Navin: Tom, tell me more about Kana. What’s the market insight and what problem are you trying to solve?
Tom: So Vivek and I have been building generally in the market- martech, adtech domain for decades. In the last build-out of a company called Crux, around 2008, 2009, when cloud, big data, and new kinds of data processing techniques were taking root, and that really gave us the soil conditions to create a breakthrough kind of offering, for the modern marketer centered really on segmentation and audience management.
Well, now, today, we look at this, and we say, “Good Lord, those were promising soil conditions, but this is tectonic.” The AI revolution is not a state of mind, it’s fully upon us, and for the modern marketer, it changes everything. It’s hard to be a modern marketer because the CEO’s banging on you, saying, “Less spend. Oh, but I want 10X more.”
So those business conditions are also very promising for us because we’re meeting the moment, in giving marketers an end-to-end agentic marketing platform that helps them achieve those business results in this urgent way.
Navin: AI, we all believe, is, once in a lifetime opportunity. So how big is this for the marketing space, right? What’s your perspective?
Vivek: I’ll give you an analogy. AI and agentic AI, there’s a lot of excitement in the software engineering space, right? And engineers using Claude Code, Codex, Copilot, all these tools. There are a lot of them now, and the results are amazing.
You can actually build software much faster, and it’s only getting better and better with every new model release. The same kind of opportunity exists for marketing also. What is the Claude Code equivalent of marketing?
Navin: Yeah, it’s massive. It’s life-changing. And it’s going to elevate marketers to do things they weren’t able to do before, especially with outcome-based models.
Tom: What’s the Claude Code equivalent for the modern marketing? It’s Kana.
Navin: Amazing. I agree. That’s what made me excited to invest. So let’s switch back and go back in history. You guys have been doing companies for 20 years together?
Tom: It’s actually 26. But we like to say 20 because it just sounds better.
Navin: I thought it was 20. 26 is a long time, right? It’s a symphony. When I talk to you guys, you can complete each other’s sentences.
Tom: It’s a good story.
Navin: Yeah, tell us.
Vivek: Yeah, I was, actually at my first startup after I’d graduated from, grad school, and I’d spent about a year, 18 months, two years there, and, I was employee number 13 at that startup.
And things had happened, and there was just complexity, and so a few of us were “We need to get [00:03:00] out.” And, so when I started thinking about what I wanted next- I want to be engineer employee number one at my next, startup. So I started looking for startups, and I was “But how do you find startups?”
This was in 1999. So I, w- started visiting the portfolio pages of the top VC firms in the Valley. And one afternoon I was on Excel’s website, and I saw this little company called Rap that had just been funded. And my, my background, my, my interests were math and CS to solve business problems. So I just wrote an email saying, “Hey, so and so, I w- I don’t know whether you’re looking for engineers or not, but, if you are, I’d like to apply.”
And Tom wrote back.
Tom: We were sitting in a awful, dank little room on Carolina Street in [00:04:00] Potrero Hill next to a tennis court. This was not, this was not glitzy. And, pizza boxes stack- stacked high. We had just gotten the funding. There were two co-founders there, kind of there, but not all the way dialed in necessarily.
And so I get this… I’m thrilled when I get this email from somebody with… And that was a very algorithmically intense company, so I was– I had done, a lot of work in CS, but then gone and done a b- bunch of applied math. So there’s a very algorithmic mathy kind of undertaking at the time. So you find a C- math and CS engineer who wants to take the leap, and so we met, next to the tennis court, and, and we’ve been at it ever since.
Navin: So what made you become an entrepreneur, Tom?
Tom: It’s a great question. My best friend from fifth grade has told me that in seventh grade I said, “One day I’m gonna have my own company.” Hmm. I don’t remember saying that, but he swears by it. So apparently it’s [00:05:00] been sort of in the crockpot on slow for a while. I think I always…
You know, I, I like- The best thing about being an entrepreneur is the sense of agency and control and, and, and the belief that you can make it so. I was employee 35,642 at Sun Microsystems before starting off. So you remember that? I was, I… That was my number. I remember that employee number. By the way, I had a great ride at Sun, learned a ton during the run-up of, you know, in the first- Yep
the, the dawning of the internet. Incredible company. I was given incredible opportunities. So grateful for all of that. For me, being employee 35,642 versus hanging a shingle out and just having the joy and, and, and the feeling of, of building from scratch, there’s no substitute.
Navin: Vivek, why do companies again and again, you guys are serial entrepreneurs from starting companies to starting Superset.
