Being an Under-represented Voice in the CTO Chair

A conversation with Tramale Turner, CTO, TaxBit

Tramale Turner is the CTO of TaxBit. We met at the LeadDev LeadingEng conference in London. When I met him I thought I bet he has some great leadership stories for us. I invited him on the spot and am grateful he said yes. We talked about how growing up in Detroit influenced his career, investing in himself, and why he decided to join TaxBit as the CTO.

Can you give a quick introduction of yourself?

I’m Tramale Turner CTO of TaxBit. I've been an engineer and a marketer for over 25 years. I started my career in Tokyo of all places. Originally I'm from Detroit, but I left Detroit when I was 16 after I graduated high school, went off to the University of Pennsylvania, spent a few years at Penn in the Moore School of Engineering, studying computer science engineering, and then somehow found myself studying Japanese as well. I left after three years at Penn, moved to Japan as a software engineer, worked at a little company called NET 5, came back to the United States, started a company, sold a company, and went to a couple of failed startups after that, then ended up in the Volkswagen group for a number of years, almost 10, and had a lot of interesting trips gallivanting around the world. But that was also me working initially as a marketer at Volkswagen and then finding my way into engineering from the marketing organization. Left Volkswagen, joined the Nissan group, working on the Infiniti brand, again as a marketer, and then went to this little video game company in Pacific Northwest called Nintendo for about nine years. People may or may not have heard of that.

I eventually ended up in F5 Networks after leaving Nintendo for a brief amount of time. Just about 13 months. Then I ended up at Stripe, this little FinTech startup that is apparently one of the most valuable companies, private companies on the planet. For three and a half years I was the site lead for Stripe Seattle. I ended up at this little startup that's trying to enable digital assets or intangible assets, as people say. Some people know them as cryptocurrencies, probably most popularly, as it's CTO and have been enjoying every moment of that.

I'm from Detroit, too. I grew up in Warren, which for those folks everybody knows Eminem's eight mile. I grew up on 14 mile. Warren and Detroit, are right next to each other. You also graduated high school at 16. How do you think those things affected your trajectory?

Oh, I think it definitely affected my trajectory. One thing that probably propelled me in direction. Well, maybe a couple of things, intersectionally, I wanted to get out of southeastern Michigan. I didn't see myself in the auto industry, even though I’ve worked at two automotive companies. It was not something that really appealed to me as sort of a location. I wanted to see the world. I wanted to see what I hadn't seen growing up in Michigan. And I was 16, so I don't know if I was smart or not, but I was like a dumb kid just like going, "I got to get out of here. So I'm going to go off to this fancy school that I got accepted to, and that's going to change my entire perspective on the world and life."

I think really the thing that growing up in that area did for me is — a lot of people say this sort of the canonical thing of coming from that area, or anywhere in the Rust Belt — is you grow up tough and you grow up able to face any sort of thing because that area has been through so many stories. And yeah, to some degree that's true. I think I came with a fortification and the foundation that helped me be extremely resilient. I've never faced anything that was like some of the things that I had seen growing up in my neighborhood. So I always have this overly optimistic perspective. I always think about the opportunity whenever I see a challenge because I've seen so many terrible things.

The other thing is, for what it's worth, the greater Detroit area has a very storied engineering foundation as well. Automotive, mechanical engineering, chemical engineering, to some degree as well, not so much the computer sciences, but that was a thing there as well. The high school I went to was called Cass Tech. I majored in computer programming at Cass Tech, where you had to select a major as a matriculating student. So that definitely shaped who I am.

Cass Tech is a renowned school. In my high school class, maybe only half went to four-year colleges. Some went to community college, many went to work on the line. In my experience, growing up in the Detroit area builds resilience. When it comes to my career I’ve just figured out how to go with the flow and be resilient.

We definitely share that for sure.

I'm a New Yorker now, but you will never take the Midwestern out of me and I'm proud of that.

