Anand Thaker: From Cold Emails to Y Combinator and Being Acquired
By: Caleb Brown
July 1, 2025 27 min read
Anand Thaker built his first tech community with an idea he couldn’t let go of, so he started making 500 LinkedIn connection requests every day to tell people about it.
He didn’t have a fancy pitch deck, venture capital funding, or a well-known name. But he had a clear belief that tech leaders could learn more from each other than from static documents. That belief turned into Pulse, a peer-to-peer digital network for IT executives, which Anand co-founded and scaled before leading it through Y Combinator and eventually to acquisition.
Today, as managing vice president of engineering at Gartner’s Peer Programs, Anand brings that same builder’s mindset to one of the world’s most respected research firms. In this episode of Keep Moving Forward, he reflects on growing something from scratch, navigating the noise of venture capital, and staying curious at every stage of your career.
Creating Something People Actually Want
Anand didn’t grow up with computers. In fact, he didn’t touch a modern computer until he was 16. But after earning a computer engineering degree from the University of Illinois and working at startups like Glu Mobile and Cooliris, he saw an untapped opportunity in the marketplace.
IT executives across industries were flying blind, trying to keep up with change without a map. “Historically, what’s happened is they go to companies like Forrester and Gartner to get research reports,” he says. “But we felt like there is a way that they can all collaborate with each other and learn from each other instead of talking to an analyst.”
Anand’s team built Pulse with a simple mission: Keep execs informed about trends, solutions, and their peers. To get started, they didn’t chase scale. They chased relationships. “Each time we met someone, we asked them to connect us to three more people,” Anand says. That hands-on approach attracted a core group of early believers, some of whom became investors or advisors.
Pulse also made sure to build a community that these executives actually wanted to associate with. “We want to serve executives,” Anand says. “So one of the questions we'd always ask them is, what are you looking for out of a digital community? If you're going to go somewhere on a regular basis, see others like you there, what do you want to get out of it?”
Building a Startup the Hard Way (i.e., the Right Way)
Anand credits Y Combinator (YC) with sharpening his focus. One of YC’s advantages is that you can “surround yourself with other high-energy people who are building things,” he says. “It was rejuvenating” and helped Anand understand the real work of early-stage leadership.
“Focus on building something a few people love rather than building something a lot of people like,” he says. This principle helped shape Pulse’s evolution, including its approach to product-market fit.
YC reinforced another truth: Doing the work matters. Whether it was onboarding users or iterating on product feedback, Anand embraced the scrappy side of building. “Don’t be afraid of doing the manual things early on. We would figure out how to automate them later.”
That early grit paid off. After YC, the team received additional investment interest, which eventually led to an acquisition. Looking back, Anand says, “Only raise if you have to. It’s always better to raise less than you think.”
Finding People to Support Your Tech Dreams
Anand sees tech’s evolution as a series of unlocks. First, access to knowledge became widespread through online courses and lectures. Then, app stores made it easier for anyone to build software. Now, AI tools are expanding who gets to build and how fast they can go.
“We have democratized ability to build,” he said. “You need to know how to learn to build using that framework. As a developer, you work very differently, so it can be frustrating at times. But once you do, and if you build in small measured steps, you can make progress.”
This rapid evolution of technology is actually an opportunity for anyone who wants to enter the tech field and is willing to put in the work. “It’s easier to get in than you think,” he said. “There’s a lot more people willing to help you than you realize.”
His story is a reminder that access, effort, and networking are still powerful tools for anyone trying to build something meaningful.
Transcript
Anand Thaker:
If you're building something, start reaching out to people who may have built something remotely in that space because they have an interest in the space. They will know investors, and if they sense that you're genuine and you show promise, they will introduce you to some investors. But once you talk to the first investor, that investor will introduce you to a few others. And really, all you need is one investor to agree to being your lead investor, and the rest will follow. You just need one person to finally sign up.
Caleb Brown:
Hey, everyone, and welcome to Keep Moving Forward, the podcast from X-Team for tech professionals who are passionate about growth, leadership, and innovation. I'm your host, Caleb Brown, and in each episode, we'll dive into candid conversations with the tech industry's brightest minds, seasoned leaders, forward-thinking engineers, and visionary experts.
