The $500,000 Mistake That Taught Me to Trust My Gut
I ignored my instincts, did what everyone said was the “right” thing to do, and it ended up costing me over half a million dollars.
Sometimes the biggest lessons don’t come from our wins — they come from the moments we wish we could redo. In this episode, I’m opening up about one of the most expensive mistakes I’ve ever made: how I gave away control of my business by not trusting myself, and how I rebuilt that self-trust piece by piece.
What You Need to Know / Key Takeaways
1. The “right” way isn’t always the right way
When Financial Feminist first launched, it became an overnight success — and with that success came a flood of advice. I was told that if I wanted to be taken seriously, I needed to sign with a big podcast network, hire a major agency, and let the “experts” handle it. So, I did what I thought I was supposed to do.
The problem? What’s right for others isn’t always right for you. By trying to follow an industry formula, I ignored what I knew in my gut — that I could build this on my own terms.
2. Outsourcing your power comes with a cost
When we signed those deals, I lost more than creative control — I lost transparency in my own business. We weren’t talking directly with sponsors anymore, we couldn’t control ad placements, and decisions that should’ve been ours were suddenly being made by other people.
Those choices cost us 40% of our revenue — nearly half a million dollars — and, more importantly, the direct connection I’d worked so hard to build with my audience.
3. Credibility means nothing if it costs your authenticity
So many of us chase credibility — the title, the partnership, the shiny badge of legitimacy. But credibility that comes at the expense of your values isn’t worth it. I had to remind myself that I didn’t build Her First $100K by waiting for permission. I built it by being myself and being unapologetically transparent about how the system really works.
4. Rebuilding self-trust takes time
When you realize you’ve been ignoring your gut, it can feel embarrassing or even shameful. But self-trust isn’t something you lose forever — it’s something you rebuild. For me, that looked like bringing everything in-house. No more middlemen, no more waiting for someone else’s approval. My team and I now manage everything — production, partnerships, creative — ourselves. We took back ownership of our time, our money, and our mission.
5. Independence is worth the work
Running an independent show isn’t easy. It means more logistics, more responsibility, and sometimes more uncertainty. But it also means freedom. Freedom to make decisions that align with my values. Freedom to protect my team’s time and energy. Freedom to prioritize quality over quantity — and to serve our community in the way we know best.
6. Learn from your mistakes — don’t live in them
Mistakes are part of growth. What matters is what you do after. I could’ve kept going with the same system because it was “working,” but I was tired of giving away power that was rightfully mine. When you know better, you do better — and this entire experience reminded me that trusting myself is never the wrong move.
Notable Quotes
“There is nobody better at representing me than me. There is nobody better at representing Her First $100K than me.”
“When you trust your gut, you stop outsourcing your worth — and start owning your life.”
“Don’t build your life on land that someone else owns and expect them to care about your house as much as you do.”
Episode At-a-Glance
≫ [00:00] The mistake that cost me $500,000
≫ [08:30] Losing 40% of our revenue overnight
≫ [12:30] The decision to take back control
≫ [14:00] What running everything in-house has taught me
≫ [17:30] How to start trusting yourself more
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Transcript:
Tori Dunlap:
It took me three years to learn what I’m telling you in this episode and it cost me over half a million dollars and today I’m teaching you how to avoid it in just 20 minutes. Let’s get into it. So let me tell you what happened. We have to start at the beginning. I hear it’s a very good place to start. So Her First $100K, this global multi-seven figure business that I own was not a global multi-seven figure business even five years ago. Her First $100K was just a side hustle. It was the side hustle I was doing in addition to my 9 to 5 in marketing, and in late 2019, around this time actually in 2019, I quit my job to run Her First $100K full time.
Financial Feminist, the podcast that you’re listening or watching to right now didn’t even exist. I did not have a New York Times bestselling book. I barely even had a team. But as the business started to grow in 2020, 2021, I was going viral on TikTok, we were gaining millions of followers. After Financial Feminist season one was released, if you’ve been listening that long, you know that in 2021, we released over I think six or eight weeks the first 12 episodes of the show. It was our test. It was our test to see if the show was working, if people were going to respond to it, and not only did they respond to it, it changed my entire life.
From the time the first episode dropped to 48 hours later, we were the number one business podcast in the world. We also were the only women hosted, women focused show in the business charts not only for that period, that one or two weeks, but for the next year and a half. And I don’t think we left the top 20 of the charts with just 12 episodes. So as the show started getting more traction, especially after we debuted that first season and it was so successful, we got a lot of emails. We got a lot of phone calls. Agencies wanted to rep us. Of course they did. We were on top of the world. We were vibing. We were the only women focused, women hosted show in the top 40 business podcasts. We were continually beating a ton of very well-known podcasters for a show that only had 12 episodes that was recorded with a $99 Amazon mic.
I was told by not just the agents that wanted to work with me, but by every other deal I could see with every other well-known podcast that I admired, that you needed to get an agent and you needed a podcast network. Now, what a podcast network is is a network of podcasts. No, but it’s basically it’s all the ones you’ve heard of like SiriusXM or iHeart or Wondery or Sony. And what they do is they have these different hosts and these different podcasts in their orbit and they are in theory cross promoting the shows, right? So if you listen to, I don’t know, an episode of Armchair Expert, you’re also going to hear an ad, for example, about Monica Lewinsky’s show, both of which are on Wondery.
