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Recognizing Opportunity, with Hannah and Jade Sullivan

Recognizing Opportunity, with Hannah and Jade Sullivan

Episode 111: Recognizing Opportunity, with Hannah and Jade Sullivan

Hannah and Jade Sullivan are women founders disrupting an age-old industry. When Hannah and Jade first had the chance to start, their own insurance business, they weren’t sure it was for them. They were designers by trade and had no formal experience working in insurance. But being the go-getters that they are, Hannah and Jade recognized their fresh perspective could provide a unique opportunity to reshape the way things were done. In this episode, we talk with Hannah and Jade about what it was like to dive head-first into a new industry, as well as how they manage their relationship as both business partners and spouses.

00:12 Kristy Wallace: Hello and welcome to the Ellevate Podcast. This is your host, Kristy Wallace, with my co-host Maricella Herrera.

00:19 Maricella Herrera: Hey, Kristy.

00:20 KW: Hey, I'm always afraid I'm gonna say Kristy Cisco which is my maiden name. And sometimes I have to think back and be like, "Did I say the right name?" I've been Kristy Wallace for many years, but I always...

00:31 MH: I'm gonna say, though, you really truly love Jay 'cause Cisco's a great name.

00:35 KW: [chuckle] I know right. It is a great name and it reminds me when Zainab Salbi was on the podcast probably about a year ago, we talked a lot about changing your name and culturally why you do it and the significance and the meaning. And I didn't for a few years and then once we started having kids, I just... Was easier.

00:57 MH: Yeah, the paperwork.

00:58 KW: Yeah, paperwork.

00:58 MH: Yeah, in El Salvador you still use the "Of". You actually become...

01:03 KW: Oh, like Handmaid's Tale?

01:03 MH: Yeah.

01:04 KW: You're like "Of"

01:06 MH: Yeah, of someone else.

01:07 KW: Of Herrera?

01:09 MH: Right.

01:09 KW: Interesting.

01:10 MH: It is bad.

01:11 KW: Wow.

01:12 MH: Yeah.

01:13 KW: Well, we have talked in the past about the gender divide in El Salvador or inequalities. So I guess...

01:19 MH: Don't get me started. Need a drink for that. [chuckle]

01:24 KW: Alright.

01:27 MH: Well, so let's wrap this up.

01:27 KW: Well, not right now because it is early in the day, very too early in the day for that. But a future podcast, we're gonna get in on that. But, no, today we have a great guest, Hannah, who is entrepreneur and woman founder. And just it was a great conversation talking about the learnings of building a business and particularly doing so with your partner. So we have some great insights for there. Before we get to that though, I know we've been doing some research on money and business and the spending habits of our community. And whether you spend your money with businesses that are founded by women that align with your values or if you don't. So what does that research tell us?

02:12 MH: We've been doing a couple of polls on spending money with female-founded companies, specifically right now I know that that will continue to increase. The one I have today says, "Will knowing that a company is founded by a woman make you more likely to buy the product?" 37% said somewhat, 28% of our community said very, 18% said extremely. So that if I'm... My math at this point of the day is not as terrible, that's over 70% of people who would definitely...

02:50 KW: Yeah. To some degree of it... Yes.

02:50 MH: To some degree, yeah. Would to some degree be more likely to buy a product if the company is founded by a woman.

02:57 KW: Interesting.

02:58 MH: So that's good.

03:00 KW: Here we go. Women supporting women.

03:00 MH: Yeah.

03:01 KW: Although we want everyone supporting...

03:04 MH: Right.

03:06 KW: Women as well. But this was a poll of the Ellevate community which...

03:08 MH: But it's nice to see... I was gonna say, well, our community is biased, but it's not biased. It's great to see women supporting women. You hear so much that that's not the case. Research shows otherwise.

03:23 KW: And we have... So on this week's podcast Hannah is a founder. Next week as well, we have another woman, Sarah LaFleur, who founded MM.LaFleur, who has great insights into why she founded the company and what she's learned along the way. Sarah is also starting our series of podcast guests who will be at the Ellevate summit in June.

