Founder's Story - The Secret Struggle of Female Founders No One Wants to Admit | Ep 265 with Pavitra Anakru Founder of DealMagik

Episode Date: October 1, 2025

Pavitra describes commuting from New Jersey to New York before remote work existed, holding client meetings while deciding whether to miss a school play, and starting her first company in 2008 when Wall Street was on fire. She didn’t set out to be a CEO; clients from a collapsing firm pulled her into entrepreneurship, and a former CFO wrote the first check. Years later, COVID grounded her flights and exposed how fragile main street really was. A talk with her hairdresser—a friend and mother in her son’s circle—revealed the gap: local merchants were juggling siloed tools while big-box stores thrived on integrated tech. DealMagik was her answer: unify the messy stack and give mom-and-pop shops enterprise-grade capabilities without enterprise-grade pain. Key Discussion:Pavitra reframes “mom-guilt” as an incomplete story: presence matters, but so does modeling problem-solving at home. Her son, now a PhD student, grew up in the spillover of dinner-table debriefs about customers, product choices, and resilience; that, she says, was its own kind of presence. She walks through the real leap from employee to owner: writing every check yourself, discovering that scaling requires constant storytelling and sales, and learning that credibility in SMB land is won delivery by delivery, not pitch by pitch. As an immigrant founder, English wasn’t her first language, and she names the cultural and linguistic adjustments that fed years of self-doubt. The antidote was curiosity—the habit of asking how trades settle on Wall Street and, later, how salons, florists, and restaurants actually run their days. Curiosity led to competence; competence quieted the doubt. On AI, she’s optimistic: technology will change jobs, shorten the week, and rewire work, but it will also open new doors if we choose to walk through them. For founders considering a leap, she offers a grounded rule: get to the basics of the problem, solve it in small circles, and let trust compound. Takeaways:Ambition and family aren’t opposites when you bring your learning home. The difference between corporate and founder life is owning every line item and every outcome. Local business tech doesn’t fail for lack of tools; it fails for lack of integration and trust. Curiosity is a founder’s renewable energy; self-doubt loses to evidence. The future of work will be different not just in tools but in tempo—and platforms like DealMagik show how that future can reach the corner shop as surely as the Fortune 500. Closing Thoughts:Pavitra’s story isn’t a victory lap; it’s a field manual. She built through crisis twice, turned guilt into grit, and is now arming small businesses with the rails they lacked when the world shut down. If you want to see what practical optimism looks like, watch where DealMagik shows up next—and who it keeps in business. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

So Pavitra, I know you have a very unique story. What was this journey for you? Were there any sacrifices that maybe people wouldn't even know you had to make? I started my entrepreneurship in 2008. I was an accidental entrepreneur, my very first company. So I wasn't even ready to start the journey. Travel component itself is more than two hours of my day. So you can imagine juggling many things as a young mother

and as a young entrepreneur, it was not the easiest journey that I had to go through. Most people never talk about that. They always talk about the exit and success. They don't really talk about the things that really stick with you. So Pavitra, I know you have a very unique story, and I can't wait to get more into that. but something that we've noticed with other founders and CEOs who are women in the past that are also successful like yourself, they've given us some of the sacrifices that they've had to make, especially when it comes to some family type sacrifices. And I always think it's very inspirational for other women who might be thinking about that they want to be entrepreneurs or they want to continue in business,

but they're unsure of what type of sacrifices will they have to make. So can you walk me through in your life? What was this journey for you? And were there any sacrifices that maybe people wouldn't even know you had to make? Great question. And I can give you very good examples from my own journey. I started my entrepreneurship in 2008 right after the financial momentum. So you can imagine that being, especially my company being a Wall Street company,

I was right in the middle of the storm. And that's when I started. I was an accidental entrepreneur, my very first company. I just got thrusting to being an entrepreneur. So I wasn't even ready to start the journey. I did not even know what would come along my way. So having said that, I also want to say that I live in a place where my commute to workplace and all my customers are in New Jersey, New York, and I commute from New Jersey,

the travel component itself is more than two hours of my day. And this is at a time where remote work was not an option. So you can imagine juggling many things as a young mother and as a young entrepreneur, it was not the easiest journey that I had to go through. So that itself presents a lot of challenges and a lot of sacrifices at every step of the way. can I be part of my son's play and can I give up this meeting and go there and be part of a play that he's at? Those are decisions that you will have to make and those are the sacrifices. There is a game that is very important to him and can I be there at the right time and cheer him along the way.

