Heather Osgood: Founder of True Native Media

Episode 287

If you are curious about learning more about podcast advertising, or you want to determine whether your brand should be looking to monetize through podcast advertising, this episode is for you! Heather Osgood, Founder of True Native Media, is a serial entrepreneur who knows her stuff! Her incredible journey as a seasoned entrepreneur is riddled with learnings. Plus she shares best practices including what it takes to build, scale and lead an agency. You won’t want to miss this inspiring discussion straight from someone who has been in the trenches! On this episode of #TheKaraGoldinShow.

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Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be I want to be, you just want to make sure you will get knocked down. But just make sure you don’t get knocked down knocked out. So your only choice should be go focus on what you can control control control. Hi, everyone and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi, everyone, it’s Kara Goldin from the Kara Goldin show. And I’m so so excited to have my next guest on here, Heather Osgood, who is the founder and CEO of true native media. And I’m really thrilled to have her not only because I’m inspired by her journey, this is just another great, great story of a founder who has done a few different things in their life, and has created an incredible platform for podcast advertising. So if you’re ever thinking about, Gosh, should I be advertising my brand on some of these great podcasts, including the Kara Goldin show, but also other podcasts as well, or if you’re a podcaster, and you’re just trying to figure it all out? Heather is here today. And I’m sure she’s gonna give us some tips. And in addition to hearing more about her journey, so really, really thrilled to jump into that. Also, she is the host of her own podcast called the podcast advertising playbook. So if you haven’t listened to that, too, it’s super, super great. I’m just really thrilled to have you. So welcome, Heather,

Heather Osgood 1:51
thank you so much for having me. I’m excited to be here and chat with you today.

Kara Goldin 1:56
Absolutely. So let’s start at the beginning, I would love to get a little bit of a glimpse into who was Heather, as a child, what did she think she was going to be doing when she grew up? And is it anywhere close to what you had images of Heather as a grown up doing?

Heather Osgood 2:16
No, not at all. Actually, I feel like a super, super ambitious person. And my, one of my core values I would say in life is just ambition. But when I was a kid, I really my mom was a stay at home mom. And the only thing that I really kind of had a model for was being that And so growing up, I just presumed I was gonna get married. I wanted to live on 100 acres and have oodles of children and you know, live off the land and things like that. And that is far from what I’m doing today. So it’s kind of ironic, I always hear these founders were like, oh, yeah, I was, I was selling things, you know, in junior high. And I started my first business at 10. And I’m like, Yeah, that was, that was not my kind of my path. But I’m glad to be an entrepreneur today for sure. Where did you grow up? So I actually grew up in San Luis Obispo County Area in California. Oh, yeah. And I had lived there my whole life and about a year and a half ago moved to Florida. So it’s been California is great. And San Luis Obispo is great. But Florida has also been a wonderful experience. Was there

Kara Goldin 3:25
anybody who really inspired you? I mean, how did you start to get into business?

Heather Osgood 3:31
Yeah, for sure. So when I was in my early 20s, I had a child fairly young, and I started selling radio advertising. And I would say, I had some extraordinary mentors, when I was selling radio advertising that gave me a ton of confidence. And really, I would say, kind of trained me what it was like to be a professional. And then, you know, just kind of looking around at the different business owners at the time I sold radio advertising, so I was constantly dealing with different businesses. I was, you know, just really struck by this idea that being a business owner wasn’t maybe as hard as I thought it would be. And I would say that the people around me the the leaders that I had, and that you know, that early kind of days selling radio really helped push me along in my career.

Kara Goldin 4:21
So how did you make the transition from radio advertising to podcast and actually starting your own agency?

Heather Osgood 4:30
Yeah, well, so having dealt with so many small business owners, I think, after several years, you know, and I think it’s kind of almost like when you’re a child, you think that adults understand everything, right? You’re like, oh, as soon as I’m an adult, I’ll get the world and then you become an adult and you’re like, oh, wait, all of the adults were just kind of pretending to understand everything. And I felt like it was very similar with business owners. You know, when I first started dealing with business owners, I thought, oh my gosh, They must understand the way money works, they must understand, you know how to run a business. But after I did that for several years, I realized that business owners were just like every other person, they were just doing the best that they could, they were just trying to figure it out. And it struck me one day that I could be a business owner, I was like, I know just as much as these people do. And I actually could probably do a better job than most of these business owners were doing. And so I started by founding a trade show production company, with one of my best friend’s and her and I ran it for almost 10 years together. And it was really a wonderful experience. And I learned so much about what it was actually really like to run a business. And then I sold that company to her. And for the first time in my adult life, I didn’t have like that frenzy. eveness, right, of always having to work. And so I started listening to podcasts. And then I was like, where are all the ads, like, these shows are amazing, they should have ads in them. And I did some research. And I found that really, if you weren’t in the top 1% of podcasts, there weren’t any companies out there to try and help you get ads. And I was like, I’ve sold radio ads, I’ve sold newspaper ads, magazine ads, I know I can sell podcast ads. And so I founded the company really to help independent podcasters. And it turns out that my timing was really good. I founded it in 2016. And that was kind of, you know, when podcasts really started to take hold. So it’s been a really interesting journey so far.

