Please enjoy this transcript of my conversation with Andrew Dumont, Founder of Curious Capital, former CMO of Bitly, and one of Forbes’ 30 Innovators Under 30 in Marketing. In this episode, Andrew and Daniel discuss the pros and cons of venture capital, why some startups make it while others fail, and how investors can best serve founders. Transcripts for other episodes can be found here.
“When you’re first starting a fund, you're going to spend your first five years, realistically, actively raising money from LPs—and that is your primary role. It is not interfacing with founders and helping entrepreneurs; that's a small piece. I think it's important that people realize: if you just want to work with entrepreneurs all day, join an existing fund.” – Andrew Dumont
Andrew Dumont (@andrewdumont) is the Founder of Curious Capital and CEO in Residence at Tiny Capital. He was previously the CMO of Bitly and an Entrepreneur in Residence at Betaworks. He’s spent his career building and growing companies like Moz, Seesmic (acquired by Hootsuite), Stride (acquired by Copper), and Tatango. He’s also an advisor at Techstars and Startup Weekend, and he writes for Inc. Magazine.
Andrew was named one of Forbes’ 30 Innovators Under 30 in Marketing and was appointed an entrepreneurial delegate by the United Nations. In this episode, Andrew and Daniel discuss scaling an open source framework, the business of job
Daniel Scrivner (00:00):
Andrew, I'm so excited we can make this happen. Thank you so much for making time, and coming on Outliers.
Andrew Dumont (00:05):
You bet, glad to be here.
Daniel Scrivner (00:07):
The theme that we came up for today is Adventures in Business and Investing, which will make a lot of sense once we get further along in the episode, because there's a lot to cover. But I thought, a cool place to start, I was doing research for this interview, was reading stuff you've written, stuff that's written about you, and was really struck by your About page, on your website. You list off a bunch of things that are different, and your experience from a traditional entrepreneurs, and then you have this paragraph that just says, "But, in spite of these shortcomings, I've been able to make my way through the world of technology and entrepreneurship on a combination of moderate intelligence..." Which I love, "... and pure grit. At a fundamental level, I guess, that's what this site is all about. It's for the underdogs, the ones that haven't checked all the boxes, but have aspirations to truly be great." Can you share a little bit about just your background, and your upbringing, and how that led to your interest in entrepreneurship and investing?
Andrew Dumont (00:56):
Yeah, and it was by accident, really. I first got started in technology, I think, I was 17 or 18, and I had just graduated high school, and I went to a state college, because it was most affordable, and the best option for me to go get advanced degree. When I was in school, I just had this desire to just start putting it in practice and start doing, and it always felt like school was a waste of time that prevented me from doing that. The first entry into technology actually came just as I graduated high school, and there was an article in the local newspaper. I grew up in Bellingham, Washington, almost on the Canadian border.
Daniel Scrivner (01:39):
That maybe helps explain that.
Andrew Dumont (01:40):
Yeah, so I say, sorry a lot, and that's why. That's how it started, and I reached out to the founder, and I said, "Hey, I have no experience. I had no idea what I'm doing, but I'm really hungry, and I want to try, and learn, and help wherever I can." At the time he was his parent's basement, and they were building this company called Tatango, they had just raised angel money. That's what started it, and did everything, and anything that was needed, and really wasn't specialized in anything other than just doing the stuff that needed to get done. That was my first experience, and it was after that, that I started realizing what was my specialty, what was I good at? What did I enjoy doing? And then, my career went from that moment, but that's really where my entry into technology started. I imagine a lot of people that work in tech, it's similar. They fall backwards into it, unless they are bred to do that, or have that traditional upbringing, which I did not.
Daniel Scrivner (02:40):
One of the things that you touched on there is just being in school, learning about business, but learning it in abstract, and wanting to put in those reps, and I guess, the sense there is, I'm learning something, but maybe this isn't the best way to learn, or maybe I'm not learning anything that's actually useful. To fast forward a little bit, and we'll talk about all this stuff that you've done, but did that turn out to be true? Were you glad that you had that eagerness to start putting in the work and learning?
Andrew Dumont (03:06):
Absolutely. Yeah, that's fundamentally, you'll see, my career experience looks disparate, and not planned, and it's not. It really is led by curiosity, and desire to learn, and I think in the early stages of your career, that's the most important thing that you can do, so that's always been the priority for me, and demystifying, and getting this firsthand, real world experience in everything that I do, and in a lot of different categories of work has been critical for me, or the most important thing for me. That's the big driver, and that's been the main thing I've been prioritizing.
Daniel Scrivner (03:44):
Do you advise people that want to go into business, or start their own business, or scale a business to go to school, or do you encourage people to take that direct route?
Andrew Dumont (03:52):
I do, and my experience was interesting, because I was in school when I started working at that first company, and then I actually dropped out for a period, for about a year, as we raised more money, and it got more serious, and it demanded more for me. And then, I actually went back to school, and finished my degree, and I started working for a company in San Francisco called Seesmic, which got bought by HootSuite, and for me, nobody in my family had got a four year degree. For me, it was really important to just check that box and have that understanding, but for me it was worth it. I think it was really nice to match my real world experience with my proper formal education, and have those going simultaneously, was super valuable for me.
Andrew Dumont (04:38):
Actually, over time, even though it's been devalued, I would say in our world, I value education a lot, and actually would love to go back at some point in my life, and go get it master's degree, or the next step. For me, I've actually valued it more over time, and I think we devalue it in our world more than we should really.
Daniel Scrivner (04:56):
To fast forward a little bit, it sounds like right out of school, you start jumping in and getting some of these reps at some of these smaller companies, and you eventually go on to work at Moz, and become the CEO of Bitly. Walk us through a little bit of your introduction to that venture capital world, and some of the things you learned along the way there?
Andrew Dumont (05:16):
CMO at Bitly, I just want to-
Daniel Scrivner (05:18):
Andrew Dumont (05:18):
... correct that, so Mark doesn't get mad at me. My real venture experience started with Seesmic, and Seesmic make at the time had raised a lot of money. It was right at that early social platform days, and that was really my first taste of what does venture capital do to a business, and how much does that accelerate things? And then went on to Moz, where we had that same experience, where we raised quite a bit of money in that scenario as well. And then, I went to Betaworks, which was the next experience of that, which was more of a capital allocator, and studio that led those investments, and was at the very early stage of that. Then I ended up at Bitly, which was, I think in total, they raised over 40-ish million in venture.
