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Starting a Company as an Underrepresented Founder
Charley Moore, Founder & CEO of Rocket Lawyer

Charley Moore started Rocket Lawyer with the mission of bringing affordable legal help to consumers. Thirteen years later, more than one in nine Americans now has a Rocket Lawyer account, including thousands of employees who access these legal services through their employer-provided benefits.

Along with expanding access to the justice system, Moore is passionate about inclusive workplace environments where diverse ideas, founders and individual contributors can thrive. In this episode, Moore talks about how his experience as an underrepresented founder has shaped his career, how the tech industry can build a more inclusive pipeline and how companies can align profit with their purpose.

Charley Moore, Founder and CEO, Rocket Lawyer

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Show Notes

Mitch Zuklie:

Welcome to Future Fountain, a podcast dedicated to conversations about the tech ecosystem brought to you by Orrick and NYU Future Labs. I’m Mitch Zuklie from Orrick, and today we’re thrilled to have as our guest Charley Moore, the founder of Rocket Lawyer. Charley is a phenomenally successful disrupter in the legal services space, and he’s also a long-time personal friend and a visionary I greatly admire. Charley, thanks so much for joining us.

Charley Moore:

Hey, Mitch. It’s a pleasure to be here with you, and you’re too kind. I’ve known you too long and so you know all that stuff isn’t really true, but I appreciate you saying it anyway.

Mitch:

I hate to say it, but it is true. Let’s dive right in, Charley. So, maybe you can tell us a little about Rocket Lawyer and what caused you to found the company.

Charley:

Sure. Like you, I started out my career as a Silicon Valley attorney, representing startups and tech companies. But before that I grew up in a family business. My dad has an eighth-grade education, formal education, lifelong learner. He was a truck driver; he learned how to drive big rigs in the Air Force driving fuel trucks. And so long story short, I grew up with a really blue-collar family. My dad ended up having a chain of gas stations and small businesses. I grew up seeing the difference that education and good advice could make for a small business owner. And then fast forward to working in Silicon Valley and seeing the kind of resources and access to great lawyers like Larry Sonsini and Mario Rosati and Craig Johnson. You are familiar with all these legendary men who were the tech lawyers that mentored us, and companies like Yahoo and well-funded startups. I saw the big difference in access to great legal advice and, quite frankly, the tremendous benefit of great legal advice for a business owner. And so all of that kind of percolated together in Rocket Lawyer. I like to say I’m a recovering high-priced lawyer. And so, being able to use digital technology to give regular folks access to that kind of lawyer, because lawyers really do make a difference. We call them the tools of justice, and giving regular folks access to the tools of justice digitally is what Rocket Lawyer was founded to do.

Mitch:

Tell us more about the business today, Charley. We’ll go back to its founding a little bit more but tell us more about the company.

Charley:

We started Rocket Lawyer a little over a decade ago with a really simple mission to make law affordable and simple enough for everybody. Like companies I admire – companies such as Southwest Airlines and Walmart and Amazon. Rocket Lawyer really started with that North Star of providing value to regular people and small businesses. I’m really proud of the fact that today about one in nine American adults has a Rocket Lawyer account. We have about 30 million account holders in the U.S. We also operate in the UK and in Europe. We have a terrific team of people that have worked hard on this mission, and so we’ve been able to scale the business a bit. Lastly, we have hundreds of thousands of people who now get Rocket Lawyer employee benefits, and a lot of those are tech employees. So, Facebook and Google employees and Salesforce employees and many other great companies provide Rocket Lawyer as a benefit. And so, to achieve our mission of bringing the benefits of legal help to everybody at a price they can afford, I can’t think of any more gratifying way to do it than to make it an employee benefit like health care, and we’ve been able to do that.

Mitch:

It’s incredible to me that you’ve grown in 12 years from an idea to one in nine Americans having a Rocket Lawyer account. It’s just phenomenal success. A great accomplishment.

Charley:

It’s humbling.

Mitch:

So, you founded this company just a month before the 2008 financial crisis. What was that experience like? And also, as a Black founder, was race a factor for you in deciding to become an entrepreneur in any way?