So those are the things that you have to really make. a decision and at the same time we have uh sorry i'm sorry i just can i pause yeah of course i'm sorry i i am going on a tangent can i restart yeah i'm actually going to ask you a follow-up because it's great it's been great so far okay so apologies okay no no you so i'm going to ask you i'm going to ask you a question though and then we can continue because it's great so far okay i'm i'm glad you bring this up and it reminds me of two guests as actually a man and then a woman that we had two separate guests that told us about this sacrifice was something that stayed with them that guilt that even no matter how much money they made how much they sold their company for

they were always guilty about missing out on recitals or school things from the children i'm glad you bring up most people never talk about that they always talk about the egg exit and success they don't really talk about the things that really stick with you so tell me what as you become more successful in your journey do you have to still do you still feel guilty about these things or have you had to accept like this is how it is to be an entrepreneur yeah um that's a very insightful question and i looking back i feel that um i was not a very very insightful question and i was not a very correct in feeling so guilty about every aspect of life you know you know not being there and not being the cheerleader for your child every step of the way may make you feel like you're doing

something really bad as a mother but looking out for my own career my own company and also bringing that fighter instinct and problem solving instinct back home and discussing all of that with my son enriched him in a completely different way and when I look back he is now a PhD student but when I look back I do feel that I did the right thing

when you know we bring not just our presence we bring our everything the things that we learn the things that shape us we bring that back home too so I think that we have

have to always look at what we are doing and what value we are bringing back from what we are doing and we have our options, not as a binary choice of, am I doing the right thing, I'm being a good mother, a good employer, good cheerleader for my son. So that's not the only thing you think about. It's the entire value system. I like that. Yeah, it's not one thing or the other. Life is more complex and sometimes what you do now will really set you and your kids and your family up for success later on and i think they understand that like you're saying i think i think that i mean phd student our phd graduate i'm thinking he's doing pretty well and i don't think he would blame you for anything uh let's talk about your journey though so you were in this industry 2008 what a time to

be in business right like think we've heard like the greatest companies start is during these his economic crisis. And then you transition to a whole new industry solving a totally different problem. How did that come out for you? So I am a technologist. My career has always been in technology solving problems for any kind of applications where technology can be a solution, which is, you know, everything under the sun at this point in time. So I started off my career at a commodity brokerage and I learned and I grew along the way

and I learned about capital markets too and I had this opportunity to be the first employee of a broker dealer and I grew up to be the global head of their technology. And just before for 2008 there were some issues with the company and like, like many other companies in the Wall Street, things were going down. And a lot of the people that I used to support different trading desks started moving to different brokerage companies on the street. And they all started calling me to come and join them and help them develop the same kind of technology solutions that I had developed.

And that's when I realized, okay, maybe I cannot join a cherry pick who I should join. instead, why not start a company and just, you know, help everybody who has an interest in my company. And that was the decision day for me. And one day I was an employee and the next day I was an entrepreneur. And the CFO that I, of my previous company, he actually gave me the seed fund and said, yeah, go do it. And he had that level of trust in me because of all the accomplishments and the, and things that I had created and he believed in me. And that's how I got started.

And we grew to be a company that supports global trade capture processing and regulatory reporting for various broker dealers, both here and abroad. Was there what point? And that's a great story, though. And I think a lot of people go through the corporate to business. I think a lot of people underestimate what their ability is and how they could do it on their own as a business, right? It's like, okay, you've done this for this one company. You've actually proven there is a problem.

You've proven the solution. You've proven it. I don't think a lot of people know that, okay, I can transition now. Instead of just being this one employee, I can now do this in business because I've done it, proven it. And I can now help many businesses. So what was the learning for you when you transition into business, maybe something that you would have never thought that, oh, wow, like there, even though you might be doing the same thing, but it's so different when you're an employee versus when you're in business. What was something that came up that you're like, oh my gosh, I wish I had known this. Well, the first answer is you have to write check for everything on your own, starting from buying a business.

