257. This Mistake Cost Me $500,000

14 Oct 2025 · 22 min · 11 chapters

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In short

Tori Dunlap (Her First 100K / Financial Feminist) explains a costly podcast business mistake: signing with podcast agencies/networks instead of running production, ad sales, and legal in-house, which she says cut revenue by ~40% and forced too many ads (8–10 per episode) when performance projections didn’t match reality. She claims the lack of transparency, “ad inventory” bundling, and paying agency fees led to over half a million dollars in lost value.

Guest backgrounds

No guests appear in the transcript; only internal team credits (e.g., producer Kristen Fields).

Key claims

agencies take up to 30% plus an agent fee (~10%); projected ad payments can cause “overstocking” ads; self-representation beats relying on intermediaries.

Notable examples

turning down brand deals she didn’t believe in; switching to in-house operations; competing with Amazon/Wondery (owned by Amazon).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Costly Mistake

0:14 to 0:45

Discussion of the significant financial loss experienced over three years.

“Heat up your 4th of July at the Home Depot with our wide variety of grills under$300 and make every gathering one to remember.”

The Costly Mistake

0:51 to 1:34

Discussion of the significant financial loss experienced over three years.

“One of the things that so many business owners believe they need is a custom bespoke website that they have hired somebody to code for them.”

From Side Hustle to Full Time

1:34 to 2:34

The journey of transitioning from a side hustle to a full-time business.

“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.”

Going Viral and Rapid Growth

2:34 to 3:39

Details of the podcast's success and growth trajectory after launching.

“From the time the first episode dropped to 48 hours later, we were the number one business podcast in the world.”

Agencies and Networks: The Appeal

3:39 to 6:01

An exploration of the role of podcast agencies and networks in monetization.

“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.”

The Challenges of Agency Partnerships

6:01 to 8:04

Discussing the problems faced when signing with podcast agencies.

“is that they're gonna hopefully help you make money.”

The Cost of Representation

8:04 to 9:11

Insights on revenue sharing with agents and the impact on finances.

“money when we turned down deals, even if it was the right thing to do for us.”

Lessons Learned from Financial Decisions

9:11 to 13:15

Reflections on the mistakes that led to substantial financial losses.

“This is pretty common if you're in media.”

The Importance of Self-Representation

13:15 to 14:17

Emphasizing the need to trust one's instincts in business decisions.

“gone in our savings, could have gone to charitable giving, could have been reinvested into expanding the show.”

Transition to Independent Podcasting

16:23 to 18:24

Discussion on the transition to running the podcast in-house and its significance.

“Well, we're running everything podcast in-house now, which is honestly a celebration.”
Show all 11 chapters

Learning from Mistakes and Building Self-Trust

18:26 to 21:13

Exploring personal mistakes and how they relate to self-trust in financial decisions.

“this show continually gets produced, that it continues to be valuable and transparent and useful to you, is just by hitting a simple button.”
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Transcript

Automatic transcript. May contain errors.

0:00Tiffany Aliche: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.

0:13Tiffany Aliche:So let me tell you what happened. We have to start at the beginning. I hear it's a very good place to start. Heat up your 4th of July at the Home Depot with our wide variety of grills under$300 and make every gathering one to remember. Give your outdoor space a glow up. Whatever your budget is, the savings on seasonal plants starting at$5. With the grill fired up and your backyard set to perfection, you'll be able to invite friends and family over to kick off the party. Start celebrating with low prices guaranteed at The Home Depot. Prices may vary by store. Exclusions apply. See homedepot.com slash price match for details.

0:48Tiffany Aliche:This podcast is brought to you by Squarespace. One of the things that so many business owners believe they need is a custom bespoke website that they have hired somebody to code for them. And I'm here to tell you that, yeah, you need a website that's functional and beautiful, but you don't need to pay somebody to code. This is where Squarespace comes in. When I first started Her First 100K, I turned to Squarespace. They were the first investment I ever made in our business to start and grow. And they had so many incredible tools baked in. You can buy domains on Squarespace. They have SEO tools that you can use to get seen.

1:20Tiffany Aliche:And they have cutting edge design tools that don't require you to know anything about code. Head on over to squarespace.com for a free trial. And when you're ready to launch, use offer code FFpod to save 10 % off your first purchase of a website or domain. 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 nine to five in marketing. And in late 2019, around this time actually in 2019, I quit my job to run her first 100k full time.

1:58Tiffany Aliche: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.

2:37Tiffany Aliche: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 like 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.

3:18Tiffany Aliche: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.

4:02Tiffany Aliche: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 serious XM show. The second thing is that sometimes those agencies are going to offer you studio time, sometimes at a cost and sometimes for free.

4:48Tiffany Aliche: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, right? 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.

