Financial Feminist - 275. Roadmap to Quitting Your Job and Building a Business in 2026 with Sam Vander Wielen

Episode Date: February 24, 2026

If you’re thinking about quitting your job in 2026 and finally starting your own business, this episode is your practical roadmap. I’m joined by lawyer-turned-entrepreneur Sam Vander Wielen, who left corporate law with multi-six-figure student loans, built a multi-seven-figure digital products company, and learned firsthand what entrepreneurship can and cannot do for your happiness. We’re talking about how to financially plan your exit from a 9-to-5, what legal steps you need (LLC, contracts, trademarks), and how to stop tying your worth to income, vanity metrics, or job titles. If you want a sustainable, smart plan for quitting your job and building a profitable business in 2026, this conversation will show you how to do it without burning your life down in the process. Sam’s links: Get Sam’s book: https://www.samvanderwielen.com/book/ Listen to Sam’s podcast: https://www.samvanderwielen.com/podcast  Sign up for Sam’s newsletter: https://www.samvanderwielen.com/easy-emails  Visit ⁠https://herfirst100k.com/ffpod⁠ to see the show notes and read the transcript of this episode! 0:00 Intro 01:15 The Happiness Myth 04:30 Why We Tie Happiness to Milestones 07:30 What a Business Can (and Can’t) Give You 11:00 Money as a Tool for Safety and Choice 15:00 Sam’s Corporate Law Wake-Up Call 20:00 The Stability Myth of Corporate Jobs 25:30 Planning a Real Exit From Your 9–5 30:30  Legal Basics for Starting a Business 36:00 Why Entrepreneurship Doesn’t Fix Your Life 41:30 Redefining Success Before You Leap Learn more about your ad choices. Visit megaphone.fm/adchoices

If you're ready to finally quit your job and be your own boss in 2026, this episode has the roadmap. I'm joined today by Sam Vanderweelen, lawyer-turned founder, creator, and best-selling author of When I Start My Business, I'll Be Happy. Sam built a multi-seven-figure digital products business, survived a brutal corporate law career, paid off massive student loans, cared for dying parents, and weathered more wake-up calls than most people see in a lifetime, all while learning what entrepreneurship can actually give you and what it absolutely can't. This is a real conversation for anyone who has wanted to be an entrepreneur, but something's held them back. Confusion about corporate structure or if you need a lawyer, worrying that your business will solve

all your problems and then realizing it won't. And why the stability myth of corporate is just absolutely damning, especially at this time right now. In today's conversation, we get into why tying your happiness to income metrics or a business launch will always leave you disappointed, planning a realistic exit from your nine to five, including building a financial off ramp, and what you really need legally, LLC, contracts, trademarks, and what you absolutely don't need a lawyer for. A lot of people want to talk to you about building a business. This episode is the nitty-gritty. How to actually do it in a way that's sustainable. Let's get into it. But first, a word from our sponsors. Ah, where are my gloves? Come on, heat. Winter is hard, but your groceries don't have to be.

This winter, stay warm. Tap the banner to order your groceries online at Wala. enjoy in-store prices without leaving your home. You'll find the same regular prices online as in-store. Many promotions are available both in-store and online, though some may vary. When I start my business, I'll Be Happy is such a pointed title. What made you want to debunk that myth? It's so important that people know that that is not true. And I know because I thought it was true. And I had my ass handed to me. So I feel like I just had to be like, guys, this is like warning. This is not true. Yeah. What do you wish more people? people understood about what a business can and cannot do for your life.

There's so much that a business can do for you. And I do think a business can provide you with a lot of happiness, not in my opinion, not directly through the business. Like, I don't know about you, but when you look at your Instagram account or something, like that's not what's bringing me happiness. The flexibility, the money that I've made from my business that I've then gone and used to do things like investing in real estate, taking trips, having it experiences, helping other people. That has made me really happy. It's not that a business can't

provide you any happiness. It's just that I came into this thinking, if I had those vanity metrics, if I made a lot of money, therefore I will just be happy. Can we talk about that for a second, that feeling? Because I think that is a unique thing for women, especially where, oh, when I lose this amount of weight, I'll be happy. And then I'll wear a bikini. When I, yeah, make X amount of money and my career, I'll be happy. When I finally launched that business, I'll be happy. What are we getting wrong about that mindset? That our happiness exists in anything that's outside of us or probably what we already have, even that our mindset exists in material things. It's kind of funny, like the more money I've made in my business and the more opportunity

I've had to buy material things, I've probably bought less and care less about it, to be honest. Yeah, I think largely that's true for me. I'm making some lifestyle upgrades, but I think a lot of the things that we believe we should be buying when you're rich. Like the fancy car is like, it's not really of interest to me. It was, I know like for me and maybe anybody listening, coming from like a corporate background, having at first, just like building up enough of a nest egg in my business, like when it started to do really well, that, that cushion that I was able to build up gave me the greatest amount of happiness because it meant that I could work. I could not work if I wanted to or needed to. Like if something happened, like a lot of what happened to me, I had

brain surgery. Both of my parents died within the same year. So I had a lot of time where it was like, I actually can't do anything or I don't want to. I wanted to take care of my dad while he was sick, for example, and become his caregiver. Not that I was happy he was sick, but like, could you imagine if I had still been working in corporate and making less money and what would I have been able to do? That's But that money bought me time. That bought me expansion with him for myself to take care of myself. Yeah, it still does. Can we talk about that corporate career for a second?

