[00:00:27] Jay: Hi, everyone. Welcome to the First Customer Podcast. My name is Jay Aigner. Today I'm lucky enough to be joined by Deanna Sheward. Did I get it?

[00:00:35] Deanna: You got it.

[00:00:36] Jay: Ah, two for two today. I love it. co founder, chief product officer of Capablanca. I know your husband, who was also on the show, a fantastic human being, like we were talking about before the show, but today is all about you.

And I want to hear your side of the story. I want to hear. 1st of all, where you grew up and did that have any impact on you being an entrepreneur later in life?

[00:01:00] Deanna: Sure. so I grew up in Toronto, Canada, and, you know, I think what really defined my early life before heading off to college was I had a deep passion for travel and art and architecture that was really, initiated by a trip to Scotland as a teen to kind of explore castles. And so that was the beginning of a fascination with art and architecture and it took me through undergraduate and graduate school and even a postdoc and I worked in the field and what I realized was, I just love research.

I love learning new things and diving into all new subject matter. So it was a few years into teaching that I said, well, I know these things called startups and I hear people doing great things in those, in that world. So what if I took my skills to tech? and so made the leap, over into, you know, tech companies and was focused on, you know, Growth and marketing, having kind of marketed myself as a researcher and as a, writer.

And I did that for a while and moved through different roles and realized what I also like about it is the kind of entrepreneurial side of these early stage companies that I was working for. So. I, that's really how I ended up as a co founder where I'm at today, but it was a kind of, you know, a journey with a few different threads, but at the heart of it was this.

Deep intellectual curiosity to, to jump into new domains. and I think that's, you know, what has really brought me to, be a co founder of a cybersecurity company.

[00:02:41] Jay: Was the transition like, how did you make a transition from architecture and art, you know, over to entrepreneurialism? And what about entrepreneurialism really kind of excited you and still excites you?

[00:02:56] Deanna: Yeah. So it, it doesn't sound like the most natural transition, but when you are, a researcher and a writer and a public speaker, and you're doing everything for yourself. So you're raising your own money. You're, scheduling your own events. You're your own project manager. you're doing it all right.

and so those skills are very transferable to a, to any type of entrepreneurial role. And so I had honed those skills over time and realized that I could use them in a different way. so it really actually ended up being quite a seamless, transition. I think the part that probably what took the most effort was, Building a whole new network.

I had built a network over a decade in one sphere and that network didn't necessarily parlay to the world of technology. So I think that took a bit of time, but the skills themselves, and identifying, Hey, I'm pretty good at a few things, or I could take these few things that I'm decent at and make them better in this new vein.

You know, that's what I did, and it seemed to work well.

[00:04:01] Jay: It makes a lot of sense when you put it like that.I think there's a lot of careers that you wouldn't really think lend themselves to entrepreneurialism that do kind of like you just said, like I talked to a film producer friend of mine and like, I didn't realize they were, you know, there's not like this, It's like, you could just get hired and you're just like a producer.

They're literally like free agents. They're like freelancers and they have to do all the same stuff. You did pitching and budgeting and like, all that lends itself very well. So, that matches up very well with kind of. What I've come to expect as people making the transition, and it's not as crazy, but I am very interested to hear how do you start a network over? How do you go from 0 to 1 in a space that you know nothing about? You probably don't know a ton of people.

and you've got this just. Wealth of other network that you almost have to not ignore, but maybe explore in a different way. So, how did you go about building a network in a completely different space?

[00:04:58] Deanna: sure. So there were a few people from the academic world who had spouses or friends who were doing things that I thought were related to what I wanted to do. So there were a few connections like that, which were pretty integral and kind of just learning the ropes and figuring out things. Who I should be talking to, where I should be going, that kind of stuff.

I was fortunate because it was a really boom moment for startups and just for building talent pipelines to. You know, to fuel these startups. so it was a really rich moment of that. And there were so many different events and courses and you name it. it was going on all the time. And I was fortunate to be in, at that time I was in Syracuse, New York teaching, and it was very easy to get over to New York city and then eventually move there.

And that was a hub for everything that I was thinking about. So I was. Really just going to meetups and conferences and events and telling people, Hey, this is what I do. I'm in technology. I work in the growth and marketing side of things. And eventually people, I mean, they buy your narrative cause you're saying it.

