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I sit down with Andrew Wilkinson and we go deep on how he’s restructured his work, his health, and his family office around AI agents. Andrew walks me through Deep Personality (an app he vibe-coded after running psychological screens on himself and his girlfriend), the autonomous SaaS business he runs through agent harnesses like Harbor, and the vector-database setup that lets him query Tiny and his personal holding company like an oracle. We cover where software is headed, why he’s pouring capital into TSMC and data center stocks, and the daily AI workflows he’s built around health, email triage, and a personalized morning podcast. Listeners walk away with concrete prompting tactics, agent architectures, and a frank read on where the moats are moving.
Timestamps:
00:00 – Intro
01:50 – The OpenClaw and Claude Code Unlock
04:53 – Demo: Deep Personality App
10:38 – Harbor: An Agent Harness For Real Companies
12:30 – Autonomous Companies: Hype Vs. Reality
17:30 – Credibility As The Missing Layer For Vibe-Coded Products
20:14 – Centralizing Data Pipelines
21:35 – Vector Databases
23:22 – Transitioning Companies to Agentic Companies
25:22 – Where Andrew Would Build Today
27:10 – The New Interface
28:21 – Why build now
30:59 – Replacing Adapar: A Networth Wealth Platform
33:29 – Services As The New Software
35:46 – G-Brain Explained and Andrew’s OpenClaws
45:31 – Closing Thoughts
Key Points
* Andrew runs a SaaS business called Deep Personality almost entirely through agents, generating roughly $20K of revenue while debugging eats half his time.
* Harbor (github.com/geekforbrains/Harbor) gives agents a GUI-style harness — dev, marketing, and support agents that can autonomously merge PRs and adjust ad budgets across PostHog, Meta, and Reddit.
* Andrew’s family office swapped headcount for a $40K/month Claude bill; his CFO, who had zero coding background, vibe-coded a replacement for Adapar (priced at $50K–$100K/year) in about two weeks.
* Vector databases trained on Tiny and Andrew’s holding company let him query 132 minority investments, P&Ls, and headcount data conversationally.
* For builders today, Andrew suggests aiming for a $1M–$2M product, then parking gains in TSMC and data center exposure given how fast software moats are eroding.
* His best prompting tip: ask the model to interview you with multiple-choice questions before generating any output.
Numbered Section Summaries
1. The December 2025 Claude Code Unlock
Andrew describes the moment Claude Code clicked for him — waking up at 3 or 4 a.m. with ten terminal tabs open, running an entire SaaS business from the back of Ubers in Arizona while traveling laptop-free. The hook is real, the productivity gain is real, and the debugging tax is also real.
2. Harbor And The Architecture Of Autonomous Operations
We dig into Harbor, the agent harness his friend Gavin Vickery built. Marketing, dev, and support agents share a knowledge base, run multivariate ad tests, and auto-merge P0 security fixes. Andrew argues support as a job is months away from disappearing, while marketing agents will reshape what a $100K/month ad budget looks like.
3. The Reality Check On Autonomous Companies
I push back on the autonomous-company narrative around products like Pulsia. Andrew agrees that today’s agents resemble "Zapier zaps with intelligence" — capable but requiring step-by-step instruction like a genius baby. The unlock arrives when context windows reach 5–10 million tokens and a model can hold a whole company in mind.
4. Centralizing Context With G-Brain And Vector Databases
Andrew has standardized on Claude Code as his operating system and routes Fireflies transcripts, emails, and meeting notes nightly into G-Brain (Gary Tan’s vibe-coded vector database tool). Trained on his family office data, the system surfaces $16M invested → $36M current value across 132 deals; trained on Tiny, it acts as the "eye of Sauron" across 24 portfolio companies.
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The Vibe Marketer – Resources for people into vibe marketing/marketing with AI: https://www.thevibemarketer.com/
FIND ME ON SOCIAL
X/Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
LinkedIn: https://www.linkedin.com/in/gisenberg/
FIND ANDREW ON SOCIAL
X/Twitter: https://x.com/awilkinson
Deep Personality: https://deeppersonality.app/
Tiny: https://www.tiny.com/
