Perfectly Boring

In this episode, we cover:Introduction (00:00)Chandan’s background and building CoinTracker (02:26)The tipping point into crypto and tax compliance (06:14)Trials and tribulations of committing to crypto (11:30)Thoughts on expanding into enterprise (14:00)Reflections on recent tax regulation and some expected shifts (18:42)Expanding the relationship with the consumer (21:30)Working in the ecosystems of integrations (24:38)Where CoinTracker is headed (29:00)Links:CoinTracker: https://www.cointracker.io/First tax guidance that the IRS released: https://www.irs.gov/irb/2014-16_IRB#NOT-2014-21More from CoinTrackerFor a 10% discount for new CoinTracker users go to: https://cointracker.io/a/boringInterested in working for CoinTracker? They're hiring across the board: https://www.cointracker.io/aboutTranscriptWill: Welcome to the Perfectly Boring podcast, a show where we talk to the people transforming the world’s most boring industries.Jason: I’m Jason Black, general partner at RRE ventures.Will: And I’m Will Coffield, general partner at Riot Ventures.Jason: And today we’re talking to the co-founder and president of CoinTracker, Chandan Lodha. Chandan is actually a classmate of mine in school and has since built, now, a unicorn business in the crypto tax space called CoinTracker. Not my first time talking to Chandan about the business, but maybe, Will, what were your impressions after our conversation?Will: Yeah, I was really impressed with, I think, the simplicity of the value proposition for CoinTracker. Which is—Jason, as you highlighted in the podcast, it’s sort of death and taxes. And they found a kind of ubiquitous pain point that everybody participating in the crypto space feels around needing to become tax compliant at a certain point, and how they not only solve that problem but then think about it not as the finite value proposition, but as the beginning of what will be a sort of ubiquitous relationship with the consumer, and how to be a partner for them as they go deeper in their crypto portfolio and life.Jason: Yeah. And matching the increasingly complex landscape of crypto with an increasingly, kind of, simplified, approachable version that is within the confines of taxable events, et cetera, that brings that kind of trust all the way back.Will: Yeah, I mean, the landscape of integrations and assets that they have to get their arms around is not static. It is—Jason: It is not.Will: —[laugh] it is not static at all. And just really impressive what they’ve built over a relatively short period of time while also being founded in the midst of a bull market in 2017, building through the course of crypto winter, and now positioning themselves as you know, one of the category-defining platforms as we kind of go into another major building cycle for crypto.Jason: Yeah. Well, before we get too deep, let’s jump into the interview.Will: Welcome to Perfectly Boring. Today, we’re joined by Chandan Lodha who is the president and co-founder of CoinTracker. And today, we’re going to be going on a deep dive into the very esoteric and complex world of taxes as it relates to the explosion in activity that is happening in Web3 and crypto trading. Chandan, thank you for joining us today, and we’d love to start by giving the audience a little bit of a background into your career and how you kind of ended up at this place and building what you’re working on.Chandan: Absolutely. Thanks for having me. So, my background is mostly in the tech space. I was a product manager by training; I worked at Google for a couple of years. And basically ended up getting more interested in FinTech.And so my co-founder and I—my co-founder, John who’s also from Google—basically ended up starting building in the FinTech space. And it was actually building on traditional financial rails, like, automated clearing house ACH and SWIFT network that was super slow, super inefficient, didn’t work in a, kind of, internet-enabled digital way. That led us to be frustrated and diving deeper into the crypto space.Will: Awesome.Jason: And what in particular about the, kind of, tax angle was interesting to you? And give us—I mean, obviously crypto is moving so quickly, has been kind of accelerating, certainly recently, but it’s gone through these waves. It’s kind of important to know what the timing is and where that entry point was. So, maybe you can give us a little bit of sense of timing there, too.Chandan: Right. So, we started working on this in 2017, kind of mid-2017. And what was happening was we were building a personal financial assistant type of app that would help people save money, build wealth, kind of automate financial assistance. And like I was saying, it