Today, I'm joined by Anand Thaker, managing vice president of engineering at Gartner's Peer Programs. Anand brings a unique blend of startup grit and enterprise scale with a career that spans founding a VC-backed startup, building digital communities for executives, and now driving innovation at Gartner.
In this episode, Anand shares the lessons he's learned from Y Combinator, how to fundraise the right way, and what it really takes to build momentum from scratch, especially when you're cold emailing strangers and doing everything manually. We also dig into his take on the three eras of tech transformation, his advice for navigating early stage leadership, and the underrated power of genuine outreach. If you're a founder, a builder, or just someone who's trying to understand how the tech industry evolves from the inside out, this conversation has a lot to offer. Let's get started.
Thank you so much for joining today. Really happy to have this conversation, I'm excited. I was looking over the notes the last time we spoke, and there's a lot of good stuff in here that I'm excited to dive into. But I thought maybe a good way to just start was to hear a little bit from you, just about your kind of journey from studying computer science engineering in India, all the way to becoming a leader in the Silicon Valley tech scene. I just wanted to hear the abridged version of your journey there.
Anand Thaker:
Absolutely. And first of all, thank you, Caleb, for having me. Appreciate the opportunity to chat. I thought this was very interesting. Love that you've launched this new podcast, and excited to be a part of the conversation.
So I was born and raised in India. I hadn't even interacted with a modern computer until I was 16. But we moved to the US when I was 16. Interestingly, not through the H-1B visa, which I don't know if you are on X, but there's been a lot of discussion around that.
Caleb Brown:
A lot of discussion, yeah.
Anand Thaker:
But we moved through a family reunification visa, and then got my education at University of Illinois at Urbana-Champaign. I got my computer engineering degree there. Computers were very hot at the time. This is, we're talking early 2000s, early aughts. And when I graduated, I knew that I wanted to move to Silicon Valley. There were a lot of very exciting things happening there.
But I also enjoyed being in the early stage of things, and I'd worked at two early-stage startups. One was Glu Mobile, one was Cooliris. Both were really fun. I wanted to found a company myself. And I teamed up with the founder of Cooliris, his name is Mayank Mehta. I teamed up with him, and we decided to see what we could do.
And one idea that we came up with was, we see a lot of executives, every company, as Marc Andreessen has said, software's eating the world, every company has someone doing IT. And often, it's very lonely at the top. Often, you don't really know what you should be doing. You come in, you're often in a new role beyond your experience so far, and you don't know if you're doing the right thing. Are you hooked up to the company's strategy? Are you working closely with the CEO to execute their strategy? Is there something else you could be doing? What are the trends saying?
And this happens in all sorts of industries. Oil and gas, manufacturing, forestry, government. We always think of the Silicon Valley giants, but every company out there has IT. And honestly, they don't quite know what they're doing. I've talked to a lot of chief information officers now, and they're humble about it. They know that we have some idea, but we don't know what the trends say.
And historically, what's happened is they go to companies like Forrester and Gartner to get research reports and learn from them. And those relationships are great, but we felt like there is a way that they can all collaborate with each other and learn from each other, instead of talking to an analyst. Maybe we can make the process a little bit faster. So we decided to see if we could disrupt that space.
And we already have a solution like this for software engineers, for example. Stack Overflow. Anyone who's a software engineer will have used Stack Overflow. I've used Stack Overflow. Maybe a little less relevant today in the age of AI, but still useful. But something like that, but for executives. And we can maybe start out with chief Information officers and VPs of IT, but then we can replicate that across marketing, across finance, and so on. Everyone needs to collaborate with each other. I'm sure CFOs have a lot of questions for each other and want to ask each other what's going on, which is exactly what happens at conferences. But conferences don't — they're not always on. They happen once in a while.
So how can we get them to do this in a digital space? So we started working on that. We decided to call it Pulse, as in keep a pulse on what's going on out there. What are the trends out there? What are some of the solutions out there? How can we take advantage of them? So we started out by building, at the time chatbots were popular, we started out at first with a chatbot to see if we can collect insights from people. Knocked around a few ideas, and then ultimately built a mobile app. But there's always that flywheel challenge. How do you get the first iteration going? Same with your POP passwords. Well, how do you get the first? We're not a known quantity. How do we get the first people to come in?