03:47 MH: Yep, very excited.

03:48 KW: Are you excited? How are you feeling about this, Maricella?

03:51 MH: I feel terrified, nervous, like I'm gonna have a breakdown... No, I'm kidding. I'm really, really excited. It's a lot of work, it's crazy for the next month, but it's so rewarding to see it happen and to see everyone come on board and to just... We get emails, all of us, you get emails, I get emails every single day with people who wanna participate in the summit in some way, shape or form and it's great to see because the more voices that we have talking about gender equality the more people that we have engaged in the conversation the better we can actually strive for change.

04:29 KW: Yeah, so we have Sarah who is our guest next week. Mike Steib from XO Group who's the following week. Some really phenomenal speakers that will be at the summit. We wanted to give you a sneak peek into their thoughts and ideas and the ways that they're supporting women and inspiring women in business. And really digging into many of the nuances of not just women in business, but we wanna talk about women of color, we wanna talk about men as allies, women with disabilities, women who are entrepreneurs and driving change within corporate America. There's so many ways that we can affect change and be change-makers and driving action towards equality. So check out the podcast in the next couple of weeks, you don't wanna miss them. Share them with your friends, tell us what you think about it on social media. We're on all the major social channels including EllevateNtwk on Twitter. And my final big ask, sign up for the live stream. Go to You can register now to watch the live stream the day of it's free and it's gonna be jam-packed of inspiration, phenomenal speakers and lots of fun. So no matter where you are you can join us live for the Ellevate Action Summit on June 21st.

05:47 MH: Yeah.

05:48 KW: Alright, thanks so much and let's get to the interview with Hannah.


06:02 Hannah: Hey, how are you?

06:04 KW: Good. Who else is on the phone?

06:06 Hannah: Jade. She is my wife and business partner.

06:08 KW: Hey, Jade. How's it going?

06:10 Jade: Hey. It's going great.

06:11 KW: So Hannah and Jade, welcome to the Ellevate Podcast, I'm very excited to have you here today. I wanted to get started just talking a little bit about your business. Because we love hearing new and innovative ways that companies and founders are really disrupting sort of age-old industries and you're definitely doing that. So why don't you tell us a little bit about Pogo, what it is, what you do and then how you came to the point of starting this business.

06:42 Hannah: Jade and I are both designers. We met in a graduate program called VCU Brandcenter for Innovation and Design. I was an art director and Jade studied creative technology. And so we definitely do not have long-term insurance background by any means.


07:06 Hannah: But my dad has been in insurance for over 30 years and he has a bunch of agencies and brokerages throughout Virginia and he was like, "Hey guys, do you wanna come work on this new backend insurance program I'm starting for agents." We were like, "That sounds totally un-appetizing. Oh, let me think about that." And then we were just like, "Okay, yeah, that could be a really fun challenge." We love creative problem solving and we also like to be really random so we we were like, "Okay, sure."


07:36 Hannah: So we both have experience freelancing. Jade was a freelance video editor for quite a while prior to meeting at the Brandcenter and so we started Pogo which is an online aggregator for business insurance, like Kayak. And we provide business insurance to self-employed people like freelancers, consultants, independent contractors...

08:02 Jade: Small business owners.

08:03 Hannah: Everybody, yeah.


08:06 Hannah: So we just wanna help them stay protected and keep their businesses safe.

08:10 KW: And how do you aggregate all of this information? I'm always completely amazed, yeah, when you're booking travel or when you're now even shopping on the Google interface, the aggregation tools that make it so much more transparent and easier. And I think insurance, particularly, is an industry that feels like it's not transparent. So how have you really disrupted this, have you solved that with the technology you've created?

08:39 Jade: Yeah. So basically you just come to our website and fill out one form and we compare over 30 top carriers and it's as simple as that. But I guess the relationships with the carriers and getting them on board was the main thing because that's just the hardest part.

