Disrupting the Podcast Monetization Model with Stephanie Postles – EP 192

Interview with Stephanie Postles

Brian Preston

Disrupting the Podcast Monetization Model with Stephanie Postles

In today’s episode, I’m talking with Stephanie Postles, the CEO & founder of Mission, an award-winning podcast network designed to create, publish, and market meaningful experiences that influence the hardest-to-reach executives in the world.

Before launching Mission, Stephanie worked at Fannie Mae and later at Google, where she managed a $1 billion PnL for the Geo business unit and led a $500M+ divestment. Seeking to start her own venture, Stephanie began blogging on Medium, which eventually led to the creation of Mission.

The company transitioned into podcasting and went on to launch more than 35 shows – using proven storytelling techniques to create custom media experiences for their clients.

But the ingenious part of it all is how Stephanie leverages her podcast network to drive revenue. Unlike most podcast owners, who focus primarily on selling ad space, Stephanie came up with a clever approach to teaming up with enterprise level companies, like Salesforce, Twillo, UPS, Dell, and many more – a strategic partnership model that creates a win/win for all involved.

In this episode, you’ll learn:

✅ What Stephanie has discovered about the fickle nature of platform algorithms from producing 35+ shows and hosting 800+ interviews.

✅ How to handle the tricky relationship between show hosts and sponsors — and why selling ads might not be the best monetization strategy for your podcast.

✅ How to value and sell a digital asset like a podcast for a 3x revenue multiple.

Featured on This Episode: Stephanie Postles

✅ What she does: Stephanie is the CEO & Founder of Mission, as well as the host of Up Next in Commerce. Prior to Mission, Stephanie worked at Google where she ate at every restaurant on campus, attended all the product parties, and traveled the world. She also managed a $1B PnL for their Geo business unit (includes Maps, StreetView, Local, etc.), led a $500M+ divestment of a satellite company called Terra Bella, and created a multi year product plan for Google’s camera hardware and augmented reality efforts. Outside of work, she loves being a mom to her 3 boys + 1 wild pup, staying up to date on all things crypto, hiking every trail she can find, and trying out the epic restaurants in Austin. To see and hear Stephanie in action, subscribe to Up Next in Commerce.

💬 Words of wisdom: “Don’t build a company on someone else’s platform. They can literally change the rules overnight and there goes everything.” – Stephanie Postles

🔎 Where to find Stephanie Postles: Instagram | YouTube | LinkedIn | X

Key Takeaways with Stephanie Postles

  • From Corporate Finance to Entrepreneurship
  • The Power of Side Projects and Joining Google
  • From Blogging to Podcasting
  • Insights from Fannie Mae
  • Creating and Scaling Podcasts
  • Unique Revenue Model: Strategic Partnerships
  • Podcast Valuation & Selling for a 2.5X Multiple
  • Content Quality and Sponsor Relationships
  • Diversifying Content: Spirituality, Parenting, and More
  • New Markets and Testing Content Ideas
  • Where to Find Stephanie Postles

A Unique Podcast Monetization Strategy

Inspiring Quotes

Don’t build a company on someone else’s platform. They can literally change the rules overnight and there goes everything.” – Stephanie Postles

Resources

Tax Strategy Masterclass

If you’re interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax

Strategy Session 

For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation

The Lifestyle Investor Insider

Join The Lifestyle Investor Insider, our brand new AI – curated newsletter – FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider

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Read the Full Transcript with Stephanie Postles

Justin Donald: Hey, Stephanie. So good to have you on the show.

Stephanie Postles: Thanks for having me. Excited to be here.

Justin Donald: Yeah. Well, it's fun to kind of go full circle and to give everyone a little bit of backstory. You and I met at a Strategic Coach event. We are at Freezone Frontier, which is their highest tier or ticket item. They have three different tiers. And this one is a room full of, I don't know, 75, 100 people, something like that. I think it's 50K a year and it was really an incredible event, awesome people, great content. I'm such a big fan. I remember sharing at this event. I stood up and I grabbed the mic and wanted to do a share and I basically said for all intents and purposes any group outside of the Lifestyle Investor Mastermind I've never met people so impressive and so incredible. And the community is just great.

And so, you and I, we got a chance to meet, connect. We are sitting across from each other at a dinner. I can't even remember that restaurant. It’s a super fancy restaurant. It’s delicious. And then we Uber to the airport. And I learned your life story. I shared my life story. And we were instantly great friends. And I think I pinpointed the fact that we may have met briefly or in passing at our mutual friend, Jon Vroman’s house.

Stephanie Postles: Yeah. We have lots of friends in common but it took us both going to Florida to a very different event to officially become friends.