Charley:

So, I’ll take them in turn, and I think I’ll start with the last question. I’ve been blessed, Mitch. For sure, race has played into my life like every other Black person in the world. Going all the way back to integrating into a Boy Scout Troop, being the first Black family in our scouting troop, and my mom was a den mother for Cub Scouts. I bet in Florissant, Missouri, in the 70s, she was the first one of those, too. And so, you certainly know that you are the “other.” But by the same token, you develop lifelong friendships. But you do go through some stuff, and I’ve definitely gone through some stuff in my life and been certainly victimized by racism in my life from childhood all the way up. But it hasn’t defined my life at all.

I would say that my decision goes back to the fact that my dad was an entrepreneur. I grew up in an entrepreneurial family. I never saw my father draw a paycheck from somebody else, ever. I only did that myself for my Navy service and for the couple of years that you and I practiced together. I’m 55 now and I’ve had, I think, maybe three job interviews. The summer associate interviews. I really just don’t know any other way to live, and I think the advantage of growing up in a family business like millions of other people showed me there’s another way. Like, you can work for yourself, and you can build a business. That’s how I grew up. I think it’s more about having mentoring, and I was blessed to have that. I tell other Black founders that this is hard for anybody, period. Is it going to be harder for you? Is it harder for me? Yes, there is no question about it. Is it harder for me to raise money? Yes, no question about it. But I don’t lose sight of the fact that, like the NFL, this is hard for anybody. Period.

Mitch:

Let’s focus for just a second on some data. I think the data on how diversity affects the startup ecosystem is pretty sparce, but according to BLACK VC, I think 80% of U.S. venture firms don’t have a single Black investor, and only 1% of venture-backed startup founders are Black. How do you interpret that data, Charley? What should we make of that?

Charley:

I’ve been thinking a lot about this since the events in 2020, I have been asked these questions more, and I think that’s good. Since Mr.Floyd was killed. The reality is we’re just getting started in terms of real inclusion – and I use that word with care – real inclusion as far as women and Black people in Silicon Valley. And in the entire ecosystem. From lawyers to engineers and investors, across the board, we’re just getting started with inclusion.

 

I am proud of the legal profession. It’s got a long way to go, but of the three that I just mentioned, I think the legal profession is more inclusive, but still has a long way to go. And you can see that in, folks like Carlos Watson, who’s a former Wilson Sonsini attorney and the founder of OZY Media. For myself and for others, law has been a stepping stone into developing relationships with folks who can fund you, who can hire you in a business capacity. For my cohort, in the time we’ve been practicing, I’ve seen a number of Black attorneys and women also move from being lawyers to being business people and investors, so that’s heartening, that’s neat for our profession.

On the other hand, the technical fields are really far behind. I have a Bachelor of Science, and I think that’s one of the things that helped me a lot is that I coded. I took computer science classes in college, and I coded, then I even took more computer science classes when I got a Master’s degree. I have always been a coder since I was a kid – I started programming BASIC on a Commodore 64. I think being interested in coding and at least dabbling in it has definitely helped me. We just need now to have more of a pipeline for Black, female and other non-binary people and other folks who are underrepresented. We certainly need more of an opportunity to have a real technology pipeline and mentoring among technologists for those underrepresented groups of people.

I’d probably also say the world of finance is far behind, and the reality is that the venture community, historically, was very much an old boys’ club. That’s changing, and it’s great to see it changing. I’m seeing more and more women VCs. There aren’t very many Black VCs, but that’s starting to change, too. You will see more female founders getting funded and you will see more Black founders getting funded as there are more women VCs and Black VCs. There’s no question you will see more women and Black VCs, in my humble opinion, when the folks who write the checks to the VC funds care about it and vote with their checkbook that they care about it. And those are pension funds, college endowments, etc.

Mitch:

Very helpful, Charley. I’m going to add: I know there’s someone listening out there today who is thinking about founding a company and would like to hear directly from you what advice you have for diverse founders. Before you engage in answering, I’ll just share something for the audience that they might not know. You and I went to law school together. We spent our second summer at the same law firm, and you encouraged me to look at that particular boutique we started at. I recall that summer you were the star associate working on the Yahoo IPO, I think I was working on a bagel company IPO, and I’m sure that we both started out of law school together. I think we were at a firm where it was a little bit “sink or swim.” It seemed to me like you dove into the pool and could swim butterfly; I felt like I was dog paddling for a number of years. You seemed to be miles ahead of the rest of us, and then it surprised me that you decided to leave the practice because you were doing such a great job as a lawyer– as a third year, maybe even a second year – and form your own company. What motivated that, and what advice do you have for folks thinking about making that same jump?