09:01 Hannah: Yeah, we're lucky to have... Steve my dad, his relationships with all of these carriers. And so paired with our kind of forward-thinking, design-thinking and user-experience...

09:17 Jade: Yeah, just making the process as simple as possible.

09:20 KW: How much work do you think you have to do just to educate about insurance in general? Is that part of your model? And I ask that because I think so often times you don't know what you don't know, it seems confusing. What is life insurance? What's renters insurance? What do you need insurance for? And things that tend to be confusing, then oftentimes tend to be things that we don't invest in.

09:45 Hannah: Exactly, you just want to completely run away and never think about it again. Everything relies on you, if you're not getting something done, it's not getting done. So to jump into insurance, that's a completely foreign language and really hard to navigate. It's just totally up-appetizing so people just kind of shy the other way. And that's why we really feel like we can help people out because we do have that kind of inside peek on what insurance is, but also are normal people too, so we can kind of relay that to other designers and creative professionals and contractors and things like that in an easy to grasp way.

10:32 KW: You've mentioned your dad and his background in insurance in kind of giving you some of the inspiration for founding this business. How key is it for entrepreneurs and founders to have that champion, to have that person who's ingrained in an industry and to provide that sponsorship?

10:52 Hannah: I think it is 100% necessary. Well, first of all, they are so knowledgeable, they have such experience and expertise. They have resources, whether or not that's financial resources or relationships, they just help you with access to things. And then, obviously, having somebody in your corner really just helps you... To your self-esteem and your mood. I mean, there have been so many times where Jade and I have just been like, "Oh my gosh, this is so much to figure out. How can we ever do it? How can we tackle it on?" It's nice to just have somebody pumping you up and believing in you.

11:33 Jade: Yeah. And just having somebody with so much expertise and then pairing that with sort of a fresh perspective, it's a really good juxtaposition.

11:41 KW: What's been your biggest challenge starting the business?

11:45 Hannah: I would say our biggest challenge is just kind of psyching ourselves out. Jade and I are big time over-thinkers and over-achievers and over-analyzers and we just like to outdo ourselves all the time. So just...

12:02 Jade: Relaxing and just being like, "Nothing's ever gonna be perfect." You just have to do the best you can and keep moving forward with each part of the process.

12:12 Hannah: Yeah, I think a big part of why it's so hard starting something new is because you're not perfect at it because you've never done it so how could you be.

12:21 Jade: Yeah.

12:22 Hannah: So it's just learning to kinda go with the flow and be okay with the process.

12:26 Jade: Be okay with learning about every single thing you're doing. [chuckle]

12:31 KW: You mentioned both of you have more of the design background. So what are the ways in which you are leveraging others with different skillsets, backgrounds and experiences as you build the business? So if it's legal or financial or the competencies that maybe are in your wheel house?

12:51 Jade: Yeah. So luckily, that whole package came with Hannah's dad, Steve. [chuckle] We have all of his back office agents and experts. So every part of that is taking care of all of the agency management systems, legal team...

13:07 Hannah: Licensing.

13:08 Jade: Licensing. Literally we just sort of plugged in. But, yeah, that's a big part of everything.

13:16 KW: That's good.

13:17 Jade: Go and do a family business.


13:18 Hannah: Yeah. And just really do it all. [laughter]

13:19 Jade: Exactly.

13:21 KW: That's amazing, who's your...

13:23 Jade: Yeah, we got lucky.

13:24 KW: Who's your core customer?

13:26 Hannah: Originally, when we made Pogo, we were like, "The primary people that are gonna be coming to us are creative professionals. Like IT consultants and writers and photographers." And we have gotten a mix of that for sure, but surprisingly we have had a lot of independent contractors like handyman and plumbers.

13:47 Jade: Landscapers.

13:50 Hannah: Carpenters, it's been a really nice mix.

13:53 Jade: Yeah. It's really cool.

13:54 Hannah: Yeah. And I think a large part of the reason why so many independent contractors come to us is often times they are required by contract to carry their own insurance, especially when it comes to workers comp.

