Learn to Ask the Hardest Question in Entrepreneurship

Note to reader: Noted entrepreneur Guy Kawasaki observed ““Fundamental in a company, when you cut out all the bullshit, there are only two real functions, you need to make something, and you need to sell it…”

Excerpts

One of the most frustrating things about working with early-stage founders is watching them validate ideas the wrong way. They build wireframes. They schedule Zoom calls. They show friends their mockups and explain features and ask, with wide eyes and hopeful smiles: “What do you think?”

Like clockwork, they get the answer they want to hear.

“Oh wow, this looks really cool.”

“I’d totally use this.”

“I can’t believe something like this doesn’t already exist.”

You know what happens next? Nothing! The startup fails. And it’s because “what do you think?” isn’t a real question. It’s a performance. You’re not testing your startup. You’re testing your ego. And worst of all, you’re gathering data that’s not actually useful in the one place where it matters: market demand.

If You Want the Truth, Ask the Harder Question

The only way to get real, honest, meaningful feedback — the kind that actually helps you build something successful — is to ask a different question.

Ask: Will you buy this?

“Will you buy this?” is a much better question because it turns validation from an opinion into a transaction.

And to be 100% clear here, I don’t mean any of this metaphorically. I mean it literally. Go out and ask someone to give you money. Not just attention. Not just a “like” or a follow or an upvote on Product Hunt. Ask them to make a decision. Put their name on a waitlist. Give you a deposit. Sign a pilot agreement. Do something that costs them something. That’s when people stop lying.

When people have to give something real — whether it’s money or credibility or even a public commitment — that’s when they stop imagining what they might do someday in a world where they have infinite time and zero friction, and they start showing you what they’re actually willing to do right now.

You’re Going to Hate It.

Real founders ask for the sale.

You don’t wait to sell. You sell before you build. You sell before you finish. You sell before it’s perfect. And you do it because selling is how you know whatever you’re building is worth finishing. It’s how you test whether the idea you love is something other people are willing to pay for.

The longer you wait to find that out, the more time and money you’re going to waste building something nobody actually wants. The very first version of your product doesn’t actually need to be a product. It just needs to be a pitch. A landing page. A PDF. A fake screenshot. Whatever. Doesn’t matter. It just needs to be enough to start a conversation and end with a simple ask:

“Do you want to buy this?”

No Excuses. Just Answers.

If the answer is yes… great! Now you know what to build.

If the answer is no… that’s great, too. Now you know what not to build.

And if the answer is “let me think about it” or “this is really cool” or “keep me in the loop” that’s not an answer. That’s a delay, and delays are how startups die.

https://ehandbook.com/learn-to-ask-the-hardest-question-in-entrepreneurship-5bfffe94c6eb