342. Investing in $B+ Marketplaces, Beating the Cold Start Problem, Warby Parker's Key to Scaling, and the Backstory Behind Redpoint's Social Media Surge (Annie Kadavy)

Annie Kadavy of Redpoint Ventures joins Nick to discuss Investing in $B+ Marketplaces, Beating the Cold Start Problem, Warby Parker’s Key to Scaling, and the Backstory Behind Redpoint’s Social Media Surge. In this episode we cover:

Musings on New Marketplace Models
Increasing Diversity in Venture
The Importance of Building a Brand
Rethinking Success

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Transcribed with AI:

0:03
Annie Kadavy joins us today from San Francisco. She is Managing Director at Redpoint Ventures with investments in Tend Dental, Guild Education, and LogixBoard to name a few. Prior to Redpoint, she was the Head of Strategic Operations at Uber, growing the Uber Freight division from pre product and pre revenue to over 450 people. And before that she was a GP at CRV. Annie, welcome to the show.
0:28
Thanks so much for having me.
0:30
Yeah, so talk us through your background and your path to venture.
0:33
Oh, my path to venture was not particularly planned, I would say I didn’t grow up knowing what venture capital was, or really much about what technology was, if I’m honest. I grew up in the Seattle area and moved to California to the Bay Area to go to college at Stanford. And that was, I guess, the first place I couldn’t help but be inundated by all of it. So I had always had the North star of wanting to be an entrepreneur and a founder, actually, and that’s what guided me to make a lot of the career decisions and education decisions that I did early on. And at one point, you know, fast forward to 2011, I had been working on my own company for a while and was also finishing up business school and had learned enough that I wasn’t going to continue working on the project that I was working on. At the time, we had a small group of people that had been building the product and a friend and mentor of mine, I had a great conversation with him and said, Hey, I’m thinking about joining a company. You know, here’s a few ideas of companies that I think are interesting in early stage. And I’m really compelled by their visions and how big they could be. And he asked me a question, which was, well, what do you think you might want to do there? And I didn’t actually have a great answer. I was more like, oh, well, I think they could plug me in to do a whole bunch of different things. But mostly, I’m just inspired by the people who I know there and the things that they are building, and here are all the ways that I think it could be a really big business. And he laughed and said, Well, have you ever thought about being an investor? And I said, No, I had literally never thought about it before. And at the time, you know, there was all this Ellen Pao stuff going on in the media, it was like on the front page of every outlet. And I was a young woman, I’d like to believe I’m still a young woman, but at that time was even younger than I might appear to be today. And it just didn’t seem like a place that was for me. But for a lot of reasons based on on background or what I perceived people to have, quote unquote, done before they got into venture. Long story short, that was 10 years ago, I ended up working through my own imposter syndrome, got the opportunity to invest in some really great companies learned a lot and most importantly, learned that I really liked the job. And so I have took a break, went to Uber and then came back to venture at Redpoint, about four and a half years ago.
2:33
Amazing. You said you always want to be an entrepreneur, I feel like it’s always been in my blood as well, I just always kind of felt that. Do you remember when it first struck you like when you had your first moment that you wanted to build and create businesses?
2:47
You know, I think it actually came out of a place of, of almost childhood admiration. I’m the oldest of four kids and my dad was kind of, he’s a very creative person who was always starting ideas and companies and building, you know, little products in our garage. And I think I always kept on a high pedestal, the idea of creating something new, or the idea of inventing something from nothing, or improving on a solution for a problem that you saw and existed. So I, you know, built some small businesses that you know, relative to the companies, I now get to, you know, front row seat to see and built all the time or nothing. And they were more like, you know, small projects, but they had the, you know, entrepreneurial spirit, if you will behind them. I filed my first patent in high school for a project that I had been building and wow, right. Yeah. So that might be a point of time, as I reflect back to say, Oh, wow, you know, here’s that how I understand the the process of actually starting to go do this thing with the view of, you know, solving a big problem for large group of people or customers or define that as well.
3:51
Awesome. Well, I want to hear more about your background. Before we do that, can you tell us the thesis at Redpoint?
