Current in Entrepreneurship Blog

You just finished your first pitch deck.

You think it’s strong. But you can’t shake the feeling that something might be off.

Here’s the uncomfortable truth: founders are terrible judges of their own pitch decks. I was no exception.

When I completed my first pitch as an Entrepreneur in Residence, I proudly presented it to a venture partner I was working with. When I finished, he laughed and said:

“Everyone’s first pitch sucks.”

He was right.

I don’t want that to happen to you.

This post covers:

1. Why founders can’t accurately judge their own pitch

   1. Three stress tests every pitch must pass

   2. How to fix your pitch before investors do it for you

Part 1: Why founders are bad judges of their own pitch

1. No one teaches you how to do this

Somehow, you’re just expected to “figure out” how to build a compelling pitch. Meanwhile, millions of dollars hinge on it.

That quiet anxiety you feel? That’s your signal something’s wrong — but you don’t know what.

2. You’re blind to your own gaps

There’s a reason authors hire editors.

I once worked with a founder who proudly claimed an 88% success rate on a slide. Impressive—until I asked:

“What’s the success rate of your competitors?”

He didn’t know.

That single miss would have killed the pitch instantly with investors.

Founders miss obvious gaps not because they’re careless, but because you can’t critique what you’re too close to.

3. Most pitch examples online are misleading

You can study decks from companies that raised money, but you have no idea:

• What investors actually liked

• What they ignored

• What almost killed the deal

Copying decks without context wastes time and creates false confidence.

Part 2: Three stress tests your pitch must pass. If your pitch fails any of these, you have a problem.

Test #1: The 7-second test

Can you explain what your company does—and why it’s meaningfully better—in 7 seconds or less?

If not, investors won’t wait.

Test #2: The parroting test

Pitch to someone outside your company. Then ask them:

• What does the business do?

• What’s the company’s secret?

• Why does that secret matter?

• Why can’t competitors easily copy it?

If they can’t repeat this back in nearly your own words, your message isn’t clear enough.

Clarity is not optional. Investors move on fast.

Test #3: The vision test

If your vision doesn’t appear in the first two slides, you’re already losing attention.

I once waited until slide seven.

That was a mistake.

Vision must come early—and repeatedly.

Part 3: How to fix your pitch

1. Don’t outsource it

Don’t hire a “done-for-you” pitch service. Don’t start with a designer.

Raising capital is one of the most important jobs you have as CEO. No one understands the nuance of your company better than you.

Outsourcing leads to generic, forgettable pitches.

2. Get to the point—immediately

You have seconds to create an emotional connection.

Every word that doesn’t increase clarity is costing you attention.

Clear messaging doesn’t just inform—it resonates.

3. Dig into the pain, then sell the vacation

Customers tolerate inconveniences. They don’t tolerate real problems.

Contrast is your weapon.

Make life without your solution feel painful. Then make life with your solution feel like a vacation.

Fundraising always takes longer than you expect:

Pre-seed: 6–12 months

Seed: 9–18 months

While the clock is ticking, cash is draining—and competitors are moving.

The earlier you get your pitch right, the better your odds.