Lucy Deland – Co-Founder & COO of Paperless Pos‪t‬ and Partner at Inspired Capital

Episode 131

What do you do after co-founding one of the hottest internet companies around? Some become VCs and start their own firm with other powerful entrepreneurs and notable people! Meet Lucy Deland, former COO and Co-founder of Paperless Post. Now as a VC of the super hot Inspired Capital, she is helping lift other entrepreneurs by investing and helping them launch their early-stage companies. This was a great episode. I can’t wait for you to listen.

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Kara Goldin  00:00

Hi, everyone, its Kara Goldin from the Kara Goldin show. And I’m so excited to have my next guest. Here we have Lucy Deland, who is one of the founding partners at inspired capital, but also one of the founding team members at the paperless post, which is this awesome, awesome, awesome company that I have known about and used for many, many, many years. And she was at the last decade was their chief operating officer. And I’m sure had tons and tons of learnings you guys were disrupting and so many amazing ways. And she built-in led the finance, customer insights and operations, strategic planning and marketing, and driving the company’s growth to a network of 100 million. Amazing on a lot of friends.

Lucy Deland  00:52

Thank you so much for having me.

Kara Goldin  00:54

Yeah, super, super excited. And then I also am really excited to hear because I think it’s something that so many people sort of think about in their next career move is, you know, what do you do next after you’ve done lots of great founding and, and had really great roles as you did? So I’m super excited to talk about inspiring capital, as well. And yeah, so let’s get started. But Welcome, welcome.

Lucy Deland  01:23

Thank you so much. Again, I’m very excited to be here.

Kara Goldin  01:25

What was sort of the backstory? I mean, you you graduated from Harvard, you like, tell me a little bit about your journey?

Lucy Deland  01:34

Yeah, absolutely. So I actually went right into VC and the investment side from undergrad and really thought that I was bypassing a step, you know, going through the finance, I, you know, investment banking step, and I just got lucky and was bolted right into venture capital. I always loved technology, innovation, the excitement of growth. And so I was thrown into the deep end there and actually found when I was there, that what I really coveted and who I wanted to be, when I grew up, were the management teams that were sitting across the table from me, and that their jobs seemed so exciting, and, you know, willing these companies into existence, growing them to employ hundreds of employees building, you know, products that hadn’t existed before. That seemed like a really cool job to have. And equal and opposite. I felt like even if I was going to sit back in the investor seat, that that experience would be invaluable that if I was going to advise companies work with entrepreneurs, that have been in their seat before was, at least for me, going to be a really crucial step for building up the skill set, I wanted to have to be able to be back on that side of the table. But that was really not what I was thinking about. At that time, I was really thinking, How do I get into that founder seat. So over a couple of years of evaluating hundreds of businesses, started speaking to a couple of friends about the concept, they were throwing around hope, which was sort of the transformation and digitalization of the stationery world and bringing on this the sort of what we saw as the last, the last communication that had not yet found its way into a digital format. And so in the fall of 2008, took the leap, and we started raising our seed round, as the world absolutely crumbled around. It’s

Kara Goldin  03:26

gonna say such a great time, right? We,

Lucy Deland  03:30

we incorporated the company on the day that Lehman collapsed, which was definitely not on purpose

Kara Goldin  03:35

in New York site to in New York City,

Lucy Deland  03:37

just, you know, 40 blocks out of where we were,

Kara Goldin  03:40

Oh, my gosh, crazy. Crazy. And so what were you like, what did you think that day? Do you remember? Where you just oh, my gosh, what did I just do?

Lucy Deland  03:50

Well, actually, as I was considering jumping into this world, and you know, in New York, 2008, finance was had been flying high. Up until that point, entrepreneurship really had not taken hold in this city quite yet. And so everyone sort of thought I was a little bit insane for leaving this cushy, exciting job for this sort of unknown path. And you know, you tell someone who works at paperless post in 2008. Everyone gives you a blank stare.

