Helping Entrepreneurs Start Confidently - Sameer Gulati

0:00Hey, welcome to the CMO Whisper Show. I'm your host, Steve Olenski. Part marketing practitioner, part ad agency veteran, part journalist, I was a writer for Forbes for 10 years. I've had so many insightful conversations over the years with business leaders, to athletes, to celebrities, to of course, CMOs. The only difference now is instead of sharing those insights through written form, I'm doing it this way. My guest today is Samir Gulati, Chief Product Officer and President of Zen Business, and someone who spent more than two decades at the intersection of technology, financial services, and real-world business building.

0:41Now, Samir isn't just thinking about products, he's thinking about outcomes. At Zen Business, he's helping reimagine what it actually means to start and run a business today by bringing together AI, embedded finance, and automation into a platform designed to give small business owners a real shot at success. He's built his career across B2B, fintech, and business development consistently focused on one thing, how to create, scale, and transform. Not in theory, but in practice. And what stands out about Samir is that he doesn't chase trends. He builds systems that make those trends actually work for people.

1:24What a novel idea. Samir Gulati, we just met last week, and I feel like we've known each other forever. Welcome to the show.

1:31Sameer Gulati:Thank you so much, Steve, and totally echo that sentiment. It feels like we have known each other for a while. That is credit to you and how you operate. Thank you so much for having me here. And as I listened to that introduction, I just feel like that is so relevant today with everything going on. So super excited to talk about everything around access to opportunity for people and related topics. Yeah. And I have to disclaim this, if you will. Since we first met, I am a customer. So I am, and no, this is not a paid endorsement. It was complete irony that or coincidental that before we met, I started my LLC four years ago.

2:14And I'm a very, very satisfied Zen business customer. So we'll leave it at that. But it's, and if you need proof, I'll show you. Okay.

2:22Sameer Gulati:Well, thank you. That is better than a paid endorsement, right? Of course. I mean, people know me. I don't lie. I'm as honest as the day is long. So, and when we were talking off the air, and I really want to start with this because it's kind of fascinating, right? For those not familiar with Zen Business and just any company like that, not the single years out, but I'm talking to you, but you really start as a B2C company, right? You help someone like me become a business and overnight that you transform almost you serve, you become a B2B platform. And it's fascinating. And I'm curious, how does that dual identity, if you will, change the way you think about the customer journey?

2:59Sameer Gulati:That is a great question, Steve, and one which is exciting and challenging to solve. You know, what Zen Business and our entire company obsesses about is how do we make it easier for people like you and other Main Street business owners to become business owners? We're almost like that priest that anoints you as, henceforth, you shall be a business owner, right? Because we help you get your formation documents and get your business set up. And that gets us excited because that is such a critical time in somebody's journey around business ownership. It is high excitement and high stress. However, to what you said, it means that we're dealing with a consumer motion at scale, like a B2C motion when we're acquiring a customer.

3:48Sameer Gulati:But the moment they become a customer, we have to move into a B2B motion. And that creates some fascinating opportunities and challenges, which we have tackled by essentially having a very clear demarcation in our systems at the point of checkout. That was a conscious choice we made. But what's interesting is that the brand and the trust and the positioning and how we want customers to see us needs to carry across that threshold of checkout. And we've spent a lot of time, the company is now almost nine years old, and we have helped a million, close to a million business owners start their businesses confidently.

4:26Sameer Gulati:And, you know, an active subscriber base of almost half a million people that have a very idiosyncratic, everyone has their unique snowflake journey within our systems. So, yeah, you have touched upon something that is incredibly important. And we feel in many ways we're breaking new ground, at least at the scale that we're operating at. Yeah, it's, I would imagine, and I'm not going to put words in your mouth, but you come in as, I hate labels, first of all, but, you know, the B2C versus B2B, right? At the end of the day, yeah, I guess technically my company and all the other people like that are, quote, businesses, but we're still people.

5:06Sameer Gulati:That's right. And, you know, that is a very important philosophical distinction that we anchored on really strongly early, which is, and this may feel like a subtle point, Steve, but it's a really, really important one. Are you solving for the business or are you solving for the business owner? And the moment you make that subtle shift, there are meaningful implications. And certainly that chasm between B2C and B2B doesn't disappear, but becomes significantly smaller because now the individual that you are trying to help start a business and is now the same individual that is running the business.

