What Wins When Anyone Can Build Anything with Brett Queener, Partner at Bonfire Ventures

Brett Queener (Partner at Bonfire Ventures) joins GTMnow to share what three decades across Siebel, early Salesforce, co-founding, and seed-stage investing has taught him about what actually wins now that software is cheaper and faster than he ever imagined.

Brett was one of the earliest GTM hires at Salesforce when it had seven employees. He helped build the go-to-market playbook that defined a generation of SaaS: enterprise segmentation, sales motion design, product marketing, the whole works. He then co-founded SmartRecruiters, angel invested in companies like Outreach and Pando, and eventually joined Bonfire Ventures as a Partner to do early-stage investing the way he thinks it should be done: hands-on, operator-led, and built around founders who are ruthless about execution.

Guest links:

Brett Queener - LinkedIn: https://www.linkedin.com/in/brettqueener/Bonfire Ventures - LinkedIn: https://www.linkedin.com/company/bonfire-ventures/Guest company website: https://www.bonfirevc.com/Host links:Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/Max - X: https://x.com/HackItMaxPaul - LinkedIn: https://www.linkedin.com/in/paulsirving/Paul - X: https://x.com/PaulGTMNewsletter: https://thegtmnewsletter.substack.com

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Transcript available under the episode here: https://gtmnow.com/tag/podcast/

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Highlights:

00:00 – Brett's career: Siebel, Salesforce employee #7, co-founder, angel investor, seed-stage VC06:58 – The big shift: from passive CRUD apps to agentic software that does the work for you08:07 – "Failing upwards" and what the fastest-growing companies taught Brett about investing in people10:58 – Why Brett moved into VC: 25 years of operators whose collective worth hit $25B16:50 – What Brett looks for in founders now and how it's changed over 6-7 years18:05 – Why anybody can build anything: Brett builds a fully functional travel app in 15 minutes19:20 – The last remaining

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Transcript

SPEAKER_00 0:00

Thriving in the agentic age is ruthless and much more ruthless than in the Sas Age. Right? If anybody can build anything, what's the last remaining moat in software? So, like in that world, I kind of like the psychos.

SPEAKER_03 0:11

Brett Queener, managing director, Bonfire Ventures. And we get into what the last moat in software really is.

SPEAKER_00 0:18

You are ruthless and relentless about execution. And then what do you believe is your right to win? And the rate of change if your product isn't on par like every 30 days because the marketing breaks.

SPEAKER_04 0:30

And for Brett, the founders who win right now, it comes down to one thing.

SPEAKER_00 0:34

I don't think you're a functional leader in go-to-market unless you're building. Because how are you gonna go run the org to understand where I want humans and where I'm gonna use agents unless you're building?

SPEAKER_05 0:44

Agent Eric, how does this change how go-to-markets can done?

SPEAKER_00 0:47

You're showing products much earlier. Deployments often happen before you close.

SPEAKER_05 0:51

Do you think a company like that needs less money over time? They need to hire less people.

SPEAKER_00 0:55

We need less people in the startups.

SPEAKER_05 0:56

That being said, welcome back to another episode of the GTM Now bonus VC podcast. I'm here with my partner, Paul Irving. What's up, Paul?

SPEAKER_06 1:18

How are you doing, Max? We got the matching blue sweaters today. Lots going on in the software world, AI world, uh ready to roll.

SPEAKER_05 1:25

We got a great guest for the show. We got Brett Queener on from Bonfire, uh, was an early Salesforce guy who's got lots of good stories, but also learnings from working very closely with Benioff and some of the folks uh early at Salesforce. To that point, GTM is changing more than ever before, you know, right in front of our eyes. And at the same time, you know, it's funny. I feel like some tried and true stuff, you know, the last remaining things that are working from the previous eras. What did you learn from the the Queener episode on the GTM front?

SPEAKER_06 1:58

Yeah, it was really interesting uh because we did, so it would have been last year we did our AGM. We got three of our founders on stage to talk about what's working in GTM for them. And we chose three very separate industries that these these founders are building in to get some diversity of strategies and execution on the stage that day. And two out of the three of them ended up with what they called the donut playbook, which was you know delivering donuts in person to customers, flying to them 70 miles drive or getting on a flight and renting a car and driving and showing up at the telecom office in rural Indiana that could be a 250k contract, meeting the VPs that are decision makers in person, delivering food, you know, moving that account through the pipeline as a result of that in-person relationship building interaction that you had. And uh, I think Brett used the exact same example. Uh, it was the donut playbook. And in-person events seem to be working really well, whether that's dinners or conferences. I think we see it across vertical software and AI. Um, these trade show style conferences still seem to be where the most important relationships get built and go to market, smaller dinners and events, relationship building, whether that's again, you're dropping off something and seeing your potential enterprise account in person, or you're finding a way to get in a room with them in a variety of different other strategies. But but it seems like the old playbook of you know, human-to-human relationships and decisioning is still going to matter. So, what's your competitive advantage to get in front of your buyers? Uh, and how can you create those moments of seemingly serendipity?

SPEAKER_05 3:33

Yeah, for the most part, the buyer is still a human. Maybe tough for that to ever be like fully AI. In the meantime, for the next few years, the buyer is human. And so the seller needs to make a genuine connection with the human. And the best way to do that is events. But it's also listening to and finding things out that you can find out. You know, Nick Meta posted the other week how a toy Porsche on Amazon changed a massive deal for his company because a new executive took over for a business and they were gonna churn, and he had no connection with the new executive, and he finally got 15 minutes with the executive, and one little nugget he learned from that phone call was that they were into racing, and he sent them this little toy Porsche and you know, a nice note, and that was enough to get that person to come to the table and do a meaningful evaluation. And they ended up retaining the customer and growing that customer to a multi-million dollar contract. And we had a similar thing at Outreach. We had uh a massive deal that we were trying to break into, couldn't get into the main point of contact or anybody on her team, called a big uh executive meeting for it. I was on Twitter, on this woman's Twitter, scrolling, scrolling, scrolling, all corporate comps, all about their upcoming event or you know, previous events. And then finally, five years earlier, a tweet referencing the Steelers. So she went to Penn State, sent her some James Connor swag, who was the running back for Penn State, and then the Steelers. A week later, we had her entire team on a meeting and we had the ball rolling on the deal. That genuine connection between humans, there's nothing like it. It is one of those things where you talk about kind of moats or things that are enduring through the kind of AI craziness we're going through right now. That is going to endure. Until the buyer is AI, that will endure. We talk about PMF also. And Brett said this. We had one of our portfolio companies, May Habib from um Writer, say this, but PMF is a treadmill in the AI days. At this point, you're constantly reinventing. And Dreesen said this in his post in his podcast with Lenny, too. You're constantly rethinking, you're constantly reinventing your companies.

