Luke Diaz on Leveraging Data for Customer Retention and Business Growth
Welcome to show 357 of the Data Driven podcast! This week, we welcome Luke Diaz to the show.
Luke has an impressive track record of scaling startups to staggering annual recurring revenues, and today, he’s here to shed light on the pivotal role of customer success in growing a business. We’ll dive deep into the intricacies of customer success management, its impact on subscription models, and the measurements that underpin it. Luke also shares personal insights into his daily habit tracking and the data-driven approach to setting quarterly goals.
But that’s not all – Luke opens up about his journey from being a hedge fund manager to making a name in the software industry, cultivating unyielding ambition, and the significance of customer feedback in lieu of venture capital insights.
Show Moments
05:27 Marketing function has evolved, delivering value.
09:15 Companies need high retention to be successful.
13:34 Emphasizing the challenge of defining success in startups.
17:07 Analyze customer success, product strength, usage frequency.
20:01 Companies hesitant to invest in customer success.
24:38 VC interviews, cautionary tales, and relationship importance.
26:12 Caution to look at numbers in term sheets.
32:32 Entrepreneur achieves $100 million sale in 7 years.
34:13 Machine learning hype outweighs business value currently.
36:40 CSMs can upload public filings to chat GPT 4 for efficient reading.
39:47 Screenshots are simple, stable, and pervasively used.
43:34 Star Trek technology influencing modern innovations.
48:10 Recent recommended books on leadership and strategy.
50:22 Thank you to guest Luke Diaz, feedback appreciated.
Transcript
Hello. And welcome to another episode of the data driven podcast,
Speaker:where we peel back the layers of the tech world, 1 byte at a
Speaker:time. Today, we're diving into the heart of
Speaker:innovation, customer success, and the art of doing big things in
Speaker:the tech realm. Our guest is none other than Luke
Speaker:Dias, the visionary founder of d b t ventures and a maestro of
Speaker:turning startups into success stories. Luc has a
Speaker:Midas touch, transforming companies from their humble beginnings to
Speaker:powerhouses with over $100,000,000 in annual recurring
Speaker:revenue. LUKE is a veritable oracle of the tech
Speaker:age. So, if you're as excited as a
Speaker:processor executing a new algorithm to learn how to scale your
Speaker:business, predict the future with data, or simply want to hear from one
Speaker:of the leading minds in the industry, you're in the right place.
Speaker:Let's boot up this conversation and see where the data takes us.
Speaker:Without further ado, let's welcome Luke Diaz to the
Speaker:show. Hello, and welcome back to Data Driven. The
Speaker:podcast we explore the emergent fields of data science, artificial
Speaker:intelligence, and data engineering.
Speaker:And as luck would have it, our my world's
Speaker:favorite my most favoritest data data engineer in the world has
Speaker:rejoined this call. Today has been kind of an odd day. It's
Speaker:February 13th where we're recording this. And while it's not a
Speaker:Friday, it has that Friday 13th
Speaker:kind of vibe. Right, Andy? Yes, sir. So, yes,
Speaker:sir. Sorry about that. No. No worries. No worries. We had some kind of
Speaker:brown out, but I am So and I'm excited
Speaker:Yes. Because of our guest. Me too. So we
Speaker:had a, all sorts of things happen
Speaker:today, but I wanna get the show done before something else happens today.
Speaker:With us today, we have Luke Diaz, founder of DBT,
Speaker:Do Big Things Ventures, which has an amazing portfolio of angel
Speaker:and venture, capital investments, and
Speaker:advisory of tech, software, and other innovation,
Speaker:focused companies. He himself is an expert in customer
Speaker:success, tech support, software and SaaS trends.
Speaker:And, he has helped 3 startups grow from single digit millions
Speaker:to 100, 1,000,000 plus ARR.
Speaker:And, he releases regular research
Speaker:through thousands of subscribers, exploring focused
Speaker:topics such as customer success, how to improve your business
Speaker:writing, and building a churn prediction model with machine learning,
Speaker:as well as how VCs or venture capitalists
Speaker:establish track records of success. So thank you for joining us,
Speaker:Luke. I know that you had some kind of, sore throat, then you got better,
Speaker:and then Yeah. I I'm feeling
Speaker:a lot better. Frank, Andy, big fan of the show, honored to be here. I
Speaker:really appreciate you having me on the show. Thank you. We're we're very glad to
Speaker:have you, and we're able to get through this. So,
Speaker:the first question is, what is a Venture Capitalist?
Speaker:Right? So, you know, there's a lot of people. We work in technology. That term
Speaker:is thrown around a lot. I have a college buddy of mine who calls himself
Speaker:a Venture Capitalist,
Speaker:but he does real estate. So clearly, it's more than just tech, although,
Speaker:tech is clearly kind of, when people say the word, that that's
Speaker:the context. But tell me, what exactly is a venture capitalist?
Speaker:Yeah. That's it's a great question. I'd say the definition has shifted over the years.
Speaker:I I I just, I think we owe a debt of gratitude to
Speaker:Sebastian Malaby, who wrote recently published, The
Speaker:Power Law, which I think is basically the canonical,
Speaker:book that has the best all encompassing research
Speaker:on the space. So, if any of your listeners
Speaker:want to go deeper, it's definitely been the most
Speaker:recommended book to me this year, The Power Law by Sebastian
Speaker:Mallody. But I think at the simplest level, it's a person
Speaker:who's, giving money to start ups. You know? You you invest in
Speaker:small companies and you hope they get big. And this trend started in the
Speaker:sixties, and it really took a lot of different shapes and formats over the years,
Speaker:with governments playing a different role and partnership structures
Speaker:changing the face, activist versus passive. So there's been a lot
Speaker:of dynamics, but the same the trend the the baseline has remained the
Speaker:same. Giving giving money investing money into small
Speaker:companies hoping they get big. So that's that's what I do,
Speaker:that's that's one of the spaces I I love to learn and and play in.
