341. Competing with a16z & Sequoia at Pre-Seed, the Evolution of Accelerators, and Deciphering Signal From Noise in Web 3 (Neha Khera)

341. Competing with a16z & Sequoia at Pre-Seed, the Evolution of Accelerators, and Deciphering Signal From Noise in Web 3 (Neha Khera)

Neha Khera of 2048 Ventures joins Nate to discuss Competing with a16z & Sequoia at Pre-Seed, the Evolution of Accelerators, and Deciphering Signal From Noise in Web 3. In this episode we cover:

  • The Case for Underdog Founders and What Creates One
  • Business Models that Lend Themselves to Becoming Platforms
  • Pros and Cons of Accelerator vs Institutional Models of Investing
  • Thoughts on the Current State of Cyber and Web 3 and Their Future

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Transcribed with AI:

Neha Khera joins us today from Toronto. Neha is a General Partner at 2048 Ventures, a pre-seed fund investing across the US and Canada. There she has led investments in Eli Health, Impacked, and Painworth to name a few. Prior to 2048, she was a Co-founder and Partner at 500 Startups Canada, Neha, welcome to the show.
Thanks for having me, Nate. Really excited to be here.
Yeah. So can you walk us through your background and your path to VC?
Yeah, absolutely. So I am an electrical engineer by background and started my career doing more traditional engineering work software design hardware design, did some work in telecommunications, but pivoted from there and sort of have always worked at the intersection of technology and business. I got into venture capital about 11 years ago, and have always worked in early stage, and have always worked in institutional funds investing across the US and Canada.
Got it. So what made you decide to join 2048? And what’s the thesis?
Yeah, great question. So 2048 was co-founded by Alex Iskold, and he started the firm in 2019. And he had a very clear passion to bring a thesis driven high conviction firm into the world of precede. I was very much operating in parallel with Alex, he was a TechStars MD for five years while I was at 500 Startups, so we were living parallel lives and both insanely passionate about early stage preseed investing. And a lot of our values just align in the sense that we want to be founder first founder friendly, always remain truly dedicated to this stage of investing, you won’t see us ever leave precede, because we’re obsessed with it. But then also coming at it with this discipline lens of being thesis driven, which is so much the opposite of what we were both doing at the accelerators. And so we really shared a common bond and aligned on all of that. And that’s sort of what made my move over to the firm. So like I said, 2048 Ventures pre-seed investor we lead or co-lead rounds. And we are a bit more of a deeper tech investor in the sense that we look for companies that are building with strong tech moats, or they have strong tech differentiation.
Definitely, how would you describe the typical archetype of founder that you invest in at 2048?
That’s an easy one, because we talk about this a lot. Uh, we definitely gravitate towards the underdog founder, the founder, who is a bit more obsessed with building their business and kind of pokes his or her head up out of the sand and goes, Oh, I guess I should go raise some capital now because things seem to be taking off. The founder who has through their experiences faced a level of adversity, which has just resulted from, you know, their upbringing, or the different paths that they taken in life, that tends to drive the majority of the kinds of foundries you’ll see us going after and investing in. And I think as a result of it, we certainly don’t have any quotas around it, I have to get the latest statistics, and I can send them to you after but I think at a high level, roughly 40% of our founders are female, and 60% male. And again, this is truly just driven by the fact that there’s a certain archetype of founder we look for and you know, women, and even people of different ethnicities and backgrounds naturally fit into what really draws us to a strong founder.
Got it. And you talked about the underdog mindset, and it’s also something that we look for here at New Stack. How do you tease that out? Is it their origin story? Or how are you able to identify the underdog mindset within a founder?
Yeah, it’s a good question. Certainly their origin story, their background, will kind of ask them a lot about their upbringing. You know, I love hearing origin stories from founders, like, where did this crazy idea come from? And you get a real sense at that point, what struggles did this founder have along the way that led them to want to solve this particular problem? I think just you know, again, being an underdog kind of lends itself naturally to this idea of fighting the fight or always going against the grain, you know, that grit, that resilience, that adversity, and those are the characteristics that we are ultimately trying to tease out in the founders. And we think being an underdog is sort of the umbrella term for it. I don’t think you really truly know until you get in the trenches with the founder. I don’t think the founders truly really know. I mean, finding a startup is insanely hard. It’s unfortunate, it’s so glamorized, but we try our best and we ask a lot of questions. In an ideal world, I wish I could spend three months with founders before writing them in check. But in today’s crazy market, it’s more like three weeks, so you know, we just try to spend as much time with them in a realy honest and authentic way to get to know who they are. Usually you can tease out elements of it for sure.
