''' I looked at my calendar and felt a wave of nausea. It was 9 PM on a Tuesday, and I had just finished my 12th meeting of the day. My inbox had 347 unread emails. My to-do list, managed by three different apps, was a cruel joke. I was working constantly, plugging away at my standing desk until my legs ached, but what had I actually accomplished? Jack shit. That was the moment I realized I wasn't being productive. I was just busy. And my so-called "AI productivity" tools were the main culprits.
For years, I've been obsessed with efficiency. As a founder, you have to be. At RemoteTeam, we were a small crew trying to build a global HR platform. Every minute counted. We bootstrapped the company to millions in revenue before Gusto acquired us. I applied the same hustle at MovieLaLa, which we sold to Gfycat. I thought I had my system dialed in. But somewhere along the way, the tools that were supposed to help started to hurt. The promise of automation became a siren song, luring me onto the rocks of complexity and distraction.
The $10,000 Experiment in Chasing Productivity
The market for AI tools is a jungle. Everyone claims their app will "10x your productivity," "automate your workflow," and "give you back your time." It's mostly bullshit. I know because I fell for it. I started trying every new AI email assistant, meeting transcriber, and workflow automator that hit the market. I was a kid in a candy store, but the candy was giving me a stomach ache and a massive bill.
I decided to run a personal experiment. For five months, I would go all-in on the most popular AI tools. I set a budget of $10,000 to pay for subscriptions and premium features. I wanted to see, with hard data, what was actually working and what was just another distraction. I tracked everything: time spent in my inbox, number of meetings, tasks completed, and even my own subjective sense of accomplishment at the end of each day using a simple 1-10 scale in a spreadsheet. The results were not what I expected.
My goal was simple: to find the signal in the noise. This is my brutally honest, data-backed review.
The Good: AI That Actually Works
Let's start with what surprised me. A few tools did deliver on their promises, but not in the way I expected. They didn't magically solve all my problems. Instead, they helped me build better systems by handling specific, narrow tasks exceptionally well.
1. For Email: Superhuman (with a twist)
I know, I know. Superhuman isn't new. But their AI features have quietly gotten very good. The "Triage" function, which automatically sorts my inbox, is a lifesaver. But here's the twist: I don't let it write my emails for me. The AI-generated replies are soulless and generic. They have this weird, overly formal tone that screams "I'm a robot." Instead, I use it to summarize long threads. This is a huge time-saver. I can get the gist of a 20-email chain in 30 seconds. That's a real productivity boost, especially when you're an investor trying to keep up with 200+ portfolio companies.
- Cost: $30/month
- Time Saved: ~45 minutes per day
- Verdict: Worth it, but only if you use it as a summarizer, not a writer.
2. For Meeting Notes: Fireflies.ai
I used to have a human assistant take notes in important meetings. Now, I use Fireflies. It joins my calls, transcribes everything, and creates a searchable record. The accuracy is shockingly good, even with multiple speakers and accents. I can pull quotes, action items, and key decisions without having to re-listen to the entire meeting. This has been a game-changer for my angel investing. I can quickly review my notes from a pitch meeting months later and remember the key details. It’s like having a perfect memory.
- Cost: $18/month (Pro tier)
- Time Saved: ~3-4 hours per week (no more manual note-taking or re-listening)
- Verdict: An absolute must-have for anyone who has more than a few meetings a week.
3. For Focus: Motion
This one was a dark horse. Motion uses AI to automatically schedule your tasks into your calendar, creating a concrete plan for your day. At first, I was skeptical. It felt like giving up control. But it works. By turning my to-do list into a schedule, it forces me to be realistic about what I can accomplish. If a task doesn't fit, it gets pushed. It eliminated the constant, low-level anxiety of a never-ending task list. It also helped me see where my time was really going, which was a wake-up call.
- Cost: $19/month (Individual plan)
- Time Saved: Harder to quantify, but my "sense of accomplishment" score went from an average of 4/10 to 8/10.
- Verdict: Highly recommended for anyone who feels overwhelmed by their to-do list.
The Bad: Tools That Create More Work
Now for the ugly part. The majority of AI tools I tested fell into this category. They promised automation but delivered complexity. They were a solution in search of a problem, a digital form of busywork.
