Vikram Shekhawat On Selling A Company To Blackboard And Now Building An AI Platform To Offer Companies A Suite Of Tools To Streamline Content Creation And Business Workflows

Entrepreneurship is a rollercoaster ride, and few have navigated its twists and turns with as much grit and adaptability as Vikram Shekhawat. His journey is a testament to resilience, learning, and an unwavering vision when building, scaling, and exiting his many startups.

Vikram’s latest venture, ModalX, has attracted funding from top-tier investors like Plug and Play, Panache Ventures, Combine Venture Builders, and Thin Air Labs.

In this episode, you will learn:

• Vikram’s delayed entry into startups underscores the importance of surrounding yourself with ambitious, like-minded people.
• His first startup, CrushAider, grew to 600,000 users in six months but failed to secure funding due to a lack of future planning and market positioning.
• Lessons from his failed startup helped him refine his approach, leading to a successful exit with Bschool.
• Vikram’s stint in large enterprises provided valuable lessons on scaling, structuring teams, and managing B2B2C operations.
• Bringing in industry veterans without startup agility hindered Pariksha’s growth, teaching him the importance of adaptable hires.
• Pariksha’s shift from institutional to direct consumer targeting led to rapid scaling and an exit when the company was valued at $18M.
• ModalX aims to revolutionize AI adoption for small businesses, making it as seamless as a conversation with a friend.

 

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About Vikram Shekhawat:

Vikram Shekhawat, based in Toronto, ON, CA, is currently a Co-Founder and CEO at ModalX. He brings experience from previous roles at Stealth Startup, Bschool, CrushAider, Pariksha, Times Internet and HDFC Bank.

Vikram Shekhawat holds a Symbiosis Institute of Business Management, Pune. He is a BBC-featured entrepreneur, adept at opportunity scouting, problem solving, value selling, winning Mindshare and mobilising team potential towards innovation and value creation.

He brings over 14 years of startup and corporate experience having worked in the field of Generative Artificial Intelligence, Banking, Internet, Edtech and software sales.

Vikram has functional expertise in Project Management, Strategic Marketing, Business Planning, Early-Stage Startups, Channel Engagement, Problem Solving, Financial Planning & Analysis, Stake Holder Management, Key Performance Indicators, Business Relationship Management, Go-to-Market Strategy, Budgeting & Forecasting, Product Innovation, Corporate Partnerships, and Design Thinking.

Connect with Vikram Shekhawat:

• LinkedIn
• Crunchbase
• RocketReach
• TheOrg

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty, hello everyone, and welcome to the DealMaker Show. Today, we have an amazing guest joining us. He’s done it a couple of times, and it’s truly remarkable how many things he’s accomplished—I was honestly losing track of everything he’s done! In today’s session, we’re going to talk about how he built, financed, scaled, and even exited his last company. Now, he’s diving into the incredible world of AI, working on some really fascinating stuff. So, we’re going to dive deep into all of that.

Alejandro Cremades: But without further ado, let’s welcome our guest today—Vikram Shekhawat. Welcome to the show!

Vikram Shekhawat: Thanks for having me on the show, Alejandro.

Alejandro Cremades: So, originally born in the Punjab area of India—walk us through memory lane. How was life growing up for you?

Vikram Shekhawat: Life was good—life was fun. I was born into an army family, so my father used to get posted to a different location every three years. I had the privilege of moving with him, which kind of set me up for a bunch of different things that a lot of people don’t usually experience—like moving into a new circle, adapting, building new relationships, and figuring out what works and what doesn’t. And you’re trying to do all of that while you’re still a kid, trying to find focus amid all the chaos around you.

Vikram Shekhawat: So, I started with that. I did most of my schooling in Army School. Then, I completed my graduation with a BBA degree and went on to do my master’s from one of the best colleges India had to offer—Symbiosis.

Alejandro Cremades: One thing worth pointing out about your childhood is that you weren’t really surrounded by a lot of ambitious people, which, I think, kind of delayed the entrepreneurial drive kicking in. So, tell us more about that.

