Startup Secrets of Five Female Entrepreneurs

Startup marketing agency Bigeye’s podcast features five female entrepreneurs with flourishing businesses sharing their founding stories and business models.

IN CLEAR FOCUS: Female entrepreneurship in the US has increased by over 30 percent since 2007. In this episode, five female entrepreneurs leading flourishing businesses share their founding stories. We hear from a direct-to-consumer pioneer who created the top-ranked cat subscription box, a beauty industry professional creating a CBD line, an Influencer-turned-CEO, a journalist who found a new creative outlet in podcasting, and an advertising matchmaker connecting podcast producers to sponsors.

Episode Transcript

Adrian Tennant: You’re listening to IN CLEAR FOCUS, fresh perspectives on the business of advertising, produced weekly by Bigeye. Hello. I’m your host, Adrian Tennant, VP of insights at Bigeye. An audience-focused, creative-driven, full-service advertising agency, we’re based in Orlando, Florida, but serve clients across the United States and beyond. Thank you for joining us for the last episode of this season and of this year. During the course of 2020, issues around diversity, equity, and inclusion have been front of mind. In November, a century after women first gained the right to vote, America chose Kamala Harris to be the first ever female to hold the office of Vice President. The organization SeeHer, led by the Association of National Advertisers, seeks to improve the accuracy of portrayals of women and girls in US advertising and media. Women have long been underrepresented in the media’s depiction of entrepreneurship – yet the number of female entrepreneurs in the US has increased since 2007 by over 30 percent. And their firms have grown at a rate one-and-a-half times greater than other small businesses. Female business leaders also tend to begin their entrepreneurial journeys earlier in life than their male counterparts. According to a survey, 51% of female business owners were under the age of 50 when they launched, compared to 44% of men. The National Association of Women Business Owners reports that there are 9.1 million women owned businesses nationwide, employing 7.9 million employees and generating $1.4 trillion in sales. So in this episode of IN CLEAR FOCUS, we’re going to revisit conversations with five female entrepreneurs who were our guests this year, and learn how each of them arrived at the ideas for their own businesses. In June, we spoke to Kristen Wiley, founder and CEO of the influencer marketing agency Statusphere.


Adrian Tennant: When did you first realize that you wanted to pursue a career in marketing? 

Kristen Wiley: It’s kind of funny, although it’s probably not what most children want to grow up to be when they’re little. I actually always wanted to be in marketing. I thought advertisements were actually super cool on TV. I would watch TV just for the ads and I would even make ads myself. So I knew I always wanted to go into marketing, but of course, when I was little social media wasn’t even a thing, so that evolved over time. But I knew from when I went into college that I wanted to go into advertising and marketing. 

Adrian Tennant: So in 2016, you founded Statusphere with a mission of matching consumer brands with influencers. What’s your definition of an influencer? 

Kristen Wiley: Yeah. My definition of an influencer is anyone who influences a buying decision. I actually quite often talk about how specifically influencer marketing, everyone views it as online, but it’s really just word of mouth marketing in the new age. Social networks have allowed real people to build audiences and actually influence outside their sphere of just who they can talk to. So it’s been very interesting to see how platforms like Instagram, Facebook, and TikTok allow you to go outside of just your little sphere of influence – where it used to be big movie stars that could do that before social media was a thing. 

Adrian Tennant: So Kristen, what insights sparked the idea that ultimately became Statusphere?.

