Uncapped #54 | Sam Blond from Monaco

Sam Blond is the co-founder and CEO of Monaco, an AI-native revenue automation platform built to replace the CRM as the system of record for sales. Before Monaco, Sam was a Partner at Founders Fund and before that one of the most accomplished go-to-market executives in the tech industry, having served as VP of Sales at EchoSign (acquired by Adobe), VP of Sales at Zenefits, and Chief Revenue Officer at Brex. We discussed Sam's entire sales journey from EchoSign through Zenefits, Brex, and Founders Fund, and what he learned at each stop. Sam shared his framework for creating a demand-rich environment and why most founders misdiagnose their revenue problems as conversion issues when they're really pipeline issues. We got into why Sam believes Salesforce faces a classic innovator's dilemma and why the next category leader in sales will be a platform architected with AI in mind from day one. We also covered Monaco's go-to-market playbook, how Sam thinks about pricing when you're selling labor disruption rather than software, and his two pieces of advice for founders who are just starting to sell. Timestamps: (0:00) Intro (1:26) Sam's sales journey (3:11) Echo Sign takeaways (5:28) Building Zenefits GTM (7:02) Parker's 0 to $10M thought exercise (9:51) Creating a demand-rich environment (14:20) People, brand, and revenue ops (21:19) Why Sam went to Founders Fund (28:00) Why Monaco, why now (29:40) The Salesforce innovator's dilemma (31:40) Why Monaco chose to be the system of record (34:30) Disrupting labor (41:10) Pricing in an AI-native business (44:28) The Monaco GTM playbook (50:06) The $60,000 plane experiment (54:21) Creative campaigns vs. paid advertising (1:00:06) What Monaco actually does (1:03:13) Advice for founders just starting to sell (1:07:58) Abundant pipeline and the right to say no

• 0:00Speaker 00

  Buyers still want to talk to a person. They don't want to buy from an agent, a like, you know, Jack Altman avatar that shows up to a call that is like, not really Jack. So there's no higher ROI on my time than spending time with customers.

• 0:18Speaker 01

  Sam, what a delight to be here. I'm really excited to do this with you.

• 0:21Speaker 00

  Thank you for having me. Awesome to be here. I've been a fan of this for a really long time. So it's cool to be in this chair.

• 0:26Speaker 01

  I'm going to try to live up to the hype of that. So I actually first learned about you by reading Jason Lemkin's Sastro blog back when I was, you know, starting the last, trying to learn about sales. And I remember in there, it was like, you know, Jason's talking about my best, you know, sales rep at EchoSign, and he did all of this. Then I obviously knew about you through Parker, who we both know from, you know, Zenefits and Rippling. Obviously, so I've known about you for a long time. Obviously, I've gotten to know you well over the last couple of years. But I actually want to start by talking about sort of your sales journey. So can you talk through like, maybe just like a quick summary of like, how you came up through sales, you know, a bit about these companies, and maybe some of the things that you learned in each of those chapters?

• 1:05Speaker 00

  Yeah, we'll talk about lucking into some incredible company. So Jason and Parker, both of which you alluded to, two of just like, the greatest people, but also most influential people on the career that I've had, and just like, amazing advocates and close friends and all that stuff. So shout out to those guys. And so let's see, I grew up in Kansas City and went to University of Missouri. When I graduated, I was really fortunate that my older brother, Brian, was in San Francisco doing tech sales. I don't think I ever would have ended up out here but for that. So then, 22, moved to San Francisco, got into tech sales. I was at EchoSign, and I appropriately said, like, sort of lucked into the relationship with Jason. I was just like, you

• 1:47Speaker 00

  know, using a recruiter that was introducing me to early-stage startups. One of them was EchoSign, and I had a job offer and I took the job. And so I started as an SDR, as many folks do, in sort of early sales, go-to-market in tech startups. I was there for something like six years. The company did relatively well and afforded me the opportunity to move up into, you know, more senior sales roles within the organization. Then Jason introduced me to Parker, went to Zenefits, I was VP of Sales there for a few years.

• 2:22Speaker 01

  Crazy years there, which we can get into. But like, I mean, what a growth trajectory that was.

• 2:26Speaker 00

  Yeah, it was awesome. You know, I was there for a little under two and a half years. For two of those, almost two and a half years, it was incredible. And then like, towards the end, like, sort of left turn into lots of lessons and we can, you know, it goes deeper, or is not as you want there. And then, prior to doing Founder's Fund, and ultimately Monaco, most recently in the sort of sales career, I was CRO at Brex. And again, same idea, just joined a company that was really exceptional from a very early stage. And so I think three times have benefited from the experience of joining when companies are relatively unknown, and near $0 of revenue, and then being able to leave when they were much, much larger and lots of revenue.

• 3:09Speaker 01

  Yeah, so we can spend the least time on this because it's like, reaching far back into the past. But like, what did you take away from EchoSign? Like, obviously, those were formative years for you, as you thought about like, what good sales looks like, and what a good go-to-market machine looks like. But like, that's probably where you got a lot of your early ideas about how this stuff should work. So like, what were your takeaways there?

• 3:28Speaker 00

  Yeah, well, I think there was some-

• 3:30Speaker 01

  Were you guys up against Doc? Was DocuSign like-

• 3:31Speaker 00

  Yeah, that's right. So DocuSign was a competitor. EchoSign was private for like, three or four of the years that I was there. And then Adobe had acquired us. EchoSign became AdobeSign after the acquisition. We were actually beating DocuSign when Adobe acquired us. And DocuSign is maybe the more familiar name now, because EchoSign evolved into AdobeSign. And so, let's see, a couple of things stand out. First and foremost, and again, I genuinely lucked into this. I think there's like, nothing more influential early in one's sales career than the company that you join. And you control a little bit of the success of that business. You know, I was in SDR, and then I was a sales rep. And I was one of, let's call it like, 10 growing

• 4:14Speaker 00

  into 40 salespeople. There's only so much that I can sort of attribute EchoSign's overall success to me.

• 4:20Speaker 01

  It's funny, I put this in the true but hard to convince people of bucket of things where it's like with, you know, somebody early in their career. It's like, you know, you've got like, compensation, title, and quality of company. And it is very hard sometimes to convince people that quality of company is more important than those other things.

• 4:37Speaker 00

  It's arguably like, we can of course, deal with the other side. It's arguably like, the only thing that matters. Especially if you are joining as it is starting to take off. The way that I think about these things, a lot of it is like, the risk reward. And like, the earlier you join, almost definitionally, there is more risk. But if you can join like, right at an inflection point, when there is some signal that this company is really about to take off, but you also join in a very early stage, where you were like, the first, the second, the third, the fourth hire in the role or function that you were joining in.

• 5:06Speaker 01

  And then the path dependency on the career from there just is like, so, so strong.

• 5:11Speaker 00

  That's exactly right. So EchoSign, there was this thing that was largely outside of my control, that was like, the overall success of the business.

• 5:19Speaker 01

  Product market fit was just good.

• 5:20Speaker 00

  That influenced my personal success, as much as anything. I think there is like, a different variable here. I, I have, I sort of lucked into or found a career path that is a good fit for me. Like, I enjoy this a lot. And I'm pretty good at it in ways that, had I tried something different, I would have probably been less good and enjoyed it less.

• 5:45Speaker 01

  Well, I want to go, I want to go to Zenefits. Parker, obviously, one of the great founders of, you know, the last decade. And, you know, obviously, Zenefits in some ways, like, you know, he basically rebuilt Zenefits, and figured out like, you know, these are the product things that need to happen for this to be a super durable company. But there was really strong product market fit there. But I think, equally notable, the go-to-market machine and apparatus that early Zenefits had was like, remarkable. And so like, yes, in the end, like, some product things weren't there. But like, can you talk about that early scaling? Because I think it was like, at least of that, you know, it was maybe what, 2013, 14, that it was scaling, something like that?

• 6:23Speaker 00

  Yeah, I joined in December of 2013, and then Parker and I both left around the same day, left in quotes, around the same day in 2016. I think it was February of 2016.

• 6:33Speaker 01

  Can you talk about what building that go-to-market machine looked like in those early days?

• 6:38Speaker 00

  Yes. So, let's see. We've talked about Parker a little bit. I think, an inspiration in a couple ways, just in terms of like, learning so much on how he is a founder and CEO and runs a business. There's just like, a lot of lessons there that you sort of organically-

• 6:53Speaker 01

  What's one-

• 6:54Speaker 00

  -learned from?