Vikram Shekhawat: Yeah, I think that’s one of the most important things. If you want to become an entrepreneur, if that’s something you aspire to do, you should ideally start pretty early. I think I started a bit late—I launched my first company when I was about 20.

Vikram Shekhawat: I believe I should’ve done it even sooner. One of the key reasons I didn’t start earlier was that I was surrounded by people who just wanted to have fun—which is typically how college kids or teenagers behave at that age.

Vikram Shekhawat: But if you look at the success stories of people who made it big, a lot of them had a significant hustle going on in their early years.

Vikram Shekhawat: That hustle came from having the right kind of people in their circle. You need people who are equally or more ambitious than you. That sets the tone. It also helps in forming the initial team needed to build a business. I don’t think individuals alone build great companies—it’s a team that comes together.

Vikram Shekhawat: If you’re surrounded by like-minded, ambitious people who want to change the world, that’s when you can make a real impact fairly quickly. In my case, I didn’t have that kind of company around me initially.

Vikram Shekhawat: I only found that kind of circle when I was doing my master’s, and that’s the reason why I built my first company when I was about 20.

Alejandro Cremades: So let’s talk about that—your first company, Crusader. How did that come about? You didn’t really have the drive yet, but what would you say pushed you to say, “Hey, I think I’m going to test out this venture thing”?

Vikram Shekhawat: It came from a personal problem. I was very shy until around the time I graduated. I had feelings for someone but wasn’t able to express them.

Vikram Shekhawat: Crusader was a dating platform that connected people with mutual crushes. My realization was that it wasn’t just my issue—it was probably something many teenagers my age dealt with. I wanted to create a platform that gave people anonymity when expressing their feelings.

Vikram Shekhawat: So, Crusader was a platform where, let’s say, someone had feelings for you—they could express it anonymously using the right set of tools. Not everyone is born Will Smith—so they wouldn’t necessarily know what to say or how to say it. That’s where Crusader would come in and help them with how to express their feelings.

Vikram Shekhawat: We found some interesting stats: on average, a guy has a crush on at least seven girls, and a girl typically has a crush on at least three guys. Crusader let users express their feelings anonymously, and the other person would receive a message or email saying someone had a crush on them.

Vikram Shekhawat: They’d be prompted to come onto the platform and indicate who they liked. If there was a match, we would connect them. This eliminated three major fears: fear of changing relationship dynamics, fear of embarrassment, and fear of rejection in front of others.

Vikram Shekhawat: That’s what Crusader did.

Alejandro Cremades: So with Crusader, it seems like you weren’t very well-prepared for meeting with investors, at least at the beginning.

Vikram Shekhawat: Yes, agreed. We scaled pretty fast. We got to about 600,000 users in around six months—back when the internet was still becoming a thing in India.

Alejandro Cremades: Wow.

Vikram Shekhawat: Even now, if you go on platforms like Facebook, you’ll still see 40,000 to 50,000 followers—purely organic. When that kind of success comes early, it messes with your head. You start getting a lot of attention and interest from people around you.

Vikram Shekhawat: That’s when we got significant interest from several VCs in India. In my head, I thought I knew what I was doing, but really, the only plan I had was how to acquire more users.

Vikram Shekhawat: They wanted to know what the future plan looked like—I had zero understanding of that. In my first VC meeting, instead of killing it, I probably failed to even put on a decent show.

Vikram Shekhawat: It was a solid learning experience. We later saw in 2014 and 2015, the likes of Bumble and Tinder becoming billion-dollar companies. We could’ve done that in 2009 when we were scaling so quickly.

Vikram Shekhawat: But due to a lack of preparedness, we messed up a couple of investor meetings. I was still in college, so I didn’t really pursue the idea much further. Server costs were a big pain point back then, so we ended up shelving the product. I thought I’d probably reignite it someday—but it didn’t happen.

Vikram Shekhawat: It still remains in the shadows.

Alejandro Cremades: So what happened after that? Bschool seemed to be the next stop.

Vikram Shekhawat: Yeah, Crusader taught me a valuable lesson: if you’re meeting VCs, you need to be prepared with everything—from your team to projections, to how your solution is better than others in the market. That’s when we introduced Bschool.co, a platform providing holistic information about business schools worldwide.

