The Exchanges

Q Can I ask, often I hear on the show founders say, you know, seed is where you present the vision and series A is time for the data. Did you find that? And how did you see the rounds differ with each progressive round? Yeah.

A So it was a little bit different for me, but not too far off. So with series seed, I had actually bootstrapped the business for about eight months. And the reason why is because I started speaking to people early on and I found that they just didn't get the business. Um, it was mostly middle-aged men who I was talking to, and they would taste one of our first collections, which was smoothies, and they'd be like, it doesn't taste like Jamba juice. That's what I think a smoothie should taste like. I'm not sure that this is a thing. Frozen food, what are you doing? They just didn't get it. Like, when I kind of shared the big vision, they thought I was a dreamer. I went to bootstrap for the first eight months, and I proved our series seed with numbers, not a large amount of numbers, just enough to kind of show the traction. And then series A, we were actually pretty robust with our reporting.

AI assessment note: “So it was a little bit different for me, but not too far off.”

Q No, absolutely. I'm really pleased you touched on the capital efficiency element there, because I spoke to your board member, Beth, at first mark last night, and she mentioned that you raised very little in the seed in the A round. So I'm intrigued in the world where capital maybe isn't such a limiter today. Why did you choose this decision? Let's start with that.

A Yeah, so I think that capital efficiency is something that can be part of the core values of a company or not. And for me, coming from guilt and also believing that it is possible to do more with less, you know, wanted that to be part of our core culture. But I also, before we were ready to really open the floodgates and do all of the things that we initially set out to do, I'm a very big believer in kind of testing and learning and being really disciplined. So being Capital Light allowed us, or not only allowed us, it forced us to kind of be very selective with things that we went after and And to be methodical about how we did it.

AI assessment note: “wanted that to be part of our core culture”

Q Can I ask, often I hear on the show founders say, you know, seed is where you present the vision and series A is time for the data. Did you find that? And how did you see the rounds differ with each progressive round? Yeah.

A So it was a little bit different for me, but not too far off. So with series seed, I had actually bootstrapped the business for about eight months. And the reason why is because I started speaking to people early on and I found that they just didn't get the business. Um, it was mostly middle-aged men who I was talking to, and they would taste one of our first collections, which was smoothies, and they'd be like, it doesn't taste like Jamba juice. That's what I think a smoothie should taste like. I'm not sure that this is a thing. Frozen food, what are you doing? They just didn't get it. Like, when I kind of shared the big vision, they thought I was a dreamer. I went to bootstrap for the first eight months, and I proved our series seed with numbers, not a large amount of numbers, just enough to kind of show the traction. And then series A, we were actually pretty robust with our reporting.

AI assessment note: “So it was a little bit different for me, but not too far off.”

Q No, absolutely. I'm really pleased you touched on the capital efficiency element there, because I spoke to your board member, Beth, at first mark last night, and she mentioned that you raised very little in the seed in the A round. So I'm intrigued in the world where capital maybe isn't such a limiter today. Why did you choose this decision? Let's start with that.

A Yeah, so I think that capital efficiency is something that can be part of the core values of a company or not. And for me, coming from guilt and also believing that it is possible to do more with less, you know, wanted that to be part of our core culture. But I also, before we were ready to really open the floodgates and do all of the things that we initially set out to do, I'm a very big believer in kind of testing and learning and being really disciplined. So being Capital Light allowed us, or not only allowed us, it forced us to kind of be very selective with things that we went after and And to be methodical about how we did it.

AI assessment note: “wanted that to be part of our core culture. But I also... testing and learning”

Q Yeah, no, absolutely. I mean, you said about the site there. I read in an article On you about the site going down once, uh, and it made me think when the shit hits the fan, so to speak like that, how do you deal with it as a first time founder?

