I used to wear my 80-hour workweeks like a badge of honor. I was the classic Silicon Valley founder, fueled by caffeine and a deep-seated fear of slowing down. I thought I was being productive, but I was just busy. Drowning in a sea of tasks, meeting alerts, and a never-ending inbox. The irony? I was building a company, RemoteTeam, meant to make work more efficient. It was a classic case of the cobbler's children having no shoes.
After we were acquired by Gusto, I had a moment to breathe. And I took a hard look at my own productivity, or lack thereof. The market was exploding with AI-powered scheduling and workflow tools, all promising to be the magic bullet. So I did what any self-respecting engineer and investor would do: I ran an experiment. For 6 months, I spent over $5000 of my own money testing every major AI scheduling and automation tool I could get my hands on. I wanted to see what was hype and what was real. This is my brutally honest, data-backed review of what I learned. It’s not what I expected.
1. Your Calendar Isn't a To-Do List
This was my first big mistake. I was cramming my calendar with every single task, from "review Q3 marketing deck" to "pick up dry cleaning." My AI scheduler was dutifully finding slots for everything, but my days became a rigid, suffocating game of Tetris. If one thing went long, the whole day collapsed.
I learned to separate the what from the when. My to-do list app is for the what. My calendar is for the when, and only for things that require a specific, immovable block of time. This seems obvious, but in practice, it’s a game-changer. My AI scheduler is now tasked with finding time for meetings and deep work blocks, not for managing my entire life. It’s a subtle shift, but it returned a sense of agency to my days.
2. Automate the Boring, Not the Important
When I first started playing with automation tools, I went crazy. I tried to automate everything—email responses, social media posts, even parts of my investment analysis. It was a disaster. I almost missed a great seed-stage deal because an automated email filter sent a founder’s pitch to the wrong folder. A cold, automated "Thanks for your interest" is no way to treat a potential partner.
My new rule is simple: if a task requires nuance, empathy, or a personal touch, a human does it. That’s me. I automate the truly mundane, the copy-paste work. Things like generating weekly reports from our analytics dashboards, or sending reminders for team meetings. At RemoteTeam, we automated the process of generating payroll reports, which saved us hours of manual data entry. But I never automated the conversations with my team about their performance or their career goals. Some things are just too important to hand over to a script.
3. The "Best" Tool is the One You Actually Use
The internet is full of articles proclaiming the "best" AI productivity tool. I tested them all. And you know what I found? The fanciest, most feature-rich tool is often the one that gets abandoned after a week. It’s too complex, too clunky, too much of a hassle to set up.
I ended up sticking with a surprisingly simple stack. It’s not the most powerful, but it’s the one that fits seamlessly into my existing workflow. I’m not going to name names, because the specific tools don’t matter. What matters is the principle: find the tools that feel intuitive to you. The ones that don’t require you to change your entire way of working. A 10% improvement you stick with is infinitely better than a 100% improvement you abandon.
4. Your Gut is a Data Point, Too
As an angel investor in over 200 companies, including some big names in AI like Anthropic and OpenAI, I live and breathe data. I love a good spreadsheet. But I’ve learned that data can only tell you part of the story. When it comes to making big decisions, whether it’s investing in a startup or choosing a strategic direction for a product, you can’t ignore your gut.
I once passed on a company because their metrics didn’t look great. The user growth was slow, the churn was high. But I had a good feeling about the founder. He was smart, passionate, and had a unique insight into the market. I let the data overrule my intuition. That company went on to raise a massive Series A and is now a major player in their space. I missed out. My gut was telling me something the numbers weren’t. Now, I treat my intuition as a valid data point in my decision-making process.
5. AI Can't Fix a Broken Culture
I’ve seen founders try to use AI to solve all their problems. Low team morale? Let’s get an AI-powered feedback tool. Missed deadlines? Let’s get an AI project manager. It never works. Technology is an amplifier. It makes a good team better and a bad team worse.