3:57
The thesis at Redpoint is a great question. We’ve got two funds here, which is relevant. We’ve got an early stage fund – current fund that we’re just finishing up is a $500 million fund. It’s our eighth fund, we invest across enterprise and consumer companies, mostly at the series A, some seed and some series B. We also have an early growth fund that invests in you know, the next next stage, so Series B, Series C, they also invest across many sectors, mostly enterprise and infrastructure focused. Thinking through the lens of I spend almost all of my time on the early stage side, we do have two different teams because we believe that the stages are different. And the things that give you energy often can be quite different depending on if you are, you know, seed investor, a Series A, Series B investor or you know, later stage growth investor. So we’ve got a bunch of theses and we look at them across different industries, mostly tied to teams and markets that can be, we think, world changing.
4:50
Awesome, and is there a stage or an area that you spend most of your time?
4:54
Yeah, so our early stage team collectively, we spend the vast majority of our time at what I historically would have called the Series A, we’ll call it the somewhere between their first and second usually round of institutional capital.
5:07
Got it. Perfect. Annie, I know you were one of the original team members at Warby Parker, did you have any key learnings from the early days there that helps inform how to successfully scale a consumer brand?
5:19
Oh, my gosh, that’s a great question. I had an opportunity to plop in and spend a bit of time with Dave and Neil and the early team, it was about 25 people at Warby Parker for a while, it was one of the best experiences I’ve ever gotten to have and count some of those people to be still really good friends. Some learnings – I think, deciding what are your non negotiables. You know, for them it was brand was a big part of it. And then being open and willing and even excited to do things that are not scalable early on, I think it would be two learnings. The third would be stay as close to your customer as possible. The early Warby Parker office that I was in was right off of Union Square in New York City, and you took, you know, a three person elevator up to the I think it was on the fourth floor of this building. And the front half of that office was the showroom for Warby Parker, and the back half was the office where the entire company, which was 25 people were sitting in working all day, every day. And so literally, as you were working on whatever project it was, you were watching, all day long, people come in to try on their glasses, and you were listening to the questions that they had. And you’re watching the process of getting their eyes measured, and of them trying on frames and how they came together, or how they brought their mom or how they brought their best friend. And it was really like a social experiment. And I think that, you know, for business like that building for consumers to be able to bring your team that’s working on kind of from HQ, and had them literally in the same room with your customers on a daily basis is is a really amazing thing to do.
6:48
Yeah, I remember, you know, building products myself, I was in an enterprise environment. But one of the biggest challenges I had, when defining requirements was translating customer feedback, customer discovery to the engineers and the chemists I worked with, like, they always wanted to know what the customers were thinking. And there’s an advantage to that you can be the filter, you know, and you can communicate on the things that you think are most relevant. But the disadvantage is like you’re this communication conduit, I can only imagine what it would be like to have all the developers and engineers get to see the customers in real time on a daily basis.
7:22
Yeah, totally. I remember, you know, specific anecdote, I was running an analysis on, you know, early on early days Warby Parker, right would send you your at home try on, and it was a box of five frames, and there was a question of, do we let people pick all five frames? Do we let them pick four or three or two? And then what other ones do we think are going to have the highest likelihood of being a match to them based on the ones that they picked? Right? And so there was a statistical analysis that I was doing. But in reality, I remember sitting there for a couple of hours just watching people try them on and seeing Oh, okay, like, these people are actually picking based on color, these people are actually picking based on size, these people are actually picking, you know, based on like the brow frame, right. Is that straight across versus is it curved or arched? Right. Wow. And so those things, it’s hard to, it’s hard to know, right? But you could add those into your question list as you’re onboarding people. And then you could also see in the data, right, okay, these people have picked three black frames, I’m going to show them two more black frames that maybe are going to look different, versus they put three small frames, I’m going to show them two other frames, maybe the same frame in two different colors. So things like that, that were kind of fun to be able to blend, you know, the data or screen work that you were doing with the actual you know, observing and interacting with customers in real time.
8:37
It’s so subtle, but it’s a brilliant insight. I remember walking into Warby the first time, and the frames were organized by narrow, wide, extra wide, something like that, or medium. And once I figured out, you know, I have a wide face, I only looked at those frames. And you know, that’s taxonomy and filtering, but consumers probably wouldn’t think of it. But if you’re observing and doing your job as a product person you can get there. Annie, I know you’ve invested in a number of unicorn marketplaces from DoorDash to ClassPass to Patreon, how do you think marketplaces now and in the future differ from those of the past?
