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-2014-21

More from CoinTracker

• For a 10% discount for new CoinTracker users go to: https://cointracker.io/a/boring
• Interested in working for CoinTracker? They're hiring across the board: https://www.cointracker.io/about

Transcript

Will: 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...

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.

In this episode, we cover:

00:00:00 - Reflections on the Episode/Introduction

00:03:06 - Steve’s Bio

00:07:30 - The 5 W’s of Servers and their Future

00:14:00 - Hardware and Software

00:21:00 - Oxide Computer

00:30:00 - Investing in Oxide and the Public Cloud

00:36:20 - Oxide’s Offerings to Customers

00:43:30 - Continious Improvement

00:49:00 - Oxide’s Future and Outro

Links:

• Oxide Computer: https://oxide.computer
• Perfectlyboring.com: https://perfectlyboring.com

Transcript

Jason: 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 runnin...

In this episode, we cover:

• 00:00:00 - Introduction
• 00:02:20 - “B’s” Background and the Beginning of Axle Payments
• 00:06:40 - Why Transportation and Freight
• 00:17:00 - The Details and Risks of Working with the Industry
• 00:22:45 - Client Changes from Working with Axle Payments
• 00:28:30 - Axle Payments’ Future
• 00:33:15 - How Axle Payments Makes Money
• 00:35:50 - The Supply Chain Crisis
• 00:39:00 - The Future of the Industry

Links:

• Axle Payments: https://www.axlepayments.com

Transcript

Will: 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 wi...

In this episode, we cover:

• 00:00:00 - Reflections on the Episode
• 00:03:15 - What is Mortgage Servicing
• 00:13:20 - Impact of the Great Financial Crisis
• 00:18:40 - Andrew’s Background
• 00:24:10 - Valon’s Technological Innovations
• 00:31:06 - Relationship with the Consumer
• 00:36:00 - Regulations and Regulators
• 00:40:40 - Valon’s Future/Outro

Links:

• Website: Valon

Transcript

Jason: 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 structure...