Charley:

Well the real answer is, and I tell everybody that asks me the question. You know Mitch, you’re the best lawyer that I know…

Mitch:

That’s nice of you to say.

Charley:

…and you were the best lawyer that I knew then, and I realized I would be better as a client of yours than a colleague in law practice. And so I really mean that.

Mitch:

By the way, I felt just the same way, Charley. So, it’s interesting that we both had that perception. I felt exactly same way about you, but I didn’t have the courage to start a company, and you did.

Charley:

Well you shouldn’t, you’re a great lawyer, and I mean that as high praise. It really is, and I knew that going back all those years ago, and it’s held, Mitch. And so, to sort of go back and to think about what’s the right path for anybody and then to thank Mike, you know, personally. The world needs all kinds of folks, and so finding your lane really leads to a lot of gratification. You found yours because you’re a great lawyer and the world needs that. And, for me, I sort of think of myself now with a few patents as an inventor and I think about that in terms of the team that I tried to put around myself. Example: I just hired a VP of operations at the company, Frank Walder. Frank’s great and Frank knows a crap ton more than me about scaling operations, for a business with millions of customers, and I don’t really know how to do that. But I did invent the product that he’s going to now scale. So now, I’m thinking about other new products and try to have a team where I can think about the new products and they can do their thing, whether it’s marketing or what have you.

But back to starting something. I’ve had people ask me, “I’m thinking about starting a company.” It’s not starting a company in my mind, at least for me; for some people it is, and I can’t speak to them. For me, it’s inventing something, and the invention is first, and the company is second or third or whatever. Inventing something solves a problem, sometimes a problem that people didn’t know they had. There are a lot of great inventions that do that. Each time that I ended up having a startup and going back to the beginning, it was inventing something and then building a company around the invention. For anyone who says starting a company isn’t a career move, I tend to say to people, and this sounds sort of like a tautology, but I do say it, “If you’re going to do that, then no matter what I say to you – we’re going to have breakfast or lunch or something two years from now and you’ll have done it. And what I say to you has nothing to do with it, and what anybody says to you, quite frankly, has nothing to do with it. You’re going to do it no matter what.” And both when those were my clients and probably the same with you and then doing it myself, for the most part, the feedback that I’ve gotten has been negative. I mean it’s been, “That doesn’t make sense” or “Blah, blah, blah,” and then you do it anyway. And so, I’ll stop, I’ll take a pause. I love hearing entrepreneurs talk about how they got started. I love that conversation and it’s something I think a lot about.

Mitch:

How did you build your team? You’re an inventor; you have this idea for Rocket Lawyer, you had it for other previous companies. How did you go from one inventor with a strongly held view that this is a product that’s going to help people, regardless of the feedback that you got? How did you get others invested in taking that trip with you? How did you achieve that?

Charley:

Oh my gosh that is such a good question. Ahh man, man….you might bring me to tears with that one, Mitch. You can’t see on the other side of my wall here, but I have a print of this – I wish I had the original. Maybe if I had stayed with your career I would, but I’ve had it since literally I think it was at my apartment at law school. And it’s the Pablo Picasso sketch of Don Quixote and Sancho Panza – everybody’s seen it, or most people have probably seen it. I see it every day when I’m here in the home office. And so anyway, you’re tilting it, when you’re an entrepreneur, when you’re tilting at windmills and you’re saying they’re dragons or whatever and you’ve got to find your Sancho who believes it. Here’s the thing, in Don Quixote, Don Quixote actually knew what Sancho was looking for because he asked him. He said, “What do you want?” and Sancho, at some point, told him he wanted to have his own island and, at some point during all their adventures in a thousand pages, lo and behold I think it was Ibiza, the Spanish island, the natives of Ibiza or whatever made him the governor, and so Sancho got his island. And so too is the way that I think you get people. I’m really proud of the fact that Rob L. Hart, the first guy that I hired at Rocket Lawyer, still works at Rocket Lawyer.