9:14
Oh, man, that’s a really great question. In many ways, I don’t think that the metrics that guide their success have changed, right? The brilliance of a marketplace is that it democratizes access for both sides. And maybe both maybe three, or some marketplaces have multiple, you know, different users or different groups that you might call supply or demand. And so you know, the questions are always the same, right? What value are you driving to them? Why are they going to stay on the platform and what metrics are proving that this is a real fit for them that a marketplace is going to solve the problem? Some of those are related to the market, right? How fragmented is the market on both sides? How important is it once you’ve made a match with one person or one customer that it’s the same match the next time or third time or fourth time or is it actually makes no difference? Or there’s even benefit to having different matches. If you think about Uber or Lyft, right, the driver has effectively become commoditized. For get me from point A to point B, it makes no difference, right? There’s pros and cons to that I think about building the marketplace and also making matches versus an Airbnb. I don’t know, I’ve never seen the data inside of that company recently. But presumably, there’s actually benefit to each match being different people want to go to a different place want to go to a different experience. Those are good use cases for marketplaces versus ones where once I make a match, I want to continue to work with that person or that company, those are more likely to churn off of a platform. So I think, you know, what’s different about the next generation of marketplaces versus the ones we’ve seen? I think we’ve seen iterations on a lot of the same things. I we’ve certainly seen a lot more b2b marketplaces than have ever existed before. So that’s maybe an obvious answer, or at least feels obvious to me of something that is changing in the next generation. But as far as it relates to consumer marketplaces, you know, if anything, I think that we should see more big companies built in that space, the model is wildly successful, it’s very, very defensible. And for markets where you have high fragmentation and varying consumer interests or recurring needs, the marketplace models are really good one to choose.
11:15
Do you think we’ll see more decentralized approaches going forward?
11:19
What do you mean by decen-?
11:20
Well, I don’t know web three based marketplaces, you know, more of that more variable economic structures and incentive structures?
11:30
You know, yes, I think one of my favorite parts about this job is that you can never get good at it, because it always is something new, right? Like this, the question you just asked if you’d asked me that question five years ago, or seven years ago, I would have been like, I don’t even understand what you’re talking about. I don’t even have a frame of reference to think about what that would mean. And now I’m like, Oh, okay. I’ve got maybe 10 or 15%, of a frame of reference. And then I’m just left to my own kind of creative, my thoughts, right of like, what are the use cases for this and what they could look like? And so yeah, for sure. You know, I think that marketplaces, like any other technology, that’s consumer facing are reflective of the generations of people that start them and use them, you know, that generations of people now are understanding how to work with a blockchain, for example, and the values of that. And so, you know, I don’t think that we’re mostly going to get it right the first time around, but in 10 years from now, for sure, I think that there’ll be, you know, marketplaces that have different economic models, as you said, which I think is a good term to describe it.
12:28
So the last three marketplace pitches that I’ve received, the founders all mentioned the same phrase, the cold start problem, you know, and navigating that. Do you have any advice for founders starting a marketplace and beating the cold start problem, so to speak?
12:44
It’s just about defining your constraints. If it’s a marketplace that has a physical component to it, so an Uber or DoorDash, or ClassPass, you need to have a geographic constraint, obviously. And then you want to see if you can build some level of density. The word density means different things, depending on your business, right? If you’re DoorDash, you want, can you get to X percent of the restaurants on University Avenue in Palo Alto, if you are Uber, can you get to, you know, Y number of black car drivers in the marina in San Francisco? If you are ClassPass, can you get X number of yoga studios in Union Square in New York City kind of thing, right? So I think that that’s the first one to do. And then see if you can make your work on a really small scale, and see how people want to use it. Do they want to keep ordering and ordering and ordering? Do they want to keep writing and writing and writing? Do they want to keep going to multiple classes or classes at a single studio, right? And if you can see that it works in one very small geographic container, and defined as you will take your time to figure that out, you know, all of those companies that I’m talking about went through many iterations early on of it. And then once it’s working, you will know and then you go, you know, then you can grow your different geographies. I think for a digital marketplace, it’s a little different, right? You know, with Patreon, for example, I remember at the series seed that we invested in almost 10 years ago, Jack and Sam, the co founders there, had put up a really simple website, actually. And what was so interesting about it was that the number of use cases was really broad. From the beginning. So it was almost the opposite of what I was just talking about, with a, you know, geographically constrained kind of IRL marketplace. In this case, it was oh, look at this platform and how it’s working for a bunch of different types of creators and a bunch of different types of patrons that want to view their subscription based backers. Oh, wow, that could mean that this could be a platform, right? That it works for a whole bunch of different use cases, as opposed to just one meaning that it might be too small.