5:42Sameer Gulati:And so that orientation of who you're solving for, is it the business entity or is it the business owner, is a critical mindset shift, which has helped us a lot. The other thing I will say is, and this warms my heart no end, is that business owners have multiple businesses, right? And sometimes a business doesn't work out, or they have to put it on ice, but they always seem to come back. It's that spirit that endures. And so we feel great about focusing on the business owner versus narrow-mindedly focused on, well, what are the businesses' needs? What do you think? And again, I hate labels, but we all live by labels.

6:25And I've worked at a big company like Oracle in my career, and it's one of the biggest B2B companies in the world. There's got to be a ton of things a big or any size B2B company can learn from that very unique dynamic your company has from entry point to then becoming the B2B person. What are some things you would coach or advise a traditional B2B company to learn from how your company treats customers and then manages that relationship?

6:58Sameer Gulati:A couple of things, particularly at the small end of small business. So people, speaking of labels, folks use SMB and enterprise, and there's that whole spectrum. On the small business side, any company operating in that, I think that you might wish that people should separate their personal from their business and why they're commingling stuff. There are things that you can wish for and there are things that are just reality, which is business owners commingle, overlap their personal and business side all the time. And frankly, trying to force that separation may actually be artificial and not something that is in the best interest of the business owner in many cases.

7:38Sameer Gulati:And I think it's worth anyone operating in this space of helping small businesses should honestly embrace that and versus fight. I've seen so many companies trying to force and convince business owners that it is bad to commingle stuff. Yeah, sure. But the reality is that they do. You're a business owner, Steve. It's very hard for you to draw a clear line between what is personal time and time for your business. Of course, you try. You compartmentalize so that it is more manageable. But the reality is there's a strong overlap. So that would be the first thing I would just say, which is rather than try and shape business owners into the mold that suits your business mindset, embrace who they are.

8:22Sameer Gulati:And I promise you, it will be one of the most fulfilling decisions you will make. That's one piece, which is, I think, critical. The second one I would say is there is a tendency to believe that in the B2B world, it has to be people-driven account management and customer success. And we have shown at Zen Business that you can have systems and technology in place and still be very, very human about the interaction. And I think that's a big unlock, which is it is not either it's people based account management or be very human. Right. You can actually do both. And particularly now in the world of what AI makes possible, this may seem counterintuitive.

9:05Sameer Gulati:You can actually be a lot more human using this technology. Which sounds counterintuitive, right? It is, absolutely. And that's the point. And well, I think if you just look at, again, what really matters is what you're focused and centered on. If you're focused on how do I use AI tools and AI technologies, you will absolutely go down a much more sterile, less human path. But if your orientation comes back to what is fundamentally driving this business owner to be in the business itself that they're running or multiple businesses they're running, and how do I use the latest tools in the AI world to enhance that experience and keep that very fundamentally human endeavor entrepreneurship alive and accelerated, I think you will not have to make the trade-off between scalable use of technology and being very human about it.

9:57Right. All right. Put your product hat on for a second. Yeah. When your customer evolves from, say, idea stage to actually operating a business, just as I did years ago. How do you make sure that your products evolves without overwhelming people like me?

10:11Sameer Gulati:It is a constant battle, to be honest. And here's why. When folks are in the ideation phase, they are rightly and they should be absolutely excited about the possibilities. And when they decide to finally take the step from ideation to actually forming a business and they find us, we have a balance to strike here, right? Our positioning and our promise And our commitment is we will take the friction out of that entire process for you. And for some reason, which is a much longer and significantly more boring conversation about why there is so much friction we introduce in front of business owners.

10:48Sameer Gulati:At that point, we want to be your guide and make you aware of all the things that you have to do the moment you take the step into formal business ownership. But we also don't want to overwhelm you. So our promise is that we create awareness of all the things, the different government agencies you need to deal with, but our promise is we will take care of all of that for you. What you're faced with is a very simple choice of one of three packages, right? Like starter, pro and premium, which comes with a whole host of services, none of which overwhelm you with, how do I deal with the local secretary of state?

11:21Sameer Gulati:How do I interact with the IRS, USPTO for my trademark searches, right? And so that's how we approach it because look, One of the most important things we're trying to solve for is how do you and other business owners get started with confidence? And that requires a balance of enough information without it being overwhelming. Do we always get that balance right? No. But are we always trying to get that balance right? Absolutely. It is a balance. And again, I can speak from very, very firsthand experience. it can get it can very easily fall into that oh my god i'm overwhelmed with stuff that i don't even know when i'm reading half the time but none of that happens none of that happens in this experience is extremely user-friendly for it for a not so smart guy like me to go no we got you right and i personally i can't tell you how much that means to go look i don't know how to run a business i don't know the backend stuff of this.

