The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

Aaron Hirschhorn argument clarity score 4.6/5 from 26 exchanges on raw tape · average scores: directness 5 · coherence 4.8 · precision 4.6 · compression 4.1 record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered raw tape D 5 · C 5 · P 5 · Cm 5 5.00

Q Now talk to me, what's the origin story for Dog Vacay? What really was the aha moment for you?

A The aha moment for, for our business was, uh, my wife and I traveled to the East Coast to visit our families and left our two dogs in a kennel in Los Angeles, where we currently live. And it was a ten-day trip. We came back to a 1400 dollar kennel bill, and my dog Rocky was traumatized hiding under my desk for three days after. And we said, oh my god, this is an awful experience for the dogs, an awful experience for the humans, and for the humans' wallet. There must be a better way. And that was when we began to take a look. Realize that the opportunity is massive. There's eighty-three million dogs in the U.S., which is more than there are kids, by the way. And the pet The pet services market is fifteen billion dollars in the U.S. and completely fragmented, where nobody has even a couple points of market share, so it's a wide open opportunity.

AI assessment note: “The aha moment for, for our business was, uh, my wife and I traveled”

Answered raw tape D 5 · C 5 · P 5 · Cm 5 5.00

Q And, and so I'm intrigued then, when you were building, um, Dog Vacay in the very early days, what was the, the harder element? Was it the demand or the supply side?

A To this day, um, so from the beginning and to this day, the demand side is harder, and I'll tell you why. Uh, if you think about the business, uh, on the supply side, you, the, our value proposition is sign up for free, make money watching puppies. And, uh, that's a very easy sell for most cases. So we have more applications than we know what to do with. We approve only about 15% of our, our dog sitter applications. On the demand side, where a dog is like your child, we're basically saying, hey, drop off your, uh, your, your child at a stranger's house and give us your credit card. Um, that's hard. Pulls in trust. Um, it pulls in a lot of challenges around a new business model, um, in an old world. So definitely more demand constrained, but as we've shown, you know, we've had product market fit since very early days and we've booked dog nights in the millions. So people are absolutely using the service and love it.

AI assessment note: “so from the beginning and to this day, the demand side is harder”

Answered raw tape D 5 · C 5 · P 5 · Cm 5 5.00

Q And you said there about the targeted list of investors. Is that kind of 15 or is that five for you?

A It's more than five. I'd say it's more than 15. For us, it was like 30. The VCs that you meet with first, those are the ones that you don't actually want in your deal. So what we did is we did first practice rounds with our own internal investors. Then we had a group of three or four for whatever series of reasons were not on the top of our list, but we put them first in the process. Because it gives you feedback, gives you real questions that you have to answer, then you're iterating and, you know, updating your investor deck, and then the guys you really want are like week three, and you stack all the guys you really want in week three, and that's sort of how we went about it. For the series A, I probably did 30 pitches.

AI assessment note: “It's more than five. I'd say it's more than 15. For us, it was like 30.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Now talk to me, what's the origin story for Dog Vacay? What really was the aha moment for you?

A The aha moment for, for our business was, uh, my wife and I traveled to the East Coast to visit our families and left our two dogs in a kennel in Los Angeles, where we currently live. And it was a ten-day trip. We came back to a 1400 dollar kennel bill, and my dog Rocky was traumatized hiding under my desk for three days after. And we said, oh my god, this is an awful experience for the dogs, an awful experience for the humans, and for the humans' wallet. There must be a better way. And that was when we began to take a look. Realize that the opportunity is massive. There's eighty-three million dogs in the U.S., which is more than there are kids, by the way. And the pet The pet services market is fifteen billion dollars in the U.S. and completely fragmented, where nobody has even a couple points of market share, so it's a wide open opportunity.

AI assessment note: “The aha moment for, for our business was, uh, my wife and I traveled”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And I'm really pleased you mentioned unit economics there, because I want to move on to discuss kind of the on-demand economy more on the whole now. And, and we've seen the on-demand economy evolve. And so I want to ask what businesses do you think fundamentally work in the on-demand economy and what don't from your perspective?

