I just really like it. I like having my hands-on tools, whether that's physical or digital, and I just wanna make things for my whole life. yeah, I mean, I feel like... Well, I feel like I have an entrepreneurial spirit and personality, but I've realized that I h- also have the type of personality that, like, really gets into something pretty hardcore. So yeah, I skateboarded, um, like, every single second that I possibly could since I was, like, the age of literally, like, 4 until, like, 30, and I was... You know, I don't know if I mentioned this in the very first pod, but I, like, grew up, like, as, like, one of these, like, teenage sponsored skateboarders. And, like, it was, like, my... It was my whole life. And so w- I've just learned that whatever I do, get really into it, and I don't... I'm-- I don't do multiple things very well, and I, I just sort of, like... I love working on projects, and so after skating, I did, like, tons of painting, and then once that was... I, but I've always wanted to make money. And so I... anyways, I love, like, the arts, and I just love making things. And then once I picked up the computer, I mean, that actually generates money. That's, like, a magical feedback loop of, like, you make thing that you liked and enjoyed making, and then it makes money. I mean, it's such of a, you know, such a difference from painting or skateboarding or shooting photos, where I, I did all of those things, and I just struggled so hard to make money. And I've always said, like, teaching is the best job if you need a job. But everyone can tell that if you don't need a job, like, the proof is in the pudding. Like, if your job said, "We're gonna stop paying you," would you keep going? The answer is no. Or, like, if your job said, like, "Hey, can you come in on a Saturday and not get paid?" The answer is no. And that's, like, proof to me that, like, your job is probably artificial, and I just can't stand, like, a life wit- that was, like, artificial. That being said, I feel like everyone needs a skill, and m- like, life costs money, so you need to find work. And teaching was a cool job, but it was definitely... I mean, I love teaching. I love teaching anything, at any time, at any place, to anyone, the- anything that I know about. Whether it's, like, in a traditional classroom, or it's, like, on the computer, or it's outside or whatever, I just love teaching. And so I became a teacher, but I so very quickly realized that there's a major difference between education and school. And so I really realized, I was like, "Dude, I want more freedom. I want more money." And the pattern that I continue to see is that everyone that has both of those, those two things, they always use technology. They're always on the computer. And so that's why I bought the computer, and I was like, I just want more independence and, like, more say in, you know, when I go to sleep and when I wake up and where I live and all that good stuff. And so that's really where it came from [00:14:04] Doug: Gotcha. Okay. And the one thing... That all makes sense. I don't, I don't disagree, but just for the interest of, uh, conversation here. So you mentioned, like, you don't ever wanna stop working, and I, I'm-- I actively encourage people, more, more on the corporate side, but I actively encourage people to, like, be less busy, like, don't do as much work, anti-productivity, be lazy. Like, a-and that the thing is, like, I have I'm pretty driven, and I actively have to suppress it, and I'm happier because of it. Now I'm-- I've, like, shifted gears, so my drive is, is less. But what I hear... 'Cause I, I've said it before, I'm like, "Ah, I would wanna keep working, and I'm not-- I'm never gonna stop working," blah, blah, blah. I used... The thing is, as soon as I didn't have to, and as soon as it was a little bit harder, and I was still working for myself, I was just like, "Oh. Oh, I, I actually don't care. I'm not gonna do this work anymore. It's not, not as fun as it was 'cause the result-- it's a little bit harder." So the overall observation is a lot of people that say, "I'm not gonna stop working, I like working," we're self-employed. Like, we're a different animal. Can you differentiate that a little bit? 'Cause obviously, if you're working for someone else and you don't have the autonomy, it's gonna suck a little bit more. [00:15:29] Elliott Z: Totally. I can differentiate that in one sentence. There is a difference between working and jobbing, and I'm not talking [00:15:36] Doug: Got it. Perfect. Great summary. E- And the thing is, like, I, I do some work because I create a podcast, and I've tried to remove as much, um, friction and things that I don't enjoy, so this is, like, a really fun type of work. It's creative, often some collaboration with other people, like the conversation we're having now. So I totally get that, and I'm obviously continuing to, like, work in some capacity, but it's not really revenue-generating anymore, and that is another differentiation [00:16:08] Elliott Z: Absolutely. And, you know, the, maybe the word work isn't even the right word, but it's more like making. Like, projects are really important to me. Like, that's really what I'm talking about. I always wanna be working or making or building things, but in, you know, what's important is, like, it needs to be intrinsically motivating to me. So if not, then it feels more like a job, and yeah, I that [00:16:31] Doug: Yep. intrinsic motivation thing, and that's where, yeah, like even hobbies, it's like sometimes they, they run their course, and then, like, it's not as fun anymore, and you gotta take a break, and maybe you come back to it, and it's always, like, a little thing. But that is an area that, uh, you know, not that I struggle with, but it's like, it's an interesting thing 'cause, like, we should have challenges. We should be doing new things, novelty. There's a lot of different areas that can help your brain stay active when you, when you stop working. Okay. Very good. Spending Money Struggles --- [00:17:03] Doug: I guess the, the last thing that I wanna ask, like, one of my observations in talking to people that did retire early, a lot of times they actually saved a lot more money than what they actually need or can, like, use because they- they're pretty frugal. Like y- you mentioned, you're like, "Ah, I could live off of, you know, X amount." You're pretty happy. They're struggling with, like, not being so frugal a- and sometimes, you know, that's great. It's, it's, um, one of those things. It's, it's a good skill to have, but sometimes it impacts other people. Quick example, it's like you know, at, at dinner, they're like, "Ah, I'm not gonna order this food," and it's like, it just, it costs like $3 more, and you have, like, you know, millions of dollars. Like, it's not gonna matter. You could buy, like, that every single day constantly for every meal, and it actually won't impact anything. So they struggle to spend money. Do you have any fears? 