Vikram Shekhawat: Interestingly, the same investors I’d spoken to earlier came in as angel investors for Bschool. It scaled quickly. It was global in scope but locally relevant—helping people make rational decisions about which college to pursue.

Vikram Shekhawat: Eventually, the traction we were getting caught the attention of the Blackboard team. They reached out to us, and an acquisition took place.

Alejandro Cremades: Pretty amazing—getting the company acquired. What was it like going through that experience?

Vikram Shekhawat: It was very rewarding at the time. When you’re building a startup, you’re often taking a minimal salary because you’re the one putting in the initial money. Angel investment doesn’t really cover your salary.

Vikram Shekhawat: I was surviving on something like $100 per month. Back in India, that wasn’t terrible, but it was still a small amount by any standard.

Vikram Shekhawat: Doing that for eight months—covering expenses and facing all the challenges that come with limited funds—while continuing to put in the effort… it all pays off when you get acquired. That was the first real money I made, and it gave me solid belief in myself.

Vikram Shekhawat: It showed me that I had what it takes to be a decent entrepreneur—maybe not extremely successful yet, but someone who could pursue this path, face challenges, and build something valuable.

Alejandro Cremades: After Bschool, instead of jumping straight into another business, you did a bit of corporate hopping. What needed to happen for you to get comfortable again and go at it with Perishka? Because you were spending time in larger corporations, which isn’t really your thing.

Vikram Shekhawat: Yeah, great question. Initially, I worked with companies like Kotak Mahindra Bank, HDFC Bank, and Times Internet because my mentors advised me to get experience in the B2C space—and to understand how large enterprises operate. I needed to learn how these giant machines work—how they ensure different departments function seamlessly, how they scale across geographies, and how they understand and manage different markets.

Vikram Shekhawat: That was a valuable learning experience, and it initially made me inclined to work in those settings.

Vikram Shekhawat: There was also instant growth in these companies that kept me excited—I got three promotions at Kotak Mahindra and a couple at HDFC.

Vikram Shekhawat: And then I was like, okay, I’ve had enough of banking already—let me get back to the world of the internet. That’s when I joined Times Internet Limited. I worked with them for a while.

Alejandro Cremades: So then, what was the immediate next step for Pariksha? What do you think was the triggering point that made you say, “I want to do this again—I’m done with corporations”?

Vikram Shekhawat: For the same reason—beyond a certain point, large enterprises move very, very slowly. You might have ten different innovative ideas, but you can’t put them into execution. You have to run them through a long chain of command.

Vikram Shekhawat: That slows down the enthusiasm you’d have if you want to be an entrepreneur, rather than just an intrapreneur. I saw that happening, and I wasn’t enjoying it as much.

Vikram Shekhawat: I felt like I was letting my skills go to waste in a place where they probably wouldn’t be rewarded the way they should be. So I thought, why not go back to square one and build something for myself—something with more purpose, more motivation, and better stakes in the game? Something that could have a large-scale impact on the target market we wanted to serve. That led to the eventual founding of Pariksha, which I built along with three of my co-founders.

Vikram Shekhawat: So, Pariksha…

Alejandro Cremades: So then talk to us about how you met those co-founders, and what was that moment that led to “Alright, let’s do this thing”?

Vikram Shekhawat: I had already been investing in startups while I was working with HDFC and Times Internet. Pariksha was initially one of the companies I had invested in, and they were on a different path at the time.

Vikram Shekhawat: They were trying to build a solution focused on colleges, helping students prepare for campus placements. In 2018, we noticed that while we had a lot of customers, they weren’t paying us.

Vikram Shekhawat: We had many pending invoices and realized that most of these large institutions followed bureaucratic processes. They would use the service but not pay on time, and these payments would get stuck for up to a year.

Vikram Shekhawat: So, we decided to pivot. I was one of the initial investors and offered to help the team with sales—specifically, figuring out how to reach customers directly rather than going through institutions. We decided to change the model a bit.

Vikram Shekhawat: That’s when we discovered an exam happening in the state of Madhya Pradesh, which had around 1.1 million aspirants. We thought—why is no one going after this market?