A Yeah, it's a fair question. I mean, I think we're starting to see a blend between people calling it on demand, and sharing economy, and marketplaces, and the ones that I am most excited about, the ones that I think have the highest probability of success, are those that offer a better product or a better experience at a lower price. And probably the best example of that is, is UberX. Not the core Uber product, but UberX, where It is a better experience than a taxi by far, and more affordable. And then, of course, selfishly, I'll put a dog vacay in that category, where we offer a far better experience than the kennel, and at about 40% less, on average, of, of cost. Um, the businesses that may be very successful, but I don't think will be as huge, are those that charge a premium for convenience. That's not new. Like, rich people have always been able to get Things easier and quicker by paying for it. And so some of the delivery businesses, deliveries existed. Are you making it better? Yes. But are you charging a lot for it? Yes. And I think there's, there's not going to be as much room for so many players. I think when you're talking about something that actually makes your life better and saves money, that those are the businesses that have massive potential to, to grow. That being said, The unit economics have to be right, and what you saw last year, of course, was incredible f…

AI assessment note: “ones that I think have the highest probability of success, are those that offer a better product”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And you said there about the targeted list of investors. Is that kind of 15 or is that five for you?

A It's more than five. I'd say it's more than 15. For us, it was like 30. The VCs that you meet with first, those are the ones that you don't actually want in your deal. So what we did is we did first practice rounds with our own internal investors. Then we had a group of three or four for whatever series of reasons were not on the top of our list, but we put them first in the process. Because it gives you feedback, gives you real questions that you have to answer, then you're iterating and, you know, updating your investor deck, and then the guys you really want are like week three, and you stack all the guys you really want in week three, and that's sort of how we went about it. For the series A, I probably did 30 pitches.

AI assessment note: “It's more than five. I'd say it's more than 15. For us, it was like 30.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q do you think then, we spoke about those incredible metrics kind of three months in, at what moment do you think Dog Vacate turned from Potentially a fluffy business maybe, that might be incredibly harsh, and I'm so sorry for that, to kind of an incredible behemoth backed by the likes of Benchmark and First Round. When did that really transition, do you think, in the minds of the public?

A Well, I appreciate, I, I don't think we're quite a behemoth yet, but, um, I believe we're, we're on the right path. To your point, as I was pitching this concept, I got a lot of laughs. People were like, you know, come on, I'm a, I'm a serious VC. Why are you bringing me a dog sitting business? You know, I, I think one thing that, that did help early on is that I had actually watched over a hundred dogs in my home over the course of 20 11 being the dog sitter, being the very first dog vacay Um, sitter. And so I lived it. And so there were the two or three people that got it, you know, Mike Jones over at science, Howard Morgan at first round, getting a little bit of that early credibility made a huge difference because it, it meant that we weren't, you know, we got credible people behind us. And so that's one win, but ultimately it was about the growth and going from zero to several 100,000 in, in gross bookings in a few months, then, you know, it became a fairly easy series. Day story for, for the subset of people who understood it. I still have a lot of people who chuckled. I had a lot of people who said, Hey, come on, this is dog. Same story. But, um, Benchmark and Bill Gurley were believers in, in the market opportunity and all the great things you can do once you build the trust of pet owners in general. So, and then once Benchmark came in, it became even more easy, if you …

AI assessment note: “ultimately it was about the growth and going from zero to several 100,000”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And, and so I'm intrigued then, when you were building, um, Dog Vacay in the very early days, what was the, the harder element? Was it the demand or the supply side?

A To this day, um, so from the beginning and to this day, the demand side is harder, and I'll tell you why. Uh, if you think about the business, uh, on the supply side, you, the, our value proposition is sign up for free, make money watching puppies. And, uh, that's a very easy sell for most cases. So we have more applications than we know what to do with. We approve only about 15% of our, our dog sitter applications. On the demand side, where a dog is like your child, we're basically saying, hey, drop off your, uh, your, your child at a stranger's house and give us your credit card. Um, that's hard. Pulls in trust. Um, it pulls in a lot of challenges around a new business model, um, in an old world. So definitely more demand constrained, but as we've shown, you know, we've had product market fit since very early days and we've booked dog nights in the millions. So people are absolutely using the service and love it.

