03: Impress the Sharks and take down Industry Giants with Fintech Founder, Cody Barbo

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In this episode, Dan sits down with the founder and CEO of Trust & Will, Cody Barbo. Trust & Will is a series A stage company that currently serves over 150,000 families in one of the most essential and yet underserved markets. Trust & Will helps individuals and families by making estate planning simple, accessible, and affordable.

From being elected Student Body President at San Diego State University to impressing Shark Tank investor Mark Cuban at a pitch event, Cody has made the most of unique opportunities to develop and showcase his entrepreneurial skills. He’s put those skills to good use in founding an already successful estate planning fintech that has taken on industry incumbents and is set to explode. Join us as we trace Cody’s journey and learn how he saw the vision, secured investors, and successfully launched Trust & Will. 

  • Cody shares how his unique leadership opportunities as a college student at San Diego State University helped shape his entrepreneurial drive and skills (2:00)
  • Finding his “Niche”: Cody shares the valuable business lessons he learned with his first tech startup (4:50)
  • Making the Pitch. Cody talks about how he developed his ability to make great pitches and how he met Mark Cuban, made connections with future partners, and even made good startup money doing it! (8:00)
  • Cody offers a great piece of advice on the importance of valuing connections with people and making tools like business cards and LinkedIn work for you (12:45)
  • Here’s a Pro tip on fundraising from a guy who’s raised 8 million in capital (17:33)
  • Cody shares how he found the business vision he was willing to risk it all for? (18:38)
    • Dan and Cody talk about the intimate subject of estate planning and the brilliance of Trust & Will that makes this essential service simple and accessible. (23:28)
  • Dan asks Cody how he was able to convince investors and customers that his company would handily outperform household names in this industry. (26:43)
  • How Trust & Will prioritized customer experience while working to find and establish price points. (33:09)
  • Dan asks Cody to share his secret weapons for success (38:33)

These are great insights from a great entrepreneur. Thanks for sharing with us, Cody!

Product Market Misfits is a weekly podcast that helps entrepreneurs learn more about starting companies and getting funded by sharing conversations with world-class venture-backed founders who are one or two steps ahead of you on the path to success. For more, visit us at www.ProductMarketMisfits.com 


Dan Hightower: [00:00:00] This is Dan Hightower with Product Market Misfits talking about one of my favorite industries, FinTech, and an amazing company in this space founded by Cody Barbo, Trust & Will. Which you can find at trustandwill.com. Trust & Will makes estate planning simple, affordable, and accessible so you can live comfortably knowing your affairs are in order in case something happens.

I’m extremely excited to welcome Cody to Product Market Misfits today. For those who don’t know Trust & Will is a series A stage company having raised 8 million from some amazing investors, such as Luma Launch, Halogen Ventures, Link Ventures, and Tech Stars. Also, I’d like to thank Leront from Luma Launch for the question suggestions.

And for all those podcasts with a little too much noise and not enough signal, I recommend pod shots. It’s spark notes for podcasts. They tweaked the top ideas from amazing podcasts and sent a digestible newsletter. So it’s as if I listen to all my favorite podcasts in just a few minutes. As the saying goes, most books should be a blog post and most blog posts should be a tweet. And now most podcasts should be a pod shot. Check them out today on Twitter @_podshots and subscribe to their newsletter at substack.podshots.com. So Cody, how’s it going, man?

Cody Barbo: [00:01:19] Hey Dan, thanks for having me.

Dan Hightower: [00:01:21] Yeah, the day I first heard your name was three or four years ago, when our mutual friend Daniel Goldstein was like, Hey, would you like to make an investment in a new FinTech company? And I was like, sure. So, I mean, we’ve, I’ve followed the journey.

Cody Barbo: [00:01:42] Yeah. You’re part of the Journey

Dan Hightower: [00:01:44] A pleasure, a real joy to watch you work and watch you grow this company. And for that reason, I am incredibly excited to, you know, peel the layers back and dive in. So as an opener, I love to break the ice

First, I’d love to just hear how you got to where you are today. A multi founder of like three startups. How do you think about your journey there? And then what has been the biggest mistake or two that you’ve made along the way there?

Cody Barbo: [00:02:20] Yeah. Yeah. Happy to unpack it. So, born and raised in Southern California. So I’ve been here 31 years. I started the first half of my life in Huntington beach. So I was a longhaired surfer growing up, which most people wouldn’t assume seeing me now, but you know, that was my lifestyle back then. And I loved growing up in that area. Close friends and family still there. And I made my way down to San Diego in 2007 to go to school at San Diego State University.

Yeah. My time at SDSU was pretty unique. I mean, I was obviously excited for college. I think anybody is. But I was working at the Apple store. That was the first year that the first iPhone came out. So I always had kind of this passion for tech. I was kind of a geek at heart, but my time on campus, I really grew out of my shell as I was kind of your introverted quiet kid and started getting involved in leadership roles, whether that was student government, my fraternity, other student organizations on campus.

