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The Unplanned 10: Traditional playbooks preach linear trajectories: pick a degree, climb the ladder, execute the ten-year plan. Yet, the most disruptive shifts in tech, media, and venture building rarely follow a neat syllabus. Real moats are constructed in the unplanned zones—through spontaneous experiments, public proof-of-work, and mid-course pivots that turn unexpected realizations into formidable operations.
In this inaugural edition of The Unplanned 10, we profile ten operators, creators, and founders who ditched rigid blueprints to build compounding leverage in an unscripted digital economy.
Adit Sreenivasan (Founder, Moat Media)[/caption]
1. Adit Sreenivasan (Founder, Moat Media)
Adit is the founder of Moat Media, whose journey reflects precision, discipline, and an analytical mind built through an ML background. Built through hands-on execution rather than a conventional path, he treats content growth as a repeatable system, not a stroke of luck.
His insight came from his time as a VC analyst at 2AM VC, working with 50+ founders across the US, UK, and Southeast Asia: even the sharpest operators stayed invisible with no moat around their story. That shaped Moat Media’s mission: “We build moats for founders.”
Proof lives in the numbers: 7M+ views generated across his own content, 18K LinkedIn followers, and scaling a co-founder’s LinkedIn presence from 85 to over 1,800 followers in six months.
Adit continues to expand Moat Media across strong-currency markets including the UK, Singapore, UAE, and Canada, steadily building a future-ready agency that bridges founder ambition with investor trust.
Stewart Butterfield (Co-Founder, Slack & Flickr)[/caption]
2. Stewart Butterfield (Co-Founder, Slack & Flickr)
Stewart Butterfield never set out to build an enterprise communication behemoth. Twice, he attempted to launch visionary multiplayer online games (Game Neverending and Glitch). Both failed commercially.
Instead of shutting down completely, Butterfield extracted the internal side-features his team used during development: a simple web-based photo-sharing tool became Flickr, and an internal IRC communication engine became Slack. By recognizing that internal operational utilities held far more value than the original core product, Butterfield engineered one of the most profitable strategic pivots in modern SaaS history.
Sridhar Vembu (Founder & CEO, Zoho Corporation)[/caption]
3. Sridhar Vembu (Founder & CEO, Zoho Corporation)
While late-90s dot-com founders rushed to Silicon Valley for venture checks and splashy public exits, Sridhar Vembu chose an entirely unplanned, counter-intuitive route. Starting with network software under AdventNet, he chose bootstrapping over institutional capital and patient engineering over burn-rate hypergrowth.
Vembu went on to pioneer modern rural tech hubs by moving operations into rural Tamil Nadu, turning grassroots talent into elite software engineers. Today, Zoho stands as a multi-billion-dollar bootstrapped SaaS powerhouse, proving that sustainable software moats thrive outside traditional tech hubs.
Falguni Nayar (Founder & CEO, Nykaa)[/caption]
4. Falguni Nayar (Founder & CEO, Nykaa)
Falguni Nayar spent over two decades navigating boardroom corridors as an investment banker at Kotak Mahindra. She had reached the peak of a traditional finance career, but at age 50, she stepped away from advisory boardrooms to enter the chaotic realm of direct-to-consumer e-commerce.
With no prior background in beauty retail or supply chain engineering, Nayar spotted a gap in India’s fragmented cosmetics market. By betting on an authentic inventory-led model when third-party marketplaces were the norm, she scaled Nykaa into a profitable, publicly listed beauty powerhouse.
Brian Chesky & Joe Gebbia (Co-Founders, Airbnb)[/caption]
5. Brian Chesky & Joe Gebbia (Co-Founders, Airbnb)
Airbnb was not born out of an ambitious corporate strategy; it was born out of an urgent need to make rent in San Francisco. When a major design conference filled up local hotels, Chesky and Gebbia laid three air mattresses on their living room floor and served homemade breakfast to designers.
That scrappy weekend hustle evolved into an international hospitality network that owns zero real estate. By turning an unplanned living room experiment into a global network effect, they dismantled the traditional assumptions of the hotel industry.
Ayush Wadhwa (Founder, Owled Media)[/caption]
6. Ayush Wadhwa (Founder, Owled Media)
While pursuing an engineering degree, Ayush Wadhwa started tinkering with cameras, video software, and visual storytelling out of pure creative curiosity. Rather than following the campus placement pipeline, he focused on public execution, publishing videos and building creative assets for early-stage clients.
Without an agency background or traditional media funding, Wadhwa expanded that solo production hustle into Owled Media, scaling it into an agile creative partner for tier-one brands like Disney+ Hotstar, Cred, and HP.
Sharan Hegde (Founder, The 1% Club & Creator)[/caption]
7. Sharan Hegde (Founder, The 1% Club & Creator)
Trapped in a routine corporate consulting role during the 2020 lockdowns, Sharan Hegde picked up his phone and started making 30-second satirical skits about tax laws, credit card points, and compounding interest.
His ability to translate dry personal finance mechanics into engaging, comedic skits bypassed traditional financial advisory gates. What began as a bored lockdown experiment transformed into The 1% Club, turning algorithmic distribution into a scalable fintech, media, and investment collective.
Sanjeev Bikhchandani (Founder, Info Edge Naukri.com)[/caption]
8. Sanjeev Bikhchandani (Founder, Info Edge / Naukri.com)
In the late 1980s, Sanjeev Bikhchandani observed a quiet, recurring behavior: corporate executives in open-plan offices would sneakily flip through the back pages of business magazines to read recruitment advertisements.
He didn’t wait for institutional capital to prove the thesis. Bikhchandani launched a database aggregator out of a servant’s quarter, which evolved into Naukri.com. By building the foundational infrastructure for Indian internet recruitment, he established Info Edge, the investment engine behind consumer giants like Zomato and PolicyBazaar.
Vedant Lamba (Founder, Mainstreet Marketplace)[/caption]
9. Vedant Lamba (Founder, Mainstreet Marketplace)
Vedant Lamba began his entrepreneurial journey simply by vlogging sneaker culture, thrift markets, and street fashion for a niche YouTube audience. There was no clear retail roadmap—just a deep immersion in underground streetwear subcultures.
As demand for authenticated, limited-run sneakers exploded, Lamba shifted his media brand into Mainstreet Marketplace, establishing one of India’s premier luxury resale platforms and proving that niche content communities can organically build retail infrastructure.
Ishan Sharma (Co-Founder, MarkitUp)[/caption]
10. Ishan Sharma (Co-Founder, MarkitUp)
Entering BITS Pilani with standard engineering goals, Ishan Sharma quickly gravitated toward the open web. He began documenting his self-taught coding journeys, freelancing triumphs, and creator interviews in raw, long-form videos.
Choosing to leave his degree behind to build digital-first ventures, Sharma turned his audience into a talent engine, launching MarkitUp to handle digital growth and production for enterprise clients. His trajectory showcases the power of building proof-of-work in public before stepping into the business world.
Success is rarely a straight line. What separates these 10 trailblazers from the rest isn’t just pure luck—it is their acute readiness to spot an unforeseen opportunity and the relentless courage to pivot. The blueprint didn’t exist until they decided to build it.
Which unplanned journey inspired you the most? Share your thoughts at our social media platforms, or let us know who deserves a spot in our next edition of The Unplanned 10.