Interview Prompts Produce Better Answers

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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 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.

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LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/

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