Today’s guest is serial entrepreneur and influencer, Zoe Barry, who discussed her previous startup company ZappRx, as well as her new startup, Zingeroo. Zoe explains her career path from her first job on Wall Street to starting her first company at 26 years old, for which she raised over $42 million. Tune in for Zoe’s insights on starting a company inspired by personal obstacles, how to know when investors are the right fit for your company, and building a valuable social media presence.
Transcript:
Zoe Barry [00:00:01] I ultimately ended up founding my first company when I was twenty six years old and that was based on a personal experience, I raised forty two million.
Sam Jayanti [00:00:12] Welcome to Ideamix radio, I’m Sam Jayanti. And every week I chat with entrepreneurs, solopreneurs, career changers, experts and enthusiasts for insider tips that you can apply to turn your idea into a business. So sit back and enjoy today’s show. Zoe Barry is a serial entrepreneur, mentor in residence with Techstars and angel investor. She’s currently the CEO and founder of Zingeroo through her second venture backed tech startup. They’re currently operating in stealth mode and have raised over five and a half million dollars to date. Zoe, thanks so much for coming on to Ideamix radio.
Zoe Barry [00:00:54] Sam, thank you so much for having me. It’s been such a journey. I’m so excited to be back and share more about my new business and the progress we’ve made in a few short months, as well as some other side hustles that I’ve been doing. So thank you so much for having me. I’m really, really thrilled to be here.
Sam Jayanti [00:01:13] Wonderful. So your entrepreneurial journey, zoe has included being a founder, being a mentor. More recently, you’ve been an angel investor in a series of different companies and increasingly an influencer on Instagram. Tell us about that journey and that mix of things in your own words.
Zoe Barry [00:01:30] Sure, I’d definitely say I’ve zigged and zagged a lot in my career. I got my career start on Wall Street. I worked first for a broker dealer and then for a hedge fund, and that was a really exciting experience, being, sitting next to the trading bullpen. Very dynamic, lively start to my career. But ultimately, in one of the one of the jobs I was in, I felt that I wasn’t really being paid equally and I felt very stunted in my career. So I moved on from there and that’s where I kind of went on a series of adventures. It was a recession when I started exploring other career opportunities and really sort of testing what did I want to be when I grow up, quote unquote? I ultimately ended up founding my first company when I was twenty six years old, and that was based on a personal experience. I raised forty two million for that company. It was just about an eight year journey. ZapprX was the name of the company and it was acquired last year. And then I kind of hit pause and I went on what I call an entrepreneur sabbatical, and I really was again kind of trying to figure out what did I want to be when I grew up? And something that I was really passionate about was changing how funding has been distributed. So I started writing my own investor checks and I started collaborating with other female entrepreneurs, and I created this little group called Double X Angels. And our focus is on writing checks to first time founders, you know, really helping be that first check in the door for a woman and with her venture and helping build and create that first round. I found that it was hard to just mentor people one off, so I began building more of an Instagram presence so that I could quote unquote spread the word and be more helpful and provide my tips and tricks to more people. And that’s been a really exciting journey. Also, a hard one because it’s one thing to mentor somebody one on one, but it’s another to try to create content and expand your knowledge and and make it more available and accessible to people who maybe aren’t exactly startup entrepreneurs themselves and might not know all the terms. And it’s been exciting to do that. And now I’m at my My Next company, which is in stealth mode. But I keep angel investing and I keep building my social media presence.
Sam Jayanti [00:03:51] Fantastic. Love that mix. We keep hearing about the difficulties of female founders getting funded, and there’s no question that the gap between male and female founder teams getting funded still remains super wide. That said, there’s an important amount of progress that’s been made between 2010 and 2020. VC funding for companies that included a female founder almost doubled from eight percent to almost 16 percent and absolute dollars invested in founder teams with women, even though they grew at a lower rate, they still went up from seven to 11 and a half percent. You’re someone who did get your first company successfully funded, as you were saying, and you’ve also now been successful with your second. Tell us why, looking back, you think you’ve been successful given the structural inequities that so many female founders face?