I totally agree. Totally agree.

I think you said you’ve been in startups before?

When I left Penn I went to a really small company before this whole ethos of startups and a YC batch or going to founders fund or anything like that, but became popular. There was this small, I mean it was a startup quite frankly, in Japan that I joined and we were building something that didn't have a name at the time. We were just writing software, targeting interactive CD ROMs, and then websites. So we were doing interactive marketing without knowing that's what we were doing and writing custom-developed software and interactive packages that did quite well for the business. When I moved back from Tokyo to Michigan, the people that I worked with wanted to invest in me so I started a company that built a piece of software called Kavita. Kavita in Japanese just means festival of gods, but Kavita was a fully immersive online social networking service that was written in Java 1.0. So thank you, James Gosling.

That was a really fun experience. It didn't really go very far. We sort of sold the IP and sold the company and I made a tiny little bit of money, enough to buy a house. But yeah, those were my first two startup experiences. I went to two failed startups thereafter. So one was I think what we would now call a traditional web developer where I was an IC working on a number of different things.

The second was a company called Silver Cube, where my title was technically chief scientist because we really sort of leaned into the whole science and sort of scientific revolution, even though we were doing engineering. Sort of the theme. Though my title was Chief Scientist, I was actually CTO of that company, so those were my experiences of my early career. Then I went through a number of, I think, growth spurts and learned how to work at a really big company like Volkswagen, 300 some odd thousand people, and a really old and story, but an extremely popular company like Nintendo. Just really learning how to become a better version of the leader which led me to where I am today.

Can you tell us a little bit more about TaxBit?

So TaxBit is this ecosystem of what people sort of colloquially know as cryptocurrencies. We don't mint cryptocurrencies or do any sort of on-chain work. We don't airdrop NFTs or do anything of that sort. Our mission is to unlock the power of digital assets to help support the broadening of growth of the ecosystem and of the economy and of positive outcomes for people who would want to participate in that asset class. We do that through earning trust. The way that we've defined trust is by regulatory compliance. Our perspective is the only way that intangible assets as a class of which cryptocurrencies are a subset of that class will be successful is if users like you or anyone that you might know who's investing in the asset class have that trust.

So that means knowing your customer or what the industry calls KYC. That means making sure we adhere to anti-money laundering rules, AML. That means paying your taxes and making sure that if you're an industry participant and you have cryptocurrencies on your books you're able to do proper accounting, be that gap based or whatever the type of accounting system or scaffolding that you have in place, that you're able to acknowledge those things on your books, and again, pay your tax remittance accordingly. That's our core competency. Business has been very good actually because a lot of institutional investors completely agree with us that in order for this ecosystem to grow and to be successful, trust has to be earned.

Where is the company today — employees, a funding round, market challenges, however you want to define it.

We are a series B-funded startup. We have a $1.33 billion valuation after our last funding round. We have a positive balance sheet. We're 250 employees and are growing rapidly. We are in Seattle, Draper, Utah, more or less Salt Lake City, Utah, San Francisco, and Washington, DC. I even have a couple of folks in New York, but we haven't officially opened an office in New York yet. We are growing and have many challenges ahead of us. I would say the upside is looking extremely positive, even with the current macroeconomic environment that we're going into, be it recessionary or hyperinflation, or stagflation. We'll see in the next few months where we actually land, at least within this country.

But we know that regardless of what happens with the macroenvironment, the asset class is still, the participation class, is going to exceed expectations. And because we're a picks and shovels business — that is that whether you have a gain or a loss — you are still going to have some taxable obligation. That could be tax loss harvesting or that could be some sort of remittance because you did have a gain in spite of what's happening, again, with the macro environment, you're still going to need us. And so again, it's been really good.

Thanks for that context. How did you come to the role?

