My MBA was a joke. Okay, not a complete joke, but it taught me more about PowerPoint than about people. The real education came when I was in the trenches, building a learning platform that, against all odds, ended up with 50,000 students. The all-nighters, the panicked bug-fixing sessions, the brutal-but-honest user feedback—that was my real MBA. I’m sharing the seven biggest lessons from that chaotic journey. This is the stuff they don’t teach you in a lecture hall.
1. Your Algorithm Isn't as Smart as You Think
I was obsessed with our personalization algorithm. I thought we could build this all-knowing AI that would magically create the perfect learning path for every student. We spent months, and a ton of money, building a system that tracked every single click, every answer, every second of video watched. I was convinced we were building something revolutionary.
We weren't. We were building a glorified spreadsheet.
It hit me when I was reading a user feedback email. A student was struggling with a concept, and our algorithm just kept feeding her the same type of content, over and over again. It was like trying to teach someone to swim by throwing them in the deep end and yelling "kick harder!". Our algorithm knew what she was getting wrong, but it had no idea why. It didn't understand her frustration, her learning style, or the fact that maybe she just needed a different explanation.
That's when we ripped everything out and started again. We started talking to our users. Real, live conversations. We learned about their goals, their anxieties, and what actually motivated them. We added a simple feature that let students set their own weekly goals. It wasn't a fancy AI, but it worked. Engagement shot up because suddenly, they were in control. They had a reason to come back.
2. Engagement is Not a Game
I confess, I fell for the gamification hype. I was convinced that if we just added enough points, badges, and leaderboards, students would be hooked. We spent a ridiculous amount of time and money building this elaborate system. It was a ghost town.
Nobody cared. They weren't there to play a game. They were there to learn. They wanted to feel like they were making progress, that their time was well spent. We had to completely scrap our idea of engagement.
We started focusing on creating a state of flow. We broke down huge, intimidating topics into bite-sized, manageable lessons. We built a simple, visual progress bar that showed them how far they'd come. It sounds almost stupidly simple, but seeing that bar move, seeing that they were 10% closer to their goal, was more motivating than any badge we could have designed. It was tangible. It was real.
3. The Ethics of AI in Education Will Keep You Up at Night
Building an AI product for education is a heavy responsibility. You're not just trying to get more clicks or sell more widgets. You are, in a very real way, shaping how people think and learn. That's a thought that should scare you a little.
We had endless debates about student data. We knew we could use it to create a more personalized experience, but at what cost? We decided to take a risk and give students complete control over their data. They could download it, delete it, or tell us to stop tracking them at any time. Our investors thought we were crazy, but it was the only way we could sleep at night.
And then there's bias. AI is a mirror, and if the data you train it on is biased, your AI will be too. We had to constantly audit our algorithms, looking for hidden biases that could disadvantage certain students. It's a never-ending process, and it's one of the most important things you'll do.
4. Scaling is a People Problem, Not a Tech Problem
As a tech founder, it's easy to get lost in the weeds of scaling. You're worried about server loads, database queries, and whether your whole system is going to crash when you hit your next thousand users. But the real challenge of scaling isn't technical. It's human.
It's about scaling your customer support without turning into a faceless corporation. It's about scaling your team without losing the culture that made you great in the first place. It's about not losing your soul in the pursuit of growth.
We learned this the hard way. We were so focused on the tech that we let everything else slide. Our support queues were a disaster, our team was burning out, and the office felt more like a morgue than a startup. We had to hit the brakes, hard, and fix the human side of the business. We hired more support staff, we implemented a strict "no work on weekends" policy, and we started having regular all-hands meetings to make sure everyone felt connected to the mission.
5. Your Gut is Your Most Important KPI
You will be drowning in data. User engagement, churn rates, conversion funnels—you'll have a dashboard for everything. And it's easy to become a slave to the numbers. To let the data dictate your every move.
But data can only tell you what's happening. It can't tell you why. It can't tell you what to do next. That's what your gut is for.
Your gut is that little voice, that intuition, that tells you when something feels off, even when the numbers look good. It's your most valuable asset as a founder, and you need to learn to trust it.
I remember a time when all the data was telling us to double down on video content. But my gut was screaming that students were bored of passively watching videos. They wanted to do something. So we built a series of interactive simulations. It was a huge bet, and it went against all the data we had. But it was a massive success. Sometimes, you have to have the courage to bet on your own intuition.
6. The MVP is a Lie
The "minimum viable product." It's the holy grail of Silicon Valley. Launch fast, get feedback, iterate. It sounds so simple. It's also a lie.
In education, you don't get a second chance to make a first impression. Students are busy. They're juggling classes, jobs, and a million other things. They don't have time for your buggy, half-baked product. Your MVP can't just be "viable." It has to be valuable. From day one.
Our first MVP was a train wreck. It was slow, confusing, and barely worked. We were lucky to get a second chance. If I could do it all over again, I would have waited. I would have polished it until it shined. I would have launched a product that I was proud of, not just a product that was "done."
7. Your Team is the Only Feature That Matters
I've saved the most important lesson for last. You can have the most brilliant idea, the most sophisticated AI, the most beautiful design. But if you don't have the right team, you have nothing.
I was incredibly lucky. I was surrounded by people who were smarter than me, who challenged me, and who believed in our mission even when I was ready to give up. They were the ones who stayed late to fix a bug, who came up with the crazy ideas that ended up being brilliant, and who supported each other through the endless rollercoaster of startup life.
If you're a founder, your number one job is to build a great team. Hire people who are passionate, who are resilient, and who are just plain good human beings. Because in the end, your team isn't just a part of your company. It is your company.
The Takeaway
Building a company is the hardest thing I've ever done. It's a relentless, soul-crushing, and utterly exhilarating journey. There will be days when you want to curl up in a ball and cry. But if you can find a problem you care about, and a team you believe in, you can build something that matters.
I'd love to hear your own stories from the trenches. What are the lessons you've learned the hard way? Leave a comment below.
I want to add one more thing. It’s a lesson that took me a while to learn, but it’s probably the most important one of all. You are not your user. It sounds obvious, but it’s a trap that so many founders fall into. You get so wrapped up in your own vision, your own ideas, that you forget who you’re building for. I remember we were about to launch a new feature that I was incredibly excited about. I had spent weeks designing it, and I was convinced it was going to be a huge hit. The night before we were supposed to launch, one of our junior engineers came to me and said, “I don’t think anyone is going to use this.” I was furious. I almost fired him on the spot. But then I took a step back and asked him why. He explained that the feature was too complicated, that it didn’t solve a real problem for our users. He was right. We ended up scrapping the feature and going back to the drawing board. That engineer saved us from a huge mistake. And he taught me a valuable lesson: you have to be willing to kill your darlings. You have to be willing to admit when you’re wrong. And you have to be willing to listen to your team, even when they’re telling you something you don’t want to hear.
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.
How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.
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.
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.