Today I am chatting with Carey Ransom. Carey is the founder and president of Operate. Operate is a prominent Orange County ventures studio. At Operate Carey and team partner with the earliest stage entrepreneurs to build great products. Before Operate, Carey was a serial C-level startup executive, and Carey also has a podcast, The Operate Podcast, where he talks to both investors and operators. Hi, Carey, good to see you. Thanks Minnie, it's great to be here.
Great. Well, I am excited to talk about your podcast, but let's start with Operate the venture studio. And I'm curious, you know, when you were setting it up, I think you told me that you, you looked at a number of different models, different venture studios.
I'm curious, you know, what you thought about the different potential structures?
Sure, yeah. If anything, I would say I didn't set out to start a venture studio. I think we felt like my partner and I, felt like a venture studio was probably the closest structure to what we felt like we were best served to offer to the market. And so we said, well, we'll call ours a venture studio.
And I think that still is a constant question that we have. I think we, we sort of think of ourselves as just Operate, and the studio is a part of that. And, as far as models go, I think you know, the original sort of venture studio really is right in Pasadena with Idea Lab and the primary was, I think, often someone similar to Bill. I have a bunch of ideas I'd like to see if I can help push a bunch of these forward and maybe I'll go really focus on the one that takes off.
I think what we felt like was missing has been find that founder or the founding team with a kernel of something really interesting, and so, our view was we know they need capital. We know they need a lot more than capital and if we can find ones that we can love and we can support in a multifaceted way, that's really what Operate was all about. Right, and so that distinction is for you, your model it still mostly is really early entrepreneurs coming to you as opposed to your own ideas.
Uh, for sure.
Yeah, and it's one of the things I love about your model is that I think you have said are no entrepreneurs too early, right? I love that.
So tell me about those entrepreneurs. So they're early in their journey what are the founders usually look like and what do you usually helping them with?
Yeah. Great, great questions. So I would say most people still come to us with the notion of, oh, they could be early check, first check. You know, they're generally coming to us first for money because most of the marketplace is saying to them, put a pitch deck together, pretend like you have it all figured out and go try to convince some people to give you money so that can go try and figure it out. And so that's often how we see people.
Of course. So you're giving money, but how do you describe the work that you're doing when it's more than money or what's a good example of that sort of thing?
And then I think under that we see sometimes really technical founders. And in those cases, what, where we often need to help them is on the, Okay.
Not necessarily build first, but let's go validate. There's a real problem that people are interested in having solved that they're willing to potentially pay for. Can we do some early customer development before we even build, because let's, let's make sure we know that we're actually on the right track to building the right thing.
Uh, and so that's often where we'll, we'll partner with a technical founder and sometimes that's a good, healthy conversation. And sometimes it isn't. And we use that as somewhat of our determination of whether this is the kind of lovable, collaborative, coachable founder that we really want to work with.
So that's one class for sure. And we've had some great success. With some folks like that. Uh, we also have what I would characterize as the subject matter expert type founder who may or may not be technical, but realizes that there is a critical market problem that they deeply understand. Often they have that insight that I get really excited about that they just, they see something earlier or maybe differently than others in the market that they're in.
And they really are excited to solve it. And in some cases we've had to bring technical resources to help or build resources, to help them on the product design engineering side, just from our bench and network to really help get that off the ground. And then I would say the third is maybe a little bit more formed initial founding team.
And in those cases it's just design determining if we can be a force multiplier. For them, maybe it's additional heft in key areas. They need help on go to market or product maybe in technology or just executive kind of, and strategy support to say, Hey, you've got, and we have one of those right now that we're really excited about.
They've got a great start and we're kind of supplementing them in, in a whole bunch of areas and also helping them get this launched. And they, they, you know, were on the track of, of building something. But weren't exactly sure how they wanted to go launch and learn. And I think what we have a really good discipline and muscle around is how do you develop a rapid learning plan in the early stages?
Because I'm very adamant about, you know, trying to increase your rate of learning early on that you're really just an experiment that you're trying to validate and invalidate as quickly as possible to find where then that real opportunity. Yeah.
Yeah, anything non-intuitive or sort of special to what you're doing. They're just getting product in market, talking to users.
Yeah.
I think we kind of customize it per business. And it, you know, I would say if anything, it's just a function of, I've worked in so many different industries and sort of so many different types of business models from direct to consumer to direct a business, to things that are entirely channel driven, that we can sort of explore various options and in the early stages and say, okay, what is the best way for us to potentially go validate or invalidate?
And, you know, we have one business for example, that right now it's direct to consumer, but my partner and I would probably say in our gut, we believe that ultimately will be a B2B distribution business. But we had to go prove we couldn't really find anybody. We felt like in the B2B channel early on, that would jump in because it was so early that we said, if we go prove it direct to the market, then they're going to want this because this is a really high value for their end consumer customers.
And I think what we have a really good discipline and muscle around is how do you develop a rapid learning plan in the early stages?
Because I'm very adamant about, you know, trying to increase your rate of learning early on that you're really just an experiment that you're trying to validate and invalidate as quickly as possible to find where then that real opportunity. Yeah.
Uh, and so that's often where we'll, we'll partner with a technical founder and sometimes that's a good, healthy conversation. And sometimes it isn't. And we use that as somewhat of our determination of whether this is the kind of lovable, collaborative, coachable founder that we really want to work with.
Um, but we'll go prove that first directly, but ultimately our brand may need not need to exist. We'll see. And so I think that's, that's maybe the unique perspective is that we just, we started don't have a single path view of the way the world is or has to be.
Yeah. So a few things you said, so you said lovable a couple of times, which is adorable and lovely. Um, but here's my view of you, Carey is you say no founder, no company is too early. I think you've said you think VC's, over-index on founder experience. You're looking for someone lovable. So you're taking these people who are first-time entrepreneurs don't have that much traction and you're, you're loving them.
I don't know how else to say
Yeah. here's what I think about it is we're energized to help build things that.
need to exist in the world that are going to dent the universe in some meaningful way or change things in some really meaningful way. And obviously create a lot of value. And I think we want people that we get excited when we wake up in the morning.
Oh, we get to work alongside them today. We get to help them. You know, it doesn't mean we don't have hard conversations. It doesn't mean that we don't. Sort of have conflict and challenge each other, but I think we want people that we can be excited that they, they are lovable. And that doesn't mean they listen to us.
That doesn't mean they, I mean, it's like, I think of it. Like I, you know, I have three kids and my kids don't always, uh, listen to what I demand they do or advise that they do. And, you know, I feel like in some respects, entrepreneurs or founders are, are a little bit the same way and that they need to know that there's, uh, unconditional support.
And there's an underlying foundation of trust and, and love there. And that the end of the day, we want them to be their best self through this. at this point, it's, I'd rather optimize for enjoyable people that have that mutual respect and trust. And so I think that's, that's where we use the term lovable and people can be lovable in a whole bunch of different ways.
We all have our uniquenesses and quirks. I think we, we embrace that diversity. And how do we, you know, as long as there's a high degree of trust, I think we can, we can find ways to have that.
I like that. We're getting kind of philosophical here. all of us are lovable. I also think you're very missionary in the way you talk about this work. So tell me more why this is such a mission for you.
I, I think it's critical. just to us as humans that we can go find our place in world. And for a lot of people, they have these ideas or they perceive, Hey, this could be way better or different. And that, to me, that that's something we as a society, I mean, historically in the history of America, We were founded by entrepreneur misfits, who, who came here. And so it's, to me, it's like the culture of our country. And so I think that's where it starts for me. I believe everybody should have a chance to try to pursue that. And I think the venture world likes to pretend like that's the case. And I think it's actually been a very exclusionary, somewhat clubby
environment historically.
And if I look at where, where I am, particularly in orange county, but also in Southern California, you have incredible diversity of the elements and attributes that you would look at in the population. But you have people going to community college, or you have now an increasing number of people here who are first in their family to go to college and they don't have this network.
But they are demonstrating. They have the grit and determination to go improve their lives. And I go, those are the people that are probably our next set of entrepreneurs If you've got that spark of genius, it's really about just helping assemble the puzzle around you. And for me to expect that you have to go figure all that out on your own, I think is just dumb.
And so we feel like that. I mean, to me, that's the mission is that this should be a much more democratic, operative.