1. The "All-in-One" Workflow Automators
I won't name names, but you've seen them. They promise to connect all your apps and create seamless workflows. The reality is a nightmare of Zapier-like connections that break if you breathe on them too hard. I spent a full weekend trying to set up a "simple" automation to create a Trello card from a labeled Gmail message and then send a Slack notification. It never worked reliably. I spent more time debugging my automations than I would have spent just doing the tasks manually. It's a perfect example of being busy instead of productive. I was "optimizing my workflow," but I wasn't getting anything done.
- Cost: $50-100/month
- Time Saved: Negative. I lost at least 10 hours to this crap.
- Verdict: Avoid at all costs. These tools are a trap for wantrepreneurs who like to play business instead of building one.
2. Most AI Email Assistants
I tested a dozen of these. They all have the same fundamental flaw: they try to sound human, but they fail miserably. The replies are full of corporate jargon and empty pleasantries. "I hope this email finds you well." "Circling back on this." It's nauseating. I got several replies asking if I was using an AI to answer my emails. That's not a good look. It erodes trust. Your personal brand is all you have. Don't let a shitty AI destroy it for the sake of saving a few minutes.
- Cost: Varies, but many are in the $20-40/month range.
- Time Saved: None. I had to re-write almost every AI-generated draft.
- Verdict: A dangerous gimmick. Write your own emails. It's not that hard.
The Truly Dangerous: AI That Kills Your Creativity
There's another category of AI tools that's even more insidious than the ones that just waste your time. These are the tools that slowly, subtly, kill your ability to think for yourself. I'm talking about the AI-powered "idea generators" and "content creators."
I experimented with a few of these for blog post ideas and even to draft sections of my book, "Becoming Top 1%". The output was... fine. It was grammatically correct. It was logically structured. But it had no soul. It was a remix of everything that has already been said. There was no original thought, no unique insight, no spark of creativity. It was the intellectual equivalent of a beige wall.
The danger here is that it's easy to become reliant on these tools. It's tempting to let the AI do the "hard work" of thinking. But thinking is the work. As a founder and an investor, my job is to have a unique perspective, to see things that others don't. If I outsource my thinking to an AI, I'm just another commodity. I'm replaceable.
My Framework for AI-Powered Productivity
After five months and over $10,000, I've come to a few conclusions. Here's my framework for using AI without falling into the productivity trap:
- Be the Master, Not the Servant: AI should be a tool, not a crutch. Use it to augment your own abilities, not replace them. Use it for summaries, transcriptions, and data analysis—tasks that are about processing information, not generating ideas. The moment you let an AI think for you, you've lost.
- One Thing Well: The best AI tools do one thing exceptionally well. Fireflies transcribes meetings. Superhuman sorts email. Motion schedules your tasks. The all-in-one solutions are a mess because they try to do too much and end up doing nothing well. Find single-purpose tools that solve a specific, painful problem.
- Measure the Outcome, Not the Activity: Don't get seduced by the idea of "automation." Measure the actual outcome. Is this tool saving you time? Is it helping you make better decisions? Is it making you more money? Is it reducing your stress? If you can't point to a concrete, positive outcome, ditch it. The goal is not to be automated; the goal is to be effective.
- Protect Your Voice: Your personal style is a competitive advantage. It's what makes people want to work with you, invest in you, and follow you. Don't let an AI water it down with generic, soulless prose. Whether you're writing an email, a blog post, or a tweet, make sure it sounds like you. Authenticity is magnetic.
I'm not an AI skeptic. I'm an investor in some of the biggest names in the space, like Anthropic, OpenAI, Scale AI, and Hugging Face. I believe AI will change the world. But right now, we're in the hype phase. It's like the early days of the internet, with a lot of noise and a lot of scams. We need to be smart and discerning about how we use these new powers.
I've since canceled most of my AI subscriptions. My stack is lean and effective. I spend less time managing my tools and more time building my businesses and helping my portfolio companies. I'm less busy, but I'm more productive. I've rediscovered the joy of deep work and original thought. And that's a feeling that no AI can replicate. '''
Frequently Asked Questions
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
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.
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.