A Yeah, well, when it happened the first time, it was due to the fact that we were on a non-proprietary site, and it just wasn't meant for the scale that we had reached. So it's one of those moments where sheer panic and Susan, you're trying to figure out like, okay, I have a very Basic business problem that I need to solve right now. How do I charge people for what they're buying or what they're getting? And for me, the thing that I always go back to is stoicism or stoic philosophy. And I always ask myself, what's the absolute worst thing that can happen? So, you know, in that moment I said, okay, well, worst case scenario, people don't get charged. It's one week. Like, what does that really mean? And it was something that I could live with because the total number was something that it was a high number, but it wasn't catastrophic. It We ended up manually charging everybody, but the worst case scenario was one that I could live with, and that's usually how I look at these scenarios, and I kind of go to one total extreme, and generally I can live with the outcome, so it definitely helps center and calm the oh shit moments.

AI assessment note: “the thing that I always go back to is stoicism or stoic philosophy”

Q Yeah, no, absolutely. I mean, you said about the site there. I read in an article On you about the site going down once, uh, and it made me think when the shit hits the fan, so to speak like that, how do you deal with it as a first time founder?

A Yeah, well, when it happened the first time, it was due to the fact that we were on a non-proprietary site, and it just wasn't meant for the scale that we had reached. So it's one of those moments where sheer panic and Susan, you're trying to figure out like, okay, I have a very Basic business problem that I need to solve right now. How do I charge people for what they're buying or what they're getting? And for me, the thing that I always go back to is stoicism or stoic philosophy. And I always ask myself, what's the absolute worst thing that can happen? So, you know, in that moment I said, okay, well, worst case scenario, people don't get charged. It's one week. Like, what does that really mean? And it was something that I could live with because the total number was something that it was a high number, but it wasn't catastrophic. It We ended up manually charging everybody, but the worst case scenario was one that I could live with, and that's usually how I look at these scenarios, and I kind of go to one total extreme, and generally I can live with the outcome, so it definitely helps center and calm the oh shit moments.

AI assessment note: “for me, the thing that I always go back to is stoicism or stoic philosophy”

Q And tell me, Guilt Group, obviously an incredibly well-known institution, what were the core takeaways from being inside and really seeing the workings, and maybe how has that influenced your starting and running of Daily Harvest today?

A So Guilt Group was a very interesting organism, and there's just so much entrepreneurship and innovation that's come out of there, and I think the reason why is Is because guilt group really was such a pioneer in e-commerce one point O almost. And you know, there, there are definitely a few takeaways that if you've got a bunch of former guilt folks around a table, everybody would probably have in common. And it's very much informed how the group has built their own startups, you know, and for me in particular, it's informed how I've deployed capital, how I look at growth, how I look at team building. And it's nothing against guilt. As I said, it was absolutely a pioneer, but it's As I built Daily Harvest, I really looked at building it very capital efficient, not hiring six months ahead of growth, and just some learnings from the record speed Hit a peak and went down from there.

AI assessment note: “building it very capital efficient, not hiring six months ahead of growth”

Q So you've had this incredible experience kind of bootstrapping to then raising an unconventional round and then maybe a more conventional round with light speed and a bigger raise. I'm intrigued. Say you're angel investing in me and advising me. What would you advise me in terms of going out to fundraise from seed to series A? What would be the core tips for me personally?

A So I would actually say that throughout series C and series A, there were a lot of learnings for me, and I deployed those learnings in my series B. So, you know, what I would say is my series B, I think, was my most flawlessly executed round, and, you know, I would give the advice to do it this way. So this way is, you know, really what I did is I did a lot of quote-unquote dating before I set out to raise. So I met with VCs, Anybody who wanted a meeting, I took, I went out to a few that I heard great things about, and I just got to know them. It was probably a little untraditional for me not to share anything about the business. I didn't share one number. I just kind of shared the big picture, and I, you know, I was very explicit that my plan was to raise in the fall, and that at that point, I would go forward with a few suitors that I felt Were the best matches for me. One of the things that was super important to me was to find investors that were value aligned, but also I'm a single founder. So for me, my board and my investors are a little bit more important than I think if you have a co-founder. So it was really important I actually went out for the round. I only went out to six VCs, and I'd already had relationships. I already knew that I wanted to work with them, and I ran a true process, but in such a short period of time. First, instead of that six weeks that the othe…