Kara Goldin 6:43
For people who are not that familiar with podcasts that are, you know, maybe just starting to listen to my podcast and getting kind of the hang of things. What would you say is like the big difference between radio and podcasts,

Heather Osgood 6:58
I think the most important part of podcast is that the listening is so intentional. So if you’re thinking about terrestrial radio, you know, most people have listened to terrestrial radio. And of course, you pick your favorite radio station, but there’s kind of a level of disconnect. Maybe you have that favorite morning show that you listen to. But a lot of times radio listening is very passive, right? Like, maybe you turn it on in your car, maybe you turn it on as background noise while you’re doing work at home. Or maybe you hear it like at an office or something like that. But podcasting is extremely intentional. You know, people don’t just accidentally start listening to a podcast, they come because they want to be there. They liked the host, they liked the content. And so there’s just this intentionality around listening to a podcast that is so different than terrestrial radio. And I think one of the things that really appealed to me about podcast advertising in particular, was that the host would do the reads. And, you know, when we think about advertising, the way I always think of it is, we all want to buy products and services, right? We’re living in America, we’re a consumerist society. But we want to buy products and services that we feel will edify our lives in some way. And we don’t like those kinds of screaming ads, right? There’s a reason that you can, you know, when DVRs came out, there was a reason for that. And there’s, you know, a reason why we have ad blockers. And it’s because a lot of times people don’t bike ads, right. But if you know, like and trust the host, and the host is like, Man, this product is pretty cool. And believe it or not, I am shocked at the number of hosts who turned down advertisers all the time. But you know, you’ve got this host that is actually genuinely recommending a product or a service. And that is going to be more powerful for the advertiser. But it’s also more interesting for the listener, right? Because they’re not, it’s not like that monster truck kind of ad coming at you. It’s, oh, gosh, that’s an interesting product, I should maybe check that out. So your conversion rates are higher for advertisers. It’s a better listening experience. And really, when people are surveyed, most podcast listeners say that they actually really don’t even mind podcast ads. So those are really I feel like the big differences between podcasts and radio and really why podcasts are so special.

Kara Goldin 9:32
Absolutely. Well, that is such a good description of it. And I think that that is so true. I mean, when I think about when I’m listening to podcasts to and when you have somebody that you enjoy listening to, and they’re reading about a brand and you know, you feel like you’re just discovering it for the first time. I think it’s, you know, for me as a podcaster. I feel like the brands are really part of my content. And I take it very, very seriously which is very different I way long ago, I used to I worked at CNN in the very early days, Ted Turner was still running around the office. And and it’s, you know, we did not think about ads in the same way, as I think about ads that are running on my show today. So I think it’s, it’s, it really is finding the right brands that can kind of represent your product, if you are a brand that are looking that’s looking to advertise it that gets really, really key. So I love that description. So jumping around a little bit, but you’ve founded a few different companies. And you touched on this slightly, but I would love to hear kind of, you know, some of the companies that you’ve a couple of the companies that that you’ve actually, prior to founding true native and 2016. What else did you create?

Heather Osgood 10:59
Yeah, for sure. Well, so the first really substantial company for me was simply clear marketing, which was the tradeshow production company that I mentioned before. And what we did was we put on Home and Garden expos, and health and fitness expos, which really went along well with my advertising kind of journey, because it was just selling booth spaces to businesses so that they could reach people in person instead of through other other mediums. And that was really a terrific experience. It was wonderful to have a business partner and my best friend, I’ve looked back, and I think I feel like I got so lucky because it could have gotten so bad. And it didn’t, it really went super, super well, I would say the biggest lesson I learned in that business was the idea of starting with the end in mind, I literally, I would say probably two or three years into that business, I was like, I am never going to ever want to do anything other than this. Like this is the best business and the best thing in the world. And I loved it. I loved every minute of it. But then, of course as things in life do, things changed. And I came to a point where I wasn’t in love with the business anymore. And I wanted to make an exit, but we didn’t have a plan for that. And so it was really challenging. Because in a lot of ways, it was like going through a divorce, which, you know, it’s just super painful when you’ve worked with somebody, you know, shoulder to shoulder and you’re best friends. And we had babies at the same time. And we just did everything together then to be like, Oh, well, you know, no more I’m going to leave it was really a challenge. But, but a great, great business. And then my husband and I started a hair cutting business that we originally thought we wanted to franchise, very similar to kind of Sports Clips. So we owned that for, I think about eight years and sold that. But that was a very different learning experience as well. But all in all, you know, I think I’ve learned a lot as a business owner along the way.