And the reason why I’m sharing this is that by the time I was a senior, I was student body president. And the unique factor about this role is that I served as chief executive officer of associated students for the full year, which is a $30 million umbrella organization to the university. You have 80 full-time employees. A thousand, part-time. We manage and operate seven on and off-campus facilities. And the big project from that year was building the new hundred million dollar Aztec student union, which is one of the most sustainable buildings in the country. It’s double LEED, platinum-certified for sustainability components, and being really involved in that project along with many other student leaders and campus leaders kind of like rewired my brain and never having that level, a little responsibility, being able to set such a large vision to impact such a large organization, but also knowing that I had to replace myself in the next year. It’s only a one year term. And seeing one of my execs take on the role of president the next year was really fulfilling. And the reason why I bring this part up is that I think it is the catalyst to why I became an entrepreneur and I didn’t go and pursue a job at a big corporation or become a doctor like I think my parents wanted me to become. And it just rewired my brain to have this mindset. It’s like set a vision, get the right people on board, and be relentless about your ability to execute.

Now, I had four years prior to this role to learn the organization, to learn from mentors. So it wasn’t, I just stepped into it on day one. I still had a lot to learn as I went through it and had a lot of reflections as I moved on a year out. But instead of going down this path and going to work for a big company, I went headfirst into entrepreneurship and started my first company right out of school. It was called Niche or Niche. However you want to pronounce it. I have some lessons that I’ll share about this one, but effectively. The super quick pitch of Niche was that it was like Pokemon Go for video content before Pokemon Go existed. But the concept was you go to these places, whether it was the bar down the street Coachella, you have your friend’s house. You’d go party out on the weekends.

I was 22 and you didn’t want all these photos ended up on Facebook, which is about the same time that Facebook had opened up their platform to our parents, family, friends. So, you know, I didn’t want them to think, and that’s all I was doing. I was still a responsible young man. So we created this kind of geo-fence around places.

You could draw on a map, a geofence. And when you walked into it, or if you allowed your friends through your contact list to walk through that, geo-fence, that’s what unlocked the content. So if they missed the party the night before, and they were at the house the next day because they’re physically present, they could see the content, but if they never made it to that physical location, they’d never be able to see the content, thus the Pokemon go for videos and photos.

So that’s the concept that hopefully for listeners, it’s easy to digest what the Pokemon go reference. But you know, it took us a year and a half to really make any progress or traction. It was really hard to raise fundraising at the time. I didn’t know how to run a funnel, how to run a process, how to pitch angel investors.

I really didn’t have that mentor network of entrepreneurs, the way that I had a mentor network of student leaders back on campus. And instead of trying to figure it out all myself, I went out and recruited like six people with MBAs on their resume, which is also not something I recommend doing. There’s a lot of good MBAs out there. I’m not trying to discount it, but like just recruiting people for the sake of MBAs to fill like a finance role, chief marketing officer role, you’re not pulling out of a C suite when you are really just there for one reason. To get a product to market. Don’t even worry about everything else and test it. If it works, it’s sticky, you can drive revenue or drive growth, then build a business around it. But we tried to just build the business without any substance at its core, which has no real product, no real customers, no revenue. And I think that in hindsight, that’s why we never raised capital. Ended up disbanding. Dissolving the company in 2014. So it was a fun ride. That was a year and a half of time and savings, but those are the quick lessons on Niche.

Dan Hightower: [00:07:13] Yeah. So I have a product that’s yeah.

Cody Barbo: [00:07:16] Or at least have a case study as to why you’re solving a problem. Or at least people to take a bet on you. The other big life lesson about Niche that I recommend is, make sure you look up that there’s not a lot of other companies in your space with the same name. So Nice. N-I-C-H-E, however you want to pronounce it. There was one that was acquired by Twitter for like $30 million in 2013, 2014.  And my LinkedIn blew up that day because it was obviously not the same “Niche”. It was like an influencer marketing platform. One of the first that ever existed. And sometimes when a company has the same name as you and you don’t have the trademark, you don’t have the .com. You don’t have that web authority, that domain authority, you don’t have anything. So not even a brand.

Dan Hightower: [00:07:59] I’ve had the pleasure of watching you pitch live so many times. How do you, how did you get good at that? Live pitching. And, you know, would you have any recommendations?

Cody Barbo: [00:08:10] So I’ll kind of bring it back to the story too. So industry, my second company, I had done a small stint in the restaurant industry. I was, you know, trying to work the tip money and so to say. And, engaging with such a diverse audience and people coming into the restaurant and just people, all different types of backgrounds. And then I complimented that with my undergraduate leadership roles.

I mean, when I was student body president, I was speaking in front of student groups, as small as 30 and as groups as big as 13,000 people at convocation. And you have to learn to cater your speech to the time that’s allotted, the audience that you’re talking to. You talk a little bit faster, a little more casual, a little bit slower, a little more professional cordial.