• 6:54Speaker 01

  What's one that you like, come back to a lot?

• 6:57Speaker 00

  There was a thought exercise in March of 2014, that we, when I signed up for Zenefits, we had a revenue target of going from effectively zero, maybe it was a few hundred K, when I joined in December of 2013. So we were creating our 2014 plan. We wanted to go from effectively zero to $10 million of ARR by the end of 2014, so in 12 months.

• 7:18Speaker 01

  Which, by the way, in 2014, you know, now that people are like, ah, but that's like, that's like, today, somebody saying zero to 100.

• 7:23Speaker 00

  That was sort of unheard of. And Parker, let's see, Parker, as he should, has sort of like, very ambitious, dream big aspirations and expectations. And so zero to 10 million was like, there weren't a lot of other startups that were doing it. And so then, early in the year of 2014, we were trending towards more than that. And so he sat me and Matt Epstein down, who was leading marketing, and said, let's go through a thought exercise of, instead of finishing the year at 10 million ARR, which is our like, you know, stretch goal, or however you want to frame it, what does it look like if we finish at 20? And we want to back into sort of like, what are the headcount implications of doing this? What are the sort of like, lead implications

• 8:06Speaker 00

  of doing this? How many leads would we need? What would the marketing spend look like? And you sort of like, do whiteboard session on, I don't know, Monday night or whatever, and you end at 1 a.m. And we kind of like, look around the room, and Parker's like, well, we're not going to tell the board yet, but we're going to do this. And three days later, he told the board, like, the new goal is 20 million in ARR. So there's a takeaway that you can like, apply that process to all sorts of aspects of the business.

• 8:29Speaker 01

  And is that basically, does that boil down to just like, people rise to the level of expectations you set, and just pushing the boundaries of what great could be, just sparks, you know, more achievement? Is that kind of it?

• 8:40Speaker 00

  I think there's something there. I also think that there's something around like, manufacturing urgency, and having like, really audacious goals. And there's probably like, several takeaways, but that specific process is one that I try and apply. And it can be, it can be something like, a revenue target. It could also be something like, how long is something going to take? What would it take, actually, if we needed to do this in a shorter amount of time? And what would sort of be the trade-offs and those sorts of things? And so it's just, operating rhythm of the business, something like that.

• 9:08Speaker 01

  Okay, so you have these ambitious goals for the year. So then, like, what goes into that? Like, when you said, okay, what does need to be true to go to 20 instead of 10? Like, what's the, what is that conversation?

• 9:17Speaker 00

  Well, I think one of the things that we benefited from quite strong product market fit at Zenefits. We benefited from the same at EchoSign, at Brex, now at Monaco. And so then I think that's worth highlighting. I do think that there's like something that we were pretty deliberate about at Zenefits that I took with me to both Brex and now Monaco is being like very intentional about creating what I would describe as a demand-rich environment. And I think that many founders, sales leaders, startups broadly,

• 9:58Speaker 00

  sort of misdiagnosed the opportunity to acquire customers and grow revenue more quickly as something related to conversion rates. So like, we have these opportunities that we're tracking. We're in July of 2026. If we look back to June of 2026 and we maybe missed our revenue target. The reason that we missed that is because like, you know, gosh, this one deal that we really thought was going to come in and the sales rep said it was going to come in, it pushed. And so had it come in, we would have hit our revenue target or something like that. And my diagnosis in many of those instances is actually something like, you should have had like five deals.

• 10:36Speaker 01

  Yeah.

• 10:37Speaker 00

  And if three of them close, you finish way over target.

• 10:40Speaker 01

  Yes.

• 10:40Speaker 00

  And if that one deal closes, you actually hit your target. But in a lot of ways, like you could have done better.

• 10:45Speaker 01

  I can't remember who it was. It was either you, Parker, or Matt Epstein. But one of the three of you told me at some point, when I was like trying to get, you know, go to market advice for Lattice. It was like, look, you can improve your conversion rate by this much. You can improve like your, you know, first deal to up. But like the thing that you can change by 10x is your top of funnel.

• 11:05Speaker 00

  That's right.

• 11:05Speaker 01

  And I think that was always deep in, you know, this group's psychology is like, you can improve all these things a little bit, but you can improve the top of funnel. Like, if you have a company worth building, there's like 100 times more customers that you could be talking to than you're talking to. I think this is like a very underrated thing and it's like, kind of like a red pill once you see it.

• 11:25Speaker 00

  It's something that we have lived by and I think benefited from. And just to sort of like reinforce the thing that you just said. I would, well, if you have 10% conversion rates, improving those conversion rates to 20%, which sounds like you're improving your conversion rates by 10%, but you're actually doubling the conversion rate. It's really hard.

• 11:48Speaker 01

  Yes.

• 11:48Speaker 00

  And especially like, you know, if you have a sales organization, you have to like train the salespeople. If you're a founder, you have to get like far better, like pitching and closing and all of these things. If you have a large enough addressable market. And so this doesn't totally work if you have like 50 potential customers that you can sell into. But for companies like Monaco and many other startups out there, it is far easier to double your leads or opportunities. And so that is where I would put a disproportionate amount of intition. And if you do so, actually at the expense of either conversion rates or maybe like efficiency, that is a worthwhile trade-off. And so if you feel like-

• 12:28Speaker 01

  As long as like on a per rep basis, they're still closing enough per person per year kind of thing.

• 12:33Speaker 00

  As long as your growth trajectory is dramatically increasing month over month. If you have something-

• 12:41Speaker 01

  If you want the efficiency per rep, do you care about that? Or is that something that doesn't matter till later on?

• 12:46Speaker 00

  Yes, but you can apply the same logic that we just did at the company level to the rep level also. So I would rather deliver two times the number of leads or opportunities to a rep and actually have their conversion rates like come down slightly. Then give them less leads and increase their conversion rates.

• 13:03Speaker 01

  Just singular through, like focus on the throughput.

• 13:06Speaker 00

  The outcome.

• 13:07Speaker 01

  Yes.

• 13:07Speaker 00

  How much revenue did we close as a business this month? How much revenue did each sales rep close this month?

• 13:12Speaker 01

  Yes.

• 13:12Speaker 00

  There aren't, what's my dad say in golf? There aren't like pictures on the scorecard or something like that. And so like if a rep closes, I don't know, a couple hundred thousand dollars a month. It's not like, and I say this thing to reps all the time. It's not like there's like an asterisk.

• 13:26Speaker 01

  There aren't points for what your close rate was.

• 13:28Speaker 00

  Yeah, it's like, but you forgot to email this customer that otherwise could have closed. Like $200,000 of ARR closed this month. Like that is the thing that you see. And so like, of course you want to, the details matter. And of course you want to be constantly improving and giving feedback and all of those things, but solve for the outcome.

• 13:44Speaker 01

  Yeah, that's good. So what did you take then when you went to Brex? So like you had the Zenefits experience. It was both amazing and, you know, difficult in all these ways, which, you know, are well documented in the end. But then Brex was like this amazing run. So you've now had the EchoSign experience. You've gotten the chance to be the leader from, you know, basically the get-go at this next company. And now you're doing it again, you know, with the lead seat and the experience. So now, now what, what happens at Brex?

• 14:14Speaker 00

  Well, I'll touch on the two things that I think, actually the three things that influenced Brex's outcomes while I was there as much as anything. Two of which were true at Zenefits. One of which was actually a learning from Zenefits that we started far later than we otherwise should have, that we were able to capitalize on early at Brex. Then we can kind of do the same thing if it's interesting for Monaco, because it's a different world today than it was in 2018. The three things, the first is like recruiting and building the team. At Zenefits, my first two hires were the top two sales reps at EchoSign. Brought them with me. Their names are Matt Plank and Jamison Young. Matt Plank is now the CRO at Rippling.

• 14:59Speaker 00

  Jamison Young was CRO at Gong. He's now SVP of something important at Rippling in their sales organization. So these are like two of the people that have actually influenced my, my personal success as much as anything. And then you can just imagine that sort of cascading from there. And so at both Zenefits and Brex, now at Monaco, like we just have an incredible sort of like NFL level of players in a sales organization. And I think, you know, we can attribute so much of the success of the go-to-market organizations at these companies to the people that exist within the go-to-market organizations. I think the second thing, we touched on it, so we don't have to go much deeper. If you think about early days of Brex,

• 15:45Speaker 00

  one thing that we did, I think a very effective job of, was going out of stealth to like everyone knowing and talking about Brex very, very quickly. And we did things like huge billboard campaigns and gifting campaigns and fundraise announcements and so much of the stuff that like maybe hopefully like Monaco is known a little bit for today.