Yeah, I wasn't looking. I was at Stripe, a great company and I think doing pretty impactful work and really enjoying myself. I had, speaking of trust, earned the trust of a lot of people in that organization. And Stripe is a great environment in that it's an extremely rigorous environment. I mean, I don't know. I have no idea how I got hired there. Just person after person, extremely intelligent, extremely well read. Polyglots. They talk about math, talk about science, talk about arts, talk about literature. You could have a really compelling discussion with just about anyone in the building or buildings. I saw myself just maybe getting old there and trying different things and investing in different opportunities.

An executive recruiter reached out as had many. Usually, what would happen I'd say, yeah, that doesn't sound that interesting thanks for considering me. Or I would say, okay, fine, I'll have a conversation. Even when I would have a conversation, I would only use those conversations for calibration. It's like, do I still feel like I'm marketable? Do I still feel like I'm fairly compensated? All of those questions were typically answered in the positive, but the most important question was, do I still feel like I have an opportunity to make an outsize impact with the investment that I'm putting into what I'm doing it?

I did pretty much feel like that answer was always yes with Stripe, but here came an opportunity where similarly, I felt like if I were to invest in this opportunity, I could have an outsized impact. I started thinking more about it. Who I am and how I show up and what I look like, quite frankly, and what I represent as a summation of all those things. And when considering that, I couldn't turn the opportunity down. To be clear, they made it worth my while.

I totally get that. I know you were happy at Stripe but was being a CTO something you thought you might do again?

I thought eventually, I didn't really have a timeline in mind because I knew that for sure I could always go to a smaller company or a startup and likely be VP or CTO. Indeed those were typically the types of opportunities that would come to me. There might be the occasional hyperscaler that would come and say, oh, come be a senior manager. You know, like classically the Amazon outreach is always that. Amazon never reaches out unless you're the CTO of a gigantic company, then maybe they'll ask you if you want to be a director. But the typical outreach by and large was that. So I knew there was a possibility and it was really about when I wanted to take that opportunity. But to your point again, I was super satisfied and fulfilled at Stripe.

I loved the people that I worked with. I still care deeply about those people. I still get notes and messages from those people. I have to sort of put up a wall because I have a non-solicitation for about nine more months. I still have strong connections to that organization. I'm still an investor and an owner in that organization I want it to be extremely successful, but, and this is critical…I also am an investor in myself, in my family, and those opportunities that I can invest in to see more positive outcomes for my community and other things that I care about in addition to Stripe. So I decided to invest in myself.

Can you tell us more about what you considered when thinking about leaving Stripe and taking this role?

Yeah. I think it's an important point and that'd be very sort of deliberate about what I mean here is that I grew up in southeastern Michigan in Detroit and I am, and I remain and I will always be a Black male. When you think about our industry, I mean, it's one of the memes in our industry is that you just don't see a lot of people that look like me. Let's just be clear about that. Like, period, you don't see a lot of people that like me. Certainly, when you look at leadership and even more so when you look at the C level or the executive suite, you don't see us in tech. I don't care if you're a FinTech if you are med tech or any type of tech, just tech period, people from underrepresented backgrounds and certainly people of color and certainly Black people as a subset of those.

I had a lot of introspection about how important it is to see people who look like me, who are capable. I felt completely capable of doing the role, not that I was an expert or that I would be the world's greatest, but I was definitely someone that could do the job and be impactful. I think that all of that, again intersectionally, is important to people who are aspiring to do those sorts of roles, executive leadership within tech. They need models to say, oh yeah, it is indeed possible. 

Now, am I a role model? Am I a model that someone should follow or a template for someone else who might be coming near me or far after me? That I don't know. I mean, time will tell. But I do see a responsibility and I see the importance of showing up while of course, doing justice to the people who have invested in me and have trusted me with this role. So first and foremost, TaxBit, make sure that this is as successful an endeavor as it possibly can be. Also, I want to be within this industry, someone that people look up to and say, yes, that's a person that has figured out how to do tech leadership some semblance of the right way. That's a person that I aspire to model some parts of my career after. And yes, that's a person that I want to have a conversation with so that we can share knowledge and both grow and learn together. I see that responsibility on me is to be investing back in my community and my practice. I do believe that we engage in a practice that it's important to contribute back to to make sure that the practice becomes stronger and a better version of what it had been as it goes into the future.