Mitch:

That’s fabulous.

Charley:

Rob and I are good friends now, and I’ve noticed that with different folks. A few years ago, I was lucky enough to have lunch with Reed Hastings, the founder of Netflix, and the guy sitting next to him was the first employee at Netflix. There is nothing more gratifying than to be on a long journey and a life’s work with people that there’s trust in both directions, respect in both directions, and you’re on this journey together, across the Spanish countryside metaphorically or what have you. The way I think you get people to join you is with sincerity. A sincerely held mission and folks who want to achieve that mission, and what motivates them is achieving that mission, that sense of purpose for whatever it is. Believe me, we’ve been through all kinds of ups and downs and adventures and not always great outcomes, but overall, we’ve known what our North Star is: To make justice successful and affordable for people. We’ve gotten the law changed in different places. We got the law changed in the UK, we got the law changed in Utah, and the law just changed in Arizona.

 

And the last thing I’ll say: One of the other really gratifying things is when we survey our team. People who’ve been at Rocket Lawyer for more than five years, and there are quite a few of them now, are so happy. They’re happy warriors.

Mitch:

Is that because of the mission? Is that because you want to be the Amazon and Southwest and Walmart that you admire of the legal access space and you are helping more people get access to justice? Is that what’s doing it?

Charley:

I think it is. I mean, it’s definitely not me; it’s that they bond with each other; they bond with the mission. It’s also that they’re resilient. And those are the people who’ve gotten through the difficult times, and so it all works together. We try to find people now who have shown that they can be somewhere for, I like to say, a decade. People overestimate what they can do in a year and tend to underestimate what they can do in ten years. And we like to see those people who’ve had a ten-year experience someplace because then they’ve been through tough times. And seen it through.

Mitch:

Let me ask a related question if I can, Charley. You just described beautifully what it’s like to create this band of brothers or sisters on this journey with you together through the adventure doing something, creating a product that helps a lot of other people. Is it the same in terms of enlisting people who are mentors and sponsors for you? If you’re that person thinking about taking that first step to being a founder today – one thing is getting others to come on that journey as colleagues; it’s another thing to find someone to help advise you and to be a sponsor for you. Is it the same recipe to get someone to help you there or is it different?

Charley:

Well, I’ll just take a stab at it. I mean, Harry Greeman, Ken Coleman, John Thomson, David Drummond, on and on, Black men who have mentored me. Stacy Brown Phillipa, a Black woman who’s my same age cohort, roughly – sorry, Stacy, I know you’re younger than me if you’re listening – but who I’ve learned a lot from. And I can name so many other folks.

I think reaching out is really important. I have yet to reach out to somebody who has gotten farther down the road than I feel like I’m traveling who has rebuffed my sincere outreach.

I’d include Josh Greene who’s not Black, and so I’ve been really blessed to have mentors and friends like you and colleagues as a full circle of support. And I have yet again to reach out, number one, and then number two is being receptive. I’ll keep this sort of anonymous but I did meet a young African-American founder who reached out to me doing a reference check on somebody that I had worked with previously. This particular founder seems to be brilliant and, unlike me, is a real technologist. Graduate of a terrific, top five computer science program and has gotten funded already. When you talk about the 1%, this is one of those 1%. And he just reached out to me in the normal course of business and we started a conversation, and I look forward to developing that relationship because I’m going to learn a lot from a twenty-something Black inventor, and I think maybe he’s going to learn some things from the fact that I’ve been doing this for 20 years now. Just do your work and don’t be afraid to outreach and develop that network of support.

Mitch:

Super helpful. Completely actionable as well so thank you for that. Let’s change topics for a little bit. When you and I were in law school, we heard the purpose of the corporation was to enhance profit for shareholders – period and a full stop. I think that we’re starting to see a shift perhaps to stakeholder capitalism more broadly, as we’re hearing from places like Black Rock all the time. Do you see that and, if so, is that the right direction for us and should we sustain that effort, or is it just window dressing?

