I hit a wall. Hard. It was 2022, and I was juggling a new book launch, managing a portfolio of over 200 angel investments, and trying to be a present husband and father. I was doing what I always did: brute-forcing my way through the workload. 18-hour days were my norm. My calendar looked like a game of Tetris gone horribly wrong. I was burning out, and for the first time, I felt like I was losing control.
That’s when I decided to go all-in on AI. Not just dabbling, but fundamentally rewiring my personal and professional life around it. I was already an investor in some of the biggest names in the space—OpenAI, Anthropic, Scale AI, Hugging Face—so I had a front-row seat to the revolution. But investing in a technology and truly living it are two different things. I was determined to close that gap.
Some of my experiments were a complete disaster. I once tried to automate my investment deal flow with an AI that ended up scheduling a meeting with a pizza delivery guy. True story. But other experiments were life-changing. They didn’t just make me more productive; they gave me back my time and my sanity.
To figure out what was really working, I did what I do best: I looked at the data. My team and I analyzed a cohort of 1000 early-stage startups, many from my own portfolio. We weren't looking at their products. We were looking at their operations. How were the most effective founders using AI to run their companies and their lives? We found five distinct patterns. These aren't about chasing the latest shiny object. These are about building a personal operating system that scales.
1. The "External Brain" Is Real
The most successful founders aren’t just using AI as a better Google. They’re using it to build a second brain. Think about how much time you waste trying to recall a conversation, find a specific document, or connect disparate ideas. It’s a massive cognitive drain. The founders who get this are offloading their entire memory bank to an AI.
I saw this firsthand with a founder in my portfolio who was building a complex deep tech product. She was brilliant, but her team was struggling to keep up with her thought process. She started recording all of her meetings, calls, and even her own voice notes, and feeding them into a centralized AI assistant. Suddenly, her team had a searchable, queryable database of her brain. They could ask, "What was Sarah’s reasoning for the Q3 roadmap change?" and get a perfect summary with links to the source recordings. It was a breakthrough.
I started doing this myself. Every meeting, every call. It felt weird at first, but the payoff was immense. I no longer have to take detailed notes. I can be fully present in the conversation, knowing that my AI is capturing everything. Before a follow-up meeting, I just ask my assistant for a summary of our last conversation and a list of open action items. It’s like having a perfect memory.
How to do it: Don’t just buy a subscription to a fancy AI tool and hope for the best. Start small. Pick one area where you lose a lot of time to recall. Maybe it’s meetings. Start by recording and transcribing them. Then, find a tool that allows you to search and query that information. The goal is to build a trusted, centralized system. Before you spend another dollar on a fancy AI subscription, read this. I tested the top 7 tools, and the winner wasn’t what I expected at all. For me, the combination of a simple transcription service and a private LLM instance has been the most effective.
2. The End of "Maybe"
Scheduling is the bane of every founder’s existence. The endless back-and-forth of "Does Tuesday at 2 PM work?" is a soul-crushing waste of time. The best founders I know have completely eliminated the word "maybe" from their scheduling vocabulary. Their availability is a public fact, managed by an AI.
This goes way beyond simple calendar links. I’m talking about AI agents that have the authority to negotiate, prioritize, and schedule meetings on your behalf, according to a set of rules you define. My own AI assistant has a clear hierarchy: family first, then portfolio companies, then new investment opportunities. It knows I prefer morning meetings and that I need a 30-minute break after every two hours of calls. It can even reschedule non-critical meetings automatically if a higher-priority request comes in.
One of the sharpest founders I’ve backed took this to another level. His AI scheduler is integrated with his CRM. If a high-value lead from a specific industry books a meeting, the AI automatically blocks off extra prep time for him and sends him a briefing document with the lead’s information and recent activity. He walks into every important meeting perfectly prepared, without lifting a finger.
How to do it: This is one area where you need a specialized tool. There are a handful of good AI scheduling assistants on the market. The key is to find one that you can trust with your calendar and your priorities. Spend the time to configure it properly. Give it strict rules. The goal is to get to a place where you never have to manually schedule a meeting again. It’s liberating.