As an investor at 2048, how are you identifying sectors or trends that are worth building a knowledge base in or building a thesis around? Do you have a process that you follow? Or how would you recommend going about that to someone that is looking to develop a thesis?
Hmm, good question. I think there’s two ways to frame it. So one is going after sectors that you have an alpha in, because you know it better than a lot of other people. Maybe that’s the world you came from are worked in the other way. And the way that we think about it is what are some of the sectors that are really difficult to parse through and or understand, and how can we position ourselves in a way where we do go deep, and build a thesis around them and understand them. And as a result, build a sense of alpha, they’re happy to dive into what some of those sectors are. I mean, some of those are a bit more mainstream, like web 3 and blockchain. But then there’s certain sectors in like robotics, and logistic and cybersecurity where not a lot of investors pay attention to or focus on because it requires a really intimate knowledge and understanding of it. Health and Bio is another big one for us. Again, not a lot of investors, particularly at the pre-seed, willing to lead rounds and invest in companies at that intersection of sort of science and tech. So we look at these broad categories. And then within the categories, we think about investing in companies with specific business models and or the ability to turn into platforms. And that kind of is what makes up the core of our thesis.
How do you identify a startup in the early stages that could develop into a platform? Something that I think we hear often is companies that are building a platform out of the gate, tend to never achieve that goal. So how are you able to identify the concept? Or what is it about the startup itself, that leads you to believe that it couldn’t develop into a platform?
Yeah, we think there’s four kinds of business models that lend themselves really naturally to platforms, the obvious one being a marketplace, to your point – really hard to get off the ground, but once they do, natural platform. Verticalized SaaS is another really interesting platform. Again, you’re starting off with something where you’re wedging into an industry, maybe it’s through CRM, maybe it’s through website, but you eventually build your way through to sort of covering all aspects of that category, handling everything from CRM all the way through all the way through to payments. And, you know, turning that offering truly into a platform. The third is API’s. And then the fourth is data. So anything with a unique data set, you generally can start to build up a platform around that. So I think to your point, there’s definitely two elements when we look at a startup one is, okay, what’s the initial wedge into this market? And I think that’s just as important as the end goal, or the long term vision, which is okay, this is the initial wedge. But then what does this become in the long run? If this proves successful, and we continue to build out what are we building out towards?
Got it. So your background is really interesting, because you’ve been a partner at both a prominent accelerator at 500 Startups, but now also at 2048, a more traditional, well respected venture firm. And I’m curious, though, what was the transition like moving from 500 Startups where you are writing a higher volume of smaller checks to now being a lead investor where you’re making fewer commitments per year?
Yeah, it’s a great question. And I think, fundamentally, it comes down to two very different strategies, both of which I think, work exceptionally well at the early stage. You know, with the accelerator model, you’re playing on portfolio theory, which is build a large enough and a diversified enough portfolio, and you’re bound to have some winners in there, which absolutely holds true, I think the statistics from 500, as well as from TechStars and YC, prove that this model does work. And what I would say with the portfolio theory model is that it tends to work with a fairly high degree of consistency, so you can pretty accurately predict what your fund outcomes will look like. But I do think with this model, it tends to be a little bit harder to achieve that outlier type of return, just because you don’t own enough ownership at any one of these companies, unless you are writing a check where you’re doubling down on the winners. So that the accelerator model and with the institutional model that we’re running at 2048 Ventures again, another really great model that works that pre-seed which is buy up a little bit more ownership and concentrate your portfolio a little bit more and at 2048 Ventures we think about it more from a thesis perspective. So really dive deep into key markets and understand those key markets and have a sense of what it is you want to invest in prior to actually writing checks, and with this type of a model, it may have less certainty around what your outcomes will be. But you definitely have the ability to obtain those outliers that I talked about, because of how you’re building up your ownership strategy. So hopefully that paints a picture. But overall, two really different models, and honestly, both equally as fun and as exciting.
And for context, how many checks would you write per year at 500? And how many are you writing now at 2048?
