# Sam Blond on the Future of Sales in an AI-Native World | Ep. 54 Markdown copy of https://realalpha.app/v/QnkQhyOGo3k/ on Real Alpha, the best minutes from long interviews with the people building AI. Cite and link the page, not this copy. Sam Blond argues that the next sales leader will be an AI-native platform that automates revenue work while keeping people focused on customers. - Show: Uncapped - Hosts: [Jack Altman](https://realalpha.app/people/jack-altman/) - Guest: [Sam Blond](https://realalpha.app/builders/sam-blond/) is cofounder and CEO of Monaco. - Published: Jul 14, 2026 - Length: 1 h 10 m ## The best minutes - [9:38](https://realalpha.app/v/QnkQhyOGo3k/?t=578) [Pipeline volume matters more than small conversion gains](https://realalpha.app/s/pipeline-volume-matters-more-than-small-conversion-gains/) (5 min) - [28:50](https://realalpha.app/v/QnkQhyOGo3k/?t=1730) [Salesforce is constrained by its pre-AI architecture](https://realalpha.app/s/salesforce-is-constrained-by-its-pre-ai-architecture/) (3 min) - [1:02:35](https://realalpha.app/v/QnkQhyOGo3k/?t=3755) [Give buyers a clear path to getting value](https://realalpha.app/s/give-buyers-a-clear-path-to-getting-value/) (4 min) ## Also worth watching - [6:41](https://realalpha.app/v/QnkQhyOGo3k/?t=401) [Zenefits reset its target after modeling a $20M year](https://realalpha.app/s/zenefits-reset-its-target-after-modeling-a-20m-year/) (3 min) - [14:07](https://realalpha.app/v/QnkQhyOGo3k/?t=847) [Brex grew through strong hires, broad awareness and better targeting](https://realalpha.app/s/brex-grew-through-strong-hires-broad-awareness-and-better/) (5 min) - [32:03](https://realalpha.app/v/QnkQhyOGo3k/?t=1923) [Falling software costs push Monaco toward a broader platform](https://realalpha.app/s/falling-software-costs-push-monaco-toward-a-broader-platform/) (6 min) - [42:11](https://realalpha.app/v/QnkQhyOGo3k/?t=2531) [A launch burst can make outbound feel familiar](https://realalpha.app/s/a-launch-burst-can-make-outbound-feel-familiar/) (4 min) - [52:59](https://realalpha.app/v/QnkQhyOGo3k/?t=3179) [Early marketing spend should benefit prospective customers](https://realalpha.app/s/early-marketing-spend-should-benefit-prospective-customers/) (6 min) Skip the career chronology and Founders Fund story, followed by the competitive-market discussion and product-pricing overview. ## Full analysis: Sam Blond says doubling leads can beat a 10% to 20% conversion push - For large markets, Blond said doubling leads can be easier than moving conversion from 10% to 20%. - But Zenefits showed that raw opportunity counts can reward low-quality leads. - Track closed revenue per rep, lead quality and time returned by automation. Its 6 sections, what it means for you and what to watch are on [the page](https://realalpha.app/v/QnkQhyOGo3k/#analysis), free with an account: - [12:13](https://realalpha.app/v/QnkQhyOGo3k/?t=733) More pipeline can beat a higher close rate - [29:42](https://realalpha.app/v/QnkQhyOGo3k/?t=1782) Incumbents face an architecture test, not an AI demo - [35:46](https://realalpha.app/v/QnkQhyOGo3k/?t=2146) Owning the record raises both upside and burden - [42:47](https://realalpha.app/v/QnkQhyOGo3k/?t=2567) Creative marketing earns attention, but attribution stays thin - [1:00:41](https://realalpha.app/v/QnkQhyOGo3k/?t=3641) Automation should return time to people, not remove them - [1:03:16](https://realalpha.app/v/QnkQhyOGo3k/?t=3796) Mapped buying steps turn interest into a real decision ## Summary Sam Blond is the cofounder and CEO of Monaco, an AI-native revenue automation platform built to replace the CRM as sales’ system of record. Before Monaco, he was a Partner at Founders Fund and held sales leadership roles at EchoSign, Zenefits and Brex. Blond argues that AI creates an opening for a new sales platform built around revenue outcomes, rather than adding AI to an older CRM architecture. He says many founders misdiagnose revenue shortfalls as conversion problems when they need more qualified pipeline, and he favors growing volume while tracking closed revenue. He sees AI automating sales workflows so founders and reps can spend more time with customers and on creative campaigns. He also shares Monaco’s launch and pricing approach, along with advice for structuring sales processes and qualifying buyers. ### Minute by minute - [0:49](https://realalpha.app/v/QnkQhyOGo3k/?t=49) **Company quality compounds early.** Blond traces his sales career from EchoSign, where he started as an SDR and moved into senior sales roles, to Zenefits and Brex. He says joining a strong company at an inflection point can matter more to a career than title or compensation, and that sales was a good fit for him. - [5:27](https://realalpha.app/v/QnkQhyOGo3k/?t=327) **Ambitious goals create urgency.** At Zenefits, Blond says the 2014 plan called for growing from near zero to $10 million in ARR, then Parker asked the team to model what it would take to reach $20 million. The team later adopted the higher goal. Blond says this kind of exercise can expose what needs to change and manufacture urgency. - [9:38](https://realalpha.app/v/QnkQhyOGo3k/?t=578) **Pipeline beats conversion gains.** Blond says founders often blame missed targets on a deal slipping when they should ask whether they had enough deals in the pipeline. For companies with a large addressable market, he argues, doubling leads can be easier than doubling a 10% conversion rate to 20%. He prioritizes revenue closed over a rep’s close rate. - [14:07](https://realalpha.app/v/QnkQhyOGo3k/?t=847) **Strong teams and brand drive GTM.** Blond credits go-to-market results at Zenefits, Brex and Monaco to strong teams, and says he brought EchoSign colleagues Matt Plank and Jameson Young to Zenefits. At Brex, he says, loud campaigns aimed to make the company familiar to nearly all of its target market. He also says Brex invested early in revenue operations to identify which companies and buyers were most likely to convert. - [20:57](https://realalpha.app/v/QnkQhyOGo3k/?t=1257) **Founders Fund led back to building.** After Brex, Blond says he felt satisfied with what he had accomplished in sales and wanted a new challenge, so he joined Founders Fund in 2022. He gravitated toward incubating companies and co-incubated Monaco with his brother. Blond says building Monaco proved a better fit than working as a venture investor. - [27:47](https://realalpha.app/v/QnkQhyOGo3k/?t=1667) **AI creates an opening for a new leader.