If you’re thinking about quitting your job in 2026 and finally starting your own business, this episode is your 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.
Key takeaways:
Your business is not your happiness
One of the biggest mindset shifts Sam shares is that entrepreneurship won’t magically fix your life. If you’re quitting your job expecting instant fulfillment, you’ll be disappointed. The roadmap starts internally: separating your identity from your income and understanding that a business creates opportunity, not automatic happiness. For anyone planning a 2026 exit, this is foundational. If you expect your business to solve everything, you’ll build from pressure instead of strategy.
Build a financial off-ramp before you leap
Sam emphasizes that most people underestimate the personal financial planning required before quitting. Your business will likely not pay you immediately. She outlines a clear approach of saving aggressively, selling what you don’t need, and finding temporary ways to increase income so you’re not relying on a brand-new business to fund your life from day one. A sustainable exit plan includes a runway, not panic.
Hustle seasons are strategic — not forever
Sam reframes hustle culture as temporary and purposeful. Building a business requires scrappiness, experimentation, and focused intensity, especially in the early stages. But sustainability comes from knowing that hustle is a season, not an identity. The goal is to build systems that eventually allow you to pull back without everything collapsing.
Use your 9-to-5 as entrepreneurial training
Instead of seeing your job as wasted time, Sam encourages using it as a testing ground. Corporate roles can help you identify your strengths, observe what not to replicate, build skills, expand your network, and fund your future business. Your exit strategy doesn’t start when you quit. It starts while you’re still employed.
You probably don’t need a lawyer to get started
Legal fear stops many people from ever launching. Sam demystifies the basics: LLCs are usually inexpensive, trademarks and copyrights cost far less than people assume, and hiring a lawyer isn’t legally required for most early-stage steps. Overcomplicating the legal side delays momentum and keeps people stuck longer than necessary.
Success in year one means staying in the game
Sam reframes first-year success as learning, experimenting, and continuing despite discomfort. In your first year, you’re learning how to be a marketer, operator, customer service rep, and CEO all at once. Treating that year like an internship, rather than a verdict on your worth, dramatically increases your odds of building something sustainable.
Notable quotes
“I hope that my business is the least interesting thing about me.”
“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.”
“My friend always talks about [how] we have to be like a tree and really cement our roots because then when the wind blows, the tree is not going to fall over. But if you just let it be a little baby tree forever, every single time there comes a windstorm, you’re getting knocked down.”
Episode at-a-glance
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
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
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Meet Sam
Sam Vander Wielen is an attorney-turned-entrepreneur and leading legal educator to online business owners. Sam’s the founder of Sam Vander Wielen LLC, the go-to contract template shop for online business owners that generates multi-seven-figure revenue annually. As the author of the book, When I Start My Business, I’ll Be Happy, and host of the On Your Terms® podcast, she cuts through the noise with no-fluff legal tips, refreshingly honest marketing strategies, and down-to-earth business advice to help entrepreneurs grow with confidence. Since 2017, Sam has helped over 350,000 online entrepreneurs legally protect their online businesses, all while navigating the devastating back-to-back losses of her parents, her own brain surgery, and becoming a caretaker. Sam lives on Long Island, New York, with her husband, Ryan, Bernedoodle, Hudson, too many coffee mugs, and a towering stack of TBR fiction.
Transcript:
Tori Dunlap:
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 Vander Wielen, lawyer-turned-founder, creator, and bestselling 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 9:00 to 5:00, 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.
When I Start My Business, I’ll Be Happy is such a pointed title. What made you want to debunk that myth?
Sam Vander Wielen:
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, warning, this is not true.”
Tori Dunlap:
What do you wish more people understood about what a business can and cannot do for your life?
Sam Vander Wielen:
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, in my opinion, not directly through the business. I don’t know about you, but when you look at your Instagram account or something, 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 experiences, helping other people, that has made me really happy. It’s not that a business can 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.
Tori Dunlap:
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 make X amount of money in my career, I’ll be happy. When I finally launch that business, I’ll be happy.” What are we getting wrong about that mindset?
Sam Vander Wielen:
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 funny, 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.
Tori Dunlap:
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, that’s not really of interest to me.
Sam Vander Wielen:
I know for me and maybe anybody listening, coming from a corporate background, having at first just building up enough of a nest egg in my business when it started to do really well, 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 if something happened. 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 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 money bought me time. That bought me expansion with him, for myself, to take care of myself. It still does.