AI assessment note: “from the beginning and to this day, the demand side is harder”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And I mean, I'm intrigued there because it takes, um, a beating when you get Uh, laughed at by VCs, as you say. So how did you take that as the founder at the time? How did you not let it dampen morale?

A I mean, it did a little bit. I, I had spent a little bit of time, about a, a year and a half, two years, um, on the VC side myself, so I saw that most deals didn't get funded, and I went in with a fairly sober view of knowing that, you know, your hit rate's gonna be relatively low. Um, I do think the thing that helped was people saw my passion, and they saw that I actually lived the business. It came from a real experience. You know, every time you get just a little win, even if it's early, a 25,000 dollar check, That's very buoying, and it was very exciting, and so, um, you just keep plowing forward, and I think the most important thing, and I always tell this to early founders, is like, you just have to keep showing momentum, even if you keep getting rejected, if the business shows some momentum, if you release a new product, if you've got a new customer, whatever the thing is, there's nothing better than that, for yourself to feel better, for investors to ultimately feel better.

AI assessment note: “I mean, it did a little bit... every time you get just a little win”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Um, okay. So if you could start the process again and change one thing, it could be anything. It could be the first site design or it could be your investors. No, I'm just kidding. What would you change?

A One thing I would change is I would be much smarter about how to build the initial infrastructure of the site. We're still working out, working through Through a lot of technical debt. And you hear that a lot. You hear a lot of companies say you always have to throw away the first version. Because I had such a concept that most people chuckled at, because I was a first-time entrepreneur, I simply couldn't find anybody good. And I remember going on to, it was Odesk at the time. It was one of these, uh, you know, freelance work platforms. It's now Upwork. I had, I had one guy in Guatemala coding my site, another guy in Armenia, a designer in India, cobbled the thing together, two different languages. It was a disaster. And, you know, I would have just gotten Better at finding someone good and making smart architecture decisions, so we wouldn't still be tiptoeing around elements of the code. But it's not, um, it's not an uncommon thing to hear where even very, very smart guys who know a lot about engineering, the V-one of the product ends up being quite different from what the business, um, ends up focusing on, and so you ultimately make choices around rebuilding or keeping what you've got. I would have just done something a lot smarter in the, out of the gate. It would Be allowing us to move faster even today, four years later.

AI assessment note: “One thing I would change is I would be much smarter about how to build”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q I'm really intrigued that you said about product market fit and it's always an interesting topic because you never, you know, you don't get an email certificate saying you've achieved product market fit. So how did you, how did you know that this was truly market validated and you had achieved that?

A Well, I mean, it's interesting. We launched in March of 2012, and I think the first month we must have had, you know, just three or four bookings, but people started talking about it, and the next thing we knew, three months in, we were doing a few 100,000 dollars a month. Um, people hate the kennel. They hate paying 50, 60 dollars a night to leave their dog in a cage, and as people discovered this, um, word of mouth took off. And so I think it was, it was early traction, early revenue, and just seeing that People were coming in from word of mouth was the biggest indication that we had something that was working. Now, we made lots of mistakes. We continue to make lots of mistakes, but the core of the business hasn't changed. You know, people watch dogs in their home, loving attention instead of being stuck in the cage at the kennel.

AI assessment note: “word of mouth was the biggest indication that we had something that was working.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And so brilliant you mentioned Unity Economics there, because I always feel now it's bandied around kind of like cash in the bubble. Right. So, so how do you think marketplace founders should be approaching the issue of Unity Economics with regards to growth, and should growth still be the priority, do you think?