** Blond argues that Salesforce faces an innovator’s dilemma because its platform was built before AI, while Monaco is designed around AI from the start. He says Monaco can begin with startups, which account for less than 1% of Salesforce’s revenue, build a foothold there and later move upmarket. He expects the sales category leader to be built with AI in mind. - [31:19](https://realalpha.app/v/QnkQhyOGo3k/?t=1879) **Monaco wants the system of record.** Blond says Monaco chose to be a system of record because he sees the category evolving from a database CRM into a revenue automation platform focused on outcomes. He argues that point solutions have not produced the same kind of generational company outcomes as systems of record. He also wants Monaco to replace labor and multiple sales tools with one platform that shares data and takes action. - [37:49](https://realalpha.app/v/QnkQhyOGo3k/?t=2269) **Pricing follows platform usage.** Blond says sales involves more judgment than functions such as finance, so Monaco takes opinions on whom to contact, when to reach out and what to say. That can help startup founders who lack deep go-to-market experience. He says Monaco prices according to platform usage, which he expects to correlate with customer impact and revenue. - [41:38](https://realalpha.app/v/QnkQhyOGo3k/?t=2498) **A concentrated launch amplifies brand.** Blond says Monaco stayed in stealth through its design-customer phase, then launched broadly in February after spending nothing on marketing. Because its startup customers are concentrated in San Francisco, he says the campaign could make the brand visible through planes and billboards. He also distinguishes broad brand awareness from targeted efforts, such as reaching specific founders with gifts or events. - [49:33](https://realalpha.app/v/QnkQhyOGo3k/?t=2973) **Creative campaigns earn attention.** Blond says Monaco’s plane experiment cost about $6,000 a day, or $60,000 for 10 days, and generated enough attention to justify flying it longer. He recommends trying campaigns regularly rather than defaulting to paid advertising, and favors efforts that benefit prospective customers directly. He cites $110 poker sets and $2,000 customer referral payments as examples. - [58:24](https://realalpha.app/v/QnkQhyOGo3k/?t=3504) **AI frees time for human selling.** Blond says AI can handle tasks such as building a database, scoring accounts, finding buyers, writing messages and updating pipeline. That gives founders and salespeople more time for customer conversations and creative campaigns. He says B2B buyers still want to speak with a person, not an AI avatar. - [1:02:25](https://realalpha.app/v/QnkQhyOGo3k/?t=3745) **Give buyers a clear path.** Blond advises founders to lay out the steps from a demo to onboarding and value, then ask buyers to add any security, procurement or legal requirements. He says scheduled milestones keep opportunities from drifting after a promising meeting. He also recommends stating genuine limits on pilot capacity to help interested buyers make a decision. - [1:06:50](https://realalpha.app/v/QnkQhyOGo3k/?t=4010) **Abundant pipeline enables selectivity.** Blond says a strong pipeline lets founders stop pursuing buyers who are unlikely to benefit and focus on those who are a good fit. He says Monaco’s AI can re-engage old prospects, including companies that had seen a demo months earlier and later returned ready to buy. ## Transcript Uncapped, hosted by Jack Altman, with Sam Blond. Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there. [0:00](https://realalpha.app/v/QnkQhyOGo3k/?t=0) 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. Sam, what a delight to be here. I'm really excited to do this with you. 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. I'm going to try to live up to the hype of that. um so i actually first learned about you by reading jason lemkin's sastra blog back when i was you know starting lives 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 echo sign and he did all 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 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 yeah [1:05](https://realalpha.app/v/QnkQhyOGo3k/?t=65) we'll talk about lucking into some incredible company so uh jason and parker both of which you alluded to two of just like the greatest people but also um most influential people on the the career that i've had um and just like amazing advocates and close friends and all that stuff so shout out to those guys uh and um so let's see i 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 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 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. Crazy years there, which we can get [2:23](https://realalpha.app/v/QnkQhyOGo3k/?t=143) into. But like, I mean, what a growth trajectory that was. 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 Founders 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 zero dollars of revenue and then being able to leave when they were much, much larger and lots of revenue. Yeah. So we can spend the least time on this cause it's like reaching far back into the past, but like, what, 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, [3:27](https://realalpha.app/v/QnkQhyOGo3k/?t=207) what, what were your takeaways there? Yeah. Well, I think there was some, were you guys up against DocuSign? Yeah, that's right. So, um, DocuSign was a competitor. Um, EchoSign was private for like three or four of the years that I was there. And then Adobe had acquired us, EchoSign became Adobe Sign 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 Adobe Sign. 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... [4:00](https://realalpha.app/v/QnkQhyOGo3k/?t=240) 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 an SDR and then I was a sales rep and I was one of, let's call it like 10 growing into 40 salespeople. There's only so much that I can sort of attribute EchoSign's overall success to me. 