Great. And so you're writing a few hundred K initial checks.
yeah.
our range. And we kind of look at it because of the fact that we're willing to contribute our team into these companies as well. We will look at that in many cases in lieu of putting capital in. So they need, they may need a half, a million dollars of investment. And we may put in a portion of that in capital and a portion of that in our team.
We haven't done any where it's entirely just our team and we have done some, as I said earlier, where we have done just some investment only scenarios as well. Usually we're not doing that all by ourselves. Usually if we're doing that, we're either doing it alongside others or we're immediately going.
Yeah. Bringing in co-investors or we've done scenarios. I think, um, we've talked about previously where we'll even do SPVs at times alongside a investments. So our view is we're in the business of how do we help when we find that founding team that we really want to partner with? How do we bring all the capabilities we can bring to help them move it forward quickly and effectively?
Got it. And so for the SPVs, um, I do think that's an interesting topic. Um, are you sort of creating, do you have like a big following on angel list where you, you know, routinely do this or do you sort of have your LPs and people who, you know, are interested in investing and you will pull that together?
Okay, so invest in, and then I think you said you've doing some SPVs. And what do those look like for you?
in most cases they've either been, investments that we've already made, that we're doing a follow on investment into, and now bringing it to our network, or in some cases we've done them alongside an investment we're making from our fund because the company needs more money than we're able to bring out of the fund at a point.
And so we'll just do an SPV alongside that. And we have that where we'll take it to our LPs and we'll say, Hey, here's an opportunity if you really liked this one to go deeper than you're going to get exposed to just in the thought
let's talk a little bit about orange county because you're in orange county, as you said, getting democratizing access to, to, to building, to sort of realizing your vision. What does orange county have? What do you what's the view there?
that is a great question. And I, you know, I like to believe I am more involved in the, and know more people in the early and growth stage venture community in orange county than probably anybody else. Cause I've been very actively building those relationships for almost 20 years now. you know, orange county is doing great in med device and you know, on the health care side of the world, we have great companies emerging in ophthalmology and aesthetics and medical device.
And I would say those are probably the, the areas of highest. Growth and potential right now and not my area of expertise at all. on the more traditional software based tech side, I think we're still trying to find it. There is a vibrant community. We have pockets here and there, or I would even call it kind of one-offs.
and so we aren't unfortunately doing as much in orange county as we would probably ideally like, but we're very so Cal focused. And so as I look at us now, almost not quite two years old, um, we're increasingly doing more and more in LA
and we're doing a little bit in San Diego and we kind of look at it as, Hey, we're in the middle we're, we're in a good place.
Uh, I think COVID also made us more comfortable with the idea that. Being not every day together, we can still figure out how to support our companies, uh, in a hybridized see them and virtual environment. So we've, you know, we, we didn't change our footprint at all, but I think we're, we're just trying to go where the founders and the opportunities are with a focus on Southern California, because we feel like this is a region that has so much vibrance from call it Santa Barbara to San Diego.
And, you know, the, the big companies, particularly now after the COVID experience, I think we'll probably end up with very different physical footprints. If they've tried to grow here in the next decade and they may end up with multiple nodes, you know, the, the trip down the four or five and five to build out a company.
25,000 employees here or something. And so I think we feel like we can birth those anywhere in the region and then support them along the way. And so it's more important for us to all be interconnected and supporting each other to, I think, you know, really raise the region together. So that's why I love being able to build relationships with folks like you,
Yeah. Yeah, I still think of orange county as having a lot of semiconductors. Is that still true?
which is, and it's actually making a significant comeback.
Hm. And great surfing and real estate. do you find like a lot of LPs made money in real estate or is that a misconception?
Uh, there are a lot of people who have made money in real estate here. Most of them are still making money in real estate So I think the hardest thing. Is to get them to allocate any amount of capital. So, we have a few who have done well in real estate who will dabble, because it's, interesting, or maybe their kids are not doing real estate and interested in tech or something, but that's been probably the biggest challenge from my perspective is I look at it is if I have am heavily invested in real estate, in Southern California, then the best way for me to protect that investment is to invest in the job, creating entities that are going to produce the, the high wage opportunities that keep the people living in my apartments, shopping at my stores, working in my offices, et cetera.
And for some reason that has not been nearly as intuitive to others, as it seems to be.
And are you from orange county?
I'm from Indiana.
okay. Well, good transition. I think you had, you grew up your family had a family business.
Yes. So I grew up, yeah. I mean, I can give you a little bit of
yeah. Give me the background.
So I'm from a small town in the middle of Indiana. and when I showed up in the world, uh, I was born into a family that had a family business that was already a hundred years old. When I showed up,
What is it
do?
we were the local retail lumberyard hardware store,
Oh,
and it started by two brothers in the late 1870s.
So you can figure out my age and, you know, eventually my great grandfather married the only daughter and took it over. And then, you know, my dad and my uncle were. Principally running it when, when I showed up. And so I grew up in this business and it was a really interesting way to learn about business and learn about community and, family connectivity into that.
And, you know, people who were involved or weren't involved in a lot of those dynamics. And I think between the location of it, I learned a tremendous amount, but I think between the location of it, uh, in the small town and the business itself, that just seemed to be getting increasingly difficult. I determined it just, wasn't a great fit for my life plan
and
Can I just ask about your childhood and just the family business a little bit, which is, did you, did you feel like your parents did a good job of like teaching you business through the family business or whether you I'm just curious, like, uh, I'm curious about family businesses and whether you felt like it was things your parents did, right.
Things they could've done better.
So I think, I mean, I was able to, I started working when I was probably 10 and, you know, it was, I was just, uh, always been a very curious, you know, if you're asking my mother, I was curious, precocious and uh, just always interested in things. And so I wanted to know what my dad was doing. So I was like, I'm going to come down the store.
Can you? And they just kept me busy, gave me things to do, and I just would learn something and do something. Okay.
Is there something else? Uh, so I think, yeah, I learned it more by experiencing it and doing it than being taught if you will. I mean, I was taught through no, don't do it that way, do it this way, but it wasn't there, there was not a true classroom, but I, I did learn a fair amount, but I actually, in retrospect, wish it had been a little bit more exciting.
Probably because I probably would have gotten to some other conclusions faster, but as life went on, I would apply a lot of the experiences or situations to, well, how would, how would my dad have handled that? Or how would my grandfather handled? That was always a filter that I would try to use. And so I, I did have enough experience there that that really helped.
And so often I've, I've said, I feel like most of what I have needed to learn about business, about people, whether that's employees or customers, partners, and even community, I feel like I learned growing up in that business. And so it's served me as sort of a core foundation incredibly well. Uh, I just didn't, you know, looking back, I just didn't love the actual business and I would have no doubt.
And I talked to my dad I'd liked about that. I would no doubt tried to change it or certainly have changed my role in it, not needing to do the same thing every day. Uh, and that probably would have caused a lot of friction. So we, uh, I think we have a much better relationship, uh, as a family, as a result of
Hm. Yeah. I'm always just fascinated how parents can expose their children to, to business. Um,
well, it's been fun. I mean, now, you know, the beauty of now with having three kids, uh, I just sent my kids a text yesterday with a link to the app store to download one of our newest company's apps. I said, tell me what you guys think, because I actually found that their feedback. On things like that is incredibly valuable and it is me trying to attempt to get them somewhat involved because I, I totally agree with how you're thinking about it, that I think there are incredible life lessons to teach them through that.
Yeah. Um, but, okay, so you left, uh, you left the lumberyard hardware store and my summary was that you've been a serial C-level executive at a number of startups. Uh, I'd love to hear about some of the, the sort of formative experiences for you.
Sure. So, I mean, formative would be, you know, decide not to do that. I actually, I started my career at Proctor and gamble and I, you know, got into this company that a lot of people are really excited to go work for. And I quickly realized I wasn't excited. And I was on this fast track management development program and realize I didn't want any of the jobs that were in that chain.
And so within the organization, I explored a little bit to see if I could find something that was interesting. And I did a couple sort of intrepreneurial things in my early days there until they decided I needed to really do something, uh, important. And I said, okay, I probably need to go now. And so one of the projects they did there in both software, and I said, this is where I need to be.