AI assessment note: “I did a lot of quote-unquote dating before I set out to raise”

Q No, absolutely. I very much live by the same philosophy. I'm intrigued. You said about the extremes there. Going from very capital efficient to the recent light speed round, and now raising over forty three million dollars in funding. I'm intrigued. What was the cap Capitalist that really made you think now's the time to raise that big round?

A Yeah, so it was actually all very deliberately orchestrated, where Series C and Series A, I wanted to be really capital efficient. We had a lot of things to prove, and I wanted to make sure that when it came time for the Series B, that we're going to be able to raise the amount of money that I knew we needed to really do all the things that I envisioned when starting the business, and in order to You can't just raise forty three million dollars because you want to. So, you know, by being really lean in the beginning and being really disciplined, uh, we were able to do it. So it was all part of the plan from the beginning. And, you know, I just feel like really lucky that we were, we were actually able to see things play out as we had originally dreamed.

AI assessment note: “it was actually all very deliberately orchestrated”

Q founder status and how it means more with the investors and the board. I always hear from a lot of founders that the biggest thing an investor can add is empathy. What to you is the single biggest element an investor can provide? Is it empathy or is it actually strategic partnerships, capital, experiencing go-to-market? What would it be for you that attracts, say, Alex at Lightspeed over someone else?

A Yeah. So for me, you know, so Alex at Lightspeed and Carl's From BMG are both on my board, and you know, I have such a wonderful relationship with them, and I, the main reason why I kind of went through this whole courtship process and then decided that they were going to be part of this final round was definitely because we had an incredible relationship kind of forming, and I knew that when it came time for board conversations, but also when it came time for, you know, just a one-off, that I would have their ear. I would have that empathy, but I would also have them as a sounding board. Both Alex and Carl be the type of people that I can call. I can be a little vulnerable with, you know, I can, I will get that empathy, but they're also just wonderful sounding boards. So the decisions that one would usually make with a co-founder, I find that if I just call Alex or call Carl and have one of those conversations that, you know, I usually come up with a really wonderful solution for anything.

AI assessment note: “I would have that empathy, but I would also have them as a sounding board.”

Q And tell me, Guilt Group, obviously an incredibly well-known institution, what were the core takeaways from being inside and really seeing the workings, and maybe how has that influenced your starting and running of Daily Harvest today?

A So Guilt Group was a very interesting organism, and there's just so much entrepreneurship and innovation that's come out of there, and I think the reason why is Is because guilt group really was such a pioneer in e-commerce one point O almost. And you know, there, there are definitely a few takeaways that if you've got a bunch of former guilt folks around a table, everybody would probably have in common. And it's very much informed how the group has built their own startups, you know, and for me in particular, it's informed how I've deployed capital, how I look at growth, how I look at team building. And it's nothing against guilt. As I said, it was absolutely a pioneer, but it's As I built Daily Harvest, I really looked at building it very capital efficient, not hiring six months ahead of growth, and just some learnings from the record speed Hit a peak and went down from there.

AI assessment note: “building it very capital efficient, not hiring six months ahead of growth”

Q Kat, being practical, what did you prioritize given the capital light structure, and then what did you sacrifice?

A Yeah, so I would say we've prioritized, I mean, everything that we've done has been ordered, and I'd say, you know, executed in that order. So, things like team growth to be able to, to build our own proprietary site, you know, that's something that we didn't prioritize. We knew we could use Kind of an out-of-the-box solution, which was very not out-of-the-box by the time we were done with it, but an out-of-the-box solution to start and, you know, then got to a point where, where we were, we were breaking it, you know, and then built our own site. And one of the downsides to that was there were a few features that we really wanted our customers to have that we couldn't ship to them for some time.