Speaker:Very cool. Clearly, it's not just software, like,
Speaker:it could be anything, but so so thank you for that definition, because when he
Speaker:when he suddenly declared himself one day a venture capitalist, I was
Speaker:like, dude, dude, you're in real estate. And he's
Speaker:like, you know, it's more than just .com. This is during a .com
Speaker:kind of thing. Like, it's more than .com. So so,
Speaker:yeah. What exactly to you what is customer success? Right? Because,
Speaker:you know, I worked at Microsoft. I work now at Red Hat, and and
Speaker:there's this whole thing about customer success. And I've
Speaker:noticed that is also a term that I wouldn't say it gets
Speaker:overused, but I think different companies have different terms. Like, what when
Speaker:you what does customer success mean to you? Like, what how would you define
Speaker:it? That's a great question. I've I've been
Speaker:reflecting on that a lot because the space has changed so
Speaker:much over the last 10, 15 years. If I had
Speaker:to pick 1 word to kind of encapsulate the entire
Speaker:function and why companies are willing to spend 10,
Speaker:20% of their revenue on the function is is value.
Speaker:They are the owners of value
Speaker:being achieved and communicated to the customer.
Speaker:The value is like the and and there's art and science to that.
Speaker:Right? So they are the they are the team that is responsible for get
Speaker:often getting teams, new customers implemented, making sure they
Speaker:use it, overcome overcoming structural political
Speaker:things to, like, get this software
Speaker:integrated into a company that's never used usually, in most
Speaker:cases, never used your software before. So, I think of value
Speaker:as the north star, the guiding light of the function.
Speaker:But that said, it's taken a lot of different shapes and sizes,
Speaker:and and roles and responsibilities have shifted. But the
Speaker:the thing a lot of your listeners probably remember is, like, when software as
Speaker:a subscription became a thing, we needed a function or
Speaker:a team. The problem was, like, you don't just buy the software once on prem
Speaker:and forget about it and hope, you know, hope it renews. Like, these these teams
Speaker:have to use the software to get value, and they have to
Speaker:rebuy in the subscription model, which precipitated a need for
Speaker:this ongoing account management, but also
Speaker:usage and adoption component. So I think that was, like,
Speaker:the the change in the landscape that really precipitated
Speaker:the need for customer success. And, we could talk
Speaker:more about how to you know, what that means on a more detailed level, but
Speaker:that's how I think about it. Yeah. My my first exposure to the
Speaker:term was when they
Speaker:had this role. This is maybe, like, 8 years ago at Microsoft. They had cloud
Speaker:solution architects, but then then one day, they said, no. No. No.
Speaker:You're customer success architects now. And
Speaker:a lot of us looked at each other, like, so we're gonna do anything different?
Speaker:And they were, like, no. No. No. The jobs are the same.
Speaker:Okay. Why the change? And they're, like, well, because we're a cloud company
Speaker:now. Okay.
Speaker:Like, couches my exposure to the term. Like, I get it. Right? I
Speaker:understand the reasoning for it, but it was just kinda how I was introduced to
Speaker:it, inter introduced to it would would fit in very well
Speaker:with the theme of the day of just extreme weirdness.
Speaker:But, yeah. So so,
Speaker:like, what what are your thoughts? Like, how do you measure customer success? Right? You
Speaker:know, the the way we were measured, was kind of, you know,
Speaker:did they adopt the platform? Are they spending? Are there other
Speaker:metrics, like, customer satisfaction? Like, what? It seems like it's more than
Speaker:a one dimensional type of thing. And that
Speaker:you you raise a great point, Frank, because it is multifaceted.
Speaker:I think the role of a leader is is really clarity.
Speaker:And so where customer success leaders, I think, really need to step up is
Speaker:make sure that that scoreboard is super clear. Because if you're telling the
Speaker:team 10 things are important, guess what? None of them are
Speaker:that important, because we have this finite resource of
Speaker:time. And so the way I think about it is I love
Speaker:setting goals, performance, and comp based on lagging
Speaker:indicators and then managing to the leading indicators
Speaker:that are most correlated to that outcome. So, like, for teams I've
Speaker:managed in the past, the vast majority of their bonus
Speaker:was driven by gross, gross retention.
Speaker:Keep the dollars that we know. We've seen some pretty high customer
Speaker:acquisition costs over the last 10 years. You are companies
Speaker:are spending a ton of money, 50, 100, 250 k to
Speaker:acquire a customer. You have to keep that customer for
Speaker:years to make the unit economics make sense. And so
Speaker:if you have a leaky bucket, man, and you've seen a lot of companies
Speaker:over the last few years get turned upside down because unit
Speaker:economics weren't scalable, weren't sustainable.
Speaker:So gross retention, dollars up for renewal is
Speaker:the denominator and, like, how much of those dollars renewed? That is, in
Speaker:my view, the clearest way to measure the
Speaker:outcome of a high performance customer success team.
Speaker:There's a lot of ways and strategies you could take to get
Speaker:to that outcome. That's where I think management and leading indicators come
Speaker:in. You talk about, are the customers happy? Are they using the
Speaker:product? But customers vote with their dollars.
Speaker:And so I want to make it super clear to any team I lead or
Speaker:founders that I back, that retention is the name of the game.
Speaker:Because if you don't get that right, you you you just have this
Speaker:treadmill. You have this high cap, shitty,
Speaker:poor unit economics, sorry, you could bleep that out,
Speaker:yeah, you don't have a good business, so I try and anchor
Speaker:on gross revenue retention, as
Speaker:the the scoreboard. So a lot of our
Speaker:I say not a lot. All of our interviews are super
Speaker:cool, but not all of them are applicable to me in my
Speaker:small boutique business. So when you see me take out Andy's
Speaker:memory and a writing device,
Speaker:that that's applicable. So this is helping this one. That's your EMM,
Speaker:external memory module. That's me. So I am taking notes,
Speaker:Luke. Those are 2 good things. 1st, the book, the recommendation of the book,
Speaker:but I love the math. And, if you give me a numerator and
Speaker:denominator and it resonates, I'm writing that down.
Speaker:Yeah. World class retention is
Speaker:typically, 95%.
Speaker:Nice. So if you got a $1,000,000 business over the course
Speaker:of that year, you're looking at
Speaker:churn, the inverse of 50 k. That's a
Speaker:lot of revenue to retain. Right? So you're gonna renew
Speaker:950 $1,000 of that 1,000,000, you're
Speaker:invest in class. And there's there's a 2nd tier that's kinda like 90 to
Speaker:95, but if you get that right, man and then you you
Speaker:start layering on products, the whole revenue curve just
Speaker:goes stratospheric. It gets really really exciting when you have a
Speaker:strong foundation and a and a non leaky bucket.
Speaker:I like that. I like the leaky bucket analogy. Yeah. Yeah.