Zoe Barry [00:04:43] Ooh, that’s a great question. So if I think about it, I’ll be honest, and I think I had a tiny bit of an unfair advantage and that unfair advantage is that I hailed from Wall Street. So I was an investor. I wore that hat for a number of years. In fact, more than being an investor, I was actually the annoying analyst that was pestering CFOs and CEOs about their projections, picking them apart, finding one thing that was wrong with it and then peppering them with questions. And so I knew what to expect as a CEO, as a as a startup founder because I had been that annoying analyst. But then beyond that, as the analyst, I, I presented by findings internally to fund managers and I saw when they traded or invested, i.e. when deals got funded and I knew what the conversation was behind closed doors, and I was part of that debate and part of that experience. And so I had a slightly more trained ear when investors were asking me questions because I understood what their thought process was and where they were going and if they were engaged or not engaged. And I think one thing that was really powerful is that I walked away from deals and I walked away from meetings if I thought they were not going well. And too many entrepreneurs will sit and keep fighting and keep trying to convince an investor to do a deal. And that is just a colossal waste of time.
Sam Jayanti [00:06:08] It’s such an such an important point, right? Because recognizing when the chemistry is there and when it’s really not, even though founders sometimes feel that they’ve got to sort of see every one of these avenues through is such a waste of time.
Zoe Barry [00:06:20] Totally. I think the power to walk away changes the dynamic because once an investor starts going down a series of what I call prevention questions and there’s been a lot of great research done, there’s an HBR article Harvard Business Review promotion versus prevention questions. Once investors start going down a prevention question path and they ask like three, maybe four prevention questions in a row, what they’re signaling is my mind is made up. I don’t want. I don’t believe in your idea and I’m not going to invest, and they’re just trying to pass the time and run the clock. If you pause in meeting and say, Hey, thank you so much, I really appreciate your time today. It doesn’t seem like this idea is a good fit for your portfolio, and I really don’t want to waste your time because you are such a great investor and you obviously have a really great portfolio that you are cultivating. And I want to make sure that you can give that time back to your current portfolio. I also have other investors that do believe in my idea, and so I want to go spend more time with them so that I can build this business, and it’s OK that we’re not a fit for each other. You say it with grace, you say it with humility. You do not sprout any diminished demonic ego. And as women, unfortunately, a lot of things can, sometimes, if you’re assertive, can be flipped and turned into aggressive. In terms of how messaging receives, you have to say it with such kindness and grace. It will flip the power dynamic in the conversation, and investors become very, very curious. If you are willing to walk away from money, that means you probably have something really fucking good and they’re going to want to know more, and it changes that power dynamic.
Sam Jayanti [00:07:55] It’s excellent, excellent advice. I think so many founders feel on particularly female founders feel that they can never walk away from these conversations, and I think you’re really stressing that there is power in doing that, but also in being analytical and learning to recognize when, as you said, you know, the prevention questions have sort of begun and you start going down this rabbit hole, that’s just unproductive.
Zoe Barry [00:08:22] Yeah. And the other thing I would say, two things are important because you mentioned female entrepreneurs and I want to provide more tools to to women who are listening out there. I went after really big ideas, ones that you could absolutely point to one hundred million dollar business model. And at scale, quote unquote. And you really any entrepreneur, regardless of gender, has to be going after that. So if you’re doing an athleisure company and you need to be pointing to Lululemon right, you need to point to rent the runway. You need to point to real brands that have grown to massive revenues. If you do a product that is unique to women, it becomes much harder for men to lean in. So I personally invest invested in startups like Twenty Eight Health or Astrid Health or Pixie Cycling. These are women’s health startups, so things with your period or birth control, it makes it hard for men to understand what those products are because they don’t get their period. So you are creating a higher bar for yourself, not saying it’s not a valid market. Please, listeners don’t hear that. It’s just harder because men are typically investors and they find it very hard for it to resonate. So you have to speak to them in terms how they would quote unquote get it. So if you can show them a really big, publicly traded company or show the division or understand the metrics behind Tampax, for example, right, you can show how big that division is, or you can show how Big Birth-control is within the prescription health care market. It shows them how, how much of an opportunity it is, and it shows a path to a hundred million dollars in revenue. So sometimes you can pick these ideas for women. You just have to also make sure sure you talk about the business in a way that shows how big it is.