Kara Goldin  04:20

I call them the doubters. Right? They’re all thinking you’re a little crazy. You’re all Yeah, yeah, you’d be fun to get a glass of wine with still but they think you’re sort of That’s right. Yeah, maybe

Lucy Deland  04:30

we’re even more fun to get a glass of wine with because you have that nuts. Yeah. And then as really, as this landscape started to shift so dramatically underneath all of our feet in New York, it it was kind of reassuring. I was like okay, so nobody has the higher ground. We’re all here trying to make it work. Yeah. My friends from Lehman who are getting laid off I’ve got friends and other banks that are freaked out and I was like, well jump into this scary world with me then. This is the moment in time like when it would be a better time to take a huge risk when the safe places are disappearing.

Kara Goldin  05:03

Yeah, there really are no safe places. So yeah, yeah, my father actually was I call him a frustrated entrepreneur within a large company growing up. And I watched him just really think about, gosh, if I left, you know, back in his day, it was like You had one job or labor to write you imagine the stress of picking your like, only job at age 21. I talked to my kids about this all the time. Like you think you got stress, like images, you know, whatever, 16 years ago when you were trying to make a decision? And I mean, that’s a lot, right. I mean, that was just, it’s messy. But then he was actually laid off after he had developed a product, which is still alive today called healthy choice. And he was laid off by his company, he had been through an acquisition, initially, healthy choices in a company called armour food company, and they were acquired by conagra. And he was laid off for not having an MBA. It was all the Yeah, for not checking in never in a million years that I mean, that did he think that and again, he really believed that there was job security. Anyway, I just I bring that up. Because I think it’s, it’s something that more and more people are seeing that it’s you got to go do what you love and go jump into something that you’re really learning and all of them saying waiting for it.

Lucy Deland  06:34

Yeah, right? Because safety is can be an illusion.

Kara Goldin  06:37

It’s a total illusion. So how did you come up with the idea,

Lucy Deland  06:41

so, my co-founder, James Hirschfeld came up with it on his 21st birthday, as he was throwing sort of the first formal, you know, I’m inviting people to a party that he never had, and kind of got to the end of the process and found that there was no way that really made sense he thought for, you know, was probably back in 2000, early 2008, late 2007. That made sense for today. And he is someone who has high design, heat, but he was also a 21-year-old man who was not going to go invest in the paper he didn’t know his friend’s addresses. And so it really started as a very micro use case. And he looked out and said, I think that if I was a, you know, guy trying to invite 100 college kids to a party feel this need, then I believe that there is a whole host of people who is organizing much more important events who have embraced the internet, that would be really happy to still have. And what we always sort of prioritize was the design and self-expression, something that really represented them well, but allowed them to get instant responses to have a real carbon neutral footprint. You know, maybe we’ve come to the day and age where we shouldn’t fly pieces of paper around in order to invite people to events, and believe that we could get there without sacrificing the look and feel. And today that makes a ton of sense back in 2008. Designing live in the browser was not yet a concept that existed paperless was really on the forefront of the concept of being able to design something and watch it come to life as you were doing. So Adobe, everything else was a desktop environment where you had to download an application or you know, put it in a CD ROM. And those were so hard to use, you had to be a designer. And what we really wanted to bring to life was the idea that you had something in your mind, we could give you enough tools and enough guidance and templates that you could create something you were proud of. And do so within Internet Explorer nine or whatever we were dealing with back then, which was still pretty primitive browser technology as well.

Kara Goldin  08:53

Yeah, super primitive. So how did he find you?

Lucy Deland  08:56

So he decided to start the company with his sister, Alexa Hirschfeld, who was a great friend of mine at Harvard. And so when they were batting around ideas on I was working inventor, we would just meet on the weekends, nights weekends and brainstorm and come up with ideas and like all of the best partnerships in life, it really came about organically that I ended up joining the team because we knew that the match was there that the chemistry was there. And I’m I would you know, people come and ask me for advice on joining co-founding teams where there is a married couple or siblings or cousins and I was like, I can’t give you advice. You’ve got to you have to go find your own chemistry. It’s not about whether or not they’re siblings or whether or not they’re married. It’s got to be the right people. And I was so fortunate to find that and then I think actually because they were siblings. You know, the honesty, the raw honesty that you get in a sibling relationship sort of was extended to me and I was brought into the fold Meaning that we could have incredibly difficult conversations, heated debates, you know, without throwing around a lot of ultimatums and then be like, Okay, so we’re gonna get pizza or Indian food?

