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Building a business is tough. It takes grit, never-ending days, missed family birthdays, and more coffee than you thought it was possible to drink.
Unfortunately, many business operators do all of this and see initial success but then - crickets! They hit a plateau or, worse, fall off the cliff entirely.
This is The Business OS, a show powered by JustCall dedicated to ensuring that you don't get lost in that Bermuda Triangle of irrelevance.
Join us as we talk to entrepreneurs, business leaders, and real-world operators - folks who know your struggles better than anyone else. They are also the ones with the knowledge and playbooks to help you succeed. Through candid conversations with our guests, we make sure you’ll walk away with actionable takeaways to help you think ahead and pivot fast.
True, building a business is tough - and you have to hustle. But it does get easier when you have a Business OS.
Shruti Kapoor [00:00:00]:
I think the one thing that I would probably have done much more of, and done much sooner of is connecting with a lot more other founders who are going through the journey for two reasons. One is, you know, of course you can get the tactical advice and commiserations, but I think it also gives you a sense of understanding that, like, you know, every time you're failing or you're feeling down, like you're not the only person making a mistake.
Kushal Saini Kakkar [00:00:32]:
This is The Business OS, a conversation powered by JustCall, dedicated to giving you the tools and knowledge needed to win your business. This episode and guest are really close to my heart because whenever someone asks me what true leadership really looks like, I always say her name. Our guest today started her career with stints in Morgan Stanley and intellectual ventures and was part of the founding team at Payoneer India. This was her first role in sales, and it was here that she discovered something that salespeople have always known. There is a huge disconnect between sales, product and marketing, and no one was doing anything about it until she did something about it. Anything is possible. And with some help, she made some calls, pulled in a couple of friends, and in 2018 created Wingman. In the beginning, it wasnt easy because it never is.
Kushal Saini Kakkar [00:01:23]:
But the iterations, the tweaking and the grind didnt stop. And when they sold to Clari in 2022, Wingman was a mainstay in sales circles. She continued to Shepherd Wingman, now Clari co-pilot, as the head of international business at Clari, and today the world is her oyster. She is also a trained life coach and fantastic mentor to founders starting their journey. Folks, so glad to have here with us an entrepreneur, life coach, mother, author, mentor, and my friend Shruti Kapoor. Shruti, so great to have you here.
Shruti Kapoor [00:01:57]:
Thank you. That was a very generous introduction.
Kushal Saini Kakkar [00:02:00]:
Absolutely befitting for someone like you, Shruti, just to get started, when you go right back through all of your entire journey, when you started your career, was entrepreneurship a goal at all?
Shruti Kapoor [00:02:14]:
No, I would say I was too chicken to do entrepreneurship is what I always thought. But, you know, I think over the years, as I got maybe somewhat more jaded with corporate life and somewhat more inspired by other entrepreneurs that I met along the way, I definitely wanted to give it a try. I was okay to fail at it, but I was like, if I don't do it, then I will regret it. That's what got me started.
Kushal Saini Kakkar [00:02:45]:
So what really made you decide to take that risk and finally that leap of faith? Was it a calculated decision? And I would expect nothing less from someone who's as good as numbers and makes calculated decisions. Comes from a science background, right? Was it a very calculated decision, or was it just, you know, one of those moments that turn out to be defining moments?
Shruti Kapoor [00:03:05]:
When you look back, I think you can never do entrepreneurship with calculation in the sense that the odds are always against you. And so it's always about, like, taking a leap of faith and being more optimistic than you deserve to be. And so it was a lot more about saying that, using the regret minimization framework to say that if I don't do this, I will regret it. And so let me do it, and, you know, hope for the best and, you know, give it your best.
Kushal Saini Kakkar [00:03:39]:
Wow. I think that's a really good way to think of, you know, when you're making major decisions in life, is the regret going to outweigh, you know, the risks and, you know, everything else that comes down that road? So I think that's a great way to think about it. You obviously built Wingman with two co founders, Murli and Srikar, and shout out to these folks for being some of the best founders anyone could ever work with. Three is famously a crowd, and you folks made it work so seamlessly, or at least it looked like. How did you folks make it work?