AI assessment note: “things like team growth to be able to, to build our own proprietary site”

Q So you've had this incredible experience kind of bootstrapping to then raising an unconventional round and then maybe a more conventional round with light speed and a bigger raise. I'm intrigued. Say you're angel investing in me and advising me. What would you advise me in terms of going out to fundraise from seed to series A? What would be the core tips for me personally?

A So I would actually say that throughout series C and series A, there were a lot of learnings for me, and I deployed those learnings in my series B. So, you know, what I would say is my series B, I think, was my most flawlessly executed round, and, you know, I would give the advice to do it this way. So this way is, you know, really what I did is I did a lot of quote-unquote dating before I set out to raise. So I met with VCs, Anybody who wanted a meeting, I took, I went out to a few that I heard great things about, and I just got to know them. It was probably a little untraditional for me not to share anything about the business. I didn't share one number. I just kind of shared the big picture, and I, you know, I was very explicit that my plan was to raise in the fall, and that at that point, I would go forward with a few suitors that I felt Were the best matches for me. One of the things that was super important to me was to find investors that were value aligned, but also I'm a single founder. So for me, my board and my investors are a little bit more important than I think if you have a co-founder. So it was really important I actually went out for the round. I only went out to six VCs, and I'd already had relationships. I already knew that I wanted to work with them, and I ran a true process, but in such a short period of time. First, instead of that six weeks that the othe…

AI assessment note: “do a lot of quote-unquote dating before I set out to raise”

Q No, absolutely. I very much live by the same philosophy. I'm intrigued. You said about the extremes there. Going from very capital efficient to the recent light speed round, and now raising over forty three million dollars in funding. I'm intrigued. What was the cap Capitalist that really made you think now's the time to raise that big round?

A Yeah, so it was actually all very deliberately orchestrated, where Series C and Series A, I wanted to be really capital efficient. We had a lot of things to prove, and I wanted to make sure that when it came time for the Series B, that we're going to be able to raise the amount of money that I knew we needed to really do all the things that I envisioned when starting the business, and in order to You can't just raise forty three million dollars because you want to. So, you know, by being really lean in the beginning and being really disciplined, uh, we were able to do it. So it was all part of the plan from the beginning. And, you know, I just feel like really lucky that we were, we were actually able to see things play out as we had originally dreamed.

AI assessment note: “So it was all part of the plan from the beginning.”

Q Can I ask, how did having children change how you think about the world and running a business?

A I mean, it changed so much of it, but one of the things that it changed is definitely my view on reality. I think before I had kids, there was this idea that you can have it all at some point, and I realized that that is just It's not possible, you know, and, and I think that it's an idealized vision that a lot of people have, like, oh, you know, I'll be able to do everything, and it'll be wonderful, but I think that it's causing this tension where people are become really hard on themselves, and I think it's okay to say, you can't have it all, and you have to make choices. There are trade-offs, but the trade-offs are worth it, and, and, you know, your kids will be fine without you helicoptering around them.

AI assessment note: “one of the things that it changed is definitely my view on reality.”

Q Kat, being practical, what did you prioritize given the capital light structure, and then what did you sacrifice?

A Yeah, so I would say we've prioritized, I mean, everything that we've done has been ordered, and I'd say, you know, executed in that order. So, things like team growth to be able to, to build our own proprietary site, you know, that's something that we didn't prioritize. We knew we could use Kind of an out-of-the-box solution, which was very not out-of-the-box by the time we were done with it, but an out-of-the-box solution to start and, you know, then got to a point where, where we were, we were breaking it, you know, and then built our own site. And one of the downsides to that was there were a few features that we really wanted our customers to have that we couldn't ship to them for some time.

