330. Building Unicorns from the Ground Up, Recruiting Founders from the C-Suite, and Driving Top 1% Returns with Concentration (Jed Cairo)

Jed Cairo on TFR

Jed Cairo of Juxtapose joins Nick to discuss Building Unicorns from the Ground Up, Recruiting Founders from the C-Suite, and Driving Top 1% Returns with Concentration. In this episode we cover:

  • How Private Equity influenced Juxtapose’s Model
  • Why Juxtapose isn’t your typical Venture Studio
  • Concentration in Venture Building
  • The Four Buckets of Investments
  • Why Other Venture Building Models May Fail

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Transcribed with AI:

Jed Cairo joins us today from New York. Jed is Co founder and Managing Partner at Juxtapose. a venture fund focused on delivering venture upside without venture risk. Juxtapose has built and funded companies including Care/Of, Orchard, Tend, Modern Age and DayForward. Jed, welcome to the show.

Thanks, Nick. Very, very grateful to be here.

Yeah, it’s a pleasure to have you tell us a bit about your background and your path to venture.

Sure. So I have a somewhat non traditional path to venture, I started my career as a private equity investor, came out of Wharton as an undergrad and got my MBA and then join KKR directly from school, had a chance to get my butt kicked for a couple of years, and decided to try and find more entrepreneurial seats for investing. I ended up joining a hedge fund called BeaconLight Capital, which was about a year old at the time, where we were doing private equity style investing in public markets. And around that same period of time, I started to make direct angel investments, and did that for a number of years. And it was partially scratching the entrepreneurial edge for me, but I wanted to take it a step further. And so I started to build companies, largely on nights and weekends, and came to fall in love with the process of going from exploration of the world to business thesis to helping bring a team together, bring capital together. And about eight or nine years ago, at this point, I made a decision to leave my partner at the hedge fund and try and create an institutional platform focused on serially building technology companies. So we are VCs in the sense that we focus on high growth technology businesses, we’re a VCs in the sense that we provide capital to those businesses risk capital. But in a lot of ways, our model looks pretty different because we focus almost exclusively on businesses that we help shepherd into the world, for lack of a better term.

Jed, is it fair to characterize Juxtapose as a venture studio?

It requires a nuanced answer. I think that the venture studio model has has lots of different flavors. And and as you know, there’s plenty of non-venture studio VC firms that have been really successful, and that the type of company building that we do. So I’d say yes and no, yes. In the sense that we focus on building new businesses. No, from the sense that the way that we go about doing that looks pretty different than most traditional venture studios, which I’m sure well, we’ll talk about as the conversation progresses.

Everything’s constantly evolving, right? The types of models and the nuances in those models that I think when we started the show, like eight years ago, they were called venture builder models, and then it was foundries and then four years ago, you know, studios and the permutations there in, you know, continued. But before we jump into that, Jed, you know, talk to me a bit about, maybe the elements from private equity in your hedge fund days, you know, KKR and BeaconLight, what strategic elements from that training do you employ as part of the strategy adjusted close?

I think we care a lot about underlying business fundamentals and industry fundamentals. And so we spend a lot of time thinking about incumbent market capitalization within an industry, which is a lot of technical jargon, but basically means, what does the world think X industry, life insurance industry is worth. And we tend to focus our efforts on industries that play a role in daily life for many are most Americans and have stable industry structures such that they earn healthy returns on capital and have stable profit pools, and therefore are very valuable. And part of it is upside oriented. Right? So if you want to build a $10 billion business, it’s much easier to do that if you’re disrupting 100 or $500 billion of market cap than if you’re disrupting $50 billion of market cap. But the same is true from from a risk perspective. And so we’ll pick a more modest type of goal if you’re trying to build a billion dollar business, it’s often much easier to do that. In an industry with $100 billion in market cap, then five or 10, we also care a lot about business model architecture. So there are some business models that the way that they consume capital, the way that revenue repeats, or doesn’t repeat, the way that they have permission or not permission to cross sell products and get incremental revenue looks different. And a lot of that type of thinking comes from, from training within private equity. On the hedge fund side, I think a lot of what makes what we try and do different than normal investing roles is there’s no company to go diligence. And so people don’t come to us with decks and with data rooms and with signs of traction and existing products. And so the research exercise is highly unstructured. And I think one thing that hedge funds, good hedge funds do really well is very creative research. So learning how to go talk to customers learning how to find secondary data signals that might point towards or away from an opportunity to learn learning how to do really good competitive analysis, and doing all that in an unstructured way. Because public markets and information flow is is highly restricted and highly regulated. There’s a lot of scrappy, entrepreneurial ways of gaining information that I think are important to be a good hedge fund investor, and are also important, at least in our model for how we like to build companies.