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. It's arguably like we can, of course, 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 in 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 joined in a very early stage where you were like the first, the second, the [5:02](https://realalpha.app/v/QnkQhyOGo3k/?t=302) third, the fourth hire in, in the role or function that you were joining in. Um, and then the path dependency on the career from there just is like, so, so strong. That's exactly right. So, so Echo Sign, um, there, there was this thing that was largely outside of my control. Um, that was like the overall success of the business that influenced my personal success, uh, as much as anything, I think there is like a different variable here. 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. [5:45](https://realalpha.app/v/QnkQhyOGo3k/?t=345) I want to go to Zenefits. Parker, obviously one of the great founders of 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. 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. Can you talk about what building that go-to-market machine looked like in those early days? Yes. So let's see. We've talked about Parker a little bit. I think an inspiration in a couple of 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 [6:53](https://realalpha.app/v/QnkQhyOGo3k/?t=413) learn from. What's one that you like come back to a lot? 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, which by the way, in 2014, you know, now that people are like, but that's like, that's like today, somebody saying zero to a hundred. That was sort of unheard of. And Parker, um, let's see, uh, Parker as, as he should has sort of like very ambitious dream, big, uh, aspirations and expectations. Um, and so zero to 10 million was like, there weren't a lot of other startups that were doing it. Um, and so then early in the year of 2014, uh, we were trending towards more than that. Um, 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, um, stretch goal or however you want to frame it. What does it look like if we finish at 20. [8:02](https://realalpha.app/v/QnkQhyOGo3k/?t=482) 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 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. [8:16](https://realalpha.app/v/QnkQhyOGo3k/?t=496) **Sam Blond:** 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. [8:21](https://realalpha.app/v/QnkQhyOGo3k/?t=501) 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. 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 more achievement? Is that kind of it? 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. [8:55](https://realalpha.app/v/QnkQhyOGo3k/?t=535) And it can be something like a revenue target. It can 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 in those sorts of things? And so it's just operating rhythm of the business, something like that. 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? Well, I think one of the things that we benefited from quite strong product market fit at Zenefits. We benefited from the same at Echo Sign, 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 sort of misdiagnosed the opportunity to acquire customers and grow revenue more quickly as something related to conversion rates. [10:15](https://realalpha.app/v/QnkQhyOGo3k/?t=615) 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. Yeah. And if three of them close, you finish way over target. Yes. And if that one deal closes, you actually hit your target. [10:52](https://realalpha.app/v/QnkQhyOGo3k/?t=652) But in a lot of ways, like you could have done better. 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 that's right 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 a hundred 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. Uh, it's something that we, we have lived by and I think benefited from, uh, and, um, just to sort of like reinforce the thing that you just said, um, I would, well, um, if you have 10% conversion rates, uh, improving those conversion rates to 20%, which sounds like you're improving your conversion rates by 10%, but you're actually doubling conversion rates. [11:55](https://realalpha.app/v/QnkQhyOGo3k/?t=715) It's really hard. Uh, 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 intention. And if you do so, actually at the expense of either conversion rates or maybe like efficiency, that is a worthwhile tradeoff. [12:35](https://realalpha.app/v/QnkQhyOGo3k/?t=755) And so if you feel like... As long as like on a per rep basis, they're still closing enough per person per year kind of thing. As long as your growth trajectory is dramatically increasing month over month, if you have something... If you have the efficiency per rep, do you care about that? Or is that something that doesn't matter till later on? 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. [13:12](https://realalpha.app/v/QnkQhyOGo3k/?t=792) Just single our through, like focus on the throughput. The outcome. Yes. How much revenue did we close as a business this month? How much revenue did each sales rep close this month? Yes. 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 There aren't points for what your close rate was. Yeah, it's like, but you forgot to email this customer that otherwise could have closed like $200,000 of ARR close this month. [13:44](https://realalpha.app/v/QnkQhyOGo3k/?t=824) Like that is the thing that you see. And so like, of course, you want to focus. The details matter. And of course, you want to be constantly improving and giving feedback on all of those things. But solve for the outcome. 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 Ecosign experience. You've gotten the chance to be the leader from basically the get-go at this next company. And now you're doing it again with the lead seat and the experience. So now what happens at Brex? [14:23](https://realalpha.app/v/QnkQhyOGo3k/?t=863) 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. [14:55](https://realalpha.app/v/QnkQhyOGo3k/?t=895) Their names are Matt Plank and Jameson Young. Matt Plank is now the CRO at Rippling. Jameson 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 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 of these companies to the people that exist within the go to market organizations. I think the second thing we touched on is we don't have to go much deeper. [15:41](https://realalpha.app/v/QnkQhyOGo3k/?t=941) If you think about early days of Brex, 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. But you got really loud. I remember that. 