At 2048 with our current fund, at its current size, we’ll probably write somewhere between 15 to 20 checks. And with 500 Startups we were writing – I mean, it really depends on the vehicle, but I’ll tell you about the vehicle that I was a part of, we were writing about 50 to 60 checks per year, so about tripled the amount.
Got it. Does the level of conviction change at all between getting to a yes, when you’re accepting startups into an accelerator versus leaving a deal at 2048?
It’s a good question, I think it all becomes a function of a risk. And that risk is built into the size of checks that you end up writing. So when you are writing much smaller checks into a higher degree of companies, you probably can feel comfortable investing with a lot more unknowns in place. And think about it more from the perspective of I’m constructing my portfolio, and I’m trying to diversify it with a larger check that ability to take that level of risk, obviously, lessons. And so yes, I do think the level of conviction you have deepens because you do need to spend a lot more time digging into all aspects of the company and feeling comfortable knowing that you’re investing a significant portion of your funds capital into this one entity.
For the startups that have done really well, when you take a look at your track record at 500. Is it surprising at all, which ones have done well? Like did you know that these were the stronger ones of the cohort that you’ve been investing in?
Yeah, it’s that’s a really good question. I think hindsight is always 20-20. If I think back, yes, certainly the top one to two companies, we felt more excited about them than the rest. And having that feeling when you’re making an investment through an accelerator model is rare. So it reassuring to know that that feeling that feeling did hold true. I think what was surprising is there was a really long tail of companies that we thought would do well, that didn’t. And that kind of lends itself to why this accelerator model tends to work quite well, because there’s this huge gamut of unknowns, companies that you think may not do well perform, and the ones that you think are going to be amongst the top tend to fail. So but the absolute absolute best if I think back, yes, I do think collectively as a team, we all felt really excited by them. So perhaps that feeds into your question about conviction, right? Were we able to get that from the outset?
Interesting. So what happened? Would you say with the ones you were more confident in would do well, but ended up surprising you and for whatever reason didn’t meet expectations? I guess what would you say you guys didn’t get right, when you were hypothesizing which ones would do well?
I think there’s this dirty little secret in venture capital, which no investor is going to admit to, but I will maybe be amongst one of the first which is FOMO. Party rounds, let’s just you know, talk about the elephant in the room, I think it’s very easy to get persuaded by founders, strong founders who have the ability to rally a group of investors around them and create that sense of interest and urgency and generate this FOMO, we certainly did pop money into some of these companies. And granted, they were exceptionally strong founders. But I think, I think a lot of the learnings from that feed into the kind of investor that I am today, which is, you know, without building true intrinsic value in your company, that hype can’t sustain you for the long run. So a large part of how I think about investing now is coming at it from a more, you know, value based approach, which is that as long as we continue to generate value in this company, we remain ahead of the game. And we don’t have to be a slave to having to raise venture capital because we’re creating and building a real business.
I could go much deeper on that, but I’d like to stay on the topic of accelerators. Given your experience and the recent changes that we’ve seen YC make, I believe they’ve tripled in size from the cohorts of a few years ago. I’m curious from someone coming from 500, why do you think these cohorts have gotten so large at YC?
My guess is that they’re trying to index a much broader geography now. So they’ve pretty well dominated the US and Canadian markets. My guess is they’re trying to dominate other regions and index probably the entire globe. But I don’t have any internal insights that validates that.
Do you think we’re gonna see YC out-compete the other accelerators? Or, I mean, when we look at the track record of YC, I believe they’re at 60 unicorns or so and I don’t know the numbers from the others. But what do you see happening to the accelerator market? In general, do you feel that there will always be a few players that founders look to go through? Or do you think YC is ultimately going to win out and have a monopoly in this space?
I think there will always be a handful of players, I think YC has obviously dominated and remains the number one brand and with good reason, I think they’ve done an exceptional job. But I think there is always room for second and third players, and particularly when you look at a model like TechStars, which has industry focused accelerators, which may appeal more to a startup versus a generalist accelerator in the instance that they want very specific industry expertise or introductions. So I do think that there is room for a handful at play. And I think that YC has dominated for a while now. So I don’t see any indications that the other ones will fall away.
Would you say that 2048 has been affected at all by how large these cohorts have gotten?