They don't quite know what you've done and haven't done unless they look. You know, deep into your background, which most people don't. So you just tell your story and your story is interesting to some, and that leads to more conversations. And I think, you know, that was really the basis of how I built the network.

I just went into it saying I was doing this new thing. found like minded people and it took off from there

[00:06:36] Jay: What made you, or how did you know that a network was something you needed?

[00:06:44] Deanna: because it was essential to what I had done before. so, you know, within the world of academia, there, there's the stuff that you will do. That's part of your curriculum. You'll take courses and you'll satisfy certain testing requirements. And then there's everything else that you can do to enhance your profile and to be seen as top of your game, top in your field.

And all of those things were very entrepreneurial in nature. You had to, you know, vie for yourself, push for yourself, apply for grants and talks and things that were competitive. And so that was already something that was in, you know, something that I had really understood,and was able to take forward with me.

Yeah,

[00:07:33] Jay: story, honestly. it's a big, I mean, you hear so many people stuck in a place where they don't want to be, and they don't know how to, it's just such a, you did it in such a matter of fact, Way that I feel like if more people had that mindset, there would be way more. Entrepreneurs right and it feels like there's like, the ones that try it and then there's the ones that want to that don't and I've always. Found it interesting, like, how you get from 1 to the other, but it doesn't. Feel like it was much of a leap for you and I think there's something to be said just about you personally. yeah, Kind of seeking this challenges and trying to better yourself and do these different things. It's a very cool. kind of transition, so tell me about cabablanca, working with your husband. which I'm sure my wife recently started a business and I have learned very quickly to not give unsolicited advice. but I would love to hear, how you guys started the company and just, you know, 1st and foremost, what it's like. Positive and negative, of working with your husband, somebody you've seen more than you see anybody else on earth.

[00:08:42] Deanna: that's right. Okay. Well, it all began because, well, let me go a little further back. I was doing growth consulting alongside working as a chief marketing officer for a blockchain company. So I had my kind of nine to five gig, but I had also been consulting over the years and was keeping some of that going.

So there was that small business on the side and at the same time, Louise, my husband was. Doing some security consulting work for a few clients here and there. Well, he also had a full time gig and he was noticing in the work that he was doing, that there was just a lot more that he could be jumping on.

Could he could be getting into if he. Could free up some time and if he could bring on potentially a partner to help, you know, amplify the business and take on new clients. And so we were thinking, you know, am I going to can expand my growth consulting work? Am I going to come over and work on product and growth with him?

We were kind of going back and forth on that. And I think ultimately how we decided that I'd come on and we would build this as a business, was because. I had recently had my son Lorenzo and I was looking for more flexibility in my schedule. I'm not saying that there's a lot of free time in an entrepreneurial, you know, when you're an entrepreneur, but what there is the ability to kind of pick and choose when you need to be places and when you can be home a little more.

Then if you know, are going to the office, so that really was a huge driving factor for me because we wanted to have Lorenzo, you know, with us at the very beginning in the home with us and we wanted to be with him and we wanted to be able to have that time and. I just felt like this was probably the right setup for us and it has proven to be, but it has had its challenges as you pointed to, you know, the highs and the lows, the good and the bad.

So I, I joined as, Co founder, chief product officer to bring my skills in product growth and marketing that I had honed over the years to Capablanca, Luis's, the more technical side of our operation. And I jumped into it, you know, never having worked in security, but having worked in privacy and blockchain.

So. Sort of knowing adjacent worlds. and I jumped into it saying, Hey, this is like the new research project for me. I need to become an expert on this and I'm going to help build this business. And,that's what we've been doing and it's been good. We see a lot of each other, as you said. and that can be difficult.

There's, you know, not a ton of physical distance that we can get between each other in a given day when we're working together on things, but it's also. Has provided a level of synergy that we. You know, wouldn't have otherwise. And I will say we both came out of the academic world. We worked under the same research advisor.

So we had done a lot together earlier in our careers as well. And we were used to that kind of relationship

[00:11:46] Jay: love that. It makes me wonder if my wife and I could survive being around each other more than I mean, I work from home and she's home too. So, I mean, it's similar. We see each other a lot, but, I could definitely see where, like, at some point, you're like, I just need to not be in this room right this second and go do something else for just a little bit.

you know, as much as I love her to death, I feel like I could see that,

[00:12:12] Deanna: and I'm in a co working space right now. So I hear you.