Shruti Kapoor [00:04:08]:
So I think some early advice that we got was, yes, founders will do a bunch of tasks, and you won't have very well defined rules, but pick your titles and use that at least as some sort of a defining function. I think that was helpful. Sometimes the mistake that I see people make is either they tend to be too much parallel tracked, which is to say that they are like, you do your thing, I'll do my thing, and never the twin shall meet. Or they tend to have one function where two people are working really closely. So I think very early on, even before we really had any formal structure, we kind of chose what our titles were going to be more so that it helped us align ourselves with the roles that we would play. And what that meant was that the person who had that title would have the last say on that particular decision, on that particular function, but it didn't mean that we wouldn't give each other advice or bounce ideas off each other. And that was a very conscious journey to say that, yes, we will, you know, bounce things off each other, but we will let the other person have the final say. And I think that structure worked well also.
Shruti Kapoor [00:05:30]:
I think just to the number three. It's interesting. I feel that it brings a lot of balance because I think if it's two people, there isn't really a way to do a tiebreaker. But if it's three people, then, you know, after you finish listening to two people's point of view on some difficult decision that you're trying to make, um, you know, it's easier for you to go back and reconsider things because one person might have a very strong opposing point of view. The other person might have, like, a midway point of view. And that gives you kind of, you know, multiple options to think. And I think it opens things up.
Kushal Saini Kakkar [00:06:02]:
Shruti, for anyone, you know, and especially founders, to really work well with each other, there needs to be a large amount of trust, right? And this is true for all relationships, really. But even more so in the case of co founders, were you able to build trust right off the bat when you started off building the company, or was it a gradual process?
Shruti Kapoor [00:06:23]:
It was absolutely a gradual process. Right. So just for the context of everybody who doesn't already know us, I didn't know Murali and shrieker before I started the company with them. I had met Murali maybe a year, year and a half before I started up, but largely in the context of a common friend introducing us to startup together. I had really not met Srikhar till we started up, and we were sitting across the table bouncing off ideas. He had quit his job and moved back to India with the purpose of starting up. So there was definitely that pressure. And I think the good thing was that we had all worked in the corporate world for ten years at that point in time.
Shruti Kapoor [00:07:02]:
So we were a little bit more, I would say, mature in our emotions and also in terms of just seeing what is out there. And I think trust building is about two things. One is, it's about understanding that what that person is saying is true and honest. But I think it's also, secondly, about understanding what is their driving motivation, what are their value systems, and having that compass aligned so that, you know, in which direction will somebody go if something happens. So I think over a period of time, we realized that we needed to do the work to build that. And in some ways, actually, some of our investors were helpful in that. Vice was helpful in that. So it wasn't the playbook that we were creating from scratch for ourselves, but I think that we were very conscious that it was something that needed to be built, and it didn't definitely happen overnight.
Kushal Saini Kakkar [00:08:03]:
Shruti, there were obviously a lot of lessons that you must have learned along the way over the years, and I'm sure you probably look back fondly now at most of those hard journeys that you sort of did back then. What is perhaps the hardest lesson that you've learned in your entrepreneurial journey so far?
Shruti Kapoor [00:08:19]:
I think the one tough one is that people are the most important part of that building block. And, you know, it's very tempting at times to make the shortcut when it comes to making a decision on hiring people or even when it comes to trying to explain yourself versus so that you still give people enough autonomy versus driving a decision which could, you know, in the short term seem faster and more efficient way of doing things. So I think that's probably the tough lesson because I think there were definitely decisions that we made around, like bringing people on board or, you know, the way you bring somebody on board and, you know, how do you decide what that person already knows and what is it that you need to educate them on? I think those are all kind of tough journeys that you learn along the way. And I think it's just, it's a lot of gut and a little bit of science, and I think it's just that you have to develop that instinct and you also have to learn to trust that instinct. And very often it's not. I think the instinct on the negative side is stronger than the instinct on the positive side. So what I mean is, like, if you get the instinct that you shouldn't hire somebody and you're not able to explain it, you should still maybe just go with that instinct, especially early on. But, you know, sometimes it's easy to convince yourself and it also seems like the faster way to get ahead.