• 16:05Speaker 01

  But you got really loud. I remember that.

• 16:06Speaker 00

  Really loud, yeah. And I think the idea was like, we want as close, I don't know if we were as intentional as we are at Monaco today about this, but the idea is that like, we wanted close to 100% of our target market to have heard of Brex. And so then when we reach out to founder, finance leader, controller from Brex.

• 16:25Speaker 01

  It's not cold.

• 16:25Speaker 00

  You know who we are. And hopefully have like some positive brand association with that. So we were very deliberate about that. And I think again, like the concept of creating this demand-rich environment was something that we were very deliberate about early on at Brex. The third thing that I think we did, gosh, over time, the like grade improves, but at Zenefits we get something like a D+ from an early stage, is like the influence of what would be considered today as revenue operations. And it's just being very thoughtful about, well, here's maybe the easiest illustration of this. Not all leads are created equal. And revenue operations is like far more complex than this specific example.

• 17:11Speaker 00

  But I think this specific example helps highlight the influence that it can have. Not all leads are created equal. And there's going to be influence both on like the type of company that the lead or opportunity that you are potentially selling to. There's also going to be influence at like the persona level. So who is the person that we are meeting with? One thing that we did at Zenefits, there was a mistake, is we treated all leads or opportunities, two sides of the same coin, as being equal. And so we had things like opportunity goals. That was sort of the thing that like fed into what is the ultimate outcome of revenue. That was wrong, because what we started doing was getting more lower-quality opportunities that converted at lower rates that led to less revenue. And so over this like year of 2015, which was a more challenging year for Zenefits

• 17:56Speaker 00

  than certainly the 2014 year, I attribute a lot of that to the like diminishing quality of leads and opportunities. And so the thing that we invested in early at Brex was really understanding like, what are the trends in the business? And trying to pattern match to what are the companies and people that are most likely to convert? And applying that learning back to the sort of top of funnel? And where are we pointing our missiles at targeting and acquiring these opportunities? And so then you get the best of both worlds. You get a lead-rich environment with the right type of people and companies that you're trying to sell to.

• 18:28Speaker 01

  Yes. One of the things that I'm curious about is for Brex, obviously you had, and this is true at all these companies, but at Brex, there was this known highly competitive market with Ramp. And I'm curious about, and I would say today more than ever, basically every founder is operating in an extremely competitive environment. Like, I think it's felt this way for a long time, but like, it really feels that way. You know, like all good ideas have many, you know, many contenders going at once. What did you learn about competition through these? And like, how did you go to market through highly competitive markets?

• 19:05Speaker 00

  You know, it's interesting. EchoSign was certainly competitive with DocuSign. And so I think lots of learnings in terms of how to compete through that experience. Brex evolved into being hyper competitive with

• 19:19Speaker 01

  Yeah, but it started wide open.

• 19:21Speaker 00

  Interestingly, it was actually pretty greenfield.

• 19:23Speaker 01

  Yeah.

• 19:23Speaker 00

  When, when, for the majority of my time there, so my years at Brex were 2018 through like beginning of 2022. So 2018, 2019, even 2020. It was mostly a one horse racer. There was a company called Divvy that was acquired by Bill.com a little later. So there were other players in the space, but Brex was always like the market leader. And then I think dynamics of the market evolved, you know, starting in, let's call it 21, 21, and then certainly beyond. And I actually, what was not with the business for much of that period of time. And then Peter has this saying that's like, Peter Thiel has this saying that's like fairly famous. That I think like, it is oftentimes, to your point, hard to apply to enterprise software.

• 20:08Speaker 00

  That it's seemingly like inherently competitive.

• 20:11Speaker 01

  This competition is for losers.

• 20:12Speaker 00

  Competition is for losers and gosh, like, he's so, of course he's right because he's always right. But, you know, experiencing Brex in what I would describe, you know, I said this term previously, it's greenfield environment.

• 20:27Speaker 01

  Yeah.

• 20:28Speaker 00

  Pretty smooth sailing.

• 20:29Speaker 01

  Yep.

• 20:30Speaker 00

  Monaco today, we think of it as pretty greenfield. And so we are displacing incumbents.

• 20:40Speaker 01

  Yeah.

• 20:40Speaker 00

  But aren't competitive today with many new entrants into this space.

• 20:45Speaker 01

  Yeah.

• 20:45Speaker 00

  We should just sort of like assume that that environment won't last forever. But we want to take as much advantage of it as fast as we possibly can to get like as close to a monopoly as we can. And then evolve from there. And I think there probably are learnings from the time at Brex, just in terms of focus and how quickly you want to move into different markets and segments and those sorts of things.

• 21:06Speaker 01

  Yep. Okay. I want to come to that before we do after, so, you know, this like obviously extremely sort of like this rich journey through sales. After that, and before Monaco, you did spend time at Founders Fund and you have like a new chat, like a chapter to your life that was not about startup sales. So like, can you talk about what that was, that experience, what you learned? Why'd you come back to what you're, you know, a new version of what you've been doing?

• 21:32Speaker 00

  Yeah. Well, look, I, I've, you and I have both talked about Jason and Parker. I'd be remiss if I didn't mention something about like the learnings from Pedro Enrique Michael, who is CEO and now CEO at a company called Figure. And so like equal sort of parts inspiration and then, let's see gratitude for, for the influence that they've had on my career as well. And again, just like every single time I have been so fortunate in surrounding myself with the greatest people on earth. You know, like you go from Jason to Parker to Pedro Enrique Michael, and then we get to Founders Fund, right? And it's like, you've had folks on this, many of the folks on the show were talking about Brian, prior to, to starting the recording.

• 22:14Speaker 00

  But gosh, Peter, Brian, Trey, everyone is just like exceptional there. So let's see, I think I, I can get a little bit personal on, on like my mindset after Brex.

• 22:26Speaker 01

  Yeah.

• 22:27Speaker 00

  So this is late 21, early 22, I'm reaching like my four year sort of tenure at Brex.

• 22:35Speaker 01

  COVID.

• 22:36Speaker 00

  It is COVID. I'm in Miami.

• 22:37Speaker 01

  Yeah.

• 22:38Speaker 00

  So I, I've moved to Miami at this point and, you know, I, I just felt like for the first time in my career, I, I felt satisfied, which is very, it sounds positive, it's actually bad. I, I felt like sort of satisfied with what I had accomplished in this like category or world of technology sales. And, you know, I could have, let's make the assumption that I was leaving Brex. I could have done something like go either early stage and maybe like a more strategic title or something. But I would effectively lead go to market at a company.

• 23:10Speaker 01

  Yeah.

• 23:10Speaker 00

  Just like definitionally, the probability of joining an earlier stage company that has a Brex like outcome. You know, we were a 12 and a half billion dollar company when I left, which is like definitionally low.

• 23:18Speaker 01

  And it's like, even if you did, it's like, it was kind of the same, it was just a bigger number.

• 23:21Speaker 00

  I, I was, I wasn't motivated to, to do it. Like I wanted a new challenge. You know, I alluded to my brother Brian very early on in this sort of like career arc that Brian was out in, in San Francisco doing technology sales when I moved out here. Brian at the time had transitioned, he was a CRO at a bunch of really incredible businesses. And then he was a VC at Sutter Hill. I mean, so I, I had seen him make this transition as, you know, like former sales leader. And I was in Miami, I got to know Keith and Founders Fund had a Miami office and I made the decision that I wanted to get into venture. And gosh, if I had like the opportunity to join one of the greatest venture capital firms in the history of the world, I'd sort of be silly to not like take advantage of that.

• 24:02Speaker 00

  And so mid, late 2022, I joined Founders Fund and like couldn't be more grateful for the experience. And the people in the firm are just like truly exceptional. No surprise to, to anybody that's potentially listening to this.

• 24:20Speaker 00

  We weren't deploying a lot of capital at the time. This is like 22, 23.

• 24:23Speaker 01

  Yeah.

• 24:24Speaker 00

  And I, I think like I'm, at the time I'm Miami based VC. It was a little fish out of water. And so I don't know, you know, I talked about like, I did this thing at Echo Sign and then beyond that I could just tell like this is a good fit.

• 24:38Speaker 01

  Yeah.