Justin Donald: That's right. But it worked out perfect because I had a captive audience in you for what, two hours at a dinner, two and a half, maybe three hours. I mean, it's a long dinner. And so, I got to hear everything. I got to share everything. It was a lot of fun. So, I knew immediately. I'm like, "We got to tell your story.” People need to learn about you and learn about the cool stuff that you did in corporate America, and then how you kind of broke free from that and you started your own business. And more so than just a business like a true passion, a passion project that is a business and all the different podcasts that you started and scaled that you had a podcast that you sold. I mean, we're going to get into all this but I'm curious, how did this all start? How did you go from being a corporate businesswoman to being this amazing entrepreneur and podcaster?

Stephanie Postles: Yeah. So, I mean, my background is in finance. So, if I back way up, I have an investment finance degree. I got my degree in three and a half years, got out quickly, and I really thought I wanted to be in corporate finance. Every day, I would imagine like I'm going to be in this white wall building, super fancy, suits and ties, and like a little garden is going to be around my office. And every day when I was going through school, I literally visualized this. And next thing you know, I'm moving from the eastern shore of Maryland to DC. I have a job at Fannie Mae. And I remember looking up after about two months, I was in this economics and finance group, and I was like, “Uh-oh, I literally manifested myself to this exact spot. And this is not fun.” I don't like corporate finance. I don't like having to learn how to do SQL and pull all this data and create housing reports that everyone's relying on. And I'm 21 years old. I don't really know what I'm writing like this feels like a lot of pressure.

And so, that was the moment when I realized how powerful your mind was and to be careful what you wish for. And things just they were fine there but I just wasn't very happy. And so, that's when a lot of tinkering started on the side. And that had always been a theme for my life. While I have a twin sister, we'd be going to the library when we were in middle school, and she would buy all these like teen drama books and I'd be buying books on like how to start a business and how to do shipping overseas. And just like we had such different interests, but that was always ingrained in me from a pretty early age. And so, started tinkering on the side, and then built some apps, built an iPad magazine, just started trying things and launching things while I was still at Fannie Mae. And I listed them on my LinkedIn because I was like, “Yeah, this stuff I don't really want to like stay in this area in finance forever. So, here's other things I did.” And just by putting my side projects on LinkedIn, that attracted Google to reach out.

Justin Donald: Wow.

Stephanie Postles: Yeah. So, a recruiter reached out of nowhere and she was like, "We are looking to hire for a couple of roles. Your background and that schooling doesn't really matter,” because I went to like a small school on the Eastern Shore. No one really knows of it. It's not known for really anything. And she's like, "But these side projects are interesting.” And so, Google flew me out to their Mountain View, their main location, and I interviewed with six different teams, and I got six offers from all of them. And I ended up choosing the group that felt like the most entrepreneurial, the most chaotic. So, the group that I chose was called Geo and so it was a billion-dollar P&L that I was coming in to oversee, which was Google Maps, Street View, Earth. We were going to acquire a satellite company. It was this huge group that had really not had a finance person before.

So, they were like, “We don't know what you're supposed to do but just make sure you do maybe you're supposed to do and then also, can you help us with all these other things because we want to acquire the satellite company. We don't know how. We don't know if we should get into virtual reality. We don't know how many Street View cars we should have in Japan.” So, it was really this really fun job that was super expansive and I just got to do everything I wanted to. And that was really fun until I started getting the itch again of like I still want to do something on my own and just own it on my own. And so, that's when Mission, the company that I have now, it started as a side project. So, it started as actually just a blog on Medium. And every day, we were putting out stories from just things that were inspiring.

So, we were telling the unknown backstory of people who are changing the world. We would keep their identity hidden until the end. We were telling executive stories. We were telling stories around like the kind of technology, things, and trends that were happening in San Francisco area. And so, really just writing a lot and not getting a lot of traction for a while. We will be putting out so much content and it was like five views, seven views. And so, it took quite a few months until finally we started having traction and our articles started getting views. Next thing you know, we have tons and tons of people writing for us, the best of the best, the Tim Ferrisses, the Benjamin Hardys, all of them are writing for our publication that we built. And that's when things started to kind of take off. We had millions of readers every single month. We had a lot of engagement and started thinking, "This is taking a lot of time. I should figure out how to incentivize myself and monetize it with this big audience.”

And so, struck up a few little ad deals like not much at all, banner ads. So, the second that we started running these banner ads, though, was the second that Medium was like, "You can't do that.” Medium was the one who owned the whole platform. And essentially, they wanted us to work through their ad network that they were building. They didn't like that we had a top publication. They wanted like their company, Medium, to have the top publication on the platform. And so, it got pretty hostile pretty quickly. And that was when I realized we can't rely on other people's platforms. You can't build a company on someone else's platform where they can literally change the rules overnight and there goes everything. And we don't have user data. We don't have emails. I don't even know who I'm talking to.

And so, that was when the shift to podcasting happened. It was more of a forcing function of we need to get out of here. And podcasting, cool and authentic and a great way to tell these stories. And so, made that switch in 2017. At that point, I was still at Google. So, we weren't like there was not enough money being made from Mission at the time to be able to jump full-time. I had one kid. I was pregnant with twins. So, too much risk to jump, at least what it felt like to me, to jump fully knowing that I was also the breadwinner of the house and the only main income earner.