Did you feel that sense of responsibility or modeling earlier or was this a new priority or awareness?

When I first took on leadership I probably was not a very good people manager. I was probably a very good engineer. At least that's what I tell myself. The story I tell myself in my head is that I'm a pretty good engineer, but was I a good leader? I am pretty sure the answer to that would be fairly solid no. I then knew that I wanted to invest in being better at that practice. So whenever there was a leadership development program or some sort of thing that I could go and get feedback and do some introspection. I learned that the art and science of introspection are really important in leadership roles.

That was something that I definitely invested in. There were tons of sort of canonical texts. I have a bookshelf that you can't see on the camera, but off to my left here, there are a ton of engineering design books that are about the practice and the science and art of software engineering. But there are also a lot of books on leadership and there is a leadership book that's called the Leadership Challenge. It's a pretty well-known book, but one of the things in that book that I took as a lesson early on, and I continue to proffer as advice to anyone that asked is that leaders model the way. That the way to show up and to be a resonant leader is to as we say again, colloquially is to walk the talk. Do what you say is the thing that you would want people to do, or better said, if you have a set of principles that you would adhere to, some guardrails that sort of help you understand what the trade-offs are, you're going to make, or make decisions in tough times, or do tie breaks whenever you need to, that those things are the things that you don't just say are the right things to do, but that you show up and you explicitly in your actions so that this is the way to comport yourself. Hopefully, there is a positive thing that resonates with folks and that they can in their own way mimic or copy.

I love that. I’ve not read that book but love that idea. I think about it as modeling what you want to see in the world and knowing your guiding principles.

That's right.

I also understand that as CTO you also oversee the people team. I don't know if I’ve seen it before? How did that come about?

You know, if you've seen it before, I would love a model. (laughs) I'll talk about what happened and how it happened, but then I'll talk about what it means and what it means for me. When I joined TaxBit, one of the critical things was that and this is true for every startup, especially startups in tech, but everyone knows that the two most important things are people and money, right? You got to have investment so that you can spend your capital in order to invest in the business and do whatever it is that you're intending to do. The way that you can express that most impactfully, but also you need people in order to deliver on this because no one can do any of this on their own.

TaxBit is operating in an ecosystem that there are a lot of strong opinions about, and I'm sure anyone listening and watching knows broadly about those opinions, but briefly within the crypto ecosystem, if you're talking about a blockchain, that is proof of word, blockchain, the amount of energy, that proof of word blockchain famously Bitcoin utilize is on the order of about the same amount that a small country utilizes just to solve these really hard math problems in order to order the blocks and then ascribe those blocks to the blockchain in order to create these immutable ledgers as the story goes.

There are friends of mine that I have that are adamant that it is the worst thing ever, like should just not exist as a practice. Then there are people who believe it's the future of finance, that it is the future of freedom of exchange of value and prosperity. The underbanked and unbanked will finally have a way to freely participate in this now so-called digital future or the future of whatever the economy is going to become. And my perspective is that extremes are really hard to navigate and reason about. What's probably true is that there's a little bit of truth in both of those. That the intelligent thing to do is to figure out how to avoid a lot of the bad things and to make sure as much of the good things can happen and be facilitated as possible.

You can't do that by ignoring the ecosystem. You can only do that by being a participant. And so that's what I've chosen to do. So to the question, I think when I joined TaxBit, we were looking at the types of folks that were already in the organization and what we needed in order to be successful with this endeavor, which is a pretty audacious goal and a pretty ambitious endeavor. We know for a fact that we can't do it without builders, and we need the very best builders that we can find. Quite frankly, we weren't moving as quickly as we needed to on recruiting and building an engineering brand, a lot of the things that helps an organization hydrate with the very best people that it and to make sure that those people can do the very best work of their careers, which are principles that we hold.