• 24:39Speaker 00

  I don't know, certainly being in Miami, but I don't know that like being in VC, it felt like the right fit. One of the things that Founders Fund has a track record of doing that I gravitated towards is incubating companies. And so certainly like Peter, the, the most famous of them with Palantir and then Trey with Anduril. And there's a bunch of folks that have Scott with General Matter and Delian Vardenmore. And so my brother, who I alluded to at Sutter Hill, he took this model to human capital. We decided to co-incubate a company that evolved into Monaco. And through that process, I was sort of gravitating far more towards like, what is the right fit? It's building Monaco and not being Miami based VC.

• 25:20Speaker 01

  I, I asked you the other day, just like about like, you know, I don't even remember why, but it was about like, you know, interests outside of work. And you were kind of saying like, well, to be honest, I don't really have hobbies right now. I'm just working a lot. But you're like, you know, I did have them in Miami and yeah, was that like a, it, it feels to me almost like you had this like very busy career. It almost feels like you took a breather and then you're like, I'm going back into the coal mines.

• 25:47Speaker 00

  Potentially unintentionally, meaning the take a breather. I, I think what you said is, is exactly correct. And this, this maybe like, it could be received negatively, meaning today I don't have many hobbies. And if I'm not literally in the office, I'm thinking about Monaco and doing something sort of related to the business.

• 26:09Speaker 01

  I think it's very lucky to be so immersed in something that you don't have any hobbies. I think that's like a blessing.

• 26:13Speaker 00

  Yeah, no, it was, it was, it was certainly a deliberate decision. Like, like I knew that, that this was what I was signing up for when I made the decision. And to your point, yeah, when I was in Miami, gosh, I was in really good shape. And maybe that's like correlated both with the place and the, the like flexibility of the job or something like that. I, I was on the water a lot. There, there were plenty of hobbies that existed. And when I went all in on Monaco, you know, I moved back to San Francisco, I live right by the office. It, it is.

• 26:44Speaker 01

  High contrast, chapter to chapter, though.

• 26:46Speaker 00

  Totally. It is, it is 180, like, like fairly stark contrast. And again, it was deliberate and thus far I'm like very happy with the decision. I'm loving this. It's awesome.

• 27:00Speaker 01

  Okay. So let's talk about Monaco. So I guess, so this is why you started a company, like why this company? Like why, why was this the one that you're like, I mean, I guess it's a little self evident, but like what was in your head where you're just like, you know, this, this is going to be what I'm going to do?

• 27:13Speaker 00

  It wasn't part of the plan, meaning I had joined Founders Fund to be AVC. I didn't join Founders Fund thinking I was going to start a company, move to San Francisco, actually become co-founder, CEO of the Founders Fund, right? And so started this company, it, it like was just pulling me and felt very much like this, this is so obviously what I should be doing in my calling. So I think part of it was

• 27:38Speaker 00

  just the fit for me. And I think maybe the, the best way of articulating that is something like, there's only one type of technology company I'm qualified to be the founder of, and it is a sales or go to market technology company. There is this other thing that is highly influential and that is timing. And We are in the sort of early innings of this platform shift that is AI. And I do think that there will be a new market leader that emerges in the category that we are building in, which is go to market or sales technology.

• 28:14Speaker 01

  Yeah, it's like this paradigm, you know, in some ways seems to be like, I guess, going back to cloud. It was like, you know, I guess neither of us were really working at the beginning of that shift. But it was.

• 28:27Speaker 00

  Maybe we're students of history, though, or something like that.

• 28:30Speaker 01

  And it's like, you could see that basically, it's like, there are all these on-prem companies.

• 28:33Speaker 00

  Yes.

• 28:33Speaker 01

  And if you started a cloud company at the right time, it was just really hard for those old companies to turn the boats quick enough to come do what you were doing. And it was just a genuinely better offering for customers, and so it just dominated. And then just like category after category, like the cloud version just won. And the old companies couldn't get there, and the customers just preferred it and bam. And it seems like in AI, there's a version of this happening now where it's going from selling tools to selling the work. And it's just dominant to customers, and the old companies can't seem to catch up.

• 29:03Speaker 00

  I think you articulated it perfectly. These platform shifts rhyme where Siebel, that was maybe the incumbent or market leader in this category that Monaco is building in, which is go to market or sales, was the market leader. There was nothing inherently wrong with the business. In fact, like, one of the most incredible businesses at the time in history. The same thing is true with the market leader today, which is Salesforce. Just incredible business. And I think that they are, any market leader, and you can pattern match to other functions within enterprise software, that they're faced with an innovator's dilemma, where they have an existing set of customers

• 29:48Speaker 00

  on a platform that was architected pre-AI. And so they can either continue serving the needs of those customers and focusing on where they are generating revenue and building on top of this existing platform, or they can disrupt themselves. And seemingly every time businesses are faced with this innovator's dilemma during a platform shift, they gravitate towards the former, which I think for us equates to opportunity, where we can, and by the way, I think like, what Salesforce and what other companies are doing, they are overlaying AI on top of a pre-AI system architected platform, which is better than no AI.

• 30:32Speaker 01

  Yeah.

• 30:33Speaker 00

  But less good than being truly AI native, which is what a company like Monaco is.

• 30:38Speaker 01

  Yes.

• 30:39Speaker 00

  And so for us, we can go after a sort of narrow segment of the market today, which is startups. And if you think about Salesforce's revenue, how much of Salesforce's revenue is concentrated in tech, or early-stage technology startups?

• 30:52Speaker 01

  Less than 1%.

• 30:53Speaker 00

  Certainly less than 1%. And so we can go after that market, we can build a better platform, we can build a platform that's truly AI native. We can get, you know, close to monopoly market share there.

• 31:04Speaker 01

  Yeah.

• 31:04Speaker 00

  And then we start to move up market, and we start to organically expand outside of startups. And hopefully, eventually evolve into the market leader. But whether it's us or somebody else, it seems a foregone conclusion that the category leader, the platform of record in sales, in, let's call it, five years, will be a platform that is architected with AI in mind, and not one that was architected 20 years prior.

• 31:32Speaker 01

  You had a choice to make, which was, obviously, what you're selling is like work and outcomes, and you're selling sort of like revenue in some sense. You chose to also be a system of record. You didn't have to do that, but you made that deliberate choice. I think to the extent that you won't integrate with the system of record, even though you obviously could. You can imagine a world where you chose to do that.

• 31:51Speaker 00

  Most do.

• 31:52Speaker 01

  Many other companies, right, because it's easier to say, look, I'm not going to try to, you know, be your HubSpot, but I'm going to give you these tools that let you get more revenue and set up all these meetings and do all the, you know, accoutrements around the CRM. You've chosen to say, if you want to work with Monaco, we're the CRM. Why did you choose that?

• 32:07Speaker 00

  That's right. Well, several reasons. I think there are two categories of companies that are sales products. There are system of record companies today, that is a CRM. We actually believe that forward-looking, this like concept or category of a CRM will evolve into something of the past. We are more orienting around outcomes. And so we think that what today is this like system of record that manifests as a database CRM eventually becomes a revenue automation platform that's actually oriented around outcomes and not things like storing data. So we believe that there is like a new type of company that emerges from this

• 32:49Speaker 00

  that is a system of record, but doesn't look like the existing systems of record.

• 32:53Speaker 01

  What does it mean to be the system of record if not just like a database? What is it?

• 33:00Speaker 00

  It is, well, look, HubSpot is appropriately named. It is the hub. Everything orchestrates from the system of record.

• 33:08Speaker 01

  Yes, because it's the source of truth of data.

• 33:10Speaker 00

  And that's right. And you asked a question like, why did you make this decision? Well, if we, if we probably, if we bucket these company types or products into two categories, there's system of record and there's point solutions. Point solutions are layers on top of what today is a CRM system of record. If we think about the outcomes of those types of businesses backward-looking, we have market leaders like Salesforce that today are 120-plus billion-dollar companies. Just a few months ago are significantly larger than that. And then several others that are actually like quite large businesses.

• 33:42Speaker 01

  Yep.

• 33:42Speaker 00

  If we think about the category of point solutions that integrate to these systems of record, there are some that experience some early revenue growth and early maybe marks of low to mid-single-digit billion-dollar valuations. But none of them, historically speaking, have realized generational technology company outcomes. We're not motivated by being a point solution. We're not motivated by an outcome, which are, again, like, a really exciting outcome for those that experience. We want a shot.