Because you started in law and you had sort of like this harrowing wake-up call that your life wasn't what you wanted it to be, which I think we all can relate to. Can you take us through that story, that kind of wake up in the middle of the night moment where you realize this is not what I want? I was working as a corporate lawyer and a big law firm and I had gone out and bought myself like a bang in Mercedes. had all the bells and whistles, I thought, okay, well, I hate this job, but at least I'll have a nice car to drive back and forth. That's literally what I thought. And I remember one day at lunch, I sat in my car eating lunch and crying because of how much I hated my job. And I thought,

how funny is it that this car that I bought to drive me to my miserable job, I'm now sitting in it, crying in this career and I hated it. Unfortunately, I was not very familiar with a lot of mindset work at the time. I became a lawyer at 23, so I was pretty young. You know, I really adopted this like victim mindset accidentally of being like becoming a lawyer happened to me. I had a very traumatic, very violent childhood. So I wanted to get out of it as fast as possible. And I saw becoming a lawyer as the fastest, surest, safest way to doing that. I thought lawyers have stable jobs, stable income, like all that stuff. Yeah, it was not what I thought it would be. There's news alert. There's no justice in the legal justice system in this country.

So that was a hard lesson to learn in real time. I was not happy and I wasn't also seeing any way out of it. I had multi-six-figure student loans. I was also pot committed. Like, I've told everybody my whole life I wanted to be a lawyer. What am I going to do now? It's so embarrassing. And I didn't really have an answer for what else I wanted to do.

So I felt very stuck. And then I had this plane ride. I took my first big vacation as a lawyer and I went all around Northern Europe. and I was flying home, and we had a really, one of those, like, horrible, violent, turbulent issues

that you hear about on the news. And it really, I've never had a moment since. It was just like it literally shook me awake. And it was just like, what are you doing with your life? Why you're acting like you have no control? You actually,

I had a lot more control about my career switch than whatever was happening on that plane and whether we landed safely. And literally within three days, I started an online business and was off to the races. Wow. So what did you think you were getting by being a lawyer that instead you ended up giving? I thought I was getting an opportunity to make things right for people. Yeah, it was justice. I really thought lawyers are the people who set things right in the world. And don't get me wrong, there are plenty of lawyers who I guess get to do that. It's few and far between. If you're one of them, reach out to me. There are many lawyers doing good work. I'm not trying to say that. But overall, especially when you work in corporate,

Like your job is to make other businesses a lot of money, and it tends to be that those businesses are not doing fantastic things. And so it wasn't making me feel great about it. What I ended up giving a lot was business advice because I was in the corporate department. And so when I would see like a new client came in who had a small business, I'd be like, oh, can I work with them? Because I'm really interested.

I want to work with someone in my community. and we would handle the legal stuff, but I'd be like, yeah, yeah, yeah. So like, what are you doing about the marketing? Like, do you have an email list? Have you ever? And I started getting really into it. Like, I was just very curious about it. What you just said is so smart that I wish more want to be entrepreneurs understood or side hustlers understood. I have said this many times, but I remember working my nine to five that was fine. I don't think I hated it. Maybe especially you hated yours, but I was like, this is fine. I just know I don't want to do this forever. And then there were some jobs that I really did not like.

But I remember always feeling like it was a waste of time. Like, oh, I could be working on my business right now. Or why don't I just quit, right? Because then I have so much more time. And what I realized was my 9 to 5 was both the financial investment into my business, but also I was learning all of the skills I needed to be a business owner, even in toxic or bad situations. Because it was like, oh, that's never how I'm going to run my business.

I'm never going to say that to a team member. or I'm not going to, you know, rely on this thing that I see them relying on that costs a ton of money, but does not make a return. And so you're almost like beta testing, being an entrepreneur in your 9 to 5 job, and especially the fact that you're like, give me the projects that are going to suit me up to be an entrepreneur, I think is so smart. Yeah. I think that it's, you know, it's also helpful if anyone's currently in corporate, like trying to plan their, you know, exit strategy to take this time also, as Troy's saying, to use this time to learn the skills and observe a lot of what's going on around you, meet as many people as possible. But I also,

I think, became more familiar with what my superpower was, even as a worker. And my superpower was that I'm super efficient. I get, like, I crank out more content than, you know, my friends are always like, I don't understand how you, it doesn't take me a lot of time, right? So I'm just super efficient. And efficiency is the worst thing as an attorney. So my superpower was actually like punished, right? They'd be like, you need to take more time with this. You need to bill more hours. And so it was helpful to turn on that like, well, what could I do?