A Yeah, I mean, it depends on the, on the, it depends on your business and the market. Obviously, I can speak most, with most detail about our, our industry. If we look at pet services, you know, we're still scratching the surface in terms of market penetration. So we're the leader in the space, but have a market share of, you know, 50 basis points, less than one percent. So in that, in that sense, yes, you need to, you need to be chasing growth. You have to do it sustainably, and I think that's the discipline that we've had. You know, Bill Gurley's on our board from Benchmark, and He's been saying for pretty much as long as I've known him that, uh, the bubble is going to burst, and he turned out to be right about three years later. We've looked at and had strong unit economics from early on. You've got to make it work. You've got to build a sustainable business, and that's just a matter of finding the right balance. You know, do you charge the demand side? Do you charge the supply side? Which side is more scarce? So for example, because supply is a little bit easier for us to get than demand, which we talked about, We'll charge the supply more money. Um, other businesses might be different where the demand is, is harder to get or easier to get. You might charge the demand side more. So it really depends, um, how you figure that out, how you split costs and, uh, between the two s…

AI assessment note: “yes, you need to, you need to be chasing growth. You have to do it sustainably”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q I'm really intrigued that you said about product market fit and it's always an interesting topic because you never, you know, you don't get an email certificate saying you've achieved product market fit. So how did you, how did you know that this was truly market validated and you had achieved that?

A Well, I mean, it's interesting. We launched in March of 2012, and I think the first month we must have had, you know, just three or four bookings, but people started talking about it, and the next thing we knew, three months in, we were doing a few 100,000 dollars a month. Um, people hate the kennel. They hate paying 50, 60 dollars a night to leave their dog in a cage, and as people discovered this, um, word of mouth took off. And so I think it was, it was early traction, early revenue, and just seeing that People were coming in from word of mouth was the biggest indication that we had something that was working. Now, we made lots of mistakes. We continue to make lots of mistakes, but the core of the business hasn't changed. You know, people watch dogs in their home, loving attention instead of being stuck in the cage at the kennel.

AI assessment note: “it was early traction, early revenue, and just seeing that People were coming in”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And so brilliant you mentioned Unity Economics there, because I always feel now it's bandied around kind of like cash in the bubble. Right. So, so how do you think marketplace founders should be approaching the issue of Unity Economics with regards to growth, and should growth still be the priority, do you think?

A Yeah, I mean, it depends on the, on the, it depends on your business and the market. Obviously, I can speak most, with most detail about our, our industry. If we look at pet services, you know, we're still scratching the surface in terms of market penetration. So we're the leader in the space, but have a market share of, you know, 50 basis points, less than one percent. So in that, in that sense, yes, you need to, you need to be chasing growth. You have to do it sustainably, and I think that's the discipline that we've had. You know, Bill Gurley's on our board from Benchmark, and He's been saying for pretty much as long as I've known him that, uh, the bubble is going to burst, and he turned out to be right about three years later. We've looked at and had strong unit economics from early on. You've got to make it work. You've got to build a sustainable business, and that's just a matter of finding the right balance. You know, do you charge the demand side? Do you charge the supply side? Which side is more scarce? So for example, because supply is a little bit easier for us to get than demand, which we talked about, We'll charge the supply more money. Um, other businesses might be different where the demand is, is harder to get or easier to get. You might charge the demand side more. So it really depends, um, how you figure that out, how you split costs and, uh, between the two s…

AI assessment note: “yes, you need to, you need to be chasing growth. You have to do it sustainably”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q do you think then, we spoke about those incredible metrics kind of three months in, at what moment do you think Dog Vacate turned from Potentially a fluffy business maybe, that might be incredibly harsh, and I'm so sorry for that, to kind of an incredible behemoth backed by the likes of Benchmark and First Round. When did that really transition, do you think, in the minds of the public?