Kristen Wiley: So actually, when I was in college, I had a professor who told me the best thing that I could do to actually learn about marketing in general was to start a blog. He said, “You’d learn way more than anything you’ll learn in my classes.” What he said. His name was Jim Hobart. He’s actually pretty popular in the Orlando community. He’s a photographer, but he was an adjunct professor at the time. He told our whole class that, and that night I went home and I started a blog and he was so right. I always say that’s the best career advice I’ve ever gotten. I started this blog, had no idea what I was doing. I had to learn how to build a website. I had to learn SEO. I had to learn, you know, photography, really content. If you look at my first blogs, they were just horrific. But, um, but I did learn so much. And that was actually what even spurred me to get my agency jobs, all of my jobs, where they saw my blog and they were like, “We don’t even care about your GPA. You did that? We’re hiring you.” Um, so I always give him major thank you for that, that piece of advice. Um, so I did have that experience. And then when I started working at different agencies, I always got thrown into doing influencer marketing because I was the only one that had experience with it. So they were like, “Oh, you’re young, but no one else on our team has really influencer marketing experience” – this is 2011, 2012 – “but our brands are asking for it. So can you help us?” So I was in this unique position where I was given a budget, I got to test out other influencer marketing platforms. I was on them as an influencer and as a brand. And that’s where I started seeing all these holes where I was like,” there just has to be a better way.” On the influencer side, I was a food blogger and I would get pitched mattress companies and really strange things that had nothing to do with my blog. And I was like, “This is a waste of my time and why is it this way?” And then on the brand side, I was sifting through hundreds, if not thousands of influencers trying to find the right one. And I was like, “there just has to be a better way where we can match the two.” And that’s where the idea was born. 

Adrian Tennant: Now, prior to founding Statusphere, had you any interest or experience in entrepreneurship?

Kristen Wiley: I had interest in entrepreneurship, but I didn’t think that I would become an entrepreneur. Looking back when I was younger, I was one of those people who did always have a side hustle where I sold like really random things door to door. I’ve sold everything from like bows to like purses. I used to like buy stuff from Marshall’s and resell them on eBay. So I used to always do those type of like weird entrepreneurial things to make extra money, but I never thought I was going to start a company. So that being said, I started working at one of the agencies locally  and one of their verticals was startups. So I worked in sales in that, and I started interacting with lots of startup founders. And that’s when I started, I think, realizing in the back of my head, like “This is something I think I could do.” Like I started meeting other female founders and seeing them do it. And I was like, well, you know, “I’ve had this idea for a while. Maybe I should try it.” 

Adrian Tennant: So from idea to establishing Statusphere, what did that look like? 

Kristen Wiley: So I had the idea for Statusphere for a while before starting it. I bought the URL actually like two years, probably, or year and a half before ever launching anything.  I think that’s a story that a lot of entrepreneurs talk about because it just takes so much effort to actually make the jump because, you know, you’re so nervous, like, “Is this what I should be doing? I have a great job.” I actually loved my current job at the agency. So it made it even harder. Like “Why would I do this?” But the way that it looked was I actually had told my boss at the agency about it  and he was very supportive, which I think is also unheard of. And I thank him a lot for being so supportive. Because that was a big thing that pushed me. Like “He thinks it’s a good idea. Maybe I should try this.” And I did on the side. And the way I started was I reached out to a bunch of  influencers with a simple landing page that was like the first subscription box for influencers. It was a really ugly landing page with a form on it, where you could apply. Um, and I just messaged it to 10 influencers that I personally followed that didn’t know me personally. And I woke up the next day and had 12 applications. I was like, “Well, maybe this is something, this is a good idea!” 


Adrian Tennant: Kristen leveraged her agency-side knowledge of social media and her experiences as an Influencer to identify a gap in the market and then create a solution to satisfy a previously unmet need. If you’d like to hear the full interview with Kristen Wiley, you’ll find it on our website with the publication date of June 18th. Over the past 15 years, Holly Kapherr has made a name for herself in the world of culinary public relations, building on a career that has included cookbook and magazine editing, recipe testing, and food styling. But in 2019, after a personal health crisis had forced her to reevaluate Holly launched The Culinati Podcast with the stated mission of exploring big ideas in the galaxy of gastronomy. We caught up with Holly in October.  


Adrian Tennant: So what inspired you to launch The Culinati Podcast?