Right. And then I go on and I start this passive kind of quote unquote passive digital product company where it's like I created these digital products eight years ago that are selling every single day. Like what a fantastic way to utilize my superpower, you know? I think that's so smart as well. before we talk more about your business, I do want to talk about the fallacy of that stable job because I felt it, I think, just personal finance education largely until a couple years ago

was like try to make as much money as possible in your 9 to 5 job, even if you hate it, so that you can then go out and do more things, right, pick the stable career. And I think especially younger millennials like myself, people younger than us who are Gen Z are just like, I'm not, doing that. Like, I'm not tolerating things that I don't want to do or work that I don't like, even if it affords me a different life. And I think there is this lie that we were told of take the stable paychecks, take the 401K. That is the stable option. When in actuality, entrepreneurship, especially for women, can be the exit to so much more. So what do you have to say to somebody who is in their stable job, but knows they're meant for more than that.

I think it gives the appearance of stability, but there's probably a lot less stability than you realize. Maybe this is also my upbringing of I was raised in a way that I had to always bet on myself, right? But I would rather bet on myself than relying on a lot of factors outside my control. pretty ironically my department got laid off not that long after I left actually but I would also encourage you to explore more of an expansion mindset if you're thinking this way that I think about this all the time like when I left being a lawyer I had multi six figures in student loans and I was like making my probably $200 payments or something like this a month not making a dent in anything and and really wondering like how am I ever going to pay this off and I paid it off so fast with my own business right

So I don't even know that I still would have had it paid off as a lawyer. Yeah, I mean, I didn't have six figures of student loans, but I had a car loan. That was like my big existing debt. And I paid it off, I think, two, three years early. And my car loan was pretty short. And I paid it off way quicker because of entrepreneurship. It was a huge rocket shift towards my financial goals, absolutely. But you said something interesting in the book, which is most people don't spend

enough time thinking about their personal budget before they start a business. And I could not agree more. So what do you think is the biggest? financial blind spot that people are walking into entrepreneurship with. People think that when you go and start a business, that your business is going to or needs to immediately provide for your personal budget. And I just don't think that's realistic. It takes a lot of time. Yeah. And so I talk a lot in my book about how I built a bit of an off ramp. Like I did save up. I cut my spending. I changed my behavior. I sold stuff.

Like I did everything that I could because I really wanted to make this happen. But I didn't rely on my business financially. My business ended up being able to pay me. But that was like, it was all bonus to me. But this is, I think, the biggest killer. I get emails every single day from people being like, I can't invest in like your legal templates, for example, to start my business because I'm not making any money. It's like, wait, you need to do that in order to start a business.

So there has to be a plan. There has to be a plan for you as a person of how you're going to support yourself. and then how, like, what little money you have that you can invest in the business to get it started, it's way too much pressure, in my opinion, to put on a baby business to expect that to support your personal lifestyle off the bat. Yeah, I couldn't agree more. I mean, the phrase spend money to make money, I think is so true for entrepreneurship. Now, we don't mean spend stupid money because that's not going to make you money, but like truly, I wish more women understood that you have to invest in your education in order to be a successful business owner. That is the time to invest in

templates, invest in a coach, invest in learning more. And I think it's so interesting that most of us go to college, we spend more money than God getting a degree that so many of us don't even use, but then we never spend money trying to learn again. We might go get a master's, we might get a JD, something else happens. But I think the vast majority of people might go to college or even to get two-year degree, spend a bunch of money and then think, oh, I'm never going to spend money on learning ever again. And I think that's one of the most damaging things you can do, especially as a newbie entrepreneur. Yeah, I totally agree. I mean, I get emails from people all the time saying that they want to start an online business to make money, but they have no money to get started.

And I write a lot about this in my book, about how, like, I'm so happy to report that starting an online business is so much more affordable than if you were starting a bar studio, you know, in your town. And like, it's a huge investment. You've got to get space and all this stuff. So it's way more affordable. It's not free, though. And both in your time, your education that you have to invest, equipment, some basics. Like some people, there's been a disservice, I think, in the online business industry and, like,

the online marketing. A lot of people yelling at you saying that you have to buy their course on Pinterest and this thing and that thing in order to get started. But I think what Tori and I are talking about is, like, more of the basics and the foundation. Like, there is some upfront investment. And I do think that there's some courses or education. that's super, super valuable. I'm biased, but I think my shit's really good. I think your shit's great. I invested in those kind of things when I first got started because time was a limited resource.

And I'm like, okay, I could spend six months or a year wasting my time trying to learn this thing. Or I could spend a couple hundred dollars learning from an expert who's already made the mistakes. That's a worthwhile investment for me. Maybe not a $30,000 coaching program. But like, a couple hundred bucks to save yourself a bunch of time and stress, probably worth it. Yeah, I think one of the best mindset shifts you can make around money when you start your business is to start seeing your time as money as well. And so I very quickly started being like, okay, if I collapse two hours because I do this thing, that's two hours I can spend creating something that can make me way more in the long run. So like really switching into that mindset helps.