So I’d taken kind of a little bit of the student leadership days, the hybrid of the restaurant industry experience. And then injected that into Industry, my second company. And the reason why I’m transitioning back to the story is that we did a lot of pitch competitions at that company.

There’s endless startup pitch competitions. Some there’s no prize money. There’s no product. It’s just feedback from the local startup community. Some startups have prize packages worth tens or hundreds of thousands of dollars. And then some of them I’ve seen that there’s this one in I think it’s Syracuse, New York and there’s some global startup pitch competition. There’s like a million dollars cash, not even just investment, up for grabs. So if it is the right, like “We work”. “We work” does a million-dollar grand prize, Syracuse, the city of commerce for, I think it’s Syracuse or Buffalo. One of the two, I think it might be Buffalo actually. They have these huge prize packages. They want you to relocate to Buffalo New York. But it’s the real deal. And if you’re not mindful, and you don’t care where geography is. You can build a great company anywhere. That’s pretty serious incentive to want to sign up with these pitch competitions. And we’ve done it with Trust & Will too. But the reason why I use Industry is that we had a couple that were really killer.

One is it was the industry we were in was hospitality, but really we’re an HR tech platform. We had done this accelerator multi-day conference up in the Bay area and we entered a pitch competition and there’s a hundred thousand dollars up for grabs and we won and it was hype. We got one of those big Happy Gilmore, golf check. Got the photo. Got to post it on social and got to pop champagne.

We also did a big pitch event up in Los Angeles at this event called Vader Splash LA, where Mark Cuban was one of the judges. So like not shark tank, but literally the shark tank guy. And I had a photo with Mark Cuban. When I was 15 years old, it was Clippers Mavericks in Los Angeles at the Staples Center. And I showed Mark the photo before we went on stage, which was probably not the wisest.

Dan Hightower: [00:10:49] You didn’t put it in the pitch deck?

Cody Barbo: [00:10:51] No, I should. I didn’t know. I didn’t know he was going to stay back. So we won that pitch event. So I think it was like 25,000 in prize packages, which included like a private plane flight, which was the most random but cool prize package ever. No purpose to the company. It was just kind of an ego flex. But Mark Cuban! Winning that pitch competition with Mark Cuban and still having the second photo now and the history and the journey was super cool. And whenever I have these pitch events, there’s probably a half dozen bigger ones that we won in the first two, three years of, of Industry is, you know, driving up from San Diego to LA or flying up to the Bay area, knowing exactly how much time it was allotted, getting to the venue beforehand, looking at how the stage setup was. How I can pace myself across the stage, make good eye contact, almost as much of an investment in the nonverbal piece of the pitch itself. As in the verbal, along with what’s on the screen, coming from the pitch deck and knowing the audience too. Is it going to be a small audience or a big audience? Who’s voting? Is it the judges or is it the audience sort of open internet? Sometimes they do it through Twitter. If people are tuning in live. Yeah, and that’s, that’s kind of the equivalent now with virtual pitch competitions that are still going on because it will be virtual audience, but knowing who, how many people, et cetera, and trying to always cater their pitch towards that group.

And with Industry, we did all these pitch events and it didn’t materialize to too much. I mean, the prize money is helpful for a lot of startups in the early days or the services. The prize packages. Sometimes it’s like an AWS credit or, you know, coworking space for three months, blah, blah, blah. But it does help because in the early days, like if you don’t have the capital, if you don’t have the resources, those little prizes add up and you can get you one month, two months further out or give you a space, that’s not the living room where you have roommates or family at home.

So I’m happy that we participated in some of them. And that’s why my long answer to your question. 

Dan Hightower: [00:12:43] It’s a good segue because, for you, it meant a lot more down the road. I connected with Leront Grill at Luma Launch, and he told me the story of how you met. You met while you were pitching Industry on stage.

Cody Barbo: [00:13:00] Yeah.

Dan Hightower: [00:13:01] So he was like, yeah, I didn’t really love industry the idea, but I loved Cody as a founder. So I approached him afterwards because I wanted to meet Cody, which is great because you got one of the two founders,

Cody Barbo: [00:13:15] Right

Dan Hightower: [00:13:15] So you guys talked, you took his business card and put it in your pocket. And then five years later closed Luma as an investor interest in Trust & Will. Which is like some serious Rolodex management.

Cody Barbo: [00:13:29] Yeah. So Leront, you met him virtually. I’m  6’4″. Leront is 6’8″. So like he literally is the tallest person you’ll see at almost every startup event, unless it’s like some of the golden state warriors who are now VC’s.  it’s like, he’s the tallest guy ever you can’t miss that. But there’s perks of being the tallest guy at every event is that you just kind of naturally spark up a conversation with people. And we did, it was either Silicon beach Fest in Marina Del Rey, or it was another LA, it was the LA Venture Summit, maybe at the Fairmont, I’m blurred between the two. But we had connected and just, you know, most VC’s they’re friendly. They’re getting pitched by dozens or hundreds of founders over the course of a couple of days, those types of things. But yeah, I always, at the time, you know, I used to try and seek out a business card. I always carry business cards with me then. I still do now. Despite it being a digital age, there’s something about that tactical hand off to someone else that you can make a great first impression and you don’t have it forgotten because you sat next to them on the plane and they’re going on with their life, that it ends up in a briefcase or a pocket.