Kara Goldin 13:00
That’s amazing. So you start your company, the true native media, what did you do differently thinking back on, on those that you were like, I’m never going to or this time we need to

Heather Osgood 13:15
the biggest lesson that I learned in all of it was that I didn’t want to have partners. So the first business I had with my best friend was wonderful, like I said, but there were challenges and then the haircutting business I did with my husband, and there were challenges there. And I realized that I had learned so much, but I was very clear on how I wanted to run a business. And when you have business partners, I think two things happen. Number one, there’s always compromise, right? You always have to look to somebody else and say is it okay? If we do this. So I have this vision, this is my goal, this is what I want to accomplish, but then you have to have someone else’s buy into. And even if you’re super well aligned, you’re never perfectly aligned. The other thing I found was that I wasn’t able to step up as a leader in the capacity that I wanted to step up and lead. I have always been the stronger personality in those businesses. And I have always wanted to be in that leadership role as the buck stops here. So it’s my vision, it’s my creation, my determination. And there are so many benefits to having partners, but I didn’t feel like I could really kind of be the best of myself working with with other people like that. And so going into true native media, it was super important to me that I be the sole owner of the company and my husband is bothered by it frequently that he really doesn’t have a role in the company but It’s something that was really important to me that this be my sole entity, you’re really

Kara Goldin 15:06
representing two sides, you’re representing a lot of podcasts, including the Kara Goldin show. But you’re also representing are really trying to help brands find the right mix for them. So are there any particular trends that you see on either side of the fence that you think are really, really important? You started obviously, in the early days of podcast advertising in 2016. But like, do you see a curve happening? And in, you know, in any direction right now?

Heather Osgood 15:40
Yeah, that’s such a great question. And man, we have seen so many changes in the industry. I mean, the thing that’s so great about podcasts is that independent nature that we talked about earlier, and how important it is that every podcast kind of has its own identity, that that leads to a lot of fragmentation in the market. And so from a, an advertising perspective, it can be really challenging for companies to come in and see a really straight path to, you know, enter the podcast ad space. And like we had talked about those hosts read ads, and how valuable they are. But they’re also super labor intensive. And when you think about big companies and big brands that are using it used to going to trade desks and saying, hey, I want to buy this many impressions on this type of content, like, enter, here we go done. You know, we’re literally talking like minutes that something like that could take versus hours that it would take to set up a podcast campaign. So you know, for me, it’s always been really important that we lean on the influencer marketing side of things when it comes to host read ads, because I’m care people are listening to you, because they know like and trust you and they’re interested in your journey. They’re interested in the guests that you have on, and you are going to influence your audience to purchase products in a different way than hearing that pre recorded ad. But it is really challenging to execute a campaign. So there is fragmentation, that the biggest developments that I have seen in the podcast space that I know are going to continue to grow are really just development around ad tech, and how we can actually reach the audience that’s listening. One of the really kind of important and almost tragic parts of podcasts in general, are that we don’t do a very good job of monetizing all of the impressions that happen. And what I mean by that, is that when you’re doing these hosts read as they can be delivered in a way where that ad is just unique to this particular episode, right. And that’s great. But that means that when people are listening to the back catalogue, or listening to episodes, you know, today that were maybe produced a year ago or two years ago, they might not always get an ad delivered to them. And that’s not to say that every single, you know, podcast has to be monetized. But I mean, I was listening to Brene Brown’s original podcast, I think called dare to lead. She was interviewing Jim Collins from good to great. And I have been kind of tapping into that recently. And that I, you know, it was a two hour interview. And throughout the entire podcast, she had ads that were sprinkled in, and they were programmatically inserted, they weren’t heard they were pre recorded ads. And I do think that there is a place for that. So as the industry grows, you know, my prediction certainly is that we’re going to see more of that pre recorded announcer red ad being inserted. And I think that if we as an industry want to continue to grow, we really do have to make sure that we’re monetizing all of those impressions, because when you put the podcast industry up against other advertising vehicles, podcasting is still super small. We exceeded a billion in ad sales last year as an industry, which was an amazing benchmark for us. But when you put that side by side with the billions and hundreds of billions of dollars, that other types of advertising vehicles are doing, it really still is a drop in the bucket. So as we look at the evolution of the industry, I think that piece of monetizing all impressions is really important.