And so when I left, I talked my way into a enterprise software company and I took a sales job and I was probably at least 10 years younger than anybody else. And this was before the days of the SDR model and. Literally, you know, sharing a bag, calling on big companies, trying to figure out how to sell big ticket software.
And I did fairly well. And I think from a formative experience standpoint, I realized, okay, I can, I can do these things. And that it wasn't just about having a bunch of experience. It was if you were really good at adapting and learning and paying attention that, I wasn't the best salesperson, but I was often the best friend of the product team because I was bringing back and understanding how they wanted feedback more than salespeople, who often are saying it needs to do this and he's to do that or, or whatever that relationship often could be.
And so I started to think about, okay, well, why did the best salesperson just get promoted to sales manager? Is that. The right decision, if they're really good at that, why aren't they in that role? They're not showing that they have great management capabilities. And so, you know, was involved in a couple enterprise software companies and then the.com crash hit after that.
It wasn't immediate. But after that shortly thereafter, the company I was in was starting to struggle. And I said, okay, this is going to probably take a little while. And so I used that as my excuse to leave Chicago. And that's how I got to LA. And so I came out here almost 20 years ago during, you know, in the aftermath of that to just wait it out.
And I said, oh, grad school is my excuse to move out here. And drag my wife from Chicago, let's go have an adventure. And a weekend, we looked at each other and said, I like it here. Maybe let's stay here a while. And we've been here ever since. And so I think that first was kind of the, oh, okay. I can do this.
And you know, the second one was once I got here, I decided, well, I need to build a network. I've got a bunch of classmates, but what's going on here. And so I went out into the, uh, into the market in LA and say, okay, are there interesting software companies here in LA? And you know that a couple of decades ago there weren't many.
And I happened to meet, a founder of one who was based down in orange county, where at that point there were more software companies, I think, and even in orange county than there were in LA probably 20 years ago. And he was a technical founder. He had a product and one customer, and he was looking for uh, you.
know, air quotes, VP of sales.
And we met and found that we had really good chemistry. And I said, I think I can get you more customers. I think that's what you need Right.
now. And I'm a. Business school student I'll do it for equity because I've figured out how to live. And I think this could be really interesting. And so that was, uh, another really formative experience because I just said, I'm going to bet on myself and what I think he's got here.
And we grew the company really quickly and actually exited it really quickly. And we sold it to a venture back company that I had met, who was a great strategic partner, because I, I got to a point where I said, well, I just don't want to keep cold calling and selling every day.
How do I start to scale this? And I found, uh, a partner that had a bunch of salespeople that we were a nice fit with and may decided they liked it even more than a partner. They wanted to buy it. And that's, that's where I often will use the term. You know, business development can often be a great form of corporate development and the partnership turned into a merger.
And then Microsoft bought that combined company about a year after. That. And so, you know, really the kind of transition experiences for me that led me to say, okay, this is where I need to be. I just need to go find the opportunities that fit my personality and where I can contribute. And what I started to really optimize for in some respects were what I would call 50% jobs where, you know, I knew 50%, like in the case of of message.
Right. I kinda knew I, you know, I knew I was going to go about selling it. I'd sold SAS previously. I kind of had a sense, but I had to go run Google ad words, campaigns, and figure out how to get people onto our website because, um, I, I didn't want to just pick up the phone and cold call every day and want people to come to us.
And so that was a part I got to really learn and then think, about the strategic partnerships. And so then each kind of incremental role from there was sort of 50% I had a good sense of and 50% was something I was going to have to go figure out and learn. And that really excited me and got me energized to work all the hours that you often need to, to contribute into a, an early stage.
I think, um, I think that was a great big lesson, which is the, I can do this lesson. Um, I mean, I think that's actually, when people say you need to go iterate, it's just believing that you can go run the Google ad campaign and talk to users and all of those things. Um, what about app startups? Any thing else really stand out once you, you know, now we've gotten you to, to this startup you C-level startup role, any other big, you know, maybe, uh, I don't want to say misses, maybe like, you know, hard lessons learned.
and any other big lessons learned from your startup experiences?
Well, there was one, that I started that now goes on it's 17 years ago. I guess we started and my partners were in Seattle. I was in orange county at that point. And so this was after we had sold the company and we had a great idea. Amazing idea. We were, I mean, you know, it's almost sad for me to admit it.
We were building marketing automation before marketing automation as a term and really existed. And we were doing dynamic constructed email on a one-to-one basis. And you know, the, the challenge, wasn't the idea. We actually got some customers, we got some revenue, um, but my partner's not. All did it initially as a moonlighting exercise and we were remote and we were using Skype and the collaboration tools at the time.
But what we were talking about iterating, we just weren't moving and iterating and learning fast enough because when we started, none of us was full-time on it. We all had different tensions and different abilities to, to contribute. We had the right mix of skill sets, but we just were never able to get on the same page.
And so I'd move ahead with some customers and have a sense of what I thought we could deliver to them in the timeline. And then we'd extended and then I'd be frustrated and the customers would be frustrated because they couldn't get it on time. And then that strained our partnership. And so really the hard lesson there, because we ultimately walked away from the opportunity.
And I think there were a couple of key lessons for me. One, one. It all things being equal. If you can try to get equal commitment in the early stages from the founders, and ideally you'd be co-located physically together because you can do, you know, you can move no faster than your slowest, contributor at that point.
And if you're all there together, you can sort of make sure everyone's at least close, closely following each other. And so I've tried since then for anything really early to make sure people are at least co located, unless there was already a strong operating history in our relationships and existence.
And so that was one. And then I think the other is this idea of, there are times when you're on the right track that you just have to survive long enough until the market arrives because it wasn't too long after, uh, That some of these companies started to emerge and that was frustrating. And, you know, when I built, when I finally built another marketing automation software company, many years later, um, I had a, a head start because I had done it once and I knew where the value was, but, um, we were by no means the, you know, early entrant to the market at that point.
And so I think, you know, surviving is, is a key lesson when you know, you're you're onto something.
Yeah. One of the podcast episodes I did was with my partner, Gil Elbaz. And he said like, look, just if startups fail, but the ones who can make it 10 years, they're less likely to fail if the person's like just going to do it 10 years.
that's right.
okay. Anything else? I do want to talk about podcasting a tiny bit, cause I want to pick your brain.
Should we move there? Your podcast is the operate podcast.
Okay.
And you know, I'm just so curious. How long have you been doing it now?
So I've been doing the podcast now for two years.
me too. Me too. Um, do you think you've changed? Like has your communication, do you notice that, like you ask questions differently or have you changed as an interviewer?
That's a great question. I'm sure I have. If I go back, I haven't gone back and read, listened to my early episodes, but that's, this is a good question to catalyze me to go do that. I'm sure that I have, I feel like I have been a podcast interviewer for a long time, because when I started the podcast, what I told a bunch of my friends who were many of my early guests, and, you know, at one point I, stood up in front of a big group and said, I'm going to start a podcast.
And all of you are going to be my guests to start. A lot of them I've been having coffee or lunch meetings with, for years. And in a lot of cases I was interviewing them and that was the conversation. And the goal was to make it much more conversational. So I probably participate in my podcast more than some people do.
And that it's maybe a little bit more conversational than just me question, question questions,
I think a lot of the best interviewers make it at least seem very conversation.
yeah, probably. And I, because I've worked in so many different spaces and I read and very divergent things, I, I am at least able to have a short conversation on most topics and I'm fascinated by so many things. And so I think that helps me in a, in a podcast because I can, oh, I just read about something the other day on this topic.
And that helps inform me to at least feel like I can participate in the conversation and it's not, uh, just a completely, completely uninformed, uh, set of questions.
how about any, uh, have there been any moments or any interviews where that have really stood out for you where you've know? Oh, that was so good. So interesting. I feel like I listened harder on my own podcast.
Yes. I mean, the ones that are probably been the most meaningful for me is when they're just this incredible emotional connection. Um, you know, a guy that's become a really good friend. He broke down because of just how passionate and he felt about what he was saying. At that point in time, and that that was super memorable or, you know, another friend of mine who just is so vulnerable and transparent in how she communicates and that really drew me in.
I think those are the things that have, have influenced me to just think about my communication style more recently. And, and I think those are moments that I, I I'm learning something here. So, um, you know, pay attention to that. So those, those are the things that I think are really fun about it. And, um, I try to always tell my guests, I'm not trying to get a scoop or get you to say something that you know is an aha or anything.
