Anisha Bhandari - Co-Founder Chekout.ai

Welcome to another Founder Wisdom podcast. We have Anisha Bandari with us today. She's a co-founder at Checkout.ai, democratizing agentic, uh, commerce. The next Google, ex-Georgia Tech Computer Science and Stanford GSB. It's been on my Spark Tank show, Real Lighter Pitch, so I thought I'd have her on the show here to talk about Checkout. So Anisha, welcome to the podcast. Tell us a bit more about yourself and what you've been up to.

Thank you, Charles, for that warm introduction. My name is Anisha Bhandari. I'm the founder and CEO of Checkout.ai. And what we are is an agentic enablement platform that allows customer-facing companies that are on e-commerce platforms to, without the help of a developer, create their own agentic systems. And we've created a builder where any brand can come on to our system in less than 15 minutes, have their own customized chatbot, and the chatbot allows them to upsell to their consumers. And what we are at the end is a core customer intelligence company. So we are gathering quite a bit of customer insights that are not otherwise available.

So you've been in corporate for quite some time now, but I see if I dig in your LinkedIn that in 2013 you were going on to like founder pitches, right? Like U-Debate. Tell us a bit more about that one and how you got ultimately engulfed in the corporate world for like a decade.

Yeah, that's a great question. So I, I think I've always been an entrepreneur at heart. I started my first company back in 2012. The company is called uDebate, and it was an online Reddit platform. It was one of the earlier Reddit adoptions. Anybody could go online and have— the idea was to have debates that were more cohesive than Twitter, similar to what Reddit is today. So I could have been the original founder of Reddit. But I don't know, because it had a different idea for me.

But, but what happened? That's easy to say, like Reddit, uh, think like the three guys put Incredible Hustle, right? They were YC, one of the first YC company. What happened?

Well, I think what happened was my go-to-market at that time was a little bit weaker than it should have been, and I didn't put enough formal marketing behind getting U-Debate out into the consumer space. And then one thing I had done too that I would do differently now is I did some successful partnerships. I did have partnerships with schools. I picked a vertical, which was K through 12, to, to allow students to learn to debate, but I just couldn't— I think go-to-market was a little bit weak, and then I had kind of burned out after 3 years. But we did go live. We had a couple early 1,000 customers and then a couple of really interesting partnerships. And then we moved on.

And why debates? What's the value behind debates?

I think so. I was a captain of the debate team when I was in college, and I think debating and having the ability to build a constructive argument but not have it feel like an argument, but have your point of view and your communication skills sharpened. Through debating, I think, could have been healthy. And then debating as a platform across political, like, conversational discourse was what I was going for at the time.

Because political debates—

Yeah, go ahead.

Because political debates nowadays, you know, like, I guess watching, like, presidential candidates debate is, like, pretty much the antithesis of what a good debate stands for, right? It's like trying to diss the other, find flaws in them, but good debates is actually trying to find flaws in your own thinking ultimately, right?

Or to find ways to construct your conversation in a manner that is not debatable, but in a manner that is like cohesive, linear thinking to get your point across. And that is something that is very helpful in all aspects of communication.

Yeah, I think it's one of the best ways to grow brain cells, right? Let's take it from this. You, you went to Salesforce right after that, then like Google for 5 years, which is a pretty long time. Google's incredibly good at keeping employees on. What brought you back to the startup world about 2 years ago?

Yeah. I went and I studied, and I knew at the core I was an entrepreneur and always have been somebody who likes to create, build, and lead teams. And, you know, corporate America gave me the structure. Google gave me the structure and the engineering backbone to start the second company, which is Checkout.ai. Um, and I used that— the skills and the organizational methodology that Google does to create the best products in the industry to create Checkout.

And Checkout, what's the general idea?

Yeah, as I mentioned, the general idea of Checkout is agentic commerce, and we are building it on top of multiple UCP protocols, which is Universal Commerce Protocol, to allow for consumers to gather the best products that are best for them. And our next phase of growth is going to be creating products that are the next. Let's say a consumer is looking for a product and they want price comparison or they want best product comparison across multiple platforms. That's what we're building and we're building an automated checkout.

And their priority right now is raising, right? Or is it finding customers? What does a day in your life look like?

Yeah, so my daily life is bifurcated into two main priorities. The first— well, they're both selling, right? Like fundraising is essentially a sales process in and of itself. So I'm fundraising for the company at $1 million on a SAFE note, and we are also growing our client base. And so we're doing that through partnerships, uh, and strategic go-to-market strategies for B2B.

And that million, wouldn't it be easy to raise just reaching out to ex-Google colleagues?

10 years ago would've been really easy. I think today it's just such a saturated market that ex-Google colleagues I have reached out to, some of them are my personal mentors today, but I am more focused on getting strategic investors versus like friends of mine who worked with me. Strategic investors who can help with go-to-market is the best play for us.

Okay, so give us an example of that. Like I'm, I'm incredibly good at go-to-market, right? So would I be a good strategic investor? Tell me a bit more.