So we had that same startup challenge, and we started just reaching out to people on LinkedIn. We just connected with 500 people a day. Not everyone will connect back, but just keep trying to connect with as many people as you can and see who connects back. Send them a message, tell them what solution you're building for them, and see if that resonates. It did resonate with some people, and then they connected back.
Another thing we did at the same time, and this is useful for anyone looking to build a startup. If you're building a startup, if you have an idea, but you don't really have any connections, you don't really know how to get going, look for others who tried to build something similar. We found someone who had tried to build — not even exactly the same, but anything in the remote space. We found a startup that the chief business officer at SurveyMonkey at the time had been building, so we reached out to him.
And what you find is people are really nice. People are very, very friendly. They want to help you. They want you to succeed because they've done it, they want to pay it forward. So we reached out to him. He was happy to connect. He spent an hour with us in his backyard, invited us over to his house and told us what he had learned, how we could get started. But more importantly, he connected us with three others. So he went to those three, and because it was an intro, they were happy to chat with us.
Each time we met someone, we asked them to connect us to three more people, and this is how we grew the network of people who believed in us and wanted to invest in us. Not financially, always. Investments can be in terms of time, advice, feedback, connections, all of it. All of it helps. And we built an advisory council of people. If they could just give us their knowledge and experience, that was great. We would interact with them on Slack. Every time we had a new iteration, we would show it to them and say, "What do you think? Do you think this would work?"
Then we had others who were interested in investing, but small checks, because these are all individual players, small angel investors. But we just waited for a little bit. We took some small checks, but we waited. And I have some insights on fundraising that, if that's interesting, I can share some, as well. But there were people who were interested in investing, as well. And then there were people who were actually interested in guiding us as to how to develop this, and that was very interesting, as well. There were some people who are very connected, they would just introduce us to loads of people, some to VCs. And then we started talking to venture capitalists, as well, to see if we could get some investments, as well.
We got some investments early on. That was great. A small seed round at first, which was interesting. But we kept on building, we kept on growing our network. There was a lot of manual stuff, and it always felt weird to be doing this manual stuff. How would we ever automate this? What is the point? But we later applied to Y Combinator. Y Combinator is the first accelerator, started by Paul Graham. And he's an amazing character, by the way. He has a lot of these essays that I used to read way back in the day, very interesting, and loved the way he thinks.
Our mentor was Jared Friedman, who continues to be a mentor. He was the founder and CTO of Scribd.com. And a fascinating guy, really smart guy, has worked with a lot of startups, very humble. Works all the time. And has the hallmarks of some of those people who are very successful. You'll notice that people who are very successful and have a lot of responsibilities somehow oddly seem to respond to you very quickly, quicker than most other people who have few responsibilities. And he has that quality too, responds right away, any time of day. You email him at midnight, he'll respond in 10 minutes. So, amazing character. There's a lot of things he helped us with in growing the startup, but he told us to not be afraid of doing the manual things early on. We would figure out how to automate them later, but don't be afraid. And that's very true, as we found out.
When we left Y Combinator, that was very helpful in getting funding. A lot of companies were then interested in investing in us. Once you get that YC check mark, it's a badge of approval.
Caleb Brown:
Well, that is a phenomenal kind of journey through your career, and I'm glad that we were able to talk about all of that and to kind of go on that journey with you again. And one thing I want to mention that you touched on that I think is really important was just on that piece about reaching out to folks, even if you don't know who they are. If you're working on a product or something that's in, there's a CEO or someone that you, maybe your first gut reaction is like, "Ah, they're not going to respond to my email."
Man, that's one of the things I've learned in my life and career is how often they will respond to your email if you just reach out sincerely. Not saying like, "Oh, invest in me," or, "I need this." Just being genuine, asking questions, saying like, "I'm working on this." The response that I've had in my life of just kind of cold-emailing folks in that world is tremendously high. And I think more people need to know that even now, that's a good option that you have for reaching out to folks that you want in your wheelhouse.
Anand Thaker:
Yeah, let me mention something in that regard, actually, from having talked to a lot of executives. So executives, because this is what we do, we want to serve executives. So one of the questions we'd always ask them is, "What are you looking for out of a digital community? If you are going to go somewhere on a regular basis, see others like you there, what do you want to get out of it?"