Justin Donald: That's a lot of pressure.

Stephanie Postles: That is a lot of pressure. I know. I was like, "Umm.” Most people are just like, "Just jump. Just do it.” I'm like, "Not when you have about to have three kids under three. Probably not.” And you're living in Palo Alto, like a super expensive area.

Justin Donald: Expensive. Yeah.

Stephanie Postles: Yeah.

Justin Donald: But it's interesting because your side hustles became a primary reason why you were able to pivot and transition from thing to thing. So, it's interesting because while you're at Fannie Mae, and by the way, Fannie Mae, what a great landing spot. I mean, like most people would be thrilled to have that on the resume. For those of you that are unfamiliar, it's a private company but one of the largest. I mean, most people will consider it an extension of the government and it's an agency that subsidizes housing and the sister company to Freddie Mac, and it's a fascinating world but, I mean, like that's a great place to be if you're in the finance game, a great foundation to get started, right? And then you…

Stephanie Postles: Definitely was a fun spot at first to see so much where when you get a peek into what happened in the housing crisis, you're then very timid to over-leverage yourself because you're looking at a book of business that Fannie Mae had acquired, and you're just like, “Okay. I don't want to do that. I don't ever want to have that high of debt compared to my mortgages and take on that much risk.” So, it was also good for that perspective to have access to like, essentially, almost the entire housing markets data because you also got Freddie Mac's data to look at too. So, you had a really big picture into what that looks like and what not to do.

Justin Donald: That's incredible. Yeah. What to do. What not to do? Get your side hustles go and they land you your job at Google. Google, though, like your story of having six different divisions that all wanted to hire you is really cool. And you got your pick of the litter. The one that you thought was most entrepreneurial, most maybe outside the box, but then you start Mission while you're working there and Mission becomes the big thing that you are working on, your big passion project today. Though you have several businesses, Mission is kind of like the parent company to all of it, right?

Stephanie Postles: Yeah. So, Mission is the bigger company that has, I mean, at this point, we've probably built about 35 or 40 different podcasts and video shows. And we just, I mean, essentially the model, I arranged it different because of what I saw happening in media. So, when I came into media, I saw what was happening in the podcasting space, people and companies were launching shows. They would soon die after a couple of months. People were writing a lot of content that was based on fear, uncertainty, doubt. They were really trying to get those clicks, get people to listen, and it didn't feel like it had good incentives behind it. And it didn't feel like it had longevity behind it.

And so, when the company was built, it was built on very different principles of we're going to create this content that's going to inspire, educate, and entertain all at the same time. And we're going to build a model so that we're not fighting for more, but we're fighting for quality and maybe even more niche audiences so that we can attract big sponsors and we can partner with big sponsors like Salesforce and Splunk, and New York Stock Exchange, and Twilio, big enterprises. We want them because we know that they need what we have, and we need what they have. And so, we created a relationship to build out this company that would make it sustainable, profitable, and allow us to create the content that we want and tell the stories that we wanted.

Justin Donald: Well, the content game is a great game and you and I are both in this space. And this is not what I know. I mean, for me, I'm just coming up with stuff. I love to create content because it's fun for me to get in an imaginative state and just really be creative with the way I look at the world, the way I look at finance, the way I look at investing like that is really fun to me. It allows me to be an artist in my own studio. I actually don't enjoy running the day-to-day of anything. I really just want to be an artist inside the business or brand of whatever I do and that gives me a lot of energy. But the beautiful thing about content is it's intellectual property, right? You put it out there, most of it is. You put it out there and you might not get a lot of hits, like you said, for a long time. But the cool thing is it's still living out there. You're still directing. You're still pointing back to it in different places. And even though maybe for a year or two or five, nothing happens, all of a sudden, boom, it explodes.

And I think about the book, Atomic Habits, James Clear’s book that today most would consider it a household name. But most people don't know that that book kind of laid dormant. It wasn't a huge success when it came out. It didn't sell a ton of copies when it came out. It actually was over a period of time getting into year two, year three, where it really took off. But that's the beauty of having content that lays out there. And maybe it doesn't connect or maybe you don't have the audience yet but in time, maybe that content becomes more relevant or your audience grows or you find other people, other influencers, audiences that connect with it.

Stephanie Postles: Yeah. And I mean for the content piece too, like you said, it's easy to get disheartened by it especially when you start but there are many times where even our content, I mean, we have done maybe thousands of interviews now. I mean, I know I've personally done probably over 800 myself. So, I know within the company, it's probably over a couple of thousand. But even us when we know the model, we know the algorithms, we know how to build the shorts, we know how to pull people on even us, we will put things out there, and it'll fall flat. But then we will post that same thing a couple of months later, and it'll take off. And so, it really is something.

Justin Donald: It’s so crazy. It’s so fickle. It’s so funny.

