What COVID Exposed—and DealMagik Fixed—for Local Businesses | Ep 265 with Pavitra Anakru Founder of DealMagik

Summary

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Episode Summary: "What COVID Exposed—and DealMagik Fixed—for Local Businesses"

Podcast: Founder's Story, IBH Media
Episode: 265
Guest: Pavitra Anakru, Founder of DealMagik
Date: October 1, 2025

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Main Theme & Purpose

This episode explores the entrepreneurial journey of Pavitra Anakru, from being an “accidental entrepreneur” on Wall Street during the 2008 financial crisis to founding DealMagik, a tech platform designed to empower local businesses. The host and Pavitra discuss sacrifices faced by entrepreneurs (especially mothers and immigrants), resilience through crises such as COVID-19, and how technology can bridge critical gaps for local merchants. The conversation is raw and honest—centering on what is rarely discussed about entrepreneurship: guilt, self-doubt, adaptation, and legacy.

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Key Discussion Points & Insights

1. The Personal Sacrifices of Entrepreneurship

• Balancing Motherhood and Startups
  • Pavitra details the challenges of commuting over two hours daily from New Jersey to New York, all while raising a young child and building a business—at a time when remote work was not an option.
    • “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 is at? Those are the decisions that you will have to make, and those are the sacrifices.” (04:14, Pavitra)
• Guilt & Reflection
  • She reflects on the emotional labor and guilt of missed family moments, but also on how her entrepreneurial traits influenced her son positively, noting his current success as a PhD student.
    • “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... discussing all of that with my son enriched him in a completely different way.” (06:08, Pavitra)

2. Becoming an Accidental Entrepreneur

• Thrust into Entrepreneurship during Financial Turmoil

  • Pavitra entered entrepreneurship unexpectedly when her Wall Street employer faced struggles. Her reputation prompted multiple former clients to reach out, leading her to start her own company—supported by seed funding from her ex-employer’s CFO.
    • “One day I was an employee and the next day I was an entrepreneur... The CFO of my previous company, he actually gave me the seed fund and said, yeah, go do it.” (10:31, Pavitra)

• Lessons from Transitioning Corporate to Business Owner

  • Key differences between being an employee and a founder: budgeting every expense from laptops to software, understanding the true costs and ROI of every business decision, and learning to “sell” herself and her company—skills she had underestimated.
    • “Going from a protected world to wild wide west... you had to learn everything on the go and adapt as you progressed.” (12:43, Pavitra)
    • “I did not know going in ... the salesman part of it that I had to learn.” (13:31, Pavitra)

3. The Spark for DealMagik—COVID-19’s Local Business Crisis

• Pandemic Realities

  • COVID-19 halted her global travel and offered an unexpected pause, which drew her attention to the struggles of neighborhood merchants (“mom & pop” shops) facing closure without digital tools.
    • “Local merchants... technology is the solution to bridge that gap... And that was an eye-opening event for us and especially for me.” (15:06, Pavitra)

• Creating & Launching DealMagik

  • Motivated by the glaring technology gap, Pavitra started prototyping what became the DealMagik platform—a centralized solution for promotions, online sales, and back-office management for local businesses.
    • “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.” (16:39, Pavitra)

4. Addressing Merchant Skepticism

• The Trust Gap
  • Convincing local merchants, many of whom are skeptical of new tech solutions (“for all the right reasons”), became a harder challenge than working with Wall Street clients.
    • “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.” (18:28, Pavitra)

5. On Curiosity, Learning, and Self-Doubt

• A Lifelong Student’s Advantage

  • Pavitra credits her inquisitive nature for success, always striving to understand how businesses function at every level.
    • “If I give myself credit for one thing, I've always been very curious about things and I always prioritized learning.” (19:37, Pavitra)

• Immigrant Experience and Confidence

  • She shares how being an immigrant and non-native English speaker contributed to self-doubt, especially in adapting culturally and professionally.
    • “English has not been my first language... So that in and of itself kind of holds you back. How do you assimilate and make sure that what you're saying is heard the way it was intended to be heard?” (22:05, Pavitra)
  • On overcoming: “It’s not what the challenge is. Because of our backgrounds, we will all have challenges. It’s our attitude that tells us I can overcome this…” (23:20, Pavitra)