Kara Goldin  10:13

Well, I work, I work with my husband or my husband’s Chief Operating Officer. And so we’ve had, you know, yeah, we started him 15 years ago, and something I talk about on a lot of the podcasts that I do is, that was the thing that we heard from so many potential investors early on was that we were a married couple. And, you know, they didn’t really invest in married couples, I now sort of having an opinion that that’s not necessarily why they didn’t invest.

Lucy Deland  10:44

Right, that it was a nice, easy thing for them. It wasn’t

Kara Goldin  10:47

an easy out, right? Like, it’s just this and I tell this to entrepreneurs all the time, that if they’re, you know, oftentimes people just, they just don’t want the conflict, right? They don’t want they want something that they know that you’ll believe, but it’s not necessarily exactly what they’re on. Right? The root of the thing and I remember my husband saying to me, you know, we were both we have both come from Tech, we had never had raised money before, but he’s a Silicon Valley attorney, he had been in plenty of rooms with people. And anyway, it was fascinating. And we ended up raising money in lots of different other ways. And being very successful. Yeah, I mean, it’s been, there’s always ways to do it. But I think it’s, it’s a, it’s just another wall. And I often talk about, you know, the doubts, as I mentioned earlier, you’re always gonna, if you believe something, you’ll attract people who will also say things, you know, that will make you doubted even more, but you have to figure out how to break through those things to get around it. So I love hearing, I love hearing that because I think it’s so true that the conversations that go on around our company are very honest, and we don’t hedge and some


of the points and yes,

Kara Goldin  12:00

we seem like brother and sister, we’re like, you know, we’re not screaming at each other. But we’re saying no, you’re wrong. You know, sorry, there’s

Lucy Deland  12:08

a psychological safety to be wrong. Yeah. And that’s okay, where you’re coming from, but

Kara Goldin  12:13

yeah, sorry, we’re, you’re still wrong, you know, yeah, we, we still go on with it. And we laugh and, and everything. And but I think to your point, you guys all had different skill sets. And I think that that’s the most important thing is being able to really have different skill sets, and, and really exciting. So you also attended that little school and Massachusetts, at the same time, I guess that Mark Zuckerberg was there. So did you ever run into were you part of the social network, or he

Lucy Deland  12:46

he was my class, though he left pretty quickly after this little thing called Facebook took off. But it was incredible to watch it from, you know, user zero, really take off like wildfire on our campus, and understand the implications. I remember I was walking to class walking through the dorms with my roommate at the time. And she and I had just become roommates a few weeks earlier, because it was October, and everyone was wishing her a happy birthday. And we were sophomores. Or we were juniors. And I just turned to her. And I was like, I mean, I know it’s your birthday. But literally, how does everyone know? It’s your birthday. And she was like on Facebook, either, you know, everyone woke up that morning, and there was not that much else on there. So they told you it was someone’s birthday. And they kind of told you who was on. And that was it. And it was just sort of a set of profiles of people. And that was sort of the only alert that you would get. And I was like, wow, that’s, that’s such a different experience to have a birthday now than last year. And I mean, that’s sort of the understatement of the impact of Facebook of the decade. But I think what happened in our class and the classes around us were that there was this halo effect of watching him and a couple of other classmates go and start this. And my co-founder from paperless has a joke that the rest of us were, you know, still figuring out the best class schedule configuration, and he was on to his second 100 million. And all of us kind of looked up and we’re like, oh, we should do that.