Sam Jayanti [00:10:14] Yeah, two important points, right? Pick a big enough target market and know your audience, right?
Zoe Barry [00:10:20] Yes. And the last thing I’ll say is don’t do too many copycat ideas. There’s a lot of people who ask me early on if I was doing like, for whatever reason, I do not know why. Maybe because I am I like clothing and I like to consider myself a petite fashionista. But if I had a dollar for every sort of rent the runway knockoff pitch that I’ve heard when I speak at HBS events or mit events or other business school events, it’s overplayed. And the number of people who thought I was doing like a version of that as my first startup was just insane and I was doing digital health and prescription drugs and data. I had nothing to do with fashion, but there is an element to don’t pick an idea that is super, super overplayed in the market because people will just roll their eyes and it can be rent the runway, or it could be ridesharing, or it could be food delivery service. Overplayed ideas generate a lot of eyerolls.
Sam Jayanti [00:11:24] Totally makes sense. You started ZapprX in 2012. So what made you want to do that? You talked about sort of a personal need behind starting that company or a very personal motivation. Tell us a little bit about that.
Zoe Barry [00:11:38] Yeah, I think every time someone is willing to quit their job and not have health insurance or a paycheck, they have to be really, you know, crazy passionate about something. And that was certainly the case for me with my first startup, which was ZapprX. For those of you don’t know, it stood for Zoe’s prescription app RX means prescription in the health care world. And I basically had a family member that was diagnosed with a severe disease and needed access to a life saving, life altering medication. And despite us living in New York City, seeing the top doctors, having health insurance, speaking English and understanding what these crazy words were that seemed so esoteric, like prior authorization and clinician consent and patient sign off, we had all the tools and all the advantages. It took six months for my family member to get this medication. And in that time period, he deteriorated really rapidly. And that it was just gut wrenching to watch. And it felt like sand, you know, slipping through your fingers every day would call the pharmacy or the doctor or the health insurance. And we get another story and we felt like we were almost there. And then it would slip through our fingers. And watching him deteriorate was maddening and gut wrenching. And then once he got the drug, it was like Snap the fingers, made a full recovery. It was unbelievable. It was just incredible. And so it really showed you the power of prescription medications at the same time as showing you how broken the health care system system is. And so from there, I ended up founding this company, and the idea was basically the Amazon Prime for hundred thousand dollar life saving medications. I figured I couldn’t change the price of drugs. It is what it is. The system is too broken, but I could at least fix the access so that patients didn’t have to bear the burden of waiting. And that was really the idea for ZapprX, and we did. We were very successful. We use data to show the risk profile of patients and what happened if they didn’t get access to the drug. And that’s what made insurance companies want to pay for the drugs. Once you wait, the statistical likelihood of an adverse event or a poor outcome or a hospitalization, i.e. increased health care costs is what made health insurance pay. And we were able to cut fulfillment from an industry standard of six weeks down to three days. So it was it was really, really meaningful. And I was I was pleased with how many people I could help and support with this idea that that really grew out of a really tragic pain point for my family.
Sam Jayanti [00:14:23] I mean, you identified a pain point that afflicted a large enough target market and then really addressed it in a data driven, solution oriented way. Let’s take a quick break. Zoe, I want to quote back to you something that you said about starting ZapprX. For me, it was one of those moments. Don’t hate the player, hate the game. I wasn’t going to change my gender. I wasn’t going to change my name and puts up my lifes on hold to get a master’s degree of some sort. I figured out how to game the system and make it work for me. Tell us a little bit more about what you mean by gaming the system.