A Well, I appreciate, I, I don't think we're quite a behemoth yet, but, um, I believe we're, we're on the right path. To your point, as I was pitching this concept, I got a lot of laughs. People were like, you know, come on, I'm a, I'm a serious VC. Why are you bringing me a dog sitting business? You know, I, I think one thing that, that did help early on is that I had actually watched over a hundred dogs in my home over the course of 20 11 being the dog sitter, being the very first dog vacay Um, sitter. And so I lived it. And so there were the two or three people that got it, you know, Mike Jones over at science, Howard Morgan at first round, getting a little bit of that early credibility made a huge difference because it, it meant that we weren't, you know, we got credible people behind us. And so that's one win, but ultimately it was about the growth and going from zero to several 100,000 in, in gross bookings in a few months, then, you know, it became a fairly easy series. Day story for, for the subset of people who understood it. I still have a lot of people who chuckled. I had a lot of people who said, Hey, come on, this is dog. Same story. But, um, Benchmark and Bill Gurley were believers in, in the market opportunity and all the great things you can do once you build the trust of pet owners in general. So, and then once Benchmark came in, it became even more easy, if you …

AI assessment note: “once Benchmark came in, it became even more easy, if you will”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q And I'm really pleased you mentioned unit economics there, because I want to move on to discuss kind of the on-demand economy more on the whole now. And, and we've seen the on-demand economy evolve. And so I want to ask what businesses do you think fundamentally work in the on-demand economy and what don't from your perspective?

A Yeah, it's a fair question. I mean, I think we're starting to see a blend between people calling it on demand, and sharing economy, and marketplaces, and the ones that I am most excited about, the ones that I think have the highest probability of success, are those that offer a better product or a better experience at a lower price. And probably the best example of that is, is UberX. Not the core Uber product, but UberX, where It is a better experience than a taxi by far, and more affordable. And then, of course, selfishly, I'll put a dog vacay in that category, where we offer a far better experience than the kennel, and at about 40% less, on average, of, of cost. Um, the businesses that may be very successful, but I don't think will be as huge, are those that charge a premium for convenience. That's not new. Like, rich people have always been able to get Things easier and quicker by paying for it. And so some of the delivery businesses, deliveries existed. Are you making it better? Yes. But are you charging a lot for it? Yes. And I think there's, there's not going to be as much room for so many players. I think when you're talking about something that actually makes your life better and saves money, that those are the businesses that have massive potential to, to grow. That being said, The unit economics have to be right, and what you saw last year, of course, was incredible f…

AI assessment note: “the ones that I think have the highest probability of success, are those that offer a better product”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q And I mean, I'm intrigued. How do you approach transparency with that competitive edge of fundraising? Do you say, oh, benchmark, you know, a very closing in on it to first round? Do you make that obvious?

A I don't, you know, they all know. They all talk to each other. Um, it's remarkable how much on Sandhill Road these guys know what's going on. They see that you're, You know, going from one meeting to another. So you, you don't even really need to do that. Um, and they see at some point you say, look, they might say, Hey, we're a very common question that I would get is, Hey, where are you in the process? And I, you know, then I might say, Oh, we're very early or look, we're fairly far along. We've got a lot of interest or like, yeah, we, we've got a couple of term sheets. And I think it really just depends on the situation. What, what and how you want to share with that information. Um, but by and large, it definitely helps the investors write a check to know that you've got other people courting you.

AI assessment note: “I don't, you know, they all know. They all talk to each other.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q And I'm really intrigued, what made you want and then not want a set of investors? Obviously no names at all, but, but what were the kind of key attributes that made you go benchmark are the ones we want and X are not?

A Um, domain expertise is important. So we're, we're building a marketplace business, and so anybody who had experience, um, and marketplaces are far more common now than they were four years ago, so it's still relatively early. Anybody that had experience with that was, was very important. We, I did like having credibility, so getting kind of a tier one VC, um, if possible is always good. They're both smarter, have deeper networks, and Again, give credibility for what seems like a silly business to people looking externally. And then, of course, there's the numbers. I mean, people are writing different size checks at different valuations, and those are very real considerations. So I don't think there's a single thing that you look at. It's a combination of all those factors. But that's if you're lucky to have the choice. And we were fortunate to have the choice back then. I don't know that that's always going to be the case. If there is, uh, you know, if there's, if there's food on the plate, then you should eat it. Um, so if someone's giving you money, I wouldn't turn it down.