Holly Kapherr: Well, it was kind of a roundabout way. I’ve always had NPR dreams. I’ve always loved listening to public radio and particularly the interview shows like Fresh Air. And I often thought about what it would be like to have my own radio show. And as a journalist, I spent a lot of time interviewing people. And truly that was the best part of being a journalist was being able to get in touch with people, learn about them and learn about the things that they are passionate about and the cool things that they’re doing. And it came to me that most of that stuff that we were talking about, wasn’t going to make it into the articles that I was writing because that wasn’t the subject of the article. So a lot of those amazing interviews and stories were just lost. So they weren’t the things that were being covered. And so I was like “there has to be a place for those things, because those are the real interesting stories.” So, um, I had this idea for a little while. And a friend of mine had a beer podcast. It was a female-focused beer podcast called Pretty Little Pints. And she invited me on the podcast and it was my very first time doing it. And we were going to talk about Beaujolais Nouveau. It was Thanksgiving time. And she wanted to do a wine podcast and wanted to taste the new Georges Duboeuf Beaujolais Nouveau. And she’s “Let’s talk about it. And let’s do it on the air.” And I said, “Okay.” So I went on it and I had a great time. And after the show was over, she was like, “My husband and I bought this domain. And we’ve never done anything with it, but if you would be interested in doing a podcast called The Culinati, we would love for you to record at our studio.” They have a really cool studio that’s located in their house. They’ve turned a bedroom that they don’t use into a full-on podcast studio. And so people can come in and just record their shows. Instantly I was interested. And then a couple of months later, I was diagnosed with breast cancer. Everything that I had been working on, as far as creative sort of got pushed to the side, I had to just focus on my full-time job and getting better of course, going into treatment. So my entire world was going to doctors and getting treatment and trying to maintain my full-time job and that kind of thing. So I had to push everything to the side. So as soon as I was done with active treatment in December of 2018, I said to myself, “Okay, I’m going to pick this up. This is something that I really want to do. I need a creative outlet. I want to do something completely different.” And so I went full speed ahead. I started. I had the logo in my head already. And so I got in touch with a friend of mine – Tim Eggert, the graphic designer behind the city of Orlando flag. And so as soon as I got the logo, it felt real. And so I learned everything I could, I read everything I could, I listened to other podcasts on how to do podcasts and thought about the people that I wanted to emulate in my shows. My previous life was in magazines and so I did the same thing that you do in magazines, which is you put together a front of book, you put together a feature well, and then you put together a back of book. And so the intro and all the stuff that we do at the beginning, it was like the front of book. And then I was like, “Okay, now I have to have features.” And so I would say, “Okay, who are like the big people in town that I definitely want to have as my first three guests?” And I chose people who were like very inspiring to me and people who were really interesting and did things in the food world that I thought people would love to hear about and would be a great hook for my first three episodes. And then I put together a back of book, which is a little bit more like a wrap-up and then also we do a really cool section called Short Order. And it’s just quick association questions that I ask my guests that are really lighthearted and food-focused, just so that our audiences can get to know the guests a little bit – a little bit more on it on a different level. So that’s what inspired me. I’ve always loved the radio and always love that medium. I feel like it’s a really intimate medium, being in someone’s ears, going into their brain, getting them to think about something else. And I feel like there’s something really magical about a really good interview. So that was the main inspiration.

Adrian Tennant: Holly, do you monetize your podcast? Do you run paid advertising, special sponsorships or partnerships with any of the businesses that you highlight?

Holly Kapherr: I don’t have any more monetization in my show yet. The reality is that I am doing this show to glorify, to showcase, to feature the people who are doing amazing things. And I have not looked to make any money off of this. The money that I hope that is changed hands is for the businesses that I work with. I hope that the 300 people or whomever that listen to each episode, that they go to the restaurant or go to the website that we’re talking about, they spend their money there and it helps my guests do other cool things or continue doing the cool things that they’ve been doing. The money goes to my guests. That’s the intention. 


Adrian Tennant: As you heard, Holly found a new creative outlet for her love of interviewing people. And one that helps the restaurateurs she works with attract and connect with new guests. If you’d like to hear more of the interview with Holly Kapherr you’ll find it on the IN CLEAR FOCUS page with a publication date of April 24th. Now, if Holly does decide to monetize The Culinati Podcast, our next guest will be a great resource. Heather Osgood had been selling advertising for over 20 years on radio, print, and trade show booths, but was so passionate about podcasts that in 2016, she founded True Native Media, a firm dedicated to connecting podcasts with advertisers. Heather was our guest in November.


Adrian Tennant:  What was the insight that led you to found True Native Media?