laptop for yourself and your employees, every single thing out there you have to finance and you have to know how much it costs, what is the return, is it a good investment to make? So when you are a corporate, there are tons of things that come to you easily. But when you're starting off on your own, software licenses, every single step of the way, you have to know what it costs, is it a good decision to make and is it a make or break decision. So that, in and of itself, was a big learning for me and going from a protected world to, you know, wild, wild west, if you will. So you had to learn everything on the go and adapt as you progressed. The second thing that I feel is we kind of overestimate our,

at least I did, overestimate our ability to scale. And ability to scale initially, in my case looked really, really good, but then it becomes a, you know, a situation where you have to constantly network and constantly put yourself out there, promote yourself and your company and what your offerings are. I did not know going in, being an accidental entrepreneur. I did not know the salesman part of it that I had to learn. So that, well, I did learn and I keep learning every day, but that in and of itself was a big revelation for me, what it takes to be known and make your company and products known to people. It reminds me of the book, The E-Mith. I don't know if you've ever read this book. It's quite an older one. And it talks about the baker who

wants to bake but doesn't realize she needs to be the accountant, the HR, you know, that you have to do, you realize you have to do everything. Like, whatever you are most passionate about doing might be the thing you actually do the least when you're in business. And I think that could discourage some people. But so it sounds like you did see some success and you had or you had a lot of success. What was the transition when you when you either got out of that, left that changed and now went to the new company. So I really am not fully out of it. I'm actually helping out whenever I need.

And we still run, my husband kind of join me and we both ran the first company together. And he's actually managing our first company at this point. And the transition time was actually during COVID. I used to travel a lot before COVID. I used to visit our clients in London and of course New York was an everyday thing and that travel completely got shut off during COVID

and I had extra time on my hand and at the same time I was seeing what's happening in our local market and the people that we used to frequent for our, you know, hair cut or food or any kind of local merchant right they were all shutting down or they were all very very unsure of what their future would be and that was an eye-opening event for us and especially for me and I started talking to one of

my hairdresser she happened to be my son's friend's mother too so I knew her personally and we were talking about what things were how things were affecting and what challenges she faces and that when we realized there is a big chasm, if you will, a big gap between everyday local merchants, pop and mom's stores and big box stores. And the technology is the solution to bridge that gap. So and the people in the local merchants, they do have technology. Everything is so siloed. They have to juggle with many things. They are not necessarily the, that's not their forte, right? And they have to literally, literally learn everything. And that was when I realized, hey, I have a, being a technologist, I have a solution. I can create something that will bridge the gap. And that's when

the magic was born and we started prototyping it and showing it to a few people and they loved it. and we built on top of it and it's now a viable product. Yeah, it's, it is quite fascinating how many times these local type businesses don't really understand or use any technology. They don't do any marketing. They assume if you open up a store or open up something that people would just show up and you and I realize like it probably won't happen. And if you're not leveraging technology, your business could go under.

neighbor is leveraging technology, right? And how much, especially now AI, how much cost savings and everything that you can do nowadays. What was the, or was there anyone who you talk to about this? I mean, I definitely understand the problem. I used to have a local business. So I can relate to a, of this solution being something of benefit. Did you find, though, were there people that didn't believe in it and was that discouraging to you or did you find getting your first 100 clients was just super easy because you were dialed into who those were definitely not the latter there is a lot of speculation and a lot of skepticism from the people from the merchant community for all the right reasons and it's a challenge

to actually go in and explain and show them what you have and how it works and deliver on your promises and make sure that you build up the trust every step of the way. So it's not like I walk in and everybody opens the door and next day you have 100 people fully onboard it. No, that's not how it is. You have to win them over by actually delivering what you're promising. And that is a bigger challenge than what I have seen on. Wall Street. So, but yeah, it's a, it's a very fulfilling thing to solve that problem.

I mean, you, you know, it's like the backbone of the of the country are these, what they would call small business, which I know some of them are considerably larger than what I would define, but I know it's like over 50% of jobs are in small businesses. And like you said, so many of them, unfortunately, never even recovered. If you go back to your younger self, and you think about what your younger self wanted to do when she grew up or where she thought she would be at your age right now, how do you think your younger self would feel about the journey you've had? Okay, that's an interesting question. Well, if I look back, I always feel that I had, if I give myself credit for one thing, I've always been very curious about things and I

always prioritized learning. It can be of any type of learning. It could be science. It could be anything about how people do their business. I've always been curious about learning. And that helped me obviously to know the fundamentals of how we do our work, but also when I went on Wall Street, I was curious about how do these people put a trade through, what does it take, what's behind it, being inquisitive. And again, the same thing, when I came to the mainstream, how does this work? How do they know which point of system to use? How do they make people come through the door and how do they market?

Being inquisitive about everything and curious about everything and wanting to learn has been my biggest strength. My biggest weakness has been self-doubt. And that makes me always doubt myself, will I be the person who can do these things? I am I qualified enough? I am I capable enough. And I had a lot of self-doubt all along my life, how through my life. And looking back right now, I would tell my younger self, don't be so hard on yourself.

