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When I started my business, I had just $40 in my bank account.
No trust fund, no corporate safety net, just a dream and a whole lot of grit. Fast forward, and that $40 has turned into a multi-million dollar company that’s helped over five million women change their relationship with money. But it didn’t happen without mistakes––and a lot of hard lessons along the way. In this episode, I’m pulling back the curtain on the seven most important lessons I’ve learned over nine years of building Her First $100K. These are the strategies, mindset shifts, and sometimes counterintuitive moves that have made the biggest difference—not just in our bottom line, but in my life as an entrepreneur. Keep reading if you want to start a business, are just starting your side hustle, or scaling your dream into a sustainable business––these lessons will save you money, time, and unnecessary stress.
Here are the 7 lessons you need to know:
1. Trying to be everything to everybody makes you nothing to nobody.
Casting a wide net feels like the smart move when you’re starting out, but in reality, it dilutes your message and confuses your audience. Clear positioning attracts the right people who will become loyal customers and brand advocates—and repels those who aren’t a fit (saving you from refunds, complaints, and wasted time).
2. Done is better than perfect.
Perfectionism isn’t a badge of honor—it’s fear in disguise. Spending too much time perfecting your logo, website, or color palette delays real progress. The only way to learn is by doing, and the faster you launch and iterate, the faster you grow.
3. Sometimes you have to quit the good to get to the great.
Killing her best-selling product—1:1 money coaching—was one of Tori’s smartest moves. By pivoting to workshops and then scalable courses, she freed up her time, reached more people, and laid the groundwork for her bestselling book. Short-term discomfort often leads to long-term growth.
4. People don’t need the “expert of all experts.”
You don’t need to be a Nobel Prize winner or have decades of experience to teach or serve your clients. Being just one or two steps ahead makes you relatable and approachable—and authenticity builds trust faster than a flawless image ever could.
5. Stop taking advice from people who’ve never been where you want to go.
Well-meaning friends, family, or colleagues may unintentionally steer you away from your dreams. If they haven’t walked the path you’re on, their advice might prioritize safety over growth. Learn to filter feedback and trust your vision.
6. Be the squeaky wheel that gets the grease.
Opportunities rarely land in your lap—you have to ask (and ask again). Strategic persistence, or “polite badgering,” keeps you top-of-mind for when the right moment comes, even if it’s years later.
7. Systems beat virality every time.
Going viral is exciting, but without systems to capture and nurture that attention, it won’t translate into lasting revenue. Focus on moving your audience from borrowed platforms (like social media) to owned ones (like your email list) so you control the connection.
Notable quotes
“Trying to be everything to everybody makes you nothing to nobody.”
“Perfectionism is fear in stilettos—and it’s keeping you broke.”
“Your parents’ safest advice might be the worst thing for your business.”
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Transcript:
Tori Dunlap:
I started my business with just $40. Now it is a multi-million dollar business. Here are the seven lessons every entrepreneur needs to know if they want their business to grow and succeed, and number five is a game changer. Welcome back to Financial Feminist. I’m Tori. I’m a multi-millionaire, a money expert, and I’ve helped over five million women be better with money. And today on the show we are talking about all of the things I wish I knew when I built my business. This episode alone can save you thousands if not hundreds of thousands of dollars over the course of you building your business plus so many hours in wasted time because there are so many mistakes I made as an entrepreneur. There are so many things that I wish I knew that somebody should’ve told me but didn’t, and this is the episode that you need that’ll walk you through every single thing that I wish I knew when building a multi-seven-figure business. But first, a word from our sponsors.
My first lesson, trying to be everything to everybody makes you nothing to nobody. When you’re first starting a business, what happens is that you need money, you need clients, and so you cast a very broad net. You’re like, “I’m going to appeal to people in every single city of every gender identity of every age and every need,” and what happens is that somebody goes on your website or somebody goes on your social media and they don’t really know if your product or service is for them. So you don’t earn their business at all because you try to be everything to everybody. It’s counterintuitive, right? You think, “I’m going to start this business. I want as many customers as possible. Why would I ostracize people? Why would I be clear when my product isn’t for others?” Well, we do this for two reasons.