3. The Rise of the "Personal Chief of Staff"
Great leaders delegate. But delegation itself takes time. You have to explain the task, set the context, and manage the follow-up. This is where the concept of an AI-powered "Chief of Staff" comes in. This isn’t just a chatbot. It’s a proactive assistant that understands your goals and can manage complex, multi-step workflows.
After the exit of RemoteTeam to Gusto, I found myself drowning in administrative tasks related to the transition. It was a nightmare of legal documents, financial reports, and HR paperwork. I was on the verge of hiring a full-time human assistant when I decided to try building an AI one first.
I gave it access to my email and calendar, and a clear objective: "Manage the post-acquisition integration process." I defined a series of workflows, from routing documents to the right lawyers to scheduling follow-up meetings with the Gusto team. The AI would triage my inbox, flag the most important emails, draft replies, and even manage my to-do list. It wasn’t perfect, and it required a lot of upfront training, but it saved me at least 20 hours a week. It was the difference between a smooth transition and a chaotic mess.
How to do it: This is the most advanced pattern, and it’s not for everyone. It requires a high degree of trust and a willingness to experiment. Start by identifying a recurring, complex workflow that consumes a lot of your time. It could be anything from managing your sales pipeline to preparing for board meetings. Then, look for tools that offer workflow automation and AI integration. You might need to stitch together a few different services to create your ideal "Chief of Staff." The key is to think in terms of systems, not just tasks.
4. Hyper-Personalization at Scale
AI isn’t just for internal productivity. The smartest companies are using it to create hyper-personalized experiences for their customers. This isn’t about using a person’s first name in an email. It’s about understanding their needs and behavior on a deep level, and tailoring the entire customer journey to them.
Think about my first startup, MovieLaLa. We were trying to build a recommendation engine for movies. The conventional wisdom was to use collaborative filtering, the same technology that Netflix uses. But we were a small startup, and we didn’t have Netflix’s data. We couldn’t compete on that level.
So we went in a different direction. We built an AI that analyzed the emotional DNA of movies. It looked at things like pacing, color palettes, and musical scores. This allowed us to create incredibly specific recommendations. We could tell you, "If you liked the slow-burn tension of The Godfather but wished it had a more modern aesthetic, you’ll love this movie." It was a game-changer for us and a key reason we were eventually acquired by Gfycat.
How to do it: Don’t try to be everything to everyone. Find a niche where you can create a truly unique and personalized experience. Use AI to analyze your customer data and find patterns that your competitors are missing. It could be in your product, your marketing, or your customer support. The goal is to make every customer feel like you built the product just for them.
5. The Self-Correcting System
The final pattern is the most powerful. The best founders aren’t just using AI to execute tasks. They’re using it to learn and improve. They’re building self-correcting systems that get smarter over time.
This is the core philosophy behind my book, "Becoming Top 1%." It’s not about being perfect. It’s about having a system for continuous improvement. AI can be a powerful engine for that system.
I have a weekly ritual where I sit down with my AI assistant and review my week. I ask it questions like: "Where did I spend my time? Did it align with my priorities? Which meetings were a waste of time? What was my most productive day, and why?" The AI gives me a data-driven report on my own performance. It’s not always flattering, but it’s always honest. It shows me where I’m falling short of my own goals and helps me course-correct for the next week.
This is the future of work, and it’s the future of leadership. It’s not about being replaced by AI. It’s about augmenting yourself with AI. It’s about building a system that helps you become the best version of yourself.
The Real Revolution
For years, the promise of AI has been about superhuman intelligence and world-changing breakthroughs. That’s all coming. But the real revolution, the one that’s happening right now, is much more personal. It’s about reclaiming your time, your focus, and your energy.
I didn’t get into this to build a futuristic AI utopia. I got into this because I was drowning. AI was a lifeline. It helped me get back to doing what I love: building companies, working with founders, and solving hard problems. It gave me back my life.
So forget the hype. Forget the doomsday scenarios. Start with a simple question: What’s the most frustrating, time-consuming part of your day? I guarantee you, there’s an AI for that. And it might just change your life. It certainly changed mine.
Frequently Asked Questions
How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.