Kara Goldin  14:22

Oh, and sometimes it just takes us all like longer, right? Figure it out. I mean, but that’s Yeah, it’s such a crazy example. But it’s, it’s pretty, pretty funny that you guys were there at the same time and that you saw it taking off. I’ve really wondered actually if people really got it. Like I’ve met other people before, who have been around people who were founders of companies and they didn’t really know what was happening. Right? They didn’t know that the

Lucy Deland  14:52

service was happening or the product was actually happening and it sounds like you did, it was definitely became a conversation piece. And it was, you know, this was even among small numbers, but it was just a transformation of how you could follow and interact and communicate with people in the early days. And it was just clear that was better than Friendster. And you couldn’t quite put your finger on why, but it had that it instantly was as a guest on the campus.

Kara Goldin  15:21

That’s wild. I was at America Online until 2001. And I mean, I was there when an instant messenger was there. And it was the same kind of thing. It was, no matter what else was going on. I was running eCommerce and shopping partnerships, and no matter what was going on, I mean, I knew that instant message was just going to be a huge thing. I mean, ultimately ended up being texting, right. I

Lucy Deland  15:45

mean, that’s, that’s a sense that there are so many products today that are just aspiring to get back to an I am.

Kara Goldin  15:55

Totally, yeah, and it’s so interesting. But I remember when you feel the wave, you know, coming in, but it’s just it’s hard to describe, but you’re, you’re like, Oh, yeah, that’s really cool. And then you watch it and, and see that hockey stick. It’s pretty exciting. So it’s really cool, though, that you were there. That’s, that’s super, super cool. So you left a paperless post and you decided to go back to investing. And so what was kind of your thinking there.

Lucy Deland  16:23

As I was transitioning from paperless, I knew that I had this itch to build my next sort of venture. And I couldn’t have told you then what that meant. Because when I was an operator, I was very heads down. I wasn’t sorting of keeping lots of different pots boiling, I really, I was heading down at work. And I might have been advising a few CEOs and founders outside but kept it pretty lean. And so it was like, I’m gonna take six months off and really figure out where I want my next decade to take me I’ve had such a, an amazing decade, how do I stop it, that was a little bit of a daunting feat to think about that. And then also, you know, what do I really want out of it. And I had the great fortune of sort of timing, that exploration with my great friend, and now business partner, Alexa von tobel, who was leaving Northwestern Mutual. And she and I had been one another’s sort of closest external colleague, closest confidant on this founder journey over the past decade, you know, the person that you call late at night when you really need to work through a problem, and you need some external perspective on what you’re dealing with. And we provided that for each other through the learn best and paperless journeys. And so I think I ended up in her office talking about this venture firm that she was thinking about bringing into reality. weeks after my last day at paperless, and, like all the best partnerships, it really started to snowball and become an organic conversation about how I would build it, what I would do, how would I prioritize, and sort of built the foundation of becoming a partner and inspired really organically?

Kara Goldin  18:05

I love it. She was a CEO, right? She wasn’t an operation. Yeah, so different skills,

Lucy Deland  18:11

different skills, different perspectives. I love it. Yeah, I

Kara Goldin  18:14

love it. And what in how big is your fund?

Lucy Deland  18:16

So we have $200 million early-stage funds. So we focus on seed and Series A, and we have been around for about two years now. I think we just had our second birthday two weeks ago, and which seems impossible. But here we are. And we invest about one to 3 million in the seed companies and about five to 10 million into series A,

Kara Goldin  18:39

that’s awesome. I feel like so often when I’ve talked to different venture capitalists, they actually haven’t had the operations experience that you’ve had, do you feel that that is super useful? I mean, I would imagine that especially with your portfolio and trying to figure out how people are building.

Lucy Deland  19:00

To me, it is it’s an incredibly important experience that I go back to all the time and thinking about this and is a really important influencing factor on why we chose the stage of investment that we did. And not only do we think that it’s the most interesting place to put our dollars, but we feel that our experience willing companies into existence, sort of transforming a category really is well suited to help entrepreneurs who are really early in their journey, really establishing product-market fit, and figuring out how both they’re going to scale the company, how they’re going to build the model that scales but also how they’re going to scale themselves. And move from being in a building and doing mode which you have to be in the early days into a leading and managing and vision setting mode exclusively. And, and I think that there are great investors who sit at all parts of the capital stack, many that bring in different vantage points than I have, I would say there are probably lots of people who are going to lead your series. See that has really Important vantage points about growth capital and IPO markets that I’m not going to bring to the table and vice versa, I have really important experience on how you truly build an organization to build the company that you want to create. And I think that can go across any company building experience, it doesn’t have to be sector-focused.