Andrew Dumont (06:04):
But at the time when I joined, we weren't running on venture money, we were running on revenue. I've had a lot of experiences between venture, no revenue, no profit, to today at Bitly, and being revenue driven, and I have to say, they seem a lot more healthy when they're driven on revenue, and they're driven on profit, and it feels a lot more sustainable, and we can speak about the tiny stuff, and how I ended up there, but it's been something that has been pretty interesting just to analyze it from an operating standpoint, just how different they really are.
Daniel Scrivner (06:38):
Yeah, I love that you said that, because that's something I think most people don't say. I've had that same experience, and to connect one other dot, you and I both are venture capital investors, so we ultimately end up making investments in companies. It's not that we think it's totally useless, but I think we've also had that flip perspective and that realization of, at the end of the day a real business survives and thrives on revenue, and obviously, the venture capital distorts that for a little bit. What is your take on when someone should lean into venture capital, and just some of the pros and cons there?
Andrew Dumont (07:09):
To your point, venture capital is not bad necessarily, but I don't think it applies to every startup, and I think it's the narrative within our space, that venture dollars equals legitimacy and success, and potential, and all that. In some cases that's true, but I think in most cases, venture capital is not necessary, and it creates this really challenging dynamic as a founder, and as someone working in those companies where interests are aligned until they are not, so if that company stops growing as quickly as it needs to, it puts the founder and the employees in a challenging situation. I think it's a valuable asset, but I think the time when people should be raising venture is if they really have a massive idea that they cannot bootstrap, that requires them to have some accelerant to go tackle that problem, which is a significant problem, and a very complicated problem.
Andrew Dumont (08:07):
As an investor, I've talked to probably almost a thousand companies now over the course of three or four years of investing, and most of those companies, they should not be looking for venture capital, because there's an easy path, or there's a path to bootstrapping it, and validating the concept before they go raise the money. The problem, the fundamental problem is I think that people look at, I want to start a company, step one, step two, go raise money, and it's not that. It shouldn't be that, and that's my main gripe with it. I wish it was more, I want to start a company. How can I go about validating that concept? How far can I get it? And then once I feel like I've vetted it, and I've got it to that point where I can turn on the gas a little, then I should go pursue venture, or I really have a significant idea that I want to tackle.
Andrew Dumont (08:55):
It's not a bad thing, but it's really this sexy thing in our world, and it just shouldn't be, really. It really shouldn't be, and I would love to talk about the investor dynamics as well, which I think we'll get to just in terms of how much the investors need the startups, and it's really positioned as the other way around.
Daniel Scrivner (09:13):
No, that's such a great point. It is absolutely flipped. It's interesting there, just a couple of things that were bubbling up, as you were saying that. There's this concept from good to great, and Jim Collins of firing bullets, and then firing torpedoes, which sounds very similar to what you're advocating there, which is try to see as far as you can get on your own, try to validate it in a small, cheap, affordable way, and then once you're sure you have something you can lean into venture capital to really put accelerant there. But don't necessarily do it otherwise, unless you're truly looking to launch a capital intensive business, which in that case, you're going to need capital. If you're launching rockets, or building something physical.
Andrew Dumont (09:50):
Yeah, and I'll give you one example of that. I invested in a company called Blokable, that's doing modular housing for affordable government housing, and that's a problem, unfortunately, that is just capital intensive, and it's going to take a lot to get that. You can't really bootstrap your way there. Whereas, there's other things where it's, software as a service business that I can spin up using no-code, or low-code type tools, test it, validate it, then go raise money for it. There's different ideas that require different sources of capital, and I think we've trained entrepreneurs to raise for any idea if they want to be a real startup, and I think that's where it's flawed.
Daniel Scrivner (10:29):
I want us to talk about one more thing related to venture capital, because I think you might have some interesting perspectives here. One thing that's always struck me is for companies that raise, again, if you fast forward, a company ultimately needs to become profitable, they need to focus on bottom line metrics, but what typically happens is, companies get venture capital, they're only focused on top line metrics, so they're focused on things like just total number of daily users or total number of accounts, and to do that, they're not focusing on monetization at all, which means their value proposition is effectively, we're giving everything away for free, but at some point that's going to have to stop. It's always struck me that, it feels like a crazy way to whipsaw around a customer base to start off free, and then ultimately, eventually, need to charge. Any thoughts or perspectives there on just flipping that switch at some point?
Andrew Dumont (11:15):
Less on flipping the switch, but I think it speaks to the longer term piece of what happens to a venture backed company, and if you look at where they end up, the majority of them either die, because they aren't able to reach the scale that they need to, or they get acquired and then die, because they get shut off by the acquirer. And then in some cases, a sustainable business emerges, or they reach some scale where they can go public, and be an independent revenue producing company that reaches that scale where that exists. But the problem is that 80, 90% of those fall into the first two categories where they die, either by not reaching scale, or die through acquisition, which is important to understand about venture, is that, that's the goal. The goal of venture capital, in most cases, aside from the best outcome, where they go public, is to fund the company until they get acquired, and then they get acquired for some multiple on your initial investment.
Andrew Dumont (12:17):
That's by design, and I've been a part of three acquisitions now, and in two of those cases, those companies die, and they go away, and as an operator, or an entrepreneur, you don't want your thing to die. I just think it's important to note that the incentive structure of venture capital is to have these businesses acquired in most cases, and in some cases have them go public where they become their own large company, and that happens, and that's great, but that is not the most common outcome, of course.
Daniel Scrivner (12:48):
We're going to get to this in a little bit, but I guess just as a little bit of a sneak peek, I know that you've done a lot of work with Andrew Wilkinson, Chris Barling at Tiny and he's a super vocal advocate of not taking venture capital, and just how messed up that is. Is a real business just a bootstrap business? Are venture capital businesses bad or good? Do you have a point of view?
