Genevieve Bellaire - Founder & CEO of Realworld: Transitioning from B2B to B2C, Launching a Zero to One Product, and Creating a Category

 Genevieve Bellaire 00:00
It was one of those things where I thought about it for over a year and just couldn't really get it out of my head, and started to de-risk it by doing market research, by doing early customer discoveries, or talking to people in their 20s, and figuring out, "How do you figure out the answers to these questions, or how do you solve these problems?" And it was just very, very clear that, one, there was a white space, and two, if you could figure out how to create a product that defined this category, it would be a massive success.

Callan Harrington 00:30
You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flash Growth, and I couldn't be more excited that you're here. Welcome back everyone to another episode of That Worked. This week, I'm joined by Genevieve Bellaire. Genevieve is the founder and CEO of Realworld. Realworld is your companion for navigating the journey of adulthood. They help you get it together by simplifying and streamlining your finances, health, career, and household. Prior to Realworld, Genevieve received her JD and MBA from Georgetown University, and she also spent time at Goldman Sachs before ultimately launching Realworld. I really enjoyed this conversation. Genevieve has built a product that I can honestly say, that I wish I had when I was younger. We talked about how she built that product as a non-technical founder, and then we also dove into how she brought a zero-to-one product to market. For our listeners that may be unfamiliar with that term, a zero-to-one product is a product that didn't exist in the market until you specifically built and launched that product. And it comes with a host of challenges, but also a ton of opportunities. And I love diving into this with Genevieve.

We also talked about how Genevieve made the pivot from B2B, so business-to-business, to B2C, business-to-consumer, and that is a really big pivot to make as a company. And I really enjoyed hearing both how she made that pivot and then how she's approached other big changes within Realworld throughout the years. With all that being said, the part of the conversation that I love the most was talking through Genevieve's journey of creating a category. Oftentimes, when you have a zero-to-one product, you also have the opportunity to create a category. And I'm sure anybody that's founded a company has heard about all the massive benefits of creating a category, but I love talking about the challenges that Genevieve had to overcome in order to pull this off. For example, it sounds great to not have any competitors, but Genevieve brought up some interesting challenges in regard to that that I just wouldn't have realized would have existed. And I would say it's a great listen for anybody that's focused on creating a category, and I really enjoyed it. So with that, let's get to the show.

Genevieve Bellaire 03:20
Genevieve. I'm really excited to jump into this, and one of the areas that I'd love to kick this off in is on the health insurance side. Tell us about your experience with double paying for health insurance.

Genevieve Bellaire 03:25
For sure. So this was one of, frankly, many moments that led me to found Realworld, where I found myself as a hopefully relatively competent, you know, educated person who just had no idea what they were doing when it came to a real world, adulthood-oriented topic. But basically, early in my career, I'm a lawyer by background, so I went to law school straight after I graduated from college and did a JD-MBA before beginning my career. And so you may or may not know this, but when you're 26 years old, if you're on your parents' health insurance plan, you automatically get dropped. And I was on my parents' health insurance since I was still in school, and I basically ended up in a situation where I was paying for health insurance via my parents and was also paying for it via school, and then all of a sudden I had, like, no health insurance, and then I had to go to the marketplace and start paying for one separately. So I went from having, like, double health insurance to no health insurance to then starting my job, thankfully, and having insurance through that. But after leaving my job, going through the COVID situation and paying thousands and thousands of dollars a month for health insurance out of pocket, so I was technically almost a lawyer who was, like, double paying for something that I shouldn't have been dealing with.

Callan Harrington 04:30
It's interesting that health insurance was one of the big motivators to start Realworld. Is that correct?

Genevieve Bellaire 04:35
Yeah, because it's one of those things where it's just really complicated, no matter where you get your insurance from. There's, first of all, all these words that you have to understand: premium, deductibles, coinsurance, copay. These are all these things you find in your explanation of benefits that it's really hard to parse through. I was like, "How is this something that we haven't learned about in school? It's a fundamental part of being an adult." Figuring out your health insurance, figuring out your finances, etc. And so it was one of those triggers where I thought, "There's got to be a better way of dealing with this and figuring this out." And it's tough too, right? Because for people, especially if you're just graduating college, financial advisors are not incentivized to work with those people. You're at the beginning of your career, and good financial advisors are typically working with people at the end of their career because they're paid off of how many assets they collect. And I'm not saying there's anything wrong with financial advisors doing that. That's the progression of their career. So there's not a lot to really turn to. Anyway, it sounds like that was definitely the case in your own experience. But did you find that as you're doing the research and such for the product itself?