Kara Goldin 19:35
Yeah, I totally agree. People always think that successful people, owners of businesses, CEOs, founders, they just snap their fingers, they’re lucky they figure it out, right. And it’s more than anything. What I’ve found in talking to so many is that there are challenges along the way. Maybe they ran out of money and they had to shut down a business or something did not go the way that they thought maybe the pandemic hit right when they were starting. I mean, lots of things can happen along the way. I’d love to hear you’ve had so much success, I would love to hear if you hit a challenge, whether it’s in your existing business or another business that you were starting along the way that you could share just where things are not. Or I guess to quote, Brene Brown being vulnerable and sort of saying it’s not all, you know, Rosy, pretty, you know, sometimes you have you have learnings that you didn’t like, but you have to deal with them.

Heather Osgood 20:44
Yeah, yeah, for sure. No, I think that we definitely all have failures and struggles in business. And I certainly have had my fair share of them as well, I think a really impactful experience for me has been that, as I mentioned, ad tech is really an important piece of the industry. And I had really just been observing all of the things that we were doing in the podcast space and saying, Why isn’t there software for this? Right, there should be software for this. But as I mentioned, you know, my background really has been, I would say, almost entirely service based. So all the businesses that that I have been involved in, have been service based, and I am certainly no IT experts. I’m not a software developer. But I really felt like the industry needed something that I could deliver. And so I spent quite a bit of time trying to figure out how to develop software. And it was very far outside of my comfort zone. And I was like, That’s good, right? Like, I want to be outside my comfort zone. And I’m gonna work on doing this. And I know I can, but because I really wasn’t able to actually build the software myself, I needed to find someone who could build it for me. So I spent, like I said, quite a bit of time coming up with a plan, I spent a lot of time searching for a CTO. And then I finally found someone within the industry who I felt like really understood what what we were doing. And we started, you know, we started the project together, and I was really convinced that I could make it work. One of the interesting bits about the podcast industry is that it is really very male focused, it has been a very male, you know, heavy industry, when you look back, traditionally, like when I got into podcasting, there were way more male, there still are way more male hosts than there are female hosts or like, there was a recent study where 70 I think it’s 72% of all podcast hosts are men. But the listenership even was mostly men. But then when you talk about anything at an industry level, you know, any of the bigger companies, they’re almost all dominated by men. And so the CTO, you know, he and I were working on the project. And then he said, Oh, you know, what, I decided that I don’t have the bandwidth to do this anymore. And then went on to kind of take my idea, and is now creating something that’s pretty similar to that. And, you know, I’m sure that there are, you know, I’m sure that there are probably, you know, paperwork and contracts that we signed, and I could probably go after him and talk, you know, talk to him about it. But it’s like, for me, I just had to let go. I think the hardest part of that journey was talking to people in the industry about what I wanted to create, and then having so many of them say you can’t do that, like, oh, you can’t do that. You don’t have the ability to do it. I was talking to when when founder in this space one day, a male founder and he said, What makes you think you can do this? Like, is your husband and it or something and I chest about Loftus? Are you kidding me? So that still has been, you know, that still is kind of a rough patch for me, just trying to think that, you know, it’s not all as as rosy out there maybe as we think it is. And ultimately, I decided like to abandon the project, I felt that I had invested so much time and energy into it. And it really wasn’t where my energy was best spent, and subsequently actually have launched another business. Well, it’s going to be launching next week and I’m excited about that. But anyway, that was just a really interesting experience to kind of walk through.

Kara Goldin 24:57
Can you talk about your business that uh, Guess what, by the time this airs, it will have launched?