Vikram Shekhawat: To our surprise, we realized this was a hyper-local market. You couldn’t scale or build a business here unless you had feet on the street and deeply understood each state individually.

Vikram Shekhawat: So, we decided to build a vernacular platform—catering to these markets in their preferred languages, going very local with the content. You can’t scale this kind of business by simply running ads on YouTube, Google, or Meta.

Vikram Shekhawat: You need to build local partnerships. I believed my skills could add a lot of value here, especially given my previous experiences.

Vikram Shekhawat: That’s when I officially came on as a co-founder. In 2018, along with the three other co-founders—whom I had initially met while judging a competition—we decided to join forces. We began scaling the business, brought in our first 100,000 customers, then reached a million. We raised about $3 million in funding and scaled the company to 120 employees across 18 different states and eight different languages.

Vikram Shekhawat: It was growing pretty fast. From 2018 to 2022, I was part of Pariksha, helping build and scale the company.

Vikram Shekhawat: And then, around 2022, I exited the company.

Alejandro Cremades: So, let’s talk about the exit, too. The transaction was rumored to be around $18 million. But as a founder, talk to us about the timing—when is the right moment to turn the page?

Vikram Shekhawat: In my case, I wasn’t entirely comfortable with the idea of an acquisition. I wanted to build something that would scale and become extremely big. At our peak, we were serving about 6 million users.

Vikram Shekhawat: My vision was to make the platform something that a billion people could eventually use. But that vision wasn’t necessarily shared by all my co-founders.

Vikram Shekhawat: In my mind, if we weren’t going to create that kind of impact, then it was better for the company to be led by the majority shareholders who believed in a particular approach. I didn’t want to be a roadblock.

Vikram Shekhawat: That difference in vision eventually led to my exit. There was a lot of consolidation happening in the education market in India at that time. I wouldn’t say my co-founders lacked vision—it’s just that, given the market dynamics, they felt being acquired and working under a larger umbrella would serve the purpose better.

Vikram Shekhawat: Personally, I believed we could’ve been the ones acquiring other companies. But that was just a difference in perspective.

Alejandro Cremades: So let’s talk about scale. With Pariksha, you clearly understood the importance of the first 10 people in any organization. Why are those first 10 hires so critical?

Vikram Shekhawat: Great question again. This is a learning that came a little late. When you raise money and suddenly see a lot of traction, your instinct is to bring in an A-team.

Vikram Shekhawat: In your mind, that A-team consists of people with strong pedigrees and significant experience—maybe 10 to 12 years in the field, backed by top-tier colleges.

Vikram Shekhawat: That’s the mistake we initially made. We corrected it eventually, but hiring those profiles slowed us down. People with a lot of experience often move at their own pace. They may not have the same zeal or willingness to unlearn, learn, and relearn—which is essential for the first 10 employees.

Vikram Shekhawat: The playbook is different for each business. What worked for me in banking didn’t necessarily work in the education space. While some transferable skills exist, the execution strategy needs to be rethought for every new domain.

Vikram Shekhawat: When you hire people with vintage experience, they might not see it the same way. You want people who can operate with speed and agility—because startups demand that.

Vikram Shekhawat: You also need people who are hungry, who are willing to experiment, break barriers, try things that haven’t been done before, and then come back with data—either to double down or pivot quickly.

Vikram Shekhawat: That kind of mindset rarely comes with folks from traditional, slow-moving environments. So yes, your first 10 hires can make or break your company.

Alejandro Cremades: So obviously, as you said, it was time to turn the page—and something exciting happened: you launched your latest baby, Model X. Talk to us about this. There was a whole sequence of events—you moved to Canada, started meeting people… How did all that lead to you founding this company?

Vikram Shekhawat: I moved to Canada in 2022, right after exiting Pariksha. Initially, I thought I’d try to build something of my own again.

Vikram Shekhawat: I noticed that Canada offered something the Indian market at the time didn’t—easy access to capital, mostly because of its proximity to the U.S. I believed I could bring my expertise, identify a problem, and solve it faster than others.

Vikram Shekhawat: Initially, I considered launching a fintech startup, but that required open banking. Since open banking hadn’t been introduced yet, I had to stall the idea. Eventually, I had to scrap it altogether.

