Break everything but Wink 😉 - Italian Grit meets Silicon Valley ft. Isabella De Rosa | Ep.29

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Break everything but Wink 😉 - Italian Grit meets Silicon Valley ft. Isabella De Rosa | Ep.29

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In this episode of Startups Dil Se, we sit down with Isabella De Rosa, the Italian founder and CEO of WinkSuite a bootstrapped SaaS platform helping brands run smarter promotions, loyalty programs, and employee incentivization campaigns. Isabella joined us straight from San Francisco, just one week after we met at an @innovitsf networking event, and she brought an incredible story with her.

From burning out running a remote agency in Amsterdam in her twenties, to taking a full year off to reset, to coming back and building a startup from scratch in Italy — Isabella's journey is raw, real, and packed with lessons for any founder at any stage. We get into how Wink Suite went from online sweepstakes to #b2b sales gamification, what bootstrapping a product by "faking it" actually looks like in practice, and why she keeps walking away from investors even when the conversations get close.

We also talk Silicon Valley vs. Italy, the reality of being a woman founder in rooms full of men, and why she refuses to slap an "AI-first" label on her platform just because it's 2026.

🔔 If you found this episode valuable, don't forget to like, subscribe, and hit the notification bell so you never miss a new episode of Startups Dil Se.

💬 Drop your thoughts in the comments — What was your biggest takeaway from Isabella's story?

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