14:09 KW: How do your customers find you? I think that's always one of the biggest unknowns or challenges for a startup, is you identify your customer, oftentimes that evolves and changes as your business launches, but how do you get the customer in the door in the first place?

14:26 Jade: Yeah, that is probably the biggest part right now and that is, I'm sure, everyone's biggest challenge after they've launched, after they've spent so much time on creating the product and the interface and all that and that's something we're learning every single day. And we're experimenting, we're trying new things. But I would say a big part of it is just getting in touch with small business experts who already are giving advice and we are partnering with them or offering to be a resource and just really trying to help people and be a thought leader on the internet. That's our main, main focus.

15:08 Hannah: Yeah, we're just trying to be as available as possible.

15:11 Jade: Yeah. We wanna be the ones that people go to when they have questions about insurance.

15:16 KW: Well, I think that's such an important point because positioning yourself as a thought leader is a great way to build credibility for your business, to build a brand for yourself, but it's... I don't wanna say it's an inexpensive way to drive brand awareness because it's a lot of time and effort and energy on your part...

15:36 Jade: For sure.

15:37 Hannah: Yeah.

15:37 KW: And time is money. But it's a way to really have not such a financial output in building your brand. So what are some of the... Let's dig into that deeper, what are some of the ways you're really building your thought leadership? Is it speaking, is it writing? And then how do you go about doing that?

15:57 Hannah: Well, we are a local business, but we can write nationally. So we're kind of dabbling in the local community as well as across the country. We just recently spoke at one of the 1 million Cup events in Richmond. It's for local entrepreneurs and it's just a way to promote small business and we thought it would be great to kind of tell everybody our story and offer ourselves as a resource to other startups and stuff in the community. So we've definitely been interested in connecting more with people in Richmond and in Virginia and aside from that, like Jade said, just going to organizations and sites and resources revolving around entrepreneurship and being a startup and being a woman in business or whatever. Just kind of saying, "Here's our take on things and... " And that's... We're about insurance, but also just being a business person and being like, "Hey... "

16:57 Jade: Definitely.

17:00 Hannah: There's a funny take on it, hope you think it's funny.


17:03 Jade: And just joining certain organizations and contributing as writers. Hannah's been really big into writing and so have I. I joined the Forbes Finance Council and I'm contributing to their website now, just things like that where we can just get our message out and get the word out and just help people understand what they need and why they need it and really just be there when they're asking questions.

17:25 KW: So starting a company can be very difficult and part of what makes it difficult is the founders, right. And how you work together and how you deal with stress and you learn so much about relationships during that time, but your relationship actually, Hannah and Jade, is a little bit more complex than that because it's also of a personal nature as well. Can you share a little bit more about how you work together and the pros and cons of that.

17:52 Hannah: Yeah. So Jade and I met in a class that was for art directors and writers and Jade was a creative technologist and she was auditing the class and on one of the first projects she came out to me and asked if she could "join my team."


18:10 Hannah: And from there we pretty much never stopped working together. We would try and get on each other's teams and projects as often as we could and we obviously connected creatively and then things progressed and we got together and moved to New York together and worked as a non-traditional team up there at a creative agency. And then now we work together as a married couple. And it's really fun and we don't know any differently because we've always worked together. That has always been part of our relationship, but it's pretty fun. And it's also fun too 'cause we work with my dad. So it's like, one big happy family.


18:53 Jade: And obviously there are challenges as with every relationship, but you just... The important part is just growing and learning and being receptive to how others are and how... Just being good at relationships, I guess. [chuckle]

19:08 Hannah: Yeah. And if one of us is being annoying we have no problem with being honest.

19:12 Jade: Yeah.


19:15 KW: Is it hard to separate work from home?

19:19 Hannah: Well, it can be, yeah. Especially if... If we're both stressed, it's kind of like, "Okay, we're in it together," but if one person is stressed and one person's not, it's kind of like...