So you’ve kind of given us a bunch of hints on on how the model works here, Jed, and you and your partner, Patrick had been at it now for seven years across two funds, pretty short list of investments, but in Crunchbase, it appears that they’ve performed quite well. So can you give us more detail on the venture studio model how you’re different than that, and how you’ve survived and appears to be thriving, whereas the majority of these or similar models have failed.

Yeah, it’s flattering intro, I hope we can live up to the Crunchbase. That’s the primary difference from an output perspective relates to volume. And so the the reason I bristle a little bit at the term venture studio is I think a lot of venture studios come with a very venture, some mindset, which is not inherently good or bad. But it speaks to a way of thinking about risk and reward and process. And so we haven’t done very many companies, but the percentage of those companies that are on track to be successful, and the percentage of those companies that are on track to be very successful, so call them, you know, multibillion dollar outcomes is fairly unique. And our belief is that in really concentrating our efforts around a small number of things, and focusing on things that have a certain set of attributes, which we can talk about how we will be able to have a highly differentiated, both batting average in terms of success versus failure, but also slugging percentage. So what percentage of our businesses go on to be unicorns go on to be really impactful within the industries that they’re participating in. And everything kind of flows. From there, I’d say one of the things that would pop out for someone who looks at our website, and maybe looks at the website of a another very early stage investor or firm that focus on company balding is the profile of the CEOs that we partner with, and really at the center of our belief set, which is somewhat counterintuitive, because we’ll spend years literally years developing a thesis is that at the end of the day, the thesis is worth about five to 10% of the battle. And really the battle is won by the caliber of the team and the culture. And all of that starts with CEO. And so our CEOs are highly experienced highly successful entrepreneurs and executives who have already proven in other contexts that they can build companies that scale and to the hundreds of millions of revenue into the 1000s of employees. There are folks who have already returned hundreds of millions or billions of dollars to investors. And in a lot of ways, that’s really the key differentiator for us is the quality of those partners that We have. And the way that we earn the right to work with people of that caliber is by developing, really high conviction, well researched unique theses that cut through the noise for people who have all the opportunity costs in the world.

Jed was the amount of time between engaging with a prospective CEO and commencing them taking that leadership role at a startup that you guys are building.

It is highly variable. So if they’re on the beach, and they’ve been looking for a long time for this exact thing, and they find, and we have the right intermediary, setting the relationship up the right way, it could be relatively short, so call it a couple of months. There are other cases where we’ll get to know someone over the course of years, and maybe have a professional relationship where they serve as an advisor on a business or on the board of a business, and then transition to a CEO role on something else. Or they’re just friends in the ecosystem that we can get to know we can be helpful to them and their current role, they can be helpful to us. And we tend to take a very, very long term view about these relationships, in part because we do so a few things, that investing in for five years and developing a relationship with a really talented person, and then getting to work with them is totally worth it in a way where if we were our portfolio construction looked more like a traditional early stage venture firm where we’re making 2030 40, 50 investments in a fund, it would be very hard to justify that type of relationship investment for someone who may or may not play a role for one portfolio company out of a pool of hundreds over time.
How do you deal with the potential risk of leaders that maybe caught a wave had some success? Maybe they built in a different context, maybe they have expertise in a certain market, or I’m thinking I we had Dharma stacker on the program some time ago, and he talked about how there are CEOs with certain mindsets and different generations. Like when he started in VC a couple decades ago, the CEOs were all tech first and find the problems later. And that’s changed significantly, you know, that the mindset of the types of leaders, you know, how do you address that we’re making sure that the leaders that are taking, you know, these positions are flexible and can move with the times and can build billion dollar companies, regardless of specific context?

