How Andrew Wilkinson Uses Opus 4.5 in His Work and Life

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Jan 21, 2026

Andrew Wilkinson, a serial entrepreneur and cofounder of Tiny, shares his innovative use of AI tools like Opus 4.5 and Claude. He discusses his transition from early coding attempts on Replit to now feeling empowered by AI, likening it to having a vast team of engineers at his disposal. Wilkinson reveals his creation of 'Deep Personality', an AI relationship counselor, and talks about automating personal and work tasks, including a custom email client and daily outfit recommendations. He reflects on how these advancements are reshaping his approach to software acquisitions.

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INSIGHT

Vibe Coding Reaches An Inflection Point

Opus 4.5 (Claude/Cloud Code) feels like an "iPhone moment" for vibe coding, enabling end-to-end app creation without heavy engineering.
Andrew says this transforms creators into architects who can move at the speed of thought.

ANECDOTE

Built A Relationship Diagnostic That Hit Home

Andrew built "Deep Personality," a relationship diagnostic that predicted every fight he and his girlfriend have.
He plans to release it publicly after seeing how accurately it analyzed their dynamics.

ANECDOTE

Custom Email Client Built In Days

Andrew used Cloud Code to build a custom email client that matches his triage workflow and integrates with Gmail.
In a week it reached daily-usable quality, replacing long development efforts.

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Entrepreneur Andrew Wilkinson used to sleep nine hours a night. Now he wakes up at 4 a.m. and goes straight to work—because he can’t wait to keep building with Anthropic’s latest model, Opus 4.5.

Two years ago, Wilkinson was obsessed with vibe coding on AI software development platform Replit. It was thrilling to describe something in plain English and watch an app appear, less thrilling when the apps were always broken in some way, often full of maddening bugs. So he set his app creation ambitions aside until technology caught up with them.

Then, a few weeks ago, he started playing with Claude Code and Opus 4.5. It felt, he says, like having a “$100,000-a-month payroll of engineers” working for him around the clock.

Wilkinson is the cofounder of Tiny, a company that buys profitable businesses and holds them for the long term. The Tiny portfolio includes the AeroPress coffee maker and Dribbble, a platform where designers can share their work and find jobs. Dan Shipper had him on AI & I to talk about the automations Wilkinson has built for his work and personal life, including an AI relationship counselor, a custom email client, and a system that texts him outfit recommendations each morning. Wilkinson revealed how all of this individual exploration has changed the way he thinks about buying software companies at Tiny.

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Timestamps:

00:00:00 - Start

00:01:07 - Introduction

00:02:48 - Why Opus 4.5 feels like the iPhone moment for vibe coding

00:08:31 - Why designers have a unique advantage with AI
00:14:10 - How Wilkinson built a custom email client with Claude Code

00:18:13 - An AI trained on your relationship that predicts your fights

00:30:40 - Using AI meeting notes to make your life better
00:35:11 - Don't inject your opinion into prompts

00:40:21 - Wilkinson’s Claude Code tips and workflows

00:47:59 - Your personal stylist is a prompt away

00:53:17 - How AI is changing the way Wilkinson invests in software

Links to resources mentioned in the episode:

Andrew Wilkinson: Andrew Wilkinson (@awilkinson)
The book Wilkinson references in his prompts, when writing copy with AI: Made to Stick
Every’s compound engineering plugin: https://github.com/EveryInc/compound-engineering-plugin