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if you're selling digital goods or things that need shipping, I love that you can use Squarespace to offer services and get paid. So consultations, courses, events, experiences, all of that can happen inside Squarespace so you're not paying like a different payment platform to handle it for you. You can also buy a domain on Squarespace. It makes it easy to find the best name for your business. And you can make sure to sell anything from products to content to time all on your Squarespace site. Had on over to Squarespace.com slash FFod for a free trial. And when you're ready to launch your brand new website, use SFPod to save 10% off your first purchase of a website or domain. I think there's this romantic idea that people quit their 9 to 5 and it's completely in their control

and they've done all of this stuff to figure it out. And then they just go for it. But I think I have this theory that there's two kinds of entrepreneurs. There's one that's like leap in the net will appear kind of entrepreneur. It sounds like you and I are both number two, which is I need a net and a backup and a backup net and the backup backup backup. Back up. And then six parachutes too. So you were meticulous in your planning. What is a realistic timeline and exit plan from a nine to five actually look like? I think that's why it's so important to know what your personal budget is. Right. So like if you're like boozy as shit and you have like a huge personal budget and you have a huge mortgage to take care of and you don't have a partner who you split expenses with, there are all kinds of factors. But that's why I love starting there because then from there we're like, okay, what kind of money can you even stash away from now till you quit? Some people in their nine to five could really buckle down and stash a lot. Other people, they're already living tight. And so you might only be able to move over a little at a time. So I would start with that. I personally, like to take that time also to get done the like foundational things in getting your business started

that you don't get paid for that you're not making any money. So like register your LLC, get a domain name set up, like start getting these little things. Get your business bank account set up. Do those little things because those are all a pain in the touch to just get done. They cost very little money, but you could maybe use your current income to pay for them. And that way when you do leave, you can hit the ground running. So whether maybe that's six months, for some people. I know for me, that was probably about six months, but I was saving, and I'm always honest about the fact that I had a partner who was providing me health insurance, so that made my life a lot easier, obviously, in America. And I didn't have kids. So I was able to

like just stash, stash, dash, dash as much as possible. You have this three-step process, save, sell, make that you followed. Can you walk our listeners through that? Yeah. So I think like sometimes people will talk about one of these, like they'll think I have to save money or I should just start selling things that are in my basement. But I actually like a little bit of a combo of all three. So I started saving by spending less, right? So I was cutting my expenses. I was just really buckling down on like, even looking at expenses was kind of funny, like of what things I was spending money on to make myself happier in my miserable career. And I would think like, well, if I was not in this career six months from now, I wouldn't need that thing. So I was going out for these like luxurious lunches every day, just get out of the office. I started bringing my own lunch. Like it was like $50 at a time. It really added up. I also did go through my house and got rid of a lot of things that I knew I could sell off. I think I made enough in expenses. Like I had a friend who was teasing me as like, oh, what's the big deal? Like you don't, people don't really make that much money. Like I paid for my domain name. I paid for my LLC. I paid for like a bunch of the original startup.

cause of things. And I think I paid for somebody to make me a logo or something at the time. And so that was helpful. And then the other thing I always suggested to people is like, is there anything else you can do to make any more money right now if it's temporary? I took on like a part-time attorney job just so there was extra income for a short period of time. It was about six months. I rightfully think that hustle culture has been so demonized. But what you're talking about is like a hustle season. and I do think those are so important to being a successful entrepreneur or getting yourself to where you can quit your business. Like when I was launching my book and you're probably feeling similar, it's like I am,

I hustle really, really hard because I made a commitment to myself of how I wanted this book launch to go. I had spent so much time on this thing and I wanted to be really successful. So I worked more hours. I did more things than I normally would. And then I took a break once it was over. Can we discuss hustle seasons? Because if you really want something,

you are going to have to work for it. And I don't want to lie to everybody listening of like, you can live this soft life all of the time and still get the things you want. I don't think that's true. Yeah, I completely agree. I actually don't think I've been a business for eight years. And, you know, I've had seasons.

where I could pull back, but it wasn't until like the last two years that I really, like, I can really chill and still do well. And that's very unusual too that people like you and I can do this. I know you and I prioritize like our health and our lives and we live our lives. And that is also not the case, even when people are in business for eight plus years. Right. Yeah. So I very much believe that not only is a hustle period required, I don't think it's necessarily a bad thing. Like I just think as long as we keep it to the period, right? Like, I don't, not asking you to sign up for this for life. But I think it shows that there's some passion and there's some grit. And honestly, Tori, I think about it a lot. Like, I actually miss those days a little bit. Like, I was hungry. Oh, they're fun.

I had nothing to lose. I was scrappy. Like, I write a lot about my book that I think that entrepreneurship requires a lot more scrappiness than people want to talk about too. Resourcefulness. Like, I was reaching out, asking for things, really utilizing my resources. Yeah, just seeing like, I don't know, I almost didn't even know what I was in for. And I would encourage you to see that as a really positive fun thing. My favorite word in the world is curiosity. And I just like recommend going into this process as curious as possibly. Like, let's see what happens. And if you end up building a business that gives you chill, then I feel like you've made it in my opinion. I was literally just thinking about this yesterday. Taylor Swift just went on this two-year career-defining, really intense, really physically, emotionally demanding towards. and now we don't see her. But that's the idea. Harry Styles, same thing, right? Wins the Grammy for album of the year,

does this massive tour worldwide. And now we, like, don't see him. And it's like, those are the, you need both. You need both seasons, but I, like, I'm not glamorizing hustle culture, but I do think hustle seasons are required.

