The Exchanges

Q you, but if that's the fundraise dating game, and that's kind of one side of the equation, the other side of the table is the investors themselves, and when we chatted before, you said the best investors are operators. Again, how can I not dive straight on these tidbits? So why do you think this, and what do you think these operator investors have that maybe alternative career VCs don't?

A I think first and foremost, you know, an investor that was an operator, which I have to say is really hard to find, but an investor that was an operator, I'd say first and foremost, really understands how hard it is to be a founder, how hard it is to be an operating team, and so there's a sensitivity or an empathy there. The second is that they really appreciate that there's a million things that you want to be doing at any period of time, and you desperately have to prioritize, and so, you know, what you can sometimes see with investors is that They throw a million ideas at you and they can't figure out why you can't move fast enough and why you can't do all of them at the same time. And an investor who's a former operator really understands the nuance of having to pick and choose and prioritize. I think that with an investor, you know, the beauty of an institutional investor who has never been an operator is that for good or for bad, they have pattern recognition, right? And so they've seen Similar patterns across a multitude of businesses, and I think that that can be an advantage in that there is recognition of those patterns that can be attributable to different businesses. At the same time, there can be the negative instinct of pattern recognition where they sort of lump you in with every other business that may or may not be applicable to yours, and it's, well, you know,…

AI assessment note: “tactical advice that you get with a former operator.”

Q No, I completely agree with you. I mean, one element in terms of kind of ensuring you have as much runway as possible is as our friend, uh, Rachel at Daily Harvest mastered in the early days being capital efficiency. I'm intrigued. How do you think about capital efficiency today with Rockets of Awesome and really implementing it into your operations moving forward?

A Yeah, you know, I think that as you scale, it becomes harder. As you become a later stage of business, it becomes harder. I think in the beginning when You have smaller teams, smaller growth expectations. It's much easier to grow with baby steps and to grow in a more efficient manner. Generally overhead tends to be one of the larger drivers of capital in a business. And as you start to build your team, that is a lever that isn't as flexible and isn't as responsive to how you are growing as a business, right? And so often you You know, you're never trying to, you never want to be hiring too far ahead, but you never also want to get into a position where you're unable to grow because you don't have the people in place, and so I think it's a constant balance. For us, we're always looking at what are the levers that we can pull that will give us flexibility in pulling back on spend if we don't see the growth that we're anticipating, and whether that is On future hires, whether that is on extraneous kind of spend, whether it's game outings or even snacks within the building, sometimes those things can give you a little more flexibility, but typically it really is an overhead that gives you the most, and that is harder to be flexible on. So another way to think about it is, do you actually bring in contractors or part-time talent In periods where you know that you're going to need to…

AI assessment note: “what are the levers that we can pull that will give us flexibility”

Q What moment in your life served as maybe an inflection point and changed the way you think?

A Probably pivoting the business from Cricket Circle to Rockets of Awesome was a tremendous inflection point for me, and probably one of the first moments where I could really recognize what people meant when they said that you will make decisions that are for Other people other than yourself. And what I mean by that is that in that moment where we decided to shift focus from content around babies and baby gear to a much broader category of kids and apparel, that was a moment where it was all about the other constituents that I was responsible for being my employees and my investors. It wasn't about me. Of course, it had to be something that I believed in, that I was passionate about, that I believe that I had a unique point of view on, that I could create something really special in the universe, but it was a moment where I still very, very, and to this day, believe in the vision that we were building at Cricket Circle, but I knew that there was a bigger and greater opportunity in what we could build for Rockets of Awesome, and it was definitely a development opportunity for me, and realizing that I had the maturity to be able to Make decisions that were best for other people besides myself.

AI assessment note: “pivoting the business from Cricket Circle to Rockets of Awesome was a tremendous inflection point”

Q No, I completely agree with you. I mean, one element in terms of kind of ensuring you have as much runway as possible is as our friend, uh, Rachel at Daily Harvest mastered in the early days being capital efficiency. I'm intrigued. How do you think about capital efficiency today with Rockets of Awesome and really implementing it into your operations moving forward?

