The Questions I Wish I Had Asked Before My First Investments
When I first started investing in early-stage companies, I’ll be honest — my process was pretty simple.
Sometimes it was almost back-of-a-napkin simple.
I’d meet a founder, get a sense of who they were, hear the idea, and if it felt right, I’d move forward. In many cases it worked out. The people executing the idea mattered more than anything else, and trusting the team often proved to be the right instinct.
But over time, after sitting through more pitches and seeing more companies develop, I realized something important.
There are better questions to ask.
And not just better questions — better ways to interpret the answers.
The Real Test Isn’t the Pitch
Most founders can deliver a polished pitch. Slides are clean. Projections look great. The market opportunity is massive.
That part is expected.
What matters more is what happens after the presentation when the conversation starts.
That’s where real diligence happens.
For example, I like to ask founders what has changed since their last update. If a company sends quarterly reports, I want to know:
What did you say would happen last quarter?
What actually happened?
What went right?
What went wrong?
Those answers tell you far more than the original pitch.
Businesses rarely move in a straight line. Progress is messy. A founder who can clearly explain the gap between expectations and reality is usually someone who understands their business.
Watch for the Evasive Answer
One of the biggest lessons I’ve learned is this:
The way someone answers a question is often more important than the answer itself.
If someone says, “I don’t know, but I’ll find out,” that’s fine.
If they say, “We’re still working through that,” that’s also fine.
But when someone starts dancing around a question, that’s usually telling you something.
Over time you start noticing patterns. Certain questions consistently reveal weak spots in a business model or execution plan.
Those patterns come from experience — from listening to dozens of founders explain their strategy and comparing it to what actually happens later.
Small Investments Can Be Great Teachers
Interestingly, some of the best learning happens with smaller investments.
When you invest $5,000 or $10,000 into a startup, the financial risk may be smaller, but the learning opportunity is huge. You get access to updates, investor calls, and the ongoing story of the company.
Watching those updates quarter after quarter teaches you how businesses actually grow.
You begin to see:
Which metrics matter
Which founders communicate clearly
Which companies adapt when things change
Over time, that experience sharpens your instincts for larger investments.
Investing Is a Skill You Develop
People sometimes assume investing is about spotting the perfect idea.
In reality, it’s much more about developing judgment.
You build that judgment by asking questions, listening carefully, and comparing what people say with what eventually happens.
Every investment teaches you something.
If you pay attention, the lessons compound.