Episode 17 of The Offline Network, hosts Utsav and Dhruv are joined by two builders from opposite sides of the table. Two perspectives. One question: what separates the outliers from everyone else in this new AI age?
This episode brings together Anand Chandrasekaran, now building HiOctave with Khosla Ventures, reimagining customer experience for small businesses. Anand’s new chapter is about giving small businesses enterprise-grade AI tools to automate bookings, sales, and customer conversations, without losing the human touch.Akshay Mehra, Partner at Hummingbird Ventures, the VC that backs just 0.1% of what it sees. He brings the investor’s lens, forged through early bets on Lovable and Vance, and a philosophy that founder quality is 80% of the outcome.
Together, they unpack:
What defines a 0.1% founder in today’s AI market
How to build when speed, compute cost, and retention collide
Why the next wave of outliers won’t follow Silicon Valley’s playbook
What small businesses get wrong about automation
The one founder habit that changes survival odds
Our first dual-guest segment – raw, real, and built for this AI moment.
This episode was made possible by Smartworks – India’s largest managed office platform.
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