Kara Goldin  20:22

What would you tell one of your portfolio companies or somebody who’s just going out and raising money for the first time knowing you’ve been on both sides of the table? What do you think are the things that are really important?

Lucy Deland  20:36

I think of you as the operator, you, as the founder has to fall in love with the idea or the problem that you’re trying to solve. And that is crucial. And you have to remember that the investor is actually Betting on you. I think, rightfully so founders get really, really invested in their ideas and the products that they want to build and the problems that they’re going to solve. And they need to sell that to the investor. But they have to remember that at the end of the day, they’re the best. And that the greatest idea is only like its limitation is going to be the person that is setting out on this journey. And so I think founders really need to focus on how am I going to tell my story so that this investor understands why I’m the person to bet on to go solve this problem, and that they really understand me my strengths, my weaknesses, everyone, you know, nobody has intense strengths without weaknesses. So it is not about masking, you know, who you are, it is about actually amplifying it. So the investor really understands why you’re going to achieve superhuman feats, which is often what is required, particularly in the early days, to get a venture off the ground to hire people that are more talented than you deserve to be able to hire, to get your first customers to take a chance on you to bring a product truly to life to the quality that you have, from your head, actually into the real world, all of those things usually take more than just doing hard work. They take you to know that extra and you need to really demonstrate to the investor base, that you’re going to bring that extra.

Kara Goldin  22:14

And how do you pick the investor? I mean, how do you ultimately I guess, if you have a choice, which I think you always have a choice, but how is it a

Lucy Deland  22:24

all at least keep it in your mind that you write a choice, right. The other thing I would say is when you are raising money, know that this is your process to run, we as investors are participating in your process. So you don’t need to look to us to how you want to run it, you you should really take the reins on it. And similarly, you should treat every conversation with an investor both like they’re evaluating you and equal and opposite. you’re evaluating them totally are how leaned in on you. And the idea is there are they? How good are the questions they ask? And I think that’s actually one of the greatest indicators is can they get to that next level of really asking questions that show that Yeah, they get the high level, but really, they understand on a deeper level, what it’s going to take to get this company done because you also want investors that understand and embrace the hard stuff you’re going to have to do.

Kara Goldin  23:19

Yeah, I think that that’s so true. I think that the other thing, just to add on to what you’re saying that I’ve noticed, too, especially when I was going out initially, you get sort of, you know, you hear these names, right? somebody hears that you’re going out and raising money, sometimes they’ll call you sometimes a friend will introduce you. And you really have to look at the companies that they’ve invested in. Because that’s what I found, I never had a problem actually getting the meeting, maybe some people have problems getting meetings, I never had problems getting the beatings, but that’s one hour of your time. Or by the time you actually, you know, go there come back two hours, right, or maybe more. And I think that time is the most valuable thing that founders have.

Lucy Deland  24:10

And yeah, that any of us have. But founders in particular, because you know, you tried, you’re raising money to buy yourself time. Totally.

Kara Goldin  24:19

Yeah. So things like stages, for example, like what you were talking about are things that the newbie person going out and looking for money, you didn’t you don’t really know what stage is and how important that is. So if somebody still wants to take the meeting with you, you’re a brand new company, and they do later stage. Probably not worth your time. If you have, you know, limited time. Do you agree?