Everybody can do it. You just have to set the focus. And that's what I would tell my younger self. believe in yourself keep the focus on you said a few things that i have lived myself by being inquisitive always learning it's really incredible it's something it's just like people will say you know the one of the most important things you can do is just listening right and it's like something so easy yet so many people struggle i think with that uh you know the the desire to want to learn new things or or seek to understand things, which I can totally relate to that.

You also talked about self-doubt. Was there something that happened in your life that do you think has caused that? And are you working or how are you working to maybe change the self-doubt? It's not something that happened in my life, I would say, to be honest. I am an immigrant. I migrated from India and English has not been my first language and even though I was very fluent with it, there is a lot of difference in both culturally and accent and usage of words or what have you, right? So that in and of itself kind of holds you back. How do you assimilate and make sure that what you're saying is hurt?

the way it was intended to be heard. So that kind of creates a self-doubt in and of itself. Am I saying the right thing? Am I presenting myself in the right way? That's always there. That's a learning curve. And at the same time, you grew up with among certain peers and you're totally thrown into a completely different environment.

And I have not had an opportunity to weigh myself against everybody else to know where I stand. So that kind of creates a lot of uncertainty and that translates to self-doubt. And that's what I had to overcome. And now I do feel that, you know, there are challenges that I faced or on the flip side, my peers over here also had a lot of challenges that they faced. It's not what the challenge is because of our in the backgrounds, we will all have. challenges. It's our attitude that tells us I can overcome this and we have to work on that

and, you know, work on being a problem solver and I always look at it as, okay, let's get down to the basics of what this problem is and try to solve it rather than trying to beating myself down or coming up with excuses. And that has helped me. Well, I mean, I don't know any other language fluently and i couldn't imagine going to another country and i where i i wasn't it wasn't my first language and then learning the language doing business so you know hats off to you for being able to do that and i would have i have self-doubt already and it was my first language so i you know i could only imagine i was just in bengalore by the way i had a very incredible experience there And I was fascinated by how much growth technology.

There were so many people that were, you know, Indian descent in the U.S. that have now going back to India to do investments in Bangalore and technology. It's really amazing, like what's happening around the world. It's super exciting. Last question for you is this, since you are a technologist, obviously everyone's talking about AI, machine learning. I don't think anyone's even talking about quantum computing yet, which, you know, there's so many. I was just reading about this company doing humanoids,

doing humanoids, which is a whole other thing I'm excited about. What excites you or scares you, either one, about technology in the near future? I wouldn't be scared of technology for sure. and what excites me is all the opportunity in presence. Yes, there will be, along the way there will be people who will have to think about how they engage themselves, including programmers like me, they're finding it hard to find the job, but good ones always do.

But there is also a lot of opportunity that it opens up. And I'm hopeful, I don't see it right away, but I'm hopeful that it is something that will open door for betterment of humanity and for everybody to work differently. And it may not be the same way that we were doing, you know, the job 9 to 5, the assembly line, Ford kind of introduced the 9 to 5 days a week kind of culture. We all kind of went with that.

And this is a paradigm shifting thing that is happening. It will change our lives. And I do think that it is. going to change our lives for better. And what it is, I don't have a crystal ball, but I am hopeful. Well, I've been doing a lot of vibe coding and I don't know anything about coding, but I've been able to code things. It's amazing. And I love that you are very positive and I love your positivity. I would, I would be happy if we had the 10 to 12, like 10 a.m. to 12 p.m. and that's my whole day and I get everything done. That sounds way better for me than a 9 to 5 or 9 to 4.

two days a week, you know, a maximum. But if people want to get in touch with you, they want to find out more information, they want to test out your platform. And by the way, also, is your platform only in certain cities? Can you share a little bit more? So our dealmagic.com is the magic spelled with M-A-G-I-K instead of M-A-G-I-C. People can go on dealmagic.com and find out more about us. And we are live throughout the United States.

We are not restricting to any region or anything. So we support all kinds of businesses, restaurants, florists, candle bakers, and salons, spas, and even experiences. Anybody who has something to sell online can be on Deal Magic platform. They can create a promotion or upsell with their complete product catalog. We support shipping management, delivery management pick up and buy online redeeming store and all kinds of things of the back of it so it's for everybody all kinds of businesses well pavitra thank you so much for all

that you do to help these businesses helping them thrive helping them hopefully continue on because we know how hard it can be and also i you know i'm very inspired by our conversation today I learned a lot and thank you so much for joining us on Founder's Story. Thank you so much for having me.