Heather Osgood: I founded True Native Media because I became a bit of a podcast-obsessed listener. I sold a trade show production company that I had before for about 10 years and for the first time in my adult life, I had so much time to spend listening to podcasts. And the more I listened to podcasts, the more I consumed all of this audio, I was shocked to find that there were so few ad messages in podcasts. And when we look around the landscape of all of the media out there, what we find over and over again are ad messages. And so it seems strange to me that podcasts, almost like this island and while some of the very biggest shows had advertisers, most of the shows that I listened to, which I would classify as mid-level shows did not have advertisers. So I took a look at the industry and I found that, yes, those 1% of top shows were being served by firms that were happy to connect them with advertisers. But then there were all of these essentially hundreds of thousands of impressions that were going unserved without ad messages. And I just felt like there really was a hole in the market and I wanted to help fill that, and given my ad background and my experience as an entrepreneur, I felt that really, founding an organization like True Native Media to really help connect those mid-level shows with advertisers was something that was really up my alley and something that I could really contribute. And so that’s why I founded the organization.

Adrian Tennant: What services does True Native Media offer?

Heather Osgood: So True Native Media is a podcast representation firm which means that we represent podcasts. So currently we work with about 70 different podcasts in the industry and our role is to connect those podcasts with advertisers. So we work with agencies, we work directly with brands, and go about getting advertisers in any way we can for those podcasts that we serve, as well as the advertisers that we serve. But really our focus is to try and fill the podcasts we represent up with ad messages.

Adrian Tennant: Heather, you’re not only involved in the representation of podcasts, but you also produce and host a podcast of your own called The Podcast Advertising Playbook. What topics do you typically cover? 

Heather Osgood: So I created The Podcast Advertising Playbook, because I wanted to share with the world as you can tell, by listening to this episode, I could talk about this for hours. There are so many different topics to be covered. And so I started that podcast specifically to talk about the ins and outs. What is dynamic ad insertion, and how can that serve you? How can you find podcasts to purchase when you’re looking at creating success? What does that look like? How can you track results? What does privacy look like? So we cover all of these important topics and I would say part of the most fun of producing that show is interviewing other industry experts. So we talk to people from these attribution companies, we talk to other  brands and we see what kind of experience are they having in the podcast ad space. What have they done to perfect the results that they’re getting? So it’s really meant to be a place where if people are interested in learning more about how to utilize podcast advertising and make it effective, that they can go to the show. 

Adrian Tennant: Now, do you think the experience of regularly producing your own podcast helps you relate to the challenges many other podcasters face?

Heather Osgood: Oh, absolutely. Yeah, I think it is. It’s been great. So I want to say that we’re on episode 35, I will be totally transparent and that I have lots of help with the show. So my marketing team is very effective in helping keep me on the straight and narrow. And what I mean by that is actually produce those episodes because that’s one of the hardest parts about a podcast is you have to produce regular episodes. And I think, oftentimes, when people imagine starting a podcast, they think it sounds like so much fun and it’s going to be so easy or it won’t take that much time. And realistically, it is a lot of work. And so it’s been nice to go through the whole experience alongside the podcaster, and really understand and identify what you know, their needs and concerns firsthand. 


Adrian Tennant: Taking advantage of a career hiatus, Heather combined her love of podcast listening with her professional experience in the advertising industry to seize a new opportunity, one which she uses her own podcast to promote. You can find the full interview with Heather Osgood on our website with the publication date of November 13th. Some of the earliest adopters of podcast advertising to acquire new customers were direct-to-consumer brands. DTC has been a recurring topic on IN CLEAR FOCUS throughout 2020. In October, I discussed the findings of Bigeye’s National Study of CBD Use with Alexandra McClay. Having worked in marketing leadership roles for Johnson and Johnson, Elizabeth Arden, and Burt’s Bees, Alex is now launching her own direct-to-consumer brand in the CBD and supplement space.


Adrian Tennant: What first sparked your interest in CBD as an ingredient for beauty and wellness products?

Alexandra McClay: I think my first interest was sparked, quite frankly, on a personal level. Once I found out that my mid 70 year old father was using CBD on a daily basis, it piqued my interest. And so I quickly started to study up on the benefits of CBD and started to become  sort of a connoisseur of taking CBD myself. And from there, really just looked at all the multi-benefits of this new active ingredient in what it could do for the industry that I’ve been in my whole career in beauty and wellness. And so from there, as I continued my journey and educating myself in the space, I was bridged to large cannabis companies that were looking to develop branded products within the beauty and wellness space. And from there everything just started to explode.