One is that the girls that get it, get it, and the girls that don’t, don’t, right? The people who understand and love your business are going to be all in. They’re going to be total brand evangelists for you. If you follow us at Her First $100k, you know that this company, this business is definitely not for everybody, right? If you are someone who is off by the word feminist, you’re probably not going to have a fun time here That doesn’t actually lead to less customers. It leads to more devoted people who are going to buy from you and support you time and time again.
The second reason that trying to be everything to everybody does not work is that if you do get people who aren’t in your target audience to buy your product or buy your service, they’re probably not going to be happy with it. They’re going to be dissatisfied customers, and so yeah, we may be got their sale once, but we will not be getting their sale again, and we’re probably going to have to issue them a refund because the thing that we’re selling is not for them. So the number one thing that I need you to understand, especially in your marketing for your business, is it’s okay to piss people off. Don’t do stupid shit. Don’t be controversial just for the sake of being controversial, but it’s okay to have an opinion. It’s okay to take a stand. It’s okay to say, “Yeah, this thing isn’t for everybody,” so that when someone comes to your social media, your Instagram bio, your website, somebody immediately knows, “Yes, this is for me. This can add value to my life, or no it can’t.”
Number two, my second lesson, if I could tattoo this on every entrepreneur’s forehead, I would, done is better than perfect, 100%. The thing that you are believing is that you need to have the perfect logo and the perfect website and the perfect brand color, maybe before you even start. And you think it’s you being productive, you think it’s you doing the right things. You’re like, “I can’t launch this brand until I have all of those things,” but in actuality, you’re putting these make-believe hoops in front of yourself as a way to feel like you’re doing stuff when you’re actually just letting fear get in the way.
One of my favorite quotes of all time is from Elizabeth Gilbert that perfectionism is fear in stilettos. And especially for women, we are believing that perfectionism is a badge of honor. It’s something to be proud of. It’s not. It is not. I need you to get rid of your perfectionism if you want to be a good entrepreneur. If you want to be successful, if you want to make money, if you want to make an impact, you have to let go of perfectionism because that is fear actively holding you back. That fear is what if somebody realizes that I don’t know what I’m doing? What if I fail in front of everybody? What if I post on social media and I’m cringy? What if the logo, I look back in four years and it looks terrible?
All of those things are true for me, by the way. I look back even two years ago at the content I was posting or what our website looked like, and I’m like, it’s not good, but you have to start somewhere. And you only learn how to be a good business owner by running the business. I know that seems obvious, but so many people think, “Oh, I can run the entire business from my head. I can design the website. I can do all of these things, and that’s how I’m going to learn.” No, you’re going to learn by doing. And every time I get caught up in that perfectionist mindset, I can draw a direct link from that mindset to our business not making as much money or not making as much of an impact, or us wasting so much time trying to make decisions. Just make a decision. You figure out later if it’s the right one. Done is better than perfect.
My third lesson for you, sometimes you have to quit the good to get to the great, and let me tell you a story of what this looks like. When her 100k was a side hustle, I was running Her First $100k on the side of my nine to five in marketing. This was 2019, so not that long ago, and I was trying to figure out how to quit my job. I was trying to figure out how I could quit my job to run this business full-time. So every day I was trying to figure out, one, how to manage my time, but two, how to make strategic decisions to get me from where I was to where I wanted to go.
And at that time, I was doing one-on-one money coaching. I was sitting down with people at coffee shops in Seattle and having full one-on-one conversations with them where I was doing budgeting audits and helping them navigate open up a Roth IRA. And I realized that was a great moneymaker for me where I’m at now, but long-term, it was not sustainable. I was making probably a couple thousand dollars a month doing money coaching, which was pretty decent income, but if I wanted to quit my job to go full-time on my business, I needed a lot more time to actually work on growing the business. I was too much and being my own product of taking time to do these one-on-one coaching sessions that I knew for the strategic long-term sustainability of this business that was not going to work out, but it was also a stupid decision. What am I going to do? Kill my best-selling product? Yeah, I did. I killed my best-selling product.