And you do have to find the fun in them. Like, it can become a game. Like, you have to sprint at times. if you want a business to be successful. Yeah, it's kind of a funny evolution because I feel like entrepreneurship became my identity, which was pretty fun for a while. I mean, I also started in like the girl boss era. Me too, girl.

Yeah, so it was like cool back then. But I do feel like it was kind of fun. Like all of my friends became like other online business owners. It was a fun period. And then I feel like the next shift is actually decoupling. It's like I now my identity, I have like, very hard to completely remove my identity from my business or how well my business is doing or how much money or followers or whatever. Yeah. What are the four stages that someone's going to

experience when launching their business? The first business phase that you will probably go through is what I call the seed phase, which is, and you're probably going to have lots of little seeds. And maybe someone listening is sitting here thinking like, I could become a health coach or open a flower shop or open a bar studio or be a food blogger. Like, I'm sure you're a multi-passion person, you know, I think everybody kind of goes through that phase as an entrepreneur where you try to make your hobby, your business, and try to monetize every single thing that you do. And I do think kind of again to this like hustle period, I think it's cool to explore those and be open to the fact that some of those might not work out. Some of them might. And some that

you didn't think were a good idea might be the ones that take. So in my opinion, the next phase is really that sprout phase where it's like, okay, a couple of the seeds you planted. You tended to. Some of them actually sprouted. They start to grow. They can take off. This is when you start to actually get your feet under you in your business. Now we're looking at like how are we scaling, expanding, hiring, all that. And I actually think the final phase is kind of like a propagation phase because it's really, it's probably what I'm in and you keep going back to of like, okay, now what do I want to cut? What do I want to stop doing? What can I afford to not do anymore? How do I get more efficient, you know, all of that? Yeah. And I think there's two problems with people

who are about to start a business. It's either I don't have an idea or I have too many ideas. So can you maybe walk us through a framework that helps them identify what that idea should be that they invest in the business for? Yes, absolutely. So I really recommend, you know, a nice blend of something that you're interested in because I want you to be interested in have some passion behind it. But I think that I'm a really good example of somebody who started a successful business of something I'm not necessarily interested in. So I'm a lawyer. I would not say I love legal templates. It's what I sell, right? It's like I don't know who does. That would be really weird in my opinion. But my life's passion is legal templates. Like contracts or my passion.

No, I do not. But what I am really passionate about is helping other women start businesses. If that's the thing that I'm good at, like, okay, I just happen to get educated in this area. I can do that. And yes, I sell you the contract, but you're writing to me, about your business ideas. And you're writing to me about like, oh, I'm starting this thing. So I think it's a nice, like, marriage of thinking about what you really like doing and where is their demand and supply. So I don't think that enough people do enough demand and supply research. Oftentimes people do very quick supply research and they see, oh, there's a bunch of people on Instagram, being money coaches, for example, therefore there's no space for me. And they just like

instantly take themselves out of it. Instead of being curious about it and thinking, Well, first of all, that shows that there's demand, so that's interesting. But also, are there any differentiators, for example, that are missing? When I started my business, I wasn't the first person to do it, but I saw a huge, huge hole in the market that I thought was missing, specifically for online businesses, for creators and creators having access to contracts and stuff, who also didn't want all the fear tactics. I'm a really chill person. I'm not going to do that. And that's how I wanted to run my business. And so I started and it was like, boom, off. to the races. So there's that mix of like, I'm interested in helping you start a business. I've got

this experience. I saw some supply, which showed proof of product, but I also saw there was a demand for like something that was a little different. And so I like to think of it as like building a recipe in that case. We did a previous episode about side hustles and we'll link it down below. But our guest, Janice, talked about walking through the bread aisle at the grocery store and being like, that's the experience of starting to be an entrepreneur, right? There's a million people making bread. There's a million different kinds of bread. And yet you're out there being like, I can't make bread because other people are doing it.

Look at the bread aisle. There's a million types of bread, million different people making bread. You can offer something. You can be a photographer, even if there's a million photographers. You can be a money coach, even if there's a million other money coaches. You just have to figure out your value proposition. What is the thing that's differentiating you from? everybody else doing that. Yes. And then as I talk a lot about in my book, actually be different.

Like, I talk, my mom used to always say be interested and interesting. And like, you have to actually be an interesting person and then show that part of yourself, like in your content. Like, if you think you have a spicy take or you think you have a different way of doing it, I certainly hope you're talking about it. Okay. We can't not talk about some legal stuff. When does a business actually need an attorney? Nowadays, a lot of people don't necessarily need an attorney starting off. I mean, I hope that that's what I help a lot. I've helped over 350,000 people start online businesses. So, I mean, most of this stuff you can do affordably on your own.

You can register an LLC, get a basic contract in place, go get a business bank account, which I was- Can I pause you right there? Yes. Because I've talked with, seeing, hundreds of thousands, millions of people who want to be business owners. And they hear, because I just went through this with my partner a couple years ago. I was like, you need to have a business for what you're doing.