Zoe Barry [00:15:01] Sorry, yes, I love that. That throwback. So for me, one of the things I found is that I mentioned I was twenty six years old. When I founded ZappRX, I didn’t have a medical degree. I was not a clinician of any sort. I was not a doctor, I was not a nurse. And yet I had this idea to have a prescription system. E-Prescribing is what it’s called an industry lingo for doctors and nurses to write prescriptions and for pharmacists to fill it. I also did not have a business degree. I didn’t have my MBA. So was I going to go back to school and get those two things? Absolutely not, because in the period of time that I would have done that, the market would have changed and we wouldn’t I wouldn’t have been looking at the same white space. Lastly, I was a woman who didn’t code was founding a tech company, and all of that seemed, you know, quote unquote outrageous, combined with the fact that I didn’t have any degrees or sort of resume that indicated I could build and scale a business and raise money from venture capitalists. But what I figured out was how to game the system. So I figured out that if I could get a doctor or a nurse to share their experience with the investors, the investors perked up and paid attention. I pulled the reports that showed how big the market was from reliable sources that I knew that these investors read and believed in. So I figured out ways to get this information to them to make it credible. It didn’t necessarily have to come directly from my mouth. It could come from. Again, one of these clinicians mouths or from the data that they trusted. And last but not least, I like to joke that the system suffered from old male doctor system OMDS. And I found that if I brought a really powerful salt and pepper or no hair male doctor, it radically changed conversations with investors as well as with customers. But the key thing was these doctors knew the role that they were playing. I was pretty transparent about the challenges I was facing as a young female. They didn’t care. They thought they thought it was laughable. And they love the fact that I was hacking the system and they were happy to be my partner in crime.
Sam Jayanti [00:17:25] Because they were viewed with more seriousness and greater credibility.
Zoe Barry [00:17:29] Yes, exactly. But they also felt just like I didn’t feel listened to in VC meetings or customer meetings when people thought, you know, she doesn’t know what she’s talking about. She she’s young and doesn’t have a master’s degree, and she’s not a doctor or a nurse. They also didn’t feel listened to because they are doctors who are running clinics where they can’t get patients on therapy. So they’re calling the insurance companies. The nurses are calling, they’re calling their hospitals, asking the administration to do something. They’re buying billion dollar EHR systems that don’t support them, and they’re so frustrated, too. They also felt not listened to. So the first time there was all of a sudden a person who walked in their door and said, This system is broken and I want to fix it, but I need help you help me help you. So it was really a symbiotic relationship, I would say.
Sam Jayanti [00:18:24] That’s key, right? Building this symbiotic relationship and really getting people onside for who you’re solving, you’re not only solving their problem, but you’re also giving them an opportunity. And I think this is something that founders don’t do remotely enough, which is put some of their stakeholders in front of investors to actually explain what the company or what a solution is doing for them. Because, you know, either people just don’t think about it or they’re too ego driven or whatever the reasons are. And it’s such a powerful key tool with investors for them to actually understand the value that you’re delivering.
Zoe Barry [00:19:04] Absolutely.
Sam Jayanti [00:19:07] So so let’s shift gears a little bit. Over the course of all the various things that you do and ends up, our guests tell us about an instance where you realized that a particular direction or a strategy you were deploying wasn’t working and you had to make a change or pivot.
Zoe Barry [00:19:29] Great question. I’ve got I’ve gone through a few of those. I think the one that that comes to mind that’s probably easiest to describe is a business model pivot. So with my first company we were looking at, we had a great idea for a product which is, you know, get a prescription written much faster, show the data, shorten the time to fill. But the key question was how who who is the paying customer? Because there’s a lot of users of the product, but which customer pays and then what is the various mechanism for which we collect money? So the two different models that we honed in on was one that was transaction based get paid for every prescription that was written versus data based, which is offer the entire system for free, but collect and own all the data. From there, you can monetize to various sources. Essentially, one of the key points that we were debating is do we want revenues upfront or do we want to push revenues out, build something? It’ll take much longer? It’s unknown. Key question can we actually get the data? So that’s a sort of lightning bolt or third rail at times, particularly these days, but less so a couple of years ago, although with health care certainly always an issue. And so therefore revenues upfront, smaller revenues, revenues in a long time. Question mark if we can get the access to that data, much, much larger business opportunity. And there’s entire HBC Harvard Business School case study on this exact point of inflection with ZapprX my my company. Ultimately, we went for the data play and the company that acquired ZapprX is minting money off of the data. I can, I can say through trusted sources. So we ended up being right. I would also say it resulted in us raising a lot more venture capital money. And the downside that I was not paying attention to when I was going through this pivot was how much control I would give up. I’m shooting for the Moon. What’s called often attack a moon moonshot going for this much bigger play. And what I would be sacrificing as a result of that.