Callan Harrington 05:40
Yeah, you know what was interesting was, frankly, what we think of as adulthood, as a landscape. So it's everything from finances to insurance to tax to employer paperwork, leases, all of those sort of moving pieces of life. There were simultaneously so much information online. You could Google things, you could find articles on NerdWallet. You could go deep in almost any one category. Yet there was no entry point. There was no place that just helped you figure out the things you didn't even know that you didn't know, and for particularly a recent graduate. But really, anybody who's starting out, it's really hard to understand, like, what's the playbook? What are the things I should be doing? And so that was the biggest aha moment, initially, trying to figure out how to solve this problem and simplify adulthood, which is our mission at Realworld was, "How can we just create something simple that helps people onboard into life, set up the things they need to set up, understand the concepts they need to understand, and then we can take them from there," whatever they need to do in their own life, but really help them get the fundamentals right?

Callan Harrington 06:40
Yeah, and I'm excited to dive into this more, but before we do that, I want to pull it back a little bit. Let's talk about your education. You went to Princeton for undergrad. You've got your MBA and JD from Georgetown, and I'm assuming you're in the investment banking program at Goldman Sachs. Is that correct?

Genevieve Bellaire 06:50
I was actually not. I loved my job at Goldman Sachs, by the way; it was an amazing company to start out at, but I had a very unique opportunity to work within the executive office, which kind of sits on top of the firm and does firm-wide strategy, does support around a lot of different initiatives that the company runs. And my job was actually focused on supporting, ironically enough, women entrepreneurs through a program that Goldman had specifically designed to help them access capital, provide resources from a financial literacy perspective, and really help these businesses across the country and across the world scale up and grow. And so it was a unique situation where I was able to be in and around entrepreneurship, but watching entrepreneurs as opposed to being one myself.

Callan Harrington 07:40
Okay, you put a lot of time and effort into the education that you had previous to this. You got into Goldman Sachs, right? One of the best names that you could have. Got into the career launch pads. There you were on this launch pad. Why start a business at all? Was this just something that you've just wanted to do? Or what did that look like?

Genevieve Bellaire 08:00
It was one of those things where, to be honest, I was just obsessed with this problem space. And it came to me very early on in my time at Goldman because I just started realizing, one, that there was a problem that I was facing, and then the more that I talked to more people, I realized, like, nobody knows what they're doing. So there's definitely a market here to build this kind of one-stop-shop solution to help people onboard and then transition into adulthood. But it was one of those things where I thought about it for over a year and just couldn't really get it out of my head, and started to de-risk it by doing market research, by doing early customer discoveries, or talking to people in their 20s, and figuring out, "How do you figure out the answers to these questions, or how do you solve these problems?" And it was just very, very clear that, one, there was a white space. And two, if you could figure out how to create a product that defined this category, it would be a massive success. And so it was definitely a high-risk jump, but one where I always knew if it didn't work, I could go back and have that foundation to begin again at another place in my career.

Callan Harrington 09:10
What was that step like for you? Was this where the entrepreneur in residence came in? Did that help you make that step? Or what did that look like?

Genevieve Bellaire 09:15
Yeah, exactly. Happy you brought that up. It was such a fortuitous moment where, after I left Goldman, I was thinking a lot about this space, but I didn't really know where to start, because, again, I was a lawyer working at a firm, lawyer working in investment bank. I didn't know anybody in tech. I didn't know how to code. I didn't know how to do product design. I didn't know so many things. And one of our earliest investors and advisors, Jean Case, who runs the National Geographic Society and is just a wonderful entrepreneur in and of herself, was running a foundation. And I told her about what I was thinking about and looking for advice from her. And she said, "We actually have an entrepreneur in residence program. Would you be interested in coming advising us on things related to starting a business, but also have the time and space to think about, you know, what this could look like?" And so it was an incredible opportunity, surrounded by really innovative people, like getting to interact with a lot of other more established entrepreneurs, doing my own research, all of that. And it was in that time that this idea for Realworld really started to solidify, and early versions of the product and experience and model came together.