And then my preference is to get a card from them and always look them up on LinkedIn in real-time. If you’re talking to them like, Hey, Dan, so great to chat. Hey, like how do you spell your last name? And I’m pulling it up on LinkedIn and telling them, Hey, I just sent you a LinkedIn request. So that way, as they’re working through their, their inbound connections, they’re not just like, who’s this random person but they’re just like oh yeah, I met him at the conference or so and so at the airport. So LinkedIn for me is always step two. Get the card or get their contact info, go to step two. Send them a personalized invite on LinkedIn. I don’t know why people don’t to take advantage of sending just a blank connection request. It’s like sending an email with no subject line.

If you don’t know the first time, I’m not going to read this email, delete. So personalizing the LinkedIn invite is always helpful. And for me, it’s always a timestamp. It’s a timestamp because when that person accepts the connection request, it’s timestamped on LinkedIn. In the contact and subsection, and then the reason why personalize the invite as I try and leverage some context, where was I meeting this person?

What was the context of the conversation? And that always lives in the history of the messages between those two people? So, you know, I was connecting literally earlier on looking up on LinkedIn today, I was introducing our head of engineering to the CTO of a very successful startup here in town.

Connected with the guy back in 2017 and saw him speak on stage at a tech conference here in San Diego. That was my timestamp. I remembered the exact events. Matched it up. I always take photos of those events. I could go back into my photos app and match it up to the same day. It kind of takes our weak memory as we get older and it brings it back into full clarity.

And that’s been just a little life hack or professional hack for almost everybody that I need is go find them on LinkedIn. And if they’re active on Twitter, go find them and follow them on Twitter. And start to engage with their content because to bring it back to the example with Leront. Leront at Luma, we had no contact really other than just being digital and connected for probably a year and a half or so two years.

And then when we started Trust & Will we incorporated in October of 17, went through Tech Stars in early 2018, went out and raised our seed round in like July, August of 2018. He was one of the first people I reached out to, because I know he invests pre-seed and seed stage. I know he’s in LA, which is where most of my venture network is.

And on top of that, I know him. I’ve given him like a couple of years of my timeline with my previous startup, as well as this startup, to at least show that I can execute in some capacity in some faction. And while there’s never a guarantee that someone like him or Luma, the fund, will invest, at least it’s less hard intro to get when I’m ready to pitch.

And that’s how that kinda came full circle. And he’s been a friend who’s been a mentor now. I mean, they’ve been on the cap table for two full years and have participated in subsequent rounds. And the fact that I can text him for anything as if he’s a friend, not just an investor is something that’s really refreshing. And I can, I can use that example or a handful of people. That’s the connection to Leront and managing the network.

Dan Hightower: [00:17:29] Yeah. It’s huge. It’s that whole lines, not dots.

Cody Barbo: [00:17:33] Yeah. Yeah. Which those monthly updates that I send out. I mean, that, that is more than anything – if you want a pro tip if you’re an entrepreneur out there – sending out a monthly update to every single person you come across that you know could be a potential investor, that could make a potential introduction for you to a partner, a new hire, and then sending out those updates religiously the first day or the first Monday of every month. Asking people for questions or help. Connecting with people that have helped you, updates on the metrics, the team, marketing, PR, product updates, partnerships, miscellaneous category, you start travel category pre-pandemic. Cause those updates, it’s your track record. Like Leront obviously became an investor through Luma, but there’s hundreds of people on that update list that know the journey of Trust & Will, and even if they said no to investing, or they said no to a partnership opportunity. All we get to do is pitch them a vision. And then we have a year, two years, and some people have three years of updates on the company. So it’s like, what good are we other than our word that we can execute on a vision. And that’s what gets the company going in the right direction for the long term. Not just three years.

Dan Hightower: [00:18:38] How do you think about, let’s say I’ve got five ideas in a backlog. Sussing through them. And then, you know, I guess I’m asking that question within the context of, of Trust & Will. Like, how did you pick this one? And how did you know this was the thing you were going to invest your life in for the next several years?

Cody Barbo: [00:18:58] I was kind of toying of the idea of like, do I go work for a big company for the first time in my life, just to have like a really substantial income. It’s like the reality of being entrepreneurs. It’s not that glamorous. And so you have an exit event. Like, you’re just scraping by for the first years, there’s no guarantee of success.

Startups have an insane failure rate. And like, even if you raise venture like you don’t want to pay yourself some huge cushy salary in the first couple of years. Cause you want that to go to your team, you want that to go to acquiring customers, yadda, yadda. And I was like, do I go be a company man? Or do I stay true to myself?