Charley:

Definitely, Mitch. There have been differences of opinion among some great companies, and I’ve had conversations going back years with founders of some household name companies who were adamant in saying what they do with their personal money is their business; what they do with their shareholders’ money is not. Whereas other companies, like Salesforce from day one, Mark when he founded the company very small was all about some community engagement. Institutionalized community engagement. I really admire Mark and what he’s built at Salesforce – disclosure: they’re one of our customers – but I really admire that company very much. And the ethos around community engagements.

 

I’ll just speak for Rocket Lawyer – we set out years ago to engage with the community. It was very ad hoc. We supported things like One Justice, Legal Aid, we’ve done casino nights at the office and worked at food banks, and it’s always been organic with the team and not really company policy.

 

But the team really ran with it up until two years ago. As we became profitable, we then started having a formal budget for community engagement. Which probably your law firm and many others have and have done for years. So we have that now, Mitch, and this year we’re going to actually hire somebody who’s going to own that as an executive. This idea of creating value we look at as a circle, and first it’s to the customers. So I will say for anyone who’s starting: Who’s your customer, what are you doing for your customer? Many, many years you need to just focus on that. Then, to us, the next spot in that value is our team. And the spot after that is community. We want to answer the question, and the older I get the more this question becomes really front of mind, is: How is the world better because you worked, not because of the work, but how is the world better? And at some point, I think that’s the question that our team wants to be able to have a good answer to. And that’s where our community engagement activity is and hopefully creating a flywheel where yes, we’ve created a for profit and all the things you said company. For us stockholders, because we’re all stockholders that’s the – we think if you do the other things right, the last one takes care of itself. But if you just focus on that sort of old school, “we’re going to pay dividends to the stockholders,” you don’t end up inventing, and you don’t end up innovating; it’s just not a virtuous circle. But if this stockholder value is last – it’s there, it’s just last – you create that virtuous circle, and that’s what we ultimately want to have and that then rebounds back to some of those profits by policy for Rocket Lawyer go to community engagement and I hope, knock on wood, always will.

Mitch:

That’s incredibly helpful. By the way, do you think that that focus beyond customers and stockholders to including community has enabled you to attract and retain better team members? Just curious if there is a benefit associated.

Charley:

For sure, oh yeah. I have some really awesome people working at this company who I can tell you were totally fed up with me. They were done with Charley Moore. But they weren’t done with justice as a mission. And have pulled me along and reminded me of that mission. On many, many occasions and I know that’s what they’re here for.

Mitch:

That’s such a great answer. What should we be thinking about as a tech community Charley? How can we as members of the tech community become better allies for a more inclusive ecosystem? How should we think about that differently? What can and should we be doing, and why must we do it? I would love your thoughts on that.

Charley:

In concrete ways I would love to see the tech community to commit to, I like the word inclusion, even more than diversity, right? Inclusion, I just like the word; it feels like a circle, it feels like a hug, it feels like an embrace, right? It really does, and so you know what is it going to take to embrace, not to just sort of go through the motions but to really embrace diversity? To embrace it. I think that means things like recruiting from different talent pools, historically black colleges. Like really embracing historically black colleges. Like really embracing, widening your lens beyond standardized tests, etc... Now I will say one of the things that gave me a big leg up is I was good at those tests. But it also let me get away with some other things that maybe I shouldn’t have been able to get away with. Because I could go take a test.

Charley:

And so, inclusion means people who have all different ways of learning. They bring different assets to your organization. Probably, to be quite honest about myself, because I can take these tests and get through them, I’m probably not the right one to do that really heavy lifting of operations day-to-day. I’m not that good at that. And so the testing doesn’t show that I’m going to be good at. In fact, it doesn’t show it at all. So, these standardized tests are not going to universally get you the people you need for the tasks at hand. And so that’s one area that I think we can do better. And I’m actually happy, as a good standardized test taker, to see schools, including the one I graduated from, starting to move away from that as such an over-indexing for that particular skill. I could go on, but I’ll stop and just say that these ideas, once you embrace inclusion, you, the company, the organization is going to have so many great ideas and so many things. Lastly, you know software’s my business – trial and error, iteration, test and learn, right? Test and iterate. And so, we have to start to optimize for inclusion the way we optimize for conversions.