I really just want to share what otherwise might just be the two of us talking with other people who may or may not be interested, but I know I am and that's enough.
Yeah. Um, so we've been, you did say that this is what I'm fine, which is, I do think my communication has changed from having recorded all of these. And so you said you heard this woman who was more vulnerable in her speech, like, has that changed how you view your own speech
for sure.
and made you what, like more, speak more with more emotion, more.
At times I think it just, it, it showed me how powerful that can be. I don't, I don't necessarily use it all the time, but I think if it's something you say, okay, if I need that, that, that, that is something I should really think about. I mean, I I'm, I feel fortunate in that. I think I've been very comfortable being who I am for a long time.
And that I feel like was a gift from my parents and. So, you know, it's worked for the most part. I'm sure there are times that, that people don't love who I am and that's okay. You can't ever please everyone. But, um, I feel like people know who I am when they get to know me and like this isn't a character.
I mean, we're all characters, but it's a consistent one.
Do you have sort of unpopular views or things that you're like, well, it doesn't matter to me because I'm comfortable with that, that you don't have to like me for my unpopular views.
Uh, yeah. I mean, I think most of mine are probably about, sort of the, how we keep score of, you know, in, in looking at people or achievement or, what success actually means. And, you know, we're, we're definitely, and I'd say, you know, particularly in orange county, you, you have. Material wealth and, things that at times are, are challenging for me to, to deal with because, you know, I think if we don't have a, a society where people have at least a sense of equal opportunity, I mean, you still have, I don't know, 150 million people in the world that wants to migrate to the U S to pursue the American dream.
So it's not completely broken, but I think those of us who are here now, it's much harder to achieve today than it was 50 years ago.
And so, I, those are probably the views that I, I sort of try to, uh, figure out like how to, I think by creating more entrepreneurs, we're probably creating more people with the potential to achieve that.
And I think those are where, um, I, you know, at times I'm very comfortable with my view on it, which I don't think is, is, uh, unfortunately really affiliated with any. Existing group in any clear way, but I think there are a lot of other people that sort of have and wrestle with some of the same challenges as far as how they think about, you know, how do you direct your talents and energy to have the biggest positive impact?
And so, you know, the advantage of measuring it on things like money and wealth is that it's very quantifiable. Um, and so, and I don't buy into it, but I worry. I mean, well, I think, you know, how do you, how do you quantify that? Or how does it, how do you think about something like measuring your success in, like, I, I don't know if is enabling entrepreneurship, like what do you, how do you think about that for you?
it's actually something what I've chosen to do is just not measure. And you?
know what, the way that I rationalize it, many, as I say, okay, you know, there aren't many people that come from a family business that lasted 146 years. And the only reason that it doesn't exist anymore is because my dad wanted to retire but it was a very sustainable business.
And there aren't many in the history of our country that have persisted that long and part of why it worked so well, if you really start to look back is at no point, were they trying to profit maximize on a given month or quarter or year? And it was about how do you. Create a sustainability of its, uh, providing, uh, a fair income to the families involved.
It's supporting the people that are showing up every day to support the customers and work in the business and the community at large, that is benefiting from it being there. And then also providing resources to the safety net and social aspects of the, of the community as well. I mean, my grandfather and my father started a program where they build a home every year And they've trained thousands of people in relevant skills through that. And that's just a part to me.
Those are high impact. And that I don't think can be achieved through a single number. And I think where we as a society in many respects have lost our way is by trying to boil things down to a single number, as opposed to accepting that the world is way more complex and complicated than that. And we have to be okay with maybe more of a triangulation when it comes to how we measure.
And that's what gives me a ton of excitement about this notion of impact or ESG investing in that people are accepting. Hey, we need to think about these things in a, in a little bit different way than just a single number, like IRR MOIC or something like that. And so I, I, I'm an abundance thinker as I think, you know, and so my view is I think we all can do it.
So I think that's like we look at it as like
I'm going to compete. as A portfolio, not on,
you know,
do I have the biggest winner? I'm going to look at it as, can we get eight out of 10 or 9 out of 10 of ours to success? Because I actually would rather have more people having some modicum of success,
thn
Hmm. Hmm.
than one out of 10 wildly succeed and everybody else fail
That's a good perspective. I like
that.
sorta how I think about like, I'm going to compete by trying to help as many of them be successful as I can.
Let me think about this. I mean, like, these are the things that just blow my mind are you've got these like foundations and pensions and endowments that are literally trying to invest capital on things like a single number. And you go like, that's not your, you're not even being held accountable in the right.
way. Right. I mean, you take, you know I find it horrid. I'll give you an example of that. The orange county pension funds, aren't investing a single dollar explicitly into orange county.
Right. I know I knew where you were going.
Or LA county for that matter, this doesn't make sense. And yet the system is totally not aligned, even close. It's totally misaligned.
And my view isn't it can be, I don't know. that it can be perfect, but you go, come on
Hopefully you can work to change that. And we're going to run out of time because I have more questions, but, maybe the flip side of that,Carey , what keeps you up at night?
How I feel like, you know, the, probably the, at times the things that keep me up at night are, am I being too idealistic? should I, take the faster, easier path at times?
Hmm.
you know, am I crazy? and so that's one side and then I think the other is, is I often really trying to evaluate am I best utilizing the gifts and talents that I have in the world?
And so that's something I question from time to time. I don't these days, I feel like actually these last two years are probably the most activated I've ever been.
And so I feel like I have. Reached a place where I am probably as close to fully utilized and deployed as I can be. Um, but those are the things that have kept me up at night.
Um, you know, thankfully I've really helped the kids and family and those things give me a great foundation to work from.
📍 that's great. Curious. I love, I find it talking to you very inspiring. Um, and I'm glad that you are doing the work that you're doing. And I look forward to crossing paths more in the Southern California ecosystem.
We absolutely will.
Great,
Thank you for having me.
great. Thanks for coming on. All right. That's an hour. And I tell my editor, I, so we edit pretty heavily.
That's there's a ton of content. My editor is not going to like it. Cause I taped for too long and then he's grumpy. Cause I tell him to make it, uh, you know, I try to make them 25, sometimes 20 minute episodes. There's no chance here, but, um, there's a lot there. I really like.
I have a tendency to go at times.
Yeah. I mean, I really liked the whole, the whole theme we were just on it's so, I mean, it comes up again and again, whether you're talking about lovable founders, it helps me understand you better.
Actually, I like it
Well, I appreciate that. Let me think about this. I mean, like, these are the things that just blow my mind are you've got these like foundations and pensions and endowments that are literally trying to invest capital on things like a single number. And you go like, that's not your, you're not even being held accountable in the right.
way. Right. I mean, you take, you know I find it horrid. I'll give you an example of that. The orange county pension funds, aren't investing a single dollar explicitly into orange county.
Right. I know I knew where you were going.
Or LA county for that matter, this doesn't make sense. And yet the system is totally not aligned, even close. It's totally misaligned.
And my view isn't it can be, I don't know. that it can be perfect, but you go, come on there. There has to be a better way here. Um, and I think those are the things that I think, you know, at times really challenging.
Hopefully you can work to change that. Um, here's mine. Let me give you, I didn't want to say on the pilots, but like I'm so competitive. Like I was just born competitive, I think. And yet I'm not motivated by money. Like I not, they don't, that's not my, it doesn't, it's not what I set out to do. Um, and yet some of the, like the, the sort of more motivating work is very hard to.
Quantify. I can't compete on it in a sense like, and I just, I don't like saying that because I feel sort of crass, but that's what I was trying to ask you is how do I reconcile wanting to compete on something? Cause I find competition so motivating.
And I, I mean, I love to compete. I mean, I'm, I'm, uh, I know you you'd put in there about sports. Like I was probably one of the hot, which probably hard to believe because I just needed to mature. That was one of like the hottest head competitors. I would yell and throw stuff when I was playing tennis. And I, you know, I would get into fights with people.