Adrian Tennant: Are there any special considerations for how products containing CBD designed for application to the skin need to be formulated?

Alexandra McClay: Absolutely. And what we’re doing that we think is a little unique and proprietary is that we actually have some technology and some patented delivery systems that are enabling us to formulate in a new and more novel way with the CBD. Mainly a lot of CBD you’re going to see is going to be oil-based. And would you get it’s problematic if you want to have a water-based formula for any type of skincare products or even a vaginal lubricant, it’s more natural to be water-based. And so we have a water-soluble, a sort of nanotechnology. We also have a delivery system that helps penetrate deeper into the skin that is more efficacious in terms of the delivery method. And so you’re going to get faster, better relief, but it’s a little more challenging to formulate with because it is a powder and it’s an encapsulated powder and it can, at times tweak the formula in terms of the scent or the aesthetics. And so we do have to play around quite carefully with the different aesthetics. It also helps to have a very high quality CBD, but at times the higher quality CBD might have more of that hemp aroma. And it’s a little more difficult to formulate a way from having that really strong, hempy aroma. So there’s a lot, it takes them a long time and a lot of careful consideration to really design something that you’re putting on the skin because you want it to not only feel great, smell great, but work really well.

Adrian Tennant: Lifestyle guru Martha Stewart launched her own CBD wellness line in partnership with a Canadian company, Canopy Growth Corporation, sold online through Canopy’s site. The line includes flavored oils, soft gels, and gum is apparently inspired by French baked goods, including blood orange, cheesecake berries and cream tartlets – sound delicious! Alex, is Martha Stewart’s involvement designed to appeal to an affluent female demographic do you think, or is it more about connecting with Boomers?

Alexandra McClay: That’s a great question. I think, specific to Martha Stewart, her brand I think really does span across multiple generations through some of the partnerships and work that she’s done with Snoop Dogg. I think there’s a Boomer appeal. There’s certainly a Gen X appeal, which is my generation, who grew up listening to Snoop Dogg. So I really think that in general, when these large companies are looking to utilize, whether it’s Martha Stewart or Rob Gronkowski or any of the other celebrities, I think it really is about one dispelling any myths, making CBD mainstream, and also it’s about what size of a megaphone does that give you as a brand? I don’t recall the exact number of followers that Martha has, but it’s in the millions in social media. And with some of the restrictions that are placed on advertising for CBD, having a celebrity who can speak to the masses just helps generate that brand awareness. As well as creates a comfort level for people who are canna-curious and want to jump into trying the products. So as it relates to Martha Stewart, they are looking at her to have a broad appeal across different gender bases and different generations. 


Adrian Tennant: Inspired by her father’s experience with CBD, Alex used her business knowledge of the beauty industry to create an entirely new brand designed to appeal to customers, seeking multifunctional benefits from skincare products. You can hear that interview with Alexandra McClay as part of our podcast episode about Bigeye’s National Study of CBD Use published on October 16th. Staying with direct-to-consumer brands, in early October IN CLEAR FOCUS featured a true pioneer in the DTC space. Olivia Canlas is the co-founder and CEO of Meowbox, which she launched back in 2013. Olivia spoke to us from her company’s offices in Vancouver.


Adrian Tennant: Can you tell us a little more about what Meowbox is?

Olivia Canlas: Of course. So I like to think of Meowbox as monthly deliveries of cat happiness. So it is a box full of themed cat toys and treats that we choose exclusively for our subscribers. And we deliver that monthly or bi-monthly  in the subscription model.

Adrian Tennant: Now back in 2013, when you launched Meowbox, direct-to-consumer wasn’t nearly as well established as a business model as it is today. What inspired you to start a subscription box for cat owners?

Olivia Canlas: I was a subscription box customer maybe two or three years before I thought of the idea of Meowbox. I was a subscriber to cosmetics. So I knew that was something that appealed to me, to my friends, people in a similar demographic as I was. And so I was aware of the concept of subscription boxes, but specifically like the moment where I thought, “What there needs to be is a Meowbox in this world” was when I started getting targeted on my Facebook for a dog subscription box. And I thought, you know what, instead of just ignoring it, thinking that doesn’t apply to me. I don’t have a dog. I wondered because I’m more of a cat person, I wondered if there was a box for cats and upon my initial research there wasn’t a box that was dedicated just to cat parents.