was really frustrating to work on ACH and SWIFT network. And the reason why is it would take 11 days for our first settlement between a checking and savings account bank transfer, with a $1 fee on a $5 transfer. So, it was slow, it was inefficient, it was expensive, it didn’t work on weekends, it didn’t work on holidays, it was not a 24/7, 365 system.And at around the same time, people were getting super hyped around cryptocurrency, right? This was leading up to one of the biggest bull runs at the time. And so we kind of got curious. We were pretty skeptical at first, to be completely honest, but we kind of dove in a little deeper. Like, what are the fundamentals here behind bitcoin and why is there so much hype here?And what we ended up finding out was, it was a digital-native, global financial system that could be built using this technology. So, that got us, kind of, intrigued from a technological perspective. And next thing you know, I had an Ethereum miner that we built in the office, I was running a Monero full node on my computer, I had 15 different cryptocurrency exchange accounts, it was just super wild. And as a result—Jason: Yeah, it’s immediately going down the rabbit hole in crypto.Chandan: Down the rabbit hole. Exactly. Down the rabbit hole. And as any, sort of, early crypto person can tell you, the next thing you’re trying to do is keep track of all your transactions and wallets and addresses. So, we had a complicated spreadsheet doing that.And then we had formulas pulling in price feeds, and then we had Google Apps Scripts. And it was two minutes to open the Google spreadsheet, so we basically built a very, very simple landing page that only allowed people to track their cryptocurrency portfolio. And it was just—it was a solution for ourselves. We ourselves were like, “We need this.” So, we built that.And we kind of knew we were onto something because immediately random people from around the world, people in Thailand, were emailing us saying, “This sucks and you need more features.” And we were like, “Wow, [laugh]. This random person in Thailand is emailing us complaining that our tool isn’t good enough. That means we’re onto something. W...

In this episode, we cover:00:00:00 - Introduction 00:02:20 - “B’s” Background and the Beginning of Axle Payments00:06:40 - Why Transportation and Freight00:17:00 - The Details and Risks of Working with the Industry 00:22:45 - Client Changes from Working with Axle Payments00:28:30 - Axle Payments’ Future  00:33:15 - How Axle Payments Makes Money00:35:50 - The Supply Chain Crisis  00:39:00 - The Future of the IndustryLinks:Axle Payments: https://www.axlepayments.comTranscriptWill: Welcome to Perfectly Boring. I am Will Coffield from Riot Ventures.Jason: And I’m Jason Black from RRE Ventures.Will: And today on the podcast, we’ve got Bharath Krishnamoorthy, who is the founder and CEO of Axle Payments. And Bharath is joining us today to talk about the unbelievably boring and strange world of freight intermediaries and invoice factoring. Jason, this is a business you know pretty well—have known Bharath for a couple of years—but this was a really interesting discussion. You know, like, what were some of the key takeaways that you had from our discussion with [B 00:00:37]?Jason: Yeah, I think this is another classic case of an under-digitized industry that runs the world, right? It’s a multi-trillion dollar industry that’s run on paper, fax, Excel, phone calls, and human relationships. And you’ve got these freight intermediaries that actually benefit from all those relationships, those things are actually fantastic. That’s what they want to be focusing their time on that allows them to offer great services to their customers, but we’ve got a new kind of class of tech companies coming in that are offering new financial services that allow for, kind of, QuickPay and faster payments in the industry. And that’s a benefit to everybody involved, but the incumbents have a difficult time actually meeting those new demands of the market.And I think what B has built with Axle Payments is a way for that industry to focus on what they’re best at, which I think is what we want to see technology and financial services do. So, I thought it was a fantastic discussion. And before we get too deep into the weeds, let’s kick off the interview with B.Will: All right everybody, we are joined today by Bharath Krishnamoorthy, who is the founder and CEO of Axle Payments. Bharath, thanks for joining us today.Bharath: Yeah, thank you for having me, Will.Will: So, that I don’t botch this going forward, Bharath actually goes by B. So, B, appreciate you being with us today. And I think maybe as kind of a way of kicking