I shouldn't get into fights with when I played basketball and, you know, just really, cause I just wanted to win and I always want to win that's who I am, but I just feel like, um, you know, you can do in a lot of way, different ways I guess is how I kind of what I've gotten to. And um, you know, everybody should be able to win at some level, I guess is it's it's about like getting them into the place where they can best have a chance to win. So I think that's like we look at it as like
I'm going to compete. as A portfolio, not on,
you know,
do I have the biggest winner? I'm going to look at it as, can we get eight out of 10 or 9 out of 10 of ours to success? Because I actually would rather have more people having some modicum of success,
thn
Hmm. Hmm.
than one out of 10 wildly succeed and everybody else fail
That's a good perspective. I like
that.
sorta how I think about like, I'm going to compete by trying to help as many of them be successful as I can.
That's good. I might ask my editor to put that back in. I liked that a lot. Okay. Well this was great. My editor will yell at me. It'll be great.
Um,
Great to see you.
great to see you. I'm sure. We'll talk soon.
Right, and so that distinction is for you, your model it still mostly is really early entrepreneurs coming to you as opposed to your own ideas.
Uh, for sure.
Yeah, and it's one of the things I love about your model is that I think you have said are no entrepreneurs too early, right? I love that.
So tell me about those entrepreneurs. So they're early in their journey what are the founders usually look like and what do you usually helping them with?
Yeah. Great, great questions. So I would say most people still come to us with the notion of, oh, they could be early check, first check. You know, they're generally coming to us first for money because most of the marketplace is saying to them, put a pitch deck together, pretend like you have it all figured out and go try to convince some people to give you money so that can go try and figure it out. And so that's often how we see people.
Of course. So you're giving money, but how do you describe the work that you're doing when it's more than money or what's a good example of that sort of thing?
And then I think under that we see sometimes really technical founders. And in those cases, what, where we often need to help them is on the, Okay.
Not necessarily build first, but let's go validate. There's a real problem that people are interested in having solved that they're willing to potentially pay for. Can we do some early customer development before we even build, because let's, let's make sure we know that we're actually on the right track to building the right thing.
Uh, and so that's often where we'll, we'll partner with a technical founder and sometimes that's a good, healthy conversation. And sometimes it isn't. And we use that as somewhat of our determination of whether this is the kind of lovable, collaborative, coachable founder that we really want to work with.
So that's one class for sure. And we've had some great success. With some folks like that. Uh, we also have what I would characterize as the subject matter expert type founder who may or may not be technical, but realizes that there is a critical market problem that they deeply understand. Often they have that insight that I get really excited about that they just, they see something earlier or maybe differently than others in the market that they're in.
And they really are excited to solve it. And in some cases we've had to bring technical resources to help or build resources, to help them on the product design engineering side, just from our bench and network to really help get that off the ground. And then I would say the third is maybe a little bit more formed initial founding team.
And in those cases it's just design determining if we can be a force multiplier. For them, maybe it's additional heft in key areas. They need help on go to market or product maybe in technology or just executive kind of, and strategy support to say, Hey, you've got, and we have one of those right now that we're really excited about.
They've got a great start and we're kind of supplementing them in, in a whole bunch of areas and also helping them get this launched. And they, they, you know, were on the track of, of building something. But weren't exactly sure how they wanted to go launch and learn. And I think what we have a really good discipline and muscle around is how do you develop a rapid learning plan in the early stages?
Because I'm very adamant about, you know, trying to increase your rate of learning early on that you're really just an experiment that you're trying to validate and invalidate as quickly as possible to find where then that real opportunity. Yeah.
Yeah, anything non-intuitive or sort of special to what you're doing. They're just getting product in market, talking to users.
Yeah.
I think we kind of customize it per business. And it, you know, I would say if anything, it's just a function of, I've worked in so many different industries and sort of so many different types of business models from direct to consumer to direct a business, to things that are entirely channel driven, that we can sort of explore various options and in the early stages and say, okay, what is the best way for us to potentially go validate or invalidate?
And, you know, we have one business for example, that right now it's direct to consumer, but my partner and I would probably say in our gut, we believe that ultimately will be a B2B distribution business. But we had to go prove we couldn't really find anybody. We felt like in the B2B channel early on, that would jump in because it was so early that we said, if we go prove it direct to the market, then they're going to want this because this is a really high value for their end consumer customers.
And I think what we have a really good discipline and muscle around is how do you develop a rapid learning plan in the early stages?
Because I'm very adamant about, you know, trying to increase your rate of learning early on that you're really just an experiment that you're trying to validate and invalidate as quickly as possible to find where then that real opportunity. Yeah.
Uh, and so that's often where we'll, we'll partner with a technical founder and sometimes that's a good, healthy conversation. And sometimes it isn't. And we use that as somewhat of our determination of whether this is the kind of lovable, collaborative, coachable founder that we really want to work with.
Um, but we'll go prove that first directly, but ultimately our brand may need not need to exist. We'll see. And so I think that's, that's maybe the unique perspective is that we just, we started don't have a single path view of the way the world is or has to be.
Yeah. So a few things you said, so you said lovable a couple of times, which is adorable and lovely. Um, but here's my view of you, Carey is you say no founder, no company is too early. I think you've said you think VC's, over-index on founder experience. You're looking for someone lovable. So you're taking these people who are first-time entrepreneurs don't have that much traction and you're, you're loving them.
I don't know how else to say
Yeah. here's what I think about it is we're energized to help build things that.
need to exist in the world that are going to dent the universe in some meaningful way or change things in some really meaningful way. And obviously create a lot of value. And I think we want people that we get excited when we wake up in the morning.
Oh, we get to work alongside them today. We get to help them. You know, it doesn't mean we don't have hard conversations. It doesn't mean that we don't. Sort of have conflict and challenge each other, but I think we want people that we can be excited that they, they are lovable. And that doesn't mean they listen to us.
That doesn't mean they, I mean, it's like, I think of it. Like I, you know, I have three kids and my kids don't always, uh, listen to what I demand they do or advise that they do. And, you know, I feel like in some respects, entrepreneurs or founders are, are a little bit the same way and that they need to know that there's, uh, unconditional support.
And there's an underlying foundation of trust and, and love there. And that the end of the day, we want them to be their best self through this. at this point, it's, I'd rather optimize for enjoyable people that have that mutual respect and trust. And so I think that's, that's where we use the term lovable and people can be lovable in a whole bunch of different ways.
We all have our uniquenesses and quirks. I think we, we embrace that diversity. And how do we, you know, as long as there's a high degree of trust, I think we can, we can find ways to have that.
I like that. We're getting kind of philosophical here. all of us are lovable. I also think you're very missionary in the way you talk about this work. So tell me more why this is such a mission for you.
I, I think it's critical. just to us as humans that we can go find our place in world. And for a lot of people, they have these ideas or they perceive, Hey, this could be way better or different. And that, to me, that that's something we as a society, I mean, historically in the history of America, We were founded by entrepreneur misfits, who, who came here. And so it's, to me, it's like the culture of our country. And so I think that's where it starts for me. I believe everybody should have a chance to try to pursue that. And I think the venture world likes to pretend like that's the case. And I think it's actually been a very exclusionary, somewhat clubby
environment historically.
And if I look at where, where I am, particularly in orange county, but also in Southern California, you have incredible diversity of the elements and attributes that you would look at in the population. But you have people going to community college, or you have now an increasing number of people here who are first in their family to go to college and they don't have this network.
But they are demonstrating. They have the grit and determination to go improve their lives. And I go, those are the people that are probably our next set of entrepreneurs If you've got that spark of genius, it's really about just helping assemble the puzzle around you. And for me to expect that you have to go figure all that out on your own, I think is just dumb.
And so we feel like that. I mean, to me, that's the mission is that this should be a much more democratic, operative.
Great. And so you're writing a few hundred K initial checks.
yeah.
our range. And we kind of look at it because of the fact that we're willing to contribute our team into these companies as well. We will look at that in many cases in lieu of putting capital in. So they need, they may need a half, a million dollars of investment. And we may put in a portion of that in capital and a portion of that in our team.
We haven't done any where it's entirely just our team and we have done some, as I said earlier, where we have done just some investment only scenarios as well. Usually we're not doing that all by ourselves. Usually if we're doing that, we're either doing it alongside others or we're immediately going.
Yeah. Bringing in co-investors or we've done scenarios. I think, um, we've talked about previously where we'll even do SPVs at times alongside a investments. So our view is we're in the business of how do we help when we find that founding team that we really want to partner with? How do we bring all the capabilities we can bring to help them move it forward quickly and effectively?