The appeal with signing with a podcast agency is that there’s some credibility in that, right? Saying like, “Oh, I have this big agency behind me.” Right? “I’m a SiriusXM show.” The second thing is that sometimes those agencies are going to offer you studio time, sometimes at a cost and sometimes for free. They’re going to be able to maybe get you better guests on the show because there’s more credibility. But the biggest reason to sign with one is that they’re going to help you monetize your show. Now, monetization looks different depending on the podcast, but for most podcasts, the biggest way they make money is the ads, right? And you’ve heard them on the show when we talk about Squarespace or talk about Quince or talk about Indeed, that is how we make money for an otherwise free for you product.
Now, other people sometimes do tours or they do Patreons or they do merch, right? There’s other ways to monetize the show, but by and large, that is the biggest way that people monetize their podcast in order to not only hopefully make a little bit of profit, but pay for the cost of producing said show. This podcast, for example, very transparently costs us anywhere from like 350 to $400,000 a year to produce. That’s not cheap. That’s a lot of money. That is to pay and compensate people fairly. That is for studio time when we host in person. That is for equipment and flights to different events, lawyers to look at our contracts, right?
The biggest reason to sign with one of these bigger networks or agencies is that they’re going to hopefully help you make money. Now, they helped us make money. That’s true, but there was a lot of problems with signing with an agency for us. The first one is transparency. We were not in direct communication with our ad sponsors. They were the middleman. We not only went through our agent, but went through our agent, then our podcast agency when dealing with partners. We were not in direct contact with Squarespace, for example. So we weren’t brokering our own deals. Everybody it seems has a podcast now, and a lot of people sign with an ad agency because they’re like, “I don’t want to handle the business side of it. I’ll let them broker the deals.”
But when you’re actually somebody who wants to have control over her own business, wants to make strategic business decisions, is good at making those strategic business decisions, it’s difficult to not know what’s going on and to also have that lack of transparency impact the day-to-day of the business, but also the listener experience for you. Because the second thing that happened is these podcast agencies sell their ads as inventory. So they’ll say, “Hey, we have six podcasts with inventory. Do you want to buy slots on all six?” And they sell them as groups. They sell them as blocks. So rather than maybe cherry picking a great podcast with a certain listenership that’s going to be very aligned with that brand, they might just say, “All of these podcasts are going to work with this brand and this is the inventory we have.”
Now, there’s issues with that, of course. One is that if you don’t like a brand, you don’t make money. We turn down a remarkable amount of money because we only want to work with brands that we believe in, brands that are actually going to provide value to your life, and that would piss off ad networks because they didn’t make money when we turned down deals, even if it was the right thing to do for us. That decision affected their business too. Ultimately, so many people work with agents. There’s really nice agents out there. I really genuinely like the agency and the agents we work with. I also had largely good experiences with the podcast networks that we chose to sign those seven figure podcast deals with.
However, this is where it gets expensive. Agencies take up to 30% of your podcast revenue. That is on top of the 10% you pay to an agent. Now, all of this is going to feel really inside baseball, but we love financial transparency on the show, and for someone who listens to the show even semi regularly, I think it’s important to know how we make money and also how damaging it can be to do all of the right things. We were giving 40% of our revenue to other people. This is pretty common if you’re in media. If you are an actor, it’s similar. You’re giving a percentage to your agent and to your business manager and to a publicist and to a lawyer. This is pretty standard. And this is unfortunately something that is not discussed enough.
Because yeah, I may have signed a seven figure podcast deal and that is great, but overnight my money gets cut by 40%. The other thing is that when performance of our podcast shifted from its norm, whether it was under performing around holidays or over performing some other time, usually like the new year, they had a set amount of money that they were paying to us from the brands based on the performance that they had projected. If the performance did not align, that led to overstocking our show with ads. If you’ve been listening in the last year, you that we have 8 to 10 ads on every single episode. I will go on record. That is too many ads. That was not my decision. It is changing now. We are still going to run ads. We still have to afford to run this show and to produce this show, but that was a poor listener experience. We didn’t have a choice in that.
And finally, the third thing with all of this is that we were told it was the right business decision, not just from a financial standpoint, not just from a profit standpoint, but from a credibility or made it a standpoint. It feels sometimes in this and many industries that unless you have a certain title, unless you know certain people, unless somebody well-known is backing you, you are not legitimate. You can’t get into certain rooms or get certain deals or make certain money without those people or that structure backing you. So that’s what we did. I didn’t trust my own gut, which was like, “Okay, I think I can do this myself. I think we can grow this show ourselves.”
And when things started getting weird, I kept thinking, “No, but this is the way people do it. This is the way podcasts are run.” And you feel this way too. You feel this way a lot. You feel this way when somebody tells you that you need a financial advisor to invest in the stock market because you’re too stupid to do it yourself. We get told this all the time, especially as women. And my not so conspiracy conspiracy theory is that industries are built on making us feel like we’re too stupid to understand. I am faced with this choice as a business owner all the time still, that you need to do certain things in order to be a legitimate business, in order to have the accolades, in order to be in the New York Times, in order to make a certain amount of money.
