Two of my portfolio companies had opposite approaches to what i wish i knew about series a before losing $2m. The one you'd expect to win didn't.
I’m laying out the surprising lessons I caught after losing money on Series A, so you can avoid my mistakes and get it right the first time.
The Framework That Actually Works
I'm going to share the exact framework I use when evaluating what i wish i knew about series a before losing $2m. It's not complicated, but it requires discipline.
Step 1: customer feedback is the only metric that matters This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: the market doesn't care about your roadmap Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly Nothing works perfectly the first time. The companies in my portfolio that nail what i wish i knew about series a before losing $2m are the ones that treat it as an ongoing process, not a one-time project.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to what i wish i knew about series a before losing $2m 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.
Lessons From the Trenches
I want to share a few specific lessons I've picked up over the years. These aren't theoretical. They come from real companies, real failures, and real successes.
Lesson 1: The best time to start thinking about what i wish i knew about series a before losing $2m was yesterday. The second best time is now. Don't wait until you have the perfect plan.
Lesson 2: Hire for attitude, train for skill. The best what i wish i knew about series a before losing $2m practitioners I've met weren't the most technically gifted. They were the most curious and persistent.
Lesson 3: Your competitors are probably getting this wrong too. That's your opportunity. While everyone else is following the same playbook, you can zig when they zag.
This connects to broader themes around investor relations, Series A, seed funding 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 what i wish i knew about series a before losing $2m: there are no shortcuts, but there are smarter paths.
The smartest founders I work with treat what i wish i knew about series a before losing $2m 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 what i wish i knew about series a before losing $2m, 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
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.
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.