SPEAKER_06 5:49

Yeah, it's really interesting because I think it reframes the way you think about company building if you're a founder or one of the operating executives at a startup, and it changes the way we look at investing as well. There just used to be very clear stages where, you know, in the early days, we're working with design partners, and then we find a common problem that people are willing to pay for, that's a burning need, and we sell them our technology to be able to solve for it. And then we start to feel repeatable pull in the ecosystem or market we're selling into to solve that particular problem. And you have this foundational ground you can stand upon. But when technology is moving this fast, what's possible and the surface area of what you can solve for your customers is shifting this fast. The number of competitors that are coming to market is growing at the speed that it's growing at the moment. You start to get this feeling that Brett and we've had founders and other investors, you know, echo before, which is that product market if it feels like a treadmill, you have to almost earn it every single quarter. And the best founders and the best companies are going to stay incredibly close to their customers of where their problems are shifting and where that's moving, stay at the cutting edge of where technology is going and make sure that their product roadmap reflects that at all given times. And the people who are able to stay at that treadmill or on the treadmill at the speed in which it is moving right now are going to be the successful companies. But it's a reality from the earliest stage startups to now you're seeing it in the public markets as well. Product market fit isn't a constant.

SPEAKER_05 7:12

We've had a couple of our portfolio companies that have have had pivots, one product to a completely new product and more of a pivot from we've had product market fit, but the way that the product is built completely needs to be reimagined. And we have to like break it all down and do it again based off AI native. And it's incredible to watch these founders do that. They get it done. What are VCs looking for founders these days? And I guess the second question to that is are there any moats left? What do you think? What are you seeing?

SPEAKER_06 7:43

Yeah, I mean, there's the constants, which are always going to be things that you look for. I mean, these are exceptional outlier human beings that are creating magic out of nothing, and that requires them to be very spiky in certain skill sets. I mean, I think that's still something we look for and we probably look for more than ever is you know, you almost want to find somebody who's not a 90 out of 100 on everything, but you want them to be a 99 out of 100 on a few important things. And then, you know, our job is to see if we can help them, whether it's higher or just learn and grow to support the other attributes that will make them successful. To that point, I think slope of learning is is always been important, but probably now near the top of my personal list because you know, the point about product market fit being a treadmill, if if things are going to move and change this fast, you need to have somebody who is both like willing to learn that really thin line of acting with conviction, but also be open to changing your priors when new information comes to the table. And then learning constantly, you know, wanting to talk to the best people, the smartest people, listen to their customers, and have this really, really high slope where if the world is going to change around them, they are going to ensure their business is pointed in the right direction as a response.

SPEAKER_05 8:56

You know, on the Motes point, obviously with AI, easier and easier to build than ever before. You're seeing it. And you're seeing Claude come into everybody's space. It's incredible to see what some of these founders are able to do with way less resources. I mean, you get you get a founder who's kind of a tinker and they can get very far tinkering. They could go build an entire product. They can go do some really hacky stuff on go-to-market. You're seeing more and more people hiring and vetting for this generalist or this ability to kind of use Cursor or Replit or Lovable and some of these and some of these products right out of the gates and less on historical. Oh, can you do the sales job? Can you do the marketing job? It's fascinating to see, but it's also when I'd have phone calls with founders and phone calls with, you know, folks that are coming out of companies and looking for their next jobs. So, what do you recommend I do? I'm like, I recommend you understand Claude Code. I recommend you get in the weeds and understand how these things work because you're gonna be expected to do these things in your business. Like we're getting out of these like political structures and like hiring 30 people to run, you know, be on a marketing team. And it's like, okay, all of this can be done by less, less folks. Which brings me to another point. It's like, does that mean that jobs are gonna go away?

SPEAKER_06 10:17

I I think February of 2026 was one of the most narrative-dense months that we can remember, like probably since ChatGPT launched, so in years, where you saw it in the public markets, you saw it in some of the smartest and most influential people within tech and VC coming out and writing very thoughtful essays for their description of what the future is gonna look like. And one of them that caught fire was the Citrini article about the ghost economy and we're gonna lose all these jobs and AI. Well, it's gonna create efficiency across all these businesses, it's not gonna go into the pockets of the individuals with a new economy. And if they're not spending, like we're gonna have this huge economic collapse. And the problem with that point of view and orientation on AI and what it's going to do to the economy at large is you're applying a dynamic variable, new technology, AI in this case, to a static ecosystem, which is the global economy and companies. When in reality, the global economy and companies are anything but static. You're applying in the real world, you're applying a dynamic variable AI to a dynamic ecosystem. And the idea that it's not going to respond in turn to the changes, the impact, and to every action, there is an equal and opposite reaction. And the idea that I think Mark Andriesen summarized really nicely, which is okay, sure, we might eliminate this section of your job and XYZ company, but you have the most powerful leverage point in the history of humanity sitting on your desk to do anything you want, create a new job within that organization, be AI native, you know, ahead of the rest of your peers. Go become an entrepreneur because you've never been able to create more on your own than you can today, and you will be able to tomorrow. And so this idea of loss without a response is always felt like a half story in my eyes, at least. And I think Mark did a good job of summarizing that is you have the world at your fingertips more than ever before. The question is what you're going to do with it.

SPEAKER_05 12:16

Well, it's an exciting time. You know, we had the Citrini research post that came out. You know, everybody starts going into all the doomsday scenarios, but you've now had obviously we've had time to sit on it. I think we've kind of done a rebuttal with our own LP update, which we'll shall share publicly. You've got the Michael Block 2028 Global Intelligence Boom rebuttal. You've got the Citadel Securities, which was another rebuttal, uh, the David Andre SAS is dead, Agents Killed It article. There's so many different points of view on kind of what we're we're going through right now. And you know, really appreciate a lot of the smartest minds in the world kind of chime in on this stuff, but at the end of the day, it's nice to be in a seat where, you know, we'll kind of see it. We see it happening right in front of us, unfolding right in front of us. And, you know, we're able to kind of re-underwrite our thesis, our ever-evolving thesis at this point. Based on that, it's just moving faster than ever before, and you really have to kind of keep a finger on the pulse.

SPEAKER_06 13:12

It's an exciting as exciting time as ever before. I don't know if I'm sleeping well. I think if you're not equal parts excited and paranoid simultaneously, you're missing out on the full experience, but probably more opportunity than ever before, which is fun.

SPEAKER_05 13:24

Anxiety, anxiousness, excitement, all high. We are going to get into the Brett Queener episode of the podcast. Uh, really great one today. We'll pass the baton. So, Brett, great to have you here. Absolutely.

SPEAKER_00 13:38

Glad to have you in my hometown. Yeah, Santa Barbara. It's not bad. It's a nice, nice respite for a day a week. Yeah. From the uh from all the noise.

SPEAKER_05 13:47

Your career talk about a roller coaster. So started SIBL, Salesforce, 70th employee, around 70, now in venture capital. Yeah. Now looking at all these AI agents making your head spin. Like, wow, this has been quite a journey from where I started. Talk me through one, how you ended in VC in the first place. And two, are there things that you've gleaned from I guess working that closely early at Salesforce with Benioff and and and folks that you know help you be a better VC today?