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, you know who we are. And hopefully you have like some positive brand association with that. [16:30](https://realalpha.app/v/QnkQhyOGo3k/?t=990) So we're 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 it's benefits. We get something like a D plus 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. 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. [17:23](https://realalpha.app/v/QnkQhyOGo3k/?t=1043) 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, it 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 year of 2015, which was a more challenging year for Zenefits than certainly the 2014 year, I attribute a lot of that to the diminishing quality of leads and opportunities. And so the thing that we invested in early at Brex was really [18:07](https://realalpha.app/v/QnkQhyOGo3k/?t=1087) **Sam Blond:** understanding 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 [18:17](https://realalpha.app/v/QnkQhyOGo3k/?t=1097) 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 all the world. You get a leadership environment with the right type of people and companies that you're trying to sell to. 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 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. [18:54](https://realalpha.app/v/QnkQhyOGo3k/?t=1134) You know, like all good ideas have many, you know, 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? You know, it's interesting. Um, EchoSign was certainly competitive with DocuSign. And so I think lots of learnings in terms of, uh, how to compete through that experience. Brex evolved into being hyper-competitive. Yeah, but it started wide open. Interestingly, it was actually pretty greenfield, uh, when, when, for the majority of my time there. So my years at Brex were 2018 through like beginning of 2022. [19:29](https://realalpha.app/v/QnkQhyOGo3k/?t=1169) Uh, so 2018, 2019, even 2020, um, it was, um, mostly a one horse race. There was a company called Divi that was acquired by build.com a little later. So there were other players in the space, but Brexit was always like, um, the market leader. Um, and then I think dynamics of the market evolved, you know, starting in, let's call it 21, 21, and then certainly, uh, beyond. And I actually, what was, um, uh, not with the business, um, for, for much of that period of time. and then Uh, Peter has this, uh, uh, saying that's like fairly, Peter Thiel has a saying that's like fairly famous. Um, that I think like it is oftentimes to your point, hard to apply to enterprise software that is seemingly like inherently competitive. This competition is for losers. And, um, gosh, like, uh, uh, he, he's so, of course he's right because he's always right. But, um, you know, experiencing, uh, Brex in what I would describe, you know, I said, I said this, uh, term, uh, previously as, as greenfield environment, um, pretty smooth sailing. [20:29](https://realalpha.app/v/QnkQhyOGo3k/?t=1229) Yeah. Monaco today, we think of it as pretty greenfield. And so we are displacing incumbents, but aren't competitive today with many new entrants into the space. Yeah. 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. Yep. OK, I want to come to that before we do after. [21:10](https://realalpha.app/v/QnkQhyOGo3k/?t=1270) 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 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 yeah well look um i i've you and i have both talked about um jason and parker i'd be remiss if i didn't mention something about like the learnings from pedro enrique michael who is ceo now ceo at a company called figure um and so like equal sort of parts inspiration and then um uh 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, we're talking about Brian prior to starting the recording, but gosh, Peter, Brian, everyone is just like exceptional there. So let's see, I think I can get a little bit personal on like my mindset after Brex. So this is late 21, [22:29](https://realalpha.app/v/QnkQhyOGo3k/?t=1349) early 22. I'm reaching like my four year sort of tenure at Brex. COVID. It is COVID. I'm in Miami. Yeah. So I've moved to Miami at this point. And, you know, I just felt like for the first time in my career, I felt satisfied, which is very, it sounds positive. It's actually bad. 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. Just like definitionally, the probability of joining an earlier stage company that has a Brex-like outcome. [23:15](https://realalpha.app/v/QnkQhyOGo3k/?t=1395) You know, we were a $12.5 billion company when I left, which is like definitionally low. And it's like, even if you did, it's like, it was kind of the same, it was just a bigger number. I wasn't motivated 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 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 had seen him make this transition as, you know, like former sales leader. [23:46](https://realalpha.app/v/QnkQhyOGo3k/?t=1426) 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. world. I'd sort of be silly to not like take advantage of that. 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 anybody that's potentially listening to this. We weren't deploying a lot of capital at the time. This is like 22, 23. And 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 EchoSign and then beyond that I could just tell, like, this is a good fit. I don't know, certainly being in Miami, but I don't know that like being in VC 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 most famous of them with Palantir and then Trey with Andurl. And there's a bunch of folks that have Scott with [24:59](https://realalpha.app/v/QnkQhyOGo3k/?t=1499) General Matter and Dalian with Vard and more. 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. i asked you um the other day just like uh about like you know i don't even remember why but it was about like you know interest 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 um yeah was that like uh 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? Potentially unintentionally, meaning the take a breather. I think what you said is exactly correct. And 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. 