Speaker:Jinx. I'll take a monster energy drink,
Speaker:but, no. I'll change with my LaCroix. There you go. There
Speaker:you go. They closed school here, so, like,
Speaker:to deal with all the kids, I need the extra caffeine.
Speaker:Fair enough. But, so I mean, I would imagine so so this
Speaker:seems like, you know, this seem you've grown 3
Speaker:startups from single digit rev 1,000,000 revenues to a 100,000,000
Speaker:plus annual recurring,
Speaker:clearly, this has to be a factor in that. Right? Like, you you have to
Speaker:get this customer retention right, right, if you wanna scale. Is that
Speaker:a is that a fair assessment? It
Speaker:is. And it's a leading it's it's one of the criteria that
Speaker:most, series a, series b
Speaker:venture capitalists are looking for because they don't wanna
Speaker:they don't wanna invest in a lot of them got burned in these
Speaker:maybe they're high growth, but you got this leaky bucket where customers are just
Speaker:flooding out the back door. And that's not good because those
Speaker:customers talk to other people. It's like, oh, yeah. We churned that
Speaker:we we terminated that product. So it it really
Speaker:doesn't work unless you get those those numbers right,
Speaker:retention in the in the 90 90 to 95
Speaker:plus percentiles. Yeah. And it's become kind of
Speaker:a core metric for anyone that's looking at unit economics and
Speaker:the ability of this business to do something big.
Speaker:Yeah. So I would say, yeah, huge plus 1 on that as an anchoring
Speaker:metric. But then the more fun part of the job, in my like, it's really
Speaker:easy to run numbers at the end of the quarter or the end of the
Speaker:year. That's easy. But the the more interesting challenge is how do you
Speaker:get there? Right. How do you how are you structuring your onboarding
Speaker:process? How do you know if like, what is it how are you
Speaker:defining a successful onboarding? A lot of these startups
Speaker:I talked to, they they don't know. They're still figuring that out. How do
Speaker:you communicate value? You know, you start up, you build a a
Speaker:software or any business to solve a problem, give a strong
Speaker:hypothesis, but then you need to validate, like, okay, here's how we think about the
Speaker:return on investment. And by the way, most enterprises are looking
Speaker:for a, a software investment that has an ROI of 5 to
Speaker:7 x. So if you close this 100 k deal, they're looking for
Speaker:500 to 700 k of value to
Speaker:even rationalize renewing with you. So how do you that's a big
Speaker:number. Like, you're invested like, we better be able to show some business impact,
Speaker:and that that gets into the the products, capabilities,
Speaker:the impact on the business, the user workflows, and, ultimately, the p and
Speaker:l for how you're helping them either drive revenue or save
Speaker:costs. Right? It's this is all simple stuff. It's really easy to get abstract
Speaker:and hand wavy in software, but, like, it all goes back to the numbers.
Speaker:Right? So that I try and stay grounded in that way.
Speaker:Right. And as the cost of customer acquisition goes up, this becomes
Speaker:even more important. Right? We're not talking about, you know,
Speaker:somebody who's gonna drive by the the local convenience store and pick
Speaker:up, you know, a cup of coffee and a donut. Right? I mean, this is,
Speaker:you know, I'm sure they have numbers too, but the math is completely different in
Speaker:terms of what the incentives are. Right. Mhmm. Mhmm. Makes sense.
Speaker:Interesting. So what what what are the
Speaker:things that that because I'm sure in our audience, we have a lot of people
Speaker:who are either entrepreneurs, they run kind of boutique shops and shops themselves, and
Speaker:maybe they're thinking about, you know, I was gonna call you out by name, Andy.
Speaker:But but I I know I know for a fact we have a lot of
Speaker:people who are independent contractors here, and some of them I think are pondering the
Speaker:idea of, you know, hey, I'm selling my time for money. It'd be nice
Speaker:if I can make a platform where I can take some of that
Speaker:and kind of scale, like and I so I think this is an
Speaker:interesting opportunity to figure out, like, well, you know, how do you
Speaker:once you hit the single digit millions, obviously, you know,
Speaker:what's really the secret? Like, how do you that's a 100 x scale. That's 2
Speaker:orders of magnitude. Like, how do you if you had to pick the
Speaker:top 3 important things, what would they be?
Speaker:And I just wanna make sure I understand the question. You're talking along that path
Speaker:from it's called $1,000,000, which is a milestone in and of itself. Right.
Speaker:Like, getting to that 100 100, 1,000,000 revenue, what
Speaker:are, like, the from the customer success perspective? Right. The difference
Speaker:between generally. But the difference between comfortably buying a,
Speaker:Mercedes or 2 to buying a Bugatti.
Speaker:Right? Right? Like so it's like, what what
Speaker:how you get there. Right? I'm just I'm, like,
Speaker:curious. Like, what are the top 3 important things? Like, if you were
Speaker:advising somebody, like, what what really matters? Because there's a lot of
Speaker:noise in business, and I think the people that are successful
Speaker:can filter out the signal from the noise.
Speaker:What are your what are the kind of the 3 main levers to kind of
Speaker:filter out signal from noise?
Speaker:Let me let me ruminate on that, because as you
Speaker:mentioned, I've seen that ride three times and have been fortunate
Speaker:enough to play a small part in that in that outcome, in that growth.
Speaker:I'm trying to now, kind of, parse for common denominators
Speaker:that enabled that, I
Speaker:think customer success as one of the fastest growing
Speaker:functions in Silicon Valley in in the space.
Speaker:I think we do take a little too much credit sometimes
Speaker:because, at the end of the day, the product is
Speaker:that is what's being bought, and the and the product
Speaker:has to be there. So I would I would start with the
Speaker:inherent capabilities of the product itself, put
Speaker:away all the the post sales customer, kinda like my world that I
Speaker:operate in. If the product is not solving
Speaker:a valuable problem,
Speaker:and people aren't willing to pay for it, and it's not a
Speaker:lot better 7 x, you know, there's different data on how much
Speaker:better it needs to be than the next alternative, kind of like Ubers
Speaker:versus taxis, then you're not really
Speaker:in the arena to even get to 100,000,000. It you
Speaker:might just be building another high CAC inefficient
Speaker:leaky bucket, you know. Like, you might be able to ram
Speaker:software into these companies, but the the product's
Speaker:value and the strength is is what creates that enduring
Speaker:competitive advantage. So I I would look for
Speaker:the the nature of the product, the user mechanics,
Speaker:how frequently it's used, is it is it a
Speaker:product that you can habituate the users, as they
Speaker:adopt this new thing? Is it something you use once a month or is it
Speaker:something you need to use every day? So, like, the
Speaker:usage frequency and the perceived value
Speaker:are key indicators of, like, that product
Speaker:strength. The
Speaker:second is a willingness to invest in customer success. A lot of
Speaker:founders think the product can and should
Speaker:kind of just you know, if you build it, they will come.