SPEAKER_00 14:17

I think what is interesting. We'll get to VC in a second. Um two thoughts. One is my career is weird, right? Like I got into I got out of college when client server was coming out. So I was the Jimmy Neutron that brought like email and client server into a company in Milpitas. Back in the early 90s, there were no jobs in San Francisco. You lived in San Francisco and you drove all the way to the South Bay. Now, before that, life was cool because when work was over, you would go home and no one could get a hold of you. Like trying to explain to your child what a pager was and a car phone is or a public phone is always an interesting conversation. And then I got out of business school right as Netscape uh went public. So the birth of the internet. And so I think what is interesting about Salesforce and kind of where we are today, where this big shift. There was a big shift from on-premise to cloud, and there was huge differentiation, et cetera. Right. Like uh and right now we're moving from what I'll call sort of passive crowd applications where the human does all the work to agentic products where the software helps you do your work or does a lot of work on your behalf. Right. So very huge sort of transition. Um in terms of like VC, we do you know, we're at Bonfire, we do seed stage. We're investing early. It's like five to eight people. We got like three to four weeks to figure out if we're gonna dance with this founder. Uh what we try to do is spend more time with the pre-seed people right out of pre-seed so we get to know them, et cetera, et cetera. And look, I think the similarity with Salesforce or working at Salesforce or working at Sebl or et cetera, the one of the similarities is an operator being a venture capitalist, right? There is the you know, there are venture capitalists that are professional venture capitalists, they don't look for deals. You're a little more like me, right? We're operators, right? We we look for people that we think can out-execute other people. Um, we look for signs of emotion where we can sniff repeatability. But for me, if you think about my career at Siebel or Salesforce for the two fastest growing companies respect to time, was I picked right and I failed upwards. And in failing upwards, for those that know what failing upwards is, if you join a company that's growing so fast, they can't hire enough and they basically try to give you as much responsibility until you break. Right? So you're like an SVP before you've reached puberty, right? And then we know what that means, right? Yeah, um, so I did a really good job of that. But look, I think you know, in your experience as well, like if you're investing early, you're really investing in an individual. They're gonna have to pivot. Now I've got founders that have to find and refine market fit like every friggin' three to six months.

SPEAKER_02 16:57

Yeah.

SPEAKER_00 16:57

They have one motion at work, so they're all excited, like, oh shit, that broke. And like all of my success prior to BC was tied to the quality of the people that I hired and how effective I was in sort of managing and motivating them. So I think there's something similar there in terms of like um the relationship you build with founders, um and I don't want to call it therapy, but like look, being a founder, having been a co-founder, it's a lonely, hard, existential place. You know, and I think uh Horowitz said it best, right? And hard things about hard things, nobody cares. Like nobody gets a shit. And so to the extent that as people are working through stuff, they can call us and be like, dude, I need some help. Because my my general view in life, and I say this to my kids as well, or people when they struggle, I go, you know, we don't have too much of a struggle, right? I don't want physical pain. But we as humans, we only learn from mistakes. You never learn from like, oh, I did something well. It's when something doesn't go well that you process and go, let's not do that again. And if you think about your time as an operator or my time at working at Salesforce in the early days, um was it's just a series of trial and error and loops. And you need to be um thoughtful enough to have trade-offs of what you're gonna do, but you need to be humble enough to basically say that didn't work and then operationalize that. And that's really the I mean, if you think about the early days of Salesforce, um, there was I don't think a blog, I don't think a blogging platform exec. Maybe it did, but like there was no how to, there was no podcast. We were just making this shit up, we was going along.

SPEAKER_05 18:35

Yeah. Now there's more content you can you can possibly.

SPEAKER_00 18:37

Oh my god. Like on the way here, I was listening to a notebook LLM that two of my founders are trying to explain to me, you know, the meaning of a word has no meaning unless it's a relation to other as the basis for why AI and where it's going, and graph rack. And at some point you have to turn it off. But I feel like the early days of Salesforce is very much of a beginner's mind. And I think where we are today, we have to approach what we're doing very much of a beginner's mind. So that's sort of how prepares me for VC. And like, you know, people ask me why did you do VC or why are you doing VC? Like, probably more reflection of them than my hiring capability. But if I look at the people that have worked for me over a period of time, I think their collective worth worth is like$25 billion. Now I wish I had been able to invest in each of them, but for the limited period of time that they worked for me, um, they defined my success. Uh and so for me, this is sort of giving back.

SPEAKER_05 19:28

Yeah. Right. You kind of beat me to it, actually. The Salesforce was a obviously if you were there early, but even now, it's a very entrepreneurial company. A lot of people come there, do their tour duty, then they start a company, and a lot of those companies have gone on to be very successful. You were one of them. Uh smart recruiters, were your founder of Smart Recruit?

SPEAKER_00 19:48

Co-founder, there was a founder. Um I had thought at the time that I wasn't a foun I wasn't the founder because there's something about the soul and spirit of the founder that you the sort of the craziness of it. You know, we're operators, we're sane. I mean, people think I'm pretty crazy, but we think systematically and we're process thinkers. Yeah. Uh and so I partnered with Jerome um to go and try to change recruiting, which was not easy.

SPEAKER_05 20:14

Like that's a hard but you gotta put yourself in the founder's shoes there.

SPEAKER_00 20:18

I got it was painful. I think it that was very helpful in working with founders. Because when you work at like a SEBL or a Salesforce, they've market fit, they're succeeding. You know, and yes, you add value to those companies, um, but like they were gonna succeed kind of without you. Um and I think in a co-founding spot, it was really hard. I brought all the playbooks I knew before, which was sort of the uh child, you know, the the challenger sale, the innovators dilemma, to a market that didn't work in any way, shape, or form. It was like a risk-adverse buyer.

SPEAKER_02 20:50

Yeah.

SPEAKER_00 20:50

And so in like struggling, it allows me to empathize with founders, right? You probably like I could look at a founder, you're on a phone call with them, and you're like, all right, come on, what's going on? Yeah, and it's a big part of it. Yeah, I often tell them, like, look, give me your Slack org. I don't need to be all in your Slack org, but like create a general feed, you know, new hires. I can read all of that. We don't need to have a call for you to tell me what's going on. Yeah, I can see that. But let's get down to like what are the top two three things that you know you're worried about. And like every founder has this version of a dream. We all have these anxiety dreams, right? You know, the dream about like there's some math class in you're in school, there's a math class, or there's an exam you didn't study for, right? And mine was um I'm on Broadway, of course, a little dramatic. I'm the lead, of course I'm the lead in a show. And I'm going on stage and uh family's in the audience, New York Times critics in the audience, I'm naked and I forgot my lunch. And I always woke up before knowing if I was too much of a coward to turn around and go forward. But that was like a constant train. And look, if you're you're a founder and a startup, you have like three things you know, you're wrestling through your head, you're like, what is the thing? You wish you knew so you could go do something about it. Yeah. That's stressful. The bigger stress is you know what you should do, and you're you thought you've assembled the team you need to go do, and you can't it's not executing. That's the one that you're like, oh you know.

SPEAKER_05 22:17

Yeah.