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. Yeah, no, it was certainly a deliberate [26:15](https://realalpha.app/v/QnkQhyOGo3k/?t=1575) decision. I knew 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 correlated both with the place and the flexibility of the job or something like that. I was on the water a lot. There were plenty of hobbies that existed. And when I went all in on Monaco, I moved back to San Francisco. I live right by the office. It is, um, a high, high contrast chapter to chapter though. It is, it is, um, uh, uh, one 80 like, like, um, fairly STARK contrast. Uh, and again, it was deliberate and thus far I'm like very happy with the decision. I'm loving this. It's awesome. Okay. So let's talk about Monaco. So I guess, um, 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 a little self-evident, but like what was in your head where you're just like, you know, this is going to be what I'm going to do? 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 I started this company. It [27:28](https://realalpha.app/v/QnkQhyOGo3k/?t=1648) like was just pulling me and felt very much like this is so obviously what I should be doing in my calling. So I think part of it was just the fit for me. And I think maybe 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. things 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. [28:14](https://realalpha.app/v/QnkQhyOGo3k/?t=1694) 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 maybe we're students of history though or something and it's like you can see that basically it's like there are all these on-prem companies yes 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 in 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. [29:03](https://realalpha.app/v/QnkQhyOGo3k/?t=1743) 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, they're faced with an innovator's dilemma where they have an existing set of customers on a platform that was architected pre-AI. [29:52](https://realalpha.app/v/QnkQhyOGo3k/?t=1792) 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, [30:23](https://realalpha.app/v/QnkQhyOGo3k/?t=1823) **Sam Blond:** they are overlaying AI on top of a pre-AI system architected platform, which is better than no AI, but less good than being truly AI native, which is what a company like Monaco is. And so for us, [30:39](https://realalpha.app/v/QnkQhyOGo3k/?t=1839) 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 early stage technology startups? Less than 1%. 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 close to monopoly market share there. 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. You had a choice to make, which was obviously what you're selling is like work 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 where 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. Many other companies, right. Because it's easier [32:01](https://realalpha.app/v/QnkQhyOGo3k/?t=1921) to say, look, I'm not going to try to 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'd you choose that? 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 that is a system of record, but doesn't look like the existing systems of record. What does it mean to be the system of record? If not just like a database? What is it? It is, well, look, HubSpot is appropriately named. It is the hub. Everything orchestrates from the system of record. Yes, because it's the source of truth of data. [33:19](https://realalpha.app/v/QnkQhyOGo3k/?t=1999) That's right. And you asked a question like, why did you make this decision? Well, 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. 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. [34:15](https://realalpha.app/v/QnkQhyOGo3k/?t=2055) We're not motivated by an outcome, which again, like a really exciting outcome for those that experience. We want a shot. We want a shot at being a market leader in 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. Yeah, that's right. And so the future market leader has both that IT budget, but it also has the labor budget. Monaco is way more expensive than that sort of legacy system of record products because we are doing the labor on behalf of our customers. [34:47](https://realalpha.app/v/QnkQhyOGo3k/?t=2087) Which, by the way, is the story of all these AI native companies. It's true. 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. That's exactly right. And people, not only are customers willing to pay, this is what they want. 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 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. The thing that I think is less obvious in terms of an application of AI that we've been very deliberate about, [35:46](https://realalpha.app/v/QnkQhyOGo3k/?t=2146) **Sam Blond:** 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, [35:56](https://realalpha.app/v/QnkQhyOGo3k/?t=2156) 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. 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 know, the customer just gets a straight up better experience because the data is tied together. [36:32](https://realalpha.app/v/QnkQhyOGo3k/?t=2192) 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. The compound startup, maybe phrase or terminology that I think Parker made famous. Yes. And now it's like that should go like exponentially far. Well, 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 the exact sort of math equation here, but we can build software. It's something like 10 times faster than we could just a few years ago. [37:15](https://realalpha.app/v/QnkQhyOGo3k/?t=2235) 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. 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. 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 [38:19](https://realalpha.app/v/QnkQhyOGo3k/?t=2299) 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 sell it for per user per month kind of situation. 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. Right. It's even more pronounced, I think, in the world of like finance and accounting where there is like an actual number. There is like a real one zero type number that is the calculation of everything that comes before it. Yeah. 