I've been wrong about the brutal reality of series a in 2026 more times than I'd like to admit. But the last mistake taught me something I can't unlearn.
Everyone says Series A is easy. They're lying. I'm breaking down the brutal reality and how to actually win.
What I've Learned From 125 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with the brutal reality of series a in 2026.
The biggest misconception is that you need to you need to move fast and break things. That's backwards. The companies that win are the ones that most founders overthink this and underspend on execution.
I remember sitting with the Anthropic team early on and discussing how they thought about the brutal reality of series a in 2026. Their approach was counterintuitive but brilliant.
The Reality Nobody Talks About
Most people approach the brutal reality of series a in 2026 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 the best solutions are often the simplest ones. 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.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to the brutal reality of series a in 2026 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.
The AI Angle
I can't talk about the brutal reality of series a in 2026 in 2026 without mentioning AI. As someone who's invested in Anthropic, OpenAI, Scale AI, and Hugging Face, I have a front-row seat to how AI is transforming this space.
The short version: AI makes good practitioners better and bad practitioners worse. It's an amplifier, not a replacement.
I've seen companies use AI to 10x their the brutal reality of series a in 2026 capabilities. I've also seen companies waste millions on AI solutions that solved the wrong problem. The difference comes down to understanding what you're actually trying to achieve.
This connects to broader themes around revenue-based financing, seed funding, investor relations, convertible notes that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But here's the thing about the brutal reality of series a in 2026: you don't need to get everything right on day one. You just need to get started and keep improving.
The founders in my portfolio who excel at the brutal reality of series a in 2026 share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
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.
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.