SPEAKER_00 22:18

But I think that has been, you know, helpful.

SPEAKER_05 22:21

And you're also, you know, that entire time angel investing.

SPEAKER_00 22:25

Yes.

SPEAKER_05 22:25

So you're working with companies, you know, as an individual individual.

SPEAKER_00 22:30

And then, for example, on Pendo, it was one of the first checks into Pendo. Um I'm the independent.

SPEAKER_05 22:36

Okay.

SPEAKER_00 22:36

So, you know.

SPEAKER_05 22:37

And you're still still on the board there? Just there, just support meeting lists. And he never did anything through Bonfire. There was that that was No, that was before.

SPEAKER_00 22:43

That was before. And then outreach, yeah. Right with Manny. Yeah. And now he's over at Paid. Yeah. I was a little upset that he didn't call me when he was racing that round. He's playing, well, Brett, this is the round I did. You can't. I'm like, you're right, man. I don't invest. That's a little pricey for me.

SPEAKER_05 22:58

That was a that was a crazy one. And you know, it's Manny, so he's got a million people knocking on his door at all times. But so okay, so you've got this early Salesforce experience. Then you went out, did the founder thing yourself. Obviously, Angel invested along the way. So you're already working with a bunch of other founders. How how did you end up at Bonfire?

SPEAKER_00 23:18

Well, I was down, you know, I moved to Santa Barbara like 16, 17, primarily because my wife's like, look, we need to get these kids into college. And she's from Santa Barbara. We had a home down here. Uh and you come back and forth. It's not so far from the barrier. It's pretty nice on the weekend to sort of like clear your head so you can think anew on Monday.

SPEAKER_02 23:38

Yeah.

SPEAKER_00 23:38

And, you know, I came down here for a couple years. Uh, I came down here uh with the kids sort of active in their high school experience because you know, we work at Seabill and Salesforce, and you know, your global services, there's a time at which you need to pay back and like takes responsibility here. And then I'd known Jim Andleman. Uh, I was uh independent on a company down here, Columboka. He was an investor through his predecessor fund RingCon, and we got to know each other, and they were coming together with Bonfire, and they were looking for a third partner that was more of an operator. Um, and it was seed stage, uh, and it was gonna be hands-on.

SPEAKER_05 24:15

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SPEAKER_00 25:05

We gotta define what the hell seed means.

SPEAKER_05 25:07

What does that mean? I don't even know. But uh so tell me about it. What are you looking for in a founder? You know, you have this kind of robust history where you've worn these three different hats, let's call it early at Salesforce, then a founder yourself, an angel investor that's kind of informed your thinking to date, mixed with this kind of AI, LLM, agenc new world that we're in today, how has your thinking changed? What kind of what in an investment, what are you looking for?

SPEAKER_00 25:38

Well, I think the biggest thing that's changed, even before I get a day out, and you've probably seen this yourself, which is if we're an operator, we mistakenly assume that like we have a very outsized impact on a company. Like there have been founders that have but great ideas, et cetera, et cetera. But then you have to realize you're not running that business. Um, so I think the biggest thing that I've changed for investing over the last six to seven years is I could be a great thought partner, I could be a great aspiring partner, um, I can help them as they're thinking of scaling and thinking through those things, but they need to succeed independent of me. That's the biggest thing. Yep. I think the second thing, we've always said it's about founders, but I would say that thriving in the agentic age is ruthless and much more ruthless than in the SaaS age.

SPEAKER_05 26:31

Interesting.

SPEAKER_00 26:32

Right? If anybody can build anything, I don't know if you've been messing around with cloud code or cloud co-work, but built some apps last week. I built apps, I built an app in 15 minutes, and 10 of it was just remembering how to like install Node.js and figure out deploy and re because I could in high school, a terminal. I was like, okay, yeah. Um, I'm going on a daddy-daughter trip. My daughter's 26, so she said, let's do one, which is great, right? We used to go to I've seen Harry Styles seven times, four times is one direction, whatever it takes to stay. Whatever it takes. Whatever it takes. Uh so I told her that Harry Styles was coming to New York. Let's go to New York. And she's like, I don't really do that, but let's do a daddy-daughter trip, which was great. Wife tried to invite herself on it, and she's like, Mom, it's daddy-daughter.

SPEAKER_02 27:13

Yeah.

SPEAKER_00 27:13

In another life, I would have been a travel planner. So I'm detailed. I'm like, what do we do in the morning, afternoon, etc.? Let me go do six hours of research. I want it to be special. She's vegan, vegetarian friendly. We're going to Vancouver. She lives in Bainbridge, Island. And I was like, and fuck it. Let's build an app. In 15 minutes, I had a fully functional app uh with logins for both of us that she could log on and for each day look at the activities, figure out which one, and she would heart it. And then I will heart it, and then when it hearts together, we'll auto-schedule and deploy. And it's so good that I'll probably use this for any travel plan that I do with a group of people. Do that in 15 minutes.

SPEAKER_02 27:48

Yeah.

SPEAKER_00 27:48

And if you think about all I wrote my latest post was like, you know, what's the last remaining moat in software? We could argue in the SaaS era, even at Outreach or the rest of it. Like when you were the second player in a given category in SaaS, there was no moat. The moat was execution. Do you execute faster than somebody else? Um, do you are you able to hire just better people, right? Who go hard?

SPEAKER_05 28:11

Difference between outreach and sales off was who's executing better at the moment.

SPEAKER_00 28:14

Yeah, who can go hard?

SPEAKER_05 28:15

Yeah.

SPEAKER_00 28:16

Right. Um, and product matters, but a lot of it was tied down to like sales, so how effective your sales and marketing was, and you need a good enough product to enable that.

SPEAKER_01 28:25

Yeah.

SPEAKER_00 28:25

We're now in an era where like if your product isn't on par like every 30 days, sales and marketing breaks. And so in that world, and what defines a winner? Like before you'd be like, oh, I built this little wedge, I raised seed financing, I got to a million, million and a half dollars. Now I've raised 20 million. Now I can build another team, I can build good market, now I can hire another scrum team. And there was just sort of this, oh, I found fit. Now I'm scaling.

SPEAKER_02 28:56

Yeah.

SPEAKER_00 28:56

So like you got fit, you know, like as if like you were two years old, and then you're scaling.

SPEAKER_05 29:01

So it was kind of like this.

SPEAKER_00 29:02

Yeah, and then you were like, oh, I gotta add another product and another product.

SPEAKER_05 29:05

Yeah.

SPEAKER_00 29:06

Now that's all gone.

SPEAKER_02 29:07

Yeah.

SPEAKER_00 29:08

Now it's like, I kind of have fit, I gotta find fit, I gotta find fit, and I gotta find fit. And the rate of change of the value prop of your product vis-a-vis your customers and how you communicate that changes like every 30 days. So, like in that world, I kind of look for psychos. And you hope they're good psychos, not bad psychos. I mean, I I say crazy people.

SPEAKER_02 29:32

Yeah.