The reason I did that, the reason I stopped doing one-on-one money coaching was because I knew that the sustainability and the long-term lifespan of the business was not going to work. It was not going to actually get me to the point where I could quit my job because it was taking up too much of my time, and it was good. It was good money, it was interesting work, but it was not sustainable. So I killed my best-selling product. I stopped doing money coaching. One-on-one money coaching, no longer available, but I pivoted. I realized that 90% of the questions I was getting asked in coaching were the same. It was about how do I create a budget and what should my financial goals be in what order?
So I took all of my learnings from one-on-one coaching, which was almost like a paid beta test, and I said, “Okay, I’m going to make a workshop. I’m going to make a 45-minute personal finance 101 workshop with a 15-minute Q&A at the end so I could teach a lot of people in just that one hour.” And that’s what happened. I would get 30, 50, sometimes 100 people signing up for that workshop. I would run it about once a month, and that way I was able to serve a lot of people in a shorter amount of time.
Guess what I did after that? The workshops were no longer sustainable. The workshops became a passive course. It became our back to basics course that we sold, and if you’re an oldie but a goodie, you remember that. It was like our signature product. It was personal finance 101. Everything that I learned from running those workshops, from doing that coaching went into the course. And guess what? After a year of doing that course, the course was the foundation of my book Financial Feminist, which is a New York Times bestseller that has sold nearly 300,000 copies. So sometimes you have to quit the good to get to the great. Sometimes you have to make strategic decisions that feel really stupid in the moment, but actually benefit you and benefit the business long term. When we come back, I’m diving into more lessons I’ve learned over the past nine years of running my business, including how to show up to make the biggest impact in your business. Stay tuned.
Welcome back to the show. Thank you for supporting our sponsors who allow us to do this content for you for free. Okay, number four, my fourth lesson, people don’t need a buttoned up expert of all experts. What do I mean by this? Well, when you’re running a education business, and I don’t just mean doing something like I do, financial education or teaching, but I’m talking anytime that you are doing any sort of service in your business that positions you as a thought leader or as an expert, we believe that we need the highest certification. We need to be a Nobel Prize winning person in this field. We believe that we need to be the best to ever do it, and here’s why that’s wrong. The average person does not want to hear from the person who is the best in the business.
I know that feels counter intuitive, but if you are a side hustler right now, yeah, Mark Cuban could give you some pretty good business advice, but Mark Cuban has not been in your shoes for decades. He doesn’t know what it’s like to run your particular business. And you also are probably way too nervous and intimidated by Mark Cuban to actually ask the questions or to get the kind of information that is actually going to make an impact. And so you think, “I need to be the best person at this job. I need to be the person with all the certifications and the degrees and all of the credibility in the world,” when in actuality, you just need to be the person who is one to two steps ahead of the person you’re trying to teach. Why? Well, one, they see themselves in you. You’re not at Mark Cuban level where you’re this God type figure talking to the masses, right? You’re someone who is just slightly ahead. It means that they can do it too because they see themselves in you. They’re more likely to be vulnerable. They’re more likely to actually want to work with you because they can see how you did it. They can go, “Ugh, that’s inspiring. They were just where I was a year or two ago,” and that helps them open up. That helps them want to invest more in your product or service.
The second reason people don’t need the expert of all experts is because a lot of the things that you just take for granted that you just feel like everybody knows, very few people know, and you start to understand this as you teach. This is what happened to me time and time again with marketing. I’m a very good marketer. I think it’s one of the things I do best. I know that a CTA, a call to action, needs to be on-screen for every social media post I do. That’s not an obvious thing for everybody. Not everybody knows that. When I’m teaching Business Boot Camp with my friend Mal, which we’re about to do live, there’s so many times where we’re like, “There’s so much we’re teaching here that is based on how many years of expertise we have that somebody joining might not know.” They might not know exactly how to create a marketing plan that doesn’t make them want to die. They might not know how to strategically think about making enough money while not burning themselves out. They might not know that you have to set aside 30% of your income for taxes as a business owner. That’s a fun fact that you figure out over time, and this is what we’re doing in Business Boot Camp, is teaching you all of the things that we had to find out the hard way and that a lot of people just take for granted.