off the podcast, what we’ve been kind of doing throughout the first couple of episodes is having the founder give a little bit of a background just on, sort of, themselves personally, kind of your personal and professional background that ultimately led you to founding Axle Pay, and then we’ll kind of dive into the business from there.Bharath: Sure. Sounds good. So, my personal background, I grew up in New Jersey, moved to Virginia in high school with my family, studied economics at JMU in Virginia, and then moved to New York for law school. So, graduated from Columbia Law School, practiced as an attorney here in New York, doing M&A and private equity work, which is about as fun as it sounds.And sort of parallel with this, my co-founder, Shawn, who’s my high school best friend, had taken a slightly different path. So, you know, he went to UVA for school and then started working in the FinTech space, a couple of different FinTech startups of varying sizes. And throughout this, we’d started a bunch of small businesses together. Those have been the projects where I’d felt the most energized and the most excited to actually do work. It seems sort of obvious to me, and I think to him as well, that down the road, that’s what we ultimately wanted to do, right, was to build something really dope together, something big enough that it could be our full time jobs, right, where we could quit our jobs and just work on something awesome together.And the obvious difficult question was, you know, what are we going to build? So, in 2017 when I was working as a lawyer and Shawn was working at this tech startup in DC, we were taking these buses back and forth to visit each other all the time. Probably you know Greyhound, Megabus, you may or may not know that there’s, like, a dozen other smaller regional operators that all kind of operate similarly in the same areas. And we realized that these companies are just, they’re kind of like airlines in terms of their business model, but just way lower tech. And so we came up with this idea to build a revenue optimization solution for them that would basically help them with their pricing and scheduling in order to maximize the money they earned.Started working on that; we have to quit our jobs, incorporated the company. We got a few customers within, I think, about six months, we were doing about 100 grand in annualized revenue. So, it was, you know, it was working a little bit. And what we realized is it wasn’t going to work much more than that because the market in the US was just very small, right, that if we totally knocked it out of the park and did everything right, maybe we get to a million dollars a year, which sounds like a lot of money, but really isn’t that much if you’re banking on everything going perfectly.So, that started this process of us really taking a step back and trying to find a better opportunity. And we basically just, like, pivoted over and over again over the course of two years to various opportunities in the transportation space. Eventually we came up with this framework, right, that whatever we decided to do had to meet three criteria: it should be something that we thought we had a relative advantage at given our backgrounds, it should be something that we cared about solving, right, so a problem that we would feel good about working on today, tomorrow, and in ten years; and it should be a really attractive business opportunity. And it’s pretty difficult to find something that satisfies all three of those.Where we eventually found some traction was in the world of freight finance. And we found this problem which, at a high level, was solving cashflow problems for small logistics businesses. And it struck all three chords, right? It was at the intersection of transportation and finance. By this point, we had a lot of exposure and a lot of relationships in the transportation industry, and both of our professional backgrounds very closely tied to the financial world.Second, it was a pain point we cared about, right? It’s not that we were coming from a long line of truckers or had some extensive background in the logistics industry, but we were small business owners, and we know that for small business owners, cashflow problems are often the most salient problems they face. And so the idea of solving that problem for thousands of companies was just very compelling for us. The first client we closed literally had his COO recording him signing the contract because it was such a life-changing experience for him. And I was like, “Man, if we can just do that again, I’m going to feel really, really happy.”And then the third is that it was, it’s kind of a no-brainer business opportunity,...