Kushal Saini Kakkar [00:09:55]:
Yeah, I think I absolutely resonate with that part. Right. As you know, in my role, I sort of look at profiles, speak to candidates, obviously bring them on board, do all of those things. And many a time you do have a gut feel about a candidate. And it's not sometimes easy to put words on gut feels. Right. It's not easy to put an exact word that is acceptable in corporate circles and is something you can add as feedback on a recruitment tool.
Shruti Kapoor [00:10:23]:
Right.
Kushal Saini Kakkar [00:10:24]:
And it's hard to kind of make sense of those. But there's a lot of wisdom behind what our mind is telling us intuitively. And it makes a lot of sense to really listen to those signals as well and find a way to really communicate them across, you know, the folks that matter in that decision, you know, talking about hiring an instinct maybe a little bit more, what were you looking for? Perhaps when you are hiring for your fifth employee or your earliest employees versus, say, your 50th employee, how did that change, or did it at all?
Shruti Kapoor [00:10:53]:
It definitely changed in some ways. I think for the first ten people that we hired, we were very clear that more than the skills, what mattered was, even though we hadn't really written down our values or our culture, was that we instinctively felt comfortable with the cultural alignment and the value alignment with that person. And I think the reason for us was very clear. We realized that each person that you bring in early on is going to have a ten x impact on the culture that gets created in the company later on. So we felt that it was very, very important to get that right, even if maybe it took longer to onboard somebody, or maybe that person didn't have exactly the profile that you were looking for or the, you know, the experience level or whatever. Right. So I think that was a big part of the consideration early on. And I think over a period of time, as you're trying to scale the team, you realize that, okay, you know what, the culture is kind of maybe 70% there, right? So you, of course, don't want to bring somebody who's a cultural misalignment, but that's not your biggest, um, decision criteria.
Shruti Kapoor [00:12:05]:
Uh, and then I think the second thing is that early on, we would, because of the cultural element, irrespective of what we were hiring for, all three founders would meet every single hire. Um, but later on, you know, that was no longer the case. We would try to the best of our abilities to have at least two founders in the loop. Um, but, you know, that changed as well. And I think, uh, over a period of time, as you have strong people leading the teams, you also want them to be able to play a role and have nuances based on their own personalities. So I think that is the other thing that comes in.
Kushal Saini Kakkar [00:12:44]:
I think from my own experience, considering I worked with you at Wingman, I think one of the things that Wingman famously got right was that everyone seemed empowered, and they were truly empowered. They did truly feel like they owned a, you know, what they were working on or the progress and growth of the company overall. So I think there's so much to be said for actually bringing on board the people who are the right culture fit, but then also making them feel like, you know, that company and the growth and the journey is also theirs equally. And that's not a very easy thing to achieve from the perspective of someone who's worked across multiple companies and with multiple folks. Right. There's always some incredible learnings to be done, whichever experience we're in. But I think that was one of the strongest things that I think perhaps anyone who worked at Wingman would have felt at that point of time coming closer, Shruti, to, you know, of course you raised funds through y combinator early on. Any advice for entrepreneurs who are trying to do the same thing today?
Shruti Kapoor [00:13:43]:
So I think, you know, just more broadly on the fundraising piece, I think it's one is it's important to just get the perspective on what other driving metrics for a fund versus for an entrepreneur and to also just be conscious of the fact that not every business is a fundable business, right? And that doesn't mean that it's a bad business or the business shouldn't exist. It's just that in the VC view of the world, that's not a business that they would support, right. So if, you know, if I'm starting a business to open a school, there is its not something that I should go to a VC for. I should probably go to a bank and get a loan. So I think one is just understanding whether or not a business even fits into the venture capital model and therefore understanding what is the venture capital model. So given that I came from a finance background that was much more intuitive to me, and later on I realized that it wasnt as intuitive to everybody. I think one is that two is also understanding each stage of the business. The different investors that are coming in are taking different types of risks and therefore understanding and working backwards to say, hey, what are the two or three risks that an investor at this stage of my business is taking? And how do I help them understand that I have de risk, some of it? Or how am I thinking about those risks? Because I have seen early stage founders sometimes, you know, fretting over like, how do I make my five year projections? I'm like, that's like, nobody cares about it.
