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Ajay Yadav, a first-generation immigrant entrepreneur and angel investor, has received recognition from notable sources such as Forbes, CNN, HuffPost, and TechCrunch. Born in India, Ajay relocated to suburban Pennsylvania when he was 17. He learned English and experienced a harsh winter in only a denim jacket. After hearing that success could be found in New York, he decided to move there just six months later, finding an apartment on Craigslist. During college, Ajay pursued side projects and businesses instead of attending lectures like his peers. One of his ventures was a digital classifieds site called EzeeAdvertise, designed specifically for the Indian market. With no outside support, he managed to make the business financially viable. Ajay's next project was an online roommate-finding app called Roomi. Venturing beyond the classroom, he led Roomi to raise over 20 million dollars and attract over 3 million users. Throughout this journey, Ajay gained valuable insights on leading teams, generating revenue, and learning from his experiences to become a well-rounded leader. Dedicated to creating tools that connect people in today's remote-focused world, Ajay was honored in the Forbes 30 under 30 list in 2017 for his achievements in consumer technology. Motivated by the determination of immigrant, women, and BIPOC entrepreneurs, he began investing in companies like Coffee Meets Bagel, Doorvest, Simplified, and Squire, while also advising minority-led startups. Currently, Ajay has co-founded Simplified, a comprehensive marketing software that combines content creation, collaboration, and publishing tools into one application. As a content creator, he knows the effort required to create and publish content. Simplified, powered by AI, aims to help creators produce more content, reduce costs, and grow their businesses more efficiently.
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Everyone says, “Build fast and raise.” I did the opposite. Closed a paying customer before I wrote a single line of code. Why? Because easy money is gone. We’re in a time where traction, ideas, or a little revenue can still get you funded. But for AI-driven ventures, to achieve 10x-plus returns, it has to stick. So, I took a revenue-first approach: > Revenue first > Company Formation second > Fundraising third This approach is unlike anything I’ve done before. Now, we’re navigating the next phase: > Building the product based on our thesis and real paying customer feedback > Building a team that really believes in the vision without any funding > Honing in on the ICP and figuring out what our wedge would be > Execution to close more customers (Follow along as I share each step in real-time.) I’d call this the revenue stage rather than the venturing stage. There’s so much to figure out, but one thing’s clear: Start with revenue. Build from there. Everything else follows.
Most founders think the hardest part of fundraising is getting a yes. But after raising $30M across two VC-backed startups, I’ve learned something else: The hardest part is realizing what that “yes” actually costs you. → It costs you time → It costs you product focus → And sometimes, it costs you your own clarity as a founder Raising money is supposed to unlock growth. But too often, it replaces real feedback with pitch feedback. It pulls you into forecasting when you should be shipping. It makes you optimize for the wrong customer, which is the investor. I know, because I’ve done it. Twice. Now with Otto, we’re bootstrapped. Small team, fast loops, 38 paying customers. We’re not trying to raise. We’re trying to get sharper every week. And we’re solving for revenue, not just runway. I’m not against VC. It works if you know exactly why you’re raising and what you’ll trade to get it. But if you’re early and still figuring it out? You don’t need funding. You need clarity. You need a working product. You need one person who’ll pay for what you’re building, today. Everything else can wait.
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