Which is just. Go go at it again and hope my wife doesn’t leave me. And that’s the timing of it was really unique. I make light of it with the joke, but my wife, we were engaged at the time in summer, late, I guess like late summer, early fall of 2017. And I wanted to kind of take that next step in our own journey, getting a financial advisor in front of us, setting up life insurance.  And writing a will was just one of those things on my to-do list. I was like, I think people do this when they get married. And like the obvious inclination is to go to an attorney, but attorneys charges 3 to $5,000 for an estate plan. Like that’s ridiculous. Like why can’t it be as simple and intuitive as a TurboTax, which I’ve used for like a decade now? Like, I trust it. It’s legit and it’s dealing with something you do not want to mess up, your taxes, you don’t ever want the IRS knocking on your door. And, you know, it just like coincidentally, you know Daniel and our of course our co-founder, Brian, they’re the same life stage, but they’re also married now. All three of us are dads now. And the reality of our network, which I call the elder millennials for like 30 to 40. We’re not kids anymore. Everyone’s getting married, having kids buying their first home, really building their walls for the first time.

So when Daniel and I were catching up, it was August 4th, 2017. We went to breakfast at Mission Cafe in East Village, I think. Or actually, we got coffee, we got coffee and Monica commons, and we’re just kind of spitballing on a bunch of ideas. We’re talking about crypto, which was kind of crazy at the time. And like, literally that afternoon, he texted me when I was at breakfast, a later breakfast with another contact. Hey, what are your thoughts on this idea for like a trust and wills platform? Like, kind of a turbo tax for estate planning? Cause we talked about it earlier that morning. And like I have that text screenshotted. I have it timestamping. I’ve included it in a couple of decks just to remember the journey.

And it’s crazy that that led to literally two months of us meeting at my apartment complex’s like boardroom thing, whiteboarding, figuring out how large is this market? How many people have an estate plan? How many people don’t? What’s the average price point that they’re paying? What’s the average time that they spend from reaching out to creating it? Who is in the landscape today? Do most people do this offline with attorneys, or do most people do it online legal zoom? What are the startup players still going on Crunchbase or looking up any tech crunch fundraising announcements? And then looking up the founders of those companies, like what’s their story? What makes them advantaged to start an estate planning startup versus guys like Daniel, Bryan, and me? And we spent like literally two months just figuring this kind of baseline out.

And then on the most important subject is like, Do people even care? Like, do people our age care about estate planning? Or am I just one data point? So we went out and surveyed like 200 plus of our network. Which, you know, Dan went to school at Baylor, which obviously his whole network’s like married for like eight years now. On kids number three or four. My network at San Diego State, a little less responsible, but you know, some people are getting married and having kids now. And it was such a reflection of people that had kids, this was like an Oh shit moment. I don’t have an estate plan. I know I need one. Where can I get it done? And how much does it cost? Versus people that are single or maybe married, but don’t quite have kids yet. They’re like, it’s nice, nice to have, but not necessary.

So I don’t really talk to our parents’ generation, our parents about their state plans and that just created like a very uncomfortable situation for them because they’re not just thinking of their own estate plan, but also the estate plan of their parents. We have a grandparent that’s still around. They may have had an uncomfortable or a bad outcome, with that estate after that person passed.

We were like you know what, let’s bring it back to your last question on pitch competition. San Diego’s big, biggest pitch competition’s coming up. Let’s put in the idea. Let’s see if we make it onstage. And out of 200 or so companies that applied, we made it on stage. Top 10 companies in front of 500 people at Qualcomm’s headquarters, at their auditorium and we ended up taking third place and the rest is history.

Dan Hightower: [00:23:28] I mean, what I’m hearing in that story is this, do people care about their estate at this early, what’d you call it millennial? Aging millenial? Elder millenial.

Oh my God. I’ve got a family now. This value prop, which is, has historically been this like longterm useful thing. This, this work that I’m doing today will be useful when I die.

Cody Barbo: [00:23:52] Yeah, it’s an act of love. You’re doing their death documents. But, you don’t do it for yourself. Why would you care about yourself? You care about your family and that’s why…

Dan Hightower: [00:24:01] I’m fascinated by the way that you’ve taken a long-term useful product and made it way more accessible. But more importantly, you’ve turned it into a short term useful product.

Cody Barbo: [00:24:13] Yeah. It’s peace of mind. Like if you, pre-pandemic…like, if you are a parents with minor children and you’re getting on an airplane without them for the first time, whether it’s for work or it’s a vacation, you and your wife are getting away. Like, It literally is in your head, whether you want to talk about it or not. It is weighing you down on your shoulders. And people do these scrambled bandaid estate plans off other sites that I won’t name the night before the flight. And like, that’s not the mindset you should have going into this. Because it’s not just who looks after your kids. It’s who gets your assets? How do assets distribute over time, over age ranges? And who can make health care decisions and financial decisions on your behalf? All these things that go into it. And we’re like, if half the population doesn’t have an estate plan, for the half of the population that does have one, when’s the last time they updated it? Do they even know where it is? Is it reflective of their wishes today or is it reflective of their wishes from 10, 15 years ago when the kids were born?