No, it certainly is not something that keeps us up at night, nor do we think about it as being a threat. We certainly look to accelerators, in general, as a fantastic source of deal flow, we do tend to shy away a little bit from YC companies coming straight out of the program, based purely on where they’re at in their journeys, they tend to be a little bit later, or at least priced a little bit later. But if we get access to these companies going through YC, early enough or prior to them heading into the program, then it definitely feels like a win win. So So overall, no, we certainly don’t feel threatened by any means. And, you know, fundamentally, I’m a big believer of the accelerator model just in the sense that it, it’s a boot camp for founders, and it really condenses their learning period, what might take them 12 months to learn, they can do really fast in two to three and just come out and be able to hit the markets in terms of trying to raise capital or trying to make their first sale or try to think through pricing and do it a lot more eloquently, because they’ve had that intense coaching and mentorship and training. So I’m a huge proponent of it. I think as long as founders are open and willing to taking the dilution, I do think it adds and continues to add a tremendous amount of value.
So is there any founder that you think an accelerator is not a fit for? Or how would you advise me if I was a founder and deciding whether or not I should join an accelerator?
I mean, the most basic one is, have you founded a company before? Are you a seasoned operator? How far along are you in your career, a lot of these are factors that definitely feed into whether or not a founder feels like they’re fit for an accelerator, I think sometimes when it does tend to make a lot of sense is when a company is still in heavy experimentation mode, they haven’t quite nailed the product that they want to go after they’ve kind of identified the problem that they want to solve, but may not have the right elements of what that solution may lead to. I think that’s a really good time to consider an accelerator because it a buys you a little bit of time gets you a little bit of money and get to that intense mentorship to try out and experiment with a bunch of different models before coming out and landing on something. And then the dilution one again, that’s just really obviously, these are expensive programs. You know, there’s no two ways to slice and dice them. So really just comes down to a personal choice. Is the founder ready and prepared to give up that type of equity ownership? Or do they feel like they can get that value in some other form. And there’s many other forms, of course, to obtain the value that an accelerator provides.
Definitely. We’ve also seen other reputable firms like a16z with their startup program, which will invest a million dollars to help founders get off the ground. And Sequoia is doing something similar with a program that takes founders through an eight week intensive hands on experience and also invests million dollars. Why do you think these large firms are doing this? And do you think we’re going to see more of it?
Yeah, for sure. I mean, this is a strategy for them to have access to companies, so that being the off chance that these companies grow and thrive and excel, these funds have a first row seat, and possibly the first chance to pop in a bigger check. I think it’s a strategy which has been around for a while, a lot of times we see this through Scout programs that funds have been running where they’ll give individuals, you know, anywhere from half a million to a million dollars to pop into companies of their choice without really any oversight. And then, you know, help keep track of how those companies do in the off chance that they bubble up. So I think this is just a different format, where now the funds themselves are saying, they’ll be the decision makers of them and put a bit more structure around it. I haven’t personally bumped into any company yet that’s received this kind of capital, I suspect, we absolutely will obviously, it’s going to create a lot more quote unquote, competition in the early stage market. But I do wonder whether 2048 Ventures is possibly looking at industries where these firms may not be as focused, we tend to be a bit more deeper tech heavy bit more focused on companies solving challenging and hard problems in deeper tech verticals. So I’m not entirely sure why we haven’t seen them yet, or possibly these larger funds have slowed down the piece of writing these checks, just given what’s happened with the markets in the last several weeks.
Do you think other firms are going to follow suit, like the general catalysts of the world, the Index Ventures of the world, Excel? I mean, there are a number of other large funds with as much AUM, do you think that this is going to be the beginning of a common theme that we see across these multi stage funds?
