Well, today's conversation should be a lot of fun. I've got Brett Queen here with me. Brett is a partner at Bonfire, one of our favorite co investors. Before bonfire, Brett had a very impressive career. Most notably, perhaps as the head of Salesforce's product and marketing teams. Brett always has a lot to say and is not shy about sharing. So I'm looking forward to some great stories and knowledge from you, Brett.
I'm excited to finally be on this podcast.

Well, I'm excited for it too. So, I thought we'd talk a little bit about Salesforce. I find it super interesting how you got this role and what was going on at Salesforce at the time. And then of course, we'll talk a lot about Bonfire and what you're doing today.

It's always interesting. You probably have the same thing many when people look at your career and are like, wow, how did you chart out your career? You were really intentional about your career. It's actually not the case. Out of Dartmouth, no one wanted to hire me.

I guess I was just a little direct, except Tom Siebel from Siebel Systems chose to hire me. direct
He's very, very direct. Yes. Uh, so I worked with Tom for about six years, you know, and for those who don't know, this is back in the day when software was shipped on CDs,
So I worked at Siebel for a while. How do I put it? Tom and I had a falling out. And uh, I think about the same time Mark and Tom had a falling out.
I think Tom was somehow involved with salesforce.com. I think he wanted it to be a business unit I don't think Mark wanted that having worked for Larry before. And so I went over to Salesforce because they knew a lot about crm.
think,
And after six years at Siebel, I made the mistake of going to see an alumni from Dartmouth speak, who's the famous [00:02:00] TJ Rogers of Cypress Semiconductor. And I was in the audience, and he's very brash, tj. And he said, people, I've got one word of advice for you. He's like, in your career, you either make shit or you sell shit, or your job is bullshit.
And I was like, wow. I'm an operational person, my job is bullshit. But then when I met with Mark, and at the time Salesforce was probably around a couple million dollars in revenue. Wow. Had less than 10 reps.
primarily smb, and they'd hired their first enterprise rep.
And when I looked at what Salesforce was doing, I had a thesis. I was like, for the first time in software, you could potentially sell direct to every segment of a market.
If you got the pricing and packaging, the demand gen and the sales model down,
and
just
weren't selling direct?
No. Direct was an enterprise. Uh, downmarket was VARs and really Downmarket was packaged. VARs, VARs,
I remember.
Uh, and then down Downmarket was at Fries. There's big, remember [00:03:00] Coel and all those companies, you would go and buy it at your local fries.
That's a, for those don't know, that's Prebes buy
So you said you can not just do Enterprise
Direct,
you could sell direct in every segment over time.
And as long as your retention was strong and you figured out new products to sell customers, you could basically create a cash machine.
That was the thesis. Mm-hmm. And so you ended up running sales and marketing
so,
the first, call it three to four years I was paired up with a gentleman named Jim Steele who'd come from Reeb and ibm.
And it was really about building out the go to market model. Like how do we think about who are we hiring, where are we hiring, segmentation, pricing, packaging, product marketing, competitive, et cetera.
so that was probably going from about 5 million to about a hundred, 150 million in that stint. At that time I sat down with Mark and I was looking at this beautiful model and I was like, you don't need me, like I should go do something else.
He said, well, what should you do next? Like, what are we not getting right? I'm like, well, we have an SFA product. It's already too [00:04:00] sophisticated for smb. It's not, sophisticated enough for enterprise, And having come from Siebel, I knew the SV market was good, but the call center market was as large analytic markets, et cetera, et cetera. And so I said, look, we only have about 40 to 45 developers. Most of the product is written in Peel sql. 10 of them are doing custom stuff for on-premise exchange server from Merrill Lynch.
Like I think we need to kind of like have a real product strategy here about how we go create these multi-billion dollar business lines. Because look, the rule of thumb and SaaS, I think it's true even today, and this is the challenge with companies that in the last couple years have gone public and have not done well, which is if you don't have a clear intentional strategy to be able to hire, grow your reps 30 to 40% a year capacity wise, you don't have enough product or market opportunity to demand to go do it.
You can't deliver to the street 30 to 50% growth, And so I said, that's what I should think I should do. thanks very much. And then I got a call and he said, okay, you run product. Which was kind of interesting cuz at first the engineers and product people sort of thought it was like the, what do you call it, the fox and the hen house, the sales operations person coming over to [00:05:00] run product.