Got it. And so for the SPVs, um, I do think that's an interesting topic. Um, are you sort of creating, do you have like a big following on angel list where you, you know, routinely do this or do you sort of have your LPs and people who, you know, are interested in investing and you will pull that together?
Okay, so invest in, and then I think you said you've doing some SPVs. And what do those look like for you?
in most cases they've either been, investments that we've already made, that we're doing a follow on investment into, and now bringing it to our network, or in some cases we've done them alongside an investment we're making from our fund because the company needs more money than we're able to bring out of the fund at a point.
And so we'll just do an SPV alongside that. And we have that where we'll take it to our LPs and we'll say, Hey, here's an opportunity if you really liked this one to go deeper than you're going to get exposed to just in the thought
let's talk a little bit about orange county because you're in orange county, as you said, getting democratizing access to, to, to building, to sort of realizing your vision. What does orange county have? What do you what's the view there?
that is a great question. And I, you know, I like to believe I am more involved in the, and know more people in the early and growth stage venture community in orange county than probably anybody else. Cause I've been very actively building those relationships for almost 20 years now. you know, orange county is doing great in med device and you know, on the health care side of the world, we have great companies emerging in ophthalmology and aesthetics and medical device.
And I would say those are probably the, the areas of highest. Growth and potential right now and not my area of expertise at all. on the more traditional software based tech side, I think we're still trying to find it. There is a vibrant community. We have pockets here and there, or I would even call it kind of one-offs.
and so we aren't unfortunately doing as much in orange county as we would probably ideally like, but we're very so Cal focused. And so as I look at us now, almost not quite two years old, um, we're increasingly doing more and more in LA
and we're doing a little bit in San Diego and we kind of look at it as, Hey, we're in the middle we're, we're in a good place.
Uh, I think COVID also made us more comfortable with the idea that. Being not every day together, we can still figure out how to support our companies, uh, in a hybridized see them and virtual environment. So we've, you know, we, we didn't change our footprint at all, but I think we're, we're just trying to go where the founders and the opportunities are with a focus on Southern California, because we feel like this is a region that has so much vibrance from call it Santa Barbara to San Diego.
And, you know, the, the big companies, particularly now after the COVID experience, I think we'll probably end up with very different physical footprints. If they've tried to grow here in the next decade and they may end up with multiple nodes, you know, the, the trip down the four or five and five to build out a company.
25,000 employees here or something. And so I think we feel like we can birth those anywhere in the region and then support them along the way. And so it's more important for us to all be interconnected and supporting each other to, I think, you know, really raise the region together. So that's why I love being able to build relationships with folks like you,
Yeah. Yeah, I still think of orange county as having a lot of semiconductors. Is that still true?
which is, and it's actually making a significant comeback.
Hm. And great surfing and real estate. do you find like a lot of LPs made money in real estate or is that a misconception?
Uh, there are a lot of people who have made money in real estate here. Most of them are still making money in real estate So I think the hardest thing. Is to get them to allocate any amount of capital. So, we have a few who have done well in real estate who will dabble, because it's, interesting, or maybe their kids are not doing real estate and interested in tech or something, but that's been probably the biggest challenge from my perspective is I look at it is if I have am heavily invested in real estate, in Southern California, then the best way for me to protect that investment is to invest in the job, creating entities that are going to produce the, the high wage opportunities that keep the people living in my apartments, shopping at my stores, working in my offices, et cetera.
And for some reason that has not been nearly as intuitive to others, as it seems to be.
And are you from orange county?
I'm from Indiana.
okay. Well, good transition. I think you had, you grew up your family had a family business.
Yes. So I grew up, yeah. I mean, I can give you a little bit of
yeah. Give me the background.
So I'm from a small town in the middle of Indiana. and when I showed up in the world, uh, I was born into a family that had a family business that was already a hundred years old. When I showed up,
What is it
do?
we were the local retail lumberyard hardware store,
Oh,
and it started by two brothers in the late 1870s.
So you can figure out my age and, you know, eventually my great grandfather married the only daughter and took it over. And then, you know, my dad and my uncle were. Principally running it when, when I showed up. And so I grew up in this business and it was a really interesting way to learn about business and learn about community and, family connectivity into that.
And, you know, people who were involved or weren't involved in a lot of those dynamics. And I think between the location of it, I learned a tremendous amount, but I think between the location of it, uh, in the small town and the business itself, that just seemed to be getting increasingly difficult. I determined it just, wasn't a great fit for my life plan
and
Can I just ask about your childhood and just the family business a little bit, which is, did you, did you feel like your parents did a good job of like teaching you business through the family business or whether you I'm just curious, like, uh, I'm curious about family businesses and whether you felt like it was things your parents did, right.
Things they could've done better.
So I think, I mean, I was able to, I started working when I was probably 10 and, you know, it was, I was just, uh, always been a very curious, you know, if you're asking my mother, I was curious, precocious and uh, just always interested in things. And so I wanted to know what my dad was doing. So I was like, I'm going to come down the store.
Can you? And they just kept me busy, gave me things to do, and I just would learn something and do something. Okay.
Is there something else? Uh, so I think, yeah, I learned it more by experiencing it and doing it than being taught if you will. I mean, I was taught through no, don't do it that way, do it this way, but it wasn't there, there was not a true classroom, but I, I did learn a fair amount, but I actually, in retrospect, wish it had been a little bit more exciting.
Probably because I probably would have gotten to some other conclusions faster, but as life went on, I would apply a lot of the experiences or situations to, well, how would, how would my dad have handled that? Or how would my grandfather handled? That was always a filter that I would try to use. And so I, I did have enough experience there that that really helped.
And so often I've, I've said, I feel like most of what I have needed to learn about business, about people, whether that's employees or customers, partners, and even community, I feel like I learned growing up in that business. And so it's served me as sort of a core foundation incredibly well. Uh, I just didn't, you know, looking back, I just didn't love the actual business and I would have no doubt.
And I talked to my dad I'd liked about that. I would no doubt tried to change it or certainly have changed my role in it, not needing to do the same thing every day. Uh, and that probably would have caused a lot of friction. So we, uh, I think we have a much better relationship, uh, as a family, as a result of
Hm. Yeah. I'm always just fascinated how parents can expose their children to, to business. Um,
well, it's been fun. I mean, now, you know, the beauty of now with having three kids, uh, I just sent my kids a text yesterday with a link to the app store to download one of our newest company's apps. I said, tell me what you guys think, because I actually found that their feedback. On things like that is incredibly valuable and it is me trying to attempt to get them somewhat involved because I, I totally agree with how you're thinking about it, that I think there are incredible life lessons to teach them through that.
Yeah. Um, but, okay, so you left, uh, you left the lumberyard hardware store and my summary was that you've been a serial C-level executive at a number of startups. Uh, I'd love to hear about some of the, the sort of formative experiences for you.
Sure. So, I mean, formative would be, you know, decide not to do that. I actually, I started my career at Proctor and gamble and I, you know, got into this company that a lot of people are really excited to go work for. And I quickly realized I wasn't excited. And I was on this fast track management development program and realize I didn't want any of the jobs that were in that chain.
And so within the organization, I explored a little bit to see if I could find something that was interesting. And I did a couple sort of intrepreneurial things in my early days there until they decided I needed to really do something, uh, important. And I said, okay, I probably need to go now. And so one of the projects they did there in both software, and I said, this is where I need to be.
And so when I left, I talked my way into a enterprise software company and I took a sales job and I was probably at least 10 years younger than anybody else. And this was before the days of the SDR model and. Literally, you know, sharing a bag, calling on big companies, trying to figure out how to sell big ticket software.
And I did fairly well. And I think from a formative experience standpoint, I realized, okay, I can, I can do these things. And that it wasn't just about having a bunch of experience. It was if you were really good at adapting and learning and paying attention that, I wasn't the best salesperson, but I was often the best friend of the product team because I was bringing back and understanding how they wanted feedback more than salespeople, who often are saying it needs to do this and he's to do that or, or whatever that relationship often could be.
And so I started to think about, okay, well, why did the best salesperson just get promoted to sales manager? Is that. The right decision, if they're really good at that, why aren't they in that role? They're not showing that they have great management capabilities. And so, you know, was involved in a couple enterprise software companies and then the.com crash hit after that.
