AI for Startup Judgment
🚀 With Glen Caruso and David Williams🚀
Join a A 60-Minute Micro Workshop for Founders, Operators, and Investors
Startups rarely fail because they lack tools.
They fail because early decisions are made with
Incomplete information
Founder bias
Unchallenged assumptions
Weak second-order thinking
This micro-workshop introduces a practical way founders, startup employees, and investors can use AI to pressure-test thinking before commitments are locked in.
The goal
Improve decision quality early, when leverage is highest.
Why This Session at the AIA - Artificial Intelligence Algarve community
The AIA brings together people already close to AI, but proximity to AI tools doesn’t automatically translate into better decisions.
This session is designed to close that gap.
Instead of focusing on models, prompts, or demos, the workshop shows how AI can be used as a judgment-support system inside real startup decisions: product, market, growth, hiring, and capital allocation.
It complements the AI Hub’s mission by moving the conversation from capability --> decision quality --> outcomes.
Target Audience
Ideal for AIA members and the broader Algarve startup ecosystem, including:
Startup founders (early and growth stage)
Startup employees influencing product, growth, or strategy
Angel investors, advisors, and mentors
Accelerator / incubator program participants
No technical or engineering background required.
What Participants Will Learn
In one focused hour, participants will learn how to:
Use AI to stress-test assumptions, not replace judgment
Surface risks and blind spots founders consistently underweight
Improve clarity before committing time, capital, or reputation
Separate signal from noise in customer feedback and traction
Ask sharper questions of markets, customers, and themselves
This is AI applied to thinking, not task automation.
What We’ll Cover
1. The Real Startup Bottleneck
Why execution usually isn’t the constraint, decision quality is.
2. AI’s Highest-Leverage Role in Startups
AI as a judgment amplifier and pattern-recognition system.
3. The Decision Pressure-Test Framework
A simple, repeatable method to:
Challenge founder assumptions
Explore second-order effects
Identify failure modes early
4. Human Accountability Still Rules
AI can generate, simulate, and propose.
Humans decide, defend, and own outcomes.
5. Live Startup Scenario
A realistic example showing how better thinking early prevents expensive mistakes later.
What This Is (and Isn’t)
This is:
Practical and operator-level
Relevant to real startup decisions
Aligned with AIA members’ interests
Immediately usable after the session
This is NOT:
A tools demo
A technical deep dive
A hype session
A replacement for founder judgment
Why This Matters for the AI Ecosystem
Better founder thinking compounds across the community
Advisors and investors get clearer signal earlier
Capital and mentorship are allocated more effectively
AI capability translates into real outcomes, not just adoption
Early clarity beats late correction.
ABOUT THE SPEAKERS
➤ About the Facilitator
Glen Caruso is an applied AI strategist and the Founder of The Digital Curators.
Glen Caruso is an AI strategist and technology operator who helps senior leaders apply AI as a decision-support system, not a productivity shortcut. Website.
He has held senior roles at Microsoft, Oracle, and Adobe, working across data, advertising, and enterprise platforms as organisations navigated major technology shifts. His work has supported leadership teams at large, complex organisations, including globally recognised brands such as Coca-Cola and MetLife, where decisions carried operational, financial, and reputational responsibility.
Earlier in his career, Glen founded Firecracker Digital, a U.S.-based consultancy acquired by BLiNQ Media, one of Facebook’s earliest global advertising partners. Today, Glen leads The Digital Curators, advising executives and management teams on real-world AI use in high-accountability environments. He also teaches applied AI and decision-making as faculty at a major U.S. public university. This session is designed for senior professionals and leaders who want clarity, control, and confidence as AI becomes embedded in everyday work.
David Williams
David Nicol Williams Jr. is a serial entrepreneur, investor, and mentor who has spent the past three decades at the forefront of digital innovation—from the early days of digital marketing to the rise of the digital nomad economy and today’s AI-driven tech landscape. A longtime CEO, industry speaker, and award-winning entrepreneur, he now advises and invests in early-stage and bootstrap startups through The Doctor Is In The House, helping founders navigate strategy, growth, and capital. Originally from the United States and now based in Portugal for nearly a decade, David focuses on supporting entrepreneurs building the next generation of AI and technology-driven companies.
ABOUT US
🧠 AIA - Artificial Intelligence Algarve
Founded by Algarve Evolution, AIA - Artificial Intelligence Algarve is a community dedicated to exploring and advancing the future of AI in the Algarve region.
🚀 Algarve Evolution
We nurture the ecosystem for startups and entrepreneurs to create global solutions from the Algarve.
A regional initiative founded and promoted collaboratively by Algarve Evolution, Algarve STP, and University of the Algarve, representing stakeholders from corporate, academia and public institutions, to advance the Algarve as a global, competitive and vibrant hub for companies, institutions, entrepreneurs, and investors.