Tori Dunlap:
Can we talk about that corporate career for a second? Because you started in law and you had 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 wake up in the middle of the night moment where you realized this is not what I want?
Sam Vander Wielen:
I was working as a corporate lawyer in a big law firm, and I had gone out and bought myself a banging Mercedes, had all the bells and whistles. I thought, 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 23, so I was pretty young. I really adopted this victim mindset accidentally of 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, all that stuff. It was not what I thought it would be. 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 hot committed. 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 horrible, violent, turbulent issues that you hear about on the news. 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? You’re acting like you have no control.” 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.
Tori Dunlap:
Wow. So what did you think you were getting by being a lawyer that instead you ended up giving?
Sam Vander Wielen:
I thought I was getting an opportunity to make things right for people. 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, 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 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, so what are you doing about the marketing? Do you have an email list? Have you ever…” And I started getting really into it. I was just very curious about it.
Tori Dunlap:
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 9:00 to 5:00, 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. Oh, I could be working on my business right now. Or, why don’t I just quit? Because then I’d have so much more time.
And what I realized was my 9:00 to 5:00 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 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 beta testing being an entrepreneur in your 9:00 to 5:00 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.
Sam Vander Wielen:
Yeah, I think that it’s also helpful, if anyone’s currently in corporate trying to plan their exit strategy, to take this time also, as Tori’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 crank out more content than… My friends are always like, “I don’t understand how you…” It doesn’t take me a lot of time. So I’m just super efficient, and efficiency is the worst thing as an attorney. So my superpower was actually punished. They’d be like, “You need to take more time with this because-
Tori Dunlap:
“You need to bill more hours.”
Sam Vander Wielen:
… it needs to be billed.” So it was helpful to turn on that, well, what could I do? And then I go on and I start this, quote unquote, passive digital product company where it’s like I created these digital products eight years ago that are selling every single day. What a fantastic way to utilize my superpower.
Tori Dunlap:
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 try to make as much money as possible in your 9:00 to 5:00 job, even if you hate it, so that you can then go out and do more things. 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. 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?
Sam Vander Wielen:
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, 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. When I left being a lawyer, I had multi six figures in student loans and I was making my probably $200 payments or something like this a month, not making a dent in anything and really wondering, how am I ever going to pay this off? And I paid it off so fast with my own business, so I don’t even know that I still would’ve had it paid off as a lawyer.
Tori Dunlap:
Yeah, I didn’t have six figures of student loans, but I had a car loan that was 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 ship 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 started 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?
Sam Vander Wielen:
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.
Tori Dunlap:
I don’t think so either.
Sam Vander Wielen:
Yeah, and so I talk a lot in my book about how I built a bit of an off-ramp. I did save up, I cut my spending, I changed my behavior, I sold stuff. 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 it was all a 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 your legal templates, for example, to start my business because I’m not making any money.” And 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 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.
Tori Dunlap:
Yeah, I couldn’t agree more. 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 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 a 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.
Sam Vander Wielen:
Yeah, I totally agree. 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 I’m so happy to report that starting an online business is so much more affordable than if you were starting a bar studio in your town. It’s a huge investment. You’ve got to get space and all this stuff.
Tori Dunlap:
Totally.
Sam Vander Wielen:
So it’s way more affordable. It’s not free.
Tori Dunlap:
No.
Sam Vander Wielen:
And both in your time, your education that you have to invest, equipment, some basics… Some people, there’s been a disservice, I think, in the online business industry and 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 more the basics and the foundation. There is some upfront investment.
Tori Dunlap:
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 kinds of things when I first got started because time was a limited resource, and I’m like, 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 a couple hundred bucks to save yourself a bunch of time and stress? Probably worth it.
Sam Vander Wielen:
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, 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.
Tori Dunlap:
Absolutely.
Sam Vander Wielen:
So really switching into that mindset helps.
Tori Dunlap:
I think there’s this romantic idea that people quit their 9:00 to 5:00 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 net and the backup, backup, backup net and then six parachutes too. So you were meticulous in your planning. What does a realistic timeline and exit plan from a 9:00 to 5:00 actually look like?
Sam Vander Wielen:
I think that’s why it’s so important to know what your personal budget is, right?
Tori Dunlap:
Yes.