Andrew Dumont (13:11):
One's not good, and one's not bad. I know Andrew well enough, and his thoughts here, and we've had a lot of conversations about this. It's more on the business of venture capital that I think is the problem. The incentive structure of venture capital investors, which is to raise a large amount of money, get management fees on that money that they've raised, and then keep doing it, and keep doing it, and get a lot of on-paper returns to then go be able to raise that next fund. That's the business of venture capital, and that's the part that I don't like as much, and I think Andrew doesn't like as much, is what that creates, and what dynamic that creates in our ecosystem.
Andrew Dumont (13:50):
I think the funniest thing about this, is that, the most capital efficient businesses are tech startups. However, tech startups are the ones that go raise the most money, and there's success in examples where that's proved out to work as an investor, but these are capital efficient businesses. They should not be the ones that are raising all that money in a lot of cases, so it's interesting. I just don't know how good it is for the ecosystem, honestly, and especially being in the investor role now, and having that experience, it's even more clear that that's the case.
Daniel Scrivner (14:25):
I love that you made that point, and we'll come back to that in just a bit when we talk more about investing. One of the things I wanted to talk about just in terms of your experiences, your time as an entrepreneur, and residence at Betaworks, if you could talk a little bit about just your path to that role, what that role looks like in actuality, and anything you learned while you were there that's shaped what you've done since.
Andrew Dumont (14:45):
Yeah, and it actually goes back to that working in startups for so long, you look at venture capital, and you look at the people that are allocating the dollars, you look, and you're like, "Man, that would be amazing." Instead of just one company that I'm working on for this period of time, I get exposure to dozens, and you want to understand it too, you want to see the world from their position. For me, that was the main driver for going to Betaworks, and I learned so much from John and everybody at Betaworks, and they just have this great culture there. For me, at that time, there was a core team of about 10 people that worked at Betaworks, and Betaworks for those that don't know, it was the first startup studio, and now there's quite a few of these out there, but their whole philosophy was, "Hey, can we take intelligent people, and talented engineers, and capital, and can we start creating companies that become interesting."
Andrew Dumont (15:42):
They've had success with that. Bitly was one of those companies, which is how I ended up there. Giphy was one of those which recently got bought by Facebook. At the time, it was Giphy, Poncho, Digg, Dots. You had all these awesome companies in all these different categories, and me in that role, I got to jump from company to company. I really helped with go-to-market and customer acquisition in the early stages of those companies, which was a great experience for me. That was my experience at Betaworks, which then led me to go be CMO at Bitly, and I actually ended up there, because I wanted larger scale. There's different phases of startups. There's zero to one, which is a really on product development, and early customer acquisition, and then there's scaling, where you go from, hey, we have product market fit in some capacity, now let's turn it into a significant business. I really wanted more of that experience on that ladder, and of that spectrum.
Daniel Scrivner (16:43):
With all of the companies you worked with there, and just the difference in the model, is there one lesson that you took away from that experience that continues to bubble up in your mind? Or, is there-
Andrew Dumont (16:53):
Yeah, well, certainly as an investor, I'll use a Giphy example, because I think it's just such a good example of how hard, but how easy venture capital investing is. I know that sounds funny, but when Giphy was first starting, it seemed pretty dumb, honestly. Alex is a friend, and they went on to be very successful, but at the time, it was a search engine for GIFs. They just took this format that wasn't that exciting at the time, and they provided a simple search engine for it. At the time being in Betaworks, I was like, "Oh, that's cool." But like, "That's not a business, that can't really turn into anything significant for me." Somebody who didn't look at it in the right frame, whereas John saw the potential, saw the opportunity there. Alex saw the potential, saw the opportunity. I did not.
Andrew Dumont (17:40):
I think about that a lot, because at least in the world of venture, and picking opportunities, they don't look very good necessarily that early on, and it's not obvious at all until it's really obvious, and oftentimes, that comes much later down the line. I think about that one a lot, and that experience a lot, where it seemed dumb for a really long time, and then it was very obvious. That's why when you do angel investing, or early stage investing, it's so much about the person, which in that case, it was Alex and the team around him, and the early traction, concept, and opportunity with where they wanted to go with it. I think about that a lot, and I've had a lot of experience with that investing independently now, where I reference that example all the time in my mind, because it's never metrics, it's never obvious, it's never that when you're doing angel and pre-seed investing. I think about that a lot.
Daniel Scrivner (18:41):
Yeah, I love that example. One for me though, it's a little bit similar is Notion. I invested in Notion pretty early on, and at the time I just thought, this is really cool. I think it's really interesting what they're doing. Do I think it's going to be worth over a billion dollars? Absolutely not, and I think as a venture capital investor you have those experiences, and I've continued to ask myself, I think anyone that does venture just has an interesting, differentiated perspective on investing in general, and just draw a little bit of a parallel, and this is going off on a little bit of a tangent. I think there's a lot of parallels right now between venture capital, and investing in public markets where you have, whether it's specs, or whether it's the IPO's that are going on. I think traditional public market investors are looking at those companies thinking they're jokes, like Giphy back in the day, because it's still pre-revenue, or small.
Daniel Scrivner (19:27):
I think, from being a venture capital investor, I don't really know what the skill is, whether it's seeing around corners, or just seeing the potential, or betting on the momentum. Do you have any perspective there, answer there on what is it that you're really trying to find? Is it momentum? Is it the vision? Is it [crosstalk 00:19:44].
Andrew Dumont (19:43):
Yeah, and this is where I've fell out of love with venture investing, because I think we do a really good job in our world of putting this feeling of like, "Oh man, these people, these investors that find these companies, they must just really know what they're doing." And, it's just not, and you know that obviously, and I think anyone that does any level of early stage technology investing, unfortunately, it's reps. It's doing it a bunch, and failing, and seeing these patterns that emerge as you go through it as an operator, I think, and it's reps in the number of checks that you write unfortunately. There's a reason why Ycombinator exists, because they need to put as many small checks into as many companies as early as possible.
Daniel Scrivner (20:32):
It's the fat tail bet.
Andrew Dumont (20:36):
People need to understand this as founders, and people pitching VCs to raise money, is most VCs, they invest in hundreds of companies. They pull out the five that could become Notion, or Giphy, or whatever, but you need to understand that there's not some unfair analysis or whatever. It's not a very sophisticated activity, unfortunately, and that's just the nature of it. I think it's important for entrepreneurs to just realize that, which is why it was so important for me to get on the other side of the table, because I wanted to demystify it, and now that you have, it just feels so unsophisticated in a lot of ways.
