Gurmeet Kaur

Episode 1: "The $4M Bet — How One VC Said Yes When Everyone Else Said No"

Business EN ↓ 4 episodes

What makes one investor write a $4M check while everyone else walks away? In Episode 1 of Inside The Deal Process, we break down the hidden psychology behind conviction investing — when a single VC sees opportunity where the market sees risk. We unpack: why most investors rejected the deal what the lead investor saw differently how venture firms think about asymmetric upside the role of timing, founder psychology, and market narratives why consensus is often the enemy of outsized returns how great investors make decisions under uncertainty This episode is not about startup hype. It’s about und...

Author

Gurmeet Kaur

Episodes

The Board Meeting Nobody Talks About That Can End a Founder's Role in Their Own Company 24.05.2026 30:45

Topic: The Board Meeting Nobody Talks About — Lost Confidence, Leadership Risk, and Founder Survival Hypothetical — Founder: Alex — CEO of Meridian Logistics, SaaS for freight & logistics, $620K ARR, 7 months runway remaining Investor: Orion Ventures — Series A lead, represented by partner Harvey. This episode explores: • What investors actually mean when they say they have “lost confidence” •...

The Document, Founder Signed Without Reading "Every Clause in a Term Sheet" 20.05.2026 32:10

Topic: Term sheet anatomy — valuation, control, liquidation, protection clauses Hypothetical - 1. Founders: Tariq & Nina — SaaS for legal ops, $220K ARR, raising $5M seed 2. Investor: Orion Ventures — $150M early-stage fund 3. Term sheet: $5M investment, $18M pre-money, standard Series Seed terms from Orion Ventures. Welcome to Inside the Deal Process — the show where we break down how investo...

Episode 2 - founder who got the term sheet, then lost it. What happened in due diligence? 12.05.2026 22:53

Today’s episode is about a startup that got the term sheet… and then lost the deal in due diligence. A B2B SaaS company with strong growth, real customers, and investor interest watches a $2M seed round disappear after investors uncover issues the founders thought were “probably fine.” We break down what actually happens after a term sheet, how investors think during due diligence, and why informa...

Episode 1 - The $4M Bet — How One VC Said Yes When Everyone Else Said No 10.05.2026 19:21

Welcome to Inside the Deal Process — the show where we break down how investors actually decide to fund companies. Today’s episode is about A pre-revenue SaaS startup lands a $4M seed round from a VC who passed on better-looking companies. We dissect the deal from both sides of the table. EPISODE CHEAT SHEET DEAL TERMS REFERENCED: • Pre-money valuation: $16M | Investment: $4M | Post-money: $20M |...