Yeah. so I did that for about four years and built what we called the GM model at Salesforce where we would have leaders. A lot of them were acquired CEOs who was like, you need to go create a billion dollar business line. the big one I really spent time was with the contact center at the time.
There was a company called right now with Greg and his great right-wing politics in Montana. and we were like, we're gonna go beat right now. And that's now the biggest business line for
Salesforce
Interesting that you were doing it with acquired CEOs. Yeah.
And then we started buying larger companies. So as part of this product strategy was what do we build by or partner? And the reality was
we only had so much capacity. And at the same time we also built, launched the app exchange, right?
With the idea being that there's no way we could go build all this ourselves.
you were going from one product at Salesforce. To many, many products to becoming a platform.
Do you talk to your portfolio companies about transitions like this?
We do, but I think it's stage appropriate. Sure. Right. And look, you invested very similar stage at us, which [00:06:00] is from seed to A is really hard.
Right.
And so from C to A, it's very much do not think about product two, product three, product four, product five. We need to basically, you know, prove product one.
So you're
not,
I think you said something like you're not a fan of experimentation.
Yes and no. I'm a fan of intentionality, so like this concept of the lean startup where we just sort of figure this along the way and we ship features every week, et cetera. I just don't think there's time and capital to do that. Within sort of the 24 to 30 month window, our companies and 10 have, where you take this seed round to get to a Now what I do believe is that you need enough time in capital to make a lot of mistakes. Right? The most important thing in the calls they have with founders, you know, I'll be on a call with the founder like, oh yeah, de this is not going well. This call, this call went really well, da, da, da. And then they move on and I'm like, wait, stop.
Let's talk about that call. What happened on that call? Oh, write that down.[00:07:00] so it's so important from C to a, You have to go through the quick learning loops. Like how quickly can you try something and quickly, okay, that didn't work and we stop.
Like the idea at Salesforce, like when we, at Salesforce there was no playbook, there was no SAS playbook, Venture wasn't even that involved in sas. You know, one of the reasons Mark and Tom and others have made so much money personally is no venture people would give them a lot of money.
They thought these were crazy ideas,
Yep.
but what did we do? We were like, I don't know, we have these two paths. These are the two options we had. This seems to make sense. How would we measure it? We check in 30 days like that worked. Let's do more of that.
Well I like hearing your rules of thumb. Yeah. I think it's interesting cuz Salesforce was creating a lot of this go-to market
motion.
Yeah. And
so what you said you have to be able to hire 30 to 40%, uh, more AEs or something more salespeople per year.
I think you said 20% of your workforce has to be
quota carrying.
So one of the interesting things. We've quoted a lot of new metrics. We didn't have these metrics before of like the magic number or [00:08:00] the cash burn, da da da da da da.
And unless you're purely product led, which is great, but if you have salespeople selling product, I think it's really important to understand you have two ics that you have to get right at a software company. You have to have great salespeople and you have to have great developers and everyone, including executives kind of overhead.
We are there to make sure that the ICS build great product and the salespeople can

I'm sure many last two years you've sat down with founder, let's look at this shape of your revenue. Let's understand. Like if you have a 25 K as P, that's gotta be pretty inbound. You can't hire a lot of SDRs and it's just not gonna work economically. And now they're listening. But where people got outta whack, which is, I always tell people, 20% of your employees should be quoted caring reps, and 20% of employees should be code reading devs.
And if you can't make that work, oh no, da da da. Or we can't, we don't have enough pipeline, da da da. Oh, you don't understand. We're like, stop something's broken with your
work.
So I think a general rule of thumb is [00:09:00] 20% employees are reps, 20% employees are ics.
Because the challenge is you get below that from a quota capacity perspective, you'll never outrun your expense
And then when you get to a much larger company and you have capital, , I actually think you have bigger constraints. like some dev teams will walk in and they've got 90 developers, but there's 30 scrum teams of three developers and nobody's moving anything forward.
And so I'll say to them, I say, what if you only had three teams of 30? What would you do? Right? Because I think what's most important is not what you choose to do, but's what you choose not to. So I think from a capacity perspective, it's really important.