Lucy Deland  24:46

I and I think that just to add on to what you’re saying if you can find someone who’s inside the venture or vest in whatever investment community you’re going to speak to, or you can say, Can you just take down The curtain for me and kind of tell me what the market looks like right now tell me, you know, kind of what’s happening in terms of what does a seed mean today? What does a series mean today? Who’s doing them? What are they looking like? Because one of the things, you know that the landscape is shifting all the time. So even if your new venture three years ago, to your example, there are late-stage funds that are now doing seed rounds. So optically, it might not look like it makes sense to meet with a later stage fund. But given recent trends, it actually would. And so I think if you can find that sort of like insider who you say, I’m not trying to raise from you, I just want to half an hour to get you to sort of giving me the inside baseball on what you’re seeing, and what should I call this round? What is if I say that I’m raising a $2 million series A, what does that signal to the market? And a lot of times, they can kind of say like, Okay, this is how people are going to think about you, this is where they’re gonna bucket, you don’t say you’re raising a $2 million series A, that was a joke and not a good example. And so I think that that can be really helpful from the founder seat. And I think that’s one of the things we try and arm our portfolio members with is a little bit of the mindset that everyone’s going to come into their meetings with.

Kara Goldin  26:23

That’s great advice,

Lucy Deland  26:24

because we know from being in a founder seat in the operator seat, that sometimes it’s kind of a mystery, why certain firms react in with, you know, unbounded enthusiasm and someone else doesn’t. And then you find out in retrospect, that you could have predicted those outcomes.

Kara Goldin  26:41

Yeah, I totally agree. What are some of the current consumer-facing trends that you’re focusing on right now,

Lucy Deland  26:48

I have been looking a lot at consumer tech that is really driven at personal productivity or sort of personal time management that has that benefits a lot from social dynamics. So we have an investment in a company called Saturn, which is a calendar app for high schoolers. So managing those block floating schedules that just makes life easier, but also introduces sort of collaborative task management, how do you keep track of all your homework with your classmates, where’s your friend Oh, there and building B, while I’m in building a, so has a social dynamic. And it’s sort of like the first productivity app for a 14-year-old to manage the work that they’re doing outside of just Notes app on their phone. And then another which is really geared, which is going to launch later this spring, which is geared towards parents and organizing and sharing the load of managing the household, and how you sort of unearthing all the work that is being done both to make it more manageable, but also to be able to, you know, more easily answer that age-old question. How can I help you seem busy?

Kara Goldin  27:57

Yeah. How? You have two kids, right?

Lucy Deland  28:02

I do I have a three-year-old and a seven-month-old.

Kara Goldin  28:04

Oh, wow. That’s, that’s awesome. My, I have four that are significantly older. Three in college and one in high school. So um, so you manage through all of this already flawlessly? Yeah, I started hinge when I had four kids under the age of six. And so

Lucy Deland  28:22

yeah, so you had five kids under the age of So yeah,

Kara Goldin  28:24

I was not the profile that most people wanted to invest in. And the best thing is, is honestly, when I run into those people who didn’t really think I could do it, frankly, and now they look at it, and they say they were wrong. I mean, it’s just, you know, and I’m glad that’s okay, at least you owned it. Yeah. Good for them.

Lucy Deland  28:49

There is also a group of people who, you know, have wonderful, wonderfully terrible memories were like, I always knew you were gonna do it. And you’re like, No, you literally did it. I remember that meeting. And it really was not the meeting. And we and now it’s hard for me to say this on the investment now that I sit on the investor side of the table. But how we did always come out of every fundraiser. With one person’s based on the dartboard, we said, We’re like, it’s just important that they’ve given us a gift. They’re the person that we’re going to prove wrong in the next chapter. And you know, when never failed to happen to

Kara Goldin  29:25

Well, I always feel like too, and I mean, this sort of stretches to so many other examples as well. But I always feel that generally, when you’re getting feedback in some of these meetings, I mean, on the one hand, I say some of these meetings aren’t really worth your time, but actually, there’s a lot of meetings where you may disagree with 90% and you whatever, you just don’t think it’s really a great thing, but I always feel like even the challenging ones where I want to have somebody on the dark board or I find I’m having somebody in the dark where there might have been something that somebody says in there, that is Little bit true. I’m always the one that’s trying to pull that stuff out and learn from it right and get better. And that’s what I did in all of those meetings. And so and then later on, and when I would run into them, I’d say, No, I actually remember you saying this. And they say, how do you remember that? And I said, you know, founders, when we’re raising money, we actually remember,

Lucy Deland  30:21

remember everything. And actually, I think the fundraising process, and I don’t just say this, as an investor, I did say this as an operator, is a really special time for reflection, zooming out, getting out of the weeds. And each process can bring you sort of to a new level of understanding, both through the feedback that you get, but also through just being this exercise of constantly explaining the vision in a way that when you’re sitting with your employees, and you’re all bought in, and you’re all just, you know, fighting another day, you don’t sort of getting that time and space to necessarily have those high-level conversations every day.