12:20I know what I know and I know what I don't know. And that's why people rely on people like you and the brand to go, we got you. So that's a big, big plus. It really is. And I'm not blowing smoke because I'm a customer, but it's the truth. And I think there's a lot of lessons for brand marketers and CMOs hearing this to go, and people have heard me say this word a lot, Samir, it's simple, right? Keep it simple.

12:45Sameer Gulati:That's right. Very, very true. That completely resonates. And you asked me to put my product hat on and that simplicity and the trust is we got you. You don't have to deal with it. Creates a product challenge and creates an engagement challenge because now I have just committed to you that your ideal experience with Zen Business is after you form with us, we got you. You don't actually have to do anything. We will take care of it, which means that it is not a high engagement, high repeat engagement experience. In fact, my best experience I can deliver to you is literally no experience at all. That's the most frictionless experience you can have.

13:24Sameer Gulati:And today what we do is we will let you know when you have to take an action. We will monitor your business entity and make sure it stays compliant. And that creates a whole host of different challenges. But we are absolutely committed to what we call internally D-I-F-M, do it for me. That is a very core ethos of our product development. And that shows up in our marketing and brand promise. Now, we recently launched Velo, which is short for Velocity, which is our agentic AI experience. And I'm so excited because that is actually helping us bridge the gap between keeping the confidence high, keeping a conversational guide available to you 24-7, but also creating that sense of ongoing engagement and almost like having a co-founder with you.

14:11Sameer Gulati:So, you know, we're only six months in, but we've been absolutely blown away with the reception that's gotten and just how useful people are finding it. You read my mind. I was going to transition into Velo, sorry. It's the AI Power Platform, right? And my first question about that is like, what problem would you say you're trying to solve that didn't exist before? Great question. And honestly, more people should be asking that question when deploying AI technologies, right? The problem we were trying to solve was twofold. One, folks wanted, a big reason why people come to Zen Business is they're looking for access to that expertise and they're looking for a company or a team that they can rely on to do it for them, right?

14:56Sameer Gulati:And we want to make that available 24-7. And you can solve that through humans and you can solve that through chatbots, but what conversational AI gives you, particularly feeding off of the last nine years of helping almost a million business owners, really rich contextual information. What conversational AI in the form of Velo gives you is the ability to offer that support, that expertise, that guidance 24-7 on your own terms, right? Business owners don't follow the nine to five. Many of them actually have a nine to five, and then they're running their business in the evenings and nights and weekends.

15:31Sameer Gulati:So that was one thing that we were looking to solve for without compromising the deep expertise that we have built in this space over the last many years. The second thing that we were looking for, Steve, was when people are engaging with us, chatbots and conversational agents have gotten pretty good at giving you specific, correct information. With Velo, we were looking to push that to, can Velo act on your behalf? Take more off of the plate of the business owner. And because Velo is built on the infrastructure of the business, which we have painstakingly built over the last nine years, including integrations into different sectories, state and the IRS, Velo can actually take action on your behalf on the platform.

16:15So those are the two things we were looking to solve.

16:17Sameer Gulati:One is making our expertise and guidance available 24-7. And the second was taking more work off of your plate. And that's where the agentic aspect of AI is something that we're so excited about. Yeah, I know you've talked about in nine years is gonna speak to this. When it comes to AI, prioritizing trust over speed, it is such an easy trap for anything, for any business to just drop it into chat, drop it into claw, drop it into Gemini, pick your tool and just go at warp speed, literally, versus, you know, testing what it's telling you kind of thing. I'd love for you to talk about why that is so important to prioritize trust over speed, not just in your own world, but just anybody listening to this when it comes to AI.

17:03Sameer Gulati:Yeah, this is so, so core to, you know, you asked the question of what problem were we trying to solve? I think once you get that clarity, the next question you have to solve and be very clear about is how you're going to solve that problem. And for us, maintaining that trust with our customer was so, so central. It wasn't even up for debate. And also very conscious about making an explicit choice that we will not compromise trust for efficiency. Because to your point, it is so easy to say, hey, let's use the latest tool and it'll give the answer. And if it's good enough, that's good enough. At least we didn't have to hire someone else to do that.

