Five weeks before demo day, I handed Nir Zavaro, The Business Storyteller, my pitch during a Boxsy Office Hours session and asked him to roast it. I thought I had a pretty solid five minutes to explain Boxsy, but quickly I discovered Nir had other thoughts.

Within minutes, he was pointing out things I hadn't even noticed. I was repeating myself, saving my founder experience for too late in the pitch, and talking about our price before I'd properly explained the problem we were solving. In other words, I was trying to tell the whole story without giving the audience the right reasons to care.

The good news from my roast? I cut around 40 seconds from my pitch without changing a single idea. The exercise reminded me that a better pitch isn't about cramming more in. It's about knowing what deserves to be there in the first place.

Here are three lessons from Nir's feedback that I'm taking into my next investor meeting.

Make The First 30 Seconds Count

Nir's advice was simple: the first 30 seconds should land one clear claim, and everything that follows should help prove it. Instead of taking time to re-introduce myself, I should have used those most valuable seconds to captivate the audience and give them a reason to care.

As founders, we want investors to understand the product, the market, the traction, and everything that makes the company special, but trying to explain it all at once can make the main point harder to remember.

Try this: Write down the one sentence you want an investor to remember. If your opening doesn't communicate that idea, start there.

Lead With Credibility

Investors need to understand why you’re the right person to build your business early in the pitch. I made the mistake of saving my ten years of experience in the startup ecosystem until near the end, rather than using it to establish credibility from the beginning.

Your background gives investors context for your perspective and shows them what led you to build this business. It helps them understand why you're equipped to solve the problem, rather than simply hearing about your idea.

Try this: Identify the experience or insight that makes you qualified to solve this problem. Introduce it early in your pitch to establish credibility, then build on that foundation as you explain the problem, your solution, and why it matters.

Establish Value Before Introducing Price

Nir also pointed out that I introduced Boxsy’s monthly price before giving the audience enough context to understand its value. Price is easier to evaluate when people first understand what the alternative would cost. Establishing that comparison helps investors see the value of the solution before judging its price.

The same principle applies throughout your pitch. Numbers, features, and product benefits are more compelling when your audience understands why they matter. Before presenting your solution, establish the problem, what it costs to leave it unsolved, and why solving it is worth investing in.

Try this: Review where pricing first appears in your pitch. Have you clearly communicated the problem, the cost of doing nothing, and the value of your solution before revealing the price? If not, rethink the order.

A stronger pitch starts with a clearer story

A five-minute pitch is only about 500–650 words. That sounds like plenty until you try to explain your business, why it matters, and why someone should invest in it.

During this Boxsy Office Hours session, I asked Nir Zavaro, author of F*ck the Sldies, to roast my pitch, and his feedback made me realize I was trying to say too much, and in doing so, I was making my main points harder to land.

Here are my key takeaways from the experience:

Get to the point sooner. Your opening should give investors a clear reason to pay attention. You can’t cover everything right away, so lead with what matters most.
Explain the problem before the solution. Investors need to understand why a problem is worth solving before they can appreciate what you’ve built or what it costs.
Bring your experience into the story early. Give investors a reason to believe you’re the right person to build this business, rather than saving that context for the end.
Cut the repetition. Nir counted the word “what” 13 times in my draft. It was a pretty clear sign that I was using more words than I needed to get my point across.

You don't need to fit everything into five minutes, but you need to make sure investors understand the things that matter. Thank you to Nir and the Stukk team for the honest feedback. Sometimes, having someone challenge the way you explain your business is exactly what you need.

Getting ready to raise? Book 20 minutes with me to talk through your pitch, get another perspective on your story, or discuss how you’re approaching your raise.