Speaker:But the but the reality is is you start growing and you start getting some
Speaker:traction, 1,000,000, 2,000,000, 5,000,000. Now you're starting
Speaker:to think about moving upmarket where it's not selling
Speaker:a small smaller ticket item to an SMB or a company that's pretty
Speaker:nimble and can adopt your software, but you're talking to a collection of
Speaker:humans that now need to now need to adopt something new.
Speaker:So now you're talking about change management, process mapping.
Speaker:Hey. How does this software fit into your existing workflows? And the
Speaker:complexity gets higher. A lot of CEOs look at
Speaker:their head you know, right now is a common annual planning time. A lot of
Speaker:companies have their fiscal year end in January, and they're like,
Speaker:man, customer success could cost 20% of our revenue.
Speaker:And they're like, I don't want to make that investment. I've seen it
Speaker:a 100 times because it's a it's a big investment to have these
Speaker:humans try and figure out the complexity of working
Speaker:with these new larger customers and getting them to
Speaker:adopt a new habit, a new software, a new workflow.
Speaker:And so, that would be, like, linchpin number 2 is founder willingness
Speaker:to invest in the function,
Speaker:like, best in class success, at
Speaker:Salesforce, for example, is, like, 9 to 10% of revenue, so they're running
Speaker:a really efficient machine. They also have a lot of revenue, so the
Speaker:denominator is pretty big. But their their customer
Speaker:for life program is typically 9 to 12% of revenue, and that's considered
Speaker:hyperefficient. But when you're small and you're just trying to go
Speaker:out there, bag some big deals, and help them out, it's not uncommon to
Speaker:see customer success cost 20% of revenue. So
Speaker:on a 5,000,000 ARR business, are you willing to invest $1,000,000
Speaker:to hire, you know, 8 people and some
Speaker:managers to, like, take on this challenge? Maybe not.
Speaker:And then you're, kind of, setting the stage for those customers to not get the
Speaker:help they receive. So that's, like, kinda linchpin number 2 after
Speaker:product strength is is the willingness
Speaker:to even invest. And then, you asked for a third one, I
Speaker:might need there's so much variability that comes into
Speaker:play with market dynamics, the macro, the competitive space. So
Speaker:I'm not sure I have a clear third one that is
Speaker:abstractable. But those 2, I think, are important right there,
Speaker:because I think so the second one, I think, kinda well, the first one, if
Speaker:you don't want the first one, the second one's irrelevant. Right? Like but, like,
Speaker:the whole willingness to expand up to 20%, I mean, I that's
Speaker:a tough pill to swallow for a field that most people, if you ask them
Speaker:what customer success is, they'll probably give you a blank look,
Speaker:or as they say in LLM world, hallucinate an answer.
Speaker:Right? Like, because, like, even even I'm,
Speaker:like, I I only know I only got deep into this because as we were
Speaker:doing our planning for my day job, we were, like,
Speaker:you know, customer success, and the guy basic the guy runs it kind of
Speaker:explained his pitch. And I was, like, oh, well, that makes perfect sense. You know?
Speaker:But prior to that conversation, I don't know. I would have been, like,
Speaker:you want 20% you want, you know, like, if you were a $5,000,000 company,
Speaker:I mean, that's, you know, may maybe not in the Bay area, but that's
Speaker:still a lot of money. $1,000,000,000 will buy will
Speaker:buy you a house around here. But,
Speaker:sorry. I thought that was a not okay. I thought that was a really good
Speaker:analogy, and bringing the numbers home,
Speaker:being a person, you know, I'm, you know, being a person in business for
Speaker:myself, I'll just say it that way. The, and from
Speaker:that perspective, I'd I'd like to ask,
Speaker:how do you deal with folks who may be reluctant
Speaker:to engage with any form of venture capitalist
Speaker:person simply out of fear of the unknown?
Speaker:They don't understand it. They, you know, they've
Speaker:maybe they've heard some horror stories of, you know, things
Speaker:deals going south and bad outcomes. Or they've seen
Speaker:Shark Tank, right? And they're like, you know. Well, I mean, you know, and I
Speaker:mean, the risk aversion, I think everybody has
Speaker:some bit of that. And certainly, you know,
Speaker:the 100 X upside. Yeah. I'm all in,
Speaker:you know, on that piece of it. But I'm wondering what's I don't understand
Speaker:permit. I'm I'm just gonna confess. I don't understand all of the mechanics of
Speaker:VC deals. I imagine there are many variations,
Speaker:and there has to be a certain amount of trust with the actual
Speaker:firm or the venture venture capitalist. So how would you address you
Speaker:can you can talk to me. How would you address my fears of the unknown?
Speaker:It I think it's a very valid point.
Speaker:When numbers are involved and, like, you're a founder, you're talking about the equity of
Speaker:your company. You know, someone's coming into
Speaker:this room and and you're gonna you're gonna lock arms and be
Speaker:financially entangled. It's it's not dissimilar to a marriage in
Speaker:some regards because, like, you're going to be working together. You're not sleeping together,
Speaker:but you're you're working really closely together on the financials and you have
Speaker:a a very vested shared interest. But you kind of hit the nail
Speaker:on the head. It is a relationship business. You guys have interviewed
Speaker:some some great VCs and some in the space. So,
Speaker:I would encourage your listeners to relisten to some of those episodes, as well, which
Speaker:I found really valuable. The things that,
Speaker:I think scare people are the like, you mentioned the horror
Speaker:stories. So everything's great when the market's up, but
Speaker:where it's kinda like when when someone passes away or
Speaker:there's a divorce, that's where stuff hits the fan.