A Yeah, you know, I think that as you scale, it becomes harder. As you become a later stage of business, it becomes harder. I think in the beginning when You have smaller teams, smaller growth expectations. It's much easier to grow with baby steps and to grow in a more efficient manner. Generally overhead tends to be one of the larger drivers of capital in a business. And as you start to build your team, that is a lever that isn't as flexible and isn't as responsive to how you are growing as a business, right? And so often you You know, you're never trying to, you never want to be hiring too far ahead, but you never also want to get into a position where you're unable to grow because you don't have the people in place, and so I think it's a constant balance. For us, we're always looking at what are the levers that we can pull that will give us flexibility in pulling back on spend if we don't see the growth that we're anticipating, and whether that is On future hires, whether that is on extraneous kind of spend, whether it's game outings or even snacks within the building, sometimes those things can give you a little more flexibility, but typically it really is an overhead that gives you the most, and that is harder to be flexible on. So another way to think about it is, do you actually bring in contractors or part-time talent In periods where you know that you're going to need to…

AI assessment note: “For us, we're always looking at what are the levers that we can pull”

Q you, but if that's the fundraise dating game, and that's kind of one side of the equation, the other side of the table is the investors themselves, and when we chatted before, you said the best investors are operators. Again, how can I not dive straight on these tidbits? So why do you think this, and what do you think these operator investors have that maybe alternative career VCs don't?

A I think first and foremost, you know, an investor that was an operator, which I have to say is really hard to find, but an investor that was an operator, I'd say first and foremost, really understands how hard it is to be a founder, how hard it is to be an operating team, and so there's a sensitivity or an empathy there. The second is that they really appreciate that there's a million things that you want to be doing at any period of time, and you desperately have to prioritize, and so, you know, what you can sometimes see with investors is that They throw a million ideas at you and they can't figure out why you can't move fast enough and why you can't do all of them at the same time. And an investor who's a former operator really understands the nuance of having to pick and choose and prioritize. I think that with an investor, you know, the beauty of an institutional investor who has never been an operator is that for good or for bad, they have pattern recognition, right? And so they've seen Similar patterns across a multitude of businesses, and I think that that can be an advantage in that there is recognition of those patterns that can be attributable to different businesses. At the same time, there can be the negative instinct of pattern recognition where they sort of lump you in with every other business that may or may not be applicable to yours, and it's, well, you know,…

AI assessment note: “an investor that was an operator... really understands how hard it is to be a founder”

Q Can I ask, in terms of, kind of, solutions to this, kind of, fundamental ecosystem problems, Do you feel that the increasing number of female GPs that we've seen recently is really strong progress? Or is there other elements that you'd really like to see change that you think would really move the needle?

A I think it's just more. I think it's more of everything. I think it's more female investors. I think it's more female entrepreneurs. You know, what I realize is that there are categories that will never be innovative if we don't have female entrepreneurs and female investors, right? Right. So, you know, take Lola, a tampon company, for instance. I can't imagine that a man was ever going to innovate the tampon, right? Because they don't, for the life of them, understand how it works or what it does or the nuances of how you can make it better. And on the flip side, if you didn't have female entrepreneurs who, again, really intimately understood and actually cared about The tampon, then you would never have innovation in a category that probably hasn't been innovated in 50 to a hundred years. So I think it's incumbent upon both the investors and the entrepreneurial community to raise women in both respects so that we can innovate all these categories that deserve to be innovated.

AI assessment note: “I think it's just more. I think it's more of everything.”

Q Talk to me. In some respects, I might be considered a non-operator VC, so give, give me some advice. I'd love to hear. How can I improve that experience, touchpoint, empathy relationship? What would your advice be? Other than become an operator.