19:29 Jade: Then it's annoying. [chuckle]

19:29 Hannah: "Okay, you're killing my vibe. Let me be over here." But that's why we created a code word which is, ketchup. And if one of us says ketchup then it's like, "Okay... "

19:39 Jade: "No more talking about work for a couple of hours or for the rest of the night." And if it's something really important and you just... You need to override ketchup for a minute then you have to say mustard...

19:48 Hannah: And that's for a minute.

[overlapping conversation]

19:50 Jade: And I reframe really fast, but we're not gonna talk about it for an hour. It's just gonna be really fast and then it's over.

19:55 Hannah: And then it goes back to ketchup.

19:56 Jade: And that really, really helps.

19:57 Hannah: It does. [chuckle]

20:00 KW: I love that. It's so important to find the techniques and tips for how to navigate these situations and sometimes, I don't think we're often good at that, right. It's rather suffer than try to overcome. So that's really great advice and something I'll probably have to... I worked with my husband for a very brief stint and it didn't go well. And we have both decided that will never happen again. So I'm completely in awe of you.

20:26 Hannah: Yeah, that's normal, I would say.

20:29 KW: So what are some of the other things you do to stay balanced? How do you... As a startup founder can really take over your life. So how do you ensure you get some me-time in there?

20:38 Jade: Well, honestly, I don't know how conventional this is, although I think it's becoming more and more common, but something we do since we work all the time, basically, we found that co-working in other places is something that really makes it more fun to be at work. [chuckle] So we've worked from Mexico City, from Buenos Aires, from [21:00] ____. And we'll just go for a couple of weeks or a month and you're in a new space, you have new places to go for lunch, you have new markets to see on the weekend and it's really... That's been really cool for us.

21:15 Hannah: Yeah, it's really inspiring and it actually increases our productivity because we're not... There's just less distractions at the office itself. And then coupled with taking new routes to work or going shopping new places, it's just... I don't know, it just makes you feel really inspired and creative. So you can just go longer.

21:36 Jade: Yeah. And one of our... Because one of our professors once said, "If you're not putting anything in, you can't put anything out." The point is that you need to stay inspired however you can to be able to still think creatively and creatively solve problems and all of that.

21:53 Hannah: Do good work.

21:54 Jade: Yeah, to do good work. So we really just try to follow that rule the best we can with the time we can.

22:01 KW: You're my female role models. Oftentimes you feel like it's unattainable. So the fact that you've really figured that out is truly inspiring.

22:11 Hannah: Yeah, it's called Airbnb your own house.

22:13 Jade: Yeah, it's basically like trading spaces. And with the internet you can work from anywhere. So you just have to be willing to figure it out.

22:21 Hannah: And with that we've tried to stick mostly in the time zone that's been really helpful.

22:27 Jade: Yeah, that's the main thing.

22:28 Hannah: For meetings and stuff.

22:29 KW: Awesome. Well, Hannah and Jade, thanks so much for joining us today on the Ellevate Podcast. It's been really great to learn more about Pogo. If our listeners are interested in checking it out, where should they go?

22:42 Hannah: You guys should hit up

22:46 KW: Cool. Awesome, well, thanks so much. Where are you right now?

22:51 Hannah: We are in Richmond. We are at the office.


22:56 KW: Okay.

22:58 Jade: Headquarters.

22:58 KW: So not somewhere nice and warm?

23:00 Hannah: No, a couple of weeks ago, but now we're here pretty much in the snow. [chuckle]

23:05 KW: Alright, well, thanks again and it was great chatting with you.

23:08 Hannah: Thanks, thanks for having us.


23:13 KW: Thanks so much for listening to Ellevate. If you like what you hear, help a girl out, subscribe to the Ellevate Podcast on iTunes, give us five stars and share your review. Also don't forget to follow us on Twitter at EllevateNtwk. That's Ellevate Network. And become a member. You can learn all about membership and all of the great things that Ellevate Network is doing at our website That's ELLEVATE And special thanks to our producer, Katharine Heller, she rocks. And to our voice over artist, Rachel Griesinger. Thanks so much and join us next week.


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