And he was like, that takes so much work. I'm like, you need an LLC. And he's like, oh, but doesn't that cost thousands of dollars and take a bunch of paperwork? So I want to stop you right there. What is getting an LLC actually cost and actually mean? Because I think it's going to blow everybody's minds. Yeah. This is a big reason why I started my business actually because it infuriated me as a lawyer,

how I felt like it was so unfair and so unjust of like it's stopping a lot of people from starting their own businesses. So I at least consider, this is just an aside, I consider a lot of of what I do to be accessed. Like, I just want to give people access because this is so easy, you guys. You can all do this. So in, depending on where you live, like LLCs typically cost anywhere from $50 to a couple of $100. The only exception to this, or the major exception I should mention is in California, where we have to file this like what's called a franchise tax when you also file for an LLC, which costs like $700. So it's an additional expense. But worse, it comes to

worse, we're talking a thousand dollars, but I think in Washington State, it's a couple hundred. Yeah, in, in like Jersey and Pennsylvania, where I'm from, it was like 125, 175, yeah, they're not, we're not talking crazy. What ends up getting crazy is when you hire a lawyer to do it for you. So that's why, like, the product that I created just walks people through and teaches you how to do it yourself. It's very easy. The same place that this applies that will save you thousands of dollars is when it comes to trademarks. Trademarks themselves are not very expensive. They're very inexpensive, also copyrights very inexpensive. It's like 50 bucks. What becomes expensive are all the legal fees. You don't have to have a lawyer file those for you. A lot of people are really surprised to learn that.

You also don't have to have a lawyer draft a contract for you. So a lot of people actually think it's like legally required to have a lawyer give you a contract. I'm not saying it's not helpful. Of course, lawyers are helpful and they can make sure you do it right and that you don't run into trouble and it says all the right things and all that kind of stuff. But a lot of people that I'm dealing with who are starting like such small businesses. That's a lot. Like I, I'm very much a fan of let's get the foundation set. And then like I always say to my customers, when you become Amazon, if you want to do that, then you go get the lawyers. You know, like that's, that's when, you know, when you're on your way. So I think that it's, it's overkill when you're starting out for a lot of

people. And I will confess this on Mike. I don't think we did trademarks until maybe 2021. Yeah. And everybody, the podcast was already a thing. I already had a million followers. So, like, you need the LLC. Even the trademarks can come later. And if you're listening and you're a freelancer, you work from home as a freelancer. That can be your own business that then you can write off part of your rent or mortgage. You can write off your desk and your lights or your computer or your software.

All of these things can start being written off. Your coffee that you get with a colleague to talk business, all of these things are right off. So maybe I know you're not an accountant, but maybe can we touch for a second on the power of having that LLC to save you money in every other aspect of your life, not just your business? Yeah, absolutely. They forced me to take tax classes, so I'm happy to talk about it. I might as well get my money's worth. There's a huge personal financial gain to getting an LLC as well, because the point of getting an LLC, registering your business as an LLC is to personally financially protect yourself. So you don't want to be financial.

on the hook for anything that happens in your business. And then I always say that like part two of this conversation is that you then go and get business insurance because you also don't want your business to be financially responsible for anything that happens either because, you know, a lawsuit would cripple most businesses. So we don't want that to happen. So yeah, it can be very beneficial to you on the just like liability side to get an LLC. But as Tori mentioned, you also get to start capturing all of these expenses. I also want to mention because you mentioned about freelancers. I see this a lot and I talk about this in my book that often freelancers don't think about themselves as business owners. You are a business owner. You're just providing services.

That is your product, right? It's your service. People will often say to me, oh, I don't need to get an LLC. I'm just a freelancer. It's like that means you're a business owner. So yes, you would get an LLC so that it would legally protect you as a person, but also so that you could capture all these expenses. If you have income from another job, like let's say you work a nine to five or you have a partner and you filed jointly, you can reduce your taxable income if your business is even costing you money. So oftentimes there can be a benefit even when you're in the red. And again, to that, I'm a freelancer. I'm not an entrepreneur. If you do any sort of, you know, you have a 9 to 5 job and you do any sort of work outside of that for yourself. So that could be,

you know, I'm a 1099 contractor who teaches yoga. I am a graphic designer my 9 to 5 and I also do some graphic design. I design two logos a year for other people and get paid to do it. Those are businesses. And again, you can be writing off part of your house or your rent. You can be writing off so many other things that are not going to only save the business money, but also save you personally so much money. Yeah. I mean, if your home office is 10% of your total square footage, you not only get to take that portion of your rent or mortgage, you also get to take 10% of all of your utilities, like all of the things that you're using to heat that space. Yeah, Wi-Fi phone, all of that kind of stuff. So, yeah, it can be a huge benefit for people. And people often don't

know that it can reduce their taxable income for their other job or when they're filing jointly as well. Totally. You have a quote in the book, quote, these days, I love what I do and I love my business. But my business is not my passion. It's my job. And it's a job that allows me to chase my actual passions like cooking outside of my day-to-day work. You mentioned this briefly at the any of the episode, but talk to me about why it's so important for entrepreneurship or your business to not be all-consuming your complete identity. Because you're in for a wild ride, if it is, because it's a roller coaster. I mean, there are times when your business is picking up steam, has momentum, then things slow down. You have a big sale. You feel high. Three days later,

you're like, what sale? I don't care. You will learn very quickly that this stuff is very fleeting. I literally dreamt about getting a book deal and I said, oh, if I ever got a big five book deal, I mean, come on, that's crazy. Got the book deal. Sat there and freaked out about it the entire time. I wrote it just so worried. My whole life's problems weren't solved by getting this book deal. You know, I still had stressors.