I wanna get into a lot of your advice
for startups. but let's just ground it in. What Bonfire is
doing, what you're doing today.
So Bonfire third fund, 170 million fund.
We do seed. We don't do a, we don't do pre-seed. We are very concentrated. I know there are many firms, like, let's write smaller checks and we'll get a lot of shots on goal. We don't do that. So we write between two and three and a half million dollar checks. We lead the seed round. And when we say seed, because I don't know [00:10:00] many, but half my calls were founders are like uh, we're raising $4 million.
We incubated 60 days ago. I'm like, well, if you raise that, somebody's gonna own your company, you're gonna raise four and five.
right, right.

why don't you do Prese? We are pretty involved with our firms.
.
Mm-hmm. Okay. And so we'll spend a lot of time each partner, so Mark, Jim and I, and then we have two principals that will do one investment year. Mark. Jim and I will do two, maybe three investments a year.
More likely. Two. We're gonna spend a lot of time with those firms in year one.
And so the challenge we found, we dug into pre-seed was, first of all, when we invest, we're trying to get to a, so we have a very good recipe of knowing like if you've got three to six or seven k a r, there's enough there, there's enough data and signal points where we understand where the kind of the business is, where we can guide them and help them.
and when we ask ourselves, why do we think this company's gonna get to a hundred million dollars in revenue? And somehow in the last five years, everybody thought every software companys get to a hundred million dollars in revenue. It turns out there aren't
go,
right?
There's not enough data points at Prese.
The other reality is, We found, we did some pre-seed investments. We spent the same [00:11:00] amount of time.
right, right.
Right. They actually need more time.
Yes, That of course.
So we do seed, uh, we'll do in this, one 70 fund, we'll probably do 25 core positions.
We do hold at least 50% for follow on. Mm-hmm. Right. And so we'll do our prorata probably to a B, and then maybe in C and d, uh, we have an opportunity fund as well to be able to participate in those.
Yeah. Your B2B only
B2B software only you know, Historically in Bonfire one was raised based on dominating Southern California B2B seed.
based on my two partners, mark and Jim had been investing in Southern California, B2B for a while, and then Bonfire Two and Zoom and the Pandemic, our reputation grew and a lot more investments across the United
too. Yeah, I'm
actually very curious about how you approach expanding and expanding the bonfire brand in different
Yeah. we like to be involved, and it's hard to be involved all virtual.
And it's also just the reality of travel. Right? I did a lot of [00:12:00] investments in bonfire too across the United States and the world, and everybody wants to have two board meetings in person with the dinner the night before.
Yeah.
And my wife's like, what the hell is this? You know We have pre-seed partnerships in San Francisco. But the reality, and you and I talked about this, which is if we see a deal that's coming outta San Francisco, we're not the first eyes in this
dealWe're very strong in New York. We have a number of Investments there. We go to New York quite a bit. And then outside of New York the key for us is to have a very strong local pre-seed firm that we trust, um, that will meet with the founder on a day-to-day basis.
How do you see all the great deals in la? I feel like
it's getting harder.
It's getting harder.
look, I think in LA one, a lot of deal flow from the venture ecosystem. Yes. Right. The lawyers, the pree, the angels, et cetera. And, you know, I think Mark and Jim have very long lasting relationships.
I think, We do bring in younger investors who are more likely to go to all of the events. [00:13:00] Yes. Right.
There are A lot,
a lot of them. And then I think it's founder references, That's
harder.
Right. You know, it's, you know, 10, 1 10 and uh, and bonfire aren't the only game in 10.
I know, I know.
but I have talked to Jim about his love of vertical SaaS because you have such a background in things like sales and marketing and some of these more horizontal things.
Does that change what you're, you know, most inclined to invest in?
. It influences my deal flow. Yeah.
Yeah.
So I get a lot of deal flow and horizontal b2b, go-to market tech.
Yeah.
That's a very crowded area. Yes. It's a tough space.
It's very Bay area.
It's very, it's very Bay area. It's very funded and it's very expensive from a CAC perspective.
Cuz when you invest in this space, there's probably five to 10 competitors that get funded or funded in space.
It's hard at the early stages.
It's very hard. Yeah. Now what do I like? Look, I like amazing founders that are delivering products to people. That when I talk to the customer, they're very emotional about talking [00:14:00] about.