So when we set out to do this, it wasn’t just go after the half of the population that doesn’t have an estate plan. We wanted to open up the funnel, create a larger market than exists today. For everybody. Since this affects every single living adult. Whether you’re rich or poor, you own a home or not. If you have kids, if you have a family member that you’re a caregiver to, you should need estate planning. Costs should not be a barrier. Education should not be a barrier. The experience should not be a barrier.

And that’s why, as we’ve gotten like, you hear the emotion. Like we’re three years into this. Like, we’ve made some meaningful traction. You know, we’ve got 150,000 families that have signed up with Trust & Will. But we’re just like at one hairline of the impact of reaching millions, hundreds of millions of people. And how will we want to help them think about estate planning?

So they’re not thinking of an attorney. They’re not thinking of Legal Zoom. They’re not thinking of estate planning at all. So our first impression of Trust & Will is oftentimes the consumer’s first impression of estate planning and how it impacts them and express to have an easy to use product five-star customer support. You can chat with our team live on site. Hop on a phone call. Email us. We’re monitoring all of our social channels. That’s what’s reflected in our five-star reviews. But most importantly, the ability to come back and make updates as life changes, you get married, have kids, buy a home, move States. You’re dealing with the loss of a loved one, or dealing with a liquidity event and sold a business. All of these updates should be reflected and it shouldn’t cost you an arm and a leg. And that’s what we’re doing is we’re, you know, democratizing the industry for people that would naturally go do this as they go through life. But also people that never thought they would ever set up an estate plan until they came across Trust & Will.

Dan Hightower: [00:26:42] Yeah. Okay. So you’re whiteboarding it out in your apartment like boardroom and you’re like, okay, well, uh, there’s obviously this company called Legal Zoom. And, you know, we may as a team be 100% sure that we’re gonna beat them in this space. But we’re going to have to like go out and convince investors and or customers that we’re the obvious solution for this. So can you walk me through how you…okay, so we’ve got this great idea, but there’s this like incumbent, we’re not afraid of them because we’re, you know, intimately aware of how we’re going to beat them. But the rest of the world doesn’t know that stuff yet. So like, can you think through, is it like, what is the likelihood of our ability to convince an investor or the market that we’re better?

Cody Barbo: [00:27:33] So legal zoom is as one example of many. They’ve been a private company for 21 years. They’ve had five or six CEOs. They’ve tried to go public I think just as many times. They are a marketplace of legal documents and services. They’re not an estate planning company. So our pitch from the beginning is they’re not an estate planning company. They have a ton of brand equity for business owners that are looking to create an LLC, trademark, copyright, all this other stuff. And then on top of that, not the reviews on their website, but the reviews on consumer affairs and Better Business Bureau on trust, you’re ranked horribly. Like one star, two stars across the board with words like scam, fraud, cheated. Like that’s not me saying it because we compete with them. That is literally what their customers have said for lots and lots of years.

And so I was like, okay, there’s another thing we can be better than that is customer support, customer service. Just kind of thinking through how do we do better than even in this space. Their product is kind of clunky, it’s kind of dated. Honestly, it’s estate planning product, in particular, has kind of been untouched for five or so years. It felt like it at the time, just looking at the modern, what a modern best-in-class FinTech app will look like versus a kind of a clunkier .com you’re a tech company’s products. So that was, I was like, we can compete with the product, and Brian and Daniel come from that background on the agency side, building better products than big companies could themselves.

And then on top of that, a brand. Like brand matters. TrustandWill.com was available. @trustandwill on all social handles was available. I was like, the stars aligned that I’ve never seen this moment for anybody trying to build a brand they want. Because I had to go acquire all those assets and Industry. We got everything except industry.com. We had @ industry on every social channel for my previous company, but it took me three years to make that happen. And I had to flex the trademark in some cases to get it. I had to go find people that have the accounts and try and communicate with them offline.

But with Trust & Will, all the digital assets were available. So I knew we could lead with a brand. And it’s very obvious, we’re called Trust and Will. It’s what we do is in our name. Versus Legal Zoom, is kind of an umbrella term. And one thing that I didn’t think would happen is I reached out to an investor who, his firm invested in Legal Zoom 10 years ago. And this woman introduced me to the CEO of Legal Zoom at like 10 o’clock at night. This is like, I’m not even joking. This, this really happened. Like two months into us starting this project. And she’s like come up to LA and meet with me. And we got Daniel and I drove up and got sushi with him. We spent like three hours with the CEO of Legal Zoom, this huge company. Cause who are we, we were like two guys, three guys with a vision. And that’s it. And he told us his whole career and journey and the legal zoom story. I mean, it was pretty inspiring despite us saying, Hey, we’re going to try and compete with you. And on his side, he was probably like, good luck kid.