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, then there is this sort of like 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 [39:35](https://realalpha.app/v/QnkQhyOGo3k/?t=2375) signals that we're leveraging and how does that be incorporated into messaging and these things that many of our customers today just don't have experience doing, right? And so then that is the first thing that comes to mind is like the opinionated nature of the product yes um 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 that kind of like what you're selling to the customers. [40:02](https://realalpha.app/v/QnkQhyOGo3k/?t=2402) Yeah, 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 startup 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, 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. [41:08](https://realalpha.app/v/QnkQhyOGo3k/?t=2468) 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 when it comes to the category of like go-to-market or sales. It's revenue. How much revenue are you generating? 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 um that is like fairly easily measurable so i would love to unpack kind of the go-to-market strategy you've had so far you launched like february so let's call it four or 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 um share what was in your head when you're like okay it's time to launch we're gonna be loud here's the things we're going to do to sort of like get this whole brand going? Yes. Uh, I think, um, I'll describe [42:23](https://realalpha.app/v/QnkQhyOGo3k/?t=2543) our approach. Um, it was the right approach for us. Um, I'll also sort of caveat with a couple things that, uh, I think are worth calling out that, um, maybe like advantages that we have as a business that don't necessarily apply to every startup. Um, 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. We certainly spent zero dollars on marketing up until the day that we launched. 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 that 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 [43:35](https://realalpha.app/v/QnkQhyOGo3k/?t=2615) time ago and they like did this thing. You can imagine the sort of like psychological impact of that relative to um like dropping the frog in the boiling water which is like oh my gosh we are seeing monaco everywhere all of a sudden like i see the plane and i see the billboards and i see the poker tournaments and your your uh your plane 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 just were like, Monica. [44:06](https://realalpha.app/v/QnkQhyOGo3k/?t=2646) 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 more. When we do think that there may be like two impacts of brand awareness. [44:42](https://realalpha.app/v/QnkQhyOGo3k/?t=2682) 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, they receive the message from me. [44:53](https://realalpha.app/v/QnkQhyOGo3k/?t=2693) **Sam Blond:** They have heard of Monaco because they've seen the plan, whatever the thing is. [44:57](https://realalpha.app/v/QnkQhyOGo3k/?t=2697) 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 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 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. 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. I can talk about maybe like a couple marketing principles that are things that we apply to marketing. [46:00](https://realalpha.app/v/QnkQhyOGo3k/?t=2760) 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 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. Yes. 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... But there's a version of it for almost everybody. There's a version of it for everybody. I think there's a process that every company should follow. And then I can talk about maybe a couple of principles in case they're helpful. There is a process which most companies do not follow. You've got to try stuff. You just have to just do stuff. And you can't be afraid to fail. And I do think that most companies here, they just don't really do anything. [47:09](https://realalpha.app/v/QnkQhyOGo3k/?t=2829) 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. 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 the shoes of 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. [47:44](https://realalpha.app/v/QnkQhyOGo3k/?t=2864) I don't know how to do like a marketing campaign. 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 2018. And that just like landed super hard. and that engineer yeah yeah uh so I'm not, I'm bad at this, so I'm not experiencing this or whatever. I don't 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. [48:20](https://realalpha.app/v/QnkQhyOGo3k/?t=2900) You 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. Uh, and just ideating on this. And I think that's hopefully a high ROI to our customers. Um, and you can do inexpensive campaigns. Uh, like one, you don't have to be an expert at this too. Um, 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 110 bucks. Um, you can do a test, send this to 50 people. You're spending $5,000. It's like, um, Now, if you are truly bootstrapped and have no dollars to spend, sure, you can't do the $5,000. [49:06](https://realalpha.app/v/QnkQhyOGo3k/?t=2946) But you can still do stuff. There's always stuff you can do. 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 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. [49:35](https://realalpha.app/v/QnkQhyOGo3k/?t=2975) 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 that um are in this like category of marketing brand awareness demand gen however we want to frame it uh and i think we really want to be um contrarian is maybe like not the right application of that word but we do want to be creative new stuff new stuff like your plane the plane was awesome can you talk about the plane yes i feel like there might be one flying right right now we um there there isn't we took it down we'll put it back up at some point uh i think like probably reached diminishing returns or something over time but it was like yeah anyway go ahead yeah we we were at saster which is um jason limkin's conference awesome conference uh and we knew that there would be like a large contingency or concentration of people at this event down in san mateo and so um 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 [50:40](https://realalpha.app/v/QnkQhyOGo3k/?t=3040) same event um 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 yeah and then um i was surprised at how relatively inexpensive putting this plane in the air for many hours during the conference was which is like six thousand bucks a day and you know we do it for two or three days at the conference um and i was just sort of thinking like we already have the banner um we already know like the cost of flying this thing yeah uh 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 math on this thing and it was like six thousand bucks a day pay for 10 days it's 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 the worst case scenario, we fly this thing around. It doesn't totally work. We like learn from it and we don't do it again. [51:51](https://realalpha.app/v/QnkQhyOGo3k/?t=3111) It worked. So we, you know, both like messages on my phone, people posting on LinkedIn and Twitter and everywhere. else. 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. You know, it's interesting, like history kind of, I'm sure you've read Behind the Cloud, you know, the early Salesforce book from Benioff. And like one of the things that like struck me was like early Salesforce did a lot of really creative marketing they did 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 i think they're um the one that i understand as much as any was like the the protest it may be like a big siebel or [52:52](https://realalpha.app/v/QnkQhyOGo3k/?t=3172) oracle conference where it was like the no software um which i think was uh really smart yeah so like when you're thinking about this are you are you like i'm gonna do new activities and then i'm gonna 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 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 um my guidance to any customer that i'm working with is like, you should try and apply the same logic as well. 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 second is like creativity. The first is like, it's oftentimes lower friction to do. It's mostly paid online advertising. I think if we looked at maybe like series C plus technology startups, where is most of their marketing spend going? It is likely going to third party advertisers. And I surmise like at the top of that list is probably like the Google's [54:06](https://realalpha.app/v/QnkQhyOGo3k/?t=3246) Metas, LinkedIn's 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 lowest ROI. It's like a fairly efficient market at this point. Yes. 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 than do the like efficient market paid advertising marketing spend where most of our marketing dollars collectively are going. 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 [55:23](https://realalpha.app/v/QnkQhyOGo3k/?t=3323) 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 clear channels and out fronts of the world that we are paying to put ads up around San Francisco. 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. [56:00](https://realalpha.app/v/QnkQhyOGo3k/?t=3360) **Sam Blond:** as a customer. Early on, I would try and bucket like 100% of the marketing spend actually to something that benefits the person that we are targeting. And if you put yourself in the shoes [56:11](https://realalpha.app/v/QnkQhyOGo3k/?t=3371) of a prospective customer, you are a, well, let's take Monaco as an example. You are a YC founder. Yep. 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 yeah or would you rather have monaco send me a like poker set like heavy clay poker chip 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 um we had we give away a hundred thousand dollars Monaco Invitational, you were there. The final table gets all of it. Let's say there are a hundred people that start playing. 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 might be using Monaco? Would you rather have us throw this poker tournament that you come to, have hopefully a blast, make like a bunch of money at the final table or again, like pay Google for like the SEM, whatever stuff that's like following me around [57:22](https://realalpha.app/v/QnkQhyOGo3k/?t=3442) when I go to different, uh, either websites or Google searches. So, um, uh, use that as like a bit of a thought exercise, allocate your marketing dollars that would 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. Um, and so what we want to create um is like a bit of a monaco community um through our customer base but the the like the most effective um marketing spend that we have and when i like approve this going out it is like my favorite bill to approve of literally any bill that i approve at the company is the like referral it is the like customer referral where we are paying somebody two thousand dollars because they told their friend that they love monaco that friend should check us out that friend signs up yes and look if we're doing a couple grand a month um we're paying people like ten thousand dollars to send us customer it's like the the highest roi use of what is effectively a marketing spend yeah right that is a customer acquisition cost that's right yeah that's awesome so um when we uh so i mean i guess this is the like kind of air cover and then the other half i [58:36](https://realalpha.app/v/QnkQhyOGo3k/?t=3516) guess of early startup go to market is like the ground game and maybe just to wrap you know this conversation can you talk about your 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. What are the principles you're teaching me or talking to me about as a sales org builder? Yeah. Well, first, maybe at a more, we've already used this word in a different context and more like meta level. I think that there's something that 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 focus our actual time and energy on, which is the thing that you just talked about. [59:35](https://realalpha.app/v/QnkQhyOGo3k/?t=3575) So backward looking, I think most labor 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, all of this like fully online. workflow orchestration that agents are just better than any human in the world at. And so it is true that that is like what Monaco does for you. All of this sort of like 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 Monica 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 meeting with customers. [1:00:41](https://realalpha.app/v/QnkQhyOGo3k/?t=3641) Today, especially if you were in like B2B, 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, maybe on, I would suspect, our customers' time than spending time with customers. And a lot of the things that we're able to leverage with AI allow us to spend far more of our time, whether you're a founder or a salesperson, on that human connection, developing relationships, customer facing. I think the second thing is this category of creative, operationally complex campaigns. We've talked about a bunch of them. You could do like a chat GPT conversation where you're like, can you come up with some marketing ideas for me? [1:01:34](https://realalpha.app/v/QnkQhyOGo3k/?t=3694) I think it would be hard for that to result in the plane, as an example. 