Sam Vander Wielen:
So if you’re bougie as shit and you have 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, “What kind of money can you even stash away from now till you quit?” Some people in their 9:00 to 5:00 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 foundational things in getting your business started that you don’t get paid for that you’re not making any money. So register your LLC, get a domain name set up, start getting these little things, get your business a bank account set up, do those little things because those are all a pain in the tush 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 just stash, stash, stash as much as possible.
Tori Dunlap:
You have this three-step process, save, sell, make, that you followed. Can you walk our listeners through that?
Sam Vander Wielen:
Yeah, so I think sometimes people will talk about one of these. 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. So I was cutting my expenses. I was just really buckling down on… Even looking at expenses was funny of what things I was spending money on to make myself happier in my miserable career. And I would think, 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 luxurious lunches every day to just get out of the office. I started bringing my own lunch. It was like $50 at a time and 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. I had a friend who was teasing me and was like, “Oh, what’s the big deal? People don’t really make that much money.” I’m like, “I paid for my domain name. I paid for my LLC. I paid for a bunch of the original startup costs 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 suggest to people is, “Is there anything else you can do to make any more money right now if it’s temporary?” I took on a part-time attorney job just so there was extra income for a short period of time. It was about six months.
Tori Dunlap:
I rightfully think that hustle culture has been so demonized, but what you’re talking about is 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. When I was launching my book, and you’re probably feeling similar, it’s like 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 it 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 you can live this soft life all of the time and still get the things you want. I don’t think that’s true.
Sam Vander Wielen:
Yeah, I completely agree. I actually don’t think… I’ve been in business for eight years and I’ve had seasons where I could pull back, but it wasn’t until the last two years that 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 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.
So I very much believe that not only is a hustle period required, I don’t think it’s necessarily a bad thing. I just think as long as we keep it to the period, I’m 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. I actually miss those days a little bit. I was hungry.
Tori Dunlap:
Oh, they’re fun.
Sam Vander Wielen:
Yeah, I had nothing to lose.
Tori Dunlap:
They’re fun.
Sam Vander Wielen:
I was scrappy. I write a lot about in my book that I think that entrepreneurship requires a lot more scrappiness than people want to talk about too, resourcefulness. I was reaching out, asking for things, really utilizing my resources, just seeing… 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 recommend going into this process as curious as possible. 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.
Tori Dunlap:
Yeah. I was literally just thinking about this yesterday. Taylor Swift just went on this two-year career-defining really intense, really physically, emotionally demanding tour, and now we don’t see her. But that’s the idea. Harry Styles, same thing. Wins the Grammy for Album of the Year, does this massive tour worldwide, and now we don’t see him. And it’s like those are the… You need both. You need both seasons. I’m not glamorizing hustle culture, but I do think hustle seasons are required and you do have to find the fun in them. It can become a game. You have to sprint at times if you want a business to be successful.
Sam Vander Wielen:
Yeah, it’s a funny evolution because I feel like entrepreneurship became my identity, which was pretty fun for a while. I also started in the girl boss era-
Tori Dunlap:
Me too, girl.
Sam Vander Wielen:
… it was at the time. So it was cool back then. But I do feel like it was fun. All of my friends became other online business owners. It was a fun period. And then I feel like the next shift is actually decoupling. It’s like now my identity, I have worked 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.
Tori Dunlap:
What are the four stages that someone’s going to experience when launching their business?
Sam Vander Wielen:
The first business phase that you’ll 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, I could become a health coach or open a flower shop or open a bar studio or be a food blogger.
Tori Dunlap:
Totally.
Sam Vander Wielen:
I’m sure you’re a multi-passionate person. I think everybody 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, again, to this 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 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 and your business. Now, we’re looking at how are we scaling, expanding, hiring, all of that.
And I actually think the final phase is a propagation phase because it’s really, it’s probably what I’m in, and you keep going back to of, 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? All of that.
Tori Dunlap:
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?
Sam Vander Wielen:
Absolutely. Yes, absolutely. So I really recommend a nice blend of something that you’re interested in because I want you to be interested in it and 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. It’s like, I don’t know who does. That would be really weird in my opinion. But what I do-
Tori Dunlap:
My life’s passion is legal templates.
Sam Vander Wielen:
Yeah. Contracts are-
Tori Dunlap:
Incredible.
Sam Vander Wielen:
… 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, I just happened 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, “Oh, I’m starting this thing.”