Shruti Kapoor [00:15:25]:
Yes, they might like ask you for how you're going to spend the money, but they know as well as you do that you have no idea how you're going to spend the money or what's going to happen. And like, nobody is going to judge you on the fact that you projected that you are going to have 25 employees at the end of year two and you only have twelve. So I think that's so one is to understand, like, what are the big questions that they're trying to answer? And I think for us, again, some of those things we got indutably right because of the experience that we were coming from. But I think some of those became much easier because of the y combinator experience. And I think the thing that is, you know, it's somewhat hard to execute in isolation is the fact that anything, whether that is fundraise or that is m and a or that is in some cases even doing a large sales deal is a little bit about creating some sort of a fomo and an urgency. And I think that's the thing that sometimes people don't realize. And I think even when it comes to hiring, for that matter, you have to build a pipeline for you to get the best outcome. If you don't build a pipeline and you think, I'll do the shortest path to this, you'll not really get there with the results that you want, and the results can look very different.
Shruti Kapoor [00:16:52]:
So it's like if one person says that, hey, I have this great designer and I'm going to refer this person, and you say, I'm not going to run a process for it, the chances are that the designer might have been great in a different context, but you didn't know what you were hiring for, what needed to be great in your objectives, function and all that, right? So the same thing applies for hundreds. If you go out there and you're like, okay, you know, I met these two investors. Somebody referred them and they are willing to put money. Should I just go with it? Right. So I think it's the same thing. The terms that you get for that fundraise might not be great, the investors themselves might not be great, etcetera, you know, and I think the thing on trusting your intuition applies as much to investors as it does to recruiting somebody. Right? So, like, if an investor is consistently showing up like ten minutes late on a call, and, you know, they're not, they're not worried about your time, right? So maybe they're not the people who are going to value you in the future.
Kushal Saini Kakkar [00:17:50]:
Yeah, I think that's a great way to think about it, to kind of use that gut lens for a lot of things and also understand that there are sometimes no shortcuts, some things you need to build and sort of nurture over time as well. So I think those are really powerful lessons for anyone. Wingman, of course, we know, was acquired by clarity, and that must have been an interesting journey. I'm sure we saw some part of it as employees, but there must have been so much more behind the scenes that we didn't get to see. What mistakes do you think founders do at that stage during acquisitions and perhaps things that you learned from your experience?
Shruti Kapoor [00:18:25]:
The best time to sell the company is when you're not selling the company. And it's the same thing that applies to fundraisers in some sense as well. I think the challenge is always that people either get too attached to what they are building. So it's like, this is my baby, and how can I let go of it? I think it's useful to constantly be able to take an outside in view of whatever things in life, right? So, you know, if there's a skill that you're looking to build, I would say, like, build the skill of being able to take a different point of view and look at the same situation in whatever aspect of life you are in. So I think for us, one thing that we learned was, okay, you know, what if five people are saying something, and even if you strongly want to not believe that, can you wear that hat for, like, five minutes and look through and see what does the world look like? And it's okay if you come out of it saying, you know, this is not my view of the world. I think just from the acquisition standpoint, the other mistake that people make is they either get to Gungho about the process too early on, Orlando. They don't realize when the trigger is getting pulled. I'll just break that up a little bit.
Shruti Kapoor [00:19:59]:
Very often I get calls and emails from founders who just received an email from somebody who's like, I'm interested in your company. Let's set up a call. And they're all excited, and they're like, this is an acquisition offer. And I'm like, no, this is not an acquisition offer. The second thing is that when you get a communication like that, oftentimes people are like, okay, you know what? Now I want to get on the call so that I can know what is the number they are offering me. Right. But the fact is that they're not going to offer you a number on that first call. They are going to have to look at a bunch of data, get to know you better, do a bunch of things before they'll get to any semblance of a number.