Yes.
Um, when I do customer interviews, I very rarely listen to what they're saying to me rationally.
It's like, do I love this company?
And so honestly, that's what I listen most for. I really listen for the pain on the other side.
I'll invest in horizontal vertical categories. It doesn't matter. You know I do like vertical. What I do like about vertical is that there's less experimentation. Horizontal's, like, okay, which is my icp, across which titles within which vertical, et cetera. And how do I think about the tradeoffs with the roadmap?
So I think sometimes they're harder to crack. But I think once you start getting momentum, um, I think it's easier to get into your flow on the vertical
side.
And are there, I mean, kind of back to these rules of thumb, are there metrics that you start to be able to look at in terms of cac, pay, payback, those sorts of things at the stage you're investing?
Look, talking about CAC is a little silly because if a company's gotten a seven krr and the CO's been [00:15:00] selling and you look at their magic number, they have like one junior person in sales.
And you know this between seed A, if you hire a VP of sales, I dunno, they're not cheap. Let's call it 200 base, 200 variable. If you're lucky and the quota number's a million, Hey, when the quota's 10 million, they're still gonna be paid that. But if you take the cost of the person, it's gonna throw your,
your number
outta whack.
What we focus on between seed and a, and I don't know what you're seeing, but Raising an A feels like raising an a seven years ago, somebody's looking for two to 3 million in ARR and they're looking for the right mix of growth, two to three X growth, and they're looking for efficiency. And so when we're looking at businesses and they give you that financial model where they're like, oh, gimme 2 million.
I'm gonna go to 10 million a r r in a year. You're like, will you'd be the fastest growing software company of all time? let's back that down is, hey, with this capital. can you get the two to three X growth and can you get your magic number? Call it one and a half. One to one and a half, and can you get your cash burned below two?
Okay.
So, okay. But let's
stick on this theme of you're [00:16:00] coaching your seed companies to get to the a.
You know, you walk in, you're talking to, I don't know if they have a C M O, but you're talking to the person who's running the marketing.
How are you helping them think about ramping sales teams and building that muscle?
We do a workshop with all of our firms. It tends to work for us. It's a little nutty, but you know, probably in the first month I'll spend 20 to 30 hours, with the companies.
and you'll do this for all, you'll do this not just for your
investments.
Well, we will each do them.
Okay.
For each
other's. Okay.
But I tend to go a little deeper and we basically say whatever you presented to us when we raise money, that's great. Let's just chuck that. That was wonderful. I know you had to tell us. I mean, we've done diligence, but like you, they have to tell us everything is wonderful.
All right, fine. Let's put that to the side. We're now, we're
married. Yeah.
did the wire
right.
So
Where I will spend a lot of time is on the intersection of messaging and product. which is you have to have a strong belief and hopefully you've got data and customer feedback to tell you this.
Like, what is it [00:17:00] that your product does for who? That they give a shit about. And
it's very funny, I'll run these exercises and I'll ask founders. It's a. I run 'em through it. It's all on our website. You can use the exercise with your firms or anybody can go use it.
And it has, it's just the table. And it says, okay, for this ICP one, ICP two, what does your product allow The people that you're targeting to do new, been able to do this before, do better. They do this today, but better or do more. First of all, everybody wants to do new, which is a problem.
If it's all do new, it's not an existing market. Forget SEO and inbound, because if it's brand new, no one knows they need it. But 90% of the time, founders come back with product features. They describe their product, right?
right? Which is not the customer. It's
not the customer. I agree. And so it's just like, let's be clear on what is it that our product allows these people to do that they care about.
Can we understand that? And the next is, how does it allow them it to do better than the alternatives? And then the next is, What happens if they don't buy this? Now, what is the economic impact? And [00:18:00] this has been really acute over the last year.
If people were selling B2B tech, you know, they're companies that 180% n r now are 60% gross retention.
Cuz everybody was buying a ton
everybody,
And so really trying to align the first product lead and marketing lead and sales lead around this conversation.
Now,
this might be former operators, VC overreach, who's to say, you know, I've, I was at a board meeting after a board meeting, with the Midas list multiple time. And he comes to me and he says, Brett, I've never been an operator. I'll tell you what though, I only have two bullets in the gun. After I make an investment, I have two decisions.