Mitch:

Do you think that’s something that we need to be measuring consistently? I think you have the view that it’s important to measure and set priorities and measure progress against them. Is inclusion something that we’ll be measuring against, and if so, how do we do that?

Charley:

Absolutely, yeah. KPIs and measurement are the way we run all of our businesses. For example, at Rocket Lawyer, again, and I only speak for our own business, and also knowing that this stuff is hard. We are a little under 50% women, high 40s percent women, and our board has three African-Americans, three Black board members, and one female board member out of seven. So, a majority of the board is women and people of color. But our technical team is in the low single digits of Black representation. And so we have work to do there, and I think part of that is – if anyone is going to say, as a Black founder, the pipeline and investing in education and technical education is so important and is going to hopefully expand the pipeline over the next several years. But I think it starts with transparency. And so kind of walking the talk is why I just told you our numbers.

 

People need to care about those numbers for the companies they do business with, the funds that they invest in. And as that starts to happen, well that’s what capitalism is all about. So now you’re back to community engagement and so forth for those folks who just want to increase value for shareholders. Well, then that’s how it’s going to happen.

Mitch:

Two last questions, Charley. Do you think that the fact that your leadership and your board is four out of seven diverse is a material benefit for you at identifying, attracting, retaining and advancing those single-digit Black technical leaders that you want to add to your front? In other words, is the fact that the leadership at the top is diverse a huge competitive advantage for you in terms of attracting and retaining others in making a more inclusive company? And you can control that – you can control the board, you control the top, really, that’s something that you actually could control in a way that might have real impact on the rest of the organization. Is that right?

Charley:

Yeah, investing in founders that are diverse is the starting point for the companies that do manage to scale for what their governance is going to look like and then what their teams are going to look like. And sure, I mean, it becomes natural. I mean, you’ve been to so many board meetings, Mitch, in your role. And when you’re there at those company board meetings and the leadership team, the operating team for the company comes in and presents to the board, what that board looks like and what that board contributes back again really changes – the dynamics change. If the team doesn’t look like the board or the board doesn’t look like the team – and again, ultimately, it should look like the market. It should look like the customers. The market that you operate within and the world that we operate within is a diverse world. And so, ultimately back to focusing on your customer. Reflecting your customers in your board and your team has a lot to do with that.

Mitch:

Very helpful. Last question from me, Charley: Are you optimistic?

Charley:

Ah, I’m so optimistic…

Mitch:

I kind of knew that answer before I asked.

Charley:

Yeah.

Mitch:

Tell us a little more about that.

Charley:

We’re not out of the woods yet on one of the most disruptive, in a bad way, periods in our lifetime, right Mitch?

Mitch:

Yep.

Charley:

With 2020, the pandemic, social justice, the January 6 attack on the Capitol – I mean, just unprecedented turmoil in the world. And yet, the world has been through other pandemics. 1918…

Mitch:

Sure.

Charley:

We couldn’t work from home, right? You look at the difference. You couldn’t develop a vaccine using modern, RNA techniques the way that we have today. So, I’m incredibly optimistic in technology. I think, and back to technology and Silicon Valley, what do we do? We invent, and I think we can invent solutions for these problems, and I’m really excited to keep at it.

Mitch:

Charley, thank you on behalf of everyone who’s listening to this podcast and everyone who’s joined us on the Future Fountain. Thank you for your insights, for your candor, for your optimism, for your commitment to inventing, and for your commitment to making the justice system more accessible to everybody. Cannot appreciate your involvement in this podcast anymore, and I couldn’t be more grateful to have you as a friend.

Charley:

Mitch, thank you so much. And everything that Orrick has done – I didn’t mention The Observatory, but I think that’s a terrific resource for identifying companies, founders that are diverse and the legal tech landscape. And sort of the fact that Orrick created that I think is just a terrific asset to the community, and I know that Orrick is doing so much for diversity. So, anyway, my friend, great talking to you, and keep up the great work.

Mitch:

It’s great to talk with you, Charley, and congratulations. It’s amazing to me to think that one in nine Americans has a Rocket Lawyer account. It’s just an incredible thing. And I can’t wait till it’s eight out of nine.

Charley:

It tells me we’ve got eight more to go.

Mitch:

See ya, Charley.

Charley:

Alright, see you later.