14:41
Did they maintain the set of use cases as they grew? Or did they kind of choose one and then re-expand later?
14:48
To my knowledge, I mean, we’d have to ask them how it’s evolved more intimately over time. I’m not on the board, and I’m not privy to any of their exact private user information anymore. But you know, I think digital marketplaces are meant to be a platform. And so the broader it can be, you know, you think about like YouTube is kind of an example. I’m not sure that we’d call YouTube necessarily a marketplace, but it is an aggregator, which is a derivative, you keep it as broad as possible. And you know, how could anyone know that like unboxing videos and ASMR, were going to be the bee’s knees. When you started out, it was, you know, people talking about totally different stuff, or gaming, right, for example, wasn’t even there at the very beginning. And so I think, to build a digital first or digital only marketplace, you want to actually make it as open as possible.
15:35
Marketplaces are kind of funny, because it feels like the critical mass required, especially in these in real life geocentric models, the critical mass required, and marketplace liquidity just has a different formula and a different definition. For every startup, I’ve yet to see one that’s even close to the same. I recently interviewed co founder of Grubhub, who now runs a business called Fixer, Mike Evans. And he said in the early days of Grubhub, I think it was getting to like 30 or 40%, of restaurants that delivered in a certain geographic range, that and then in that geo, you had it once you got that supply, the demand was just there. But you know, it takes a while to kind of figure that out. What winning looks like in a market isn’t necessarily obvious.
16:22
Totally, and how you think about putting the on the supply side, right? Like if we talked about restaurants for a company like Grubhub, or a different set of restaurants for DoorDash, right, you know, those that hadn’t already had a delivery person available to them? You know, how do you think about each of the margin on those relationships? How do you think about which ones are going to be your loss leaders because you need them? Which ones are you going to maybe charge more for upfront. ClassPass, I think is one of the most interesting examples I’ve ever seen of it, right? If you think about boutique fitness, broadly speaking, right, there’s quite a range in terms of the cost of them, the brand of them, you know, you have a SoulCycle, or a Barry’s boot camp, things like this, that are in multiple cities, and it’s a brand that holds some weight with consumers. And then you have, you know, hidden in the rough Annie’s yoga studio or something like that. Sure, that might be really great or might not be, but it was interesting to see how, you know, looking just at the supply side of those marketplaces, how they’re looking at each other for signals for do I want to come on to this marketplace? Is this something that my peers and or the brands or competitors that I maybe look up to or want to be associated with are also joining the platform is a I think, another really good early indicator of success.
17:29
Are there a few metrics at series A that you will look at, and you’re looking for certain benchmarks when a marketplace comes? I mean, we know they’re all different, we kind of established that. But whether it’s revenue or margins, or GMV, and take rates in this case, are there certain things that on the back of the napkin you’re looking for in a marketplace startup?
17:48
Yeah, it’s not GMV, which is almost always the first metric that I’m sent in an email or first slide on a pitch deck GMV should be a lagging indicator of success. So it’s great, you want to see what it is and see that it’s going up, right. But if we looked at 10 marketplaces, and they all had $10 million in GMV, those are gonna be really different 10 businesses underneath. So for me, it is repeat rate retention cohorts. So you know, for the month of January, the number of people or businesses or whatever onboard into your marketplace, what percentage of them are still transacting are getting value from the marketplace, one or two or six or 12 months later? And then related to that it’s not just the percent that are but the net revenue retention of that group. So are they spending more overtime? Are they spending less? If so, how much less? Why those are the metrics that matter most to me.
18:36
Is there a take rate that would be too low for consideration?
18:39
That’s a great question. You know, I’ve seen a few actually b2b marketplaces, right, where the average transaction is so high, like it’s right, six digits, right? If you’re transacting $100,000, and taking 2% of that’s not so bad, right? So I think it really depends on you have to look at kind of your average transaction size, but I couldn’t make a blanket statement of this percentage is just too low.