Dan Hightower: [00:30:19] Was he asking for a job? 

Cody Barbo: [00:30:21] I think he just knew that we were too early or too small for him to give a flying f about. And he’s like, yeah, good luck. He’s like get to some meaningful revenue and come knock on my doors if you want to have a conversation. But that didn’t need to happen. But it was really cool that, that as one example of a competitive landscape was my dissection of Legal Zoom as a company. But then. On the flip side, getting up and getting an introduction to the CEO of a huge company. They have thousands of employees. They’ve been around for 21 years. Like that says a lot about their success, despite my critique. And we got his time and that’s something that a lot of founders don’t do, they don’t reach out to their competitors and try and look at it through their lens.

Dan Hightower: [00:31:02] Yeah, your definition of product is different than just the.com. You send out super high quality printed materials, you know, the actual printed version of the Will in a very nice binder. It’s a super awesome experience outside of the .com. Like tactile Trust & Will is real. And I always thought that was really cool because, you know, you looked at your competition, Legal Zoom, and it is put in your credit card to get this PDF. And the quality of the PDF was to be determined. But you know what you’re going to get with Trust & Will.

Cody Barbo: [00:31:38] Yeah, we wanted it to be very transparent. Like you can go the full test drive at TrustandWill.com Go from literally signing up to a hundred percent completed estate plan, still without paying. We put payment at the end so that you can take as much time as you need, review it with your spouse or partner, and review it with our support team through chat, educate yourself through our learn center content. Like that’s what we’re doing is we’re building trust. We’re competing against trust until people register. And then from registration to payment, we’re building their trust. We’re educating them. We’re trying to get them to not procrastinate this thing that people are not required to do, which is set up an estate plan.

And that’s what gets you to the finish line. And we’ve really thought through how do we, as much as I, can you say that your estate plan can be like a delightful moment when you unbox it and get it in the mail for the first time, then you go sign and notarize it. But like, that can be a pleasant experience. And for most people, it’s not. Whether they go through a Legal Zoom or they go through an attorney, we’ve really tried to elevate that. Cause that’s the hardest thing in the early days. You’re trying to win the trust of customers when you don’t have any. So like how do we get people that best first impression as early on as possible?

And then of course, now here we are three years later and it’s now a defensible pillar of our business is our customer experience, is our brand, is the package materials that we ship our customers documents in. And it’s just, it’s something that you either invest in, or you don’t, and you can still be successful without it. But, we rather prioritize it to encourage it to other founders out there is what that customer experience looks and feels like as early as possible.

Dan Hightower: [00:33:09] Yeah. You came out early with a really well-scoped product, wrapped in a really great customer experience, which enabled you to test product-market fit really early. Relative to a company who’s got this vision and they’re testing the vision at the same time they’re trying to roll out a product.

Switching gears a little bit here, but I’d like to get down into like the weeds on early customer acquisition as an early sign of product-market fit. How have you thought about adjusting the price point and managing your cost to acquire?

Cody Barbo: [00:33:41] It took us almost a year to get our will product nationwide. We raised the $2 million seed round. It took us another seven, eight months to get the trust product out nationwide. We just started it with California and Texas trust and then we expanded to more States. And estate planning is state-specific. So I think we took a really thoughtful approach. And why we didn’t…we did things that didn’t scale early on. And then as we started to figure out our product, we started to test pricing. We always, you know, always testing pricing, competitive to what the current online landscape is. But I don’t think that’s always the right way to approach pricing. Pricing should be determined on the quality of your product and the expectations that a customer is receiving as they go through it, whether it’s a digital or physical good. And I think we have a lot of opportunity to increase the cost of our prices. We’ve increased the service layers beyond the initial purchase order. Because our product is a set of documents upfront. But over time, the ability to come back and make changes, upgrade to an attorney, adding, I don’t want to say the bells and whistles, but adding a more comprehensive estate plan as your wealth and assets grow is part of our longterm vision and strategy. So pricing adjusts appropriately the same way that your pricing would adjust appropriately with the financial advisor or your insurance would price appropriately over time.

The first year with paid acquisition was also, we just needed to get people to the website. I mean, that was like really the ultimate test. Like we can kind of get people through our product through our own network, but how do we even get people to the site and get them to register. And here we are three years later, we’re getting hundreds of thousands of visitors monthly to the Trust & Will website, which is amazing. That’s our investment in SEO, our investment in our brains, the partnerships, the press that’s come along with the fundraising announcements. But we still have to convert the people on site. So like now we’re like, that’s not a cult that our conversion optimization from getting a site visitor to registration, site registration to a paid customer. Working that funnel over time for retargeting drip campaigns. It’s any engagement that we can have with people to get them to a paid a customer. It’s, you know, that’s what our whole company is built around. Now. With 22 people.