[00:12:16] Jay: where did the name come from? Capablanca.

[00:12:18] Deanna: Yeah. It's a reference to a famous chess player and it's Louise's. So I can't take any credit for it, but that's where the name comes from.

[00:12:27] Jay: Okay. I can't remember if we talked about that on the show. I feel like I knew that maybe, but anyway. so, who was your first customer? at Capablanca.

[00:12:37] Deanna: Yeah. So, we had a few customers before I kind of formally came on board, so I won't speak to those. And I think that's actually one of the customers that we spoke about. What I will speak to is when I came on board, who that first platform customer was. So we had a few. Some early customers that were, security, you know, we were doing security consulting for them, and then we brought on our first customer onto our platform that we had built.

and so this first customer was really important to us because they were, you know, testing things alongside us. They happened to be a, good. friend and someone from our business network who we had worked with in other capacities. So we had a lot of trust and we could, you know, also rely on them to be brutally honest, their businesses in the global, logistics and shipping space.

And they had some really pressing security needs that had to be taken care of quickly, for our new partnership. And so that's where we came in. We said, okay, tell us what needs to be done. And we. Did that for them. And well, we did that for them. We expanded our platform. So that's an approach that we've taken.

as we've developed the platform, we've kind of battle tested everything that today lives in the platform through the work that we've provided to our clients. and that has allowed us to. Use our product, the proprietary methods that we develop through our work with our clients to build that into the product.

And that allows our customers to really get a lot of value, powerful value out of the product because of the way that we're building and testing and shipping. And, that, you know, so we're so grateful to that first platform customer who's still with us today. And who's become a really important.

beta tester for us, and also they were one of our first pen testing customers. So I can't overstate the value of that type of first customer, and just how important they have been to us.

[00:14:38] Jay: Love that. what has been the biggest challenge for the business overall?

[00:14:48] Deanna: Yeah, that's a good question. I think there's a few ways you can get at that. I think one of the challenges was not jumping in. As fast as we could, we both had other things going on when we decided to kind of get into this and more so me than Luis. I was a little reluctant to, make that full transition.

And I think you know, you can do a few things and you can do those few things well, but you, it's always better when you can be really laser focused. So I think that was a challenge at the beginning. Making time for Capablanca be the most significant of the day and giving it, you know, the hours where I was the sharpest and the most able to make, you know, a real impact.

And I quickly learned that I'm going to have to drop some things and that's okay. and I'm going to have to, you know, just reprioritize what things look like. So I think that was a big challenge. And I think another challenge, and this one is probably not super unique to us, but it's an ever changing field that we're part of.

And so it's a challenge, but also an amazing thing about it that we have to be. Always on our toes, always thinking about what's next for the platform and for the business. and I think that's been a challenge, but in a really good way, it's kept us, you know, super on top of things.

[00:16:12] Jay: Now, that's a framing of that.so how has the customer changed that you go after now versus when you guys first started? Like, who is it today versus persona wise, you know, just in general, like

who are you going after now than those different or is it the exact same company in person?

[00:16:28] Deanna: No, it's definitely changed. So the, you know, the first handful of customers really came out of our previous work that we had done and the Relationships that we had built. And both of us were very deeply ensconced in early stage startups. We had worked for many, we had a lot of friends and colleagues.

Starting them, advancing them, what, you know, just a lot going on in that world. And so that was an easy network, not easy, but that was a logical network for us to tap into. And there, they were great customers and still are great customers. But we realized as we started to take on slightly different profiles of customers, that what we had built.

Really worked also for companies that were a little more advanced in terms of their company history. and that what United these bigger, more mature companies and these smaller, more agile startup teams was why they were coming to us at the time that they were coming to us. And in all cases. All of our customers were coming to us because they had an immediate need to grow, whether that was taking on, you know, a key client that they were going after for a while, or whether that was a new partnership or expanding into new markets and whatever it was for whatever type of company, they needed to up level their security.

Quickly, and they needed to expedite due diligence. And we realized that it wasn't the type of business that mattered as much as it was the business need that they had at a given moment that would make us a good choice for them and that would help us get in front of the right type of customer. So the profile, the persona of the customer has expanded quite a bit and we still definitely work with early stage startups, but we've.