Yeah, it’s a great question. And I wouldn’t claim that we have solved that problem. And in some ways, I think it’s an unsolvable problem. And if you ask a really talented person who spends a lot of time recruiting, what their success rate is, if they tell you it’s 100%, then they’re probably either lying or lying to themselves. So I think you’ve identified a really important point, which is circumstances matter. And what enables someone to be successful is as important as whether or not they were successful. And frankly, sometimes having a meaningful failure in the middle of your career can be a really wonderful catalyst for someone’s subsequent success. We tend to take a fairly evidence based approach, and try and understand very deeply what someone’s mindset has been with regard to leadership, hiring business strategy over a long period of time, we try and get to know people in the context of their pre professional selves, understanding what their childhoods were, like, what their families are, like, why they got into business in the first place, and then spend a lot of time understanding track record, we tend to gravitate towards leaders who have relatively long stints in jobs so that you can separate out signal from noise and tend to focus on leaders who, within those prior positions were in very senior roles where attribution is easier to suss out than if they were part of a larger team, trying to accomplish something and the thing we have going for us is the ability to be extraordinarily thorough, and so we never rush. We take our time getting to know people, we spend a lot of time with them. Both in the context of getting to know them socially, having them get to know us socially, having them spending time with people in our ecosystem, and doing very deep and very systematic references. But again, because we’re doing so few things, we can invest five to 10x the hours in a search like this, than many folks could justify. And the hope is that coming out of that, we’ve built a high trust relationship, we have effectively communicated, what the work to be done is such that someone knows what they’re signing up for, we’ve given a good opportunity to understand what it’s like to work with us as partners, both through direct interaction and interaction with folks who have had the chance or that burden, I suppose I’m working with us for for multiple years. And out of that third, as we would hope that that matching process, that partnership process, stands a greater chance of success than if we were less thorough. And, you know, we’re, we’re pretty fortunate in the sense that we start by fishing in pretty elite circles. So these are people who are successful serial entrepreneurs, they’re public company CEOs, they’re people who have run, you know, multibillion dollar business units for some of the most successful companies in the world. These are people really at the top of their game. And that creates a huge responsibility for us to live up to the expectations of these partners, and to be as good of partners to them as they are to us.

You know, I want to continue this line of thought, but just step back and set the frame a little bit here, can you give us broad strokes on, you know, size of fund portfolio construction, how you deploy dollars into these opportunities over time, stage capital?

Sure. So at a high level, we currently manage and fund capital about half a billion dollars. And that’ll be deployed and to call it 15. Companies, we are very much early stage biased. So the majority of the capital goes into call it seed and a, but what is a little bit misleading about that statistic, is we have an expectation from a an ongoing engagement level perspective and capital based perspective to be fairly flexible. And so in the coming months, you’ll hear about some new and interesting ways that we’re building companies with new and interesting partners, which fall outside of the normal construct of seed A, B, C, in a lot of ways we think about our core work to be done is helping to bring amazing companies into the world and bringing people around the table to to help make that happen. And fun structure and round names and partner set is all construct. But we think that our activity set in a lot of ways is timeless. It’s the the atomic building blocks of entrepreneurship, its ideas, people capital, action. And for the last seven or eight years, we happen to have been doing that in a in a venture capital context. But we think that there’s no being overly focused on what the round is called, would be a little bit of tail wagging the dog and our perspective.

Savvy podcast interview move there, Jed dropped some teasers, and then we got to get you back on a few months.

I hope you’ll have me back.

So, you know, I can’t help but observe that a big part of your model is patience, that you’ve got to find the right talent, it’s got to be the right opportunity, you do a bunch of work to validate the thesis, which I’d like to get into shortly here. But is there any concern or risk that a startup or a new entrants will exploit you know, some of these big opportunities and, and move fast and build the opportunity that you had up on the whiteboard on the market map and just hadn’t, you know, assembled sort of the right team and, and taken a stab at?