So people don’t need the expert of all experts. They also don’t need you to be 100% buttoned up. I think one of the reasons that you consume my content most likely is because I’m a real person. There’s a lot of times where I show up in no bra and no makeup. There’s a lot of times where I fuck up my words and we got to just keep trucking, okay? And people value authenticity. They value seeing you as a real person, as someone who makes mistakes, as someone who keeps going through those mistakes. And we know from so many studies that people are more likely to buy from and support entrepreneurs who are not perfect and who are willing to say they’re not perfect, and they’re not all buttoned up and they’re not the absolute pristine version of what we think an entrepreneur looks like. So my fourth lesson, people don’t need the expert of all experts, and they definitely don’t need somebody who’s 100% buttoned up 100% of the time.
All right, my fifth lesson for you, you are taking advice from people who have never been where you want to go, and it’s the reason you are failing. We want to please everybody. We want to please everybody, especially as women. When I first started my business, so many people in my life were supportive because it was a side hustle. It wasn’t a risk. It didn’t feel scary. It was this fun, cute little blog. It was like a cute little hobby that Tori had. And then when the business started becoming more successful, it was on CNBC, posts going viral. I went on Good Morning America for the first time. That’s when I started getting advice from all sorts of people.
And yeah, some of it was good advice. Some of it was from people who were doing the kind of things I wanted to do and who were running the kind of businesses I wanted to run. And then I was also getting advice from people who had no interest in being business owners, who had never run a business, but had a million opinions about what I should do with my life, how I should run my business. And the loudest voice was my parents. I love my parents very much. I think they’ve given me great advice in my life, but one of the most harmful pieces of advice they ever gave me was that when I was on the precipice of quitting my job to run Her First $100k full-time, I had just been on Good Morning America, I had just saved $100,000 at age 25, I had momentum in my business, the business was making good money, they told me that I needed to do everything and anything I had to do to keep my corporate job because their primary goal as my parent is my own safety. That’s it. That is their primary goal as my parents.
Even though I was in my 20s, their motivation is always to keep me safe. And they’re right. The safer option would’ve been the steady paycheck and the lunch office lunch on Fridays and the health insurance, right? That would’ve been the safer option, but it was the worse option. It was the lesser option of the two. And if I would’ve listened to them well-intentioned advice, I would be living a very different life and a life that was not lighting me up and a life that I didn’t have as much money and didn’t have as much purpose and didn’t have as much freedom and choices and options.
My parents had never been where I wanted to go. Neither of my parents were business owners. They didn’t really understand what an online business was. I don’t think my parents still fully understand what I do. And I’ve been at this for nine years. If you’re taking advice from people that you want to please who have never been where you want to be, that’s the reason you’re failing, is you care about what everybody else wants and care about making everybody else happy before you’re making yourself happy. And again, these are well-intentioned people. These could be your family members, your spouse, maybe hopefully kind people on the internet, but it could also be from people who don’t want to see you succeed. And if you’re believing that narrative that they’re trying to feed you, your business is not going to succeed because they don’t want to see it succeed. Your success is a threat to their lack of initiative. Don’t let yourself get caught up in it. Stop taking advice from people who have never been where you want to go.
My sixth tip for you, you need to be the squeaky wheel that gets the grease. My friend Mallory and I just put together our Business Bootcamp Live program. We refreshed it, we’ve redone it. I’m so excited. It teaches you everything you need to know about growing an online business, whether you have an idea, whether you don’t, whether you already have a side hustle, whether you don’t. It’s going to get you from idea to income in 90 days or less. And one of the things we kept coming back to for the reasons we’re successful, she has built multiple companies to six figures before 30 years old. Her First $100k is a multi-seven figure business that turned me into a multimillionaire before I turned 30.