Expanded out from there. And now we were really looking, you know, as we talk to potential customers, and as we have those really important conversations, we're looking for those key. Pieces that, that tell us, Hey, this is somebody who has a really pressing need and we're the right fit for them because of the nature of that need.

[00:18:48] Jay: Right. That makes sense. How much time and effort do you guys spend on partnerships and are you responsible for that? Or is that something? Louise handles.

[00:19:01] Deanna: Yeah. We spend a good deal of time on that and it's joint handled at this point. I think it'll probably live more under me longer term, but. we're doing a lot together,as we build this and as we expand this business. so it's, it really is a joint effort today. It's a big part of how we want to continue to grow.

We haven't, and this is important because this is coming from, you know, I'm a growth and marketing person. So I've spent ad dollars. I've done all the things that fall under the umbrella of. Marketing and growth and all of that, and so it would be easy to say, hey, let's turn on a channel.

Let's spend some money here. But I've also seen the downside of being reliant on those kind of, you know, Core channels that most people turn to what I've also seen in my past experiences is the power of Partnership building the power of a referral network the power of even having a referral network, you know for your customer base all of that and so we've Intentionally really spent our time there.

We haven't opened up the you know, paid advertising floodgates, so to speak. We're really working on relationship building at this point because it has worked for us so far.

[00:20:18] Jay: now, that's a, I mean, we do the same thing at our agency. Yeah, I think, and it's also important because. Your original starting network taps out faster than most people think it would.

especially if you run the business for. Yeah, multiple years, several years, then you start to go. Well, my network is great, but, everybody knows who I am and then you have to kind of turn the gears and go.

Well, now what? Right? It's like the same thing you kind of mentioned of, being very specific about not just opening up a bunch of channels, but kind of trying to pick the ones you're going to go after. And maybe it's marketing. Maybe it's. Outbound, maybe it's, you know, inbound via podcast or whatever it is. I love the intentionality of your next, you know, kind of move to bring in business. And I think relationships are, by far the easiest way to establish trust.

Right, which is like, you guys work in security. We work in testing, kind of semi related fields. And I'm not going to say you don't have to trust your development team or trust your Products team or trust or whoever, but like, there's a real. Fear associated with our specific departments in any company, because if it gets past us, then it's a real problem. Right? So there's

a higher level of trust required for entry. for a 3rd party like us into any of these places. So I love the building relationship piece there. All right. last question, non business related.

[00:21:50] Deanna: Sure.

[00:21:50] Jay: Nothing to do with capital market taken over the world and cybersecurity. if you could do anything on earth and he knew and fail. What would it be?

[00:21:59] Deanna: I thought I might get a question like 

[00:22:01] Jay: You knew you were you saw the episode. You did 1 of like 1 out of. 150 that may have known what this question was, so I would love to hear your pre. Home where you said you do a lot of homework, you'd like to research and I see why you knew this, but go for it. What's your answer

[00:22:17] Deanna: I think if I could do anything, and I knew it wouldn't fail, I would work on something to do with energy in the environment. I just, it's something that I think about on a daily basis. I've got no expertise in it. I know there, we need to solve things in that realm. I think if I could throw myself into anything and it wouldn't fail, I would throw myself into that cause.

[00:22:44] Jay: to be fair? I don't know that there was many things you could throw yourself into that. You would fail. I like your, Your approach to things, and you've been successful so far and I love talking to Louise about business and I hope to, you know, we can talk about business and what we're doing and how we're doing it because, I. I do think good people go further and you build those relationships and you have trust and it's a different type of business than just a transactional business. People are trying to grow as much as they can as quickly as possible. So, I really love you guys love the story. and I'm really thankful for you being on today.

If people. when reach out to you specifically to hear something, they talk about something they heard today.

How do they do that? 

[00:23:24] Deanna: Yeah. They can reach me at Deanna, D E A N N A at Capablanca.

[00:23:30] Jay: Got it. And cabablanca. io. to check out. You guys services and your products.

All right.

Well, I think this is my last call of the day last call of the week. So you get the happiest version of Jay all week. So thank you for your time today. I appreciate it. I hope you have a great weekend and a great 4th of July coming up and appreciate your time being on.

[00:23:52] Deanna: Thank you. You too.

[00:23:53] Jay: Awesome. Have a good day. See you 

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