A I think more than anything, and you know, I also have empathy for investors in that they have a lot of demands, right? And so not only, you're not the only portfolio company that they have to worry about, combined with the fact that in many ways, investors have to be doing what founders do, which is fundraise, right? And so in many ways, they have a sensitivity around the fundraise process, but investors have a You know, well, often I find that they're not as connected or not as immersed into my business as I would like for them to actually be able to add value. I also have an appreciation of why they can't always be, but I would say that the investors that take the time to really understand the business that they're invested in, to really understand the nuances of that business, the drivers of the business, and not just On paper, but really the customer and how that customer and the psychograph of the customer impacts those levers. That's when you get an investor that can really add value. So I would say my greatest bit of advice or my greatest request would be that investors really take the time to not just say, how can I be helpful? Or I really want to be helpful, but To be helpful, it means that you actually have to spend time with the business, spend time with the operators, spend time with the founders to really understand the nuances of the business. It's not that you're…

AI assessment note: “my greatest bit of advice or my greatest request would be that investors really take”

Q Talk to me. In some respects, I might be considered a non-operator VC, so give, give me some advice. I'd love to hear. How can I improve that experience, touchpoint, empathy relationship? What would your advice be? Other than become an operator.

A I think more than anything, and you know, I also have empathy for investors in that they have a lot of demands, right? And so not only, you're not the only portfolio company that they have to worry about, combined with the fact that in many ways, investors have to be doing what founders do, which is fundraise, right? And so in many ways, they have a sensitivity around the fundraise process, but investors have a You know, well, often I find that they're not as connected or not as immersed into my business as I would like for them to actually be able to add value. I also have an appreciation of why they can't always be, but I would say that the investors that take the time to really understand the business that they're invested in, to really understand the nuances of that business, the drivers of the business, and not just On paper, but really the customer and how that customer and the psychograph of the customer impacts those levers. That's when you get an investor that can really add value. So I would say my greatest bit of advice or my greatest request would be that investors really take the time to not just say, how can I be helpful? Or I really want to be helpful, but To be helpful, it means that you actually have to spend time with the business, spend time with the operators, spend time with the founders to really understand the nuances of the business. It's not that you're…

AI assessment note: “investors really take the time to not just say, how can I be helpful”

Q I do want to kind of dive into one final topic before the quickfire, being the element of being a female in a dominated male industry. You said before, it's every stereotype you can imagine. Very sad to hear, but gaining some context, can you tell me of maybe a story where this has really materialized for you, and how did you respond?

A You know, before I get into that personally, I think that it is, there's statistically significant data in research that will tell you that when male founders are meeting with investors, whether they're male or female investors, they are asked the question of what is the greatest opportunity that you have ahead of you? And women entrepreneurs are asked, what is the greatest risk? So I think even that probably sets the stage for there really still being a difference between being a male and female entrepreneur. For me, you know, I've probably had, you know, like I mentioned, I've experienced every stereotype you can imagine. I would say probably the most telling to me has been being a female entrepreneur that's also a mom and a female entrepreneur that's a mom with a husband in the space that has had six Success. And that to every investor says, why is she here? And like, what is her goal? She doesn't really need to be here. That is sort of their natural instinct. And then their instinct as well, like it must be a hobby or sort of like a side project. Right. And so the questions that I've received, I've fundraised, I've always been a single founder. And so I fundraised as a female single founder, I fundraised pregnant and I fundraised as a mom and I've received various Questions along the lines of, so how much time do you spend on that? Or, um, so how do you balance it? You know…

AI assessment note: “I really turn it back on them... and so I'll say, well, what do you mean?”

Q My word, I think that's what they call conviction. I do have to ask that you're an incredibly confident and accomplished lady. How would you advise someone who maybe is younger, doesn't have the confidence, doesn't have the business expertise maybe that you have with two prior businesses, a first-time female founder who doesn't maybe have the confidence for the slightly more FU mentality? What would that advice be?

A Well, you know, my motto is fake it till you make it. That is because no matter, you Any executive, any entrepreneur, anyone that you speak to who has had success that you look up to that you say, God, like they are the epitome of success. The reality is that we all have imposter syndrome, right? We all think that we're not good enough or we're not there yet, but the ones that succeed are the ones that fake it. We just fake it every single day and we put on the air of confidence, whether we're Confident you're not. People believe that air of confidence, and I think that the ability to fake it, and the ability to have a conviction, and be focused, and to, you know, if it's faking confidence, if it's real confidence, the ability to do that enables us to do things that we never could have imagined were possible.

AI assessment note: “my motto is fake it till you make it.”