Daniel Scrivner (21:14):
I love that you said that, because I feel the same way. I don't see many people taking that perspective, and sharing that point of view, but I think it's definitely true. In my mind it's just like forecasting markets is not a thing. Are there market forecasters? Yes. Does anyone have success at doing it repeatably? Absolutely not, so why would it make sense that venture capitalists can predict the future, and know exactly which companies. The other piece I was just going to say is, because I'm curious if you've had these experiences, and what you've learned from them, but I think for me, I've learned a lot from seeing the companies that go on to be big, and always being surprised at the ones that go on to be big, that's one.
Daniel Scrivner (21:51):
And then the second one is, just seeing all the different ways that companies can die, and how much that's eye-opening about all the ways that it can go wrong. Clearly, you've focused on getting these reps. A part of that is seeing companies have small exits, seeing companies shut down. What have you learned or pulled out from the companies that have just totally just blown up, or have there been any interesting insights or stories there?
Andrew Dumont (22:13):
I think it's just people, honestly. Yeah, it feels like a cop out answer, but it's really not. It seems from my experience where it's just so dependent on how resilient, and tenacious, and how much the founder believes in it, or founders believe in it. That's really what it comes down to, but I want to go back to your point there, and a lot of people don't share that perspective, and I'll tell you why, and it's because they're incentivized not to share that information. If I'm a fund manager, and my goal is to raise more funds, I need to make it seem like I have some unfair advantage that no one else has, because that is my ticket to go raise more funds, which is how I get paid, which is my livelihood. It is not in the best interest of the investors to simplify what it is that they do, and make it seem like there isn't some unfair advantage to it.
Andrew Dumont (23:07):
I think it's important to understand that dynamic, which is really like the Andrew Wilkinson perspective, where there's an incentive structure around VC that makes it so, that perspective is not shared much, and the world of venture, and investing is very small, where if I rubbed certain investors the wrong way, I don't get deal flow, I don't get into companies, so I need to tread as lightly as possible. For me, I don't have any desire to go raise another fund right now, or realistically, in the near term. I think, it's more important to share just the reality of what that world is for the entrepreneurs, because I care more about them than I care about the other investors.
Daniel Scrivner (23:45):
Yeah, and it's the real world take. It's actually how it works in reality, and I think a good point you make there is, maybe another way of saying it is, venture capitalists are in the business of mythmaking. They're trying to make themselves, and their firms into these mythical creatures, and it just doesn't exist. It's also why venture capitalists are hated. That's why things like VC brags exist, because to perpetuate those things, people know that there's not really anything there, but continue to have to do it.
Andrew Dumont (24:10):
But, until you experience it, you still believe that there's something there, and I think it's-
Daniel Scrivner (24:15):
Andrew Dumont (24:17):
Yeah, you hope, and that was just so obvious for me when I moved into this side, it just hit me in the face, and I was like, "This is it." I don't want to completely bash it, because it does good in the ecosystem, in some cases. Giving more people opportunity to start companies is a good thing. I don't want to push that down too much, but I just think it's important for people to understand the reality, so they don't go, and have these conversations with investors, and put them on this way up there, and feel like they have all the control, because they don't in that equation.
Daniel Scrivner (24:52):
It's all about expectations, and I think your whole point there is just have realistic, grounded expectations when you go into these conversations. We're skipping through this a little bit, because you just have a ton of experience, but so you have all of these early stage venture capital backed experiences, that leaves you with a sense that you want to move to the other side. I want to move on to now talking about all the work that you've done with Tiny, and to just start off there, can you share a little bit of the background of how you came to know Tiny?
Andrew Dumont (25:19):
I think I met Andrew probably seven, eight years ago, if I remember right, and I think I met him through Twitter, actually, which where all great relationships start these days. I think we met there, and we had just stayed in touch, and at the time, I think, I was in Seattle, and then, I moved to New York, and started working at Betaworks. And then, the other piece of my story is, I loved being in New York, and I loved that ecosystem, and then, my mom got a late stage cancer diagnosis, so I had to move back home, or I wanted to move back home to Seattle to be with her, as she went through that process. When I moved back to Seattle, I wanted to, one, give back to the local ecosystem, and see the other side of the table.
Andrew Dumont (26:02):
And then, I started talking again with Andrew, and at the time Tiny was getting momentum. This was probably, three or four years ago, and he had a little business that wasn't really getting a ton of attention, and he said, "Hey, do you want to do this off the side of your desk, and just do this along with investing?" For me, I was like, "Yeah, I'm bored as heck investing, and I don't really want to do this long term, so yeah, let me take some runs at that." That's kind of how I got involved with him, and with Tiny, and it's obviously grown a lot since then, and my involvement with them. I'm just a huge fan of them, and the way that they operate. They're just good people, and it's been really enjoyable to work with those types of people that have a longterm mindset on what it is that they're doing, so that's been a lot of fun.
Daniel Scrivner (26:47):
Yeah, they're incredible. It's an amazing experience to get to work with them, and just to clarify too, that business was Tiny Boards, as it's referred to internally. Can you describe a little bit about what that is?
Andrew Dumont (27:01):
Yeah, it started really with We Work Remotely, which is a remote job board. They had also acquired some smaller job boards as well, and they internally, this was before I came on, and created this entity of Tiny Boards, which included, primarily, we work remotely. That was three years ago or so, and it started with that business, which was quite small at the time, with the advancement of remote work, which obviously, is top of mind for everyone right now, and just the fundamentals of that business, and what we were able to do with it. It's actually grown a ton, and just become a pretty significant business, so that's been the primary focus, and then, I've since gotten looped into several other Tiny companies, running those companies for them.
Daniel Scrivner (27:43):
It sounds like a lot of the appeal was just to get to work more closely with Andrew, with Chris, with Tiny, but was there anything that interested you about the job board specifically? Because, at least from the outside looking in, I don't know, there's a bunch of things you could say about them. They're small, and they seem small, maybe throw away businesses at the same time, but has that fat tail where there's a few that make a ton of money. It seems like a perfect asset light business. I guess what's your take on it as you've worked through it?