Heather Osgood 25:03
Yeah, yeah, I’m super excited about it. And I have a couple of wonderful co founders in that business, but it’s called the podcast broker. So, you know, obviously, we sell websites, we sell all kinds of digital things. But for some reason, we haven’t sold podcasts. And, you know, having worked in this space with so many podcasters, over the years, I have had conversations with hosts who are like, Heather had been talking about weddings for seven years, like I am done, I don’t want to talk about this anymore. I’m just gonna stop the show. And like, no, don’t do that, you know, you’ve created this wonderful asset, and you should sell it. But, you know, of course, large companies that have been content creators like wondery, or gimlet, I mean, they’ve been acquired for millions of dollars, but the average independent podcaster doesn’t have a good platform to go and sell their podcast. And, as you know, Kara, working on creating a show isn’t an easy venture. And when you finally do establish an audience, it is, you know, at some point, most everyone is gonna get to a point with their show where they’re like, you know, I don’t know if I really want to continue this anymore. And so the basis of the podcast broker is really to say, hey, you’ve created, you know, this asset, let us help you sell it. And then, you know, on the flip side, for those who are thinking about getting into the podcast space, instead of starting from ground zero, you know, if you are maybe wanting to start a health podcast, why not purchase an established health podcast and take that on, and you know, do a graceful transition from host to host, but then you’re walking into an established audience, instead of starting from ground zero. So I’m really just excited to be able to help podcasters they put so much energy into the product. And I think one of the things I’ve learned that is so hard is that most content creators are not business people, and they don’t approach their show like a business. And it’s unfortunate, because I think a lot of times, they miss out on opportunities to really monetize what they’ve created.

Kara Goldin 27:08
So interesting. And obviously, you’ve been in the space for a while, and you know it and, and you’ve watched so many acquisitions, and, and, you know, know, many of the people that have been involved in that. So I’m excited to see exactly where that goes. That’s super, super cool. So if you look back on your younger self, and think about, okay, I was so stressed out about this, I thought it was all over with, what do I do next? What would you tell yourself?

Heather Osgood 27:41
You know, I think that surrender is one of the most important pieces to life, I really believe that we all have a journey and a path that we’re on, and my job every day is to show up as well equipped to be the best version of myself that I can be in that day. And I have been, you know, my younger self was so controlling, and, you know, so I also think so timid. And I really wasn’t willing maybe to engage in conflict, or I wasn’t, I wasn’t taking the risks that I know now really helped to pay off. So, you know, just understanding that surrendering to the process and having the confidence to really live like who you are, does ultimately produce the kind of life that is the journey that that you want, and tapping into that is just so powerful.

Kara Goldin 28:47
hearing your story, and I have four kids, I have three in college and and one a senior in high school, I always laugh because I know when I was their age, I was always thinking that I’ve got to go major in something and then go and do this thing and and every successful person I’ve talked to has had a lot different roles and multiple roles are where they start out doing one thing and then they’re doing another thing maybe in your case, the technology wasn’t there like podcasting wasn’t there when you were first getting started, but then it was and so it’s like the future you know, kind of takes care of you I believe and and it’s more than anything, it’s staying busy, always learning, always staying curious. Things like that. I think are such great lessons just from listening to you about your journey. So I’d love love that you came on to share a lot more of that with us. So excited to see this next business that you’re launching. I love that you have multiple businesses going at once to you would have never been able to really talk about that 10 years ago, right? That was like you had one. And this was what you were doing. So lots of lessons there. So it was such a pleasure to speak with you, Heather, and thank you so much for the super great insights and all the good stuff that you’re doing. And we’ll have all the rest of the information for true native media in the show notes so that people can reach out to you all if they’re thinking about trying to figure out how to get their brand exposure on different podcasts. And like I said, really appreciate you coming on. And thank you, and have a great rest of the week. Thanks, Heather. Thank you. Thanks all for listening to this episode. We hope you enjoyed it. And I want to thank all of our guests and our sponsors. And finally, our listeners, keep the great comments coming in. And one final plug if you have not read or listened to my book undaunted, please do so you will hear all about my journey, including founding, scaling and building the company that I founded. Hint we are here every Monday, Wednesday and Friday. Thanks everyone for listening, and goodbye for now. Before we sign off, I want to talk to you about fear. People like to talk about fearless leaders. But achieving big goals isn’t about fearlessness. Successful leaders recognize their fears and decide to deal with them head on in order to move forward. This is where my new book undaunted comes in. This book is designed for anyone who wants to succeed in the face of fear, overcome doubts and live a little undaunted. Order your copy today at undaunted, the book.com and learn how to look your doubts and doubters in the eye and achieve your dreams. For a limited time. You’ll also receive a free case of hint water. Do you have a question for me or want to nominate an innovator to spotlight send me a tweet at Kara Goldin and let me know. And if you liked what you heard, please leave me a review on Apple podcasts. You can also follow along with me on Facebook, Instagram, Twitter and LinkedIn at Kara Goldin. Thanks for listening