Am I sticking with the CEO or not and when there's a funding or exit, am I on board or not? . Outside of that, I don't really have any bullets. And he said you definitely have a couple more, but not as many as you think.
So.
so, because you're coming in ready to help them rethink their whole messaging product roadmap.
Yes. And I think, you know, I have friends who have been operators who've joined Venture and [00:19:00] I sat them aside and I said, look, I think the key is them think through the framework of how to think through stuff, but not giving them the answers.
And
I think Mark Mullen, your partner, told me that you've come in and sort of productized a lot of
this, these Frameworks. Yes.
But Mark's also said to me, Brett, I've had 25 exits and I've never helped a company one 10th as much as you've helped them. And I said, so I think, mark, what you're saying is we should invest in companies that don't need our help.
Right. That would be awesome.
Right. I know I had, uh, I think it was Omar Haoui said something like, we all say we want coachable founders. We actually want founders who don't need our loan. Right? Yes. Wow. So, okay.
so you've gone through this exercise, you've got the messaging, you've talked about the product roadmap. I mean, many of our companies are going from founder led sales to actually building out a
sales team. Do you talk to 'em about like how many sales reps to hire, how quickly, what sort of motion it's gonna be?
Yeah. I mean, I think a big thing, and I'm, I'm hosting a panel at Saster with three CEOs [00:20:00] and, and It's the top mistakes they've made scaling to 2 million to 10 million to be
asking.
I think the mistake, this is a challenge that most founders have, especially for younger founders, they think that they should hire a professional relatively early on to go scale a function. And that's a mistake.
Okay.
And from C to a, my general point of view is that the founder should have a couple ICS in these function marketing, sales success, and they should work with them.
In
flow of what's working, what's not, until you have a sense of what you're looking to hire. And even when you go hire your first leader, I would say what you want in your first leader in these functions are mechanics, not scalers.
and so we had all these people jumping jobs every two years that are gonna coming in and say, I'm gonna go scale this function. But it wasn't ready to be scaled
yet.
But they weren't mechanics, they were scalers, they were used to scaling another playbook.
And so generally, my guidance for the first leaders, That they [00:21:00] hire under them after they hire the ace ics is somebody who's going to help, I'll say help author the playbook. Mm-hmm. That you can then scale. And these people should be able to get you like in sales to your first 10, to 15, 20 reps.
They may not be the scale person,
but
that's still a fair, that that's
still some amount of scale.
But you've seen this before where a founder has sales, wants to bring in a professional, they bring in the professional, and then they wanna delegate, not be a toxic leader, not micromanage.
especially as a founder, you have to stay close to the pulse of your customer. But so many of them hired CEO people delegated, and then we talked to them and sales have gone down and they're sad.
And we're like, are you, how many deals are you in? Well, they kind of bring me in. Okay. That's not
Mm-hmm.
And so that's a hard journey that we watch very closely now in terms of how many reps to hire. Absolutely. Like I came up with probably the first SaaS capacity model. But I always chuckle when we look through a two or three year financial plan, like somebody gives you this beautiful plan that's got a sales capacity model. Like, okay, well how are you gonna [00:22:00] generate demand for those people? Because the model will be like, oh, this rep's a million dollar quota and we're giving them six months to ramp, and it cascades, and then of course I'm only taking 80% of the street quota, and that's my financial plan.
Sounds great. Where's pipeline coming from?
So much good operational insight. What are some other big themes? Have you guys approaching ai
Okay. For me, as somebody who, I didn't tell you this, but like I had to remind us, mark, when he had me run product and treated me like an ops guy for a while, like I was a dork in high school.
Like I went to Atari camp. Okay. I wrote Atari basic. Here's what I'm excited about. Ui. I think all software applications from a UX perspective suck and they've sucked for 20 years. I think the majority of business, B2B software applications, Salesforce especially, there's a list view. There's a form view, and they basically give you a view into the graphical data that's sitting in the table in their database structure.
That's garbage, that's lazy. And so what I'm so [00:23:00] excited about AI is that for the next five years, I don't believe in any category there'll be a winner in this B2B software category that when you log into it, it doesn't tell you, Hey, here's what's going on, here's what you should focus on.
You might wanna do this, and for these mundane tasks, we will do it for you. I think that's the new normal,
Yeah.