Adrian Tennant: Clearly the business is successful now, but looking back, do you think being a woman meant that you faced additional challenges as an entrepreneur?

Olivia Canlas: I like to think that everything that I do and that I did to build the company It’s not tied to gender in any way, but I didn’t look at my gender as something that was going to hold me back from succeeding. But in reality, there were a few moments where I was reminded that maybe I might be viewed a little bit differently in terms of, you know, male versus female business leaders. And one example that I can think of was I was at a trade show once looking for some new product with my co-founder, who’s male and a handful of times, the brand representatives would initiate the conversation, speaking to him instead of me as if just automatically thinking that he was the one who was the decision maker. And it was just something that I noted. I wasn’t like offended or insulted, but it was definitely something that I noticed at the time and just little things like that. I mean, very easy for me to step in and  let them know I was the one who was doing the product selection. So it could have just been like a subconscious behavior of people to expect maybe that it was the male who was in charge of making the decisions.

Adrian Tennant: Now in the seven years since you launched Meowbox, have things changed for women interested in starting businesses, do you think? 

Olivia Canlas: Yes. So it’s a lot more commonly seen or at least that it’s apparent to me that there’s more women who are heading businesses. Now, I don’t know if that’s just because I’m exposed for it. Maybe I might have my eye out for that, but I know so many more women-led businesses and female entrepreneurs than I did years ago. Now it could be the way that the landscape of business is changing and it’s just something that was being more brought to our attention. Maybe women in business are being highlighted more than they used to be. Which may in turn encourage more women to want to aspire to be in charge of businesses and turning their ideas into businesses. But definitely from when I started my research into subscription boxes and pet businesses It was a lot more men  leading those industries as opposed to now. And now I just have an endless contact list of colleagues who are women who own businesses.

Adrian Tennant: So Olivia, what inspires you on a daily basis? Are there any journals, podcasts, or social media accounts that you follow – cat related or not? 

Olivia Canlas: You know what? I have to say, my source of inspiration comes from my fellow female entrepreneurs. I have a small group of female entrepreneurs who I look up to whose businesses I follow, whose social media I follow. We’re in communication for best practices or problem solving advice and that kind of thing. And It’s really blossomed and become a resource for me that I’ve come to you know, rely on and go to as of late. And I guess I didn’t really realize how important it was, maybe in early years to have that kind of a network of colleagues. But as time goes by, it’s just, I don’t know, maybe you lose a bit of your ego and are just more open to sharing your challenges with other people, especially people who have, maybe dealt with that before people in a similar businesses to you, and that’s where my inspiration comes from. I see ladies who are running businesses that do certain things better than me, or certain things that I’ve never done before. And I’ll ask “how can I do that? How did you reach that?” And then, and vice versa, it’s the same where there’ll be something that I’m doing really well at Meowbox. And they asked me, “How did you do that? What tools did you use to reach that?” And it’s just this feedback loop of all of us sharing and each of us supporting each other and just doing better and better.


Adrian Tennant: Olivia thought about her personal experience as a makeup subscription box customer and saw the opportunity to apply the same business model to delight cat owners like herself. During the full interview, Olivia is very candid about what marketing tactics work and what doesn’t work in the DTC space. You’ll find it on the IN CLEAR FOCUS page with a publication date of October 9th. I hope you enjoyed this recap of some of the inspiring stories we heard this year from successful female entrepreneurs. My thanks again to all the guests you heard in today’s episode, Kristen Wiley, Holly Kapherr, Heather Osgood, Alexandra McClay, and Olivia Canlas. As always, you’ll find links to the resources we discussed on the IN CLEAR FOCUS page at under “Insights.” Just click on the button marked “Podcast.” Thank you for listening to this, the final episode of IN CLEAR FOCUS for 2020. I’ve been your host, Adrian Tennant. We’ll be back with a new season of IN CLEAR FOCUS in mid-January. So until then, goodbye!

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