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How One Entrepreneur Runs Two Companies and 100+ Events Using AI Tools

From AI note-takers to cloud-based automation, this system redefines productivity. Could this be the future of multi-business management?

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How One Entrepreneur Runs Two Companies and 100+ Events Using AI Tools

I'm an entrepreneur, creative, and investor based in New York. In a typical week, I've got a lot on my plate. I host over a hundred events a year for more than 20,000 people across New York, San Francisco, and Austin. I publish text and video content that generates millions of impressions monthly on LinkedIn, X, TikTok, and via email, reaching an audience of over 200,000 followers. As an angel investor, I've backed more than 20 startups. I advise companies on B2B marketing and growth strategies. I run two businesses: Fibe, an events and media company, and The Shortlist NYC, a recruiting event series for early-stage startups.

Most people hear this list and assume I've got a massive team behind me. I don't. When I left Google and Meta to build my own thing, I had to create my own revenue streams—and the chaos came with the territory. What made it all manageable, and eventually scalable, wasn't just hard work. It was tools. Specifically: AI and the systems I've built around it. Here's what I use and why.

Claude Code: My LLM Operating System I think of Claude Code the way someone else might think of a chief of staff. It's not just a coding assistant—it's my operating system. It understands the context of my businesses, has access to my systems, and can execute tasks without me having to set everything up from scratch each time. Through a Model Context Protocol (MCP) integration, it connects directly to my Notion workspace, meaning it can automatically read, write, and organize my project management database. It plugs into my CRM, designs content, stress-tests ideas, drafts emails, builds automations, and handles the kind of cognitive work that used to eat up half my day.

Notion and Airtable: The Database Layer Notion is where I think. Airtable is where I track. I use Notion as the primary database for all my TikTok and LinkedIn content—scripts, drafts, calendars, and status tracking for everything that needs to go live. Since it's connected to Claude Code via MCP, much of this runs on autopilot. Content gets categorized, scheduled, and organized without me manually updating rows.

Airtable handles contact data and forms. Whenever someone signs up for an event, applies to The Shortlist, or submits a partnership inquiry, that data flows into Airtable. It's the operational layer—more structured, relational, and better suited for the kind of data I need to query and manipulate.

Zo Computer: My Second Brain (That I've Never Touched) I have a computer I've never physically interacted with. It lives in the cloud and runs while I sleep. Zo is a personal AI cloud computer that lets me build automations, host apps, run scripts, and connect to my tools. I use it for background monitoring, hosting lightweight custom tools, and automating tasks that once required either an assistant or significant manual effort.

Lovable: From Idea to Prototype in Hours For The Shortlist, I needed software that didn't exist—something that could take a pool of applicants and intelligently match them with the right CEOs and hiring companies based on role, career stage, and fit. I built it in Lovable. It's a prototyping tool for creating mini-apps, and it's changed my perspective on what's possible without a dev team. I'm not an engineer, but I can describe a problem, iterate on a solution, and deploy something functional in a matter of hours. Developing the matching software for The Shortlist would have taken months and a hefty budget. Instead, it took a weekend.

Granola: The Memory Layer The biggest strain of running multiple businesses is the cognitive load. Every conversation, deal, or commitment across hundreds of events and 20+ portfolio companies—if it's not captured, it's gone. Granola is an AI note-taking app that automatically transcribes, summarizes, and analyzes meetings, then enriches live notes with context from the transcript. I use it on every call I take—sponsor discussions, investor check-ins, consulting sessions, partnership negotiations—all of it gets summarized, searchable, and ready for follow-up.

Wispr Flow: I Talk More Than I Type There's a microphone on my desk. I talk to my computer more than I type. In fact, I'm dictating this right now. Wispr Flow is a speech-to-text tool that works in any app, runs four times faster than typing, and includes built-in AI commands and auto-corrections. I use it to draft emails, LinkedIn posts, newsletter sections, and partnership briefs. My first drafts now happen almost entirely out loud. The friction of writing has dropped dramatically since I stopped treating my keyboard as the only input method.

Kondo: Superhuman for LinkedIn Most of my business activity happens in two places: LinkedIn and text messages. On LinkedIn, brand partnerships come together, potential Fibe sponsors reach out, founders apply to The Shortlist, and my content builds the relationships that drive revenue. Kondo—often called "Superhuman for LinkedIn"—helps professionals who use the platform for business development, recruiting, and networking manage high volumes of messages without missing critical opportunities. I can tag conversations, snooze follow-ups, use keyboard shortcuts to batch-process messages, and keep my inbox empty. It's the single biggest workflow upgrade I've made this year.

Raycast: The Command Layer When multitasking across multiple businesses and revenue streams, the cost of context-switching adds up fast. Every time I reach for my mouse, search for an app, or retype something I've already written, there's friction. Friction compounds. Raycast is a keyboard-first launcher that gives users instant access to applications, text snippets, clipboard history, scripts, window management, and more—all via a single shortcut. I use it to jump between tools without touching my mouse, insert saved text blocks for messages I send repeatedly, trigger automations, and execute commands in the apps I use most. Now with built-in AI, I can summon Claude from anywhere on my screen without losing context.

Substack and beehiiv: The Newsletter Layer I run two newsletters for two distinct audiences, so I use two different platforms. Substack is my personal blog and newsletter, where I write about entrepreneurship, events, sobriety, and the ideas I'm wrestling with. The writing environment is clean, the subscriber relationship is direct, and the community Substack has built around serious writers makes it the right home for work that matters to me.

beehiiv powers The Shortlist's newsletter, which goes to founders, operators, and talent teams at startups. It's built differently—more growth-focused, with better analytics and more infrastructure for a publication tied to a business. The two platforms serve different purposes, and I wouldn't swap them.

Framer: Building Brands, Not Just Websites Most of my websites run on Framer, but it's more than a website builder. It's a design-first web platform that lets me create sites that actually look the way I envision—no performance trade-offs, no waiting for a developer to implement every update. My event pages, company sites, and personal brand presence—all Framer. It's also fast enough that I can update a landing page for an event the night before without depending on anyone else.

Endel and Othership: The Operational State None of the tools above matter if your operational state is off. I use Endel for deep work. It generates adaptive soundscapes tailored for focus, sleep, and recovery. When I'm writing, building, or solving a complex problem, Endel runs in the background. It keeps me in flow in a way playlists and lo-fi beats just don't.

Othership is how I disconnect. It's a guided breathwork and meditation app I've invested in and use at the end of the day to unwind. In a work life with no clear boundaries—where you're always simultaneously a founder, content creator, and investor—a deliberate pause isn't a luxury. It's self-preservation.

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