Vikram Shekhawat: While I was working on that, I also started helping startups affiliated with Invest Ottawa, the Brampton Entrepreneur Centre, and TBDC in Canada. I helped these startups identify minimum viable products, find product-market fit, and develop go-to-market strategies—drawing from my own experience.

Vikram Shekhawat: I also helped connect them with potential investors once they reached a decent stage. During this process, I met Jeremy, Pei, and Haneev, who were building a different solution at the time.

Vikram Shekhawat: After connecting with them, we realized there was strong alignment. We decided that I should come on board and that we should build something together.

Vikram Shekhawat: I got onboarded in January 2024. The initial idea we were building was a bite-sized learning platform for enterprises. In my view, because AI had significantly changed the game, this product was a really good one to have—but not a must-have in the market.

Vikram Shekhawat: Then we decided to pivot. We changed the offering from what it was and leaned more into the AI wave. That’s when Model X came in.

Vikram Shekhawat: Model X initially started as the first multimodal AI training platform. It supported multimodal input and output—so any asset could be created in the format of your choice, whether that’s video, audio, presentations, and so forth. We started with that and rolled out the first version of the product during Collision in Toronto. We had about 150 small- and medium-sized businesses jump on the bandwagon very quickly.

Vikram Shekhawat: We observed the usage and noticed an instant pull toward what we had built. But over the next month or so, we realized usage was slipping.

Vikram Shekhawat: That’s when we identified the core problem. Initially, we believed users needed one solution—they didn’t want to juggle 10 different tools or deal with 10 subscriptions. They didn’t want the complexity of multiple platforms or the learning curve that comes with them.

Vikram Shekhawat: That was the problem we aimed to solve. We initially targeted SMEs because that was a segment I had connections with from the fintech idea I was previously building. That segment remains underserved.

Vikram Shekhawat: When we gave the platform to these users, we noticed two key problems: first, they weren’t good at prompt writing; and second, they didn’t know what they could use the platform for. The root cause was that most large language models don’t understand your persona.

Vikram Shekhawat: They can’t guide you based on your unique needs. So we solved that problem by adding a layer of business intelligence—something that became a game changer. In the first 10 seconds of joining the platform, it quickly understands who you are, your role, the company you’re part of, and the industry you operate in.

Vikram Shekhawat: Based on these parameters, it can recommend the most likely challenges or goals you have. Model X then takes care of prompt generation and provides suggestions tailored to help you overcome those challenges and achieve your goals.

Vikram Shekhawat: We rolled out this version to nearly 500 SMBs across categories like immigration, real estate, healthcare, NGOs, and restaurants.

Vikram Shekhawat: We saw significant AI adoption. These users began to understand how to use the tools. Then came the real test—would they be willing to pay for it? We began monetizing toward the end of December.

Vikram Shekhawat: We started by monetizing one specific category, and we saw 50% adoption in that category.

Alejandro Cremades: So how do you guys actually make money? When you say monetize, what does that look like?

Vikram Shekhawat: It’s a subscription-based platform. We try to make it extremely affordable and accessible. Users pay a minimal monthly fee, and they can then create any asset or fully leverage everything the platform offers.

Vikram Shekhawat: We continue to add more features and expand functionality—making the platform more comprehensive so users don’t have to go anywhere else. Another major development, which we believe will be a turning point for us, is the introduction of an agentic interface.

Vikram Shekhawat: We’re launching an agent called Agent Wick. As a small- or medium-sized business user, we don’t want you to face the challenges that typically come with LLMs or agentic AI platforms.

Vikram Shekhawat: We want you to simply talk to the agent as if you’re speaking to your co-founder—just like the conversation we’re having now. You talk to the agent, and it takes care of everything else for you: writing prompts, creating assets, doing research, brainstorming ideas—everything.

Vikram Shekhawat: It’s like having a very capable AI running mate, equipped with the best of what AI has to offer and making that accessible to you in real time.

Alejandro Cremades: That’s amazing. So now, how are you thinking about fundraising? You’ve had great success. You’re the kind of founder investors love to bet on, since that increases the odds of success.