SPEAKER_00 29:32

You know, or back to Steve Jobs, you basically say, you know, that's the crazy people. And I've got a limited amount of time to figure out if they're good, crazy, and bad crazy. And sometimes, most of the time, they're good crazy.

SPEAKER_05 29:42

How does that crazy show up? Like, what's an example of that? They're just building stuff already, tinkering, they're clearly.

SPEAKER_00 29:47

Well, first of all, I just this world in the past where you could have a technical founder who has to find a business person, or there's a business founder and hope they have a technical person is over.

SPEAKER_02 29:57

Yeah.

SPEAKER_00 29:57

Founders building.

SPEAKER_02 29:58

Yeah.

SPEAKER_00 29:59

Because unless you're building and using these tools, you can't have a clear point of view of not only what the offering you're bringing is, but what's the operating system, you know, how you're running your company differently. Um, you're on a lot of the time. We talk on weekends.

SPEAKER_02 30:17

Yeah.

SPEAKER_00 30:18

You are ruthless and relentless about execution, but you're always humble that like what you're doing is probably only good enough. And you're looking ahead. I remember there was this conversation. I didn't know he got it from Tony Robbins that's how it races. Mark, when I would come to him, I ran product for a while after I was running go to market at Salesforce that let the inmate run the asylum. And I'm all about priority, you know, as an ops guy, I'm all about priorities. We got X amount of developers. We make some priorities, let's make some hard calls that have 30 boats of three. That's not gonna move the needle. At the end of the day, I just need to give the sales and marketing team one big thing that they can live with. And I would come to him. And I'd be like, look, we got to fix forecasting for the fifth time. A PRM doesn't work. Uh we gotta, we gotta refactor the fact that there's 15 ways to call a document, an attachment, a content piece. And and Mark would be like, no, no, no, we gotta build out the platform, we gotta build a programmatic code, visual force, and declarative and the rest of it. And I'd be like, Mark, nobody's asking for that.

SPEAKER_02 31:21

And he would say, Brett, don't overestimate what you can do in a year, but don't understand what you can do in a decade.

SPEAKER_00 31:28

And was he right? I mean, like Salesforce took a metadata customization model and a lot of like you know, sales admin love to multi-hundred billion dollar evaluation, right? Yeah, and so I think that now has been brought on the AI world, maybe down to like don't overestimate what you can do in a month, but don't understand what you can do in a year. They're constantly thinking that way.

SPEAKER_02 31:49

Yeah.

SPEAKER_00 31:50

Um, and they're thinking about what I will say to them you have to pick the right moment. When it's at seed, it's a little early. We start getting serious, you know, they start getting to like five, ten, fifteen, twenty million. What is what is your right to play? Like what are table stakes? Yeah. That last post basically what I thought was the right to win just became table stakes.

SPEAKER_02 32:12

Yeah.

SPEAKER_00 32:12

And then what do you believe is your right to win? It could be wrong, but what is it that you believe? And that should be imbued across the company. And let's just drive that hard. Yeah. And that's definitely true when you think about your go-to market solve for investment. It's a hard place to invest. But like you look at Gong versus Chorus or these versus that, these were people that just like had a vision, had a mission, and you know, build a movement. You know, you gotta be the pie piper. It's hard. So that's how I think about it.

SPEAKER_05 32:39

Um what about vertical versus horizontal?

SPEAKER_00 32:42

Yeah, I mean, we tend to do more vertical, more vertical.

SPEAKER_05 32:44

Like, you know, you you talk about go-to-market investments, and to me, most of that's in the horizontal category. And you know, we quite frankly haven't done a ton of horizontal either. Because it's hard, it's very hard. The motes are uh collapsing, it's super saturated. There's no context. It's really hard. You know, I I I I I kind of like go back and forth on the whole vibecode thing where it's like, okay, cool, you can vibe code like add-ons to your current product, you can vibecode um, you know, interactive decks and stuff like that now on lovable, but like, you know, there's a reason why people use DocuSign. Like you could use a PDF viewer and send us an attachment in the past to sign a document. You didn't need DocuSign. Use DocuSign so it holds hold up a core. Right. You use it because it has digital fingerprint technology and things like that that allow the document. Well, you also just trust it. You trust it. It's it's nine dollars a user or something like that. Like, am I really gonna go hire somebody to build this themselves? They have to manage it. They can't do it. And I don't want any break.

SPEAKER_00 33:42

And I don't want any innovation.

unknown 33:44

Yeah.

SPEAKER_00 33:44

I don't want 15 new. You know, Zoom keeps throwing out these new things. Like, Zoom's great. Zoom, just be Zoom. Yeah. What's all this popping up stuff on?

SPEAKER_05 33:52

So I guess the the question is like, you know, if you're if you're Salesforce, your HubSpot, some of these horizontal platforms, you know, how big is the worry from, oh, somebody's gonna vibe code their own CRM, somebody's gonna, you know, like is that is there a worry there for those types of companies? Is it the Monacos and the Days and the Adios and the Zeros and numbers?

SPEAKER_00 34:14

I see every one of those. People assume that I'm all in on AI CRM and I'm like, it that's that's a bloody battle. Eventually at some point, yes. I think the biggest challenge to Salesforce and to HubSpot is if you think about the value of those franchises, it is the metadata customization model. It is that somebody went in, customized, put in their logic and their stuff, and then the integration, and then the rules and the alerts and the rest of it. If you have gone and used Claude Code and you watch it assemble a set of agents for you and you tell it what you want done, and it just goes and does does it, yeah, that's not the metaphor anymore. Nobody goes in and sets up rules and workflows and alerts. That's gone. And the entire ecosystem around that, which is, I don't know, what do we got to say? A couple hundred thousand professional services people around the world, around those two ecosystems. Now, for that reason, they're fine. You're not gonna see existential, you know, churn. But I think they need to remodel, rethink through what is the experience for which what I call, like, who has the context? You know, my entire career after business school was working at companies that went to people and said, you should not build this yourselves. We understand this. We've been spending time at SFA or CRM. Oh, and then we've got the vertical edition. We know how it works with banks, etc. And then you go to them and you say, okay, it's gonna take X to implement. What does that mean? You're asking them their context. How do you run your business? What matters to you? What data do you care about? And an SI guaz and this user testing and the rest of it to put it in this database. That's a stupid idea. So, an area I've been looking at, quite frankly, is I think AI is very much coming for that. Because look, if I'm deploying Salesforce, I should have AI understands the schema of Salesforce, what all the objects are. Um, I should know it kind of by your insurance company, et cetera, et cetera, and be like, okay, well, da-da-da. Give me your documents. This is like your business process. I should be able to ask you a couple of questions, et cetera, et cetera, and just deploy it for you. So, what is, if you will, what I'll call this entire ecosystem around Salesforce that keeps and also keeps it going, the admins, the dream force, the knowledge, the trailblazer. Um, in the end, maybe the boat anchor.

SPEAKER_05 36:54

Yeah.

SPEAKER_00 36:54

That's the thing.