In this episode, we cover:00:00:00 - Reflections on the Episode00:03:15 - What is Mortgage Servicing00:13:20 - Impact of the Great Financial Crisis 00:18:40 - Andrew’s Background00:24:10 - Valon’s Technological Innovations 00:31:06 - Relationship with the Consumer 00:36:00 - Regulations and Regulators 00:40:40 - Valon’s Future/OutroLinks:Website: ValonTranscriptJason: Welcome to the Perfectly Boring podcast. Today we have Andrew Wang, CEO of Valon, on the show, and today we’re taking on the topic of mortgage servicing. So quickly, what is mortgage servicing?Well, a mortgage is obviously a loan for a home. And mortgage servicing is the institutions that actually take care of paying off that loan over the 10-, 20-, 30-year timeline. So, that digital interface where you pay your bill, et cetera, that is not always your originating bank. And Andrew is building a fascinating business in this space. We learned a lot about the mortgage, the evolution of the mortgage servicing space over time, the impact of the great financial crisis, and the interesting approach Valon is taken, not only just with technology, but changing the relationship with the end customer. So, what were some of the interesting touch points that we got during the conversation, Will?Will: It was a really wild discussion because I started with a fairly preliminary understanding of what mortgage servicing was. And in part of the wind up that listeners are going to get an opportunity to hear, Andrew really gives us a perspective as to how critical mortgage servicing is to the underlying health of the US, and therefore global, economy, and how much of an afterthought mortgage servicing has historically been, and why that should not necessarily be the case, and why now is the, sort of, unique moment in time to be able to use advanced technology and a reorganization of the overall stack for mortgage servicing to bring a better product to market for both consumers, for originators, for investors, and for regulators. And so, I mean, really badass discussion, really cool company, a space most people never think about, definitely a boring space, but with a just immense amount of value to be created.Jason: Yeah, and hopefully our listeners go through kind of the same increase in excitement that I had during the conversation, which is you kind of over time just realize this entire industry of mortgage servicing, not only is it critical, but how much they’re missing the actual point which is, if you really just focus on the homeowner and creating a great experience for them, this is a huge relationship, it’s a multi-decade relationship, and there’s probably not just one product you can offer them. But they’re stuck in the staid and stodgy technology of yore, and haven’t been able to move as quickly and break through to open that aperture and open that relationship with their customer. So, before we get too deep into the weeds, let’s just jump into the interview. Here’s Andrew.Will: Andrew Wang, founder and CEO of Valon, thank you for being on the podcast with us today to talk about the very boring, very large industry of mortgage servicing. For the benefit of our listeners, it would be good to start at a really high level and give people kind of a baseline for what mortgage servicing is, and maybe a little just on the history of the mortgage servicing industry, you know, before we dive in a little bit on the specifics of your background and Valon.Andrew: So, mortgage servicing is a sort of pervasive thing that exists throughout the mortgage ecosystem and in the lives of most American homeowners, but it is also just not very well understood in terms of the dynamics that are involved with mortgage servicing in terms of who’s involved, how they’re involved, and exactly what they do. But again, nonetheless, it’s something where it’s within every part of the mortgage ecosystem today. But to give you some background on mortgages and how mortgage servicing even is a real thing, let me first talk about the mortgage industry as a whole. When you think about the mortgage industry, it’s obviously a very large component of the American economy today. When people look at it, they say, “Hey, 20% of GDP in terms of housing,” something that the US government often uses in order to boost spending; they lower our mortgage rates in order to cause people to have more savings and then spend on other things. It’s just a very, very core piece of the American ecosystem.But it actually came into play really, during the depression, the Great Depression, were effectively pre the Great Depression, mortgages weren’t really regulated all that much, and as a result, there were kind of weird, funky structures, even crazier than what people saw in 2007. And as a result of that and as a result of all these people who weren’t able to pay their mortgages due to these balloon loans being in place, which are basically loans that don’t amortize, and basically become due and payable at a certain point in time, what the US government did as a function of the New Deal was put these government institutions into place to create more affordable housing structures, to create these institutions who would really regulate the housing market, or really add liquidity into the housing market so Americans could actually own a home.Will: And that kicked off the current, almost philosophical ideal that we have today about homeownership kind of being the epitome of the American dream. This was—the mortgage was almost an invention to bring that to fruition after World War Two?Andrew: That’s exactly right. So, after World War Two, it became more and more core to the American dream. When everybody talks about, “Hey, what is the American dream?” It’s obviously being able to get further in life based on your own merits, it’s about owning a home, and starting a family, building a community, all of those different things, and the home is just so central to that dream. But exactly to your point, it started from post-World War Two.By the 1990s, it became such a large component of how the US economy even functioned and worked that there was more and more so this focus on affordable housing, putting people in homes, putting people in sort of a structure that creates the ability, creates stronger communities, and create a more robust ecosystem within cities, within neighborhoods, and everything else. So, that’s how mortgages became so intertwined in the American system versus, you know, other countries, which may have relatively high homeownership rates, but just not nearly as high as the United States. That’s, like, the genesis of how mortgages became a big component of it. The mortgage servicing aspect of it actually wasn’t as relevant of a thing, that became more of a thing, actually, after the great financial crisis, the GFC. So pre-2008, what ended up happening was actually that most people when they got a mortgage were serviced by the same people who gave them that mortgage. So, you had Countrywide, you had some of these older institutions which have since gone bankrupt or have been acquired by more older financial institutions, servicing the mortgages. So, it wasn’t really a separate thing, for the most part, at that point in time, and it wasn’t really an important topic, actually.Jason: Before we go too deep, maybe you can define servicing. Like, how does that show up in the average Amer...