Like, it'll just, it'll be a wild ride. But also, like, I mean, I get a lot of anti-Semitic comments on social media, for example. I get nasty emails and messages. Things happen. And so it's like, if I was defined by that, I see this. stuff now and I'm just like, I mean, I know you, you get the same thing. It's just, it would be very difficult. But I hope like my mom always used to say that somebody's weight was the least interesting thing about them. And I always hope that my business is the least interesting thing about me.

Yeah. I think about that a lot too, especially as somebody who used to define her worth and her accomplishments. I've said this many times in the show, but my mentor told me once that I'm a human being, not a human doing. And I was like, why does something so simple absolutely fuck with me and change my entire life? But it's true.

It's like, I am very proud of the work we do. I am so proud of this. I do say it's my life's work because I do believe that this is the way I can have the most impact. And also, I hope that this is not

what is listed on my Greystone. Yeah, like Tori had however many millions followers. Like I just don't think that that's going to matter in the end. That's the way I think about it. I think I'm pretty heavily impacted by the loss of my parents. I just lost both of my parents back to back. And it's like,

I don't know, it is a wake-up that you're just like, this doesn't matter. You know, I'm going through my own existential crisis where I'm like, none of this matters. This is not who I am, you know. Well, and you and I had talked when we met that, you know, that had happened to you and I'm so sorry for your loss. You at that moment and then, you know, your near-death airplane moment of these kind of, yeah, wake-up calls. I think a lot of women either experience these wake-up calls don't see them for what they are. It's easy to ignore them,

or they get the wake-up call and they don't actually use that to take action or they do it for a little bit, but then life gets in the way. One, how do we identify wake-up call moments for what they are? And two, how do we actually use them to spur ourselves into action? I think the first thing,

is just a shift in the mindset of like everything is an opportunity. And like I know I already had my business, but it was still pretty early on. It wasn't like, it was maybe doing multi-six figures at that point per year. It was not too crazy. And then my dad got leukemia and I became his caregiver. It was like, okay, well, what do we do now? And it became a curiosity like open point for me. It was just like, well, my business is way too reliant on me. I saw that it. If my foot wasn't on the gas, the business slowed down. That if I wasn't on Instagram, at that time doing Instagram stories every single day, like educational teaching things, it slowed down.

And I just thought it can't be this way, whether he's sick or not. I took it as an opportunity. I totally retooled my business. And I mean, talk about another hustle period, right, where I was like, I'm going to get this thing in place. It was like an investment. I'm going to get this thing in place now so that it pays off later. And I was able to take care of him for a long time until he passed away

from his leukemia. So it's like, yeah, I think seeing those things is like, what, what is it's like, what friction is this causing? And what could I create out of this that would actually resolve this friction even for the long term? We're talking a lot on the show lately about disappointing people. And I have mentioned this before that my parents don't fully understand my business. I think for the first time in the past year or two, they're at the point where they are like, oh, this is actually successful. But at the beginning, they wanted me to keep my job. They wanted me to keep my steady paycheck. And I think that in order to grow the business the way I wanted, in order to do the things that I wanted, at times, they've very severely disappointed them. How do we get over the fear

of disappointing others, whether it is starting that business, growing it the way we want, not aligning with people's expectations for us, if it means we're doing the thing that we truly feel is right for us. Yeah. What a great lesson to learn too because as a business owner, you're going to disappoint people all the time. Constantly. Yeah. Even when you do things perfectly, you know, like you nail it and someone's still pissed out. It's just the way the world works. So like, I think, you know, it's really important to remember that when you start a business or I think make any life change. Like if you told people you were going to get divorced or cutting off all your hey or like whatever. People project all their stuff onto you. And this is especially true about

people who care about you and people who are worried about your safety, right? So it's like, they mean well, but people start spewing all their stuff on to you. And like it's their feeling of insecurity of like that would be unsafe for them. That would make them feel unsafe. Some customers have told me that parents have told them it's irresponsible or like that you're throwing your life away, you know, throwing the stable job away. So I think it's just recognizing. recognizing that that's a bit of what's going on, at least that's helpful for me, is like, oh, this is like your thing. That would make you really uncomfortable, but I'm, I'm deciding to do that. It's probably also just like, there's no way getting around it of saying, like,

entrepreneurship takes a lot of grit and a lot of betting on yourself. You're going to get a lot of feedback from people. I remember when I left the firm, the managing partner told me, like, do you know how many businesses fail in their first year? And like, you're always welcome to come back. And I was like, great, I won't need to. And that wasn't because I thought I was going to be successful. I just thought I'd figure it out. And I think that you have to, like, yeah, you might face a lot of people doubting you and saying these things. And you can't go leave your job or start your business or think about maybe like escalating