Callan Harrington 10:25
Having gone through that, what are the downsides of taking an entrepreneur-in-residence role? Because it sounds like it’s all upside.

Genevieve Bellaire 10:30
I really can't think of one. The only downside I could possibly see is that if you get too comfortable there, having that platform and don't actually take the leap to start the business. But that wasn't a problem I had, fortunately, and I only have positive things to say about the program.

Callan Harrington 10:45
You touched on this a bit, but you're a non-technical founder. How did you navigate getting the first product built?

Genevieve Bellaire 10:50
This was definitely a journey. But I’ll also note that this was years ago, so it’s a lot easier now to be a non-technical founder because there are so many resources that you can use to very quickly design, spin up products, and get something to market in a way where you can test it. Six years ago, there weren't as many tools and resources available. All that is to say, I tried almost everything. I tried designing things out, screens on Envision, and other tools like that. I put those in front of people to see whether the whole idea resonated. I worked with contractors, dev shops, all sorts of different people to try and spin something up. It was challenging because I hadn't raised any money, so this was all bootstrapped from my own finances, and I was trying to learn as quickly as possible. But when you’re non-technical, it’s hard to rapidly iterate on things because you're in more of a project-based engagement with the types of folks you work with, so it slowed me down a bit in the beginning. But once we started to really see signs that there was something here and started to build out more of the team, those challenges went away.

Callan Harrington 11:55
You talked about minimum designed product, which I thought was really interesting. If you were doing that today, how would you do it differently?

Genevieve Bellaire 12:00
Today, I would get smart on Figma, which is an incredible tool, and take courses or use templates. You can learn Figma in a couple of hours and design out mobile and web screens with interactions between them, creating a prototype. Canva’s another great tool, though it’s not as robust as Figma in terms of product design but can bring visuals to life quickly. So if I was to do it again, I’d get proficient in Figma and just start putting prototypes in front of people. There’s no need to understand code at the start; you don’t need to build anything engineering-wise, just test the concept with users.

Callan Harrington 12:45
This might be a spicy hot take question, but if you could do it again, would you try to get a technical co-founder, or would you go with the process you just mentioned?

Genevieve Bellaire 12:55
One of my biggest regrets is not having a co-founder, technical or not, because it can be a lonely journey building a business. Fortunately, at this point, I have teammates, other founder friends, and investors to answer questions and provide support. But having a co-founder with complementary skills—whether technical, marketing, or otherwise—can help you move faster. If I’d had someone who could design well, tell the story, and help build that product vision initially, I think we would have reached product-market fit more quickly.

Callan Harrington 13:35
Would that be a deal-breaker for starting a business in the future, or just a strong preference?

Genevieve Bellaire 13:40
Not a deal-breaker, but if I could find the right co-founder, I would definitely go for it. If you’re determined to build a business, nothing will stop you—even if you’re solo. It wasn’t for lack of trying that I didn’t find a co-founder; I ultimately decided to move forward and build it myself. In the future, though, I’d put more effort into finding a co-founder if I could.

Callan Harrington 14:10
Once the business starts to gain traction, it can become more complex to bring in a co-founder and negotiate equity. Did you experience something similar?

Genevieve Bellaire 14:15
Yes, definitely. Early on, it’s a binary outcome—either you build a successful product and company, or you don’t. In hindsight, I wouldn’t have worried so much about splitting hairs over equity or bringing someone in a few months or even a year after starting. I’d have been more open to the idea of a co-founder. My thinking has evolved, and I’d definitely apply that to any future ventures.

Callan Harrington 14:45
So you initially targeted the B2B space with Realworld, selling to colleges, but then pivoted to B2C. What led to that shift?

Genevieve Bellaire 14:55
Exactly. When we started, we thought, "The problem here is that people aren’t well-prepared to transition into adulthood," so we targeted schools. The first thought was to create a solution that eases that school-to-real-world transition. We built a product, essentially a 36-module animated course that covered renters insurance, student debt, investing, taxes, credit, and other topics. It was like the class you should have taken but weren’t required to, and we sold it to universities across the country. The business grew with a licensing model—going school by school—but when COVID hit in 2020, the way students and schools interacted with content changed. We stepped back to see if this model was the best fit and if we were making the impact we wanted. After analyzing the data and how people engaged with the product, we saw the need for a direct-to-consumer solution, one that went beyond passive education to help users take action. So we pivoted to B2C, and now we focus mainly on consumer needs. We still do some B2B work, but our main focus is helping consumers take real action on adulting tasks.