Totally. I think that it’s something that we wrestle with constantly. I think that there’s a truism, and I’m sure, in your fun business, you experienced this as well, but you can’t authentically be something you’re not. And we are people who like to understand things deeply. We like to understand our partners and our partnerships deeply. We like to focus our efforts on things that we think have very high probability of success and impact. And there’s a cost to that. And the cost is, relative to some other firms, we are more risk averse, and we are slower moving. And it’s a trade that we and our limited partners are happy to have made. I think that the business risk is less that we get, quote, unquote, scooped on a thesis. And I’ll come back to that in a second. I think it’s more that there are certain ecosystems where we’re unlikely to be a competitive player, because they’re so new and fast moving and quickly evolving, that we like to understand an industry history going back 30, 40 years and understand what the milestones were that shaped industry structure. And there’s a lot of really exciting places to play and in venture land, that didn’t exist 30 years ago, and didn’t exist 10 years ago. And people will build incredible generational companies in those industries. But it’s unlikely to be us, because we like to understand where the puck is going with a lot of conviction. And there are some spaces where things are just changing too quickly. Not necessarily to have a bet but to have a really high conviction bet.

Get you know, as mentioned in the intro, here, your model is described as delivering venture upside without venture risk. Recently, Cambridge Associates released a report that published that traditional venture capitals, historical loss ratios of greater than 50%, five zero, have dropped now to 20%. You know, with this lower failure rate in traditional venture, does that change the risk profile? Or does it change, you know, the alpha that you can produce when compared to what was previously seen as a very high loss ratio asset class?

That’s a great question. One of our internal operating principles is this idea of touching bottom, which is Juxtapose speak for continuing to understand a fact or an observation at a deeper and deeper level. So at the risk of sounding like I’m avoiding your question, I’d probably start with trying to better understand the CA statistic. We’ve been in an incredible capital market environment for early stage businesses, given the number of new participants and the amount of capital and what until recently was a very supportive public market from a valuation perspective. And so I think the capital loss ratios and probability of failure ratios are probably 2021. We’re at an all time best I have to imagine for early stage venture businesses, and we’re believers at least that there will be some mean reversion. And, you know, we’ll see what the markets look like in 2022, and 2023. And firms that had good fun one that don’t raise a fund to or had a good fund one and a bad fund too, and don’t raise a fund three. So in the context of early stage venture, you don’t really know the score for quite some time. And it would be hard to say that there’s going forward 80% of venture backed businesses are going to be successful. I think the other thing that if we were trying to touch bottom, we would want to understand, in addition to the time horizon around that statistic, is really understanding what success or failure means. And so in a context of a venture portfolio, if you want it to be really simple minded, you could divide your portfolio up into things that blend down your fun, multiple or blended up. And one of the things that might make that statistic a little bit challenging to really base a business model off of is how they would think about a business that returns capital, or returns two times capital or even three times capital, where if you are a top decile venture fund, a 3x blends down your return. Yep. Right. And if you’re a top 1% Venture Fund, an 8x plans down your return. And so you could say things that are eight axes are in a sense failures because I’ve given up opportunity costs to things I could have invested in and invested my time in that would been my multiples up I think in our context, we would probably divide success and failure into maybe four buckets, I think that there’s true capital impairment. And in our model, we should have significantly less capital impairment than in normal venture. When we were starting the firm, we talked a lot about the loss ratios of the world class, multi decade growth equity firms, so think you’re a TCP in general Atlantic’s, et cetera. And what those businesses have been really good at is identifying companies that have strong fundamentals that have momentum behind them with good leadership teams, in industries that have a fair amount of stability. And they also have the benefit of the way that their securities are structured that helped them but they don’t lose money very often. And so in that first bucket, true capital impairment, we would like to have a much better batting average than then the industry at large, we’d probably have a second bucket, which are things that do better than returning capital. But when dawn returns, and inevitably, those things will happen, I mean, mathematically, they’ll happen. The third bucket would be things that blend up your returns and are very solid. And then the fourth bucket is your role beaters. So things that are 20 baggers, and better that add in the context of of our model, where we only have call it you know, eight companies in a portfolio, a 20x, on an eighth of your capital, does really good things really quickly, to your overall multiple. So we do talk about risk and reward in the language that you referred to. But the real question for what drives returns is, if you don’t have that many things in bucket one, so called capital impairment, the real question is, how much are your portfolio is in bucket three, and bucket four? And the real difference maker is, do you have things that enter bucket four. And if you have things in bucket four, then just mathematically, the bucket one bucket two stuff is less important. I think what is different about our model is, we can be a top 1% fund without anything in bucket four. Because we’re concentrated, we have very low cost basis. And we have very few things that fail. And I’d say the private equity downside really speaks more to that than anything else.

You think that your model specifically is one that will become copied, and will become a larger portion of, you know, the future of venture building? Yes. Always looking over the shoulder a little bit.