Andrew Dumont (28:10):
Don't get me wrong. I was not looking at that business, and thinking, "Man, I really want to run a job board." It was more, I want to start working with Andrew in a formal way. This is a great initial opportunity, and one that I could do off the side of my desk initially. That was a real first hook in. Now that I've been doing it, they're fantastic businesses. They're super efficient, they're product light, like technology light, so you're not spending a lot of time and money on software development, and new versions of the product, and all that, and they scale really, really well. There's a bigger question of, how big can you make it in that existing model? And then, you start digging deeper, and you realize, ZipRecruiter is, I think $500 million a year type business. Indeed is a multiple billion dollar a year type business.
Andrew Dumont (29:00):
So, you see these examples, and you think, "Okay, well maybe there is more here." And, that's the next phase of that company, is start going down those different paths, and see what you can create in that remote work niche, which is now much larger. I think the biggest discovery is just how good of a business it is, both from a profit margin, revenue, efficiency standpoint, and scalability. It takes a pretty small team to operate that business. From a Tiny perspective, it fits right in their sweet spot in terms of the type of business that they like.
Daniel Scrivner (29:35):
I won't say on this too much longer, but I just had two questions I was curious to dive into around job boards. One of those is, just the concept of a moat. Do you think there's a moat, and what is that moat? And then the second one is, so in the case of We Work Remotely where you have this starting point of this acquisition you make, and you go about scaling it, thoughts on, I don't know, things you've learned along the way, things you've tried, just how you go about even scaling a job board.
Andrew Dumont (30:01):
Well, the moat is the audience that you have. The moat is the candidate base that you have. The thing that you'll realize about hiring technology, is that, people only care about the number of applicants, and the quality of applicants, and filling their role. As long as you are an efficient source to go do that for them, there's a lot of value that's placed on that. The biggest moat in that world is audience, and community, and candidates at the end of the day. Early on our biggest thing was let's build the pie up as large as possible. We invested really heavily in content production, in SEO, and being more efficient from that standpoint.
Andrew Dumont (30:40):
Paid acquisition, actually, isn't a huge mix for us, although it will probably have to be over time, but early on it hasn't needed to be, so we really invested in the longterm compounding assets that create value longterm, and I learned this at Moz. Moz is one of the best in the world. It was one of the best in the world at creating these long term assets that continue to produce value like their Beginner's Guide to SEO, where it lives out there forever. Sure, it takes a lot of time and energy to produce it, but it keeps paying dividends, and that's my general marketing philosophy is, I want to invest in the things that may not give me an immediate return, but give me a long term return.
Daniel Scrivner (31:22):
Sure, and compound over time.
Andrew Dumont (31:24):
Yeah, and compound over time. That's why, I think, a lot of the ecosystem is all about, let me just run Facebook ads, because the math works. Let's just keep going, and that's great as long as you have the money to do that, and as long as the math continues to work out. However, the moment I turn off my Facebook ads, they die, like that, die. This is one of the things I learned very early on at Moz, and it has been like the foundational element, is like, let's invest in the things that are not immediate return, but are long-term, and produce value for a very long time, and typically, that's content marketing, those are the heavy assets there. That was the philosophy, and that has scaled really, really well for us. But, remote work is getting super competitive. It's harder to maintain that moat now than it was, so that's really the next challenge for that company, and we'll see how we do.
Daniel Scrivner (32:15):
Sure, so competition increases, you need to find new ways to compete, and I guess new tactics. Just on the moat question, I guess, I don't know another take on that, or another perspective on that is, if someone wants to, and I'm sure potentially you guys see this as job boards, I think, I've seen them tossed about on the internet is like, it's a great starter business, you can launch one, you can build one, you can grow on, so it leaves me to believe that there's a lot being launched, and they probably-
Andrew Dumont (32:41):
Daniel Scrivner (32:42):
... don't grow to scale, but when you guys see that, what makes it so difficult for someone to go and clone, We Work Remotely, or try to rip you guys off? You've built up that audience.
Andrew Dumont (32:52):
It's super easy to clone and rip off, it happens all the time, so that's easy. The hard part is the moat, which is the scale, and audience, and the candidate volume, that's where that breaks. You need to be a great marketer, customer acquisition person, to get to a level where you can compete with, We Work Remotely, or some of these other players out there. If you don't know how to do that, the technology is not the thing there, so it is super easy to spin something up, and compete right away, but reaching the scale is the really, really hard part. The way I think about that is, we want to help those companies get started, and we had this philosophy at Moz too, where, like use our API, use our data, show our jobs on your board. We'll help you get started in that way, so we get more visibility, and they have the seeding of jobs to get started.
Andrew Dumont (33:40):
And if they become more competitive with us over time, so be it, but I would much rather be friendly, and get some value as they start growing by exposing our jobs on their board, than just trying to cut it out, if that makes sense.
Daniel Scrivner (33:54):
So smart, that's like the Trojan horse. Here's a gift, but it also gives to us. Then going from Tiny boards, I think it was last year that Tiny acquired Meteor, and you took over that, and you're onto something else now. Can you talk a little bit about the subsequent things you've worked on?
Andrew Dumont (34:13):
Andrew Dumont (35:00):
Daniel Scrivner (35:17):
What was the playbook that you followed or what have you tried and what has worked?
Andrew Dumont (35:21):
I've been thinking about this a lot, because I think that the process is very similar between all these companies, and I don't want to call it a turnaround, but it's like you take an acquisition, how do you make it grow from there? Let's not call it a turnaround, but how do you inherit an existing business, and make it become more successful? The way that I think about that process is, step one, make it more efficient. The first thing that I always do is, I go look at the fundamentals of the business, and I think, where is it inefficient? That's from a cost perspective, right? What software don't we need? How much are we spending on hosting? How can we get more efficient there? What sort of contractors or outside resources, or in-house, do we need all that, and does it affect the business?
Andrew Dumont (36:07):
You want to get the business to a better financial position from day one, that's goal number one. Then goal number two is, what are the quick wins? What are the things that we can do to immediately change the trajectory of this business? Typically, you'll find business model issues, you'll find that there's just no process for talking to existing customers, or expanding the relationship there for the people that are happy. You'll find all these just similar things. There's no motion on the marketing side, there's all this stuff that just keeps coming up, and oftentimes, it's the same three, or four, or five things that exists in every single one of these businesses that either stalls, or doesn't reach that next level. It's pulling those out, but it's really stabilizing the business, finding the quick win opportunities that are most likely, are usually in the business model, or in the go-to-market.