And we noted that there were five things that they are looking to get out of such a community. The first one is to learn. If you go there, you want to learn something, which helps you grow in your career. Second is you want to be able to ask questions once in a while. The third is you want to get recognized. So you want to be on a stage with these folks and you want to get recognized for what you bring to the table, for the knowledge you contributed, and that's really important to them. The fourth is you want to network with folks. You want to form connections. You want to grow your network. You want to find interesting people and learn interesting things from them and form personal relationships.
But another thing that we found is very important is they want to contribute. They want to pay it forward. And we found this to be the case over and over, like you said, we learned this later from interviewing them and we confirmed it, but we found out ourselves when just reaching out, people just respond, and they respond very quickly.
I think you can tell when a request is genuine. You recognize someone who genuinely wants to create value, and they're not trying to sell something to you. They just really want to gain your expertise. And because you've been successful, you want to pay it forward, and you want to make sure others are, too. So a surprising number of people will not only reach out, they will help connect you with people. They will spare time to give you feedback. And they may even be part of your advisory council. And we continue to have relationships with some of these folks to date.
Caleb Brown:
Yeah, well said. Yeah, I just wanted to make sure we highlight that because it's something I really do believe in. It was just nice to hear that you kind of sprinkle that in.
But yeah, so like I said, we went on that full journey of your career, which is very fun. And you're interesting because you've worked at these big companies, and you've started your own startup and worked in smaller things. I'm kind of curious, especially across the domains, we've talked about gaming and mobile and then enterprise. I'm curious how those different domains, that diverse experience, shaped your overall leadership approach and just how you tackle things.
Anand Thaker:
Yeah. So first, I will say that when we were doing the startup, Pulse, we found ourselves in a unique place because we had worked on the consumer side of things, which was really interesting. But we also had enterprise experience, as well. So because we offered both, VCs were more interested in talking to us. Because what VCs are looking for when they're looking to invest in someone, of course, there is the idea and what you're looking to build and how successful they think it'll be. But even more important, I would say, is the team. And of course, take Mark Zuckerberg. If he's looking to raise funding, not that he needs funding, if he's looking to raise funding, people don't really care what he's going to build. They will just be interested in investing in him. So the team matters a lot.
The fact that we came with consumer and enterprise experience made us much more well-rounded because one has this very interesting sales cycle, the other has very interesting gaming mechanics you need to build to get people in and get the flywheel going. If you have experience with both, you're just that much more well-rounded.
So I find that working at Gartner and especially working in this place, we work both on the enterprise side, as well as on the consumer side, so it's a very interesting situation. On the enterprise side, Gartner has clients, a million of them, that we end up engaging. And our success is measured by how many of those clients we create value for. So that's the enterprise side of things. But even at the consumer level, we allow executives outside Gartner, who are not Gartner clients, to come in, as well. And that forms the consumer side of the experience, so we're simultaneously working on both sides. So it makes for a very fascinating, well-rounded job profile. So I've been really enjoying that.
And I recommend people to try both. Both offer their pros and cons. Consumer can be very challenging. I found lately, ignoring the AI boom for the moment, but if you go to the pre-AI boom, I found that consumer startups had started to dry up. The big companies that you saw forming about 10 to 15 years ago had started to dry up. It was harder to succeed in that space, but there is a new life in the beast now. And I do see that things are changing so rapidly now that it's very hard to predict where it will go.
I would say that I've worked through three eras. We saw that the first era was that we democratized access to knowledge, where people, anyone could go and watch MIT lectures, watch college lectures, watch YouTube videos, and learn things. We saw that, and that was a very interesting era. People who were locked out of these things could now learn things that they otherwise never had access to. You would have to go to some elite institution in order to get that, but now anyone can.
And then we noticed that there was access to building things. And I lived through that era, which I thought was very interesting. And what I mean by that is, when I worked at Glu Mobile, only some developers who were buddies of Verizon or T-Mobile or the big players, only they were allowed to build apps or games to place on those carriers and put them on their app stores. But if some random Jane Doe or Joe Schmoe wanted to build an app, tough luck. They're never even going to talk to you. IPhone changed that with the app store, right? Apple changed that game and democratized access to building things, and all sorts of people were suddenly building apps. You didn't have to be a recognized player. So that was another big change, which made it possible for all sorts of people to go and become developers and build things and do startups. It started a whole wave of startups.