Speaker:Right? So you start to hear stories of dirty term
Speaker:sheets, which basically have these
Speaker:prep stacks or these, like, liquidity preferences, which basically just means, like,
Speaker:I get my money out before other people, and I actually might get more money
Speaker:out than other people. They they kind of
Speaker:they derisk the deal
Speaker:by exerting leverage to minimize
Speaker:their downside and and that screws other people. Right? Like, that's
Speaker:less money for employees, the founders, and
Speaker:subsequent investors. So dirty term sheets are are
Speaker:something that are a tactic I've never employed. I'm
Speaker:usually a little earlier, so there's some standardized agreements that, thankfully,
Speaker:thanks to Paul Graham and the team at Y Combinator, they've put
Speaker:out these simple agreements for future equities,
Speaker:like a basic safe agreement, which I've used dozens of times,
Speaker:where it's clean, it's founder friendly. There's a ton of
Speaker:these being populated. Yeah. So I would caution you to
Speaker:look at, like, the this I would encourage you to look at, like, the
Speaker:numbers in the sense of, like, dirty term sheets and press stacks,
Speaker:they're exceedingly rare. Like, I've only seen
Speaker:them in less than 2 or 3%
Speaker:of the companies or deals that I've worked, where there is really a
Speaker:VC trying to to leverage, you know, and have kind of
Speaker:an angle. My question is that VC would be,
Speaker:like, why do you want if you believe in us so much, why do you
Speaker:why are you trying to, like, change the nature of the dynamics?
Speaker:Because because the best VCs just want you to be successful. They're not planning for
Speaker:the divorce. They're not making you sign a prenup. So,
Speaker:anyway, that's just, just one thing on the the term sheets
Speaker:where I think it's it can be perceived as a little bit predatory.
Speaker:And, yeah, I I don't think most founders need
Speaker:venture capitalists. I think I encourage like, if you
Speaker:don't need my money, please don't take it. More money for founders is
Speaker:better for you. Do don't delete it. It's it's almost, like, glamorized a little
Speaker:bit. Like, these are just people writing checks that and and they
Speaker:have an amazing network. So, like, there's really smart people, but, like, they're just
Speaker:writing checks and joining board meetings. So I would almost knock
Speaker:them down a peg because the founders are the ones creating value and
Speaker:changing the world. It's it's not the venture capitalist, so I would almost
Speaker:I would challenge the premise of that. I don't think most
Speaker:founders even need it. I'd much rather see them bootstrap.
Speaker:Well, that's that's an interesting take, you know, as a as a founder.
Speaker:That's that's an interesting, thought. And I've I've not
Speaker:seen, you know, and I guess that's not what VCs lead with, you know, when
Speaker:they're when they approach or angel investors. That's not what they they first lead
Speaker:with. So it's refreshing, actually to hear
Speaker:that. But the other side of it, I wouldn't discount, even though I
Speaker:know less about the process than I
Speaker:would need to know before, you know, I participate. But even
Speaker:then, I know the value of a network and I know the value of
Speaker:advice and having a broad experience
Speaker:across many different businesses in the field. And being able
Speaker:especially to look at something dumb that I'm
Speaker:doing and go, you know, Andy, that's dumb. And, you know, let me tell you
Speaker:this other horror story about this founder who did exactly what you're doing, and then
Speaker:they lost everything. And, you know, that's that advice
Speaker:I think would be valuable as well. I mean, I won't say invaluable, but
Speaker:it's not nothing. And to have that described as you did
Speaker:early in terms of a relationship and being arm in arm and and
Speaker:working for the success of the venture because that
Speaker:makes perfect sense because then everybody wins.
Speaker:Mhmm. Well said. And the, I think back to
Speaker:my days at Optimizely where, Benchmark led our
Speaker:a round, and Peter Fenton, who's a fairly well known
Speaker:investor, is on the board at Twitter and Yelp. He joined our board, and he
Speaker:was very helpful and insightful. And you know what? He he didn't
Speaker:offer advice, but he asked really good questions. And I had him come speak to
Speaker:my team at an off-site, and, we're expecting this long,
Speaker:eloquent talk. He just went up to the the whiteboard, you know, and he
Speaker:wrote executive visibility equals
Speaker:budget. And we talked about this concept that if, like, the
Speaker:executives and your customers, if they don't know who you are, you don't have budget.
Speaker:And so he has these to your point, Andy, he has these
Speaker:insights that can lead to really interesting things, and he asks really good
Speaker:questions. And so the value was less than the money and more about, like, the
Speaker:insights and the questions. What are the unknown unknowns you're not thinking
Speaker:about? That's where I think VCs can Yeah. Maybe maybe
Speaker:impact the trajectory more. Yeah. Well said, I'd love to call out.
Speaker:Yeah. I I love that because I I say this because it's true.
Speaker:I I don't know what I don't know. And if I'm a solopreneur,
Speaker:like I am, it's like I am stuck here unless I have
Speaker:good friends. And I do. I have Frank and I have a number of really
Speaker:close friends who are in positions all over in different companies.
Speaker:1, one good friend who was an early guest on the
Speaker:show, about almost 2 years ago, got
Speaker:his MBA from, from the Sloan School at MIT.
Speaker:And he's gone on to gain experience, and he's reached out, you know, a
Speaker:number of times. In fact, I mentioned, I think in the green room with Frank
Speaker:and I met at this, user group meeting in Richmond in late November
Speaker:2005. I met we met Nick there as well, the 3 of
Speaker:us. And so, you know, and so Nick's awesome.
Speaker:And but he has these conversations with me as as
Speaker:well. And knowing each other that amount of time,
Speaker:first off, and then, you know, interacting, we partnered
Speaker:a little bit and and done a little bit of work. Kinda know each other's
Speaker:personalities. That's been it it's not a
Speaker:board. But it's what I would imagine
Speaker:a good board would be like. They're advisors. There's
Speaker:there's more than just a fiduciary interest,
Speaker:and this is actually love. You know, we're friends.
Speaker:So, anyway Love it. For a mutual concern.
Speaker:Yes. Yeah. Nice. Mutual concern. Did have
Speaker:you have you heard of a founder named Jeremy Clark? Does that name ring a
Speaker:bell? I haven't. I've seen the name on LinkedIn,
Speaker:but I don't I'm thinking about the casino. You have a lot.
Speaker:I'm sorry. Funny because he's a he really likes driving fast cars.
Speaker:I don't know. Anyway, Jeremy Clark, I I bring it up because
Speaker:a lot of your listeners are hustling to build something special and
Speaker:use data driven insights. This guy started, a company
Speaker:called Webmerge in:Speaker:I don't think he took any outside capital, maybe some friends and family.