Andrew Dumont (37:01):
And then it's figuring out, what is the team that I need to really make this compelling, and that's what we've been lucky to find on the Meteor side is, Philippe, which is our main, our CTO, and the person that's leading that technology. He was a Meteor developer, super passionate about the platform, knows exactly where he wants it to go, way better than I would, so getting people like that, that can continue to drive it forward. That motion has been very interesting, and it's very similar from company to company.
Daniel Scrivner (37:33):
A lot of those things you touched on there, whether it's marketing related are things that would be really easy to observe, and intuit what to do from the outside looking in. But I imagine something you referred to, business model problems, which I'm guessing is pricing, packaging, that's is a lot more difficult, because you're not really sure what the right move is there. How do you approach that part of the problem?
Andrew Dumont (37:56):
Well, you talk to customers first, if you have them, and the beauty is, when you inherit a business, there's some downsides, but the good part is, is that you typically are starting with something. It's easy to go talk to customers, and get a sense of what the issue is, like where are they churning out? Where are they not utilizing it to the full capacity that maybe they should? Then you can start addressing those things. I've actually really enjoyed, because I spent a lot of time in the zero to one. I've really enjoyed the, once you've hit product market fit, how do you go become something more meaningful? The reason for that is, it's less of a guessing product development initiative, and it's more of a tweaking exercise, which if you've done it enough, you know what things to tweak and what knobs to turn. For me, I've really enjoyed that process, actually, which is not the sexy part, but for me, that's the thing that I've really enjoyed.
Daniel Scrivner (38:51):
One more thing I wanted to dig in there, because I've observed this, I've had my own experience with this, but when you inherit one of those business, like you described, oftentimes, things aren't super great. You're not inheriting a business that's scaling super quickly. It may be stagnated, or it's declining, and one thing that doesn't get talked about enough, there's the whole playbook of how do you turn it around? But the other component is completely psychological and emotional, which is, you feel like this thing's slipping through your fingers, or it's imploding. How do you manage that? Or, I guess, any tips on compartmentalizing that piece of it?
Andrew Dumont (39:24):
Well, I think it's just so important to piece it out, and not try to boil the entire ocean at once, and you also have to understand that if something is getting acquired or sold, there's a reason maybe why. You have to expect that there's some dead bodies around in that business once you dig into it, so that's just assumed, but generally, I think the biggest and most important thing is just to understand that you can't fix it all at once, and that's especially true when you're inheriting something, because if you started a company before, you're not setting the vision necessarily in that scenario. It's more about what business do I have today, and what do I want it to become, and what are the steps that I need to take to get there? And how do I want to prioritize those things? How do I want to segment them into different sprints, is how I think about that, and that's really important.
Daniel Scrivner (40:19):
Yeah. It's a great, super thoughtful framework. I want to transition in a second and talk about investing, but just on this side, and I know in these cases it's not like you're acquiring this individually. You're certainly part of it, you're coming in, you're leading that work. For someone who's listening to this, and wants that experience, or wants to acquire a business, any thoughts, pieces of wisdom you'd share with them?
Andrew Dumont (40:39):
I think it's a great way to get experience actually. If you don't want to go spin it up yourself, there's a lot of these smaller micro SAS, or micro scale technology companies that you can buy for a hundred bucks, 500 bucks, a couple thousand dollars, and you can get a run at it. I think it's a super interesting path if you are, maybe working at a company, and want to do something off the side of your desk, or get that entrepreneurial experience without the... Because it's very daunting when you have an idea, and you think, "Okay, I want to go start that." You start thinking about, "Okay, well, who's my co-founder? Who's going to build this for me? How long is that going to take?" How am I going to fund that?" All of that.
Andrew Dumont (41:23):
Whereas, if you buy something small, that's existing, and is maybe simple technology, you can jump right in, and as a non-technical person, I can find my way around, but it's not my expertise, opportunities like that are amazing for me, because I get reps, and I get motion on go-to-market, and acquiring customers. That's the experience that I'm best at, and for non-technical people, it's a great entry point to get in.
Daniel Scrivner (41:49):
Yeah, and a great way to get reps early on, in a way that, even hearing you describe, yeah, because I've had so many friends that do this, I have an idea, I need to hire a co-founder, it immediately puts you in that boiling the ocean where it's like it takes 110%-
Andrew Dumont (42:02):
Overwhelming, yeah, yeah.
Daniel Scrivner (42:03):
... but it's not going to happen.
Andrew Dumont (42:05):
Yeah, super overwhelming. Yeah, and what ends up happening in a lot of cases is you don't action on that, and you don't go do it, because it is so daunting, and then, those ideas just go away, and someone else does them, whatever.
Daniel Scrivner (42:15):
It's a difficult path. Transitioning, I want to start to move, and talk a little bit more about the investing side of this. I know that you have a small VC firm, Curious Capital, you founded that with Alex Chung, who's the CEO of Giphy, super interesting investments. Obviously, amazing co-founder. I'm curious with everything we've discussed, and having a really good understanding of the pros and cons of venture capital, what made you so curious and fascinated to go and do that?
Andrew Dumont (42:44):
Well, for me and that specifically, I was coming back to Seattle, which this is less exciting if you're not in this ecosystem, but for me it was how do I give back, and get involved, and provide an alternative maybe to some of these other, at the time, existing investor set that you had to work with here in Seattle? That was the primary thing, and then, after that, it was, I want to learn, and I want to do this firsthand. Joining a firm wasn't interesting to me. My mind is always, let me go do it, and let me understand it. For me, that was the main thinking there. Unfortunately, with the VC fund, you can't really bootstrap, you can't really hack MVP your way in there, although, I did, but it became very obvious to me that after I raised that first small fund, that I didn't want to keep doing this. I didn't want to keep raising money for the rest of my career, and that's the business that you're in as a GP, or a founder of a venture capital firm. For me, it was very obvious-
Daniel Scrivner (43:46):
And, because I have to ask, was that more, you saw the role as just fundraising, and that's not at all what brought you to it, or was it something else? Is it just, I guess, the management aspects of it?