It wasn't immediate. But after that shortly thereafter, the company I was in was starting to struggle. And I said, okay, this is going to probably take a little while. And so I used that as my excuse to leave Chicago. And that's how I got to LA. And so I came out here almost 20 years ago during, you know, in the aftermath of that to just wait it out.
And I said, oh, grad school is my excuse to move out here. And drag my wife from Chicago, let's go have an adventure. And a weekend, we looked at each other and said, I like it here. Maybe let's stay here a while. And we've been here ever since. And so I think that first was kind of the, oh, okay. I can do this.
And you know, the second one was once I got here, I decided, well, I need to build a network. I've got a bunch of classmates, but what's going on here. And so I went out into the, uh, into the market in LA and say, okay, are there interesting software companies here in LA? And you know that a couple of decades ago there weren't many.
And I happened to meet, a founder of one who was based down in orange county, where at that point there were more software companies, I think, and even in orange county than there were in LA probably 20 years ago. And he was a technical founder. He had a product and one customer, and he was looking for uh, you.
know, air quotes, VP of sales.
And we met and found that we had really good chemistry. And I said, I think I can get you more customers. I think that's what you need Right.
now. And I'm a. Business school student I'll do it for equity because I've figured out how to live. And I think this could be really interesting. And so that was, uh, another really formative experience because I just said, I'm going to bet on myself and what I think he's got here.
And we grew the company really quickly and actually exited it really quickly. And we sold it to a venture back company that I had met, who was a great strategic partner, because I, I got to a point where I said, well, I just don't want to keep cold calling and selling every day.
How do I start to scale this? And I found, uh, a partner that had a bunch of salespeople that we were a nice fit with and may decided they liked it even more than a partner. They wanted to buy it. And that's, that's where I often will use the term. You know, business development can often be a great form of corporate development and the partnership turned into a merger.
And then Microsoft bought that combined company about a year after. That. And so, you know, really the kind of transition experiences for me that led me to say, okay, this is where I need to be. I just need to go find the opportunities that fit my personality and where I can contribute. And what I started to really optimize for in some respects were what I would call 50% jobs where, you know, I knew 50%, like in the case of of message.
Right. I kinda knew I, you know, I knew I was going to go about selling it. I'd sold SAS previously. I kind of had a sense, but I had to go run Google ad words, campaigns, and figure out how to get people onto our website because, um, I, I didn't want to just pick up the phone and cold call every day and want people to come to us.
And so that was a part I got to really learn and then think, about the strategic partnerships. And so then each kind of incremental role from there was sort of 50% I had a good sense of and 50% was something I was going to have to go figure out and learn. And that really excited me and got me energized to work all the hours that you often need to, to contribute into a, an early stage.
I think, um, I think that was a great big lesson, which is the, I can do this lesson. Um, I mean, I think that's actually, when people say you need to go iterate, it's just believing that you can go run the Google ad campaign and talk to users and all of those things. Um, what about app startups? Any thing else really stand out once you, you know, now we've gotten you to, to this startup you C-level startup role, any other big, you know, maybe, uh, I don't want to say misses, maybe like, you know, hard lessons learned.
and any other big lessons learned from your startup experiences?
Well, there was one, that I started that now goes on it's 17 years ago. I guess we started and my partners were in Seattle. I was in orange county at that point. And so this was after we had sold the company and we had a great idea. Amazing idea. We were, I mean, you know, it's almost sad for me to admit it.
We were building marketing automation before marketing automation as a term and really existed. And we were doing dynamic constructed email on a one-to-one basis. And you know, the, the challenge, wasn't the idea. We actually got some customers, we got some revenue, um, but my partner's not. All did it initially as a moonlighting exercise and we were remote and we were using Skype and the collaboration tools at the time.
But what we were talking about iterating, we just weren't moving and iterating and learning fast enough because when we started, none of us was full-time on it. We all had different tensions and different abilities to, to contribute. We had the right mix of skill sets, but we just were never able to get on the same page.
And so I'd move ahead with some customers and have a sense of what I thought we could deliver to them in the timeline. And then we'd extended and then I'd be frustrated and the customers would be frustrated because they couldn't get it on time. And then that strained our partnership. And so really the hard lesson there, because we ultimately walked away from the opportunity.
And I think there were a couple of key lessons for me. One, one. It all things being equal. If you can try to get equal commitment in the early stages from the founders, and ideally you'd be co-located physically together because you can do, you know, you can move no faster than your slowest, contributor at that point.
And if you're all there together, you can sort of make sure everyone's at least close, closely following each other. And so I've tried since then for anything really early to make sure people are at least co located, unless there was already a strong operating history in our relationships and existence.
And so that was one. And then I think the other is this idea of, there are times when you're on the right track that you just have to survive long enough until the market arrives because it wasn't too long after, uh, That some of these companies started to emerge and that was frustrating. And, you know, when I built, when I finally built another marketing automation software company, many years later, um, I had a, a head start because I had done it once and I knew where the value was, but, um, we were by no means the, you know, early entrant to the market at that point.
And so I think, you know, surviving is, is a key lesson when you know, you're you're onto something.
Yeah. One of the podcast episodes I did was with my partner, Gil Elbaz. And he said like, look, just if startups fail, but the ones who can make it 10 years, they're less likely to fail if the person's like just going to do it 10 years.
that's right.
okay. Anything else? I do want to talk about podcasting a tiny bit, cause I want to pick your brain.
Should we move there? Your podcast is the operate podcast.
Okay.
And you know, I'm just so curious. How long have you been doing it now?
So I've been doing the podcast now for two years.
me too. Me too. Um, do you think you've changed? Like has your communication, do you notice that, like you ask questions differently or have you changed as an interviewer?
That's a great question. I'm sure I have. If I go back, I haven't gone back and read, listened to my early episodes, but that's, this is a good question to catalyze me to go do that. I'm sure that I have, I feel like I have been a podcast interviewer for a long time, because when I started the podcast, what I told a bunch of my friends who were many of my early guests, and, you know, at one point I, stood up in front of a big group and said, I'm going to start a podcast.
And all of you are going to be my guests to start. A lot of them I've been having coffee or lunch meetings with, for years. And in a lot of cases I was interviewing them and that was the conversation. And the goal was to make it much more conversational. So I probably participate in my podcast more than some people do.
And that it's maybe a little bit more conversational than just me question, question questions,
I think a lot of the best interviewers make it at least seem very conversation.
yeah, probably. And I, because I've worked in so many different spaces and I read and very divergent things, I, I am at least able to have a short conversation on most topics and I'm fascinated by so many things. And so I think that helps me in a, in a podcast because I can, oh, I just read about something the other day on this topic.
And that helps inform me to at least feel like I can participate in the conversation and it's not, uh, just a completely, completely uninformed, uh, set of questions.
how about any, uh, have there been any moments or any interviews where that have really stood out for you where you've know? Oh, that was so good. So interesting. I feel like I listened harder on my own podcast.
Yes. I mean, the ones that are probably been the most meaningful for me is when they're just this incredible emotional connection. Um, you know, a guy that's become a really good friend. He broke down because of just how passionate and he felt about what he was saying. At that point in time, and that that was super memorable or, you know, another friend of mine who just is so vulnerable and transparent in how she communicates and that really drew me in.
I think those are the things that have, have influenced me to just think about my communication style more recently. And, and I think those are moments that I, I I'm learning something here. So, um, you know, pay attention to that. So those, those are the things that I think are really fun about it. And, um, I try to always tell my guests, I'm not trying to get a scoop or get you to say something that you know is an aha or anything.
I really just want to share what otherwise might just be the two of us talking with other people who may or may not be interested, but I know I am and that's enough.
Yeah. Um, so we've been, you did say that this is what I'm fine, which is, I do think my communication has changed from having recorded all of these. And so you said you heard this woman who was more vulnerable in her speech, like, has that changed how you view your own speech
for sure.
and made you what, like more, speak more with more emotion, more.
At times I think it just, it, it showed me how powerful that can be. I don't, I don't necessarily use it all the time, but I think if it's something you say, okay, if I need that, that, that, that is something I should really think about. I mean, I I'm, I feel fortunate in that. I think I've been very comfortable being who I am for a long time.