In this episode, we cover:00:00:00 - Reflections on the Episode/Introduction 00:03:06 - Steve’s Bio00:07:30 - The 5 W’s of Servers and their Future00:14:00 - Hardware and Software00:21:00 - Oxide Computer 00:30:00 - Investing in Oxide and the Public Cloud00:36:20 - Oxide’s Offerings to Customers 00:43:30 - Continious Improvement00:49:00 - Oxide’s Future and OutroLinks:Oxide Computer: https://oxide.computerPerfectlyboring.com: https://perfectlyboring.comTranscriptJason: Welcome to the Perfectly Boring podcast, a show where we talk to the people transforming the world’s most boring industries. I’m Jason Black, general partner at RRE ventures.Will: And I’m Will Coffield, general partner at Riot Ventures.Jason: Today’s boring topic of the day: servers.Will: Today, we’ve got Steve Tuck, the co-founder and CEO of Oxide Computer, on the podcast. Oxide is on a mission to fundamentally transform the private cloud and on-premise data center so that companies that are not Google, or Microsoft, or Amazon can have hyper scalable, ultra performant infrastructure at their beck and call. I’ve been an investor in the company for the last two or three years at this point, but Jason, this is your first time hearing the story from Steve and really going deep on Oxide’s mission and place in the market. Curious what your initial thoughts are.Jason: At first glance, Oxide feels like a faster horse approach to an industry buying cars left and right. But the shift in the cloud will add $140 billion in new spend every year over the next five years. But one of the big things that was really interesting in the conversation was that it’s actually the overarching pie that’s expanding, not just demand for cloud but at the same rate, a demand for on-premise infrastructure that’s largely been stagnant over the years. One of the interesting pivot points was when hardware and software were integrated back in the mainframe era, and then virtual machines kind of divorced hardware and software at the server level. Opening up the opportunity for a public cloud that reunified those two things where your software and hardware ran together, but the on-premises never really recaptured that software layer and have historically struggled to innovate on that domain.Will: Yeah, it’s an interesting inflection point for the enterprise, and for basically any company that is operating digitally at this point, is that you’re stuck between a rock and a hard place. You can scale infinitely on the public cloud but you make certain sacrifices from a performance security and certainly from an expense standpoint, or you can go to what is available commercially right now and you can cobble together a Frankenstein-esque solution from a bunch of legacy providers like HP, and Dell, and SolarWinds, and VMware into a MacGyvered together on-premise data center that is difficult to operate for companies where infrastructure isn’t, and they don’t want it to be, their core competency. Oxide is looking to step into that void and provide a infinitely scalable, ultra-high-performance, plug-and-play rack-scale server for everybody to be able to own and operate without needing to rent it from Google, or AWS, or Microsoft.Jason: Well, it doesn’t sound very fun, and it definitely sounds [laugh] very boring. So, before we go too deep, let’s jump into the interview with Steve.Will: Steve Tuck, founder and CEO of Oxide Computer. Thank you for joining us today.Steve: Yeah, thanks for having me. Looking forward to it.Will: And I think maybe a great way to kick things off here for listeners would be to give folks a baseline of your background, sort of your bio, leading up to founding Oxide.Steve: Sure. Born and raised in the Bay Area. Grew up in a family business that was and has been focused on heating and air conditioning over the last 100-plus years, Atlas. And went to school and then straight out of school, went into the computer space. Joined Dell computer company in 1999, which was a pretty fun and exciting time at Dell.I think that Dell had just crossed over to being the number one PC manufacturer in the US. I think number two worldwide at Compaq. Really just got to take in and appreciate the direct approach that Dell had taken in a market to stand apart, working directly with customers not pushing everything to the channel, which was customary for a lot of the PC vendors at the time. And while I was there, you