Yeah, you'd be a great strategic investor because you have the right go-to-market strategy, which is a, you know, something that my team could definitely use. And then we are looking for investors who understand the consumer space, or if they don't understand the consumer space, they have an appetite for consumer tech. Consumer tech is what we are building. So we are not a consumer-facing company, we are a customer intelligence company, but investors that understand the need for consumer data and how that consumer data can help grow B2B businesses, which is what we're doing.

Got it. What current go-to-market channels do you currently have right now?

That's a great question. Being based out of New York City, the go-to-market channels that I primarily use are conferences. There's quite a big, huge consumer space in New York. So I go to a lot of consumer-facing conferences. I talk to my actual customers. I do research at these conferences. The second would actually be just cold outreach. Outreach through LinkedIn that has actually surprisingly been very successful. And then partnerships. So partnerships with companies that have something similar to what we're doing, but they don't offer the same product features. So we partner up with them.

I think we talked a little bit about the actual product on the tank, but isn't there existing competition to that? Like Shopify native chats that help people make better buying decisions. Isn't that something that's already like trailing, trailblazing right now?

Yeah, so there is Shopify native chat. There is also our chat, but the thing with Shopify native chat is it lacks a little bit of customization features and it lacks the ability to integrate into other systems. So we provide integration to your email marketing, Klaviyo, your ERP system, all of that out of the box. And then Shopify is not our only client, so we also have Wix, Shopline, all e-commerce brands. And rather than going through Shopify alone, we have diversified to a lot of other e-commerce providers to bring in more customers for us.

It's $250 a month, right? Isn't that like a very high price for normal small business?

So we don't target small businesses. We target businesses that have more than $3 million a year in ARR or higher. And primarily across the CPG, which is consumer packaged goods, furniture, any company that has a direct-to-consumer sale online. And $250 is very reasonable for the fact that we are not— you don't have to have a developer in the middle, and our system does not hallucinate. We've seen almost zero, near zero hallucination rates, right?

Instagram integration as well. What about the TikTok shop integration? Are you thinking about that?

Yeah, so that's part of our roadmap. We do already have an Instagram integration. It is a custom feature, so it does require the higher pricing tier for that because on our end we have to, you know, pay for the servers and whatever to set it up. But we have Instagram, TikTok, CRM integrations, and integrations into WeChat which are coming in a couple months.

Right. And if I make $3 million a year, right, that's $300K a month. If I pay you $250K a month and I get a 15% increase in my sales, that's over-the-top money, right? Like, that's over $40K in my pockets additional. That's the calculus.

Yeah, that is the approximate calculation. That is why we go for companies that have very strong Meta ad campaigns already in in their budget pipeline because in order for our system to show a high AOV, you have to be driving 5,000 to 10,000 site visits a month through Meta ads or whatever. And then we send the data back to Meta.

Got it. What's the structure of your company? Are you solo founder?

No, I have a founding team. So I have a co-founder, Namit Kapor. Then I have a founding NLP AI engineer. His name is Dhanush Kumar. So the 3 of us total.

So they all have some piece of the pie, they all have equity. Is that what you mean by founding?

Yes, we've worked together for over 2 years. We are equal, mainly equal partners in terms of strategic decision-making in this company's growth, and, uh, we each have a part in it.

You said conference, right? Like, why not Facebook ads or TikTok ads or Instagram ads where Is like how your clients actually have their clients buy. Wouldn't that make sense?

We are launching a meta Instagram ads campaign in a couple of weeks, um, and we have a strategic partner lined up for that. But keep in mind, we are going for companies that are over $3 million in ARR, up to $25 to $200 million. And at that point, to get to the decision maker, you kind of have to go to a conference or you have to go to LinkedIn. The bigger the company, I don't think Instagram's gonna be the way.

Yeah, yeah, true. Uh, cold email as well, right? Cold email and potentially launching your own podcast, interviewing them on a podcast and having them go down the funnel. That's the best strategy ever.

Yeah, that, that could also work.

Yeah, it works like crazy. How do you use your own product? How do you test it?

So we have a bot on our system on our main website called Sydney. So Sydney actually is our a Gentec AI system that I also play with sometimes. And then we have a couple of test pilot cases that are in the market right now, and that's how we gather our tests.

What is the backend? Is it OpenAI? Is it, uh, Mantropic? Like, what's the language model?

Uh, we use an MCP engine, and we are built across multiple LLMs. We don't use OpenAI. They do have a commerce protocol, but it didn't work with our system. So we use pretty much our built across Google Cloud.

Right. How do you manage your stress as a founder?

I have accepted that that is a part of the job and the title, and I signed up for this. I was not— it was either this or getting a job at another hyperscaler. And I knew that this was going to be the hardest and pivotal point of my career, and I just went in 100%. So the stress is part of it. But it's also the fuel. If I wasn't stressed out, I wouldn't be pushing as hard as I do, right?

And working at a big corp is like golden handcuffs, right? You're well paid, but sometimes sense of purpose might be missing. Plus, you know that they can let go of you. Plus, you know that there's no way in hell you can, I don't know, become a multi-millionaire working there, right? So, or let's say a dekar centi-millionaire. Is that the thinking?