If your team culture is built on a lack of trust, poor communication, and unclear goals, no amount of AI will fix it. At MovieLaLa, my second company, we had a very open and collaborative culture. When we introduced new tools, they were adopted quickly and effectively because the team was already working well together. We used tools to enhance our existing workflows, not to create them from scratch. Focus on building a strong, healthy culture first. Then, and only then, can you start thinking about how AI can help.
6. I Was More Productive When I Worked Less
This was the most counterintuitive lesson of all. For years, I believed that more hours equaled more output. I was wrong. When I was working 80-hour weeks, I was constantly exhausted, unfocused, and making stupid mistakes. I was busy, but not productive.
During my 6-month experiment, I forced myself to work a strict 40-hour week. I was ruthless about cutting out anything that wasn’t essential. I declined meetings, ignored emails, and delegated tasks. And a funny thing happened: I got more done. A lot more. The constraints forced me to be more focused and intentional with my time. I had more energy, my thinking was clearer, and my decisions were better. Now, I’m a firm believer in the power of constraints. Less is often more.
7. The Real Cost of AI Isn't the Subscription Fee
Everyone focuses on the monthly cost of these AI tools. $10 here, $20 there. It adds up, but it’s not the real cost. The real cost is the time and energy it takes to implement, learn, and maintain these tools. It’s the cost of switching from one tool to another. It’s the cost of the mistakes you make when you’re trying to automate something and it goes wrong.
I spent over $5000 on subscription fees, but I probably spent ten times that in terms of my own time. Was it worth it? For me, yes. It was an investment in my own education. But for most people, I’d recommend a different approach. Start small. Pick one or two tools that solve a real, painful problem. Master them. Then, and only then, should you start thinking about adding more to your stack.
8. AI is a Powerful Intern, Not a CEO
There’s a lot of fear and hype around AI taking over the world. I’m not worried. At least, not yet. In my experience, AI is incredibly powerful for specific, well-defined tasks. It can write code, analyze data, and generate reports faster and more accurately than any human. But it can’t think strategically. It can’t build relationships. It can’t inspire a team.
I think of AI as a team of brilliant, tireless interns. They can do all the grunt work, freeing me up to focus on the things that really matter. The things that require my unique experience, creativity, and judgment. The CEO of your life and your business is still you. Don’t abdicate that responsibility.
9. The Most Important Skill in the AI Age is Asking the Right Questions
I used to think the most important skill was having the right answers. Now, I believe it’s asking the right questions. The quality of your output from an AI is directly proportional to the quality of your input. Vague questions get vague answers. Specific, well-framed questions get specific, valuable answers.
This applies to everything, from using a large language model to brainstorm ideas to querying your analytics data. I spend a lot more time now thinking about the questions I’m asking. What am I really trying to understand? What’s the most important variable? What are the hidden assumptions in my query? It’s a new kind of intellectual discipline, and I believe it’s the one that will separate the winners from the losers in the age of AI.
10. I'm Still Learning
This is probably the most important lesson of all. The world of AI is moving at an incredible pace. The tools and techniques that are cutting-edge today will be obsolete tomorrow. I don’t have all the answers. Nobody does. I’m constantly experimenting, learning, and adapting my own workflows.
Building an effective, AI-powered workflow isn’t a one-time project. It’s a continuous process of refinement and improvement. It’s a journey, not a destination. And for me, that’s the most exciting part. The future isn’t about being replaced by AI. It’s about partnering with AI to become a better, more effective version of ourselves. And I’m just getting started.
Frequently Asked Questions
How do I know which items apply to my situation?
Start by honestly assessing where your biggest bottleneck is right now. The items that address that specific constraint will give you the highest return on your time and energy.
Which item on this list has the highest impact?
It depends on your stage and context, but in my experience, the items near the top of the list tend to have the broadest applicability. That said, sometimes the less obvious items create the biggest breakthroughs for specific situations.
How were these items selected?
Each item on this list comes from direct experience, either from building my own companies or from patterns I've observed across the 200+ startups I've invested in. I prioritize practical, actionable items over theoretical concepts.