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

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

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” • How pre-board conversations shape outcomes before meetings begin • The psychology behind defensive founder responses • Why some founders keep the CEO seat — and others lose it • The three real-world outcomes after confidence breaks: performance framework, role transition, or exit • How founders can prepare before they ever walk into this room Not every difficult board meeting ends with a founder losing their company. But almost all of them begin long before the meeting itself.

The Document, Founder Signed Without Reading "Every Clause in a Term Sheet"

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 investors actually decide to fund companies. NEXT EPISODE TEASER Episode 4: The Board Meeting Nobody Talks About. An investor who has lost confidence in the founder, a company running out of runway, and the conversation that happens behind closed doors — and what it means for the founder's role in their own company.

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

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 information risk can kill a deal faster than weak metrics. DEAL TERMS REFERENCED: • Investment: $2M | Pre-money valuation: $8M | Post-money: $10M • Structure: Priced seed round • Investor rights: Pro-rata rights, observer participation • Liquidation preference: 1x non-participating • Founder vesting: 4 years with 1-year cliff KEY CONCEPTS EXPLAINED THIS EPISODE: • Due diligence: The investor verification and risk assessment process after a term sheet • NRR (Net Revenue Retention): Measures expansion and retention revenue from existing customers • ARR (Annual Recurring Revenue): Predictable recurring annual revenue from contracts • Customer concentration risk: Overdependence on a small number of customers • Founder-market fit: When founders deeply understand the market because they’ve lived the problem • Information risk: The risk that founders are filtering or withholding important information • Pro-rata rights: Investor’s right to maintain ownership in future funding rounds • Liquidation preference: Determines payout order during exits or acquisitions • Vesting schedule: Timeline over which founders earn ownership in their shares WHAT YOU’LL LEARN: • Why term sheets are not final until diligence is complete • The real reasons investors pull deals • How investors evaluate founder behavior under pressure • The mistakes founders make when presenting metrics • How proactive disclosure can actually strengthen investor confidence • The framework smart founders use before fundraising: the “risk register.”

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

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 | Dilution: 20% • Structure: SAFE with $16M cap and 20% discount • Investor rights: Pro-rata, observer board seat • Runway: ~18 months at projected burn rate