AI assessment note: “domain expertise is important... credibility... there's the numbers.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Um, okay. So if you could start the process again and change one thing, it could be anything. It could be the first site design or it could be your investors. No, I'm just kidding. What would you change?

A One thing I would change is I would be much smarter about how to build the initial infrastructure of the site. We're still working out, working through Through a lot of technical debt. And you hear that a lot. You hear a lot of companies say you always have to throw away the first version. Because I had such a concept that most people chuckled at, because I was a first-time entrepreneur, I simply couldn't find anybody good. And I remember going on to, it was Odesk at the time. It was one of these, uh, you know, freelance work platforms. It's now Upwork. I had, I had one guy in Guatemala coding my site, another guy in Armenia, a designer in India, cobbled the thing together, two different languages. It was a disaster. And, you know, I would have just gotten Better at finding someone good and making smart architecture decisions, so we wouldn't still be tiptoeing around elements of the code. But it's not, um, it's not an uncommon thing to hear where even very, very smart guys who know a lot about engineering, the V-one of the product ends up being quite different from what the business, um, ends up focusing on, and so you ultimately make choices around rebuilding or keeping what you've got. I would have just done something a lot smarter in the, out of the gate. It would Be allowing us to move faster even today, four years later.

AI assessment note: “One thing I would change is I would be much smarter about how to build”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q And I mean, I'm intrigued there because it takes, um, a beating when you get Uh, laughed at by VCs, as you say. So how did you take that as the founder at the time? How did you not let it dampen morale?

A I mean, it did a little bit. I, I had spent a little bit of time, about a, a year and a half, two years, um, on the VC side myself, so I saw that most deals didn't get funded, and I went in with a fairly sober view of knowing that, you know, your hit rate's gonna be relatively low. Um, I do think the thing that helped was people saw my passion, and they saw that I actually lived the business. It came from a real experience. You know, every time you get just a little win, even if it's early, a 25,000 dollar check, That's very buoying, and it was very exciting, and so, um, you just keep plowing forward, and I think the most important thing, and I always tell this to early founders, is like, you just have to keep showing momentum, even if you keep getting rejected, if the business shows some momentum, if you release a new product, if you've got a new customer, whatever the thing is, there's nothing better than that, for yourself to feel better, for investors to ultimately feel better.

AI assessment note: “I mean, it did a little bit. I, I had spent a little bit”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q And then when you look back at the fundraising process now over several rounds, uh, what were your mistakes, do you think, and, and what would you do differently if you were to raise again, potentially with a new startup, say?

A I don't know that I, I don't know that, I mean, I think because I got such great guidance from these guys, uh, especially Peter and Mike and, and Bill, who all have very similar philosophies to how their company should best fundraise by creating these competitive processes, I don't know that I would do anything different. Look, at the end of the day, it's all about your business, and if your business is doing well, and your unit economics are good, and your growth is good, you'll figure out a way to get funding, even in a, even in a shitty market. And if it's not, you're going to have trouble. So, you know, you can optimize and make yourself, give yourself a chance for a better shot. If the business isn't working, it doesn't matter anyway.

AI assessment note: “I don't know that I would do anything different.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q So I've got two big questions to ask that. Firstly, uh, I have to ask, what's it like having, uh, the main man, Bill Gurley as a board member?

A He is, uh, extraordinarily smart. Uh, you know, it certainly is, is funny for me to think about him being on public company boards, uh, being on the board of Uber valued at sixty billion dollars, and then coming into our, uh, board meeting, and there's dogs running around, and You know, board slides have pictures of puppies, and so he tolerates it. But at the end of the day, you know, it's, it's all business. Bill's incredibly smart and just ultimately wants to win and will do anything that it takes to win, and he's been great. I've learned a ton. We've made a lot of smarter decisions having him On board, and, uh, he's a great advocate for the business.

AI assessment note: “he's been great. I've learned a ton. We've made a lot of smarter decisions”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q And then I want to finish on a personal intrigue question, and that's, what's the most interesting user behavior you've seen from watching your customers use Dog Vacay?