I think there's roulette in everything you do. I think in startup space, I could become a multi-millionaire or super broke, or I could raise a bunch of money and become a millionaire, and that's the route we want to go. But at the same time, and hyperscalers, you do have a peace of mind, you do get golden handcuffs. You have— sometimes you can do very meaningful work at the bigger companies, providing you have the right team and the right, you know, purpose. Each to their own. I just— this is my second company, like I said, so I kind of had the entrepreneur fire from the beginning.

So do you want to scale it for a couple of years and eventually sell? Is that the, the plan?

The plan is to likely scale to hopefully $100 million and then sell or acquire smaller companies and then scale from there.

And what else is on the roadmap to reach $100 mil?

Right now it's our go-to-market strategy to get our first 100 customers, and then after that it is a feature set of the next wave of Agenta Commerce. That is what's going to get us to the $100 mil. It will be the next iteration of Agenta Commerce and how we implement and develop on that.

And what does that look like? Is an agent buying stuff for me? Like, give me a bit more details.

It's a little bit of agents buying on behalf of the consumer. It is a bit of agents also and companies being able to control how they can converse with the consumer, which is how it's traditionally been done. Consumers are— you make your buying decision based on what you know, right? And you know what you know based on the ads that you're seeing and probably a little bit of product research. So the ability to control how a customer-facing brand upsells to their consumer and how they do that amongst the competition. That's going to be the next wave. Oh, the next product that I bring.

Uh, who do you study nowadays, companies or founders?

Probably more the founder, more the founder in some companies. But I, like I said, I did a year at Stanford GSB, so I read a lot of case studies. And the case studies really helped me prepare for business. But I think the founder mentality and the founder grit is very important to understand.

So what specific examples do you study in terms of founders?

Right now I'm reading a couple of books where the founder stories are about starting from nothing and usually building, and their grit shows from the beginning, right? From like all the way from being in middle school to high school to, to being like the CEO and leader of, of the company that they're at. Most founders didn't go to business school. Most founders did not, um, come from a lot of wealth. It is the hustle mentality that gets you somewhere. I think that's something that I really strive for.

And where does that grit come from on your side?

For me, I think it comes from being the first daughter born in an immigrant family in the US and the constant need to strive. And then the— I do see a lot of bias in this industry, in the venture space and in the private equity space. And, and I see where the money is going and I can automatically probably very early detect whether a company is going to do well or not. And the lack of funding that goes towards female founders is atrocious. And it's just something that makes me work even harder so I can prove that, like, you know, female founders are very capable leaders and we are capable of building $100 million businesses. But that's where it comes from.

And what does that look like? Like 12-hour days? Like, how do you, quote unquote, balance your personal life?

I don't work 12. I really work 8 to 10 hours a day. I would say my Saturdays and Sundays, especially Saturdays, like I turn off my computer, I turn off everything and I'm just like meeting friends or I'm doing some self-care or playing tennis. Like I am very much somebody who's like very fitness oriented and it is important to have a work-life balance. You're never going to be a good founder or a good leader if you burn out too quickly. So it's important to get sleep. I sleep at least 8 hours. And it's important to eat healthy. It's important to, um, even if I'm working 6 hours in a day, they're very hyper-focused 6 hours. So my output tends to be higher than a lot of people because I work like very sharp on something for 30 minutes and it'll be done for a week. That's just how my brain works.

Interesting. So you have fundraising, you have GTM. This year, you have product, right? Like, what's your big one goal? Like, if you could like crunch any of these one big domino, which would be?

Well, it's a chicken and egg problem. I think the biggest thing is I want to get to my 100 paying customers.

And how far are you there? Like 20%?

Yeah, we're about 20% of the 100 paying customers. But then the chicken and egg problem is like, I need the I need to finish closing my raise. If I close the raise, I should be able to go to the 100 customers faster.

Yeah, you close chicken and egg with like just huge momentum, speed, and gigantic energy expansion, in my opinion. It's, uh, and I, I think you can make it, like, granted your background, all that. Last question, do you feel the Stanford GSB stuff was a good investment? Like, um, 2025 or '26 when you can get like most of your education with AIs Is it like about meeting other cool, ambitious, uh, people? Like, what was the thesis behind that?

Yeah, that's a great question. I went when I was working at Google at that time. Um, my manager just— and I were very like— she wanted to see me develop and grow, so she let me, um, do this program. And it is an investment in terms of your intellectual— for me, I need to constantly be surrounded by people who are working on themselves and who are intellectually growing. And I think the program offered that. I think the access to the professors is unparalleled. Professors at Stanford are the most brilliant in the world, and learning how they analyze and predict business predictions, it was very important. And I think the number one thing is the learning for me, the network being the second. I think it's— but I do really enjoy talking to classmates that went to Stanford GSB for various other programs. They are some of the brightest people in the world, and it's important to have that intellectual community of people I can, I can bounce ideas off of.

I love it. Where can people find out more about you, Anisha?

You can find me on LinkedIn, um, in dash Anisha Bhandari, or, um, yeah, and then just send me a message and I'll reach out.

It was Anisha and Charles Cormier for another founder