So I think it’s a nice marriage of thinking about what you really like doing and where is there 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 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 was that mix of 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 something that was a little different. And so I like to think of it as building a recipe in that case.
Tori Dunlap:
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.” 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?
Sam Vander Wielen:
Yes. And then, as I talk a lot about in my book, actually be different. My mom used to always say, “Be interested and interesting.” And you have to actually be an interesting person and then show that part of yourself in your content. 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.
Tori Dunlap:
Okay, we can’t not talk about some legal stuff. When does a business actually need an attorney?
Sam Vander Wielen:
Nowadays, a lot of people don’t necessarily need an attorney starting off. I hope that that’s what I help a lot. I’ve helped over 350,000 people start online businesses. Most of the 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 obviously-
Tori Dunlap:
Sam, can I pause you right there?
Sam Vander Wielen:
Yes.
Tori Dunlap:
Because I’ve talked with, same, 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 does getting an LLC actually cost and actually mean? Because I think it’s going to blow everybody’s minds.
Sam Vander Wielen:
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 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 what I do to be access. I just want to give people access because this is so easy, you guys.
Tori Dunlap:
Totally.
Sam Vander Wielen:
You can all do this.
So depending on where you live, LLCs typically cost anywhere from $50 to a couple of hundred dollars. The only exception to this, or the major exception, I should mention, is in California where we have to file this, what’s called a franchise tax when you also file for an LLC, which costs $700. And it’s an additional expense, but typically-
Tori Dunlap:
But worse comes to worst, we’re talking $1,000, but I think in Washington state-
Sam Vander Wielen:
That’ll be a lot.
Tori Dunlap:
… it’s a couple hundred.
Sam Vander Wielen:
Yeah. In Jersey and Pennsylvania, where I’m from, it was like $125, $175. 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 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 of 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 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 of that kind of stuff. But a lot of people that I’m dealing with who are starting such small businesses, that’s a lot. I am very much a fan of let’s get the foundation set. And then I always say to my customers, “When you become Amazon, if you want to do that, then you go get the lawyers.” That’s when you’re on your way. So I think that it’s overkill when you’re starting out, for a lot of people.
Tori Dunlap:
And I will confess this on mic, I don’t think we did trademarks until maybe 2021 and everybody-
Sam Vander Wielen:
Yeah, a lot of people don’t [inaudible 00:31:10].
Tori Dunlap:
The podcast was already a thing. I already had a million followers. So 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 write-offs. 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?
Sam Vander Wielen:
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 financially on the hook for anything that happens in your business. And then I always say that 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 a lawsuit would cripple most businesses, so we don’t want that to happen. So it can be very beneficial to you on the just 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. 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, let’s say you work a 9:00 to 5:00 or you have a partner and you file 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.
Tori Dunlap:
And again, to that, I’m a freelancer, I’m not an entrepreneur, if you have a 9:00 to 5:00 job and you do any sort of work outside of that for yourself. So that could be, “I’m a 1099 contractor who teaches yoga. I am a graphic designer in my 9:00 to 5:00, 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.
Sam Vander Wielen:
Yeah, 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, all of the things that you’re using-
Tori Dunlap:
Your Wi-Fi.
Sam Vander Wielen:
… to heat that space. Yeah, Wi-Fi, phone, all of that kind of stuff. So 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.
Tori Dunlap:
Totally.
You have a quote in the book, “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 beginning 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.
Sam Vander Wielen:
Because you’re in for a wild ride if it is, because it’s a roller coaster. 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, 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. I still had stressors. It’ll be a wild ride.
But also, 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, “Eh.” I know you get the same thing. It would be very difficult. But I hope, 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.
Tori Dunlap:
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 on 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 gravestone.
Sam Vander Wielen:
Yeah, like Tori had however many millions of followers. 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.” I am going through my own existential crisis where I’m like, “None of this matters. This is not who I am.”
Tori Dunlap:
Well, and you and I had talked when we met that it happened to you, and I’m so sorry for your loss, you at that moment and then your near-death airplane moment of these wake-up calls. I think a lot of women either experience these wake-up calls and 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?
Sam Vander Wielen:
I think the first thing is just a shift in the mindset of everything is an opportunity. And I know I already had my business, but it was still pretty early on. 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, well, what do we do now? And it became a curiosity open point for me. It was just like, well, my business is way too reliant on me. I saw that 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, talk about another hustle period, 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 I think seeing those things is 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?