17:42Sameer Gulati:And this moved my gross margin from 85 % to 85.2 % and we can declare victory. The approach we have taken is if Velo is ever in doubt, it taps out and hands off to a human. And, you know, my direction to the team was make sure you get it right. That's the first bar we have to clear because our brand promise is one of you can rely on us, you can trust us, not just to give you the right advice and guidance, but actually to act on your behalf and store all of your entity information, et cetera, which is a pretty high bar for trust, You're not just buying shoes on the internet, not that people don't agonize over shoes on the internet, but it's a very different situation.

18:24Sameer Gulati:There's no return policy on having formed your business. And so we take it very, very seriously. And frankly, Steve, in what we do around compliance services, business formation, fintech workflows, the cost of getting it wrong is genuine and it's high for our business owners. And so our approach has been build a very stable, strong foundation, feeding off of only our internal data and expertise. We do not rely on public information because, you know, some Redditor, even a well-meaning Redditor, may give out wrong information. A lot of the public LLMs are feeding off of that. We constrain Velo to all the knowledge that we have garnered over the last nine years.

19:04Sameer Gulati:And when it's in doubt, it'll hand off to a human. Now, what we are doing is we have put in some really exciting tech, which constantly assesses Velo's conversations and helps it self-improve. So we can tell whether Steve, who's had a multi-threaded conversation with Velo, is having a positive experience versus Samir, who's having a multi-threaded conversation with Velo, is having a frustrating experience. And he's having multiple threads because he's not getting the answer he wants. Velo learns from that. So I think we needed to start from a place of trust. We're committed to it. And now we're using technology to grow that surface area, but without compromising the trust.

19:47Or the human side, obviously.

19:50Sameer Gulati:That's an interesting question. So the humans are still there. I would actually characterize it as as Velo is improving, we are making that experience more reflective of the human conversation. And what we're learning, Steve, here's an example, right? We took all of the transcripts and conversations, anonymized, of course, of our top agents who got five-star Trustpilot scores on those conversations and fed that into Velo, not for content and expertise, but for tone. And that is the richness that AI is now capable of. The other thing that we're learning, and I wrote a little piece on LinkedIn about this, is what has been very interesting and, dare I say, slightly disturbing, is that people are being more honest and more open with Velo than they have been our very trusted human colleagues in the past.

20:46Fascinating.

20:48Sameer Gulati:You wouldn't have thought so, but I think there's something about the anonymity. There's something about not feeling judged. There's something about being a lot more vulnerable to a screen or to a device than to a live human, even though it's on the phone. Folks are literally asking Bello about life advice. Folks are like, hey, I am getting divorced. Should I move my assets into an LLC? I am thinking about some life changes. I wouldn't go into those details here on this podcast, but I'm thinking about certain life changes. How should I continue with my business? That's the kind of question that is so vulnerable and so honest.

21:29Sameer Gulati:I don't know what you think, but this is not what we were expecting. I'm not surprised, to be honest with you. I mean, my AI tool of choice is ChatGPT, right? And everybody's got their own favorite. But I was just having this conversation with somebody about it's scary how much my chat knows me already. That's right. And I'm constantly going, does this sound right? Does this make sense? What should I make for dinner? What? It's scary. It is. And look, Velo also has memory. And so now when you log into Zen Business, Velo greets you proactively and basically asks you, do you want to pick up where you left off?

22:09Sameer Gulati:Right. You were thinking about hiring employees and you were looking, you asked me about payroll last time. What can I help you with? And when you marry that with the very human tone that it is getting trained on, and you marry that with 24-7 availability, that's a very powerful combination. It is. And then you add the ability for that, for Velo to act on your behalf. That's the bet we're making, that we can fundamentally help business owners spend more of their time doing what they love versus getting drowned in all of the compliance and financial activities that they have to do, but don't want to do.

22:47I have my hand raised. I love it. You have to do it, right? And the more help someone like me, and I'm going to say I'm probably in the majority of people who don't either like doing it or know what they're doing. The fact that I can trust that, I mean, trust is, This is not about what to have for dinner. These are legal things. These are IRS. This is serious stuff.

23:12Sameer Gulati:That's right. It is. And that's why that is an unshakable, unrelenting principle for us in how we think about brand, how we think about marketing, how we think about product, how we think about operations, how we think about technology. Every single aspect of what we do at Zen Business is anchored on that. Before we get to some fun, and I ask you some random five questions. so the audience gets to know you as a person. I want to ask you about something. You've talked about the rise of the builder. How do you define that person today? Oh my God. So here's what we're seeing happening. There's a lot of talk right now about the jobs that AI will replace.