Stephanie Postles: Yeah, it's fickle. You can't take it personally. You just have to be like, "Oh, let's try it again.” That one didn't work at all that day for whatever reason and, yeah, just trust that if you keep that consistency and you know what your end goal is then you won't get too disheartened. If you're like, "My end goal is not having a billion people look at it because that wouldn't even make sense but it is to find my people.” So, getting those 1,000 true fans like Kevin Kelly like, "Do I have those people? Maybe that's my goal with this content.”

Justin Donald: Yeah, it's great. I mean, I feel like it takes me a lot of, I mean, maybe I should explain it this way. I love podcasting. I love my show. I love interviewing you and other friends and interesting people. Like, to me, this is the greatest gift because I get to be a student and learn. And while other people get to hear what we're talking about, I'm sitting here a student in a classroom of all the things that you're majoring in that you're an expert in. And so, that's really fun for me but I only have one podcast and that at times I feel like is a lot or enough to manage. I can't even begin to think about having 40-plus podcasts. I think you said 42, 41 or 42 over 1,000 episodes at least 800 that you've recorded, and likely with everyone who is doing these shows 1,000s. That really puts you in a league of your own, Stephanie. That's really cool.

Stephanie Postles: Yeah. You have to do something a lot of times to figure it out. Anyone can get good at anything if you just stay there long enough and try it out and can have the long view of like, "Okay. What's the game I'm playing and how can I stay focused on it?”

Justin Donald: Now, I would love to geek out a little bit on your business because I remember hearing your business model. And I know that some stuff are proprietary, and we can't get into the details. And there's probably companies that we can't name but the ones that you can or the strategies that you can, I would love to talk about it. So, whatever you feel comfortable discussing, you have such a fun model, you have such a unique revenue model, and way of monetizing your content, monetizing your podcast, and I'd love for you to be able to share whatever you feel comfortable and willing to share.

Stephanie Postles: Yeah. So, I will first start with the traditional way of monetizing is to grow a very large audience and then allow companies to buy ad spots on it. That's pretty normal and that's the goal. We only have one podcast in our network that does that. So, that's the one podcast that I host that you're going to come on, Mission Daily. That one gets about a million downloads a month or a million to two. It depends on the content and frequency. That's the only one that we have that model because it's the only one that makes sense. And it took many, many years for that show to get there. And I'm very glad we didn't bet on that model because it was such a long-term vision and more of a labor of love of me just being like, "This is just fun and I don't have any sponsor telling me what to do.” And so, let me just be me and I'll talk about whatever I want on there.

Justin Donald: I love it. And by the way, just to interject on that because that is, I mean, anyone I know in the podcast space, that's what they do. They build an audience, they get the companies that want to market, and throw their ads in the middle. And I've been really resistant to that. So, we get companies that ask us all the time, "Hey, can we advertise on your show? We'll give you X dollars for these spots or whatever.” And to this day, we have never done that. Because, yeah, I never started the podcast for that. I'm not trying to monetize the podcast. Now, we have other cool products and we can do our own little commercials of things that we have. But the only way I feel like I could ever do that is if that product is in such utter alignment with my values with the brand and the movement, the Lifestyle Investor’s values, and what we hold near and dear.

Because I see a lot of people and I'll just call a spade a spade, but I feel like they're selling out. They're letting companies that have inferior products or inferior services advertise because they just want the ad revenue. Who knows? Maybe we'll have companies on at some point in time. But if we ever do, they are going to be of the utmost quality and with the best track record, and just companies that are amazing. So, I just want to say that because I feel like most people go down this path of like, "Well, whatever I can do to generate revenue.” And I don't like that model. And I like that you've figured out a hack, though, because the way that you monetize most of your other ones I think is genius.

Stephanie Postles: Yeah. And to stay on yours for a second, I do think when I say that's smart to not do ads, it's because you have so many other opportunities to send your listeners to that stay in your world, stay in your company, stay in your products. That's why you have such bigger opportunities there than if you take a Shopify ad that's paying $25 CPMs. That's $25 per 1,000 listens. So, that's where I'm like most people, if you have your own world, if you're a coach, if you have whatever companies like keep them in your world if you have places to send them to. For the podcast that we do this with, that one, most people listening, I have nowhere to send them yet. Like, they're not going to go and sponsor a big podcast of ours. They don't have that budget. And so, that's why for that show, I'm like, "Okay.” Like, I'm okay allowing others to come buy ad inventory but we have nowhere to send them yet.

Justin Donald: Yeah. Make sense.

Stephanie Postles: Now, so switched over to the other side, the 95% of our company, the way that mission was built was in this way. So, it was in seeing that it's going to take a really long time to build a big audience. Even then, it's unpredictable when it comes to ad spend. And so, the goal was how can we create predictable revenue streams coming in, and a model that is going to give the sponsor an ROI from the start. So, that's how my mind thinks. Half of it is finance, half is creative. So, I'm like I want this sponsor to walk away so happy with what they got. So, our model it's a mixed way of thinking of media strategically. So, we have let's just say one show. It’s called Marketing Trends. We interview chief marketing officers on there. To find the sponsor for that show, it needs to be an enterprise company, who is selling to a chief marketing officer, and they have a high deal like a price point, and it's a complex deal and the deal cycle is long.

