Over the past few months, I've spent less time sketching amusing analogies (usually involving my kids) and more time in the trenches with early-stage founders. Whether it’s one-on-one sessions or time with the incredible teams in the accelerators I work with, I keep hearing the same handful of questions repeat themselves.

There’s a whole universe of essential questions that founders face but might hesitate to ask out loud. They feel too basic, too vulnerable, not important enough, or just too scary to admit you haven't figured out yet.

So, while the analogies will return when the mood strikes, I’m getting some structure going. This is the first of a regular summary—a kind of unfiltered FAQ—based on the roughly 90 questions I hear most often. It's part of an effort to connect with more early-stage builders, learn from their experiences, and offer help where I can.

Here are three key questions from the past week:

Q: I have three startup ideas. How do I pick the right one?

A: You don’t pick the right idea—you pick the idea you can’t stop thinking about.

I’ve been obsessed with dozens of startup ideas over the years. Some made perfect business sense. Some had massive TAM or slick monetization. But only a handful kept me up at night, sketching business models on napkins at 11 PM, cornering friends at gatherings, and repeatedly reimagining the problem I wanted to solve.

The “right idea” isn’t necessarily the one with the best pitch deck. It’s the one that scratches an itch you can’t ignore. It’s the problem you’ve lived, the gap you can’t unsee—no matter what else is on your mind.

Here’s a framework that’s worked for me:

  1. Spend one week deeply focused on each idea.

  2. Build a basic landing page (it can be fake, just to clarify the value prop).

  3. Talk to 10 potential customers.

  4. Pay attention to which conversations energize you and which feel like homework.

The idea you’re still excited about on Friday afternoon? That’s your signal. If you’re having this debate with yourself, chances are, so is every founder out there. You’re not alone—and obsessing a little is a good sign.

Q: What if my idea has already been done?

A: Good. That means there's a market.

I confess—when we started Create Your Couch (which eventually became Alara), there were already dozens of e-commerce furniture players. Bigger ones. Better-funded ones. Ones with brand recognition I could only dream of.

But here's what I learned: execution beats originality every single time.

Your competitors validate that the problem is real and people will pay to solve it. What they don't tell you is whether your specific approach will resonate with your specific customer.

The question isn't "Has this been done?" It's "Can I do this better for a specific segment?"

Maybe your version is:

  • Faster to implement

  • Designed for a different geography

  • Built for a customer segment others ignore

  • Simpler (trust me, simplicity wins)

Stop worrying about the crowded market. Worry about whether you understand your customer better than anyone else does.

Q: How do I know if I'm solving a real problem?

A: Ask 20 people. If 15 of them interrupt you mid-sentence to tell you their version of the pain, you're onto something.

Real problems don't need explanation. They trigger recognition.

When I was validating the problem ComeBy solved, I'd describe the data fragmentation challenge retailers faced. The ones who had the problem? They'd finish my sentences. They'd pull out their phones to show me their broken dashboards. They'd introduce me to their teams.

The ones who didn't have the problem? Polite nods. "Interesting." "Let me think about it."

You're not looking for "that sounds cool." You're looking for "where have you been my whole life?"

Here's your validation checklist:

  1. Do they describe the problem in vivid detail unprompted?

  2. Have they already tried (and failed) to solve it themselves?

  3. Do they ask when you're launching?

  4. Do they offer to pay you before you ask?

If the answer to 3 out of 4 is yes, you've got a real problem.

If you know an early stage founder who is stuck on something? I'd love to have a chat!

I'm offering 30-minute, no-BS sessions for early-stage founders needing clarity or fresh perspective. The idea is for them to bring their biggest blocker — and hopefully leave with practical next steps.

Happy to help find synergies in my network too.

Book a slot: https://lnkd.in/gVU35F77