Like, what drives you?
Vivek: As you might imagine, we’ve been asked this question plenty of times.
Vivek: You think we have our answers rehearsed, [00:06:00] but, but we don’t, ’cause it, it’s also evolving. Why we’re doing this is also evolving for us, but at, but at its, but at its core, it’s Solving interesting problems with people you enjoy working with-
Navin: Hmm
Vivek: and, having fun along the way. And also, coming back to Tom’s point about agency, we like building. We wanna build more and more with people we and we so wanna solve harder and harder problems.
Tom: What he said. Yeah, I, I think there’s probably some kind of chromosomal imbalance that makes us wanna to keep doing it over and over and over again.
Somebody told me once, wow, ’cause starting from scratch, you guys… A lot of entrepreneurs, when they’ve built, they n- they look back at the early stage and they say, “Well, I’m glad I went through that, but I don’t ever wanna do that crazy stuff again.” We seem to enjoy it.
Navin: So what’s different this time?
What have you learned from the past that you’re going to do differently because the world is about blitzscaling this time?
Tom: So much of the basics are intact still, right? [00:07:00] And so I notice these days everybody’s all aflutter about AI, and it is exciting, but unit economics and go-to-market and capital efficiency and all of the core things still matter quite a lot.
I like to tell people, “Yes, this AI stuff is exciting, but settle down. It’s still software. It’s still entrepreneurship, and the basics really matter.” Everything is just, it’s, it’s daunting, it’s scary, it’s exhilarating, but the need for speed to do everything that we used to d- do in 10 months, 10 days. Wow.
Everything you used to do in, a week, how about, we were just saying, how about now? We were talking about somebody on our team “No, don’t wait till Wednesday. Do it t- today. Like, right now, urgently” Because whether… And we’re rule takers. Whether we like it or not, that’s just the velocity with which businesses are unfolding now.
Navin: What was, Vivek, the key insight? You guys know marketeers. You guys know the problems they face.
Vivek: [00:08:00] There were a lot of things that used to be done a particular way, and based on our experience at, at Crux, that could be done differently in a more optimized manner, more efficiently, at a much faster pace w- using AI.
So that was the key insight really, if you wanna call it that, is that by building the basics again using AI, you unlock the ability to do w- significantly more things as a marketer using a- Got it … Broadcode-like platform.
Tom: You know, when I get going on a new project, I need to feel some mixture of, wouldn’t it be cool if, with a little bit of moral outrage, which sounds it’s, it’s crazy that this doesn’t, that this happens or this, that this hasn’t been solved already.
And so for me, and for I think every modern marketer, you should be a little bit outraged that The majors, and I’m thinking about Meta- Mm-hmm … I’m thinking about [00:09:00] Google with programs like Advantage+ and Performance Max, they’ve run away with it on- Yep … in the AI game. The majors have proven the power of personalization and targeting at scale through, through data and AI.
You can’t be showing up at a gunfight with a very sharp pencil anymore. Mm-hmm. True. It’s a marketer’s term.
Navin: Given your guys’ background with data, how important is, first-party data in this revolution, right?
Tom: At Crux, there was a, a customer, a very important customer of ours, who came to us and said, “Listen, we have 250,000 records in our loyalty database.
What can we do with that?” And at that time, we had to give them the bad news, “Mm, you can’t do as much as you want to.” Hmm. Time to go off and start accumulating third-party data sets to enrich what you have. Okay, well, let’s go back to that Meta example. Once upon a time, and I’m fascinated so many of us forget it, once upon a time, App- Meta’s one [00:10:00] regulator, a company called Apple-
Tom: came and asked all of us, “Do you want the app to track?” 75% of us said, no. Suddenly, Meta has 25% of the data that they used to have to power personalization and sc- and targeting. What happened? Well, they put the machines to work, they started using AI to create synthetic data sets, and the rest is history, right?
So what’s exciting for us is to see, no, to your question, first-party data. We used to talk a lot about big data. Let’s celebrate the power of small data, high-octane small data that marketers have now in, you know, on a first-party basis, energizing that with AI To create larger synthetic data sets that give them all of the efficacy and effectiveness that, that the majors use.
Vivek: Yep. And that is a perfect example of something that wasn’t possible earlier but is possible now because of all of the [00:11:00] advancements that have been made in AI.
Navin: Correct. There is this fear AI will just take over all the jobs, but in marketing, I anyways outsource. I need new tools. Do they get elevated or are machines going to do everything for them?