So, for all these reasons, the sponsor probably wants to get a hold of our guest. They want content from our guest. They want thought leadership content from that prospect or from their possible customer. And they know that many of these companies would pay a lot of money just to get in the room with their prospect. Many of them would pay $50,000 to get in that room, and to just network with the prospect because they know that person. If they have that deal, and it ends up closing, it could be a multimillion-dollar deal. So, that's the angle of how we do most of our shows is what are the stories we want to tell? Are there aligned sponsors in our network, who also want this great thought leadership content, want to be able to semi-influence the guest flow, where we're going to be putting their prospects on their shows.

We're going to feature some of their favorite customers. They're going to also get to use our content, which is only better for us because then they're getting more awareness around our content here at Mission. And then the ads, it's just the cherry on top like, yes, we're growing an audience. We know how to grow audiences really well and we're going to grow the audiences in a hyper-specific way. So, if you come in and you tell me, I only sell to the Fortune 500 and it's only ever the CMO, that’s who our ad network is going to be attracting to come into our listenership. And so, it's a very different strategic way of thinking about how to have a media channel that is not only keeping us here at Mission happy because we're so happy with the content and the people that we're featuring but it's also keeping our sponsors happy. And most of them are in six-month to one-year contracts. So, they're not just buying one episode a quarter. They're buying one a week for a year.

Justin Donald: Wow. And by the way, I know we can get into this if you want to. We don't have to but I know the price point that the sponsors are paying is high. I mean, you guys are doing well on that front. And I love it because, number one, you guys are making great revenue, you're making it on a per-episode basis, if I remember correctly. And we're talking tens of thousands of dollars per episode, which is cool. And then number two, talk about amazing influence of sponsors, like, "Hey, here are the people that would be like ideal targets. We'd love to get more time with these people. Can you get this person as a guest so that we can learn more about them?” And it's great content for you like you actually would want them as a guest anyway. And I just think that's a brilliant model.

Stephanie Postles: Yeah. And I do see people because I have shared this model here and there with people. And I do see people trying to do it but they mess up in many areas because they either are letting the sponsor control the whole channel or they're building something for the sponsor, which once again, turns into a whole corporate creep show. It turns into inside baseball things. And so, there is a way to do it to make sure that it's like keeping church and state separate, type of thing. Like, you want to make sure that our number one goal is to make great content and to feature amazing people that I look at every time and I'm like, "So proud of you. So proud of you. How have you never spoken before?”

And the sponsor’s happy but that also means pushing back on them sometimes. They don't always get what they want. And if they give me a list of 100 people that they would love to feature, and I think all 100 are not great, then it'll be a no. And so, just making sure that you have that relationship with the sponsors is key.

Justin Donald: Yeah. You have to have the backbone to be able to make those decisions. Otherwise, you become a sellout. And we've all had bands that we've loved that made a pivot or a shift to a different genre of music because that's the genre that's popular in style right now. And it's like, "Hey, what the heck? You guys, you are my favorite band and you were kings or queens in this niche of music. And now you're trying to reinvent yourself and it's not good.” So, you just don't want to be that type of a show. Now, there's another cool story that I thought was interesting and you can share or omit any names that you want but I think this is a really cool strategy because you had a company I think that was maybe pushing the envelope a little bit too much, trying to call the shots, trying to maybe force an angle that wasn't in alignment with where you wanted to go.

And you felt like, "Hey, this partnership isn't working anymore. We've got to end it.” And what does it look like to end it? Do we just walk away and keep going with the show, or do we actually sell this show, this podcast, to the company? So, I'd love to hear your thoughts on that too.

Stephanie Postles: Yeah. So, that was an interesting moment because it was kind of like feels like, I don't give a F moments what happens here. It's a no for me. And so, when you get into that energy, which was the first time we ever had a client, they're a big data analytics company, I ever had a client that I'm like, "This just isn't working.” Like, you want so much oversight. You want so many approvals where normally we don't give approvals to our clients like we run the show. You just be happy with what goes out. But there is no editing after the fact. There is no, “Oh, take out.” They said one of our competitors like, "Take that out,” like there is none of that. Like, we get to run the conversations as we want.

And so, with this one, there was just so much control that was happening and my team members who were working on this show, I had two of them quit. Two people literally left my company and they did not say this, but I definitely was looking at it like, okay, both these people worked on this show and they both are pretty good producers, and both of them not here anymore. And at that point, I had never had anyone quit at our company. We have like very high retention rates with our employees. And so, when I started feeling this pushback from one of these sponsors, it got to the point of a new contract renewal, and it was for a good chunk of money. I mean, it was definitely at that point we needed it. Like, it wasn't something that it was just easy like, “Okay. Like, we're making so much money in other areas, we don't need it.”