6. Technology’s Transformative Future

• AI and Beyond: Hope, Not Fear
  • Pavitra expresses optimism about the paradigm shift AI and new technologies are bringing, seeing these changes as opening opportunities for all—even if it means jobs look different and old routines change.
    • “I am hopeful that it is something that will open door for betterment of humanity... It will change our lives and I do think that it is going to change our lives for better.” (25:41, Pavitra)

7. DealMagik Platform: Nationwide, Inclusive, Practical

• Who Can Use DealMagik?
  • Available across the U.S., DealMagik supports any retail, service, or experience-based business.
    • “We are live throughout the United States... They can create a promotion or upsell with their complete product catalog. We support shipping management, delivery management, pickup and buy online redeeming store and all kinds of things off the back of it.” (27:06, Pavitra)

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Notable Quotes & Memorable Moments

• On Maternal Sacrifice:
  “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... discussing all of that with my son enriched him in a completely different way.” (06:08, Pavitra)

• On The Entrepreneurial Learning Curve:
  “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?” (12:10, Pavitra)

• On Building Trust with Local Merchants:
  “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.” (18:28, Pavitra)

• On Battling Self-Doubt (as an immigrant and entrepreneur):
  “My biggest weakness has been self doubt... looking back right now, I would tell my younger self, don't be so hard on yourself. Everybody can do it.” (20:23, Pavitra)

• On AI and the Future:
  “It is a paradigm shifting thing that is happening... 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.” (25:41, Pavitra)

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Key Timestamps for Important Segments

• 01:16 — Pavitra’s journey into entrepreneurship and sacrifices as a mother and founder
• 05:54 — Reflection on guilt, motherhood, and success
• 09:08 — How Pavitra became an accidental entrepreneur during the 2008 crisis
• 11:58 — Lessons from moving from employee to founder: budgeting, sales, and scaling
• 14:26 — The COVID-19 pivot: identifying local business struggles that led to DealMagik
• 16:50 — Prototyping and launching DealMagik for main street merchants
• 17:54 — The challenge of earning trust from skeptical local business owners
• 19:25 — The role of curiosity and learning in entrepreneurial success
• 21:54 — Overcoming self-doubt as an immigrant founder
• 25:12 — Thoughts on AI, technological change, and work-life paradigms
• 27:01 — DealMagik’s availability and capabilities for U.S. businesses

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For More Information

• DealMagik: dealmagik.com (MAGIK spelled with a "K" at the end)
  • Platform available nationwide for all business types (retail, food, experience, services, etc.)

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Tone and Takeaways

The episode is honest, thoughtful, and encouraging, especially for emerging entrepreneurs, women balancing family, and immigrants. Pavitra’s journey embodies resilience and adaptability—themes central to “Founder’s Story.” She navigates both the vulnerabilities and triumphs of entrepreneurship, leaving listeners inspired to be curious, adaptable, and hopeful in the face of continual change.

Transcript

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[Interviewer]

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?

[Pavitra, Entrepreneur and Technologist]

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.

[Interviewer]

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, that 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, what was this journey for you and were there Any sacrifices that maybe people wouldn't even know you had to make?

[Pavitra, Entrepreneur and Technologist]

Great question. And I can give you very good examples from my own journey. I started my entrepreneurship in 2008 right after this financial mental. 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 thrust into 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 York and I commute from New Jersey. The travel component itself is more than two hours of my day.

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[Pavitra, Entrepreneur and Technologist]

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, 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 is at? Those are the 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. Sorry, I'm sorry, I just. Can I pause?

[Interviewer]

Yeah, of course.

[Pavitra, Entrepreneur and Technologist]

I'm sorry, I. I am going on a tangent. Can I restart?

[Interviewer]

Yeah. I'm actually going to ask you a follow up because it's great. It's been great so far.

[Pavitra, Entrepreneur and Technologist]

Okay, so apologies. Okay.

[Interviewer]

No, no. So I'm gonna ask you if. I'm gonna 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. It's 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 their children. I'm glad you bring that up. 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 tell me what, as you become more successful in your journey, did 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?

[Pavitra, Entrepreneur and Technologist]

Yeah, that's a very insightful question. And I, looking back, I feel that I was not 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. And 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 to always look at what we are doing and what value we are bringing back from what we are doing and weigh our options. Not as a binary choice of am I doing the right thing? Am I being a good mother, a good employee, a good cheerleader for my son? So that's not the only thing you think about. It's the entire value system.

[Interviewer]

I like that. Yeah. It's not one thing or the other.

[Pavitra, Entrepreneur and Technologist]

It.