I’m sure these other funds are keeping a close eye on this strategy to see if they should follow suit. I think there certainly is a bit of signaling risk at play here, which hasn’t been fully understood or seen through which is, you know, if a16z pops these million dollar checks into 50 companies, but only follows on into two of them, what happens to the other 48? And how does that impact their ability to continue to raise given a 16th had the insider look at these companies. So I mean, signaling risk has always been around. And I think the way some firms like YC, or other accelerators have handled it is to say we don’t do any follow on. And so you know, our sweet spot is to write these early stage checks. And that’s it. But when you start to do these opportunistic earlier bet, that’s when this can become troublesome. I think that’s why the Scout programs have traditionally done well, because it’s a layer removed. It’s a third party that’s sort of writing these checks on a fund’s behalf. And so the fund has a little bit more leeway to say, you know, this didn’t quite surface up to us, or there’s a lot of different ways they can play that. But with direct investments, I myself am really curious to see if and how that signaling becomes an issue. And I’m sure other firms are as well. And just managing the program of that size and caliber, right it, it’s certainly challenging, because early stage companies tend to be the ones that require the most amount of coaching and mentorship and see the greatest amount of input. So I’m not entirely sure if there’s structuring programs around that as well. But it certainly requires a great amount of operational sophistication to be able to not just write the checks, but then to manage the aftermath of it.
Definitely. So we spoke before the show, and you said that you’ve been spending a lot of time thinking about the intersection of technology and human psychology and how it’s both helping and hurting humankind. Can you elaborate on what you’ve been thinking about, specifically, and how this shapes your approach as an investor?
Yeah, 100%. I think that the thing about technology is that, and the thing that we forget to remind ourselves often enough, is that we as humans are not robots. And we’re complicated individuals with a lot of feelings and emotions. And technology can sometimes impact us in ways which can trigger emotional reactions or feelings, which are unhealthy. And I think the biggest example of this, in my mind is social media. I think social media, when it first started had a huge amount of benefit in terms of just making the world a much smaller place and connecting people at its core, but it’s evolved into something which is, you know, it’s become a form of entertainment and a form of entertainment, which I truly believe people in certain age groups aren’t ready to handle. And it’s affecting how they think about the world. It’s affect self esteem. There’s been so many studies done on this. And it’s affecting particularly young girls as they’re in their impressionable years and being a teenager and coming up in through elementary and high school. So I started to see a bit more being done on the regulatory landscape of cracking down on these companies in terms of making sure that they’re appealing to the right users and doing so in a way which is constructive, but I don’t think we’ve even scratched the surface of what we need to be doing. And, you know, I think we’re all To wake up one day and world is going to be vastly different where I personally don’t think social media will be as much a part of our lives in 20 years as it is today. But once we realize the mental health, detriments it’s having to both young people and old, you know, it’s truly a form of addiction at this point. So I have very strong views about it. I’m probably one of like, I don’t know, a handful investors. I mean, I’m in tech, and I’m an investor. And you won’t find me on social media because I have such strong negative reaction towards it. But you know, in my mind, this is the 2020 version of what smoking was in the 60s. You know, everyone loved it. And it was great. It was a form of entertainment, and everyone was on the bandwagon, not realizing the harm it was doing that was physical, this is mental. And so I think about this a lot when I meet new companies, and I think about you know, every every company that we’re meeting with is impacting human lives in a way, I think a lot about, is this being done in a way which is actually forwarding society, or is this kind of hinder society? You know, we talked about Metaverse a little bit, that’s another really great example. Is everybody going to be living in the metaverse in 20? years? No, absolutely not. Why? Because we’re humans. At the end of the day, we’re not robots, we have complex needs, we need human interaction, we need to feel grounded, we need to feel connected. And without that there’s going to be real, true detriments. So, again, I think there’s a lot of interesting new research being done in this space. And I know in the past, a lot of tech companies have hired psychologists for the opposite reason more around the reason of how do we get people addicted to tech, which is horrible, but it’s true. I think the opposite is going to start to happen where a lot of psychologists will be hired by tech companies to figure out how do we actually leave people with the right feeling? And not cause more detriment? Are more harm than good?
Is this present only in consumer in your mind? Or have you seen b2b technologies that are also hurting humankind? Maybe ad tech, but I’m curious as an investor, and you clearly have thought about this a lot, what on the b2b side is hurting humankind? If anything?
Yeah, it’s a really good question. I think the only example that comes to mind is just you know how the naive format that AI is still in. And there’s been a lot of use cases around bias creeping into AI. And you know, that piece of it hasn’t been quite figured out yet, in terms of how do we make sure we stay away from making the wrong decisions if we’re leveraging AI, but I can’t yeah, I think the difference between b2b and direct to consumer is that b2b is typically solving a very specific and real problem. And consumer tends to be in a format of a lot of entertainment. And it’s when you get into this category of entertainment, where you start to see a lot of this negative windfall that I’m talking about.