Dan Hightower: [00:35:45] Was your pitch early on that like, did it include any mention of cost to acquire customer early on?

Cody Barbo: [00:35:52] We could have done some back of the napkin math to try and calculate it based on the hourly rate that we were paying ourselves, which was next to nothing. The number of customers we acquired over a certain period of time. Like we could have figured it out. It just would have not looked that clean. And I think that when you’re in the earliest days if you’re going to venture route, which is going to go raise capital from private investors. If there’s five things that they’re investing in the first three better be team. Like, why you? Why now? Why are you the team geared to do this? The fourth might be the market size, which in our case estate planning is a massive market. It literally is the transfer of wealth and assets. A trillion dollars passing between generations every year. And that applies to every living adult in this country.

But then the fifth is meaningful traction or revenue. Any sort of partnerships for IP. And that’s always the variable when you’re probably seeing a pre-seed pitch deck or even seed stage pitch deck is that some companies might have none of those things. We were one of them. We didn’t really have any revenue, any substantial traction when we raised that first half million when we got into Tech Stars. But we had the team, we had me, the entrepreneur, Daniel, the business development operations guy, Brian on products. And very quickly hired another engineer and our in house attorneys. So a team of five as we kind of started the Tech Stars process in January, 2018. And that helped build confidence. I hope that built confidence for you to participate as an investor, but also for us to get into Tech Stars, the highly competitive accelerator.

And then once we were in Techstars, it was just like a complete shift of mindset of like, okay, we’re going from things that don’t scale to like, we need to figure out how to operationally scale. Tracking our KPI’s and OKR’s. Being diligent with mentor updates or investor updates, or those monthly updates that I was sending out. And letting people poke and prod. I still remember some of your, you were the first person probably to poke and prod on those first couple of emails that went out on the numbers. Like, break this down further for me, like this doesn’t make sense. This doesn’t add up. You look back through previous month updates and sometimes that’s what it takes a little bit of a kick in the ass from an investor or a supporter to dig in and be like, how did you calculate this? Versus like, did you just make it up out of thin air?Like how did you calculate this? And I feel like that’s the job of an investor for sure is to ask those types of questions. But it’s also the lens that a founder should look at is if I could ask this question, how am I going to explain it? How am I going to back it up? What are my data sources? How do I just not lie and make it up?

And it’s okay to not have an answer and to not know and get back to someone. Yeah. That’s, what’s taking me as an entrepreneur, I think the longest to do is to just say it’s like, Hey, I don’t know. That’s a great question. Let me figure it out

Dan Hightower: [00:38:28] Huge sign of maturity. Yeah. I have no idea, but I’m going to get back to you on that.

To wrap up, let’s do secret weapons and the things in your life and work that give you an unfair advantage. Your secret weapon for personal learning.

Cody Barbo: [00:38:43] Yeah, sleep. Get seven hours sleep every night. Like it’s such a stupid thing to recommend and how obvious it is, but getting a full night’s rest has changed my life and will make you much more refreshed for the challenge ahead.

Dan Hightower: [00:38:55] What about a team culture? Secret weapon for team culture?

Cody Barbo: [00:38:58] Yeah, treat everyone as if they’re family. It’s such a cliche thing to say, but like we have such a winning culture at Trust & Will. And I think with the environment that we’re in with virtual, we’re all virtual and, you know, across the country and across the world. But yeah, like personal and professional are one in the same. They used to be very different things. You could be someone else at home. He could work, go to work every day. I think really understanding people’s family dynamics. Like I’m almost positive I could name every person on the team’s partner, kid’s name, dog or cat’s name. And those are details that sometimes leaders don’t care about. Like I care about people’s birthdays and anniversaries and like their kids’ birthdays, or if they got a new roommate or if they had a new life milestone. Like, what else matters if you’re not celebrating someone’s personal life wins, why should they want to celebrate the work and company wins? And I’ve tried to keep that mindset, you know, for many, many years, not just with startups, but even in past organizations. It makes a big difference at the end of the day.

Dan Hightower: [00:39:56] That’s huge. Okay. Last one. Secret weapon in your tech stack.

Cody Barbo: [00:40:01] Carta. Having an organized cap table, that’s the greatest thing on the planet, because it just makes your life way easier. If you’re going to go to the founder of venture-backed founder route and bringing on co-founders, bringing on a team, raising money from investors, it keeps everything organized and compliant. You aren’t selling securities at the end of the day. So if you want the SEC or the IRS knocking at your door. I don’t recommend it. It hasn’t happened to me, but I don’t recommend it. It always goes south. And if you find success in taking your company public, or for large acquisition, having the crystal clean cap table does wonders for you and your business. So shout out to Carta.

Dan Hightower: [00:40:37] Thank you, Cody. Thank you so much for listening. Please subscribe or more amazing conversations with venture-backed founders like Cody, and you can find the notes and the newsletter from this episode at productmarketmisfits.com.