And that I feel like was a gift from my parents and. So, you know, it's worked for the most part. I'm sure there are times that, that people don't love who I am and that's okay. You can't ever please everyone. But, um, I feel like people know who I am when they get to know me and like this isn't a character.
I mean, we're all characters, but it's a consistent one.
Do you have sort of unpopular views or things that you're like, well, it doesn't matter to me because I'm comfortable with that, that you don't have to like me for my unpopular views.
Uh, yeah. I mean, I think most of mine are probably about, sort of the, how we keep score of, you know, in, in looking at people or achievement or, what success actually means. And, you know, we're, we're definitely, and I'd say, you know, particularly in orange county, you, you have. Material wealth and, things that at times are, are challenging for me to, to deal with because, you know, I think if we don't have a, a society where people have at least a sense of equal opportunity, I mean, you still have, I don't know, 150 million people in the world that wants to migrate to the U S to pursue the American dream.
So it's not completely broken, but I think those of us who are here now, it's much harder to achieve today than it was 50 years ago.
And so, I, those are probably the views that I, I sort of try to, uh, figure out like how to, I think by creating more entrepreneurs, we're probably creating more people with the potential to achieve that.
And I think those are where, um, I, you know, at times I'm very comfortable with my view on it, which I don't think is, is, uh, unfortunately really affiliated with any. Existing group in any clear way, but I think there are a lot of other people that sort of have and wrestle with some of the same challenges as far as how they think about, you know, how do you direct your talents and energy to have the biggest positive impact?
And so, you know, the advantage of measuring it on things like money and wealth is that it's very quantifiable. Um, and so, and I don't buy into it, but I worry. I mean, well, I think, you know, how do you, how do you quantify that? Or how does it, how do you think about something like measuring your success in, like, I, I don't know if is enabling entrepreneurship, like what do you, how do you think about that for you?
it's actually something what I've chosen to do is just not measure. And you?
know what, the way that I rationalize it, many, as I say, okay, you know, there aren't many people that come from a family business that lasted 146 years. And the only reason that it doesn't exist anymore is because my dad wanted to retire but it was a very sustainable business.
And there aren't many in the history of our country that have persisted that long and part of why it worked so well, if you really start to look back is at no point, were they trying to profit maximize on a given month or quarter or year? And it was about how do you. Create a sustainability of its, uh, providing, uh, a fair income to the families involved.
It's supporting the people that are showing up every day to support the customers and work in the business and the community at large, that is benefiting from it being there. And then also providing resources to the safety net and social aspects of the, of the community as well. I mean, my grandfather and my father started a program where they build a home every year And they've trained thousands of people in relevant skills through that. And that's just a part to me.
Those are high impact. And that I don't think can be achieved through a single number. And I think where we as a society in many respects have lost our way is by trying to boil things down to a single number, as opposed to accepting that the world is way more complex and complicated than that. And we have to be okay with maybe more of a triangulation when it comes to how we measure.
And that's what gives me a ton of excitement about this notion of impact or ESG investing in that people are accepting. Hey, we need to think about these things in a, in a little bit different way than just a single number, like IRR MOIC or something like that. And so I, I, I'm an abundance thinker as I think, you know, and so my view is I think we all can do it.
So I think that's like we look at it as like
I'm going to compete. as A portfolio, not on,
you know,
do I have the biggest winner? I'm going to look at it as, can we get eight out of 10 or 9 out of 10 of ours to success? Because I actually would rather have more people having some modicum of success,
thn
Hmm. Hmm.
than one out of 10 wildly succeed and everybody else fail
That's a good perspective. I like
that.
sorta how I think about like, I'm going to compete by trying to help as many of them be successful as I can.
Let me think about this. I mean, like, these are the things that just blow my mind are you've got these like foundations and pensions and endowments that are literally trying to invest capital on things like a single number. And you go like, that's not your, you're not even being held accountable in the right.
way. Right. I mean, you take, you know I find it horrid. I'll give you an example of that. The orange county pension funds, aren't investing a single dollar explicitly into orange county.
Right. I know I knew where you were going.
Or LA county for that matter, this doesn't make sense. And yet the system is totally not aligned, even close. It's totally misaligned.
And my view isn't it can be, I don't know. that it can be perfect, but you go, come on
Hopefully you can work to change that. And we're going to run out of time because I have more questions, but, maybe the flip side of that,Carey , what keeps you up at night?
How I feel like, you know, the, probably the, at times the things that keep me up at night are, am I being too idealistic? should I, take the faster, easier path at times?
Hmm.
you know, am I crazy? and so that's one side and then I think the other is, is I often really trying to evaluate am I best utilizing the gifts and talents that I have in the world?
And so that's something I question from time to time. I don't these days, I feel like actually these last two years are probably the most activated I've ever been.
And so I feel like I have. Reached a place where I am probably as close to fully utilized and deployed as I can be. Um, but those are the things that have kept me up at night.
Um, you know, thankfully I've really helped the kids and family and those things give me a great foundation to work from.
📍 that's great. Curious. I love, I find it talking to you very inspiring. Um, and I'm glad that you are doing the work that you're doing. And I look forward to crossing paths more in the Southern California ecosystem.
We absolutely will.
Great,
Thank you for having me.
great. Thanks for coming on. All right. That's an hour. And I tell my editor, I, so we edit pretty heavily.
That's there's a ton of content. My editor is not going to like it. Cause I taped for too long and then he's grumpy. Cause I tell him to make it, uh, you know, I try to make them 25, sometimes 20 minute episodes. There's no chance here, but, um, there's a lot there. I really like.
I have a tendency to go at times.
Yeah. I mean, I really liked the whole, the whole theme we were just on it's so, I mean, it comes up again and again, whether you're talking about lovable founders, it helps me understand you better.
Actually, I like it
Well, I appreciate that. Let me think about this. I mean, like, these are the things that just blow my mind are you've got these like foundations and pensions and endowments that are literally trying to invest capital on things like a single number. And you go like, that's not your, you're not even being held accountable in the right.
way. Right. I mean, you take, you know I find it horrid. I'll give you an example of that. The orange county pension funds, aren't investing a single dollar explicitly into orange county.
Right. I know I knew where you were going.
Or LA county for that matter, this doesn't make sense. And yet the system is totally not aligned, even close. It's totally misaligned.
And my view isn't it can be, I don't know. that it can be perfect, but you go, come on there. There has to be a better way here. Um, and I think those are the things that I think, you know, at times really challenging.
Hopefully you can work to change that. Um, here's mine. Let me give you, I didn't want to say on the pilots, but like I'm so competitive. Like I was just born competitive, I think. And yet I'm not motivated by money. Like I not, they don't, that's not my, it doesn't, it's not what I set out to do. Um, and yet some of the, like the, the sort of more motivating work is very hard to.
Quantify. I can't compete on it in a sense like, and I just, I don't like saying that because I feel sort of crass, but that's what I was trying to ask you is how do I reconcile wanting to compete on something? Cause I find competition so motivating.
And I, I mean, I love to compete. I mean, I'm, I'm, uh, I know you you'd put in there about sports. Like I was probably one of the hot, which probably hard to believe because I just needed to mature. That was one of like the hottest head competitors. I would yell and throw stuff when I was playing tennis. And I, you know, I would get into fights with people.
I shouldn't get into fights with when I played basketball and, you know, just really, cause I just wanted to win and I always want to win that's who I am, but I just feel like, um, you know, you can do in a lot of way, different ways I guess is how I kind of what I've gotten to. And um, you know, everybody should be able to win at some level, I guess is it's it's about like getting them into the place where they can best have a chance to win. So I think that's like we look at it as like
I'm going to compete. as A portfolio, not on,
you know,
do I have the biggest winner? I'm going to look at it as, can we get eight out of 10 or 9 out of 10 of ours to success? Because I actually would rather have more people having some modicum of success,
thn
Hmm. Hmm.
than one out of 10 wildly succeed and everybody else fail
That's a good perspective. I like
that.
sorta how I think about like, I'm going to compete by trying to help as many of them be successful as I can.
That's good. I might ask my editor to put that back in. I liked that a lot. Okay. Well this was great. My editor will yell at me. It'll be great.
Um,
Great to see you.
great to see you. I'm sure. We'll talk soon.
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