• 34:14Speaker 01

  Yep.

• 34:15Speaker 00

  We want a shot at being a market leader

• 34:16Speaker 01

  Yeah.

• 34:17Speaker 00

  in the, one of the largest categories of enterprise software that we think will actually evolve from here. If you think about Salesforce and maybe enterprise software companies today broadly, their market caps are predicated on IT budget. We are disrupting labor.

• 34:32Speaker 01

  Yeah, that's right.

• 34:33Speaker 00

  And so the future market leader has both that IT budget, but also has the labor budget. Monaco is way more expensive than the sort of legacy system of record products, because we are doing the labor on behalf of our customers.

• 34:47Speaker 01

  Which, by the way, is the story of all these AI-native companies, is it's both dramatically more expensive in some sense, and it's also dramatically cheaper in another sense than what you would be doing alternatively to get the same outcome.

• 34:58Speaker 00

  That's exactly right. And people, not only are customers willing to pay, this is what they want. The other, you asked a question that maybe I want to touch on, because I think it could be insightful or maybe helpful for other founders that are starting businesses today. There's an application of AI in Monaco-like products that is seemingly obvious, which is, we are AI-native, we just talked about it, it's the labor disruption. We are using agents and compute to replace workflows that founders and salespeople would otherwise be doing themselves. And it is more expensive when a human does it, and it actually produces worse outcomes when a human does it.

• 35:42Speaker 00

  The thing that I think is like less obvious in terms of an application of AI that we've been very deliberate about, certainly intentional from the very early days, the cost of building software is trending to zero. And so we want to take on as much scope as we possibly can, starting with the system of record, but also displacing all of these point solutions that we believe are actually features of a broader platform and not independent product lines or independent businesses in many cases.

• 36:08Speaker 01

  And by the way, this extreme breadth focus was obviously sort of, you know, like, Parker was kind of like one of the like early canonical examples of like, the, what a software business really is at the end of the day is like these customer relationships that allow you to extremely efficiently build and sell more products to them. And you, you know, the customer just gets a straight-up better experience because the data is tied together. It ends up being cheaper for them in summation. You don't have to have all these different vendors, like all these things. Seems like now with AI, you should actually take that to an extreme degree.

• 36:41Speaker 00

  The compound startup, maybe phrase or terminology that I think Parker made famous.

• 36:46Speaker 01

  Yes. And now it's like that should go like exponentially far.

• 36:50Speaker 00

  Well, and I think Parker, to his credit, was probably ahead of his time on this, right? Because Parker started Rippling in something like 2016. Zenefits was maybe less of a compound startup than Rippling was, and Rippling is more of a compound startup. I think that today, and I don't know like the exact sort of math equation here, but we can build software at something like 10 times faster than we could just a few years ago. If that is true today, that is going to be true a few years from now, where we can build software 10 times faster than we can today. And so we want to go after as much sort of breadth of what we can do in the platform with the assumption that AI is going to enable us to build a product far faster. And that is what customers want.

• 37:34Speaker 00

  Customers want to come to one platform. The outcomes are actually better because you don't have data in a bunch of different silos. The system of record, the thing that does your call recording, the thing that does your outbound, the thing that builds your database. It is far more difficult to overlay an agent on top of this arbitrary set of tools with data silos than it is a single platform and source of truth that both has all of your data, but also takes all of your actions inside of the same tool.

• 37:58Speaker 01

  Totally. So when you think about what you're selling to customers, in some sense, I guess, you're kind of selling well-wrapped tokens that can do all these different things, but you're kind of selling intelligence to the customer at the end of the day. So have you thought about like, you know, or I know you have, how have you thought about what this means in terms of the way you price, the long-term of what your cost structure is going to be, and like what that all looks like from an economics perspective? Because it's obviously very different than build software and, you know, sell it for, you know, per user per month kind of situation.

• 38:29Speaker 00

  For sure, yeah. Well, two things come to mind. One is Monaco and we at Monaco are very opinionated. I think that there are certain applications of AI and maybe applied to different functions, where it's largely like ones and zeros. And what I mean by that is like, support is close to this, where you're like driving towards an outcome, which is a resolution to somebody's support ticket.

• 38:54Speaker 01

  Right.

• 38:55Speaker 00

  It's even more pronounced, I think, in the world of like finance and accounting, where there is like an actual number, that there is like a real 1-0 type number that is the calculation of everything that comes before it.

• 39:07Speaker 01

  Yep.

• 39:08Speaker 00

  I think sales is like. We start with finance, we move to support, we progress to sales. There's like far more subjectivity that goes into sales than there is this sort of like

• 39:21Speaker 00

  black and white, binary outcome that is true in the world of finance. And so we are very opinionated in things like, how do we determine which types of companies to reach out to and when to reach out to these companies? And what are the signals that we're leveraging? And how does that be incorporated into messaging? And these things that many of our customers today don't experience doing, right? And so then that is the first thing that comes to mind is like the opinionated nature of the product.

• 39:48Speaker 01

  And then meaning that you're helping. It's funny because as you were saying that I was like, I didn't know what you're talking about. You're talking about both. It's both about who you're reaching out to, but it's also then, you know, implied is who your customers ought to be reaching out to and all of that. You know, everything you're talking about is like, kind of like what you're selling to the customers.

• 40:03Speaker 00

  That well, we're certainly running on Monaco. And yes, I think customers hopefully benefit from the opinionated nature of the platform itself in ways that if you think about our customer, most of them are startups, seed, series A. They don't, as founders, oftentimes have sort of deep go to market experience. And so we can take much of the sort of like decisions and strategy, which is a word that I don't hate, but I don't like, but I can't think of a better one right now. Sort of off of their plate. And then we enable them to do the things that are super high leverage on their time. Things like meeting with customers, coming up with creative campaigns that today AI is less good at. But if you think about the workflows that I just described, building a database, overlaying signals,

• 40:47Speaker 00

  finding buyers, coming up with messaging, these are things that Monaco is certainly better than me at. And arguably better than just humans. And so then you can sort of outsource this thing to free up your time to do the highest ROI use of your time in a sort of like world of go to market, which is like customer facing. And then you asked a question on pricing. We are, our pricing is correlated towards outcomes. Outcomes are relatively objective when it comes to Monaco. Now, like the ultimate outcome, or excuse me, outcomes are relatively objective. And it comes to the category of like go to market or sales. It's revenue. How much revenue are you generating?

• 41:24Speaker 01

  Yep.

• 41:25Speaker 00

  There are some inputs. These are things like meetings and conversion rates. And so we rigorously track towards the ultimate outcome of revenue. The inputs of are we generating meetings? Are we improving conversion rates? And our pricing is aligned with how much a customer is using the platform. And that should be highly correlated with the impact or benefit that a customer is receiving from the platform. That is like fairly easily measurable.

• 41:55Speaker 01

  So I would love to unpack kind of the go to market strategy you've had so far. You launched like February, so I guess call it four, five months ago. And we talked about this with Brex, but definitely like you flipped a bit and like everything, everything was loud. So like what I'm curious about is can you sort of share what was in your head when you were like, okay, it's time to launch. We're going to be loud. Here's the things we're going to do to sort of like get this whole brand going.

• 42:20Speaker 00

  Yes. I think I'll describe our approach. It was the right approach for us. Also sort of caveat with a couple of things that I think are worth calling out that maybe like advantages that we have as a business that don't necessarily apply to every startup. We wanted to take the approach of operating in stealth through this like design customer phase. And then have a big sort of shotgun style launch, which we did back in February, where we went from almost a definitionally unknown company. Nobody had LinkedIn Monaco up. Our website said coming soon or some version of that. And we certainly spent $0 on marketing up until the day that we launched.

• 43:05Speaker 00

  And the like reason that we wanted to take that approach is, again, I haven't come up with a better analogy for it than this, which is like the boiling frog thing, where you can imagine if you are the frog and like you're in the pot and like the water is heating up and you like, don't totally notice it. Well, we can apply that to like, if you do marketing campaigns over a two year period. And you like, as a consumer, you may see like bits and pieces of somebody's marketing campaign here and there. And like, yeah, I've maybe heard of this company, but like I heard about them a long time ago and they like did this thing. You can imagine the sort of like psychological impact of that relative to like the dropping the frog in the boiling water, which is like, oh my gosh, we are seeing Monaco everywhere all of a sudden.

• 43:48Speaker 00

  Like I see the plane and I see the billboards and I see the poker tournament.

