Three failed startups. One of India’s biggest B2B exits. Then returning 75% of investor money in the next venture. An entrepreneur who’s lived that arc is bound to have insights for anyone building or thinking of building.

Paras Chopra, founder of Wingify (sold for $200 million), Nintee, and now Lossfunk, joins us this week.

We discuss the small decisions that quietly define your startup: what product to build, how to structure your team, and why setting the right communication culture early can help.

Paras shares what most founders overlook early on : Pricing isn’t about effort you put but about the value you create, why having competitors might actually be better than having none, and how financial metrics often distract from what really matters to customers.

Paras talks about what changed between each attempt of building his startups, and why some lessons only reveal themselves the hard way and what shifts after you’ve seen both failure and success.

Whether you're launching your first company or planning your next, this conversation will give you the clarity needed to tilt the odds in your favor.

Check out The Book of Clarity by Paras Chopra.

00:00 – Startups Should Be Like Cults
02:25 – Building a Founder’s Value System
03:25 – Bet on What Won’t Change in 10 Years
05:15 – What AI Can’t Do Well (Yet)
10:00 – Do Humans Even Want Accuracy?
10:57 – What Founders Should Not Build or Sell
13:35 – Are many competitors better than none?
19:47 – Why Repeating Success Is Hard
21:20 – Customer Value Metrics > Financial Metrics
23:35 – Why Paras’s Startup after Wingify Didn’t Work
27:00 – What Is Micro Communication?
30:41 – Writing Culture in a Startup
32:50 – Obsess Over Organisational Design
37:15 – Is Luck in Our Hands?
41:24 – Why Bias Is Risky for Entrepreneurs
42:35 – Great Startups Look Like Toys at First
44:00 – Why Deep Tech Startups Struggle to Succeed
46:09 – Paras’s New Venture Lossfunk
49:23 – Why Uncertainty Is a Startup Moat
55:56 – What Most Founders Get Wrong About Pricing
57:36 – Should Price be on Effort or Value?
59:23 – Wingify Innovated on Just One Metric
1:00:25 – What Is Failure for Paras?
1:04:08 – Diversify Your Self-Worth Like a Portfolio
1:05:21 – The Startup Game Is a Mental Game
1:06:43 – Did Wingify Create Wealth or Just Money?
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This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice.

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Jack Parsons