SPEAKER_05 36:56

But also the thing holding it down, but maybe the last to go type thing. Yes. It's it's it's just a crazy world we're living in right now, where you know, when I was uh when I was probably my daughter's age, so six, um I one of the creative activities my dad would do is we would type a story together called Darren and Eddie. And my daughter's just starting to get into that stuff now, like write her own stories and she's writing them out. And the other day I'm like, oh man, like I should teach her how to type this. And then I was like, wait a second, typing is the thing of the past.

SPEAKER_00 37:29

Are you a Whisperflow guy?

SPEAKER_05 37:30

Yes.

SPEAKER_00 37:31

You are? I'm not. I it's funny, I went, I'm a writer. I mean, I and people are like, what skills in your career? I'm like, I'm a writer. So I like to write. And so in writing, although we'll talk about you know, people can catch the M-dashes in my writing. I've got editors that help me now. They're called AI. Yeah. Um but that's how you clearly. That's how I that's how I think about my thoughts.

SPEAKER_05 37:52

Yes. So that was the thing. It was like, do I teach her to type, even though typing is going to be obsolete because everybody's gonna basically speak into some inner.

SPEAKER_00 38:01

I think you teach her to type.

SPEAKER_05 38:03

Or, you know, do you write it? Do you do cursive? That works a different part of the brain. Like different things.

SPEAKER_00 38:07

Remind me, remind me how old you are.

SPEAKER_05 38:09

38. Okay.

SPEAKER_00 38:11

So you went to college at the time and was the beginning of uh de-emphasizing humanities and overfunding all STEM programs.

SPEAKER_05 38:19

It was 2005 to 09.

SPEAKER_00 38:21

Yeah, my son, especially, right? I sent my son to Stanford as a top STEM kid out of high school and he came out like a Fulbright scholar. She knows everything about genocide studies. I'm not sure what happened. Um, but it's fine. We need somebody to help us, you know, save this world. But if you really think about what's going to be the dearth of hiring in some of our, and I have this at some of our AI companies, is I need really smart liberal arts majors with agencies. People that think. Think. People that are, think about what you're doing. You're asking either today in the jet PBH an assistant to help you, but in the in the I'll call the Claude Code uh open AI codecs world, you're actually giving words to direct. And you be intentional at the words and what you're directing and how you're and then you're managing that. Um that's not coding.

SPEAKER_02 39:11

Yeah.

SPEAKER_00 39:11

Right? It's actually outcome and thought-based. So it's very interesting. So there was always this thing that A16Z do uh Andreesen would do about make, you know, like I don't know, shape rotators and I don't know what what it was, but it was basically like STEM kids making fun of like MBAs, I think is what it was.

SPEAKER_01 39:28

Right. Okay.

SPEAKER_00 39:28

Yeah. Um he thinks the classics people are gonna have to come back then.

SPEAKER_02 39:32

Yeah.

SPEAKER_05 39:32

So I would never I'd have a right. I'm in the same boat. Uh you know, do you type, do you write, do you cursive, all that type of stuff. But I I agree, like no cursive. Cursive's ridiculous thinking.

SPEAKER_00 39:43

You you ever write a card now and cursive and your hand hurts? Like, what the hell is this?

SPEAKER_05 39:47

I've I literally only use cursive to like sign my name, right? Like, I don't think I've ever I ever use it or read it. Or we spent so much time learning it when we were kids. So, you know, just like trying to think through because they're so young, like, where is this all going? What is the knowledge work that's gonna be available to them in 10 or 15 years when they're in the workforce? It's a trip. I've never had this much anxiety uh trying to stay ahead of the curve.

SPEAKER_00 40:14

It is a very interesting time to raise young children.

SPEAKER_05 40:17

Yes, it is. It is. Um, but what better place than Santa Barbara, California? So they'll be outside. They'll be fine, they'll be outside. Yeah. All right, so we're in this kind of AI era, what we'd call 2.0, 3.0 at this point. Definitely test 1.0. I just called the agent era. Agent era. How does this change how a go-to-market's been done?

SPEAKER_00 40:38

Well, one thing I've been saying for a while now is that to some extent, your success as an operator and my success as an operator was we're the king of explaining. So if you think about SaaS or before SaaS, there were software products that were primarily CRUD databases that had workflows. If we were selling down market, we would limit the screen in workflow so it was easier to understand. If it was upmarket, there could be a bunch of configuration. But these products never actually delivered the end value. They were always like, you could use this such that you could achieve this goal as a business. And so your entire go-to-market organization, from marketing to SDRs to SEs to reps to implementation to CSMs, and was all town to explain it. Because the product in itself didn't do the job. You could use this product to help do the job to be done, but it was it didn't do the job. So when the product you're selling now does the job, well, heck, we can remove a lot of explaining. It's much clearer. What do you want to get done? Let me show this to you. Look, it does this. Now you have to explain it, does it better than two or three other competitors? Let's get going. So, in that world, what happens to like a website that somebody finds through SEO? They hunt and peck across, they grab some content, maybe they do give you your contact info, and then it goes to an SCDR to qualify, and then an AE goes and talks to them, or somebody Chili Piper to bypass the SDRs, and then, oh God, we don't know what a stage one to two is because AEs are inconsistent of accepting an opportunity. And then an AE does a bunch of discovery, and then an SE comes in and does stuff. And then if it's an enterprise deal, we bring in professional services to come and do it. And then we tell the customer, oh, remember, you have this event, there's a real business event. If you don't buy now, my services people aren't. And then you deploy, and they're kind of happy, and you track success around whether they log in or not, and then some poor CSM is supposed to show up and do a QBR to speak to the outcome. Oh, they're not getting the outcome because they're not using the features they should be using.

SPEAKER_05 42:56

Are you talking about W-shaped or U-shaped? Yeah, exactly.

SPEAKER_00 43:00

Like, that's all gone. Yeah, yeah, yeah. That's all gone. And I'm thrilled about that. You know why? Like for years, I would people be like, what should we do, Brad? I'm like, let's just hire an STR. And I would just like throw the iron on. And now somebody asks me, and I go, shit. Just think about that. I don't know, which is really fun, right? Um, so that all changes. And so then the question is, well, what is true? Here is what true. The best go-to-market organizations versus another one did this better than the other. They're able to communicate to the right ICP that the problem they have is a real one, it is urgent, and and what they care most about, we solve more effectively in the competition. And then the value that we're offering for it is worth the problem that it solves. That's been true for 30 years. I still did that's still the core. So the question within that core what changes? Well, you're Showing product much earlier. So AEs or salespeople that understand how product work or the rest of it signar. I mean, unless it's like some custom platform with a four-deployed engineer, you're talking about some theoretical thing. Deployments often happen before you close. Is that pretty interesting? If you can deploy the somebody's like, well, I don't know if this works. What if we just turned it on and I'll give you whatever, a 60-day out? Now you don't do that for customers that you know you can't serve. Bypass procurement, get going. And then deployment, there's not this long deployment, right? So, like, that is what everybody's sort of re-understanding and what those skills are. And then, secondly, for the humans that you haven't involved in that, all the stuff that we wish people did, and entering stuff in Salesforce or doing account plans or doing White's house analysis, or God forbid, just do some research for you get on a call. Well, that's just automatic. That's just provided to you automatic. So all the lazy tendencies is automatic. Now, I will say there's a little bit of anxiety. If you now know that AI can bring you all the information so you can have the perfect call, the perfect interaction, there's this anxiety that you see. So it's kind of really cool. Now, I will tell you what still is true. In this world where there's so much agentic, face-to-face really matters. Especially now, maybe in five years it doesn't, because most of the people buying in AI right now are like, your buyers are like, okay, you know, I discussed this before. People only buy for two reasons greed or fear, right?