Shruti Kapoor [00:20:42]:
Right. And so, you know, the decision that you have to make is, do you want to engage with them to the level that you even get to a number? Right. Because in getting to a number, you're going to have to reveal a lot of your data and details that, you know, if that person is a competitor in the same space, you might or might not want to. Right. But this other more personal decision from a founder standpoint is to also say, if there is a number on the table and I walk away from that number, will I be able to live with myself and go at my business with the same enthusiasm that I am going at it today? Or will that number always be a lead block weighing me down and saying, hey, you know what? Maybe I should have done that. Every time something is not going right in your business, will you be like, oh, shit, I left that on the table? So I think it's important to understand that decision is as much personal as it is a business decision. And the business decision is not in isolation of the environment. Right.
Shruti Kapoor [00:21:51]:
So it's a business decision, but it's not just about what's happening in your company or what you're building, but it's a business decision in the context of how the competitive landscape is evolving, how the economy is doing, what is the investor sentiment like? There's a bunch of other things that come into play, and if it's a technology business, and also how's the tech landscape evolving? So there's so many things to consider, but it's important to know that each of those is a deliberate decision to make and not just kind of walk into it and get all excited because you got an email, wow, you make.
Kushal Saini Kakkar [00:22:31]:
This journey of entrepreneurship sound much more tougher than one would think it possibly was. I'm curious, and I have to ask, do you think it's easier to build a company or sell a company, considering they both seem like a lot of work? Clearly.
Shruti Kapoor [00:22:47]:
I think, of course, you can't sell a company without building it, but also the fact that a lot of things that you need to do to get to a good acquisition outcome is essentially building a good business. Right. If the business is fundamentally good. Right. And you're not just trying to, you know, kind of fool somebody into buying something, then, you know, you're going to do the right thing either ways and it's actually going to be the same journey. Right. So it's not very different. If you were to say that I'm building this as a business that, you know, I want to die building, or if this is a business that I'm going to build and sell in four years, it in both cases, like, the fundamentals that you should operate on should be the same.
Kushal Saini Kakkar [00:23:35]:
Shruti, you know, earlier mentioned how you shouldn't get too attached. You know, this is a baby, and people tend to get too attached to that. You know, talking about babies, you, of course, raised, you know, your child while you were raising Wingman as well.
Shruti Kapoor [00:23:47]:
Right.
Kushal Saini Kakkar [00:23:47]:
And of course, there must have been some balances to do there as they are with any parent really. How is it to maybe balance a more emotional side of being a parent versus the more practical side of being a founder? Like, were there any sort of balances to be made there?
Shruti Kapoor [00:24:02]:
I thought that there would be more balances to be made, but I think over a period of time, I realized that you have to embrace your personality as you build a business. Im assuming that the question is really to say, hey, was there an emotional aspect to building the business? And was there a practical aspect to building the business? You know, were they sometimes at odds with each other? I would say that it's easy to feel that sometimes they are at odds with each other. But, you know, if you truly say that you have to be authentic with yourself and you have to build the business with the values that you hold important to you, then it actually doesn't feel as much of a kind of a departure from each other. And I think, like, it's maybe harder for people who come from a background that is maybe not as common in whatever business you're building. Right? So, you know, of course, being a woman building a tech business, you know, not that common being in India trying to build a business for the US, you know, also not that common if you look at it from a US lens. So I think it's easier to then question yourself and try to fit yourself into a mold. But then, you know, over a period of time, you realize, you know, what? That mold and me are just not aligning. So let's just, you know, not try to fit into the mold.
Shruti Kapoor [00:25:26]:
And I think that's kind of maybe the best approach to do it. And they're going to be practical things that you should adopt. But I think it's more important to just realize that you're not going to fit into everything and so choose what you're choosing to not fit into and have a good reason of why you don't want to fit into it.
Kushal Saini Kakkar [00:25:46]:
I think that makes a lot of sense. And I think that's not only for people who are entrepreneurs or founders, but I think for whichever paths we choose in life, I think whether that's roles, companies, even as employees, there are clearly so many choices. We can choose to be our authentic selves at work or we can choose to have a more corporate sort of front setup. And that's a choice that I think we all make every day that we go to work. On a slightly different note, I know one of the things that used to sort of tick you off in some ways was being referred to as a woman entrepreneur. And I think that was because we hoped for a world where it didn't matter to have a woman or man in front of that tag of being an entrepreneur and nothing else. It's not to say that we don't celebrate who we are. I'm curious for women who do want to be entrepreneurs, right? What advice do you have for them?