Speaker:He built it up to 5,000,000 ARR, very
Speaker:achievable number, and he didn't have a lot of
Speaker:outside advice from boards, but what he was relentless about was
Speaker:listening to the customer feedback. Hey. I wanna do this. So his whole
Speaker:feedback, he didn't have a team of advisers or high paid PCs. He just
Speaker:listened to the customer. Interesting. Fast forward so when once he got to
Speaker:$5,000,000 right thereabouts, he sold to
Speaker:Formstack for $100,000,000.
Speaker:And he was able to achieve this in, I think, 7 years.
Speaker:So he's kind of that canonical bootstrapped hustling.
Speaker:If there was a third thing to ask to add to your first your
Speaker:earlier question, Frank, it'd be that, like, that customer centricity of,
Speaker:like, they guide you. Like, you don't need a VC to tell you what to
Speaker:do. The customer will tell you what you you know, solve this problem, solve this
Speaker:problem. They got loads of problems. So I'll mention Jeremy Clark and the
Speaker:Formstack acquisition of WebMerge as one of my
Speaker:favorite and most powerful examples Yep. Of
Speaker:customer feedback and just the what an amazing founder can
Speaker:do. Well, I'll just interject that that's very confirming to me
Speaker:because that's that's how I roll right now on customer stuff. It's
Speaker:just they they say what they want. I look at it. I
Speaker:go, yeah. Yeah. And often when they do that, Luke,
Speaker:I'll say I'll think of, oh my gosh. Yes. We can do that, and then
Speaker:we can do this. Mhmm. So it is very much a
Speaker:virtuous cycle. So Yeah. Yeah. Cool.
Speaker:Very cool. So while we're on the subject of
Speaker:kind of being data driven,
Speaker:and, so talk to me about it, Frank. How does has
Speaker:machine learning kind of, like, helped in the customer success space in terms
Speaker:of figuring out churn, retention? Like, has that
Speaker:has that helped? Is that or is it just kind of a, like,
Speaker:a, more hype than than help?
Speaker:I'd say it's more hype at this stage. For
Speaker:my function, I I've definitely seen some interesting use cases,
Speaker:but I'd say the hype far outseeds the business value at the
Speaker:moment. There's 2 use cases that have really helped
Speaker:me drive performance. 1 is figuring out
Speaker:churn. So machine learning is really good at
Speaker:taking lots of attributes,
Speaker:analyzing them for what's most correlated with churn, but you need a big
Speaker:enough sample size, so you might be at, you know, how many how many
Speaker:things can you train the model on is is really valuable in
Speaker:the instance of machine learning to reduce churn. That's a use
Speaker:case I do like. We've used, I've used XGBoost,
Speaker:which is a Kaggle grade model, and, also Random
Speaker:Forest, which is another way it's just another fancy name
Speaker:for a type of model that's trying to figure out something.
Speaker:But, yeah, that helped us reduce churn by highlighting accounts that were at
Speaker:risk that we had not known were at risk.
Speaker:So talk about unknown unknowns, machine learning is really good
Speaker:at raising flags for things that a human might look
Speaker:over. No. I think this account's fine. Actually, the machine learning
Speaker:model says you're they're actually very risky. Let's talk about
Speaker:that. That's where I've seen value case number 1. Value case number
Speaker:2 is applying large language models embedded in
Speaker:call recording software, like Gong, Chorus. The notes that you can
Speaker:get like, you record a call with a customer. The
Speaker:built in large language models now that summarize the
Speaker:notes are phenomenal. So you just saved your CSM
Speaker:an hour post call because the notes are almost turnkey. They
Speaker:pull out action items, they pull out key topics, they pull
Speaker:out filler words like, yeah, So, there's even
Speaker:coaching embedded in the the software. So Gong and
Speaker:Chorus are the the best tools I've used that machine
Speaker:learning, like, or in this case, large language models have really had an
Speaker:impact on type time saving and quality.
Speaker:No. I'll second that. I use I use Castmagic to do a
Speaker:lot of the show notes and stuff like that, and it Oh, yeah. The
Speaker:feed they've added, recording as an option and, for for do meetings,
Speaker:and it it is science fiction level good at
Speaker:that. Yeah. And if you have a customer that's
Speaker:publicly traded and you have, like, a 10 q or one of these public filings
Speaker:that big companies have to to file, you can upload that to
Speaker:chat GPT 4. And, actually, they're getting it's
Speaker:a good a good CSM should know their account. One way to
Speaker:do that, hey. Upload the s one or sorry, the 10 q,
Speaker:and I've been impressed with the output of chat
Speaker:GPT 4 and reading an s one, so you can save, you
Speaker:know, 98% of the reading time.
Speaker:So that's another time savings, but I don't know, maybe there is value in having
Speaker:them read the q the 10 q to to get deeper versus just
Speaker:getting the topical superficial summary of it. But that's
Speaker:been that's been interesting. Something I'm watching along with, like, the data
Speaker:analytics tools built into these models. Very
Speaker:cool. Yeah. Awesome.
Speaker:So, Andy pasted the, the the the
Speaker:preformed questions that we have.
Speaker:And, so the first question is, how did you
Speaker:find your way into into the space?
Speaker:Did you find the space, or did the the the space find you?
Speaker:In a past life, I was a hedge fund manager, so I've always been I've
Speaker:always loved numbers. So I'd say I
Speaker:found a love of numbers When I was, at
Speaker:Cal Poly in San Luis Obispo and I was studying numbers, I was like, I
Speaker:really like spreadsheets. So I'd say I'd say I found
Speaker:numbers, and then in when I transitioned into software, I saw, like,
Speaker:woah. This is much bigger than spreadsheets. This
Speaker:is, like, big data at scale. So then I got interested.
Speaker:Cool. That's my quick story. So we have second question is,
Speaker:what's your favorite part of your current gig?
Speaker:I love being on a Zoom call with a founder I'm meeting for the 1st
Speaker:time and seeing their absolutely unbridled
Speaker:ambition for they're gonna charge at the world and
Speaker:they're gonna make a dent in it, and I just
Speaker:it's something about the human spirit that is, I don't
Speaker:know, it just gives me the goosebumps to this day, and I get
Speaker:really excited when I have the honor of, like, meeting a founder that is
Speaker:hell bent on making the world a little bit better in
Speaker:their domain, so that gets me pretty that's definitely my favorite thing.