19:04
So Annie, you were Redpoint’s first female partner – a notable moment for the firm. What’s your approach to hiring diverse talent and supporting other women in the venture space?
19:15
Oh, I appreciate the question. Yeah, I am, I’m very proud to say that our early stage team is now 50-50 at every level, based on gender, which is, I think, an important but certainly not the only form of diversity that matters, obviously. You know, when I first started in venture, which wasn’t even that long ago, 10 years ago, there was maybe one, I don’t even know how to say it appropriately. But there was like maybe one other, usually that was one female inside of most venture firms, and now most of them have made a lot of progress. And I actually give you know, Aileen Lee and the All Raise team of which I get to be part a lot of credit to them, because they put some external pressure on some groups of people that were in control of making those decisions. And I think that that really did help push the market forward in a lot of ways that I’ve certainly seen around me. So how do I think about it, I’ll tell you having been the only in many cases, you never want to be offered a job, because you are the only. I used to say like, don’t give me a job because I’m short and have brown eyes, like, give me a job because you think I can do it, or you think that I’m going to be the best person for the seat. And that should be a function of talking with me on my background of my experience and my perspective on how to do the job going forward. It shouldn’t be something that I was born with or without. And so you know, I look at the team that we have that I am super proud of. And I really care deeply about everyone we work with, and 50% women, and again, at every level of seniority, not a single one of us were brought on because we were a woman, you know. And I think that that goes a long way to hiring people and keeping people around because everyone gets to feel valued for what they bring to the table, not just how they show up at that table.
20:57
Annie, Redpoint has clearly invested heavily in brand. And it seems they’ve encouraged their partners to do the same. Tom Tunguz is an old friend of the show, and he’s been on numerous times over the years. You know, he was doing blog posts. And of course, we’ve got Logan Bartlett’s pretty active on Twitter and other mediums. And now there’s Cartoon Avatars and a very, very popular TikTok account. It seems like the firm has placed some strategic emphasis on brand building and promotion across multiple platforms. Can you talk about the thought process behind this at Redpoint?
21:29
Yeah, so we view Redpoint as a startup, we run a lot of experiments. Right now, we are running a lot of external brand facing experiments. And so you are seeing them, you just talked about several of them. The last four years, we’ve actually been building and running a lot more internal experiments as it relates to how we look at our own data and how we structure our Founder Experience Team, which is our version of a platform team, how we add the most value to onboarding founders, creating plans with them being helpful to them in real ways that matter, as time goes on and they’re building their companies. And so, you know, how do we think about brand and marketing? You know, at the end of the day, all venture firms are the same and what they’re doing, they’re exchanging dollars for equity. How do you make a choice and who you want to work with? Most people I know, not just in venture not just in technology, but in business in general will say it matters, the people that you work with, and I really think it does in venture too. And so part of our exercise on the marketing side is how do we in some ways show what we all know, Redpoint is it’s why we’re here we operate as a true team. We believe venture can be and should be a team sport, as opposed to a group of individual players. And so some of the ideas to bring marketing to show that and also, you know, I think if I think of our TikTok account, it brings a little levity to a world that sometimes needs that.
22:49
I love it. I love it. Was there a time that it went from more of a self directed activity to kind of a firm priority?
22:55
Yeah, we’ve had a couple of people join our team in the last year or two. One is Josh Machiz who has previously spent 10 years as the Chief Digital Officer at NASDAQ. So he built up their brand, he was taking companies public, he built all their social followings. He’s now doing that for us here. For those of you who have seen TikTok, Rashad on our team is like hilarious and wonderful, joined us in the last year to do some of that, like actual content production. And so yes, we have, you know, leading up to those people joining us, we had spent a lot of time doing some iterations on our own learning about it, and then finding who do we think would be the best person to go and do this? And we’re going to put a very real financial investment behind it, because we do think it’s important.
23:40
Annie, what advice would you give your younger self, either general or as an investor?
23:46
I would say trust your gut, it’s usually more right than maybe you give it credit for or then you’re ready to believe. And I would say, pick great people every time period, you can apply that to a whole bunch of different different things. But for me, my greatest successes define that in any way you will, financial, personal, relational professional have all been because of the people. And the biggest misses that I have had have also been when I did not put the highest priority on the people.