• 43:51Speaker 01

  Your, your, your, your plan and your billboard gave no explanation of what Monaco was. Like it just said Monaco and then like the billboards had like a big dollar sign, which I thought was hilarious and I loved it, but like you didn't say, you know, new AI sales platform. You know, you, you just were like Monaco.

• 44:06Speaker 00

  Yeah, we benefit from having a geographically concentrated target market. So we're selling to startups. You and I are sitting here in San Francisco. Many of our customers are also in San Francisco. So if we were selling to HVAC companies, we shouldn't be flying planes around San Francisco or putting billboards up around San Francisco because they're like fairly well distributed and not highly concentrated. So there are like maybe two aspects that we were deliberate about solving for. One is brand awareness. That's the plane, that's the billboards and, and more. When we do think that there may be like two impacts of brand awareness. The first is we do a lot of outbound. Monaco does our outbound for us. When we reach out to a company that is graduating YC, reach out to the founder.

• 44:51Speaker 00

  They receive the message from me. They have heard of Monaco because they've seen the plan, whatever like the thing is. The likelihood that they respond to that outbound message is exponentially higher than if they didn't know me, if they didn't know the business. So like the brand awareness is something that we're very deliberate about. There's a second application of that, which is when they take the meeting, they are far more likely to convert because there is comfort in like knowing and understanding a brand like the one that we are hopefully creating around ourselves in ways that maybe other folks aren't deliberate about and haven't created for themselves. The other type of marketing that we're delivered about is like demand gen. This is very targeted.

• 45:32Speaker 00

  This is sending people the poker sets that we send to founders when they graduate YC or something like this. And hosting the poker tournaments and inviting specific founders to that poker tournament with the expectation that that specific founder is going to be somebody that we convert. So we solve for both.

• 45:51Speaker 00

  I can talk about maybe like a couple of marketing principles that are things that we apply to.

• 45:59Speaker 01

  Yeah, that would be great. I would love that because you know, like one of the things I often think, I don't think this applies to every startup, obviously, or I know it doesn't apply to every startup. I think there are many startups that could be investing much harder in their brand that, that don't. And it's hard because it's like, well, if I do this demand gen campaign, it turns into revenue. And if I do this brand thing, or you know, I spend this money on these sort of like brand campaigns. It's like not going to show up. So it's hard to, but it just seems like a missed opportunity for so many people.

• 46:26Speaker 00

  Yes, I, I think everyone should do this in their own specific approach. What Monaco is doing isn't relevant to most startups. We can do it because we sell to startups, the geographic concentration. Again, most.

• 46:41Speaker 01

  But there's a version of it for almost.

• 46:43Speaker 00

  There's a version of it for everybody. I think there's a process that every company should follow. And, and then I can talk about like maybe, maybe a couple of principles in case they're helpful. There is a process which like most companies do not follow. You've got to try stuff like, like you just have to just do stuff and you can't be afraid to fail. And I do think that most companies here, they, they just don't really do anything.

• 47:09Speaker 01

  I, I do think that on this point, it's a lot of people are afraid of the embarrassment of, you know, a brand campaign that failed or some marketing or sales effort that just like looked stupid and didn't land. And that's actually, that is a, that's psychologically harder than just like building product or doing other things that are not publicly embarrassing.

• 47:30Speaker 00

  I think there are two things. I think there's one thing that is like, I'm not good at this. So I'm an engineer, not me personally, I'm saying like, putting myself in shoes as a founder. I'm an engineer, I build product. I like, I'm going to index on the thing that I'm very good at. I don't know how to do like a marketing campaign.

• 47:46Speaker 01

  Which is funny, you know, our CTO at my co-founder, Eric at Lattice, came up with by far our best billboard, which was like investing your people, not crypto during 2019. And that just like landed super hard and that engineer.

• 47:58Speaker 00

  Yeah. So I'm not, I'm bad at this, so I'm not experienced this or whatever. I don't want to spend the money. I'm worried about like, you know, lighting the money on fire or something like that. I think those are the two variables that probably lead more towards stagnation or just like lack of effort in this category. The reality is like, no one starts being an expert at this stuff. You've just got to like try stuff and learn. And I actually spend a lot of time with our customers doing exactly this. Like my time, I spend customer facing all day. Let's come up with some cool campaigns that we can run for your business and just ideating on this. And I think that's hopefully high ROI to our customers.

• 48:37Speaker 00

  And you can do inexpensive campaigns. Like one, you don't have to be an expert at this. Two, there are campaigns that are inexpensive. I'll give an example, these like poker sets that we send to founders that say Monaco Casino, they're on brand that are prefab because Monaco has a casino, they're like a hundred and ten bucks. You can do a test, send this to 50 people, you're spending $5,000. It's like, no, like if you were truly bootstrapped and have like, you know, no dollars to spend. Sure, you can't do the like $5,000.

• 49:06Speaker 01

  But you can still do stuff. There's always stuff.

• 49:08Speaker 00

  There's always stuff you can do and you don't have to break the bank to do it. So you run a process. Here's what we do internally in case it's helpful for others. We run a process at least once a month. We want to have like a big splashy marketing campaign that we are trying, get a handful of people in the company. Define them as like the marketing committee or whatever it is. They don't have to be marketing folks. It can just be you and your co-founder if you're just two people. Come up with a few ideas, put them on the whiteboard and just do it. Just like jump, don't be afraid to fail. Try something. If it doesn't work, chalk it up as a win because you learned and you're going to try something new that is going to be more effective or something like that. But you do want to have like a bit of process around this where every single month you're trying at least one or two different things.

• 49:52Speaker 00

  That are in this like category of marketing, brand awareness, demand gen, however we want to frame it. And I think we really want to be contrarian is maybe like not the right application of that word, but we do want to be creative.

• 50:04Speaker 01

  Do new stuff.

• 50:05Speaker 00

  New stuff.

• 50:05Speaker 01

  Like your plane.

• 50:06Speaker 00

  The plane.

• 50:07Speaker 01

  Was awesome. Can you talk about the plane?

• 50:09Speaker 00

  Yes.

• 50:09Speaker 01

  I feel like there might be one flying right, right now.

• 50:12Speaker 00

  We, um, there, there, there isn't. We took it down. We'll put it back up at some point. I think like probably reached diminishing returns or something over time.

• 50:19Speaker 01

  But it was like, yeah, anyway, go, go ahead.

• 50:21Speaker 00

  We, we were at Saster, which is Jason Loomkin's conference, it's awesome conference. And we knew that there would be like a large contingency or concentration of people at this event down in San Mateo. And so we, we, we didn't think this was like that creative. In fact, it wasn't that creative in that there was at least one, maybe two other planes flying at the same event. And so we had the banner trailing the Monaco plane at this conference. I don't know what we paid. Let's call it like a couple thousand bucks to make the banner. And then I was surprised at how relatively inexpensive putting this plane in the air for many hours during the conference was, which is like 6,000 bucks a day. And you know, we do it for two or three days at a conference. And I was just sort of thinking like, we already have the banner.

• 51:07Speaker 00

  We already know like the cost of flying this thing. Do you guys like, I haven't really seen these in like San Francisco proper. Do you guys, can you guys fly over the city? And part of my assumption was like there are air restrictions that like you couldn't fly in and around the city or whatever. And they were like, yeah, we can totally do it. And so I was like, you know, starting to do the math on this thing and it was like 6,000 bucks a day. Pay for 10 days, 60 grand. We have a lot of billboards. Some of our billboards are significantly more expensive than 60 grand. This is one of those that's like, it's a $60,000 learning. Like, like the worst case scenario, we fly this thing around.

• 51:48Speaker 00

  It doesn't totally work. We like learn from it and we don't do it again. It worked. So we, you know, both like messages on my phone. People posting on LinkedIn and Twitter and everywhere else. It was, it was, it was sort of everywhere. And so we kept it up for a little bit longer. And so it was one of those things that was like just an evolution of something that we had tried at the conference. Let's like try it in the city. It worked in the city. We learned from it. We'll put it up again when we do a big like announcement that we have coming up. Yeah.

• 52:16Speaker 01

  You know, it's interesting, like history kind of, I'm sure you've read Behind the Cloud, the, you know, the, the early Salesforce book from Benioff. And like, one, one of the things that like struck me was like, early Salesforce did a lot of really creative marketing.

• 52:27Speaker 00

  They did.