Q I do want to kind of dive into one final topic before the quickfire, being the element of being a female in a dominated male industry. You said before, it's every stereotype you can imagine. Very sad to hear, but gaining some context, can you tell me of maybe a story where this has really materialized for you, and how did you respond?

A You know, before I get into that personally, I think that it is, there's statistically significant data in research that will tell you that when male founders are meeting with investors, whether they're male or female investors, they are asked the question of what is the greatest opportunity that you have ahead of you? And women entrepreneurs are asked, what is the greatest risk? So I think even that probably sets the stage for there really still being a difference between being a male and female entrepreneur. For me, you know, I've probably had, you know, like I mentioned, I've experienced every stereotype you can imagine. I would say probably the most telling to me has been being a female entrepreneur that's also a mom and a female entrepreneur that's a mom with a husband in the space that has had six Success. And that to every investor says, why is she here? And like, what is her goal? She doesn't really need to be here. That is sort of their natural instinct. And then their instinct as well, like it must be a hobby or sort of like a side project. Right. And so the questions that I've received, I've fundraised, I've always been a single founder. And so I fundraised as a female single founder, I fundraised pregnant and I fundraised as a mom and I've received various Questions along the lines of, so how much time do you spend on that? Or, um, so how do you balance it? You know…

AI assessment note: “I really turn it back on them because I so want them to hear themselves”

Q really screwed, so don't worry. I've done worse. But I would love to touch on the element of leverage. You know, often leverage is gained through not having such shortened runway. I'm intrigued. How do you think about the right amount of runway to raise Is it the hallowed 18 months? And is that, do you think, a crucial way to be one up in the game, so to speak?

A You know, I think that everybody, myself included, likes to give advice to entrepreneurs, which is, you know, raise money when you don't need it. That's all well and good, and it's great in theory, but I would say it's pretty rare in execution, particularly in the What you have is you essentially are setting thresholds for which you believe in support of either investors that you have or advisors that you have that really understand market dynamics and investor mentality. You're setting thresholds for which you have to hit certain goals to then really deserve or have proven out a thesis to raise the next round of funding, and in theory, you're going to do that with tons of runway in front of you, but It can take longer than expected to sort of hit those thresholds, and I think that, you know, whether you're an experienced founder or a first-time founder, you don't always know how long it's going to take you. You can have a thesis on it, but you're not always going to know, and so people tend to say that an 18 months of runway is the comfortable amount of time to give yourself to unlock or prove out the next Stage of your thesis, but inevitably things happen throughout the business that might shift your course might shift, you know, how impactful you think a tactic is going to be. So there's a lot of unknowns along the way. And I think the best that you can do is always have a p…

AI assessment note: “people tend to say that an 18 months of runway is the comfortable amount”

Q really screwed, so don't worry. I've done worse. But I would love to touch on the element of leverage. You know, often leverage is gained through not having such shortened runway. I'm intrigued. How do you think about the right amount of runway to raise Is it the hallowed 18 months? And is that, do you think, a crucial way to be one up in the game, so to speak?

A You know, I think that everybody, myself included, likes to give advice to entrepreneurs, which is, you know, raise money when you don't need it. That's all well and good, and it's great in theory, but I would say it's pretty rare in execution, particularly in the What you have is you essentially are setting thresholds for which you believe in support of either investors that you have or advisors that you have that really understand market dynamics and investor mentality. You're setting thresholds for which you have to hit certain goals to then really deserve or have proven out a thesis to raise the next round of funding, and in theory, you're going to do that with tons of runway in front of you, but It can take longer than expected to sort of hit those thresholds, and I think that, you know, whether you're an experienced founder or a first-time founder, you don't always know how long it's going to take you. You can have a thesis on it, but you're not always going to know, and so people tend to say that an 18 months of runway is the comfortable amount of time to give yourself to unlock or prove out the next Stage of your thesis, but inevitably things happen throughout the business that might shift your course might shift, you know, how impactful you think a tactic is going to be. So there's a lot of unknowns along the way. And I think the best that you can do is always have a p…

AI assessment note: “people tend to say that an 18 months of runway is the comfortable amount”