And so, unlike a lot of new technologies, like if you were like an on-premise company in the cloud came, you're screwed.
Or like if you didn't know how to be mobile responsive and you were just trying to throw something on the iPad, you were screwed. There's an opportunity for our existing players very quickly, and I'm seeing some of my portfolio companies to fundamentally change the trajectory of their business.
Yeah. and then the second thing that's really interesting, and we know less about this, but thinking about how much capital, how much people you need to run a software company, I think changes pretty dramatically.
And then obviously on the demand gen front starting to [00:24:00] see really interesting things where you would never think you could go outbound for like a business that, targets solo proprietary.
You would never go outbound. Makes no sense. It has to be inbound. We've got a company called Top Line Pro that sells a product to one to five person, whatever, lawn and garden professional people that goes hard outbound, using generative AI to figure out who these people are, what their websites are, and generated at scale personalized programs that having reps and SDRs actually makes sense.
That's super exciting in terms of me as an operator going, oh, this is a different model.
Yeah.
But I also wonder whether there's also a period in time, like there was a period of time where you could do Google advertising. There was a period of time
And
like we're gonna get so saturated with
all of that. Amazing. outbound Content.
But right now
is
a moment.
Right now is the moment.Yeah. Right. Yep.
How, I'm gonna shift
a little bit how are you different than Mark and Jim?
We're very different.
I know you're very different. How do you describe
it?
did somebody [00:25:00] describe it as? Somebody described it as, mark is the eq. Jim is the iq and I'm the operator. I think that makes me the asshole. I'm not exactly sure. Not exactly sure what that makes me very different and quite frankly, that's why it works.
And it's a job where, like, can you imagine when you were at shift your other jobs where you don't know in your job, let me give you a review in seven years,
Right.
Because then I'll know if you're good. Right.
And so it's really important to have a team where like we have a good culture and we work well together. I think the good news with Mark and Jim is that they've all had, and myself, we've all had successes in our life. We don't do seed stage investing because we think it's the best way to make money. . In fact, it's a terrible way to make money, right? Like you might break even in year six after your
it's to get rich slow.
It's if taxes don't change, you have to really enjoy,
sure
you have to enjoy the grind that the founder has to go through.
And when they get to the other side, feel like you somehow help them on that [00:26:00] journey, that's the reward. It's like raising kids. You just hope they don't hate you. Right?
So what I'll say is we're very different from a personality perspective. I think we're very similar in our motivation for why we do this. And I think we work sort of very well together because we are very different from a personality perspective.
Well, I've always just even thought that the whole sales marketing, or at least sales in particular parts of organizations are sometimes a completely different culture.
You know what's interesting, what I have all my founders do, I don't care if you use Slack or something else.
create one channel in your internal org for Slack. And I want on there, all new meetings booked until it gets too big, all deals won, new hires, et cetera, et cetera.
When a deals won, talk about it. And so what's interesting and then. Now with the advance of recordings and feedback, I can see it. And so anytime I've talked to a founder, I've read all of those and so I can see what's going on [00:27:00] in the deals and I will listen. I, so for me, I need to read the narrative of how people are describing deals, what deals are closing, why we've won, where we lost.
And I will listen on two times speed, um, the chorus or gong calls of
customers.
Because look, I've been doing software for 30 years. This is not a complicated business, okay? You are going to an individual and you are selling them a dream.

And the amount of money you're gonna pay for that you feel like you're getting a good deal out of, I don't care if it's product led or the rest of it. And people primarily buy for two reasons. They bry for fear, if I don't buy this, I'm going to get fired. something bad is gonna happen to me or greed, I'll be better than my peers or better than somebody else at doing
my
And so if I can listen to just humans talking in this cycle, I've seen enough software cycles in the rest of it where I can just say to the founders, Hey, here's what I'm hearing.
And look,I don't think VC should ever overreach. I think, I don't care if you've been operator, [00:28:00] um, or not.
I think our biggest value add is that we are not in the daily grind that the founder's in, And the reality is the founders all have the answers in their heads. But they had the sleepless nights.
And look, if you really break down those as a founder,
though,
what does that break down to? What do I wish I knew? So I would go attack it.
Yeah.
There's actually two where the second one is I thought I knew what to do, but my frigging team can't execute. I don't know why. These are the two. Yeah. And then they lead to imposter syndrome.