Sam Jayanti [00:21:53] So talk a little bit more about that, I think. You know, you’ve made two really interesting points, right? One is that even though building this compelling set of data for which you couldn’t necessarily see all the uses as you were in that build process, it’s turned out to be incredibly valuable. It was the longer term, more expensive, in some ways more risky play, and that was the decision you made and went for. And that turned out to be absolutely the right decision was highly monetizable and has really delivered value to the acquirer of Zapprx. But at the same time, I talk about what did you what made you come to that decision? You know, was it advice from other people? Because in many ways, you know, founders are often given the advice to think about monetize ability and sort of what is going to deliver cash to help you keep growing. And as you said, you know, retaining control and you had to sort of undergo, you know, or decrease your control over the company in order to achieve this vision. Talk a little bit about that.
Zoe Barry [00:23:04] So the board was in favor of the big play, the data play. And one of the people that we had on the board was Jeremy Levin, who’s the former CEO of Teva Pharmaceuticals. So one of the largest top 10 global pharmaceutical companies in the world. And then I had some management team members who had built and scaled various health care startups. And the tension was the team wanted to do the quote unquote easy transactional path. And myself, as the founder and the visionary person who sets the vision for the company and the board wanted to go for the swing for the fences play, the way that broke down was me firing the team at the end of the day, the people who didn’t believe and were not going to get on board with the pivot. And bringing in players who had the risk appetite, but also the experience to go, build and execute a data play. And so it resulted in shifting the DNA of the company a bit or dramatically of the leadership levels. It didn’t actually results in change through the ranks. It was more the leaders of the operations and finance department because for them, they they’d been through several start ups that had failed. And so they thought this was a really big opportunity and a large market. But they wanted cash and they wanted it upfront and they wanted it to be easy. I will say that once it all played out, the acquiring company is making the most off of the play. It was the right play. It was the right product, the right business model. But I mentioned that I gave up a lot along the way, and this is where sometimes learning the understanding the motivations of all the players, the table is very important. And one thing I misunderstood was how much I would give up in terms of control raising a lot of money and how I would give that to people who were not even at the table yet. So I ended up raising money from new investors to come in that wrote big, big checks. And when I did that, those people were not in the room and we were having the conversation and they were an unknown and they ended up being individuals who I would say were not as helpful to the growth of the business as they could have been.
Sam Jayanti [00:25:34] That’s super helpful, thank you. We’ll be right back. Zoe let’s talk a little bit about your both role as, but also how you’ve become an influencer. You, I think, identified that it’s been a very important component of sort of both your leverage, your ability as a founder and entrepreneur, and also a key aspect of how to mentor at scale effectively. Tell us a little bit about the thought process, how you’ve driven that over time, how it’s evolved.
Zoe Barry [00:26:14] Another wonderful question, Sam. Thank you so much. So I was towards the tail end of ZapprX. Of course, I didn’t realize it was the tail end and of the company’s journey, and I had almost no social media presence and I was taking all these meetings and mentoring entrepreneurs and doing office hours on Friday and writing checks and giving back. And I just was all of a sudden very overwhelmed that I wasn’t doing enough and I had accomplished so much, and I needed to get that message out there in a much bigger way. So I began building my Instagram following more seriously on my. My Instagram handle is at @zoebarryceo. So feel free to check it out. It’s actually the same on Twitter. And then I have a pretty significant LinkedIn following as well. What I found interesting is that I could really seamlessly tap the LinkedIn following because I it was business oriented. I was in business. I used it for hiring, networking, raising my profile with venture capitalists and investors and customers, et cetera. But my my social media on Instagram was really lacking, and I was really struggling to keep up. And part of it was just the time, commitment. And what I realized is that I needed as a as a tech CEO and as a woman leader, I needed to have a professionally curated managed, Instagram, social media, etc. But Instagram was an area that I could really tap into more women specifically, and it was a balance of time. I was, I would call it reactive posting. I’d wake up in the morning like bleary eyed one eye open and be like, What day is today? I say Monday, OK, hashtag Monday motivation. Let me just scroll through my favorite photos and the past couple of years that I casually took on an iPhone, grab one and create a post and throw it up there. That is not the way to manage your social media. That is very poor planning. And so I’ve now shifted to a more professionally managed social media, which I can talk more about, but I really decided to figure out what is what is it I need out of social media from a business perspective? And how am I going to to execute that?