But because of the stress I was feeling and I was learning how to hear my yeses and nos and teaching my body of like, what is a yes? What's a no? And with every interaction, it just was like, "No, no, so many nos. This isn't working.” And I basically was like, "We're not going to renew the sponsorship.” But the hard part is we were so intertwined with the sponsor because it was one of the earlier ones that we did a deal with, and so there was a lot of intertwinement.

Justin Donald: All the lessons that you learned because of this sponsor, right?

Stephanie Postles: Because of this, yes. Because of this interaction, it was like they were two intertwined. And I had to get to a place where I'm like, "We're just…” And they were like, "Well, what are you going to do if you don't renew with us?” And I was like, "It's just going to die.” Like, the show just is going to die, has great followership, great everything, but like because of this inner mesh that we are in right now, like isn't going to happen. And I was like, the last thing I put out there was, "Unless you all just want to buy it.” And that was more me being very flippant of like I don't care what happens. Like, if you all want to buy it, then I'm happy to talk to you about that but at this point, there is no like renewal happening. And that's when they were like, "Okay. What's that look like? How can we buy it?” And I was like, "How does one buy a podcast? Let me go figure this out.”

Justin Donald: Yeah. What's the multiple? Yeah. And it's even more so than that I interviewed Nick Bradley earlier, which I don't know how things are going to come out, if he's going to come out before you, you're going to come out before him. Our team is going to resolve that. But we are talking about strategics and strategic acquisitions. And in many cases, they don't need it to be a profitable company. They don't need it to make money because the company itself when they can integrate it, can be far more valuable than any profit that that company has or anything it can even be scaled to. So, this is a brilliant move on your part because they're kind of a captive customer. It's either going to die or they're going to acquire it. You're not renewing.

And by the way, kudos to you for being able to step up and say, "Hey, even though we need this money, we're still going to say no because this just doesn't fit and I've decided I get more headaches working with you than not. So, the money's not worth it.” And that's huge to not be a slave to that money but it's interesting to think about what is the multiple that you would charge? And this isn't a typical deal because it is a strategic that's buying it. They are pot-committed. So, how did you figure that out? How did you resolve making the offer and getting it through and figuring out a price that was fair?

Stephanie Postles: Yeah. I mean, it was a lot of talking to people because I'd never sold something like this before. And the only thing that I ever knew of any way of valuing something, was looking at how the mission got valued when we did our 409A way back in the day. And so, that was my only concept of like how to somewhat value something. And so, I just started talking to a bunch of people of how do you value this? How about this? How do you even sell something? Is this even IP? Like, what if all our processes, we can't transfer them over? So, there were a lot of questions.

Justin Donald: Yeah. Do you keep a piece of it, right? Like, when you sell it, can you keep 20% of it or whatever?

Stephanie Postles: Yeah, we explored that.

Justin Donald: Just to capitalize on the upside.

Stephanie Postles: Yeah. So, we explored many of those things and it got down to essentially putting a multiple on a year's worth of revenue. Because this contract, they were also in these quarterly contracts, even though we always knew it was going to be for longer ones. So, really didn't have so much predictability from like a financial standpoint, even though we knew this is a year-long deal. The contract was these quarterly ones. And so, we put a 2.5 or 3X multiple on a year-long contract of saying, like, we would expect a year-long contract. And so, we're going to 2.5X that.

Justin Donald: And it makes sense because you at least have that baseline of you're putting this much in as a sponsor so we know what's making this. And there are other ways to monetize, but at a bare minimum, you are willing to pay this much. And likely more, right? They're likely willing to pay more. And when it's in-house, then it costs them way less. So, can they at least spend a 3X on that or whatever?

Stephanie Postles: Yeah. And it was helpful knowing their budgets, how much they had access to. I mean, we were very close to many of their team members. And so, it was also like I want to be reasonable. I want to hear what this could be worth to you all. So, I did ask a lot of questions and then also thought about from like a value perspective of, "Okay. Now, you have this show. If you close one client, here's how much you guys are making just from closing it.” So, there was a lot of thought that went into it but then what I realized now is that the easiest solution was the one that I wanted to go with. I didn't want to try and figure a lot of those things out and delay the deal, because I knew there was also changes in their executive leadership that was coming that I was like, “I can't deal with, you know.”

Justin Donald: Lock this up.

Stephanie Postles: Yeah, I need to lock it up and lock it up quickly. And so, it was a very quick thing that happened. And then we ended up consulting with them afterwards to I think we still are to this day because it's hard to run a podcast. That was the summary of what they realized.

Justin Donald: That's not their bread and butter. They got in probably way over their skis and it's great because it created a partial ad, you know, it's probably a discounted amount to what they had paid you before in ad revenue or sponsorship revenue but it still adds to your bottom line. But moreover than that, you sold it for a multiple of revenue and there are very few industries where you can actually sell on a multiple of revenue. Now, outside of the last crazy frothy decade where five of the ten years was just nuts and nothing made sense, and you could sell on all kinds of revenue multiples. Today, we live in a day and age where that's less likely, and there's really only a handful of industries that you can do that. So, well done. Well done.