Right. And this is a big challenge for, this is a bigger challenge, not for younger first time founders, but for founders who worked and were successful at larger companies where when things were bad, they could blame the man.
But.
But.
When things go bad and you're the founder and all you do was success.
The irony is people that worked at larger companies, successful, it's not true. They don't work. They try to outwork the problem because they're not used to like failure. And startups like decreasing amounts of failure. Pre-seed, it's failure every minute. [00:29:00] C, it's like failure half the time. You know, A is like failure, 40%.
Like, you know, , and so for me it's really when you see a founder being empathetic and just trying to get the answer that they already have by asking the right questions. And so like, I think that's, when I talk to people about VCs that they really like or really trust, it's someone who's sort of able to do that.
Do you think you've changed as an investor?
Excellent. How
so?
I would say in the early days, I would see a market opportunity and a product that if I were CEO of the company, would be a huge
company.
So I way over-indexed on that. and look for some of the companies that worked terrific, but for others that's just, that's not the business that we're in.
So I would say that has changed dramatically. And then the second thing I would say is in working with, even through the workshops, Well, I might have the right operational answer because I've run every other than HR and legal for obvious reasons.
Um, I've run most [00:30:00] functions at
I know what You mean by that
most software I've run most functions
software company. Mm-hmm.
And have the answer. I know what they should do,
do.
but I try not to tell them,
Good for you for just having the confidence of knowing it though.
but I'll tell them like in a second or third call.
And the thing I do now is even if I've told them and it takes, this is frustrating. Yes, Minnie, you meet with a founder, you're going through it and I wanna do this. And you're like, listen, I tell you this, not because I'm Moses and went to the mountain and I had divine inspiration.
I've tried that 10 times and it always failed. And then they don't listen to you. They burn like three to six months of time and a lot of energy and drama. And our whole goal, the look, the biggest advantage of being a former operator is
just to save them from making that
mistake. Yes.
But when they do it, you just have to say, you can't say, I fucking told you.
So you have to say, okay.
Yeah.
and they come back and they'll be like, okay.
I knew where you were going, Brett. I just wanna say I told you so, [00:31:00] so many times I don't
say it
that way. No. I have a company that for a year did not listen. I told them, this is dead wrong, it will never
work. And it was a disaster.
Mm-hmm.
And now it's working.
But now they're like, well, will you meet with the directs once every two weeks? I'll do that for the first two months. But after that, no. You, you have to take the ball from here.
Yeah. Brett, I could keep telling you for a
long time,
but I have to like get a little bit of personal questions
so then you have a hard stop. Like where did you come from? Brett? Uh, like what
city? were you
in
I, where did I, where did I
From
so
the reason why I'm relatively direct Yes,
Yes,
you
is I was a State Department kid, so my dad worked for the agency for National Development.
So like if you go overseas and there's a mission, there's like the ambassadors, the political appointee, there's the cool dad with like the bullet wound, he's cia, although I'll say something else. And there was my dad who worked for the State Department. And so I spent most of my childhood spending like four years in Maryland and then moving to a brand new continent for four years.
[00:32:00] Like I lived in Brazil Thailand, in Jamaica. So I would move continents. So the idea of seeing people ever again, I was like, I'm never gonna see these people again. And so I was like, all right, well, this is who I am.

I often ask people like, how do friends describe themselves? I'll ask you, but I also am just curious how you describe yourself.
authentic
for for better or worse. You know, I recently did a strength finders exercise. Oh. I've never done strength finders. I always like, you're e n tj Dri. Oh, driver. Driver. I'm asshole. Asshole. And I dunno if you've done strength finders. What was very interesting was it's very clever because what it does is it says, these are your five strengths.
But within each strength is the flip side of a weakness that you have to be conscious for. you know, I'm very direct, I'm very loyal. I give people the benefit of the doubt. My wife says I give people way too much the benefit of the doubt. ,
but often I've been called, I'm the, but I'm also the world's.
I may come across as the world's worst active listener. I'm listening. Yeah. But I'm processing.
Yeah. And, you know but I think they would call me loyal and authentic.
Well loyal [00:33:00] and authentic is great brett it's been so much fun getting to know you thanks so much for coming on the pod.