And one of the things that we realized is that we were always a little annoying. We were always a little annoying about what we wanted and so many women, because again, we’re taught that opportunities should just come to us and we can’t be loud and we can’t talk about our accomplishments. That is not going to allow this business to grow. And when we wanted something, whether it was me trying to get on Good Morning America or a feature in the New York Times, or for her being a Lululemon ambassador, we were the squeaky wheel that got the grease because no one cares about your business as much as you do, and you have to bug people. I call it polite, badgering internally with Her First $100k when I talk to my team. You need to politely ask them until you get what you want. Now, I’m not saying go to their office and stalk them every day. I’m not saying email them every day. I’m just saying, if you want something, you have to go get it. It will not come to you. And you have to be a little loud about it.
I’ll give you an example. When my book was coming out, when Financial Feminist was coming out in 2022, even before that, but definitely during that time, I really wanted to be on We Can Do Hard Things, which is the incredible podcast that Glennon and Amanda Doyle and Abby Wambach host, I started dropping seeds. I reached out to them on Instagram. They didn’t see it. They didn’t care. I was pitching them on my Instagram stories and tagging them. I was trying to email them. I was reaching out to anybody that I knew Glennon had blurbed her book that I might have a connection with so that maybe I could… I was trying everything and I did not get on We Can Do Hard Things in 2022. I did get on their producers podcast.
Now, I don’t think she’d mind me saying this. This podcast is way smaller. It is a way smaller show than Glennon, Abby and Amanda’s, but I thought, this is my audition tape for We Can Do Hard Things. If I can show up at this episode and kill it and give really good advice and be absolutely phenomenal, then maybe this can happen. That was 2022 I did that episode. I stayed in their producer’s orbit. I would reach out every once in a while. I would have Kristin, our podcast producer, reach out every once in a while. We were sowing seeds, so the first time they wanted to talk about money on We Can Do Hard Things, it was a full three years later in 2025.
I don’t even know actually if my episode of We Can Do Hard Things will be out by the time we release this episode, but I was top of mind. When they wanted to do an episode talking about money, talking about what I would call financial feminism, they knew about me. I had reached out in a non-annoying way and was very clear about what I wanted. I wanted to be on We Can Do Hard Things. I wanted to be in that orbit. I wanted to show up and provide so much value for the listeners so that when the opportunity presented itself even years later, I was the person they thought of. That’s what we’re talking about here.
When we come back, we’re wrapping up this episode with my last tip for business owners, and this is the one that changed my business in a way that almost no other tip has. Stay tuned.
All right, my final, final lesson for you. This is one that I see countless entrepreneurs make as a mistake. When you are trying to build your business, and I’m going to use social media as the key example here, when you’re trying to build your business on social media, whether it’s you as your personal brand, it’s just your company and your product or service, it’s easy to get caught up in what we call the vanity metrics. How many followers do you have? How viral did a post go? How many views does it have? And virality is great. Don’t get me wrong. I have experienced viral moments countless times over this business. Probably at this point a couple 100 times, our work has gone viral and we are teaching everything that you need to make your work go viral to blow up on social media in Business Bootcamp. We are also though teaching what to do with that virality, and this is what no one teaches.
Virality is great. It’s fun. It’s sexy, right? It is exciting when your aunt is like, “I just saw you on this place,” and you’re watching, literally, you’re just refreshing Instagram and there are more views and more comments every single time you refresh. It’s insane. It’s incredible. But virality is fleeting and it does not equate to actual revenue in your business. You having a post or a moment in your business… And again, I’m using virality here, but it could be getting a big interview. It could be having your favorite influencer talk about your product, right? These moments are fun and exciting, but they do not make an actual impact on the sales and the growth of your business unless you have systems to support them. And that is what we’re teaching in Business Bootcamp. We’re teaching you how to go viral. That’s actually easy. Virality is not that hard. Systems are so much harder.