Kara Goldin  30:58

And you’re not going to have everybody telling you that your baby’s pretty along the way, especially the more serious ones, but I always say to founders, like the key thing is to brush yourself off,

Lucy Deland  31:09

right and keep moving and whatever, know that there are other people that are gonna love you. And you know, but it’s really it’s a lot. And some people ask me, how if, how to know if they’re ready to start a company? And I say to them, well, do you really want everyone to think that this is a fabulous idea? And do you want everyone to be really proud of you know, like, yeah, and I’m like, then you’re not ready? You need to be ready for everyone to tell you, it’s a terrible idea. And to tell you that your baby is like little wonky, and you need to live, you need to just not care, listen to it and be able to take in that information, as you said, and sounds like you’re good at Find the kernels of truth, use them to make it better. But have that sort of internal locus of motivation, confidence, and it needs to be there. Otherwise, it’s I mean, it’s already a hard road, as you know.

Kara Goldin  32:03

Yeah. And I think it’s just a, it’s something that you just have to, it’s a learning experience, and you have to immerse yourself into it. And, you know, I think that the best learnings come where you feel a little bit uncomfortable, right? And yeah, in general, and that’s what fundraising is. And I mean, frankly, I’ve done it for 15 years, I’m the first person to tell people that, including investors that I don’t like raising money, that’s just not what I enjoy doing at all, but I’ve gotten really good at it. And I, you know, and I continue to just go and do it. And,

Lucy Deland  32:38

yeah, it’s necessary and you don’t necessary, it’s okay, if you don’t enjoy raising money, you have to enjoy running the company.

Kara Goldin  32:44

Yeah, exactly. And you have to know that you’re going to go out and raise the capital. And that’s exactly what I do. And where my head has been out for for a long time. But so COVID, obviously, for everybody, I mean, all going on a year, which is so crazy, right? And as we’re rounding starting to get close to these anniversaries, right, it’s nuts. I mean, I remember very clearly, I was closing down, my New York office, and I flew out from San Francisco on March 11. And shut down before the, you know, really, while everybody was shutting down on, I’ll never forget that week on a lot of levels. And we hadn’t closed San Francisco yet, because it really was a lot worse in New York than it was in San Francisco. And of course, we found that out later. And then coming back that next week into San Francisco, and really kind of feeling the effects of, you know, offices closing down 15% of our business went away. Luckily, we had sort of other revenue streams coming into the company, and which ultimately ended up growing our company significantly, but it was, what did you see? And what do you think are the big shifts that you saw Justin, in companies,

Lucy Deland  33:58

I think a lot of companies that were that we were looking at that were pursuing a model where they believed that there was still importance in brick and mortar or some in-person experience, and that they would have a digital sort of arm to it or a software play very quickly, you know, quadrupled down into the software element in a way that maybe would have taken five years to really embrace it and really say this is a number one priority, such as our, we have an investment in a company called chief that is all around it’s like a YPO model for senior women’s great and they had in-person meetings for their cohorts. And obviously, they had to shift and I think, in so many ways that are going to be a long term transformation of a lot of business models towards really deeply embracing software as the delivery mechanism and Flipping any brick and mortar or physical into, you know, a nice to have or a different role than it plays, it will not eliminate it forever. But it really accelerated the focus on that. And so I think that that’s been good in it. And that might have also like, bolstered the confidence of some of those CEOs that, you know, we can build a really good software product here and people and our customers are ready for it.