'Cause you're making a lot of money now, and you're spending, like, way less. It's good to, like, build up the nest egg, but do you have any issues with spending money? [00:18:14] Elliott Z: Totally. This is a really hard one for me. I really, really struggle with spending money, and I don't get it. And I-- At the same point, friend of mine who doesn't want kids, who is the same age of, as me, he's actually the dude who gave me his credentials for that original SEO course that we talked about in the first episode. He was like, "Dude," 'cause he and I talk, like, once a month at least about, like, how our businesses are doing. He, he has a business that's doing even better than mine, and he's like, "Dude, Elliot, you have to start spending more money." And I feel like I have a lot more life to live, and I like the optionality, and if I wa-- The thing about me is if I want it, I get it. If I want it, I s- I pay for it. I, I buy it. And I have no problem buying anything that I really want, and I just have absolutely, like, zero budget for anything educational or plane tickets. I travel a lot, and not a lot that really matter to me, but those things have no budget at all. And so, yeah. I mean, I s- yeah, I struggle with buying things that I don't want and I don't need and I don't wanna have, but they're, like, you know, right there. But, you know, a lot of other people would get them. I don't even know an example, but, like... I don't know. If I don't care about it, then I, like-- You can, you can see that in, like, what I buy. And so, man. Yeah, I still... I don't know. It's a weird thing because I'll still, like, shop at thrift stores and, like, secondhand stores even though I could buy, nicer clothes. But the truth is, like, I like going through, like, the racks of clothing and finding the one gem. I li-- I just, I feel like I just happen to be a person who overall... Like, I like, I like cheap bikes, and I do not like driving cars, and I love, like, just biking to places. So I feel like I just am a person that is just pretty damn simple, and so was my grandfather, who we talked about, who we opened this episode with. And he ended up-- I mean, he and his, you know, wife, my grandma, they had 12 kids. My mom is one of them. And my grandpa, through his-- It's not even really frugal. I-- It's-- I don't even think frugal is the right word. It's just, like, simple and, like, content and, like, you know... With all 12 kids, as much higher education as they wanted, it was all paid for, and I like that. I like being able to, like, for the things like, you know, medicine and education no problem at all. And all the other stuff, like a nice watch or something, I just don't give [00:21:01] Doug: Yeah. Yeah, yeah. Well, I was gonna say you sound like Mr. Money Mustache a little bit with, like, bike everywhere, like, simple clothes, like, just content. Like, hike outside is great, you know, a lot of free activities are great. Well, you'll figure it out. I was gonna... You know, the observation is it's not a-- It's obviously a wonderful problem to have if you're like, "Oh, I, I'm, I have more money to spend." But you highlighted, I mean, a couple, couple things. Like travel, it's almost unlimited, like, as you're, you know, if you're like, "Okay, maybe I'll get a nicer, like, nicer amenities." And, you know, it's cool to test that out and see, like, do I like the bigger seat? Or, you know, a big one is just, like, getting good flight times, which may or may not impact, you know, the travel that you're doing. But it's just like, do I wanna wake up at, you know, 2:00 AM to catch the 6:00 AM flight 'cause it's a little bit cheaper, or just, like, pay for the convenient flight and, and that sort of thing. So you'll figure, you'll figure it out. But yeah, it's like a, it's a challenge. Like, within the household here, like, I, I, I'm more likely to spend more. And then I have friends that have, like, a considerable amount of money, and they also enjoy thrift stores, um, and just other stuff. They don't wanna accumulate a bunch of things where it's like, all right, now it's just cluttering shit up and, and, like, it's a burden versus, like, a enjoyable thing. So yeah, weird battle, but congratulations on, you know, being successful where you have to figure out this problem. [00:22:37] Elliott Z: battle. You know, one thing I'd like to share, 'cause this is kinda new to me, uh, one thing that I would never have done before is, like, Ubers. Like, Uber straight from the airport to the exact place that you want, what a difference of... rather than, like, taking the public transportation for, like, an hour and a half. Yeah, there are, there are things that I've, like, I've, I feel like I've cracked open my wallet a lot more these days, but I also know that I'm in this special financial zone right now of, like, I'm single, I have no children. But the second that, like, marriage and children and h- house comes up, I feel like life just gets more expensive, and I feel like I will hopefully just be prepared when or if that happens, and I'm kind of just, you know, building up right now so that I don't wanna or don't have to worry later. You know? Or, like, I don't know, don't have to worry financially later, which kinda feels like a good place to [00:23:34] Doug: 100%. Yeah, yeah. Great way to put it. And, uh, yeah, I also vote for if you, if it makes sense in your budget financially, like getting the convenient option, like the Uber directly, like exactly what you said. I've gotten one from the airport here, which is kind of far, and I think with tip it's like over 100 bucks or so. But fuck, it's so much more convenient, um, than having someone drive for an hour. Anyway, it can get expensive, but, like, I don't do it all the time, and sometimes it makes sense to pay for that convenience. So, awesome. All right. Well, this has been fun catching up. Where can people find you and, learn a little bit more about you? [00:24:15] Elliott Z: Yeah. I am on Instagram @elliotzilinskas. Uh, my X is Elliot Zeli, so just kind of a shortened version. uh, just talking with Doug, I created a little blog that I am kind of just writing about the things that I'm learning about AI. It's called builderclub.ai. And yeah, you can find me find me at one of those places [00:24:36] Doug: Awesome, man. Well, we'll catch up before too long, and thanks a lot [00:24:40] Elliott Z: Can't wait. Thanks so much, Doug

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