I brought this up early in my tenure and the other leaders within the organization said, “Okay, well, why don't you just take people in culture and see if you can accelerate some of those objectives?” And I said, “Wait, that's not what my point was.” But then I thought about it and I said, “Okay, I'll take it on. Why not?” This is a startup.

I came to the organization to do impactful work. If doing impactful work also means stepping a little bit out of my comfort zone, which I think every leader should do to be comfortably uncomfortable, I’ll take this one and learn as much as I need because I know I’m going to need to learn a lot. 

I will also keep that objective in mind of hydrating these teams with the very best talent that we can find and making sure that those people can do the very best work of their careers. So what it means to me is that in addition to being the CTO, I also call myself the CRO, the chief recruiting officer. I spend an inordinate number of hours, and a lot of CTOs say this, but I truly live it that I am recruiting all the time. I’m having coffee chats, sales calls on interviews, pinging people randomly on LinkedIn or Twitter, or all the spaces. I get a thrill out of that because I'm also a bit of an extrovert and I like meeting people in general. So it's a good fit. And it allows me to really lean in some muscles that I've already been building over time anyway.

I'm excited about this experiment and what you're discovering. It makes sense because engineering typically has the most staff in a tech startup.

Yeah, engineering's almost 50% of the company.

Yeah, that makes sense. I want to go back to what we were talking about earlier, which is being an underrepresented voice in the CTO chair. What’s that been like?

I would say as CTO, what's interesting is that my entire sort of first-degree network connection, so the board, the people who are also on the leadership team C level and director, plus people who are within my pillars and reporting up through me, everyone has been extremely supportive. I feel like my voice is not only heard but that it's very important. It's one that resonates. That’s something that I'm really thankful that I've been able to early on I think establish again, a semblance of trust and credibility within the organization. I do think that there are very real systemic issues that exist outside of TaxBit. Outside of, name the ecosystem or name the bounding constraint and those things are very apparent to me every single day.

I wouldn't say that I've experienced anything overt, thankfully. I live in Seattle, which is some people say performatively progressive, but it is progressive. All of my neighbors who are white, all have Black Lives Matter signs on their windows and in their yards. So at least I know my life matters, but I think that the fact is that there are still those systemic issues that, even if I'm not experiencing them directly firsthand myself, there are those around me or those who might be several degrees removed from direct connection with me that might have unconscious biases. When I walk into a room does everybody expect that I'm the CTO unless I'm an invited speaker? I don't know. Probably not I would guess. I would imagine that I would probably be more right about that than I am wrong on most occasions, even in a progressive city, like Seattle or sometimes a progressive city like San Francisco, but I still feel quite confident that whatever sort of friction I might experience, either now or in the near future, that I can be extremely resilient to that.

As we started our conversation with, I think where I grew up and the foundation that I had there has made me, I had that true grit and extreme resilience and ability to manage and navigate those situations quite comfortably. In most cases, even before I was a CTO of anything, if there was any semblance of that, I've always seen it as my opportunity to educate. Not that it's my responsibility, but it is my opportunity whenever something strange or on tour happens because of creed, culture, or race to be able to say, hey, I understand that's your perspective, but that's a learned behavior. That's not the truth of the situation. Here's the truth. Let's talk about that. We could either come to some mutual understanding or we can agree to disagree, but we can at least have the conversation.

That's so great. I think you talked a little bit about this, but can you say more about some of the opportunities of being an underrepresented voice in the CTO chair?

