First-Time Founders - Are You Raising? Set a Valuation Cap You Can Actually Defend.
Most first-time founders pick a valuation cap by pattern-matching whatever another founder in their network raised at. That's not underwriting. That's guessing with more steps.
In this 60-minute workshop, Sadaf Ayub walks through The Underwriting Framework, the full-stack diagnostic she uses to determine whether founders are ready to raise and what cap they can defend. We'll build a live spreadsheet model using the same inputs she pulls when evaluating a real founder, and watch the model push a cap up or down as founders' capital, milestones, investor signal, and risk-vs-gaps profile shift.
What you'll walk away with:
The Underwriting Framework: the full-stack diagnostic Sadaf uses to determine founder readiness
A working spreadsheet template you can adapt for your own raise
A concrete method for defending your valuation cap in front of institutional investors
Dilution scenarios at Series A conversion under different SAFE cap choices
Who this is for:
First-time founders raising pre-seed or seed on SAFEs
Founders who've been offered a SAFE and want to know if the cap is fair
Anyone approaching a raise in Q4 2026 or Q1 2027
Founders confused about post-money vs pre-money SAFE dilution
Format: 60 minutes, live on YouTube. ~40 min technical walkthrough with live build, ~15 min live Q&A.
About the series
Part of the TwoSetAI Workshop series.
More sessions:
July 17: Why multi-agent systems fail
July 31: Inside AgensFlow
August 14: Token Budgets for Coding Agents
August 28: Self-Improving Agent Loops
September 18: Building A Personal Agent That Actually Works and Sounds Like You
September 25: Behind Navigator n2: The Recursive Training Loop That Made a 27B Model Beat GPT-5.6 and Claude
October 2: How Enterprises Are Actually Adopting AI: From the Boardroom to Bare Metal
October 16: One Person, Many Voices: How to Build Agents That Sound Like a Real Person
October 30: First-Time Founders - Are You Raising? Set a Valuation Cap You Can Actually Defend.
November 13: How Many AI Agents Are Running in Your Company?
December 4: Anyone Can Build. Not Everyone Gets Heard.
December 11: Your AI Agent Is Probabilistic. Its Decisions Don't Have to Be.
See all upcoming sessions: https://twosetai.com/lab/workshops/
About the instructor
Sadaf Ayub is a fractional operations, strategy, and finance partner. She’s spent 15 years advising senior leaders, including at Google, Meta, and AI startups. Now she's the operational adult technical founders bring in when they want big-tech rigor without big-tech headcount. Her clients call her when they're deciding what to build or whether to raise.
About the host
Angelina Yang runs TwoSetAI and hosts TwoSetAI and Decoding AI Builders, long-form interview platforms where she's interviewed 100+ AI founders shaping this era. fast.ai fellow. 2024 Anthropic Build Tournament winner. Curates the workshop series and connects the speakers with builders who care.
Hosted by TwoSetAI.
Past events replay
July 17: Stop Your Agents From Spinning, with Nicole Königstein
July 31: Inside AgensFlow: Design Your Reliability Layer for Your AI Agents, with Nicole Königstein
August 14: Token Budgets for Coding Agents, with Nicole Königstein
August 28: Self-Improving Agent Loops Without Breaking Your Budget, with Nicole Königstein
September 18: Building A Personal Agent That Actually Works and Sounds Like You, with Ahmet İlten of The Sentience Company
September 25: Behind Navigator n2: How did Yutori make AI agents 10x cheaper? With Skanda Vaidyanath of Yutori