SPEAKER_05 45:31

Yeah. And they're still buying from people, are still buying from people, at least right now.

SPEAKER_00 45:36

Still buy from people. For now, I'll tell you something that's a little scary. Um, and they're trying to betting their careers. They don't want to be replaced by AI, and they're basically saying, can I trust you? And it's really important because I'm not just buying the product you have today, because the product in six months is going to be 10x better than the product you gave me today. In-person events matters a lot. A lot. Weirdly, events are back. Like in my vertical software companies, events probably create 75% of the pipeline, at least in the first two years.

SPEAKER_02 46:04

Yeah.

SPEAKER_00 46:05

And then I think brand matters. I think that's probably why you're seeing these uh later stage VCs just writing large checks. They're trying to king make. Right? That's the thing. And there's just crazy stuff happening. And it I'm just trying to digest over the last 40 to 50 days, which is if you really dig into using Claude or Codex and you give it planning on your go-to-market, and then you let it go execute the stuff that doesn't require a human, and then get better where it's failing, as long as you've given it context, um is a little mind-blowing.

SPEAKER_05 46:43

Pricing and packaging is often a part of go-to-market that I feel gets left out of the conversation. It's like the most important one. Exactly. So do you do you think that now we're kind of definitively in a phase of PLG, um, has seat-based pricing died in? If we're not in PLG, now we're moving to like platform plus consumption model or credits only. Uh, you know, if you're a founder or you're, you know, helping coach founders, are you trying to shift them in in one direction or another for Look?

SPEAKER_00 47:16

I think it it matters by Nuance. It matters by which vertical which customer. Pricing and packaging should always reflect two things. One, if you explained it, does it seem fair, make sense, the unit of value you're doing, right? And then two, does it inject just the right amount of friction? Like there are businesses where founders have been trying to do annual contracts up front that's just adding friction to make VCs or happy, which is ironic because now we're going to get to a world where ARR is not a thing, right? Um, and then PLG, like my sense is we often think of PLG as a go-to-market motion. It can be if you're self-serve, but at the end of the day, I always thought of PLG as here's what's very interesting about AI products. SaaS products, PLG was hey, we're serving a non-sophisticated organization or a smaller organization that doesn't have IT, doesn't have sophistication. So we have to hide all of that. And we hide that in our UX and what we give so that they can come in and start to use it on their own without any foresight, knowledge, et cetera. Yeah. And then at some point, those companies like, I don't move up market and hire reps and the rest of it. But in my mind, it was always the case, even if I had an enterprise sales organization where I was focused up market, if I could have a product that somebody in the org could experience and understand the value of and have delight before I was trying to sell them and upsell them. It was always helpful, right? What's usually in AI is this delineation goes away. There's no such thing as simplistic. There's this thing as like an easy-to-use product that's simplistic for non-power users if you think about sales loft, or super sophisticated for smart people who really want to like like outreach. No, you just tell me what you want to do. And I will do what you want to do. You want to do simple things? Our product is simple things. You want to get a little smarter? And the great thing is in an AI product will be like, hey, you're doing this, this, this. Hey, do you want to try this, this, and this? And we'll do it for you. Like, so this is all gonna break down.

SPEAKER_02 49:18

Yeah.

SPEAKER_00 49:19

What's very interesting is what you're seeing in AI companies is PLG motions for large multi-hundred thousand dollar sales.

SPEAKER_05 49:26

And is that is that because they're using, you know, FDEs basically, or no, this that's not PLG.

SPEAKER_00 49:33

Well, they're that's that's person-led growth. That's your Person ledged. No, this is the you get into an org, somebody starts using it, it's like, wow, this is really good.

SPEAKER_05 49:42

So you're saying those are the instances where it just spreads like wild personality. It spreads like wildfire, right?

SPEAKER_00 49:46

And they go, okay, let's go do that. Um, and then this the other PLG is, you know, FTE's person-led growth.

SPEAKER_02 49:52

Yeah.

SPEAKER_00 49:53

Um, which look, I think what's happening there, you and I think it's more a it's a phenomenon of the last two years, in that there were holes or gaps in what the model providers provided. And there was holes and gaps of what people wanted to do. And so if you could go in there and you could understand the problem and you could assemble, if you will, an ontology layer that worked for the company and found a use case, then you could rip. For me, whether right or wrong, I'm an intentional, I've always been intentional. That doesn't reflect intentionality in my mind, but um, it's work for some firms, right? Um, so that's how I think about what go to market is changing. And I think the interesting thing is that like my first job at Salesforce was I was the first, we weren't, we didn't call it then, was RevOps. Yeah, I was hired to be like, all right, well, what's this model? Let's define this SaaS model. And and, you know, Brett, where where do we hire the next hundred people and and go to market? What do we go do in what segment? How do we, you know, all of that? And that business grew where I had like systems, sales enablement, product marketing, whatever. Like, you know, at the end of the quarter, I would like yell at the RBPs. It was like some, they yell at me back like some episode of Hugh Good Men. You can't handle the truth. I'm like, you're getting your ass kicked. Right. Um what I'm seeing now is functional leaders instead of like, you know, we'd interview it's like, well, is he a process guy? Is he a system guy? Does he do a forecast? No, he's a good sales or deal guy. Um, I don't think you're a functional leader and go to market unless you're building. We have a guy from Salesforce who was super successful, Angelo Garcia. We just put into one of our companies, James Cakis gave the intro into Octave. He's been building on day three. He's just in there building. He's taking Octave, he's taking clay, et cetera, and he's just building. Because how are you going to go run the org and who you need to hire and understand where I want humans and where I'm going to use agents unless you're building?

SPEAKER_02 51:51

Yeah.

SPEAKER_00 51:51

So I think the world of like the old-fashioned, um, really nice haired, you know, um smooth talker, smooth talker, really good manicure, pedicure, yeah, class ring has that go-to story.

SPEAKER_05 52:04

Yeah.

SPEAKER_00 52:04

I think it's time for them to like just enjoy the enjoy. They had a great run.

SPEAKER_05 52:10

Yeah. Enjoy your libbing. Awesome. Last question for you then. Um, what happens to VC in this kind of new era?

SPEAKER_00 52:18

Well, look, I think it's money. Look, I think it's something, I think it's something really interesting. Look, I think VC goes through evolutions.

SPEAKER_02 52:25

Yeah.