Stephanie Postles: Yeah. No, it was good. It definitely opened up my eyes to what it feels like to sell a digital property that when you're selling it, there's no expenses really that goes into it. And like, that's the kind of deal I want, 100% margins. Just sell it, basically, be done, and then pass it off. You've got a couple of little transitory things that you need to do, but other than that, like you're done. And so, that opened up my eyes to what was possible when building out these shows and then how to give the sponsors and clients something that they can't get anywhere else. Like, they're desperate and excited to have it, and they can't just rebuild something because it's a huge endeavor.

Justin Donald: I love it. Your background is so perfect for all this too. And I remember before I knew your background, we were talking investing finances. You, A, had really good questions. So, I was like, “Hm, she knows a little more than the average person.” And then, B, you understood the stuff that sometimes when I talk high-level, people's eyes gloss over even when they have some experience in the space. So, I was like, "Okay. She's got some chops. This is good.” And then the more I learn about you, I'm like, "Okay. She's got a finance background. She worked in corporate finance. She has her own company. I'm sure she understands the three basic income your financials, financial statements, and just the ebbs and flows of money.

And so, it's been fun having some high-level conversations with you about investing and growing net worth and doing it in a de-risked way and doing all the things that we do in our mastermind, for those of us that are listening and watching that are part of the Lifestyle Investor community or those that or even part of our free community for anyone that's purchased any of our products. So, yeah, it's fun watching your evolution and kind of where you're going. So, what is next? What do you see for Mission?

Stephanie Postles: Yeah. I mean, right now, so I would say starting earlier this year so 2024, I kind of completely switched how I think about decision-making and get like projects I want to get into. And so, I have a new vision that I've been operating under is around only choosing things that bring me the highest excitement, the highest joy.

Justin Donald: Love that.

Stephanie Postles: I know. So, like learning, which I will say this is a luxury of once you get a company going and it's profitable and it's stable. I never had this luxury before. It was a lot of grinding, a lot of figuring out the future, and trying to make payroll. And so, now that the company has been stable for a while now, that's where I started entering into how do I make sure I'm only choosing things I'm excited by. And I will say that contract decision thing that we were talking about earlier of selling off a show, that also is pretty pivotal to show me, "Oh, I chose myself and what I wanted. How can I do that more?” And so, moving forward...

Justin Donald: And your shows have other values. So, it's like, here's another plan. That's not the plan. But if I had to do it, I would do it and I could still make money. Right?

Stephanie Postles: Exactly. Yeah. So, like this feels good over here. This is stable. And so, now moving forward, we have gotten more into an experimental stage. So, in Q1, we had a goal to launch ten new podcasts in three months, which at that point we had only maybe launched like one or two per quarter. And so, I told my team, I'm like, "We get to get back to our scrappy roots, but we get to expand our content that we're looking into,” because what I care about now is very different than when I started. When I started, it was still a lot of finance stuff, a lot of like crypto. And just, I mean, that world was my world. And now fast forward to today, I'm like, I still love founder stuff, entrepreneurship stuff, but I also like talking about spirituality and parenting and psychedelics and like so many other things.

And so, this new experimentation model is how can we launch different kinds of content and actually grow the show in a way that we have the chance to auction it. And so, we've launched many of these shows. We have our own ad network to even test the concept in, which is also a luxury but, yeah, launching kids' content. We launched this spiritual show called Sacred Echoes. We launched a shipwreck show. And so, that is just more for fun, can we get an audience, and how do we auction something? So, that's the space of where we're headed of like more types of content, content with good intentions behind it. I mean, I have four kids and so that's always on my mind is one my kids don't really even use, like they don't have screens, they don't have iPads. They go to a school where that's a no, but they do listen to podcasts.

And even then I'm like, “I don't know what the intention is behind this. I don't feel like my four-year-olds should be listening to this.” And so, that's where the desire to like put good content out there, know what the intentions are, develop content that teaches kids about grit and resiliency and entrepreneurship and finance. And how can you put in these messages for younger kids to really advance them in a way that I never had? So, different kinds of content, also, a whole new company bubbling right now around psychedelic integration that I'll be partnering on. So, it's just expanding, but still using the model of media in a way that powers companies, powers ideas. Like, media to me is the flywheel of so many of the things that I'm doing and storytelling has been around for so long, so that's what's most effective in my world, and that's the space that I stay in.

Justin Donald: Oh, that's cool. I love hearing how excited you are about it and your passion really shines through. And when you started talking about these niche markets, it reminded me, we've got a friend and member of the Lifestyle Investor mastermind, Kasim Aslam. I don't know if you know him. Brilliant marketing genius. Just awesome guy.

Stephanie Postles: Yeah. Not well but yes.