Callan Harrington 16:20
Were you staffed for B2B at the time, and did you have to reorg for the shift to B2C?

Genevieve Bellaire 16:25
Fortunately, we were lean enough then that it didn’t require a big restructure. I was doing most of the sales myself, and we just had to adjust our mindset and budgets to prioritize marketing. We hadn’t needed a customer acquisition budget for B2B, so it was a learning curve to shift our focus.

Callan Harrington 16:50
What was the biggest challenge you faced in making that pivot?

Genevieve Bellaire 16:55
When something is working, even just okay, it’s hard to say, "Let’s stop and try something else." That’s what we had to do, and it’s always tough because pivoting involves rethinking everything, from budgets to marketing strategies. The biggest challenge was learning how to market, build a brand, and directly connect with consumers. But the benefit was a more direct relationship with our users. We could see in real-time if they liked the product, if they were sticking around, and how they were using it. That speed and feedback loop made it easier to iterate and build something impactful.

Callan Harrington 17:40
That speed and iteration make so much sense. In terms of marketing, where did you start seeing real traction?

Genevieve Bellaire 17:45
Instagram was our strongest initial channel for organic social engagement. We’ve experimented with different approaches, from humorous adulting content to more aspirational messaging. We found that showing people a picture of "future you" with Realworld really resonates—imagining a version of themselves that’s organized, confident, and knowledgeable. That’s been powerful. We also experimented with brand partnerships and other channels, like working with employers. But one thing that’s been consistent is that when we tell people what we do, they often say, "I need that," or, "I wish I had that when I was younger," so it resonates quickly.

Callan Harrington 18:30
I found it fascinating in my research that you have no competitors in this space. That sounds great, but also challenging. How has that impacted your journey?

Genevieve Bellaire 18:40
It’s true; there’s really no direct competitor. And it’s been both a blessing and a challenge. One challenge is that when you’re building something entirely new, there’s no playbook. We had to figure out every part of the business from scratch—whether it’s go-to-market strategy, business model, product design, or storytelling. Another challenge is that people don’t Google "help with adulthood," so we had to find users when they were searching for something specific like "credit cards" or "renters insurance" and introduce them to our broader solution. And when it comes to raising investment, many investors are thesis-driven and look for categories, so it was hard to find investors who saw the vision of creating a new category with Realworld. But we were fortunate to find great people who believed in us.

Callan Harrington 19:45
How did you find those kinds of investors who were willing to bet on a new category?

Genevieve Bellaire 19:50
A lot of conversations, honestly. One of the best ways to find people is through your founder friends and their networks. They’ve already worked with investors and can share insights into how supportive they are and what their investment style is like. I also consume a lot of content around startups, tech, and VC, so you start to see who the players are and what they care about. That’s how you find the right people.

Callan Harrington 20:25
You mentioned the importance of building a community around you. Was that mainly through Techstars or other programs?

Genevieve Bellaire 20:30
Yes, Techstars was huge early on. We had a cohort of 10 companies, so you get really close with those founders, and there’s a broader Techstars network you can turn to. Alumni networks from Princeton and Georgetown were also valuable, and then just going to as many events as possible helped me meet interesting people who introduced me to others. It grew organically from there.

Callan Harrington 21:00
There aren’t many people who go through the unique experience of founding, so you find instant connections with those who have. You’re now closing in on another big shift in Realworld, which seems more like an enhancement than a pivot. How are you approaching this shift differently?

Genevieve Bellaire 21:15
Yes, this shift is exciting. Our mission has always been to simplify adulthood, but we’re now taking the next step to automate it. Over the last few years, we’ve helped people understand the basics and get organized, but our vision has been to take things off their plates entirely. With advancements in AI, we can make that vision a reality. We’re launching a next-generation product that uses AI to automate parts of adulthood, such as managing finances, tracking health insurance details, and more. Users will have a central dashboard where everything—health insurance, TSA PreCheck, frequent flyer numbers, renters insurance—lives.