SPEAKER_00 52:26

Right? You know, the last 15 to 20 years, look, we invest at the application level. We're not infrastructure investors, hardcore, data centers, et cetera. You know, and and to some extent, there has been sort of a model. The SAS model, we've come up with metrics, the magic number, you know, the cash burn, da da da da da da. If that is no longer the way software works, we need to revisit what are we investing and how much capital is required. You know, we were raising this fund 18 months ago, started raising the fund. And I'd put out a piece that said that 75% of customer-facing software applications would disappear, and 50% of application software categories would completely go away. Now we were able to raise because the thesis was we were ahead of that curve a little bit and we would pick. Um so when we think how VC changes, um, it's been weird, right? If you look at VC right now, like 80 to 90 percent of BC has been raised by like six funds. And to some extent, they were either like in anthropic or in open AI or et cetera, right?

SPEAKER_05 53:31

And recent lightspeed drive index.

SPEAKER_00 53:33

Yes, yeah, but and they have a ton of money. They make a lot of money on fees. I'm not saying they're not good investors, but for them, they need to invest those dollars, right? Um, you know, we're a C stage investor. Um we make our money off of Carrie. You have a lot of funds, early fund one pre-seed people. These aren't people that are like putting their kids through college, being a venture capitalist. It's only on Carrie. And that carry 20 years ago used to be at Salesforce, SIBO went public at 40 million revenue. I think Salesforce was like 100, it would have been earlier, but we said something about the dollar llama, and we need to wait, we needed to wait a year. Now they're not going public until like multi-billion dollars.

SPEAKER_05 54:16

Yeah, right.

SPEAKER_00 54:16

And so, unless you're selling secondary along the lay, it's a long thing.

SPEAKER_05 54:19

So you had Bill Bench on and he said Marketo, I think was like 82 million or something like that.

SPEAKER_00 54:24

Right.

SPEAKER_05 54:24

That was in the 2010s. Right. I mean, how fast it's changed.

SPEAKER_00 54:29

So, and so you gotta do this for the love of the game. Yeah, right. I think what is interesting is I suspect that we'll see more investments in what I'll call non-consensus bets. Because, like, if everything becomes easy to build software, then what are you investing in other than a phenomenal founder of judgment executes? And there's still that. It's hard to identify that at the early stage. It's easier to identify Series A B C. And so I think you're gonna look for stuff that's quite hard and remember what venture capital came from, right? The regional venture capitalists were the people that funded the ships that left Portugal and Spain for the new world to come back with riches. But most of those ships were lost at sea. But if one came back, it turbojacked that economy for like 10 years. You ever go to like Portugal or Amsterdam and you're like, what why are these towns here? Like they put they sent out a lot of ships and you have to be ready for things to fail.

SPEAKER_02 55:28

Yeah.

SPEAKER_00 55:29

Which is, you know, you're probably the same as I am, which is an operator. We're trained that nothing could fail. We know our report card at the end of each day, we fix stuff. And the challenge adventure as a former operator is just understanding that. Like, if you're investing in the right things, right? Where it's the alpha of the one deal.

SPEAKER_02 55:47

Yeah.

SPEAKER_00 55:47

Power. Seven out of ten should die.

SPEAKER_02 55:49

Yeah.

SPEAKER_00 55:50

Um, so, anyways, we're in the middle of forming our thesis around what we're investing in. You know, we've done a lot of vertical, we've done, which has been very helpful to us. It's very defensible. And AI helps accelerate. Because the interesting thing about vertical companies versus horizontal, which is customers are much more willing to give you all of their workflow. And not only their workflow, but if it's an interconnected system where there's like a whole, if there's like, if there's a multi-chair supply chain or demand chain, and if you've built this ontology system across those things and you've given it meaning, and now somebody gives you clawed code, well, hell, you can deliver amazing stuff. And so a lot of really exciting stuff is the non-sophisticated buyer.

SPEAKER_02 56:31

Yeah.

SPEAKER_00 56:32

Right? We have a lot of companies where they're very successful selling software to buyers who have never used software before because it makes them more successful. Yeah. So, like we're an investor in a company called Supio, that's one of the rocket ships in personal injury law. These people did not use software before.

SPEAKER_05 56:48

And now they hit one button.

SPEAKER_00 56:52

Well, it's not one button, but if you think about it, if I'm a PI firm, think about this. I used to, there's a whole franchise where I outsource half of my cases where I sell my cases that I can't handle.

SPEAKER_02 57:01

Yeah.

SPEAKER_00 57:02

They don't have to do that anymore.

SPEAKER_02 57:03

Yeah.

SPEAKER_00 57:04

And then two, I get paid on the outcome of the verdict. And if AI can basically make sense of every single artifact or document that matters, understands the way in which I like to practice law. So I can process more cases and I can generate much more revenue.

SPEAKER_05 57:22

But do you think a company like that needs less money over time? They hire less people because they're using their own law firm. No, it should be it.

SPEAKER_00 57:31

One can argue right now, given we're going for agentic less, because I think the reality is that a bunch of the AI companies are working right now had to invest a bunch of people in infrastructure to fill in the gaps where the models weren't. So that goes away. You don't need as much human to live.

SPEAKER_02 57:47

Yeah.

SPEAKER_00 57:47

Two, um, you definitely, as a percentage of what SaaS people would be, the number of people you need in the organization, agents versus human, changes. We need less people in these startups. That being said, I said this two years ago. I think we can get packed to win or take all. So the question is what amount of money are you willing to spend to create missionaries, either working at your company, et cetera. Because, like, I just I'm in their Slack feed, they'll let me in. Hey, this guy, one of the reps, drove 65 miles outside of downtown Baton Rouge to the regional PI firm that handles the PI in the area, dropped off donuts, built a relationship with them, and that's now an$80,000 customer. Yeah.

SPEAKER_05 58:30

I did that in Salt Lake City once.

SPEAKER_00 58:31

Right. For outreach. Right. So I don't know. What I do know though, in running these companies, like if you were back running, you'd probably, oh my God, I should go back to build or run. It's a lot purer. Because you used to spend time, I used to spend my time. I had SVPs that AVPs worked for, the VPs work director, and there were different functions. I felt like I had to go like a cover, undercover boss to figure out what the was actually going on. Yeah. And I would have meetings, not to have meetings, but to look at people to understand if they were aligned or not. Dude, I could wake up each day and my version of ClaudeBot and tell me what's going on, who's not working together, what's going on, give them advice, give them guidance, et cetera. Like there's no mysteries.

SPEAKER_02 59:12

Yeah.

SPEAKER_00 59:13

Uh, which is super exciting. I hope the only downtime is I'm not sure when you stop. Right? Because if, you know, like if you could be, you know, we still need humans, still need, unlike Asians, humans still need downtime.

SPEAKER_05 59:26

Yeah.

SPEAKER_00 59:26

And that's why you and I are in Santa Barbara.

SPEAKER_05 59:28

Yep. Well, thank you so much for coming on here. This is amazing. Great. That was another fantastic episode of the VC series on the GTM Now podcast. Head over to Apple, Spotify, or YouTube and give us a like and subscribe, and we'll see you on the next one.