Kara Goldin  35:22

Yeah, it’s interesting, I think there’s still a link missing for a lot of these people, though, that was as, as you kind of described that they were thinking about it as an add-on to their existing business. And I think that the piece that so many of these people are missing is that, while it’s just as important, and maybe during a pandemic, it, you know, sort of makes up for things. I think that on the data side, there’s so many people that just don’t really know what that is, and sort of why it’s important. They’re just allowing others to kind of take their data. And I mean, so many people just, at least in my industry, think that going online is just working with Amazon, right. And they think they’ve solved it. And it’s all

Lucy Deland  36:09

just a logistical problem, not a

Kara Goldin  36:11

right, they just don’t really understand it, and especially the physical goods side of it. And so it’ll be interesting. I think there’s still growth to be had there. And maybe there are some new companies I keep looking at, what are those new companies that will crop up out of that? Because I think that there’s just definitely this whole operation side of the thing that I think so many of them don’t get, and it’s not just about throwing a lot of ad dollars at Facebook or Google. Yes, you need to probably do that, too. But yeah,

Lucy Deland  36:41

that’s one that’s a very shallow first step,

Kara Goldin  36:43

right? And how can you just get better at ultimately understanding what I keep saying over and over again, my biggest learnings from 2020, is that the customer is really in control, more and more about how they shop, what services they buy. And, you know, I just think it’s, it’s so, so crystal clear. So it’s really, super interesting.

Lucy Deland  37:07

So the best piece of advice you have for entrepreneurs and founders, this is advice for the day to day or the year to year, but run towards the hardest thing first. So I think as people we have sort of a psychological habit of, you know, taking off the stuff we know we can do. And it’s sort of I think in the entrepreneur seat in the founder seat, you have to go towards the problem that you’re not really sure how you’re going to solve and go solve that part of the customer experience. And similarly, you know, the part of being a founder is, as soon as you know, someone else on your team can do it, it’s got to be off your plate, no matter how good you are at it, it’s got to be delegated. And so I think it You said it earlier, you know, the place you learn the most is outside your comfort zone. And so founders learn to live exclusively outside your comfort zone, outside of your skill zone, and outside of your company’s comfort zone at all times because those are usually the most important things to be doing.

Kara Goldin  38:06

I think that’s so true. And I think that you touched on another thing that I always tell founders and CEOs that I think is really critical, though, is understanding a little bit about everything. Because if a person in your company leaves or you know, there’s a problem that they are having a really challenging time fixing. If you can actually get in there and try and figure out even if it’s not your lane, you can come in and go in and support and

Lucy Deland  38:36

be well and I think that’s also very crucial for hiring as well. Where you are going to hire the better talent to be able to evaluate it more, the more you expose yourself to every part of the business.

Kara Goldin  38:48

I think that’s so critical. I totally, totally agree. Well, this is amazing advice. And I love hearing just that you went from one industry and finance into a company and then went back to finance Do you think you’ll ever go in house at a company again,

Lucy Deland  39:09

I think I’m pretty heads down for the next couple of decades but never say never. And I also loved building companies so I would never cross it off the list.

Kara Goldin  39:18

Well you’re in a great position to because especially in that early stage, they you know, these companies need help and support so it’s

Lucy Deland  39:26

fun. I know I’m in a privileged position where I get to work with a bunch of founding teams all the time and get those high highs and those low lows and they come fast and furious both at the same time often

Kara Goldin  39:39

that’s super true so well great. Well thank you so much Lucy for coming on and everybody give Lucy five stars and definitely come back and see us on Mondays and Wednesdays every week. We’re meeting with lots of amazing people with great insights and different interests. And journeys, that some are. Actually, none are really a straight line. I feel like the most interesting people that we have are sort of bouncing around and doing things not exactly the way that everybody does it, which is really, really interesting. So

Lucy Deland  40:15

to those who can career plan that well, I give you kudos.

Kara Goldin  40:19

I love it. And where do people find you too?

Lucy Deland  40:21

You can find me at Lucy uninspired capital calm into my inbox, or actually, my Twitter handle is confusing because it is my maiden name Lucy Grayson at Lucy gra Ysn.

Kara Goldin  40:34

Got it. Okay. Well, thank you so much, and we’ll see you all very soon.


Thank you so much, Kara.


Thank you.