Andrew Dumont (43:58):
Well, no, it's not the management aspects. It's the timeline that you're working with, and for me, I would much rather go build a company than build a VC fund, and I liked that motion a lot better. For me, it was a combination of that, and just the timeline to get to scale of a VC firm. The thing that most people don't realize is, unless I come from successful firm X, and I go out on my own, and I go raise from those same LPs, or I am independently very wealthy, or come from a wealthy family, the process to reach a venture firm that becomes large enough, or large, in general is, I raise small fund one, and then, I raise slightly larger fund two, and then I raise slightly larger fund three, and so on, and so on. That's a very long process, and you're signing up for 10, 20 years, and you have to really want to do that for the rest of your career.
Andrew Dumont (44:58):
That was not the intent that I had when I went in it. No, it wasn't really what I wanted to do. I saw all these other flaws in the business model and just like, I wasn't that interested in it, because I pulled this sheet off and it was not that interesting and exciting. It wasn't something that I wanted to keep doing.
Daniel Scrivner (45:17):
One of the things I want to get your take on is, because I had this experience where I think, from the outside looking in and as I understand it, it seems like you did some small venture capital investments than ended up raising this fund. There was this initial curiosity with it then jumping into the deep end. But what I found is, there's what you think the job's going to be, and then there's what the job actually is once you're in the chair and whether you like that or don't like that. What did you really enjoy? Or what do you really enjoy about investing? I guess what are some of the things that you would highlight to people is, I don't know, just things to be aware of or things to know before jumping in?
Andrew Dumont (45:54):
I think this is really important for people, because I know it's sexy now to go raise a fund and a lot of people want to do that. It's important to understand, if you go raise your own fund, the story of venture capital and being in that seat, is that you get to spend all your day talking to entrepreneurs and helping them and doing all that stuff, which is true, but it is a very small portion of your day. If you do want to go be a fund manager, raise your own fund, your primary role is raising more money and it will always be that way until you reach the point where I can raise a new fund in a couple of weeks, which is what a lot of these funds get to once they reach scale and have all the success.
Andrew Dumont (46:29):
But when you are first starting a fund, you're going to spend your first five years realistically, actively raising money from LPs. And that is your primary role. It is not interfacing with founders and everything all day and helping entrepreneurs. That's a small piece. I just think it's important that, if people realize that if I just want to work with entrepreneurs all day, join an existing fund. If I love raising money and I want to create my own firm and that's the most important thing for me and I really enjoy raising money, great, go start your own fund. But for me, I do not enjoy raising money that much. And that's the primary role of a fund manager.
Daniel Scrivner (47:06):
One of the things that I'm really curious to get your take on, because one, it's not talked about enough and just from what we've discussed, I imagine you have a pretty different take here, is how you go about due diligence in companies that you're going to invest in. Because I think, one, as we've already talked about, you're not going to predict the future, but you have to come to some way of deciding whether you're going to invest or not. What does that process look like for you?
Andrew Dumont (47:30):
Boy, I'm going to be probably more on the end of the spectrum of, it really depends on the stage of the company. I just think that's important to start with. If I'm investing in a company at series A, series B, series C and so on, I have fundamentals to diligence against, and you know this of course, but when you're doing angel investing or pre-seed, typically it's a team, an initial version of the product, maybe, if that, usually no traction or revenue of any kind and a deck.
Daniel Scrivner (48:03):
With like a $51 billion Tan.
Andrew Dumont (48:06):
Yeah. Right. Exactly. Always a massive tan, but no, I mean, that's it, right? Anybody that tells you, there's this super sophisticated diligence process, is just full of shit. My diligence, when it comes to investing is like, how excited am I about the space that they're building in and how ambitious is their idea around that? How much do I believe in the individuals and their ability to go execute against that? And lastly is, any other indicators. Is there a product to market? Is there early traction? How is that first product? How good are they at building technology and product? Because that's going to be an indicator for future success and that's it. At the end of the day, you just have to make the call. I don't want to say gut, but there is a component of, I've seen this before, because I've lived it before, either good or bad.
Andrew Dumont (48:58):
And you start realizing there's all these red flags, because you've been a part of them in the past. And you realize that maybe that's that red flag that I'm seeing, so let me just not do this one. It's not very sophisticated to be honest, at all.
Daniel Scrivner (49:12):
I feel very similarly. The best thing that I try to do is, I think my framework seems very similar to yours. I think the thing that I try to do, that's definitely been helpful, is just the process of trying to write down my thoughts when I make that investment. So I have something that's concrete to go back and look at. Just in that vein, I guess, has your process changed over time and or do you find yourself when something goes really well or when something goes poorly reflecting and trying to draw out or do you think there's really nothing there? I struggle with that.
Andrew Dumont (49:42):
Of course there's stuff there, but every single one of these companies is different and they all look very different. It's tough to just say, well, here was my mistake, let me not go and do that again. But I do think it's a worthwhile motion. And this is why being an investor for a long time, you're going to create more of those reps, just like we talked about the reps from the operating side. If you do this for 20, 30 years, you're going to have enough reps to start understanding. I do do the same thing that you do, which is, when I make an investment, I write down my thoughts on why, when I miss on a company that goes on and becomes very successful, I go back and I look and I see maybe what did I miss here. And then the ones that don't become success, fail for whatever reason, I do the same sort of analysis. There's not a great playbook there. And that speaks to the fundamental thing that is missing a little bit, at least in super early stage investing. I just want to preface it like that, this stage is very important to that process.
Daniel Scrivner (50:44):
No, I agree. And I'm glad you called that out because it is very, very different as you think about that. We've talked about advice for people that might maybe want to go raise their fund, but I'm curious. One thing that I noticed is, so I maybe had, I guess, a little bit of the inverse experience, where I started out as an investor first, had ideas about what was helpful that were largely shaped by what an investor would find helpful if they were an entrepreneur. Then started focusing much more seriously on an entrepreneurial side and had an aha moment. Like within two days being in the entrepreneurial role where I was like, wow, I have everything I thought was helpful as an investor is not helpful. What is your thought process there on like, what can investors do? What do investors do that's actually helpful for entrepreneurs and what do they do that's just totally not helpful at all?