So is it fair to say that you’re actively avoiding those areas as an investor areas that you feel like, even if it’s a second, or a third order effect could negatively impact humankind?
I think we just as a firm don’t focus a lot on direct to consumer. So yes, to your point, certainly avoiding it just by way of the fact that we don’t typically go there is always something that is sort of sits with me under the surface. But I can’t say that I come across companies like this all day long. And so have to consciously think about this. I think this probably impacts me less as an investor and more as a citizen, as I think about what technologies do I want to adopt to my daily life?
In your opinion, have we reached a period of incrementalism in tech?
Yeah, I mean, it’s hard to say right? If you compare this to 10 years ago, hell yeah. But if you look out another 10 years, it’s like maybe no. I think you really have to go vertical by vertical, one vertical, where I am so passionate about but really think we’ve hit incrementaism is cybersecurity. You know, here’s a really great industry where everyone is truly up to solve one problem. And that one problem is keep the bad guys out. How do you do it? There’s a myriad of different ways a bajillion different technologies. Nobody really knows if anything’s if anyone’s really works until the bad guys get in. And so what is that next major wave in cyber, that’s really going to move the needle? I haven’t been able to figure that out. So that is one industry where I think we’ve certainly reached that point. And then I think there’s examples in many other industries. And then there’s new ones. I think, this is why web 3 has so much hype around it, because it’s way more nascent. And there’s a lot more room for radicalise new innovation in it, particularly if we talk about the merging of web two and web three together, but it’ll be interesting to see.
Are there areas in cyber that you’re paying close attention to or that you have identified opportunities around?
Certainly along the lines of just Long Tail, you know, you look at Think about the SME category and how everyone was forced to come online with COVID and cyber as an afterthought for truly all of these companies. And as these companies store more and more customer information, payment information and become more and more embedded in society, I mean, they become really great gateways for taking down not only the ability to steal a lot of information, but you know, taking down core functions. So that component, the longtail component of it, you know, when you think about the SMB category really is a form of consumer in a way. So I kind of get them realizing the importance of cyber, and how do you build a product for them, which is easy to use, and effective. And these are all really complicated things. I think with that specific thesis, there’s certainly a timing element at play, but definitely an area that I’m keeping a close eye on.
If we can feature anyone on the show, who should we interview? And what topic would you like to hear them speak about? Yeah,
I think I think it would be really interesting if you haven’t already done this, to interview a general partner or fund manager to talk through their experiences with raising their fund. Because I think that VCs are often A) misunderstood but B) over glamorized. And I think it’s important for founders to really understand A) what drives ROI to fund and what motivations do VCs have? And what struggles do they go through to raise their own capital? So I think driving a little bit more transparency in this market would be a really interesting segment. In terms of who I think there’s way too many brilliant individuals to list. In fact, I think your firm could do it.
It was definitely an arduous process for us, that’s for sure. What resources books, blogs, videos, articles, have you found particularly valuable and would recommend to listeners?
I have a new category or genre of books and I’m a bit obsessed with and it learning tied in with you know, a form of cheesy entertainment, and that is about startup failures. So WeWork story, the Theranos story. I recently read about the Sackler family and the OxyContin story. So I learned a ton about what goes right and what goes wrong along the way, the importance of ethics in building your business. So really fun category of books to read. But just generally speaking, I think there’s so much great content out there, it’s really hard to point to one thing, and I personally try to stay as diverse as possible when it comes to the information I ingest just so I can stay on top of a myriad of different trends and ideas and thoughts.
Do you have any tools or hacks that are a secret weapon?
Whoo, yes. So the intersection of Superhuman with Vimcal. Vimcal is a new calendaring app it is a thing of beauty. So highly, highly, highly recommend.
What do you know that you need to get better at?
I definitely am off the radar. I’m not on social media. I think having a megaphone of sorts to talk about my ideas a bit more and share thoughts is beneficial. And I love that I’m doing this podcast. I think I need to do more of it. So thank you, Nate, truly for having me on here.
Of course, we’re happy to have you. And what’s the best way for listeners to connect with you?
Find me online. LinkedIn is probably the only place I’m active or just send me an email. Neha @ 2048.VC.
You respond to cold emails?
I read every cold email.
Fair enough. All right. Well, they have thanks for joining us. Thank you for having me.

Transcribed by https://otter.ai