[Interviewer]

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 Ph.D. student, our Ph.D. graduate, I think he's doing pretty well and I don't think he would blame you for anything. 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 during these economic crisis and then you transition to a whole new industry solving a totally different problem. How did that come out for you?

[Pavitra, Entrepreneur and Technologist]

So I am a technologist. My career has always been in technology. Sol.

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[Pavitra, Entrepreneur and Technologist]

Applications based 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 head, global head of their technology. And just before 2008 there were some issues with the company. And 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 cherry pick who I should join and instead why not start a company and just 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 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 things that I had, 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.

[Interviewer]

Was there a 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. And 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, 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. I wish I had known this.

[Pavitra, Entrepreneur and Technologist]

Well, the first answer is you have to write check for everything on your own, starting from buying a 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 are starting off on your own software licenses, every single, every 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 wild wide west, if you feel 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 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.

[Interviewer]

It reminds me of the book the E. Myth. 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 that 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.

[Pavitra, Entrepreneur and Technologist]

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 joined me and we both run. 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, haircut or food or any kind of local merchant. Right. They were all shutting down or they are. 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 talk about what things were, how things were affecting and what challenges she faces. And that's when we realized there is a big chasm, if you will, a big gap between everyday local merchants, pop and mom stores and big box stores. And the technology is the solution to bridge that gap. So and the people in the, 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 Dealmagic 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.

[Interviewer]

Yeah. 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. If your neighbor is leveraging technology. Right. And, and how much, especially now AI how 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 could, I can relate to 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, you know, getting your first 100 clients whereas was just super easy because you were dialed into who those were?

[Pavitra, Entrepreneur and Technologist]

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 onboarded. No, that's not how it is. You have to win them over with act by actually delivering what you're promising. And that is a bigger challenge than what I have seen on Wall Street. But yeah, it's a very fulfilling thing to solve that problem.

[Interviewer]

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, I know it's like over 50% of jobs are, 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, 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?

[Pavitra, Entrepreneur and Technologist]

Okay, that's an interesting question. Well, if I look back, I always feel that I had. What 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 and watched it, 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 main street. 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? Am I qualified enough? Am I capable enough? And I had a lot of self doubt all along my life, all 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 you, you and that's what I would tell my younger self. Make believe in yourself, keep the focus on you.

[Interviewer]

Said a few things that I have lived myself by being inquisitive, always learning. It's really incredible something. It's just like people will say one of the most important things you can do is just listening. It's something so easy, yet so many people struggle I think with that, you know, the desire to want to learn new things or, or seek to understand things which I can totally relate to that. You, 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, or how are you working to maybe change the self doubt?

[Pavitra, Entrepreneur and Technologist]

It's not something that happened in my life I would say to be honest, I, I am an immigrant, I, I migrated from India and English has not been my first language. And even though I was very fluent with it, this, there is a lot of difference in both culturally and accent and usage of words or what, 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 heard 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 grow up among certain peers and you are 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, now I do feel that, you know, there are challenges that I faced. And 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 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 try to beating myself down or coming up with excuses. And that has helped me.

[Interviewer]

Well, I mean I don't know any other language fluently and I couldn't imagine going to another country and I, where 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 can only imagine. I was just in Bangalore, 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, in Indian descent in the US 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 and 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 there's so many. I was just reading about this company doing humanoid. Doing humanoids, which is whole nother thing I'm excited about. What excites you or scares you either one about technology. In the near future.

[Pavitra, Entrepreneur and Technologist]

I wouldn't be scared of technology for sure. And what excites me is all the opportunity it presents. Yes, there will be along the way there'll 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 nine to five, the assembly line. Ford kind of introduced the nine to five or five 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.

[Interviewer]

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 be happy if we had a 10 to 12, like 10am to 12pm and that's my whole day and I get everything done. That sounds way better for me than a nine to five or nine to four, 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.

[Pavitra, Entrepreneur and Technologist]

So our dealmagic.com the magic spelled with M A G I k instead of magic 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 makers in the salon, spas and even experiences. Anybody who has something to sell online can be on dealmagic platform. They can create a promotion or upsell with their complete product catalog. We support shipping management, delivery management, pickup and buy online redeeming store and all kinds of things off the back of it. So it's for everybody, all kinds of businesses.

[Interviewer]

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'm very inspired by our conversation today. I learned a lot and thank you so much for joining us on Founder Story.

[Pavitra, Entrepreneur and Technologist]

Thank you so much for having me.

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