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1. Your Data Is a Mess (And It's Your Fault)
Everyone loves to blame the tools. Or the engineers. Or the data scientists. But the buck stops with the founder. At MovieLaLa, my first startup, we had data coming from a dozen different sources. User activity, social media, ad spend, you name it. It was a tangled web of APIs and CSVs. We spent more time trying to stitch it all together than actually analyzing it. I thought a new tool would solve the problem. So I bought one. And another. And another. Nothing worked.
The problem wasn't the tools. It was me. I hadn't established a clear data strategy from day one. I hadn't defined what data we needed, how we would collect it, and how we would store it. It was a free-for-all. And it cost us dearly. We missed key insights that could have saved us months of wasted effort.
Here’s a hard pill to swallow: if your data is a mess, it’s because you haven’t made it a priority. You can’t just delegate data. You have to own it.
2. AI Won't Magically Clean Your Data
There's a dangerous myth circulating in Silicon Valley. It's the idea that you can just throw a bunch of messy data at an AI and it will magically spit out brilliant insights. That's not just wrong, it's lazy. And it's a recipe for disaster.
I saw this firsthand with one of my portfolio companies. They had a massive dataset of customer interactions. They were convinced that if they just fed it into a machine learning model, they would unlock the secrets to reducing churn. They spent six months and a small fortune on a team of data scientists. The result? A model that was 99% accurate at predicting... absolutely nothing useful. The data was so noisy and inconsistent that the model couldn't find any meaningful patterns.
AI is a powerful tool, but it's not a mind reader. It can't fix your data for you. It can't tell you what's important and what's not. That's your job. You have to do the hard work of cleaning, structuring, and labeling your data before you can even think about applying AI.
3. Your Dashboards Are Lying to You
I used to love dashboards. I had them for everything. A big screen in the office cycling through charts and graphs. It felt like I had my finger on the pulse of the business. But I was just staring at a bunch of vanity metrics. Our user numbers were going up, but so was our churn. Our engagement was high, but our revenue was flat. The dashboards were telling me a story, but it was a work of fiction.
The problem with dashboards is that they only show you what you tell them to show you. They don't have context. They don't understand the nuances of your business. And they can be easily manipulated to paint a rosy picture. I've seen founders who are so obsessed with their dashboards that they lose touch with reality. They're so focused on the numbers that they forget about the people behind them.
I'm not saying you should ditch your dashboards altogether. But you need to be smart about how you use them. Don't just track the easy stuff. Track the things that really matter. And don't be afraid to question the data. If something looks too good to be true, it probably is.
4. You're Drowning in Data, But Starving for Insight
We live in an age of data abundance. We have more data at our fingertips than ever before. But more data doesn't necessarily mean more insight. In fact, it often means the opposite. We're so overwhelmed with data that we can't see the forest for the trees.
I've seen this happen time and time again. Startups that are so focused on collecting data that they forget to actually use it. They have terabytes of data sitting in a data warehouse, gathering digital dust. They're so afraid of missing something that they end up missing everything.
At RemoteTeam, we had a rule: for every new metric we tracked, we had to get rid of one. It forced us to be ruthless about what we measured. It forced us to focus on the things that really mattered. And it made our data much more manageable and actionable.
Don't be a data hoarder. Be a data minimalist. Focus on the few key metrics that will actually drive your business forward. And don't be afraid to let go of the rest.
5. Your Team Is Flying Blind
I once walked into the office of a portfolio company and saw a huge screen displaying a real-time sales leaderboard. The founder was proud. "We're a data-driven company," he told me. "Everyone knows their numbers." But when I talked to the sales team, I found out they had no idea what the numbers meant. They were so focused on hitting their daily quota that they weren't thinking about the bigger picture. They were just a bunch of individual contributors, not a team.
It's not enough for you to be data-literate. Your entire team needs to be on the same page. They need to understand what the data means, how it's being collected, and how it's being used to make decisions. If they don't, you're just creating a culture of fear and anxiety. People will be so afraid of missing their targets that they'll do whatever it takes to hit them, even if it's not in the best interest of the company.
At RemoteTeam, we had a weekly all-hands meeting where we went over the numbers. But we didn't just show them the charts and graphs. We told them the stories behind the numbers. We talked about what went well, what went wrong, and what we were going to do differently next week. It wasn't about holding people accountable; it was about learning and growing together.
6. You're Chasing Vanity Metrics
Likes, followers, page views... these are the empty calories of the data world. They make you feel good, but they don't actually move the needle. I've seen so many founders who are obsessed with these vanity metrics. They'll spend a fortune on marketing campaigns to boost their numbers, but they have no idea how to turn those numbers into actual revenue.
At MovieLaLa, we made this mistake in the early days. We were so focused on getting to a million users that we didn't pay enough attention to whether those users were actually engaged. We had a huge number of sign-ups, but our retention was terrible. People would download the app, use it once, and then never come back. We were pouring water into a leaky bucket.
It wasn't until we started focusing on the right metrics—things like daily active users, session length, and user-generated content—that we started to see real growth. We realized that it's not about how many users you have; it's about how many of them are actually getting value out of your product.
Don't be seduced by vanity metrics. They're a distraction. Focus on the metrics that are directly tied to your business goals. And don't be afraid to ignore the rest.
7. You're Ignoring the Most Important Data Source: Your Customers
I saved the most important truth for last. In our quest for data-driven enlightenment, we often forget about the most valuable data source of all: our customers. We get so caught up in the numbers that we forget to actually talk to the people who are using our products.
I learned this lesson the hard way at RemoteTeam. We were struggling with churn. We had all the data in the world, but we couldn't figure out why people were leaving. We tried everything. We tweaked the product, we changed the pricing, we ran A/B tests. Nothing worked. Finally, out of desperation, I picked up the phone and started calling our churned customers. And you know what I found out? The problem had nothing to do with the product. It was a simple onboarding issue. People were confused about how to get started. It was a problem that no amount of data analysis could have ever solved.
Your customers are a goldmine of information. They can tell you what they love about your product, what they hate about it, and what they wish it could do. They can give you insights that you'll never find in a dashboard. So get out of the office. Talk to your customers. Listen to their stories. And don't be afraid to ask for their feedback. It's the most valuable data you'll ever get.
The Bottom Line
AI data isn't a silver bullet. It's a tool. And like any tool, it can be used for good or for evil. It can be used to build a better business, or it can be used to create a culture of fear and anxiety. The choice is yours.
After years of wrestling with data, here’s my final take: Stop chasing the fantasy of a perfect, all-knowing AI. It doesn’t exist. The real magic happens when you combine the power of AI with the wisdom of human intuition. When you use data to inform your decisions, not to make them for you. And when you never, ever lose sight of the people you're trying to serve.
So, what are you going to do? Are you going to keep drowning in data, or are you going to start swimming towards insight? The answer will determine the future of your business.
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.
Are these recommendations still relevant in 2026?
Absolutely. While specific tools and tactics change, the underlying principles remain consistent. I update my thinking regularly based on what I'm seeing in the market and across my portfolio companies.
Can I implement all of these at once?
I'd strongly recommend against it. Pick the 2-3 items that resonate most with your current situation and focus there. Trying to do everything simultaneously is a recipe for doing nothing well.
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.