the business you already have only if everybody is like super nice and supportive. Because when you get to Toriesize and you start getting messages and comments on your stuff all the time, you're going to have to have some thick skin, man. And it's like my friend always talks about being like a tree and that we have to be like like a tree and like further and further grow our roots and like really cement our roots because then when the wind blows like the tree is not going to fall over. But if you just like let it be a little baby tree forever, every single time there comes a windstorm, you're getting knocked down. And so I really think about that as like it's my job to keep working on myself and be like more

and more cemented in what I'm doing. I can't get it from everybody else. I don't know why I didn't think about it until you just said it. I was talking about like disappointing people before you're starting your business or as you're like growing it. You're so right that like you're always going to have a customer who's mad at you. You're always going to have somebody on social media who's mad at you. You could be Mother Teresa and you're always going to have somebody mad at you. And it's like that's just part of this is you're going to disappoint people. And the promise I made to myself is like you can disappoint anybody. That's fine. I gave myself permission to disappoint other people and I have to keep reminding myself of this because I want to be also liked. And so that is very hard.

But I can't disappoint myself because I have the highest standards for me. So if I disappoint myself to make other people uncomfortable, I have failed. But I have not failed if I disappointed other people, but stood in what I know to be true or right or the way I want to do things. Yeah, absolutely. Like not getting that affirmation from other people. Yeah. And I think you're right. Like you're also going to piss off and disappoint people when you, if you leave your corporate career and people are going to be like, it's crazy.

you left being a lawyer and that's so irresponsible. You just, I got it all of like, you spent so much time and so much money and so much and this is what you want to. I don't want it anymore. So I think what I'm trying to say is like if you're facing that disappointment on the front end now, I think it's a good thing because you're about to face it all the way through. Like that disappointment doesn't go away. It shifts from being other people, listeners, people in your inbox, whatever.

And you're allowed to change your mind when you have new information. Like you're allowed to change your mind. I thought I wanted to be an actor for so long. And at first when I sold out and didn't become an artist, it was like, oh, I am denying seven-year-old me's dream. And I'm like, seven-year-old me didn't understand that she was going to have to pay her bills. Like, seven-year-old me didn't understand what rent costs. Like, so yeah, she had crazy dreams. I am still doing something that I love that I didn't even know existed when I was seven years old.

And it didn't really exist actually when I was seven years old. You're allowed to change your mind when you get new information. Yeah. And I don't know why this comforts me, but I just always think about how nobody pays my mortgage but me. So I'm like, well, I get to decide at the end of the day. Like, it doesn't matter. Totally. So you've created the sustainable multi-seven figure business.

What does sustainability actually mean to you now? Not working like crazy. Being able to pull back when I want to. Not having to be on social media all the time. That's pretty big for me. Still having relationships. I know customers who are coming in and I still am pretty involved. I think you have to decide your level of involvement of how much you want to be integrated.

And if you can still do that, once I know that level, I'm like, oh, I can still do this. If it gets beyond it, then that's not worth it for me. I think that's what it means for me. And I don't do anything too crazy or trendy or like I try not to run off and do like everyone's saying you have to do this. I just kind of stay steady. And I like wait. I've waited out so many. trends and so many things that people have said like you had to do or couldn't do. And yeah,

I just think like slow and steady has won the race so far. My last question for you. What does success look like for somebody in their first year of business? That's a great question. I think that success looks like actually trying, failing and taking feedback from that failure and someone that keeps going. Because I think that senior partner who told me that a lot of businesses fail within their first year, I guess that statistic is true. But I'd be curious how many of those people, like, if they had kept out of, if they had a more open mindset, if they were curious, if they had done some of the things we talked about on the front end being a little bit more prepared. Like, I think that you can get through that first year, getting some experience under

your belt, just really seeing this all as like, it's like you're in an internship and you're just trying. You're literally learning how to become a marketer, a copywriter, your own legal team, your financial team, you're everything, your customer service representative. So you're just trying it all and like see this as that opportunity. And I believe a lot in future proofing. And I think a lot about what am I building, where am I headed? But in order to get there, I need to start acting like I'm headed there already. And so I just saw that first year is like that opportunity to start acting like I was headed in the place I wanted to go. I think that's such good advice. Sam, thank you for being here. Plug away, my friend. Oh, thank you. You can get my book when I start my

business. I'll be happy anywhere that books are sold. I'll make sure Tori also has a link to my newsletter, Sam's Sidebar. It's my weekly newsletter where I teach you marketing advice that actually works and that won't keep you on social all the time and legal tips that will keep you protected. I also have a podcast called On Your Terms since you like listening to podcasts. I love it. Thank you so much. Thank you. Thanks so much for having me. Thank you for listening to Financial Feminist, produced by Her First 100K. If you love this show and want to keep supporting feminist media, please subscribe or follow us on your preferred podcasting platform or on YouTube. Your support helps us continue to bring this content to you for free.

If you're looking for resources, tools, and education, including all of the resources mentioned in this episode, head to herfirsthundredk.com slash s-s-spod.