That’s wonderful, right like that moves the world forward. You know, when I was in the hedge fund business, our fund kept growing and our investable, universe shrunk. And we got to a point where there are probably 2000 stocks in the world that we could invest in, which sounds like a lot. But if you have a team, and you’re looking at 20 things a year, you go through that investable universe pretty quickly, in the context of building companies, the world is your oyster. And so we’re not the only people who build companies in this way. And there are other firms that we admire, and and have built some amazing businesses, we don’t really run into each other because the world is so large, and we’re all pursuing things in slightly different ways. This maybe gets back a little bit to the point that I made about authenticity. We are who we are, and other firms that even if they were intending on replicating our model, I think the people inside that firm would be bringing their own personalities, their own biases, their own experiences to the process and culture that they make. And it would end up looking pretty different.

You mentioned in the hedge fund days the investable universe for you as 2000 different equities. You’ve also said with Juxtapose that you filter out 90% of opportunities before even looking at them. And what are some of the factors or characteristics of the 10% that you are engaging with or building a thesis around?

Yeah, so we’re generally looking for opportunities where we can take a meaningful bite out of market risk and product risk or putting it in a positive sense things where we feel like we are having positive selection on market and on product. So for the type of screening that you’re describing, that’s much easier to do on the market side than the product side. And so we’re generally looking for industries that first of all we can understand and so there’s a level of scale and duration that We think allows us to develop some degree of expertise. A lot of this is no dust stuff. But you’d be surprised by how many people don’t follow these practices. We like bigger markets more than smaller markets. We like more profitable markets more than less profitable markets. We like markets that have structural indications of low competitiveness. So what would an example of that be fragmentation, high fragmentation, high variability and profitability levels, I’d say the biggest one that we look for is customer satisfaction, how happy our end users with incumbents, and nirvana for us is an industry where customers are going to the industry in large numbers, because they have to, because that’s some in COVID time, there was a lot of talk about essential industries. So there’s something essential about the behavior within an industry, but you have really terrible net promoter scores. And the reasons why that’s the case comes down to things that we feel like we’re very good at. So how well is technology being deployed? How well is digital and non digital service design and experience design? Are the people running the businesses at the top of the food chain, people we’d be excited to compete against, or people we’d be afraid to compete against? Are the companies at the top of the food chain structured in such a way that they’ll be highly competitive or not highly competitive? So we tend to take a on the one hand and analytical approach, and on the other hand, very human approach. So do we feel like there’s an opportunity to do good in a category? Do we feel like the fundamental nature of our innovation would be good for the ecosystem? Or not good for the ecosystem? We’ve got a, you know, a 20 person team? Are people passionate about it? Like does someone want to spend the next 10 years living and breathing in this category. And it’s the combination of those things that filter out a lot of a lot of what we look at.

In a previous career, I did M&A for a conglomerate called Danaher, and this is all feeling very reminiscent of that exercise. To some degree. It’s basics, but it’s how well you do it. Right. Yeah. Jen, can you talk more about this research process? The expectation is, in many of these cases, you guys are going to spend 10 years in this industry. But if you rewind back to the development process, and that the team undertakes, can you walk us through a bit of that?

Sure, without enabling future competitors. Our research process is a very in depth version of research processes you’d find at other venture funds, hedge funds, and private equity funds. So we do significant commercial diligence, where we really try and develop expertise. From a top down perspective on a category, we have a team of experienced designers, user researchers, ethnographic researchers, that try and understand behaviors that are existing in a category, and how certain types of innovations might appeal to different segments, how they might impact different participants in the ecosystem. And then, in a very private equity like way, we try and be really thoughtful about validating those assumptions, both by bringing people into our, into our tent, who know where all the proverbial bodies are buried in industry, and where you might get tripped up going from a presentation or a memo into reality. And also validating or thinking deeply with users over time through qualitative and quantitative methods. So that end to end process is probably on average five to 10 person years of time. And so coming out of that will have a level of depth that we think is appropriate. So we tend to want to find opportunities where someone who’s been on the inside of an industry for 30 years, won’t necessarily see it. But also, the solopreneur, who spent three months or six months on something isn’t going to see it either. We believe there’s a little bit of a sweet spot between insider and outsider that we shoot for.