Speaker:Cool. So we have 3 complete this
Speaker:sentence, questions, and when I'm not working I
Speaker:enjoy blank.
Speaker:Man, I love flying airplanes, so I'm I love
Speaker:flying up in the sky, and also training for
Speaker:triathlons. I do a lot of, like, triathlon stuff, Ironman stuff,
Speaker:so I'm usually I love flying, and I love swim,
Speaker:bike, run, and, and obviously spending time with the kiddos
Speaker:and my wife. Very nice. The second1 is I think the coolest thing
Speaker:in technology today is blank.
Speaker:Man, old school answer, I still think screenshots are one of the most
Speaker:low like, screenshotting is one of the most
Speaker:simple technologies that is so pervasively used, and I think
Speaker:it's not talked about enough how amazing just a screenshot
Speaker:tool is used anyway anyway. But a more concrete answer
Speaker:is I think stable stable diffusion models are becoming next
Speaker:level. I I've seen I asked my my 3 year old
Speaker:daughter, hey, Davie, what are you thinking about? She's like,
Speaker:a rainbow unicorn. And I type in, show me if you know, create
Speaker:an image of a rainbow unicorn, and we have this, like, shared album on the
Speaker:iPhone and on the TV. So she she has all her, like, stable diffusion
Speaker:images on the TV rotating just a way to get your kids involved.
Speaker:But, I've been so impressed in, like, video is the next frontier. I mean,
Speaker:it's insane what visually these models can do
Speaker:now. That's really exciting. It is very
Speaker:impressive. My my middle child is
Speaker:into anime now. And, you know, so we
Speaker:will take, like, clips of him or him playing with the dogs, or just a
Speaker:description and say, as an anime. Right.
Speaker:He could kinda create his little little, like, anime thing.
Speaker:It's just I might have to try that with my daughter. That sounds Yeah. Yeah.
Speaker:I I I never got into anime, but, like, thanks
Speaker:to him, I can kind of I only like the 1 movie Akira from,
Speaker:like, the eighties nineties. But, like, thanks to him now, I I know about 1
Speaker:piece, demon slayer, Naruto, and there's something
Speaker:else he's watching because it's snow day. He's watching it upstairs. I can hear it
Speaker:in the background. So you got us talking about kids now. So,
Speaker:you know, stand back. My my baby girl is at,
Speaker:Virginia Tech now, doing her her 2nd semester
Speaker:there. And, I'll just I'll encourage you. Thank you. I'm
Speaker:so so, so proud of her. And my other my other daughters
Speaker:and my my 2 sons as well. They're all proud of them. They're they're
Speaker:awesome. The, the advice I always
Speaker:give dads, especially, of daughters, especially,
Speaker:is drink this in, man. Drink because like in 2 weeks, she's
Speaker:gonna be driving. It's gonna feel like that
Speaker:when you when you get there. It's just it will.
Speaker:And the other just tidbit I share
Speaker:with dads is you're it's normal for you to look back
Speaker:and say I didn't spend enough time. And it's a vicious trap, and
Speaker:it's not true. Yeah. If you spent all of your time, you would
Speaker:still look back and wish you would spend more time. Regret, wish
Speaker:you would have spent more time. Yeah. So, don't fall for that. I appreciate that.
Speaker:Absolutely. My oldest is going to high school in the fall, and
Speaker:he's ready. I'm not ready. I know. Right? I'm not ready. I
Speaker:said that to the end of the day. I'm not ready ready for him to
Speaker:go to high school either. As I said to him, because they had, like, an
Speaker:open house or whatever. I'm like, I I I can't believe it's high school already.
Speaker:I'm like, wow. And I looked at him, like, you're ready. I'm already,
Speaker:like, it's it's totally on me. A big step. Yeah.
Speaker:Keep us posted. That's a big deal.
Speaker:The next complete the sentence is, I look forward to the day when
Speaker:I can use technology to blank.
Speaker:The technology is not there yet, but when you can talk to someone in another
Speaker:language and it real time translates in the AirPods.
Speaker:Oh, nice. I feel like that's going to connect humanity at something we've
Speaker:never seen before. That's that's that's one
Speaker:that I'm personally just as someone who loves to travel and connect,
Speaker:man, would that be a game changer or what? Yeah. For sure.
Speaker:And it's almost there, Like, it's it's it's not you're right. It's not there yet,
Speaker:but, you know, it's the closest. Yeah. We're close. I mean, it's almost like,
Speaker:you know, I think we've hit another, you know, Star Trek is
Speaker:often used, cited as example of, like, leading indicators of
Speaker:technology, and it's just like, you know, the other day I was
Speaker:using we had a previous guest on the previous show that talked
Speaker:about how you can interact with ChatGpt through the Android or
Speaker:Ios app, And, like, just
Speaker:through voice, and, like, I this is very Star Trek. I could be, like, you
Speaker:know, give me an image of this or give me an answer to this. It's
Speaker:not clearly what I was looking for. Can you me? And it's just it. Yeah.
Speaker:If you watch kind of like the next generation, how they interact with the computer
Speaker:is very conversational. And I think we're seeing a lot of that evolve
Speaker:today in ways that not that long
Speaker:ago were impossible. And when you mentioned screenshots,
Speaker:the first thing I had to learn when I switched from Android to to Android
Speaker:from Ios was how to do a screenshot. Because I cannot function
Speaker:Yeah. Without the ability to do a screenshot. Right?
Speaker:Yeah. Cool. It's amazing. I'll just I'll just throw this
Speaker:out because I was, Frank and I were communicating
Speaker:when he had this leap to conversations
Speaker:with Chad g p for the app. And he
Speaker:was I I know when Frank's excited, and he was very excited about it. And
Speaker:he was like, this is so phenomenal. And I'd heard about the
Speaker:functionality, but I've just been like, I've been typing at it for,
Speaker:you know, a year, and it's been typing back to me. And I thought that
Speaker:was super cool. But hearing the enthusiasm in his voice, I was like,
Speaker:okay. I gotta get this. I I it it
Speaker:is it is game changing, and it was from a previous podcast guest who showed
Speaker:me. And I'm like, he did, like, a live demo. I'm like, no way.