Tori Dunlap:
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, I very severely disappointed them. How do we get over the fear of disappointing others, whether it is starting that business, growing at 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?
Sam Vander Wielen:
Yeah, what a great lesson to learn too, because as a business owner, you’re going to disappoint people all the time.
Tori Dunlap:
Constantly.
Sam Vander Wielen:
Yeah. Even when you do things perfectly, you nail it and someone’s still pissed off. It’s just the way the world works.
So I think it’s really important to remember that when you start a business or I think make any life change, if you told people you were going to get divorced or cutting off all your hair or whatever, people project all their stuff onto you. And this is especially true about people who care about you and people are worried about your safety. So it’s like they mean well, but people start spewing all their stuff onto you, and it’s their feeling of insecurity of 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 that you’re throwing your life away, throwing this stable job away.
So I think it’s just recognizing that that’s a bit of what’s going on. At least that’s helpful for me, is, oh, this is your thing that would make you really uncomfortable, but I’m deciding to do that. It’s probably also just like there’s no way of getting around it of saying 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, “Do you know how many businesses fail in their first year? And 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… 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 escalating the business you already have only if everybody is super nice and supportive. Because when you get to Tori’s size and you start getting messages and comments on your stuff all the time, you’re going to have to have some thick skin, man. It’s like my friend always talks about being a tree and that we have to be like a tree and further and further grow our roots and really cement our roots because then when the wind blows, the tree is not going to fall over. But if you just 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 it’s my job to keep working on myself and be more and more cemented in what I’m doing. I can’t get it from everybody else.
Tori Dunlap:
I don’t know why I didn’t think about it until you just said it. I was talking about disappointing people before you’re starting your business or as you’re growing it. You’re so right that 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, 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.
Sam Vander Wielen:
Yeah, absolutely. Not getting that affirmation-
Tori Dunlap:
Validation.
Sam Vander Wielen:
… from other people. And I think you’re right. You’re also going to piss off and disappoint people when, 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.” I got it all. “You spent so much time, so much money, so much… And this is what you wanted.” I don’t want it anymore.
So I think what I’m trying to say is 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. That disappointment doesn’t go away. It shifts from being other people, listeners, people in your inbox, whatever.
Tori Dunlap:
And you’re allowed to change your mind when you have new information. 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. Seven-year-old me didn’t understand what rent costs. 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 didn’t really exist actually when I was seven years old. You’re allowed to change your mind when you get new information.
Sam Vander Wielen:
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, it doesn’t matter.
Tori Dunlap:
Totally. So you’ve created this sustainable multi-seven-figure business. What does sustainability actually mean to you now?
Sam Vander Wielen:
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 I try not to run off and do… Everyone’s saying, “You have to do this.” I just stay steady. And I’ve weighted out so many trends, so many things that people have said you had to do or couldn’t do. And I just think slow and steady has won the race so far.
Tori Dunlap:
My last question for you. What does success look like for somebody in their first year of business?
Sam Vander Wielen:
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, if they had kept at it, 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, I think that if you can get through that first year, getting some experience under your belt, just really seeing this all as… It’s like you’re in an internship and you’re just trying. You’re literally learning how to become a marketer, a copywriter. You’re your own legal team, your financial team, you’re everything, your customer service representative.
So you’re just trying it all, and 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 as that opportunity to start acting like I was headed in the place I wanted to go.
Tori Dunlap:
I think that’s such good advice. Sam, thank you for being here. Plug away, my friend.
Sam Vander Wielen:
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.
Tori Dunlap:
I love it. Thank you so much.
Sam Vander Wielen:
Thank you. Thanks so much for having me.
Tori Dunlap:
Thank you for listening to Financial Feminists, produced by Her First $100K. If you love the 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 http://herfirst100k.com/ffpod.
Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristen Fields and Tamisha Grant. Research by Sarah Sciortino. Audio and video engineering by Alyssa Midcalf. Marketing and Operations by Karina Patel and Amanda Leffew. Special thanks to our team at Her First 100K, Kailyn Sprinkle, Masha Bakhmetyeva, Sasha Bonar, Rae Wong, Elizabeth McCumber, Daryl Ann Ingman, Shelby Duclos, Meghan Walker, and Jess Hawks. Promotional graphics by Mary Stratton, photography by Sarah Wolfe, and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First 100K community for supporting our show.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over five million women negotiate salaries, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of over 2.1 million on Instagram and 2.4 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.