Vivek: Our view is that machines are not gonna take over. And the marketer will get elevated. The way we’re building Kana is, is, is in a way that the marketer does get elevated, but their role changes. Their role changes to one of orchestrator, of conductor, right? And so it’s really not artificial intelligence, it’s augmented intelligence.
Navin: How did you validate the problem you’re trying to solve? Like, has anything changed in the journey over the last two decades that you said, “This is our insight. This is what is gonna happen”?
Vivek: When Tom ta- Tom talks about Crux being adorable agents in the Kana platform, we saw this [00:12:00] firsthand at the end of Crux.
People were struggling because of, because of the amount of cruft they had created that we had enabled them to create through our platforms. That’s right. And they were “Well, how do we fix that?”
Navin: Right.
Vivek: Hmm. Right? And so that gave us natural inroads into, well, what if we could fix that? And that, that led to these early conversations.
Tom: It’s funny because every company that we’ve built, there’s sort of a, a grappling hook from the company that comes bef- came before to the one that follows. And we saw that mess of, of a th- you know, thousands of segments that we had allowed the mar- the marketers to create in, in our system, and we realized that it was gumming things up.
Tom: Right? And that’s the case for agentification. Like, no, no, no. Like oversee and control, but put these agents to work to dazzle you by surfacing the, the highest octane, most valuable agents. And again, to what Vivek said, you orchestrate and curate. That’s a powerful sort of [00:13:00] organizing principle for everything we’re building here at, at Kana.
Navin: So one of the beliefs we have is people build companies, people build products, and it has nothing to do with AI, and it’s even more important in AI. Like, you have started multiple companies, Tom, scaled them as a CEO, had billion-dollar exits. How do you assemble the starting team- Hmm … beyond the two of you?
Tom: We are obsessive, crazy people, Naveen, when it comes to recruiting that early team, and we’ve seen, you know, this, what the statisticians call path dependence. You make one hire, and then that creates a little bit of a drift that leads to another suboptimal hire or a really great hire, right? So setting the table with the management team, no weak links, no negotiation, no, “Oh, that’s good enough isn’t good enough,” right?
You have to, I think, really seat the team with, with strong doers who are natural-born entrepreneurs [00:14:00] with a risk-seeking attitude, who love the ambiguity. Like, it’s not something to be tolerated. They love the fact that nobody knows the answer, and there’s this puzzle we all have to crack. Get that, those cultural dimensions right, and things really, really work.
Vivek: I look for something I call their ability to scale horizontally. So we all know about horizontal scaling in the software context.
Vivek: I use that concept for people also. And what I mean by horizontal scaling is can you do, can you wear, can you wear multiple hats? So if you’re an engineer, do you wanna get into the product side of things?
Do you wanna go talk to customers? And if you hire those people with a horizontal scaling mindset early, early on, it allows you to do significantly more with a smaller team.
Navin: So Tom, right, like remind me, at Crux, right, a billion-dollar-plus exit, how many rounds did you raise? And you’ll know why I’m coming to that too.
Tom: Two rounds. There was a seed round. Okay, so actually three. There was a seed, an A, and a B.
Navin: Total capital?
Tom: [00:15:00] Total capital was 48.
Navin: So extremely capital efficient.
Tom: Very capital efficient, especially relative to there were multiple contenders at that time- Yeah … who had raised hundreds of millions of dollars and were not capital efficient.
We were really proud of our scrapping. And I remember some people would say, “Oh, but you need to sc- where’s the scale? Where’s the ramp?” Like, we’re good. Like we’re, we’re entrepreneurs. We’re, we’re hiring people who wanna be scrappy, who wanna horizontally sca- scale and, and do more. It’s also a very important thing for Vivek and me at the end of that journey- Probably one of the best parts was when the Salesforce corp dev person who had sort of stewarded the deal told us, “Listen, I do a lot of acquisitions around here.
I see, cap tables where three or four people make a bunch of money and everybody doesn’t really make much. I haven’t seen a cap table like this with that level of wealth creation for so many people.” [00:16:00] The company’s worth a billion-plus. That moment, priceless, right? So for us, being capital efficient, the point is we should be as sensitive to dilution as anybody, right?
And our employees should be as well. We try to coach our employees along these lines. You think you’re winning by getting those top-line deals, raising hundreds of millions of dollars. Maybe sometimes you need it. More often than not, I think it’s just peacocking.
Navin: Yeah.
Tom: So you can go to parties and say, “I raised $200 million.” But, mm, is that really working? Uh, or helpful.