I think as I look to the future, I don't know what's going to happen with our organization, with our company, but I have, I'm bullish on our prospects. And I think that we'll do quite well. I have a friend Laura Butler who was a CVP at Microsoft and CVP of notes for quite a while and a distinguished engineer. I think the first female distinguished engineer at Microsoft. She's now doing a startup herself, but Laura talks a lot about this notion of civilizations. She says the right thing to do as a leader is to endeavor to create a civilization that endures beyond you.

When you think about it, you think about the analogy. Electric, power, waterworks, the library, schools, highways, roads, those things, no one person creates. It's a community coming together. It's an investment, it's really an amalgam of consciousness and a culture and a collective of people coming together to build something that makes their community better. And I look at the opportunity for scaled or rapidly scaling startups and companies in general to do that. If you're going to look inward and talk about the things that you can do to make your community better and to build some artifice of your culture and some extension of your principles to make the things around you better, then perhaps aspirationally, you can create something. Similarly, I think we often hear about people talking about their legacy, but they talk about legacy and the context, many occasions of a product, some wonderful product that they did that sort of changed the world. Like, I created the iPhone.

If you can be a person that said, “Well, I made it easier for underrepresented voices and people to be accepted and acceptable in these seats of leadership and executive execution.” Well, that's a pretty damn good thing. So I endeavored to have the opportunity to lean into that. I know there’s a lot more work to do, but I'm up to that challenge.

That's wonderful. It's such a great distinction between how we think about legacy often as this thing we created versus opening the door to leadership for others. Helping us see leadership differently so that we have all sorts of people in leadership.

That's right. That's absolutely right.

If you could go back and give your pre-leader self advice — I know that would be a ways back because you've been in leadership for a while — what would that be?

I would have so much advice for my, my younger self. I actually asked this question of candidates quite frequently. And it's again, an opportunity to gain signal on how much candidates invest in their own introspection. I just had a conversation with the CTO of Circle CI about failure and learning from failure. I think I've failed a lot. You know, I dropped out of Penn for instance, that was one of the things. If I could go back in time, I might give myself the advice to just stay in school for that first iteration and finish out, I eventually did go back and finish school and went to grad school and even started a Ph.D., but went ABD (all but dissertation). But I also kind of enjoy my life and the way it ended up.

I think a lot of the choices quite critically have led me to this current point. And maybe I would've ended up on a different path and a different, who knows where because of all of the different cascading and inflections, but I do, I think directly and deliberately see education as the most powerful thing. No matter what anyone does to you, no matter what they take away from you, they can take away a lot, right? No one can take away what you've learned. You always hold that's yours.

I've had the benefit, the blessing, whatever you want to call it, of being self-motivated to learn. So even if I'm not institutionally being foisted into an area where I have to learn something, because an exam is coming up, I've still been a voracious reader and consumer of information. And that's truly helped me. And I think, again, if I'm going to go back to my younger self, I would say definitely needing into that and keep doing that, do that even more than you're already interested in doing. Be even more sort of aggressively interested and ambitious about learning about different cultures and different people and different languages. That's just going to make you a better human. And that's probably where I would start.

That’s great advice. Is there anything that we haven't covered about your journey that’s important?

One thing that's really important to me is my two little girls, Isabella and Zoe. They are five and two in kind, the most important thing in my life.

When I think about what I do, how I do it, why I do it, and what I aspire to do, I always center my context on creating better outcomes for the two of them. If you were going, to sum up sort of my perspective on what's important to me and why the things that are important to me are? It's because of those two voices that I hear in my head all the time and that I want them to be able to do in this world as two little Black girls who are going to grow up in a different context than I did.

My family wasn't rich, we were comfortable. And maybe I was like extremely lucky and had a little bit of talent to help support that luck that drove me in this direction. That ended me in this role here. But I want them to have, quite frankly, an easier time of it. I want their struggles to be struggles of opportunity, like, which of these great opportunities am I going to take advantage of? 

(I’m so touched by Tramale’s why that I’ve grabbed a tissue and am dabbing my eyes)