I recall coming across material some time ago, probably a year and a half ago from Sam Altman. And I’m paraphrasing here but he said that in a previous generation of YC, they would take some of their most talented talent. So founders coming through the pipe that didn’t have an idea. And they also curated some of their best ideas and you know, biggest market opportunities, and they would pair them up, and they put them through YC and fund them cetera. And when he looked back at that exercise, he found that none of them were successful. You know, what do you think? I know, you can’t speak for YC or Sam. But you know, what do you think is the biggest difference in the model you’re employing versus, you know, that one and, and why yours has seen some early successes where in YC’s case, it didn’t seem to work out.

So I don’t know enough about the YC model to comment directly on on Sam’s comment with any level of confidence. So if Sam listens to this, take it with a grain of salt, I would imagine that the nature of the founder and our context and the YC context is very different. And so my understanding of YC founders are generally earlier in career, high potential high passion. First time CEOs. And our partners are on the other end of the spectrum, there are people who have done zero or small scale to massive scale multiple times before and have lived through the experience, good, bad and ugly, of bringing products to market, finding ways to sell those products, building leadership teams, building cultures, building organizations, and their people that I’m guessing if Sam met them, in many contexts, he’d write them a check, without knowing what the idea is. And I’m being a little bit flip. But I do think that there’s, there’s a tremendous amount of value that comes from having the right person pursuing the right space with the right architecture of a business. And in our context, that is a painstaking process, where we’ll often be spending time with a very talented person with a great track record, and will mutually come to the decision that as talented as they are, they’re not the right person for this concept, or that concept. And similarly, I don’t know exactly how YC source deals, but I’m guessing that they weren’t spending five to 10 person years developing them. And so the way that we think about risk factors, there’s product risk, there’s market risk, there’s execution risk, and any one of those things is a landmine that could lead to failure of a business. And it’s not surprising to me that if you were to, you know, take a quick pass, at any one of those three, you’re still gonna have a lot of fail points. And maybe the last piece of conjecture I’d have is the YC type of entrepreneur is maybe more personal insight, personal, passionate, oriented, where they want to spend time on the thing that feels like fully their baby in an industry that they love. And they’re evangelists and everything else, and maybe a little bit less oriented on the passion for building and bringing something to scale and bringing people together and leadership, which are maybe experiences that those folks haven’t had a chance to, to have at that point in their careers.

Jed, what role does mission and purpose play in the context of the work that you do?

It’s a great question. I think that it plays multiple purposes. I think the first purpose is, we care deeply about doing good as a firm. If for no other reason, then we have an infinite investable universe. And all else equal, we would rather do things that we can be proud of, and we feel like make the world better than not. And again, because the work that we do is so labor intensive. Someone has to keep spending time on it. And at the end of the day, Money comes and goes, individual relationships come and goes but values, reputation are things that are long standing. The second is, I think, in the world that we live in, the most talented people want to work on things that move the needle for society, and as I’ve said a couple times now, central to our success as a firm is partnering with the most talented people in the world, and enabling their ability to build the world’s most talent dense companies. And it’s very challenging to do that. In this day and age, if the thing that your company is trying to help her solve is not something that resonates from a heart perspective, consumers are savvy er than ever, people are savvy er than ever as they think about their jobs. And so there has to be real authenticity behind that. And it’s something that limits the pool of what we do and don’t do, but we’re very comfortable with that. And it frankly, it makes the work much more fun.

Yeah, if we could feature anyone here on the show, who do you think we should interview? And what topic would you like to hear them speak about?

One of our professional heroes or groups of professional heroes are the folks at Sutter Hill Ventures. They’ve very quietly, very successfully built companies for decades. And their approach is very different than ours, from what we understand, but I think would be informative as a point of contrast.

And finally here, Jed, what’s the best way for listeners to connect with you and follow along with Juxtapose?

We have a website, Juxtapose.com, an active Medium account and a growing LinkedIn presence. So I would love to hear from anyone whose curiosity has been piqued by this podcast.
Well a very enlightening session for me. I really enjoyed it, Jed, appreciate all the insights in the comments. And I look forward to doing this again, you know, in the future and to hear about some of these these things that are coming up for Juxtapose.

Likewise, Nick, I really appreciate the time.

Thank you, Jed.

Transcribed by https://otter.ai