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 are trying to do something like truly creative, in of one, innovative, I think it is more likely to surface inside the four walls of your company by doing the sort of like ideation that I talked about, which is let's come up with two ideas, each person multiply by four, that's eight ideas, 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 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 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 yeah that's awesome um 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 practice of, you know, [1:02:48](https://realalpha.app/v/QnkQhyOGo3k/?t=3768) the time with the customers itself? I think there are two things that stand out as, 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 starting to sell their product and don't have a lot of go-to-market experience that I think have maybe more impact than any other, you know, below these two. The first is I would be fairly prescriptive [1:03:16](https://realalpha.app/v/QnkQhyOGo3k/?t=3796) **Sam Blond:** about how to effectively buy your product. Because 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 combination of like [1:03:34](https://realalpha.app/v/QnkQhyOGo3k/?t=3814) agenda and opinion 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 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, 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. [1:04:08](https://realalpha.app/v/QnkQhyOGo3k/?t=3848) But we sort of start with, and this is very abstract, we sort of start with like, we, you know, meeting two, we come with like our prebuilt custom environment to show you exactly what it would look like on our product. If that resonates with you, we sit, we put you in like 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've 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 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 yeah yeah what's the other the the second thing is like um a little [1:05:17](https://realalpha.app/v/QnkQhyOGo3k/?t=3917) bit of an urgency driver, where if you can create some form of FOMO, for lack of a better word, I think that much of sales is psychology. And so for many customers, what I'm about to articulate is true. We certainly never want to say anything that is untrue or misleading. But if we have, we're in the month of July, if we have a goal to onboard three customers to pilots in the month of July, what we articulate to 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. What we say is something like, 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, Like, I can't guarantee the spot if you don't speak for it today. [1:06:18](https://realalpha.app/v/QnkQhyOGo3k/?t=3978) Yeah. And I think that's true because you can only onboard so many at this stage. That's exactly right. But it does sort of force a decision and potentially drive some urgency. There is like a psychological aspect to this where it's like, oh, gosh, two two thirds of the spots are already spoken for. Like, I better speak up to like, you know, get this thing that a lot of folks are already incredibly interested. I assume also important in all of this is sort of just like having like 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. [1:07:03](https://realalpha.app/v/QnkQhyOGo3k/?t=4023) Man, when you say that, it's interesting where my mind goes, which is something different than what you just said. But I think it is true that growth solves a lot of problems. I think an 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 founders and salespeople are hanging on for dear life to the one guy that I pitched over the last couple of days because they kind of seemed interested. That's right. But if you're like, I've got four more calls I should get to, and 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. You can, Parker, I stole this from him. You can sort of swipe left. I've never been on one of the dating apps, but I think Tinder, you sort of like swipe right if you like them and swipe left if you don't. And so an abundant pipeline allows you to only try to sell the product to people who need it. [1:08:02](https://realalpha.app/v/QnkQhyOGo3k/?t=4082) That's exactly right. And it's not, when I say that, it's not like disrespectful to the customer or being inefficient about not following up. 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. Yeah. But like actually probably isn't actually interested if we're intellectually honest. 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 oh we have so many customers if you're like 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 we're we're four months in um four or five months in uh launched in february and um monaco does an awesome job of continuing to engage with older customers on our behalf. But I cannot tell you, well, I can tell you the amount of times where I'm just sitting there and resurrected from what effectively [1:09:08](https://realalpha.app/v/QnkQhyOGo3k/?t=4148) 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. And again, all of this stems from more demos in February, right? And so I think lots of sort of anecdotes of what a demand-rich environment evolves to. Sam, this was awesome. I learn a bunch every time we talk. Thank you for doing this with me. You are the best. Thank you so much for partnering with me on Monaco. And it's just an absolute pleasure to come on the show. So thanks for having me.