Three years ago, I sat across from a founder who was about to make the same mistake I made with a behind-the-scenes look at how we use portfolio. I told them the truth.
People always ask me how we manage our portfolio of 11 companies. The answer is a disciplined system built around portfolio construction. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
The Reality Nobody Talks About
Most people approach a behind-the-scenes look at how we use portfolio with assumptions that made sense five years ago. The world has moved on. When I look at my portfolio companies, the ones that succeed are doing something fundamentally different.
The first thing to understand is that simplicity beats complexity every time. I've seen this play out across dozens of companies. The pattern is unmistakable.
At RemoteTeam, we learned this the hard way. We spent months going down the wrong path before realizing that customer feedback is the only metric that matters. Once we made the switch, everything changed.
The Counterintuitive Truth
Here's what surprised me most about a behind-the-scenes look at how we use portfolio: the best practitioners do less, not more.
When I was building MovieLaLa, we tried to do everything at once. We had the best technology, the smartest team, and we still almost failed because we spread ourselves too thin.
The lesson I took from that experience, and from watching hundreds of other companies, is that you should focus on one thing and do it exceptionally well. It sounds simple. It's incredibly hard to execute.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to a behind-the-scenes look at how we use portfolio are fundamentally flawed. Not slightly off. Fundamentally flawed.
The root cause is usually one of three things:
- Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
- Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
- Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.
What I Tell Founders
When a founder in my portfolio asks me about a behind-the-scenes look at how we use portfolio, I usually start with three questions:
- What's your timeline? Because the right approach for a company with 6 months of runway is very different from one with 3 years.
- What have you already tried? Most founders have tried something. Understanding what didn't work is often more valuable than knowing what might.
- Who on your team owns this? If the answer is "everyone" or "no one," that's your first problem to solve.
These questions seem simple but they reveal a lot about where a company actually stands.
This connects to broader themes around rolling funds, secondary markets, syndicate investing, portfolio construction that I've been thinking about a lot lately.
Final Thoughts
After two exits, 200+ investments, and more mistakes than I can count, here's what I know for sure about a behind-the-scenes look at how we use portfolio: there are no shortcuts, but there are smarter paths.
The smartest founders I work with treat a behind-the-scenes look at how we use portfolio as a competitive advantage, not a checkbox. They invest in it early, measure it obsessively, and never stop improving.
If you're just getting started with a behind-the-scenes look at how we use portfolio, don't be intimidated. Everyone starts somewhere. The key is to start with the right mindset and the right framework, and then execute like your company depends on it. Because it probably does.
Frequently Asked Questions
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.
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.