Sam Jayanti [00:28:35] So what did you do once you figured out what you needed from a social media perspective?
Zoe Barry [00:28:39] I ended up incorporating another company, and finally, I should say that again, because the meetings they went off on, I ended up incorporating another company and financing it. I don’t run it. I don’t have an operating role, but I hired three people to go out and build a professionally, a company that helps people who are busy, people who have full time jobs create and manage professional social media platforms. So any platform be that Twitter, LinkedIn, Facebook, Ticktalk, Medium, if you want blog post done and you can pick one to three platforms and the team will help help you do that. The idea is to figure out what are your pillars. So I only post now on three pillars founder, fitness and fashion and founder is the sort of business tips and tricks that enables me to mentor and teach more people fitness to show work life balance. Don’t burn out. Here are all the things that I need to do. Be that workout to take a break and have a clear headspace or healthy eating. And here’s food as fuel, and here’s how I get through my day and don’t get a food coma. And then fashion, fuck it. I worked this hard. I’m successful. I want to go out and buy a pair of Louboutins. And you know what? I’m going to enjoy it. What was that?
Sam Jayanti [00:30:00] I said and you enjoy it.
Zoe Barry [00:30:02] it like that is my reward that is my light at the end of the tunnel and anyone who tells me I need to be in a suit looking like, you know, a man behind a desk, they can go pound sand. That is not what I’m about. I’m about working as hard as possible and enjoying yourself and leaning in to whatever crazy, wild, colorful butterfly of a lifestyle that one can have. And I feel about that. That combined message is really powerful, and it reaches a lot of people because it hits them across various points where they’re seeking motivation or inspiration, or you know that they can go out and do it too. And so the team that I’ve hired now handles all the content planning and presents it to me to make sure that it’s on trend with my voice. They actually attend meetings with me, be that startup pitches or venture capitalist meetings or anything so they can hear my voice. And then they write the post presented to me. They pull the photos, they create everything so that I’m now approving it. And what I found is that it’s done in a much more professional level. It is way beyond the skill set that I had because I didn’t have the skill set to do the content planning plant plan for the the the three pillars, be the person in the business meeting while simultaneously trying to take notes and capture that in an Instagram post. And it’s just way more, way more effective at this point.
Sam Jayanti [00:31:29] Fabulous. So, Zoe, last question. Where do you see yourself and your business, as well as all the other things that you do three years from now?
Zoe Barry [00:31:38] Well, if I were making a bet, I would say I’ll still be building Zingeroo. And I will be helping with many, many more startups. In particular, I’m very passionate about investing in women, so I hope to be at a point where I can write much larger checks and collaborate and have a bigger platform so that more people will join in on the checks that I write on and more women can get funded because I want to, I want to really be a positive change and a tool to help shift the funding dynamic, not just a squeaky wheel complaining on the sidelines about the statistics. And I think that’s not enough. I think you have to actually write a check and be part of the change actively.
Sam Jayanti [00:32:20] 100 percent agree, I think, you know, identifying the problem as only 20 percent of of the way there and then actually crafting, embracing and executing on the solution is is what actually solves any of these problems. Here’s something else you should know. Serial entrepreneurs end up establishing around 20 percent of new firms and have a far higher success rate with their new companies than other founders. Thanks to Forbes, Pitchbook and the NBER for the data used in today’s episode. Zoe, we love your story because you responded to the words, no one’s ever done it this way before, With both determination and enthusiasm and a totally Can-Do execution oriented attitude. Thanks so much for being with us on the show today.
Zoe Barry [00:33:10] Thank you so much for having me. I can’t wait for the next one and we’ll see all the progress that’s been made.
Sam Jayanti [00:33:17] Thanks for listening today. You can subscribe wherever you get your podcasts. And while you’re there, please do review the show. We love hearing from you, so e-mail us at info@theideamix.com Or Instagram DM us. Our episode this week was produced by the incomparable Martin Malesky, with music by the awesome Nashville-based singer-songwriter Doug Allen. You can learn more about Doug at DougAllenMusic.com.