A The most interesting thing about our site is the fact that in order for the trust to really happen, most people want to meet in advance. And so you've got this unusual dynamic where in the on-demand world, people are used to pressing buttons and getting what they want. And you can use our service that way. We have instant book features, but you're talking about dogs and dogs. You want to know that this person is a good, is going to do a good job caring for your dog. You're going to trust them. You're going to see their house. You also have dynamics where are, is your dog going to get along with their dogs? Is your dog going to get along with other dogs that they're watching at the time doing our best, but not have, have certainly not cracked this code of how do we support and figure out this meet and greet and support People meeting in the real world and discussing these things back and forth while still staying on the platform. And so people do all sorts of crazy things where they're introducing dogs to each other. And it's just a bizarre way to think about how an internet or tech company can have a role in that facilitating like dog socialization. We'll figure it out someday, but it is not straightforward.

AI assessment note: “most people want to meet in advance”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q And I mean, I'm intrigued. How do you approach transparency with that competitive edge of fundraising? Do you say, oh, benchmark, you know, a very closing in on it to first round? Do you make that obvious?

A I don't, you know, they all know. They all talk to each other. Um, it's remarkable how much on Sandhill Road these guys know what's going on. They see that you're, You know, going from one meeting to another. So you, you don't even really need to do that. Um, and they see at some point you say, look, they might say, Hey, we're a very common question that I would get is, Hey, where are you in the process? And I, you know, then I might say, Oh, we're very early or look, we're fairly far along. We've got a lot of interest or like, yeah, we, we've got a couple of term sheets. And I think it really just depends on the situation. What, what and how you want to share with that information. Um, but by and large, it definitely helps the investors write a check to know that you've got other people courting you.

AI assessment note: “I don't, you know, they all know. They all talk to each other.”

Answered raw tape D 5 · C 4 · P 4 · Cm 3 4.15

Q And then when you look back at the fundraising process now over several rounds, uh, what were your mistakes, do you think, and, and what would you do differently if you were to raise again, potentially with a new startup, say?

A I don't know that I, I don't know that, I mean, I think because I got such great guidance from these guys, uh, especially Peter and Mike and, and Bill, who all have very similar philosophies to how their company should best fundraise by creating these competitive processes, I don't know that I would do anything different. Look, at the end of the day, it's all about your business, and if your business is doing well, and your unit economics are good, and your growth is good, you'll figure out a way to get funding, even in a, even in a shitty market. And if it's not, you're going to have trouble. So, you know, you can optimize and make yourself, give yourself a chance for a better shot. If the business isn't working, it doesn't matter anyway.

AI assessment note: “I don't know that I would do anything different.”

Answered raw tape D 4 · C 4 · P 4 · Cm 4 4.00

Q And then the second question from that, uh, was, you said there are about 50 basis points in less than one percent of the market. So what do you think will be the enabler for you to really achieve that market penetration that you desire?

A Uh, you know, it's an, it's a new concept still. Um, and I think these things take time, and especially ours where it's a highly trust-based business. I mean, they're, you know, this is not, uh, delivering dim sum If somebody messes up my Chinese food order, it's not the end of the day. If somebody messes up caring for my dog, that's a problem. There is an element of this is going to take a little while. All the more reason why the unit economics have to be strong and sustainable. The excuse the pun, you know, we're facing tailwinds, right? So people are more and more comfortable doing things this way, buying services online, on mobile, um, trusting strangers with things because they're confident in the company and the brand's ability to vet and provide qualities. All those things help. There's no secret to it. This is just execution, and it's about analytics. It's about making your, um, customer acquisition cost less than your lifetime value of your customers, uh, understanding how to improve the conversion rate. I think that's probably one of the, the least understood and least appreciated, um, levers of growth that you have for marketing. And a lot of people talk about optimizing Facebook ads, optimizing ads, doing TV. If you don't have a good conversion rate, if you have a leaky funnel, if your product's not good, none of that matters. So most of the leverage that you get, …

AI assessment note: “This is just execution, and it's about analytics.”

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