Andrew Dumont (51:29):
Well, I'll tell you what I do, and this is educated by my experience as an entrepreneur, an operator. Every new investments that I do, I say, "Hey, my expertise is in go-to-market and customer acquisition. So if you need additional support there, let me know, okay?" I then give them my personal cell phone number, and I say, "Anytime you need anything, call me or text me." The real thing there that I'm offering is, accessible, I don't want to say therapist, but kind of therapist, that like when shit gets bad, because it inevitably does, give me a call and like, let's talk it out. My check isn't big enough where it's like, I'm going to be super upset one way or the other. That's my position that I take, at least in my role. And then I get out of the way and I'm there if they need me and if they don't then that's okay too.
Andrew Dumont (52:20):
That's at least what I wanted as an entrepreneur and as an operator, so that's how I've gone about it. That's how I approach it. But I think the biggest thing an investor can do is give that support, kind of a friend through the process, that's at their same sort of level, that they can just confide in. I think that's value number one. And then value number two is, there's all these pieces of the business that they're going to need help with. So being an expert in one area that they can go to is valuable. And then the last piece is, the next round or that future funding. Can you write another check or can you help me get in the door at one of these firms that I'd want to raise from in the future? But that's it really.
Daniel Scrivner (52:59):
I'm sure even with that process, you already a lot more helpful than most investors, because you're clear about where you can help. It's easier to reach you. One thing I wanted to talk about is just reflecting... I guess jumping to the other side of what we've been discussing. We've been discussing, starting to invest, raising a fund, what that looks like. Now I want to jump to the other piece, because I think this is something that's not talked about enough, which is, you've made a bunch of investments and you now are in the position where you get to watch them play out. I think just some observations I've had there is, I think most people investing in venture capital or early stage companies, have the totally wrong timescale.
Daniel Scrivner (53:35):
And in my thinking it's more like a 10 year timescale to where you're actually going to realize a return, which for a lot of people is, if you tell people, hey, you're going to make an investment, it could be an amazing outcome, but it's going to come in 10 years. I think most people would walk away. So it's just, the timescale is different. But then the second one is, as we've talked about, it's inherently a model where you're putting out a lot of checks, getting in a lot of reps, some of those are going to be big. A lot of them are not going to be anything, I don't know, any thoughts, observations on watching it play out in how that feels or what you've taken away from that experience?
Andrew Dumont (54:05):
I think you nailed it. The companies maybe that you don't expect to go and have this great outcome, they sometimes do. It takes a very long time. I've been fortunate in the first fund where three of the companies have gotten acquired already and they were really good acquisitions. That's a rarity, but it's just long term and it takes a long time. I think the bigger thing is as an individual, you probably shouldn't do angel investing.
Daniel Scrivner (54:31):
Most people should not. Absolutely.
Andrew Dumont (54:32):
And it's definitely like this, I see Kevin O'Leary from Shark Tank, do his commercial about making it accessible to everyone and blah, blah, blah. That's great conceptually, but it's a pretty asset class, from an individual investing standpoint. Every once in a while, sure, you may hit something big, but you need to write a lot of checks to go do that. And unless you have a massive amount of disposable income, it is probably the worst place you can put your money. I just think it's important for people to understand that.
Daniel Scrivner (55:04):
No, I'm so glad you said that. Seriously, it's like the things that people need to know is, 10 year time horizon. You probably need to invest at least $100,000 or more, trying to get to 20 plus startups. And then the third one, which I think everyone understands conceptually, but it's very different when you're in that position is, it's completely illiquid. You have these things that are potentially large gains. You don't see anything. There's no income, there's no capital gains. There's nothing until there's an exit. I think that when you sit there with that discomfort of seeing things go on to raise additional rounds, but having no idea if or when it's ever going to materialize, I don't know. Just very different in practice.
Andrew Dumont (55:43):
It's very different. It's just important for people to understand. And I get, don't get me wrong, I am one of the first person who learns by doing, and I understand the desire to do it, but that's okay. But just be aware of what you're getting into and the timeline and really how many checks you would need to write to have some success there. And even then that's not guaranteed in any way of course.
Daniel Scrivner (56:05):
Totally. It's like another way of saying that you're signing up to learn viscerally, that means it's going to be really uncomfortable, but that's what you take away at the end of the day. The price you pay. There's a ton of other stuff that I wanted to ask you about, but I'm going to hold that off and cross my fingers and hope we can do a part two someday. I'll move on to closing questions. One of those is, we did talk about, you've not only done, obviously a lot of venture capital investing, you've also invested in real estate and done some really interesting, fascinating stuff there. We'll save that for another time. But I guess one thing that I wanted to just try to close on is, what are you most excited about as an entrepreneur and an investor now? And are there areas that you just find really interesting and fascinating?
Andrew Dumont (56:46):
This is again, probably a weird answer. I could list off all the different areas, like, maybe digital currency or all these different areas that are remote work, all these different areas, and that's great. But I'm coming up on 13 years now in early stage only technology. I've just learned that, things move and change, and the things that you think are really interesting spaces, maybe prove not to be, or at least not right away. I really care less about trends and all that stuff and pontificating on what space is going to emerge and all that stuff. I'm less excited about that. I'm most excited about doing the work and getting the reps. I wish more people were excited about that, because I think it just, we need it more in our space, just doing the work instead of building your brand or doing all this stuff, which is valuable.
Andrew Dumont (57:42):
And I have been online for a very long time talking and doing all that stuff, that's what I'm most interested in, honestly, and it's not exciting or interesting or any of that, but genuinely like that's my real answer to that question. There's probably somebody else that will have a better-
Daniel Scrivner (57:58):
No, no, that's an incredible answer. And I'm right there with you. We'll leave it there. It's been an incredible conversation, but just for anyone listening to this that wants to reach out to you, wants to find you online. Where can people find you?
Andrew Dumont (58:11):
Used to be more active on Twitter, I'd like to get more... It's funny I just did that. On Twitter, AndrewDumont is my handle there. And then if you want to reach out to me on email I'm, firstname.lastname@example.org. I'm always online and accessible and I try to respond to everybody that reaches out. Please reach out.
Daniel Scrivner (58:32):
Thank you so much for doing this man, and thank you for your time. This has been wonderful.
Andrew Dumont (58:35):
You bet. Thank you for the time. I appreciate it.
On Outliers, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. Explore all episodes of Outliers, be the first to hear about new episodes, and subscribe on your favorite podcast platform.
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