24:19
I love it. It’s part of the reason why our firm here is still a generalist. Every time we’ve kind of picked specific theses and gone out and looked for teams and whatever. Sometimes we found the perfect business, but we just couldn’t quite get there on the team.
24:33
That’s so hard, isn’t it?
24:34
Yeah. Annie, it’s easy to get caught up in defining success as evaluation or some other metric, you know, how do you define success? And what do you think leads one to achieving it?
24:46
Oh, I think you know, the term success, I think can be oftentimes maybe normalized, or at least in the ponds in which I swim, with financial success, or in some times related to that fame of some kind. Might be real fame, like mainstream fame, I should say, like you’re on the cover of People magazine, it might be Twitter fame, or something else that’s important to you, whatever it is, it’s like a recognition. And that’s important to some people, it’s not particularly important to me. You know, success for me is getting to have an impact on positive impact on the most people on the planet. And I can tell myself a story about how the seat that I sit in gives me some opportunity to do so. You know, I think starting companies is one of the bravest and most challenging things that someone can spend their time doing.
25:32
Yeah.
25:33
And to be an early stage investor, which I often describe as peak excitement and peak brain damage phase of building a company is, you know, I like that I get to be in one part analytical decision maker, but more parts, you know, cheerleader, friend, confidant, I’m joining their teams and trying to help in in all ways, whether it’s operational, financial, sometimes just listening and trying to work through a problem that is a people problem first.
26:01
The psychology of this whole thing is often not really discussed, it ends up being a huge part of the job, I found.
26:09
Yeah, totally. And I think it’s something like you either get energy from that or you don’t, right. If I was not an early stage investor, there’s a nonzero chance that I would be like a psychiatrist or a coach. I love that stuff. Like I really do genuinely love working on hard problems and brainstorming with people. And the creative part of the journey of building a company from scratch is really, really hard and really, really rewarding when you get it right.
26:32
Awesome. Kind of a two part question: We’re seeing all these tweets, sort of catastrophizing the situation right now, and everyone should be doing layoffs and cutting burn and pulling back on spending and, and then the other side of the coin is deployment and investments and, you know, different firms having different reactions there. I’d be curious to hear what’s your position on the state of the market and how that has impacted your portfolio and the way that you work with them? And then also, on the investment front: are you all systems go? Are you taking a different approach right now?
27:05
I’ll answer your last question first. We’re all systems go.
27:08
Okay.
27:08
Especially on the early stage side, this is a, it’s an excellent time to start a company. It’s an excellent time to be an early stage investor. Your second question, or first question I’ll answer second, was my view on the state of the market and how it’s informing how we work with our portfolio companies today, I take a more longitudinal view on the market. If you look at the average valuation, the average deal size in the last 12 months and in the last three years, they are extraordinary outliers to what they have been in the last decade, do I think we’re going to go back to what you know, valuations looked like 10 years ago, or eight years ago? I don’t think so there’s just too many more dollars, frankly, available in the market for us to do that. But are we going to come down 50% Have we frankly, already come down 50%, from what we were last year, totally. And so I do think that the normalization of the market, it’s not even coming. It’s here, like we’re seeing in that early stage every day, it’s actually been pretty amazing to me, I’ve been, I don’t know, I guess just a bit shocked to kind of how quickly that has happened. But not now, I think it’s a good thing for companies and a good thing for investors, because it means that you can grow a company in a way that you actually get to be more thoughtful about it, and you’re not chasing growth at all costs. And you don’t have you know, instead of having 57 different competitors, because everyone else has gotten funded at the same time that you have, you might have three, and the numbers that you are trying to put up in order to raise your next round, are achievable in a way that you can achieve them and also grow your team in a way that it’s not going to break. So, you know, I’m quite excited about it. I think that it’s going to mean that early stage startups are exciting and fun. And, you know, I still think it’s the best place for people to start their career. The second question, sorry, that was a bit long winded about what how are we working with our portfolio companies, pretty much every portfolio company is re forecasting their plan right now. Some are doing so materially, you know, 50% 60% 70% changes, some are doing less, you know, 10 or 15%. But every single company, whether they are up into the right, growing like gangbusters, kind of right down the middle of the fairway or struggling because they for whatever number of reasons. Everybody is revisiting it based on this new market.
29:21
Yup. You had mentioned 50% before, is that directionally sort of the order of magnitude you’ve seen dropping in terms of round sizes and potentially valuations?