Alejandro Cremades: How are you thinking about capital raising and bringing in the right people for the right reasons?

Vikram Shekhawat: Great question. The way we see it, you don’t just need someone who believes in the idea or is willing to back it—you need someone who acts as an extension of your business.

Vikram Shekhawat: Someone who can connect you to potential clients, help expand your outreach, and serve as a sounding board. Someone you can brainstorm ideas with. That’s the kind of fit we’re seeing with a number of VCs who are currently evaluating an investment in our company.

Vikram Shekhawat: We’re using them not just for capital, but as an extension of the business. You need investors who bring more than money—people who believe in the idea the way you do and are willing to back the team through tough times.

Vikram Shekhawat: Every business goes through pivots and changes. I’ve never seen a business scale without evolving from its initial idea. So you want investors who continue to believe and support you through those transitions. We’re currently speaking with several large VCs in Canada and the U.S., and we’ve received strong interest. You should be hearing about a sizable round soon.

Alejandro Cremades: That’s fantastic. Obviously, people are betting on the vision—not just investors, but also employees, customers, and everyone rallying around what the future will look like.

Alejandro Cremades: So, if you went to sleep tonight, Vikram, and woke up in a world where the vision of Model X is fully realized, what does that world look like?

Vikram Shekhawat: That’s a good one. The current market we’re serving is very specific, but I see Model X becoming much bigger than it is today.

Vikram Shekhawat: I’d want to see at least 100 million small- and medium-sized businesses growing with the help of Model X. But beyond that, if you look at the world of AI today, there are over 8 billion people globally.

Vikram Shekhawat: What we’ve built is similar to Jarvis from Iron Man. It can be useful to anyone—even beyond SMBs. AI currently has less than 10% penetration. There are about 700 million users globally, with only 315 million active users—most of whom are enterprise users.

Vikram Shekhawat: My vision for Model X is to see 100 million SMBs using it. And with Agent Wick—our version of Jarvis—I’d want to see 5 billion people using it on a daily basis for everything they need. I want it to make a meaningful impact in their daily lives.

Alejandro Cremades: So we’re talking about the future here, but let’s also reflect on the past. Imagine I put you in a time machine and take you back to when you had just finished your master’s degree and were thinking about starting your first business.

Alejandro Cremades: If you had the chance to stop that younger Vikram and give him one piece of advice before launching, what would it be—and why, given everything you know now?

Vikram Shekhawat: Great question. This one needs some thought. Like I said, I started late. Part of the reason was the kind of peers I had. But the biggest thing I would tell my younger self is: don’t be afraid of large players already operating in the space.

Vikram Shekhawat: If you want to become the next big thing, and someone else is already in the market, you need to focus on your strengths. If you back away from an opportunity just because there’s a bigger player dominating the space, you’re holding yourself back.

Vikram Shekhawat: Believe that what you’re doing can make a sizable impact. Focus on your strengths and the unique value you bring to the table—that’s what will get you there. No player is too big to be challenged.

Vikram Shekhawat: The issue with large enterprises is that they move very slowly. The bigger the ship, the harder it is to steer. Small companies like ours have the advantage of speed—we can pivot, adapt, and make decisions quickly.

Vikram Shekhawat: That’s not something big enterprises can do easily. So don’t be afraid of bigger players. Go at it, give it your best shot, focus on your strengths, and build from there.

Alejandro Cremades: I love that, Vikram. For the people listening who would like to reach out and say hi, what’s the best way to do so?

Vikram Shekhawat: I’m available to connect on LinkedIn, and I’m also quite approachable via email. My email is [email protected].

Alejandro Cremades: Amazing. Well, Vikram, thank you so much for being on the DealMaker Show. It has been an absolute honor to have you with us today.

Vikram Shekhawat: Likewise—thanks for having me on the show, Alejandro. Great talking to you.

*****

If you like the show, make sure that you hit that subscribe button. If you can leave a review as well, that would be fantastic. And if you got any value either from this episode or from the show itself, share it with a friend. Perhaps they will also appreciate it. Also, remember, if you need any help, whether it is with your fundraising efforts or with selling your business, you can reach me at [email protected]

 

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