Talvinder Singh

Talvinder Singh

Y Combinator Logo Batch: W21

Achievements

  • 3x founder and CEO of Pragmatic Leaders, an AI-powered corporate training startup backed by Y Combinator (W21)
  • Built a community of over 30, 000 product managers and curated a dedicated job board
  • Served as Product Head at OYO Rooms, shaping user experience and growth strategies
  • Held the role of Chief Product Officer at Freecultr, an online fashion platform
  • Founded Tushky, an online marketplace for local activities incubated at 500 Startups
  • Recognized as a keynote speaker and featured in Forbes, TechCrunch, NBC, Times of India

In love with Talvinder Singh

Yo, peep this story about Talvinder Singh. The guy’s a straight-up legend in the startup world. He’s a 3x founder and a total product whiz, and right now he’s running the show as Co-Founder and CEO of Pragmatic Leaders, which is this badass AI-powered corporate training startup backed by Y Combinator (W21). No cap, that’s a huge deal – YC doesn’t just give that to anyone.

So, how did he get here? Talvinder’s been in the game for over 15 years. He’s seen it all, started from scratch, built companies, led product teams, and crushed it at some big names like OYO Rooms and Freecultr. At OYO, he was Product Head, so he was the guy shaping their user experience and growth strategies. Then he took the Chief Product Officer role at Freecultr, which was all about online fashion. Before that, he founded Tushky, an online marketplace for local activities, incubated at 500 Startups. Basically, he’s been jumping into different markets, trying new things, and making shit happen.

What’s crazy is, Talvinder isn’t just about building companies. He’s also all-in on education and community. He built a massive network of over 30,000 product managers and curates a job board for them. He’s spoken at big shows, featured in Forbes, TechCrunch, NBC, Times of India, basically, he’s the real deal in the product and startup space.

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His background? He’s an IIT Bombay grad, so the tech creds are real. But what really stands out is his drive. He’s always been about creating value, pushing boundaries, and helping others level up. That’s why he jumped into startups, why he’s constantly learning and sharing. His process screams one thing: he’s in this to make a real impact, not just chase cash. He sees technology as a way to change how people learn, work, and grow, which is why he’s now all-in on AI and corporate training with Pragmatic Leaders.

Bottom line: Talvinder Singh isn’t just some guy selling products. He’s a builder, a connector, a mentor. He’s someone who’s been through the trenches, learned from failures, and now is leveraging AI to transform corporate learning. If you ask me, he’s one of those founders who’s not just riding the wave but shaping the future. That’s why you should keep an eye on him, he’s the real deal, no bullshit.

Founder ID: 104476

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