Speaker:Like and it shouldn't have surprised me in the way that it did because, you
Speaker:know, voice recognition technology is, you know, not a 100%, but it's
Speaker:it's good. And then voice synthesis technology is,
Speaker:you know, better than the recognition. That's for sure. Like, it
Speaker:shouldn't surprise me combining these 3, but here I
Speaker:was just the lady with the result. So our
Speaker:last our next thing is we ask guests to share something different about
Speaker:themselves, but we always throw out, remember, it's a family
Speaker:podcast. We're trying to keep our family friendly rating and all of that.
Speaker:Let's see. You know, I heard a quote. I was reading,
Speaker:Marcus Aurelius and some of his writings,
Speaker:and there's a quote that really stuck with me. He said something like, be
Speaker:tolerant of others and strict with yourself. So one of the
Speaker:things I'm a little strict with myself on is I track everything
Speaker:I do on this, like, weird little table. Like, at the end of the day,
Speaker:I write down, did I work out? Did I stretch? Did I do this? Did
Speaker:I do that? Did and there's, like, 30 things, so I'm a little Wow. I
Speaker:kinda micromanage myself just to know, like, do am
Speaker:I capable of doing the things I say I'm gonna do?
Speaker:And so I I have a lot of data on my own personal, so that's
Speaker:a little weird. It's, like, a little neurotic, but also helpful. We're, like, oh, I
Speaker:committed to that, but I didn't do it. That's interesting. Why?
Speaker:Did I you know what I mean? So I've been trying to, like, use data
Speaker:driven insights to, like, reflect on why I do
Speaker:or don't do something I say I wanna do
Speaker:in my quarterly goal setting. So You know, that that sounds like
Speaker:spreadsheets. It it sounds like habit tracking, but
Speaker:then using the habit tracker, that data. And that's something
Speaker:that I haven't heard people speak of before. So I'm intrigued
Speaker:and inspired. I like the idea myself. Like I have
Speaker:the from for my blog and look at the the content I produce,
Speaker:I have a spreadsheet and that has kept me very honest.
Speaker:I need to do that for working out and stuff like that
Speaker:too. Like, I like that idea. I mean, it's really helpful with the with the
Speaker:physical stuff. It's really helpful. And, yeah, I'll send you
Speaker:I'll send you the a visual of you guys and we could compare notes
Speaker:because I feel like we're all trying to solve a lot of the same
Speaker:challenges in mine, that is very help that is really helpful in that
Speaker:regard. Sure. I'll share what I what I use, and, yeah, be neat neat to
Speaker:swallow this. I I actually have my blog, spreadsheet
Speaker:off there on that screen there, so reminding me that
Speaker:I'm behind schedule. So
Speaker:Audible is a sponsor of the show, and you can go to
Speaker:thedigitsroombook.com, and you can get a free audiobook on us. Do
Speaker:you do audiobooks on, either way, can you recommend a good
Speaker:book that you like? Yeah. Two recent
Speaker:ones. On the more, like, inspirational and
Speaker:entertaining, I would recommend The $1,000,000,000,000 Coach about Bill Campbell,
Speaker:written by 3 Google executives, Eric Schmidt among
Speaker:them and, Mr. Rosenberg and, the
Speaker:story of Bill Campbell is one of the most incredible stories of
Speaker:Silicon Valley, so I would point listeners to that for education and
Speaker:entertainment and just, like, learning about leadership.
Speaker:Practical, Hamilton Helmer's
Speaker:strategy book is off the charts. I forget it I
Speaker:read the hard copy. I forget if it's on audiobook, but
Speaker:it's called 7 Powers by Hamilton Helmer. I recommend it
Speaker:to every CEO I work with or fund or just
Speaker:meet, and a lot of them have started already have heard
Speaker:of it, But it's basically how to build a business. Yeah. It's really
Speaker:good. Excellent. So Yeah.
Speaker:So, where can people learn more about you and your business?
Speaker:You know, if they wanna I have some book summaries on my website. So if
Speaker:they go to dbtventures.com and they go to library, I think I
Speaker:got, like, a couple 100 books I've read and some nerdy notes I
Speaker:take because I I don't trust my memory. I read a book and I'm
Speaker:like, what was that book? So I did I try and distill it down in
Speaker:the 5 page, you know, short summaries for mostly for CEOs, honestly,
Speaker:and founders. Because they all tell me they wanna read more,
Speaker:but they have not much time. So I'm like, here's a summary.
Speaker:Maybe, you know, maybe it's valuable, maybe it's not. So, yeah,
Speaker:DBT Ventures is one way and then LinkedIn. Okay.
Speaker:Yeah. Whatever works. That that's what you spot. Okay. Well, I'll definitely be
Speaker:connecting with you on LinkedIn. We had a little exchange earlier, and I
Speaker:was I was so excited because, I love it. I love connecting
Speaker:with guests, and I was like, now I've got the link to you, and we
Speaker:can connect through that. Yeah. And me to you. I'm stoked.
Speaker:Thank you guys so much for having me. Hey. Thanks for coming. I'm glad we
Speaker:can make it work, with weather and health challenges and all
Speaker:that. Kids snow days, you know, we persevered, and thank you very
Speaker:much for your patience, and, we'll let Bailey finish the show.
Speaker:And just like that, we're at the end of another enlightening episode of the
Speaker:data driven podcast. A monumental thank you to
Speaker:our guest, Luke Diaz, for sharing his invaluable insights
Speaker:and experiences with us. Luke, your journey and
Speaker:the wisdom you've imparted today are nothing short of inspiring, and
Speaker:we're all the richer for it. To our listeners, we hope
Speaker:you've found this episode as fascinating and illuminating as we did.
Speaker:It's your curiosity and passion for knowledge that drive this show, and
Speaker:we're endlessly grateful for your company on this journey through the Datascape.
Speaker:Before we part ways, a small but significant request.
Speaker:If you enjoyed today's episode, please take a moment to rate and review
Speaker:us on your preferred podcast platform. Your feedback
Speaker:not only warms our digital heart but also helps others discover our
Speaker:podcast and join our growing community. Remember,
Speaker:whether you're scaling the next unicorn, decoding the mysteries of machine
Speaker:learning, or simply curious about the tech world, you're always
Speaker:welcome here, where data meets discernment.
Speaker:Until next time, keep crunching those numbers and questioning the
Speaker:status quo. I'm Bailey, signing off.
Speaker:Stay data driven, my friends.