Shruti Kapoor [00:26:38]:
When I went into the world, I was a bit more naive and, you know, maybe the naivety helped in the sense that I actually went ahead and did it right. I think if I had, like, read all the stats on, you know, how the world is so much against women and, you know, how only x percentage of funding goes to women led companies and blah, blah, I might have been discouraged, right? So I would say, like, you know, anyways, as an entrepreneur, the answer against you, it doesn't matter if you're a man or a woman now. You might as well just begin to ignore the stats because so much of the data is just going to make you feel so discouraged. So it's okay, just go out there and give it your best shot. But I think it's also important to be aware that biases exist and it's useful in some ways to understand how you might anticipate and overcome them. You can use that, uh, knowledge to your advantage. Right. So an example is like, I didn't, I didn't realize that when I walk into a room, uh, you know, pitching to investors, they are of course, seeing the company and they're seeing everything else, but they're also seeing me as a woman entrepreneur and whatever biases that they come into the room with about women, right.
Shruti Kapoor [00:27:55]:
Whether that is, you know, they're not as career oriented or whether that is, that they tend to be softer and more emotional, they are going to come in with those biases, right? And they are going to be the filters that they are using somewhere in their head that are going to be unsaid. Now, of course, I don't have to go and overcompensate for it, but it's like, if I know that this is a question that somebody is not asking, but they want an answer to it anyways, by the time they get out of the room, I could be smart in answering that unsaid question and, you know, play that to my bond. So I would say, like, be optimistic, but, you know, be aware of what type of biases are and use that knowledge to your advantage.
Kushal Saini Kakkar [00:28:40]:
There's so much I think that we could really get more into depth into, but because of the constraints of time, I'm going to ask you perhaps one last question, which is, if you had to do it all over again, what would you do differently?
Shruti Kapoor [00:28:53]:
I don't think I would do much of that differently. Right. And I think it's partially because you learn through that journey and you come out of it whichever way. I think the one thing that I would probably have done much more of and done much sooner of is connecting with a lot more other founders who are going through the journey for two reasons. One is, you know, of course, you can get the tactical advice and commiserations, but I think it also gives you a sense of understanding that, like, you know, every time you're failing or you're feeling down, like you're not the only person making a mistake. Right. And I think just having that encouragement is important. I think very often we kind of tend to close ourselves into our own room and say, you know what, I'm just so busy, I need to do the most I can.
Shruti Kapoor [00:29:48]:
But it's spinning wheels. It's not necessarily making progress. And I think if you spend that same amount of time in speaking to other people, and sometimes it's founder, sometimes it's just could be like a person who has experience in a particular function that you're trying to set up or whatever, you're likely to make much more progress. But what it requires for you to be able to do is to get vulnerable in front of people. And that's not, you know, that's not always a skill that we learn, especially after spending, like, a lot of time in the corporate world, pretending to be experts in everything and know what we are doing.
Kushal Saini Kakkar [00:30:26]:
Yeah, I think that's very powerful, Shruti. I think the ability and really the recognition that we're still human beings at the end of the day, no matter what our roles at work may be, we all need connection. We all need to be understood. And it helps to kind of be in the same boat as others, right. Who are sort of in the same situation to share notes or, you know, just for therapy in some sort of way. So I think, and I think that's not just for founders and entrepreneurs. I think that's solid advice for people. I think across different roles and different walks of life to really find their people.
Kushal Saini Kakkar [00:30:59]:
And I think in your case, to not just, you know, clearly you take out time and space to do that for so many other founders and folks who are also on similar journeys like you.
Shruti Kapoor [00:31:08]:
Right.
Kushal Saini Kakkar [00:31:09]:
So I think kudos for doing that as well. Shruti, it's been so great having you on this show. I really appreciate your time. Thank you so much. Thank you for listening to The Business OS. If you're looking for more resources on how to navigate growth, please go to justcall.io/thebusinessos. And don't forget, the journey is easier when you have a business osite.