• 52:28Speaker 01

  Really creative. And like some of it was that the message was creative, like the no software thing. It's like, well, you know, that's interesting. You know, there was a lot there and just like the way they even did like customer dinners, you know, I think was like kind of creative and you know, it's like all became sort of like tried at some point. But like being the first to do a good go to market idea is worth a lot, it seems like.

• 52:46Speaker 00

  I think there, um, the one that I understand as much as any was like the protest. It may be like a big Siebel or Oracle conference where it was like the no software. Which I think was really smart.

• 52:57Speaker 01

  Yep. So like when you're thinking about this, are you, are you like, I'm going to do new activities? And then I'm going to put them on some back burner or you like, I just have to always be like, do these things stack and build over time? Or are you just like, I gotta always have a new thing?

• 53:11Speaker 00

  There are two things that I am thinking about, which maybe like go back to, I said, maybe some marketing principles that we try and apply. That I think my guidance to any customer that I'm working with is like, you should try and apply the same logic as well. The, the first is if you think about marketing spend as a category, you can sort of separate it into two buckets for the purposes of this first illustration. Then we'll do it separately for the second illustration. The first is like third party advertisers. And the first is like, and the second is like creativity. The first is like, it's oftentimes lower friction to do. It's mostly paid online advertising.

• 53:52Speaker 00

  I, I think if we looked at maybe like series C plus technology startups, where is most of their marketing spend going? Is likely going to third party advertisers. And I surmise like at the top of that list is probably like the Googles, Metas, Linkedins of the world where it's paid online advertising. Maybe they're doing some like offline, out of home type stuff. This is like easy, low friction marketing spend and it is easy to do. It's not creative. Everyone is doing it. It works. It's also like the, the lowest ROI. It's like a fairly efficient market at this point.

• 54:24Speaker 01

  Yes.

• 54:25Speaker 00

  You, you want to be spending, especially at the early stage, you want to be spending more of your marketing dollars on creative campaigns. That aren't going to third party advertisers, that are these like, what can we do that are different than anybody else is doing? The categories here are going to be things like gifting and events and you know, I'd even put the plane in that category. It's the things that like no one else is doing and you want to try. They oftentimes require more operational complexity. Then do the like efficient market paid advertising, marketing spend where most of our marketing dollars collectively are going.

• 55:04Speaker 00

  So that's like maybe a principle, be creative, try new things, allocate some percentage of our spend towards that category. The second one, and I don't know that like either is more influential or important, but they're sort of related. The second one is like the vast majority of marketing dollars go to third party advertisers that in no way benefit the person or company that we are targeting to try and acquire as a customer. So these go to, and we do this too, by the way. So these go to the billboard companies, the, the clear channels and out fronts of the world that we are paying to put ads up around San Francisco.

• 55:46Speaker 00

  These go to, as I referenced, the Googles, the Metas, the Linkedins, those sorts of things that are online paid advertising. Very little marketing spend directly benefits the person that we are targeting to try and acquire as a customer. Early on, I would try and bucket like a hundred percent of the marketing spend actually to something that benefits the person that we are targeting. And if you put yourself in the shoes of a prospective customer, you are a, well, let's take Monaco as an example. You are a YC founder.

• 56:17Speaker 01

  Yep.

• 56:18Speaker 00

  Would you rather have Monaco or any company that is trying to acquire you as a customer? Spend money on like LinkedIn ads that follow me around, that like message something to me that I sort of scroll past and then billboards and whatever else the spend is going towards. Or would you rather have Monaco send me a like poker set?

• 56:38Speaker 01

  Some like heavy clay poker chip?

• 56:39Speaker 00

  Totally. Exactly. Like that I, founders play poker, that like we can use for our poker night as a company. Would you rather throw like a poker tournament? We had, we give away a hundred thousand dollars, Monaco Invitational, you were there.

• 56:52Speaker 01

  Number, yeah.

• 56:54Speaker 00

  The final table gets all of it.

• 56:55Speaker 01

  Yeah.

• 56:56Speaker 00

  Let's say there are a hundred people that start playing. We, we end with nine at the final table. Eight of the nine finalists that received wires from Monaco were Monaco customers. Would you rather have Monaco as a customer of Monaco or somebody who you might, who might be using Monaco? Would you rather have us throw this poker tournament that you come to have?

• 57:13Speaker 01

  Yeah.

• 57:14Speaker 00

  Hopefully a blast.

• 57:14Speaker 01

  Yeah.

• 57:15Speaker 00

  Make like a bunch of money at the final table. Or again, like pay Google.

• 57:18Speaker 01

  Right.

• 57:18Speaker 00

  For like the SEM, whatever stuff that's like following me around when I go to different, either websites or, or Google searches. So, um, uh, use that as like a bit of a thought exercise. Allocate your marketing dollars. Do it otherwise be going towards very expensive and efficient markets around this paid advertising. Do things that benefit the customer directly. We take it a step further. We spend a lot of money on customer marketing. And so what we want to create is like a bit of a, a Monaco community through our customer base. But the, the like, the most effective marketing spend that we have.

• 57:56Speaker 00

  And when I like approve this going out, it, it is like my favorite bill to approve of literally any bill that I approve at the company is the like referral. It, it is the like customer referral where we are paying somebody $2,000 because they told their friend that they love Monaco, that friend should check us out, that friend signs up.

• 58:17Speaker 01

  Yes.

• 58:17Speaker 00

  And look, if we're doing a couple of grand a month, um, we're paying people like $10,000 to send us. It's like the, the highest ROI use of what is effectively a marketing spend.

• 58:26Speaker 01

  Yeah.

• 58:26Speaker 00

  Right. That is a customer acquisition cost.

• 58:28Speaker 01

  That's right. Yeah, that's awesome. So, um, when we, uh, so I mean, I guess thi- this is the like kind of air cover. And then the other half, I guess of early startup go to market is like the ground game. And, uh, maybe just to wrap, you know, uh, this conversation. Can you talk about you're sitting like, that was like a very good illustration to me of like, if I'm like a Monaco customer, like, and I'm meeting with you, like, I can now like immediately imagine how I'm going and thinking about doing, doing that. The ground game side where I'm like, okay, now I also need to do the sales calls and build the early machine. And I'm like a series A or late seed stage founder with early go to market. But I've got like, you know, a handful of reps or two reps or 10 reps or whatever.

• 59:08Speaker 01

  What are like the principles you're teaching me or talking to me about as, you know, uh, you know, a sales org, you know, builder?

• 59:15Speaker 00

  Yeah. Well, first, maybe, um, in, in a more, we, we've already used this word in a different context and more like meta level. I, I, I think that there's, there's something that, um, it is worth maybe touching on. It is like, how should we be applying AI to go to market? And then what does that give us leverage to like focus our actual time and energy on, which is the thing that you just talked about. Backward looking, uh, I, I think most labor, um, i- i- in the sort of like category of startup go to market was on what I would describe as workflows that today AI is actually better at doing. This is like building your TAM, scoring your accounts, overlaying signals, finding buyers, writing messaging.

• 59:57Speaker 00

  All of this like fully online workflow orchestration.

• 1:00:02Speaker 01

  Yeah.

• 1:00:02Speaker 00

  That agents are just better than any human in the world at. And so it is, it is true that that is like what Monaco does for you. All of this sort of like, um, non customer facing, sales related activities, building your database, scoring your accounts, finding leads, engaging with buyers after you finish a meeting, updating your pipeline, reminding you who you need to reach out to. All of these things and what that does, whether it's Monaco or not, it allows you to spend your time on higher ROI, higher leverage activities. I think there are two categories. One is, and this is the thing that I spend all of my time doing, but it is, um, meeting with customers. Today, uh, especially if you were in like B to B, uh, buyers still want to talk to a person.

• 1:00:47Speaker 00

  They don't want to, um, buy from an agent, a like, you know, Jack Altman avatar that shows up to a call that is like not really Jack. Um, so, uh, uh, there's no higher ROI on my time, maybe on, uh, uh, I would suspect our customers' time than, um, spending time with customers. And a lot of the things that we're able to leverage with AI, um, allow us to spend far more of our time, whether you're a founder or a salesperson on that, um, human connection, developing relationships, customer facing. I think the second thing is this category of, um, creative, operationally complex campaigns. We've talked about a bunch of them.