And some of that’s true. Some of that’s about who you know or who knows you or who is representing you. But I got to tell you, there is nobody better at representing me than me. There is nobody better at representing Her First $100K than me. How could they be? I know this business, this brand, this mission inside and out. I know you all maybe better sometimes than you know yourself. I know our community. I know our team. I know how to show up. And when I didn’t listen to my gut, when I didn’t listen to what I knew would be most successful for us, not what everybody else always did, but what would be most successful for us. It was a poor business decision. It lost us a lot of money.
The realization we had is that we lost over half a million dollars that could have stayed in our business. That’s half a million dollars that could have gone to our team members, could have gone in our savings, could have gone to charitable giving, could have been reinvested into expanding the show. It is so easy to feel this sense of frustration and shame when you’re overriding your gut because you’re being told that’s just how it’s done. That’s what happens. You hand over your power to somebody else. This system works, especially for people who are celebrities or influencers who don’t want to manage the business part of the podcast. But that’s not me. That’s not me. I didn’t want to just show up on a microphone and record for an hour. I care about you all and I care about providing education, and I also care about our team and creating this podcast into not only a valuable and important part of listeners’ lives, but also a profitable thing.
We want to be able to think long-term about the future of this show. So what are we doing differently? Well, we are running everything podcast in-house now, which is honestly a celebration. It’s a massive moment for us. It is, again, a little inside baseball. You might not know why that’s a big deal. Most podcasts, I would say 98% of them do not run their production, their legal, their ad sales in-house, meaning that it is our team at Her First $100K managing all of that. We do not have an agency involved. We’re not on a podcast network anymore. We are doing everything ourselves, which means we get to call a lot of the shots, not every shot, but a way bigger amount of the shots now than we did before.
This is our way that we’re building internal processes. We are building team trust. We are building transparency with you all, but also we are able to decide, “No, that’s too many ads.” Or, “No, we want to take some time off and respect our team’s time and give me a break.” This is such a parallel to so much of what we get asked from you all, which is, how do I own my choices? How do I own my decisions? How do I find a way to not only trust my gut, but to build self-trust in my financial choices, in my career choices, in my relationship choices? This is me building my own self-trust. This is me building self-trust in my team. And this is us continuing to be transparent and build trust with you all.
We are an independent podcast now. The vast majority of podcasts that you listen to are not independent podcasts, and we are really proud of that decision, but we also really need your support now more than ever. This is where if you are listening to this show and aren’t subscribed, which the vast majority of you are, the easiest thing you can do to make sure this show can continually gets produced, that it continues to be valuable and transparent and useful to you, is just by hitting a simple button. Wherever you’re listening or watching right now, hitting subscribe is going to help us more than you know. Sharing the show with friends, leaving us five-star reviews, these are the kind of things that allow us to show up.
Imagine we are your local independent bookstore, because for all intents and purposes, that’s kind of the best metaphor. We are competing with Amazon actually quite literally because Amazon owns Wondery. We are literally competing with multi, multi, multi, multi-billion dollar behemoth Amazon. This is where we need your support. We need your business, we need your listenership. We need you talking about us with friends. We need you subscribing. That would be so, so helpful. If you’ve ever gotten an ounce of value from this show, this is how you can support us in this journey.
Learn from my mistake. learn rom my half a million dollar mistake. And I also want to be transparent to show you that even somebody that you might turn to for advice and guidance and see as an expert continually makes mistakes, does things that she knows now were not the right call. They were the right call at the time, and now I have more information. And Maya Angelou always says, “When you know better, you do better.” So my prompt for you, what is one area where you can get more curious, more present, and to take more ownership starting today? Maybe that’s with your debt. Maybe that’s with your taxes. Maybe that’s with your plan to get where you want to be, both financially, emotionally, psychologically, physically in the next year.
Mistakes are part of this journey. What matters is that you don’t keep making the mistake because you’re too afraid of the upheaval in your life. It would’ve been very easy for myself and our podcast producer Kristen and the rest of our team to just keep doing what we were doing. We could have said, “You know what, it’s not completely broken, so why fix it?” But we frankly just got tired of somebody else controlling our life. We got tired of other people telling us what we could and couldn’t do. I need you to get tired of people telling you what you can and can’t do. What matters is that you learn from your mistakes and you focus on how you can grow.
So do not blindly follow industry advice. Do not check out of your money. Don’t build your life on land that somebody else owns and expect that they’re going to care about the house you’re building more or as much as you do. Learn from our mistakes. And this is the time, especially while the world is a mess and Donald Trump hates shows and media like ours where we need your support. Other feminist companies and shows need your support. Learn from our mistakes, support the kind of companies you want to see more of. We appreciate you being here. 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. Researched by Sarah Shortino. 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 Bachmetyeva, Sasha Bonnar, Ray Wong, Elizabeth McCumber, Darrell 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.