29:31
Yeah.
29:32
Yeah.
29:32
Yeah. But again, if I look at it over over the last 10 years, even the last seven years, right, I actually think about it as the inverse, right? It’s just that it popped 100% for two years, and now it’s come back. And so maybe that’s the half glass full way of looking at it. But I think there’s a reason that the market has existed in that way for a long time before that. It takes time to build teams and it takes time to build product and to get customers and those things are unchangeable at the earliest wages within a range of time and dollars. And so I think it’s gonna make building companies and being part of companies a whole lot more sustainable and rewarding for people than the last couple of years have been.
30:13
Constraints can breed creativity, right? Sometimes it’s healthy. Annie, if we can feature anyone here on the show, who do you think we should interview? And what topic would you like to hear them speak about?
30:26
Oh, that’s a great question. I’d love to hear from some people who were on the ground floor at Amazon, in their first few years there. Not Bezos necessarily, but you know, employee number 27, who saw the thing grow for the first six or seven years and the things that they did that were scalable and unscalable, and the debates and bickering that happened internally, if they were only selling books, or if they were gonna sell books and shoes, and also, you know, vacuum cleaners, or whatever else came next. Yeah, I think would be a really interesting perspective. So often, I think we interview and hear from the founders and senior executives that have built companies, but I actually think the early employees are often closer to the business, you know, in the portion or part of the businesses that they’re running. And those stories, you know, just by definition, like the number of people it would apply to, could be really interesting to hear.
31:21
Maybe less revisionist history, and in some of those stories, yeah.
31:24
You know, like, yeah, and also just even tactically too, right. Like, after you get to be, you know, 50, 60, 70 people, it’s impossible as a human being to be that deep on every part of your business. So to hear from the person who built the Amazon product from 20 people to 1000 people, and how they thought about product prioritization and what data was most interesting or available to them? You know, something like I think would be really interesting.
31:50
Annie, do you have any tools or hacks that are a secret weapon?
31:55
I keep a extraordinarily Type A color coded set of Google calendars, to run my life day to day. And I guess the hack there is applying some business operations mindset to my whole life personal and professional to lay out 100% of the things that need to get done, I also married an apparent and have a working partner. And there are too many things for us to both do. And so we have built some Google spreadsheets that are embarrassingly detailed, and have outlined kind of roles and responsibilities for everybody involved. And that has actually, helped us tremendously.
32:38
Amazing. Is part of it grouping activities, so there’s less context switching during the day?
32:43
Yeah! And also, I mean, it’s just like inside a company, you know, like when you like, end up having friction with people because you’re both kind of sort of sometimes doing the thing, right? And so instead, you’re like, okay, here are all the lists of things. This is, plan the food, buy the food, put the food away, throw the bags away, or put the reusable bags back, put things in the dishwasher, unload the dishwasher, make the food, put the dishes away, like all the things right, like just food as a topic is like 14 rows. I wish I was making this up, but I’m not. For dog, you have the same, for travel planning you have the same, for personal finances you have the same. My Google Doc has probably 85 rows in it. And then to be able to say column by column: this is yours, this is mine, this is you know, our nanny, this is something we can outsource and just making it really clear both so that we know it’s getting done but also to just have clear, like lines of responsibility has been really helpful, as silly as that sounds.
33:36
I love it. Well, mentally it’s so much easier to do something if you know it’s your responsibility. If it’s shared then it’s tricky.
33:42
Totally. And you don’t build up like little like micro resentments along the way.
33:48
Have you been speaking to my wife Annie? What’s going on?
33:51
This is a relationship podcast right?
33:54
And then finally here, Annie what’s the best way for listeners connect with you and follow along with Redpoint?
33:59
Well, you can find us on our social channels and or I’m just Annie at Redpoint.com Send me an email anytime.
34:05
Alright, she is Annie Kadavy, Managing Partner at Redpoint. Annie, thanks so much for the time, really enjoyed your insights and I can’t wait for the next one.
34:12
Thanks so much, Nick.

Transcribed by https://otter.ai

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342. Investing in $B+ Marketplaces, Beating the Cold Start Problem, Warby Parker’s Key to Scaling, and the Backstory Behind Redpoint’s Social Media Surge (Annie Kadavy)

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