5:36Tiffany Aliche:This podcast, for example, very transparently costs us anywhere from like$350 ,000 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 gonna 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.

6:17Tiffany Aliche: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 are 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.

7:08Tiffany Aliche: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 like 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 turned 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.

8:03Tiffany Aliche: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 worked 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 this show.

8:54Tiffany Aliche:And for someone who listens to this 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 are giving 40 % of our revenue to other people. This is pretty common if you're in media. If you're 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%.

9:39Tiffany Aliche:The other thing is that when performance of our podcast shifted from its norm, whether it was, you know, underperforming around holidays or overperforming 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 know that we have eight 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.

10:23Tiffany Aliche: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 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.

11:10Tiffany Aliche:So that's what we did. I didn't trust my own gut, which was like, you know, 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.

11:56Tiffany Aliche: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.

12:44Tiffany Aliche: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.

13:26Tiffany Aliche: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.

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14:50Tiffany Aliche:Built Points have also been ranked by top publications as the industry's most valuable point currency. Your housing payment is already your biggest expense. Make it your most rewarding. Find the card that fits your lifestyle and apply today at joinbuilt.com slash sfpod. That's j-o-i-n-b-i-l-t dot com slash ffpod. Make sure to use our URL so they know we sent you. Terms and limitations apply. Subject to approval and eligibility, Built cards are issued by Column N.A., member FDIC, pursuant to license from MasterCard International Incorporated. This podcast is brought to you by Squarespace. I know we've talked about Squarespace a lot on the show, but it's because they're really, really great.

15:26Tiffany Aliche:If you have never interacted with a Squarespace website, you actually have because there's so many websites that are built on Squarespace. But if you are somebody that is getting started, I encourage you to just take a look because their templates are beautiful. They're really easy to use. You can actually offer services through Squarespace and get paid so you don't have to use a third-party payment platform. Squarespace has already got you covered. You can sell content on Squarespace. They also have great analytics so you can see where people are coming from and review website traffic. We love Squarespace and we really think you'll love them too.

16:00Tiffany Aliche:And whether you're just starting out or scaling your business, Squarespace gives you everything you need to claim your domain. So you can showcase your offerings and get paid and grow your brand all in one place. Go to squarespace.com slash FFpod to save 10 % off your first purchase of a website or domain using that code FFpod. Squarespace.com slash FFpod. So what are we doing differently? Well, we're 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 HerFest100K managing all of that.

16:54Tiffany Aliche:We do not have an agency involved. We do not, 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?

17:40Tiffany Aliche: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 continually gets produced, that it continues to be valuable and transparent and useful to you, is just by hitting a simple button.

18:39Tiffany Aliche: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.

19:14Tiffany Aliche: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 from 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.

19:50Tiffany Aliche: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 have been very easy for myself and our podcast producer, Kristen, and the rest of our team to just keep doing what we were doing.

20:32Tiffany Aliche: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.

21:13Tiffany Aliche: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 slash quiz for a free personalized money plan.

21:55Tiffany Aliche:Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristen Fields and Tamisha Grant. Research by Sarah Shortino. Audio and video engineering by Alyssa Midcalf. Marketing and operations by Karina Patel and Amanda LeFew. Special thanks to our team at Her First 100K. Kaitlyn Sprinkle, Masha Bak-Mikyeva, Sasha Bonar, Ray Wong, Elizabeth McCumber, Daryl Ann Ingman, Shelby Duclos, Megan 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.

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From the publisher

It took me three years — and more than half a million dollars — to learn this lesson.

In today’s episode, I’m breaking down the biggest business mistake I’ve ever made: ignoring my gut, following “expert” advice, and paying the price. We’re diving into what happens when you give away your power for credibility, why trusting yourself is the best business strategy, and how to rebuild self-trust after a big mistake.

If you’ve ever been told, “That’s just how it’s done,” this episode will remind you that sometimes the best thing you can do is trust your instincts — even when it goes against the norm.

You’ll learn:

Why “industry standard” doesn’t always mean right for you

The true cost of outsourcing your power

How to rebuild self-trust in your money and business decisions

In this episode:

00:00 — The mistake that cost me $500,000

03:00 — What it means to sign with an agency or network (and why it’s risky)

05:00 — Losing transparency and control in my own business

07:00 — When credibility costs more than it’s worth

08:30 — The moment I realized I’d given away 40% of my revenue

10:00 — The danger of doing things just because “that’s how it’s done”

13:30 — What running everything in-house has taught me

14:00 — The deeper lesson: self-trust, transparency, and ownership

16:00 — How to support independent creators and shows like this one

17:00 — Learning from mistakes without shame

17:30 — The challenge: where can you trust yourself more?

To get more resources including any freebies mentioned in this episode, head to https://herfirst100k.com/ffpod
Learn more about your ad choices. Visit megaphone.fm/adchoices

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