But then the third wave that we find ourselves in now is that we have democratized ability to build. And what I mean by that is you needed to be a developer, you needed to know how to write code to build things. And while these technologies are admittedly very nascent, they're not mature yet, and we have yet to see where they go, we have multiple apps out there now, Cursor being the most famous example that people are using. By just describing things in English, it can go and build that for you. You need to know how to learn to build using that framework. As a developer, you work very differently, so it can be frustrating at times. But once you do, and if you build in small, measured steps, you can make progress.
And this is the beginning stages of this, but we're going to see people build things by just describing things well. And I think this is a very new era. We're going to see things get built very rapidly, where little things that you would get frustrated about like syntax, not getting this right, not getting that right, where's the bug in here? They become so easy. If anyone codes, if you just go and paste the snippet of your code that you have a problem with, you don't exactly know what's wrong. You just paste it, you don't even have to describe anything. You don't even have to write one word. You just go and paste that into one of the current foundational AI models, and it'll just tell you, "Oh yeah, everything looks good. Seems like you're trying to do blah, blah, blah. But here, I see a problem." And spot on. You didn't even need to say anything. So we're just at the beginning stages of what I think will be a new era in building things, and I'm very excited about that.
Caleb Brown:
Likewise. Yeah, yeah. So I did want to talk a little bit more about your Y Combinator experience. I know you said we could drill a little bit more into that. But yeah, probably a lot of folks listening to this are familiar, but Y Combinator, you're right, the first accelerator, the largest accelerator, backed companies like Reddit, Airbnb, pretty legit. So I just wanted to see if you could tell me a little bit about just some kind of key lessons and takeaways and things like that from your time and your experience at Y Combinator, and just kind of how that influenced your entrepreneurial journey. I know a lot of people have talked about their experience and things, but everyone has their own experience, and I would just really love to hear a little bit more if you could just tell us a little bit more about that.
And what I'll say also is that — it's a little near and dear, unfortunately did not get in, but they did fly me out in 2009, and I got to meet with Paul Graham and Jessica. And I was doing a small startup, Web 2.0 era, that was an educational bookmarking site, where it was visual. So it took a screenshot of the website, and showed that to you visually and worked really well for educator or early kindergarten, first grade, second grade, early education. So I did get to go to the Y Combinator campus, but yeah, we'd just love to hear more about your experience there.
Anand Thaker:
Yeah, I met Paul Graham over there, too, fantastic character, as well as Jessica. Really great people, very very kind and helpful. Lots of things I learned at YC. If I had to boil it down to three key things that I think really made an influence on me is things you know intuitively, but you really realize it when you're there.
The first is the energy when you surround yourself with people who are building things. So if you're a builder, if you're starting a company, don't just toil away in the basement. I think that's great, there's nothing wrong with that. And if that's what motivates you, then fantastic. And I've been in that mode, too, I know that mode. You emerge after three days, take a shower. I know that, and it's very fulfilling to just get immersed in something. But it was also great to get away from things sometimes, go to the YC office and see all those founders there. And it was rejuvenating.
You can toil away for weeks and weeks by yourself, maybe in cafes or somewhere else. But when you go to a place like this, and you see all those other founders building things, you get so many new ideas when you just talk to them and tell them about what you're building. And that energy really pushes you. So it provides a break from the tedium of just being by yourself. And I would highly recommend people do that. Go to the local accelerator, go wherever you can find other people like yourself building things. So I would highly recommend that. Basically, the takeaway is surround yourself with other high-energy people who are building things.
The other thing that YC is famous for telling people about is, focus on building something a few people love rather than building something a lot of people like. Right? And we saw that at first, right away, where we just focused on getting a lot of people in, let's get a lot of users. But things really changed for us when we got a few people who really loved the product and then started to grow from there. Because you build it according to what they tell you, and then you go in the right direction. And when you stay a bit focused and hone that experience and then expand further, it works out a lot better than trying to do a little bit of everything for everyone. That doesn't work very well, and YC always drills that point home.
And then the third thing that has been great, especially during, but also after YC, is the network that you build while you're there. You become a permanent part of the family, so to speak. There is a website they have called Bookface. You're always a part of that family. You can reach out to people, you can post there. There are people posting about new startups they're founding and looking for anyone to join. You can hire people from there, you can find a co-founder there, and so on. So I think that's been fascinating. So what that has taught me, and we all know this and we all hear this, but network matters. And I found that to be one of the most valuable aspects of joining YC.