had the emergence of—in the enterprise—hardware virtualization company called VMware that at the time, had a product that allowed one to drive a lot more density on their servers by way of virtualizing the hardware that people were running. And watching that become much more pervasive, and working with companies as they began to shift from single system, single app to virtualized environments.And then at the tail end, just watching large tech companies emerge and demand a lot different style computers than those that we had been customarily making at Dell. And kind of fascinated with just what these companies like Facebook, and Google, and Amazon, and others were doing to reimagine what systems needed to look like in their hyperscale environments. One of the companies that was in the tech space, Joyent, a cloud computing company, is where I went next. Was really drawn in just to velocity and the innovation that was taking place with these companies that were providing abstractions on top of hardware to make it much easier for customers to get access to the compute, and the storage, and the networking that they needed to build and deploy software. So, spent—after ten years at Dell, I was at Joyent for ten years. That is where I met my future co-founders, Bryan Cantrill who was at Joyent, and then also Jess Frazelle who we knew working closely while she was at Docker and other stops.But spent ten years as a public cloud infrastructure operator, and we built that service out to support workloads that ran the gamut from small game developers up to very large enterprises, and it was really interesting to learn about and appreciate what this infrastructure utility business looked like in public cloud. And that was also kind of where I got my first realization of just how hard it was to run large fleets of the systems that I had been responsible for providing back at Dell for ten years. We were obviously a large customer of Dell, and Supermicro, and a number of switch manufacturers. It was eye-opening just how much was lacking in the remaining software to bind together hundreds or thousands of these machines.A lot of the operational tooling that I wished had been there and how much we were living at spreadsheets to manage and organize and deploy this infrastructure. While there, also got to kind of see firsthand what happened as customers got really, really big in the public cloud. And one of those was Samsung, who was a very large AWS customer, got so large that they needed to figure out what their path on-premise would look like. And after going through the landscape of all the legacy enterprise solutions, deemed that they had to go buy a cloud company to complete that journey. And they bought Joyent. Spent three years operating the Samsung cloud, and then that brings us to two year...

Jason and Will are joined by Luke Schoenfelder, CEO of Latch, to discuss the role of Latch, and how they found innovations in something as seemingly unimportant as—locks. Luke breaks down the origin of Latch and their innovative eye for how to revolutionize a common household item. Luke and his team started with taking a look at the next steps for infrastructure, and they ended with Latch. Tune in for the full story!Luke’s upbringing in Pennsylvania set him up for a non-linear path to Latch. He has worked in a range of companies and areas of expertise, from modular housing in Haiti, to time spent at Apple. He discusses the origins of building out his team at Latch and their inspiration to focus on the hospitality industry. By going straight to the customer Latch brought in a business model innovation that set them apart, one of many that align with Latch’s vision. In this episode, we cover: Reflections on the Episode (0:50)Introduction to Luke (1:41)Latch’s Innovations (11:13)Manufacturing a Complex Product (16:52)Latch’s Lock’s Lifespan (21:28)The Experience of the Tenant (26:44)Latch’s Next Steps and Expected Complexities (29:44)Latch Lens (37:32)How Latch Makes Money (43:12)The Future (46:15)

Welcome to the Perfectly Boring Podcast, a show where we talk to the people transforming the world's most boring industries. On each podcast, we will be sitting down with executives, investors, and entrepreneurs to talk about the boring industries they operate in and the exciting businesses they’ve built. Strap in for the most marvelously mundane ride of your life.