Justin Donald: Yeah. Sold his company and it was fun because we got a chance to kind of coach him through it while he's talking with all the other people in our community that had sold companies. It was a really neat experience. But one of his specialties is he finds these niche markets, and then he owns those markets. He becomes the authority in that niche market, whether it be Montessori or whatever it is. And it sounds like you're doing that. It's like, "Hey, is this a market? Can we own this market? Let's first of all see if there is a market. Let's test this out. Oh, wow. There's a market. We actually got some good traction. Let's own this market. Let's put out more content than anyone else and let's become the authority of this niche,” right? Is that kind of similar?

Stephanie Postles: That's exactly what we're doing. I mean, a lot of this stuff is so outside of our comfort zone where we're like, we know how to grow these executives shows, these entrepreneurship shows and tech shows, but spiritual content, I mean, that's something I like, but I don't know. Do people want this? And we launched our one show, actually, this one was a month ago and the first episode got 90,000 downloads. So, I'm like, okay, I think people like this. We're going to do more. Another one of ours, it only got, I think, 10,000 downloads. So, we're like, let's launch the second episode, see if people will like it. But if we see the consumption rates aren't there, we see that no one's downloading it, we're not going to do that one. Maybe we wait, or maybe we just kill it all together.

Justin Donald: I love that your low-end shows, I mean, your low-end show and downloads is a top 1% of show. Like, it's incredible. You're like, "Oh, there's only 10,000 downloads,” but 10,000 downloads is top 1% of all podcast downloads.

Stephanie Postles: Yeah. So, I'd say 10,000 downloads I think is amazing for depending on the kind of show. Many of our C-suite shows, when they get 10,000 downloads an episode, we're like, "Great, perfect.” Or on YouTube, if it gets 10,000 views, we're like, "Yes, great.” But for a more consumer-facing show, that I think you do have to have a bigger vision for what you need to get to even be able to show up in the podcast stores, or even be able to get on someone's radar. And, yes, although I will say I know 90,000 downloads for an episode is good. And I love that we can get this kind of data now early, before going all in and betting on building out a whole team around a show.

Justin Donald: That's so cool. Well, I thought about starting a second podcast that was just going to be kind of my ideas kind of like a solo show and I was like, "You know what? I should just incorporate this into what we're doing.” And then every now and again, I mean, there's still the majority of time, I love having guests, but every now and again, we'll just add in like, "Hey, here's a 20 or 30-minute episode with just me sharing my thoughts on, I don't know, banking crisis and how to de-risk from bank standpoint or how to use asset allocation that billionaires use or how to create cash flow that covers lifestyle. You know, and all these different kind of one-off episodes that I can just share all the things that I have fun learning, I have fun teaching, things that we talk about inside the Lifestyle Investor mastermind. So, yeah, I still think it's going to be under the same roof. And I'm giving everyone a preview because I've never talked about this publicly.

Stephanie Postles: Yeah. I’m a yes on this. I already told your team. I'm like, “Justin needs to talk more just by himself.”

Justin Donald: I love it.

Stephanie Postles: That's what I do. I learned that lesson the hard way as well with that Mission Daily podcast. It started as a straight interview show. Just me interviewing everyone, me pulling out all the nuggets. I'm really good at that. And then I realize I'm like, I've just only been spotlighting other people and no one actually knows me. And so, what is the goal of this show? Do I want to be in the background just asking questions all day, or do I actually want people to know me? And so, then it shifted. So, now most of the episodes are either me solo or me and my COO talking. And then every once in a while, we will have a guest but that's not the norm anymore. And it's been a nice shift because then you have more content of things that you actually want to talk about instead of trying to get the guest to talk about things that you're like, “Why do I want to talk about this?” but you don't actually know anything about Web3 so this is awkward.

Justin Donald: That's so good. I love it. Well, you've inspired me to make sure that I do go down this path. And I appreciate you working with my team, and I'm excited to see how we can collaborate. I think there's tons of opportunities and potential there. So, yeah, it's been great having you on the show. Where can our audience find more out about you, Stephanie?

Stephanie Postles: Yeah. I mean, the fun places to find out about me would be on social media like Instagram. I know my team is growing that account and I'm on there too. TikTok, so just searching for Stephanie Postles and you'll find me. But if you want to find out more about our company, just go to Mission.org and you can check out some of our shows or find me on LinkedIn. I'm kind of everywhere. So, yeah, I'm here to chat with whoever wants to.

Justin Donald: I love it. Well, this has been a great episode, I appreciate it. I love ending every episode that we do with a question for our audience. So, it's a simple question. What's one step you can take today to move towards financial freedom and move towards a life that you truly desire, one that's on your terms, not by default like most people, but by design? So, think of something you can take from Stephanie here today and put it into action immediately in your life. Thanks so much for tuning in and we'll see you next week.

Stephanie Postles: Thanks.

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Justin Donald is a leading financial strategist who helps you find your way through the complexities of financial planning. A pioneer in structuring deals and disciplined investment systems, he now consults and advises entrepreneurs and executives on lifestyle investing.

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