Look, they do take, I don't know if the terms have changed more recently, I think they might have, but they do take 7%, at least at the time, they took 7% of your equity, which is not a small amount. And for very little funding, relatively speaking. So I would say in general about fundraising, only raise if you have to. We did find YC to be very valuable in this regard. But some of these things you can get elsewhere. You can surround yourself with builders without actually going through YC. You can get some of the lessons of YC just by looking at some of their podcasts. There's a podcast that Jared Friedman is a part of, you could follow that. There are a lot of lessons that they publish. You could just read those. So you don't really need to go through YC, but that network has definitely been very valuable.
And if you have an opportunity and you have the tolerance for giving up some equity, I would definitely say, yeah, go for it. But for fundraising, I will say one thing. I wish we hadn't raised as much funding as we did. It's always better to raise less than you think, I feel. And it's a scary thought because you're left without funding, you can't hire people. But if you just suffer through those early stages, I think it's a lot more rewarding.
Caleb Brown:
Yeah. I've heard that more than I've heard the opposite. Yeah, so that totally makes sense. One thing, just to kind of tack this onto the end here, one thing that I always personally took — a Paul Graham thing, I believe it's Paul Graham — was do things that don't scale. Yeah, and that's always — so after I left, I worked as a software developer for a few years, and I actually left to start a loose-leaf tea company. So it was a subscription company, I did a different loose-leaf tea blend every month. I did tasting notes, I did a tasting video. And something I started doing actually was writing a handwritten thank-you letter to every new person that subscribed. And I don't remember the numbers now, but I remember the cohort of subscribers stayed longer, truly, from doing that. And I knew that if we grew to be a very large tea company, I couldn't hand write every single new subscriber, but that worked well initially.
I've always liked that because there's such a focus on scaling and optimizing. But one of the benefits of being a startup and being early is that you can run it exactly how you want to and you can be more personalized. And you're more agile, you're more nimble than a bigger company, so I always liked that one.
But I did kind of want to, we're running out of time, but I did want to talk a little bit, you mentioned it earlier about fundraising. I wanted to see if you did have some advice that you would give to founders who are navigating potentially being acquired and having different companies court them. And just I wanted to hear any of your advice on finding the right fit because it sounds like you were talking to some great companies and seemed to find the right partner. Just wanted to see if there's anything you could say on that for anyone that might be in a similar position.
Anand Thaker:
Absolutely. So first, in terms of finding an investor, they are getting bombarded with so many emails that they don't really know who they should talk to first. That prioritization becomes challenging. They simply don't have enough time to go through every application that comes their way.
So what really helps is an intro. And I know that's a chicken-and-egg trouble. Well, how do you get the intro? One way is you can just go through LinkedIn, but like I said, start reaching out to people. If you're building something, start reaching out to people who may have built something remotely in that space because they have an interest in the space. They will know investors. And if they sense that you're genuine and you show promise, they will introduce you to some investors. But once you talk to the first investor, that investor will introduce you to a few others. And really, all you need is one investor to agree to being your lead investor, and the rest will follow.
You just need one person to finally sign up. So that's one route, I would say, is definitely start reaching out to people. Start cold-emailing people. Be genuine. Don't ask for things right off the bat, but tell them what you're trying to build, and meet them and show them what you're trying to build. Be respectful of them and their time, and they will introduce you to people. So that's one thing.
Second thing is when you go to an investor, I would say it always helps to be ready. So instead of going and saying, "Well, I have this idea, and here's my deck," which is great, but not very helpful. They really want to see, if you're not a known quantity or you've built something in the past that you can showcase, it helps to have some sort of a demo for them that showcases what you're trying to build. It showcases your ability, because anyone can build a deck. So I think that's really helpful.
And knowing that they have very little time, putting the key points in there is very helpful. Keep it short, don't err on the side of filling it with as much detail as possible. There's enough workshops and tutorials online on how to make a pitch deck for VCs. Definitely follow those. Those really help. YC was very helpful in that, drilling the point home that less is more when it comes to these pitch decks.