• 1:01:26Speaker 00

  You could do like a chat GPT conversation where you're like, can you come up with some marketing ideas for me? I think it would be hard for that to result in the plane as an example. I, I, I think that today AI will sort of pattern match to things that have already been done because that is what AI is trained on. And so if you're trying to do something like truly creative, innovative, innovative, I think it, it is more likely to, um, surface inside the four walls of your company by doing the sort of like ideation that I talked about, which is, um, let's come up with two ideas. Each person multiply by four, that's eight ideas.

• 1:02:09Speaker 00

  Put them on a whiteboard, talk through each of them, pick the two or three, the best ones that we're going to do. And, and Monaco and AI actually give us the like ability to spend our time doing those things. That is how I spend my time with customers. It is, is the, less about the sort of like, how should you be meeting with customers? I do like, how should you sell those sorts of things? But it's coming up with like creative campaign ideas. Count me in as like one of the people that comes up with the ideas that we put on the whiteboard.

• 1:02:37Speaker 01

  Yeah, that's awesome. And then I guess like on that last piece, is there anything, um, worth talking about in terms of like how to actually sell or like the, the practice of, you know, the, the time with the customers itself?

• 1:02:51Speaker 00

  I think there are two things that, um, stand out as the, cause, cause, and then there's like a laundry list below it, right? But this is maybe the like broader generic advice that I would have to certainly founders that are, are starting to sell their, um, product and don't have a lot of go to market experience that I think have maybe, um, more impact than any other, you know, below these two. The first is, um, I would be fairly prescriptive about how to effectively buy your product. Because i- i- if you aren't educating the buyer on how to onboard, receive value and ultimately buy your product. The customer like doesn't know how to buy your product. And so I would come in with like a bit of a, um, but combination of like a, a, agenda and opinion.

• 1:03:36Speaker 00

  On here is the like happy path from where we sit today. And if this resonates with you and is something that you think you can receive value, um, around to like where we are when you are fully onboarded and receiving value from the product. And we can just sort of roadmap together. Here are the different steps. Now, like Mr. Customer, is there anything that I have left out of this process that is important to you that we should incorporate? Whether it's like security checks that you may need to go through or procurement that we want to introduce or legal review that I haven't included. But we sort of start with, um, and this is very abstract. We sort of start with like, um, we, you know, meeting two, we come with like our, um, pre-built custom environment to show you exactly what it would look like on our product.

• 1:04:21Speaker 00

  If that resonates with you, we sit, we put you in like a, a two week free trial of the product. During that trial, like here are the outcomes that we're going to be driving towards. If we deliver on these outcomes, we like onboard the rest of the team. Let's like schedule meetings that sort of align to these different steps. And so then you and the customer aren't flying blind. I think the thing that happens more often than anything when I meet with founders, it's sort of like, we have so many of these opportunities that are in like purgatory. Where it's like, we pitched them, they said they liked it. We ended the call, I followed up three times. They aren't really responding. And if they do respond, it's like, give me a week and I'll get back to you. A week passes, they don't get back to me.

• 1:05:04Speaker 00

  And it's because we haven't like aligned on the like happy path to receiving value from the product that we're selling. So I'll pause there. That's like one of the two things.

• 1:05:13Speaker 01

  Yeah. Yeah. Yeah. What's the other?

• 1:05:14Speaker 00

  The, the, the second thing is like, um, a, a little bit of an urgency driver, uh, where, um, i- i- if you can create some form of FOMO, for lack of a better word. I, I think that much of sales is psychology. And so for many customers, um, what I'm about to articulate is true. We certainly never want to say anything that is untrue or misleading. But if we have, you know, we're in the month of July. If we have a goal to, um, onboard three customers to pilots in the month of July. What we articulate to, uh, a customer as part of the, maybe like first call when we are receiving feedback, like, yeah, this is actually really cool. I'd love to try it.

• 1:05:55Speaker 00

  What we say is something like, um, we are onboarding three customers into our pilot program this month. Two of those spots are already spoken for. There is much interest in the third spot. If you would like to move forward with a pilot, if you could let me know, that would be like really appreciated on my end. But also like, I, I can't guarantee the spot if you don't speak for it today.

• 1:06:18Speaker 01

  Yeah.

• 1:06:19Speaker 00

  And I think.

• 1:06:19Speaker 01

  And I mean, in your case, that's true because you can only onboard so many at this stage.

• 1:06:22Speaker 00

  That's exactly right.

• 1:06:23Speaker 01

  Yeah.

• 1:06:23Speaker 00

  Um, but it, it does, um, sort of force a decision.

• 1:06:27Speaker 01

  Yeah.

• 1:06:27Speaker 00

  And potentially drive some urgency.

• 1:06:29Speaker 01

  Yeah.

• 1:06:29Speaker 00

  Um, there is like a psychological aspect to this where it's like, oh gosh, two, two thirds of the, the, um, spots are already spoken for. Like I better speak up, um, to, to like, you know, get this thing that a lot of folks are already incredibly interested in.

• 1:06:42Speaker 01

  I assume also important in all of this is sort of just like having like a, a willingness to disqualify when you genuinely think that the product is not going to help the customer. And I think people can feel that, like, if you're like, hey, my goal here is not to sell you something that you don't need or want. My goal is to sell you something that's going to be useful to you for years. And so if I don't think that that's going to be the case, I'm going to stop selling it to you.

• 1:07:03Speaker 00

  Man, when you say that, it, it, it's interesting where my mind goes, which is something different than what you just said. But like, I think it is true that like growth solves a lot of problems. I, I think like, um, uh, in, in input to that is something like demand solves a lot of problems. And what you just articulated, I think is a symptom of not enough demand, which is where, um, founders and salespeople are like hanging on for dear life to the like one guy that I pitched over the last couple of days. Because like they kind of seemed interested.

• 1:07:33Speaker 01

  But if you're like, I've got like four more calls I should get to, and like, I think this is going to be painful. And by the way, I get paid also on you retaining. And so like, I don't think I want to sell this to you anymore.

• 1:07:42Speaker 00

  You can, um, Parker, uh, I, I stole this from him. You, you, you can sort of swipe left.

• 1:07:50Speaker 00

  I've never been on one of the dating apps, but I think Tinder, you, you sort of like swipe right if you like them and swipe left if you don't. Um, and so, uh, uh,

• 1:07:58Speaker 01

  An abundant pipeline allows you to only try to sell the product to people who need it.

• 1:08:02Speaker 00

  That, that's exactly right. And it's, it's not, it, when I say that, it, it's not like disrespectful to the customer or being inefficient about not following up.

• 1:08:11Speaker 01

  Yeah.

• 1:08:11Speaker 00

  It, it's actually that like you are focusing your resources on the people that are truly interested that will receive the most value from the product and not on the like person that took a call that was like, said a lot of niceties.

• 1:08:24Speaker 01

  Yeah.

• 1:08:24Speaker 00

  But, but like actually probably isn't actually interested.

• 1:08:27Speaker 01

  And by the way, a lot of it is like a not now, but you know, let's come back to this. If you're like.

• 1:08:30Speaker 00

  Oh, we have so many customers.

• 1:08:31Speaker 01

  If you're like, if, if it's somebody who's like, you know, I am just getting started. I don't really have product market fit yet. I don't have any reps. You know, I'm interested. You might be like, if you bet, like, sure, if you want to buy it now, but like, it might be better if you bought this in six months, once you're going a little bit.

• 1:08:44Speaker 00

  We're, we're four months in, um, four, five months in, uh, launched in February.

• 1:08:49Speaker 01

  Yeah.

• 1:08:49Speaker 00

  And, um, Monaco does an awesome job, uh, of continuing to engage with older customers on our behalf.

• 1:08:58Speaker 01

  Yeah.

• 1:08:59Speaker 00

  Um, but I cannot tell you, well, I can tell you that the amount of times where, um, I'm just sitting there and resurrected from what effectively is the dead, a company that we demoed back in February that Monaco sort of re-engages with on my behalf. Response comes in, I see the response and it's like, I'm ready to go.

• 1:09:16Speaker 01

  Yeah.

• 1:09:16Speaker 00

  Um, and again, all of this stems from more demos in February, right? Um, and so, uh, uh, I, I think lots of sort of, um, uh, anecdotes of what a demand-rich environment, um, uh, evolves still.

• 1:09:30Speaker 01

  Sam, this was awesome. I learn a bunch every time we talk. Thank you for doing this with me.

• 1:09:34Speaker 00

  You are the best. Thank you so much for partnering with me on Monaco. And, uh, it's just an absolute pleasure to come on the show. So thanks for having me.