So in 2021, we were growing on TikTok. We had probably 900,000 followers on TikTok, right? Pretty decent. We have over two million now. 900,000 people were watching our TikTok videos. That’s fun. That’s great. That’s cool to have posts go viral. But I realized I don’t own though that audience on TikTok. I don’t own TikTok’s land, right? I am building my audience on borrowed land. And so if I wanted to actually grow a business that converted people to customers, to podcast listeners, hello to YouTube subscribers, to hopefully make us money there, I had to get them off of TikTok and get them onto land I owned. Actually, YouTube is not even a good example because that’s land you don’t own either. But I wanted to get them on land I owned, okay?
So what I did in 2021 is I worked with my team to build a quiz. You can still see this quiz. It still works. If you go to herfirst100k.com/quiz, you can see how we set it up. We ask you six, seven questions, and at the end, we give you a free personalized money plan in exchange for your email. That’s how we’re building our email list. So 2021, we had a post on TikTok go crazy viral. It got I think six million views in that first week or two. It got written up by the Daily Mail and BuzzFeed and CNBC and a bunch of other places, and the virality was great. It was cool. I got some press out of it. We got some increased followers. I think we got an extra 200,000 followers to our TikTok during that point. All of that was fun, but that doesn’t mean actual money in the business. That doesn’t mean actual customers in the business.
But I did something really smart with that video. I didn’t know it was going to go viral. I had an idea performed pretty well because I have a formula that we’re teaching in Business Boot Camp. But I thought to myself, “How do we incorporate the quiz? How do we get people to take the quiz if they watch this video?” So I very simply in the caption of that video that ended up blowing up, said, “Hey, take the quiz linked to my bio for a free personalized money plan.” In one week, one week, seven days, we got 100,000 email subscribers from an organic video that we did not pay for that I shot without a bra, in a sweatshirt, with a ring light in 10 minutes. You don’t need to be a buttoned up expert. I was in a sweatshirt, no makeup, with a ring light and an iPhone, and I shot it in less than 10 minutes. You don’t need to be a buttoned up expert. You don’t need to be perfect. You don’t need to go viral all of the time. Done is better than perfect. People want somebody they can relate to, and systems are going to beat virality every single time.
Now, here’s what I want you to do. I want you to take one of these lessons and make it your new mantra, okay? If you feel like you need to have letters behind your name or look a certain way to be taken seriously, people don’t need a button up expert. If you feel like you spend too much time on every project because you don’t want to make a mistake or you don’t want to be a fraud, or you just are so scared and letting that analysis paralysis and fear keep you from taking action, done is better than perfect, okay? If you’re feeling tempted to keep everything you do so broad to reach as many people as possible, trying to be everything to everybody makes you nothing to nobody. So use your mantra every time you feel tempted to self-sabotage, to keep yourself from actually playing big, from growing this business sustainably. Repeat this to yourself when you feel yourself playing small, it is a small step, but your mindset. That is your biggest weapon as an entrepreneur- your mindset is the biggest reason you will be successful or not successful, so use it to your advantage.
In Business Boot Camp Live, we have everything you need to know about starting an online business and going from idea to income in less than 90 days. This is a proven formula, both for Mal and I and building six and seven figure businesses, and also both of us helping thousands of entrepreneurs figure out their marketing plan, figure out their business plan in a way that isn’t going to take you hundreds of hours to actually just get started. We have early bird pricing available. You can save so much money doing it this way. We also have a VIP option where you can get coaching and business audits directly from us. You can go to herfirst100k.com/biz-waitlist to be the first to hear when we launch. Biz, B-I-Z, dash, waitlist, to hear everything and to be the first to know what we’re cooking with Business Boot Camp. We so appreciate you supporting Feminist Media for being here, for listening and watching Financial Feminist, and we’ll see you back here very soon. Bye.
Thank you for listening to Financial Feminist a Her First 100K podcast. For more information about Financial Feminist, Her First 100K, our guests and episode show notes, visit financialfeministpodcast.com. If you’re confused about your personal finances and you’re wondering where to start, go to herfirst100k.com/quiz for a free personalized money plan.
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.