Navin: Yeah, no, sometimes it can be empty calories, right? Yeah. Because startups, they don’t die of starvation, they die of indigestion, or they just waste. Yeah. There’s so much wastage, and which we see in big companies. So coming back to that theme, again this time around, you built this extremely capital efficient again.
You just did a small pre-seed round.
Tom: Mm-hmm.
Navin: So what were you hoping to accomplish with that before we are leading this round?
Tom: We want [00:17:00] to have experiments and validation and market conversations where we’re unabashed. We’re gonna create lots of little examples of what we think it needs to be. We’re gonna have hundreds of conversations with customers to see, “Hey, are we high?
Does this make sense? Does this resonate? Tell us what you’re doing.” Mm. And, and that doesn’t require a lot of capital. It just requires acumen and attention, we think, to the right problems. And then in that stage, we give ourselves a little license to form the team. We kiss a lot of frogs. We talk to a lot of people until we have confidence that we’re seeding the right team.
Again, that doesn’t require massive amounts of capital. I’ll tell you, we mentioned that first company Wrappt, and this was a lesson we carried forward at Crux. At Wrappt, I had an investor who teased me in a good way, and with reason. Because as a puppy entrepreneur, I was zigging and zagging, and there’s this and there’s that.
Oh, but that’s a cool idea. We should try the other. The lesson carried forward at Crux, and certainly now at Kana, and everything [00:18:00] that we do is stop, think. Like, really try to… No plan withstands- No indigestion … contact with the enemy. No indigestion. But really try to have a coherent specific plan for what we’re gonna build and do it.
Vivek: Over, over multiple stages, actually. Yeah, yeah. And that’s, that’s one thing that worked really well for us at Crux, and we’ve carried that forward at Kana as well.
Navin: So coming back to you, Vivek, do you have PMF now?
Because you guys had founder-market fit, but do you feel you have product-market fit?
Vivek: We definitely have PMF on the things that are already in market working with customers, right? There’s a symphony of agents that need to be built and, and orchestrated to work together. We still need to figure out PMF for, for those agents.
We have a very clear understanding of how they’re gonna work, and we can describe what they do, but the [00:19:00] customer conversations are still going to happen.
Tom: Scarcity breeds creativity. Scarcity breeds intensity. The point the, of this is to build a kickass AI software product that customers buy and, and that we c- and that, and that we get to learn and do it together and have fun.
Navin: What keeps you guys up at night? Because you know how to build companies.
Tom: First, I see some marketers who are unnecessarily seized up.
Navin: Hmm.
Tom: We need to do what we, whatever we can to help them to be thought partners. We’re not just peddlers of software, but to be thought partners who help them see the future and, and find a path, and get unstuck.
The second, I think, is just that the hype gets increasingly out of control, and nobody knows what they mean anymore when they’re on these panels. They’re just swinging a cat and making up stuff, and then smoking each other’s stash. Nobody knows what they actually mean.
Vivek: Hype does not [00:20:00] equal product, right?
No. And that’s my biggest… That’s the thing that keeps me up at night, is it’s so easy to create hype because you put in a prompt in ChatGPT, and oh, out comes three pages of hype for you if you want it, right? And, helping customers understand hype from reality is… Will get more and more challenging the more and more hype that gets created.
So that keeps me up at night, just building on what Tom said.
Navin: Having done so many companies, right, what are some of the lessons you have learnt?
Vivek: The number one lesson is people come first. Hiring the right people is just paramount. And so spend as much time as you need to hire the right people. Don’t settle for good enough.
That’s thing one. Second, make decisions fast. A bad decision made quickly is better than a good decision made slow.
Navin: Yep … because the market will pass you.
Vivek: Yeah, [00:21:00] exactly. So the speed of decision-making is paramount.
Navin: What would you tell yourself 26 years back that would apply to first-time founders today?
Tom: I would love to go back and tell myself 26 years ago that- First, breathe in, breathe out, it’s gonna work out. To try to find that straddle point between caring deeply and obsessively about what you’re building.
Don’t phone it in, right? Keep the intensity. But balance it with some quiet contemplation, right? To that earlier point, stop, think
Navin: I want to end by thanking you both for giving us an opportunity to be your partners along the way, and looking forward to climbing new heights together and helping you guys build an iconic company.
Vivek: Thank you for your support- Thank you … [00:22:00] and conviction that you’ve shown in us.
Tom: It means a lot.
Navin: Onwards and upwards.
Vivek: Exactly.
Tom: Let’s go get it
