Episode 86: Private Communities Are the Future w/Utsav Somani
About Utsav Somani:
Utsav is the founder of Offline — India’s most exclusive community of scaled-up tech founders. Early members include co-founders of Zomato, Country Delight, Ultrahuman, Noise, CoinDCX, and many more.
He is responsible for bringing AngelList to India. AngelList India became the most active seed investor in the country with 500 investments since it’s launch in 2018. He runs 2 separate funds called iSeed and Galaxy that have around $100M in AUM. Utsav has personally invested in companies like BharatPe, CoinDCX, Pristyn Care, Jupiter, Park+ along with top-tier VC firms.
Listen on:
Key Insights:
1. The Art of Strategic Rejection
Utsav has mastered saying no without burning bridges. His technique? "Can I politely decline this opportunity?"—a simple phrase that asks for permission to refuse, making it nearly impossible for someone to push back. He's refined his filter mechanism over a decade, accepting that early regrets taught him to value his time above FOMO.
2. Cold Outreach > Warm Intros
While most people chase warm introductions, Utsav deliberately chooses cold outreach. His reasoning: warm intros come pre-loaded with bias and colored opinions. In today's world, everyone's contact information is publicly available—Twitter DMs are open, emails are on Apollo. If you can craft a crisp message that offers genuine value, busy people will respond. The more creative your approach, the more respect you'll earn.
3. Depth Over Width, Always
From capping meetings at 30 minutes to building Offline for just 300 members instead of thousands, Utsav obsesses over depth. He'd rather know when a member's child is being born or their IPO is happening than have surface-level connections with hundreds. This philosophy extends to his view that most relationships in people's address books lack any real depth—a realization that hits as people mature.
4. The Reversible Decision Framework
Utsav uses Jeff Bezos's one-way versus two-way door framework religiously. Reversible decisions? Move fast, exercise judgment, be okay being wrong occasionally. Irreversible decisions? Sleep on it, think deeply, then exercise judgment. This mental model helps him analyze his weekly wins and losses (marked in green, red, or yellow) without getting paralyzed by overthinking or moving recklessly on critical choices.
In this conversation, we talk about:
00:00 Intro
02:13 Navigating Introversion
05:40 The Art of Cold Outreach
07:23 Reflecting on a Decade of Investing
10:51 Challenges and Learnings in Angel Investing
12:38 Building the Community
15:21 The Vision for Offline
18:05 Executive Coaching and Community Building
21:14 Building a Strong Cap Table
21:46 The Importance of Monopoly and Control
24:13 Private Paid Communities
30:32 Decision-Making Framework
34:07 Balancing Work and Personal Life
35:57 Defining Success
36:33 Key Takeaways from the Conversation
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