And then when you meet VCs, what I found valuable was to first do some homework on them, look into what they've done. What are the investments they've made recently? Because they're already interested in that topic, and bring that up when you meet them, show them that you actually are aware of what's going on in the space, what they're up to. It shows them that you actually — they're not a commodity to you, that you could go with any VC, they're just one amongst many, but you are actually genuinely interested in this particular firm to go with. So that helps a lot.
On the other side of things, if you have a lot of VCs who are interested in you, I would say first go with fewer investors rather than more. We made the mistake of having too many investors, and that was challenging when doing an acquisition. If one investor balks at the idea of you selling your company, you have challenges to deal with. So go with very few people, go with trusted investors.
Another thing I would say is, yeah, if you have a lot of companies interested in you, and you need to pick between them, what helps is to talk to startups that investor has invested in. Go and email them, do a cold email, go do a cold outreach. If they've been burnt by the investor, they will be more than happy to tell you about that story.
Caleb Brown:
Yes. Yes.
Anand Thaker:
And you want to know that story.
Caleb Brown:
Yeah, absolutely.
Anand Thaker:
So reach out to a few, and make sure that they all have good things to say. And if they're unhappy, they will tell you what's on their mind, and you will know who not to go with. So that's very valuable, I would say. YC has an internal board where people post reviews on VCs, so that's very helpful. But if you don't have that resource, just reach out to people. So I would say that one is very useful advice, as well, that people should bear in mind.
And try to go with a VC who seems like they'll be able to help you beyond just giving you money, because they have a lot of connections. And if they can spare some time with you, if they can meet with you not regularly, you don't want it to be burdensome, where they're driving the company and you're just following the route they chart for you, you don't want that, either. But you also don't want someone who just throws some money your way and is so aloof that they don't really care what's going on.
Caleb Brown:
Absolutely. I think that's some very good advice. And my last question, because we're running out of time here, but it's a question I like to finish every episode on and get the perspective of the guest. Just curious if you could kind of wave a magic wand, if you will, and sort of change one thing about the tech industry or maybe the tech industry culture, I'm curious what that is, what change you would make?
Anand Thaker:
I would say one thing, which is, maybe this is not exactly about the tech industry, but about people who are aspiring to get into the tech industry. If there's one thing I would change, I would just tell people that it's easier to get in than you think. There's a lot more people willing to help you than you realize. And it's not that challenging. There are easy ways to get started, you just have to have the confidence, self-confidence, belief in yourself, and invest the time and know that it will pay off.
Software has eaten the world and will continue to, and we're going into uncharted territory with AI and robotics coming our way. It's going to transform entire industries. We used to not be able to predict what's going to happen in 30 years. Now it's hard to predict what's going to happen in five. Very interesting times.
So I would recommend all listeners to, just in general, have some confidence. There are lots of tutorials out there, but make a plan, make a study plan, and just go through it. It'll take a few months, but it will really reward you. And there are lots of people willing to help. If you want help, there are lots of resources available, lots of mentorship available, but go for it, and this is your time. At any age, you can do it. That's what I would say to folks looking to start out.
Caleb Brown:
100%t agree. Couldn't agree more. And yeah, I think a great point to end on. Thank you so much, I really do appreciate your time today. Loved that conversation, that was really interesting.
Anand Thaker:
Thank you, Caleb. Loved the conversation. Thanks for your time.
Caleb Brown:
That was an inspiring deep dive with Anand into what it takes to go from concept to community and ultimately to scale. What stood out most was Anand's clarity around doing the hard, unscalable work early on, whether it's cold-emailing hundreds of people on LinkedIn or handwriting messages to your first users. His experience building a network of believers, navigating venture capital, and leading a startup through Y Combinator offers a rare, honest look at what founders really face.
I also appreciated his insight into the evolving eras of tech. He left us with powerful reflections on how the tech landscape has changed. We've moved from democratizing access to knowledge to now making it easier for anyone to build using AI. He also reminded us why community and contribution are becoming essential parts of the executive culture.
Thank you, Anand, for sharing such practical wisdom and grounded encouragement for anyone navigating this ever-changing landscape. And thank you to our listeners for joining us. Join next time for more insightful conversations with tech leaders who continue to inspire us to grow, lead, and innovate. Find us on Apple Podcasts, Spotify, or YouTube Music. And don't forget to share this episode if it resonated with you. Until next time.
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