AI assessment note: “there were a few features that we really wanted our customers to have that we couldn't ship”

Q Why was that? That can't be a coincidence that just in those six weeks it doubled.

A Well, I mean, I picked a good six weeks to raise money. Yeah. You know, you, you kind of have, once you've got some data under belt, you kind of can understand the seasonality of a business. So I, it wasn't a total accident, but I didn't expect it to be quite at that magnitude. So, you know, what had happened is I originally was going out for a bit more cash on the series a, and when our run rate had doubled, I kind of took a step back and I was like, oh my gosh, I had promised all of these VCs, but you I was looking for a certain valuation or not promise, but we had kind of been discussing a certain valuation. I was getting term sheets. You know, I was in such a great position, but it didn't feel good anymore because our run rate had doubled and the valuation felt like a little silly to me. So I actually decided to blow up the entire round and basically wrote my own term sheet and sent it back to everybody. And I said, Hey guys, little untraditional here, but this is how it's going to be. And I sent back the term sheet and I said, do you want to participate or not? And I got three wonderful VCs to participate.

AI assessment note: “once you've got some data under belt, you kind of can understand the seasonality”

Q Why was that? That can't be a coincidence that just in those six weeks it doubled.

A Well, I mean, I picked a good six weeks to raise money. Yeah. You know, you, you kind of have, once you've got some data under belt, you kind of can understand the seasonality of a business. So I, it wasn't a total accident, but I didn't expect it to be quite at that magnitude. So, you know, what had happened is I originally was going out for a bit more cash on the series a, and when our run rate had doubled, I kind of took a step back and I was like, oh my gosh, I had promised all of these VCs, but you I was looking for a certain valuation or not promise, but we had kind of been discussing a certain valuation. I was getting term sheets. You know, I was in such a great position, but it didn't feel good anymore because our run rate had doubled and the valuation felt like a little silly to me. So I actually decided to blow up the entire round and basically wrote my own term sheet and sent it back to everybody. And I said, Hey guys, little untraditional here, but this is how it's going to be. And I sent back the term sheet and I said, do you want to participate or not? And I got three wonderful VCs to participate.

AI assessment note: “once you've got some data under belt, you kind of can understand the seasonality”

Q So much so, that was such a good segue into my next question, which is actually from Alex. He speaks about your obviously location in New York. I'm intrigued. You've been now operating in New York and seeing kind of the development of the ecosystem. How have you seen the New York ecosystem change, maybe since you've really been so entrenched in it?

A Yeah, so New York definitely seems to be the home of consumer entrepreneurship. As I continue to meet people, and as I continue to kind of be out there in the startup community, there are definitely a huge number of consumer startups budding and growing in New York City, and the thing that I think is just so wonderful about the community is everybody's really helpful. There's a lot of camaraderie. I don't know what it's like on the West Coast. I've never built a business on the West Coast, but from what I hear is it's not quite so collegial. And it's really nice to have that community where people are willing and excited to share best practices and, you know, really help each other out.

AI assessment note: “New York definitely seems to be the home of consumer entrepreneurship.”

Q So much so, that was such a good segue into my next question, which is actually from Alex. He speaks about your obviously location in New York. I'm intrigued. You've been now operating in New York and seeing kind of the development of the ecosystem. How have you seen the New York ecosystem change, maybe since you've really been so entrenched in it?

A Yeah, so New York definitely seems to be the home of consumer entrepreneurship. As I continue to meet people, and as I continue to kind of be out there in the startup community, there are definitely a huge number of consumer startups budding and growing in New York City, and the thing that I think is just so wonderful about the community is everybody's really helpful. There's a lot of camaraderie. I don't know what it's like on the West Coast. I've never built a business on the West Coast, but from what I hear is it's not quite so collegial. And it's really nice to have that community where people are willing and excited to share best practices and, you know, really help each other out.

AI assessment note: “New York definitely seems to be the home of consumer entrepreneurship.”