🧠 Confession time. The first time I tried to pitch your startup like a pro, I absolutely did not. I stood there—hands sweaty, voice doing that weird shaky thing—explaining my idea like I was apologizing for it. Halfway through, I realized I was talking faster than an auctioneer on espresso, and the investor across the table was nodding… but not in a good way. More like the way people nod when they’re mentally drafting a grocery list.
You ever feel like that? Like you know your idea is solid, but the second you open your mouth, it turns into alphabet soup?
Yeah. Same.
Anyway, after a few years, a few bruised egos, and more than a few “Thanks, we’ll be in touch” emails that were never followed up on (rude), I figured some stuff out. Not perfectly. Not gracefully. But enough.
So this is me—coffee in hand, probably rambling a bit—telling you what actually helped me pitch without wanting to crawl under the table.
1. Stop Trying to Sound Smart (It’s Weirdly Off-Putting)
I don’t know who needs to hear this, but investors are not impressed by buzzword soup.
I once said something like, “We’re leveraging synergistic verticals to disrupt legacy frameworks.”
The investor blinked. Once. Slowly.
She finally said, “So… what do you actually do?”
Oof.
Here’s the thing: when you try too hard to sound impressive, you sound like you’re hiding something. Or worse—like you don’t really understand your own idea. If you can’t explain it simply, that’s a problem. Not a cute one.
Talk like a human.
Explain it the way you’d explain it to your cousin who still thinks “the cloud” is weather-related.
If you can’t do that yet? Cool. That’s not a failure. That’s homework.
2. Tell Me Why You Care (Not Just Why It Makes Money)
Yes, money matters. Obviously. No one’s here for charity bake sales.
But if your entire pitch is numbers and projections and hockey-stick graphs, you lose people emotionally. And humans—shockingly—make emotional decisions first and justify them with logic later.
Why did you start this?
For me, one startup came from getting screwed over by a service I hated but had no alternative to. I was annoyed. Like, deeply annoyed. That frustration stuck. So I built something better.
When I told that story, people leaned in.
Not because it was dramatic—but because it was real.
If you don’t care about the problem, why should anyone else?
3. Your First 60 Seconds Matter More Than the Rest
This part still stresses me out.
The beginning of a pitch is like a first date. You can’t open with your entire life story or your 10-year roadmap. You need a hook.
Not a gimmick. A hook.
Something that makes them think, “Oh. Interesting.”
Ask a question.
Share a quick moment.
Drop a surprising stat—but like you’d say it out loud, not like you memorized it from Google.
One time I opened with:
“Okay, quick show of hands—who here has ever paid for something they didn’t actually use?”
Boom. Engagement. Tiny win. I’ll take it.
4. Know Your Numbers… But Don’t Marry Them
You should absolutely know your numbers. If you don’t, that’s a red flag the size of Texas.
But here’s where people mess up: they cling to them like a life raft.
Investors will question your assumptions. That’s their job. If you get defensive, it looks bad. If you crumble, it looks worse.
Instead, treat your numbers like… educated guesses. Because that’s what they are.
When someone pokes a hole in them, say something like:
“That’s fair. Here’s what we’re testing right now.”
Calm. Curious. Not wounded.
(Yes, this took me years to learn.)
5. Practice Out Loud (Yes, You’ll Hate It)
Reading your pitch silently in your head does not count as practice. I don’t care how good it sounds in there.
Say it out loud.
Trip over your words.
Realize you hate half of it.
That’s the point.
Record yourself if you’re brave. Or reckless. Or both.
The first time I did this, I cringed so hard I almost threw my phone across the room. But then I fixed the weird parts. The rambling bits. The stuff that only made sense to me.
Pitching is a performance. Not in a fake way—but in a clear communication way.
6. Shut Up Sometimes (Seriously)
This one hurts.
You do not need to fill every silence.
Early on, I thought pauses meant I was failing. So I kept talking. And talking. And talking.
Turns out, pauses mean people are thinking.
Let them.
If an investor asks a question, answer it. Then stop. Don’t tack on three bonus explanations “just in case.”
Confidence often looks like restraint.
Which feels wrong at first. But works.
7. Remember: They’re Just People (With Nicer Shoes)
This was the biggest mental shift for me.
Investors aren’t mythical creatures guarding sacks of gold. They’re people. With biases. Bad days. Favorite snacks. Probably a group chat they mute.
When you pitch your startup like a pro, you’re not trying to impress royalty. You’re having a conversation with someone who wants to find something interesting—and not waste their time.
Be prepared.
Be you—but the clearest, calmest version.
That’s it.
🧠 A Quick Side Tangent (Because Why Not)
Back in 8th grade, I wore two different shoes to school. Not on purpose. It was a Monday.
No one said anything until lunch. And when they did? We laughed. I survived. Barely.
Pitching kind of feels like that. You think everyone’s staring at your mistakes. They’re not. They’re mostly rooting for you to do okay—because awkward pitches are uncomfortable for everyone.
🔗 A Couple Links Worth Your Time
- A refreshingly honest take on startup life from Paul Graham’s essays (Google it—you’ll fall down a rabbit hole)
- This old but gold talk by Steve Blank on customer discovery (still weirdly relevant)
Final Thought about pitch your startup like a pro
You don’t need to be perfect to pitch well. You need to be clear. Human. And a little brave.
Mess up. Learn. Adjust. Repeat.
And hey—if you bomb one pitch? Congrats. You’re officially doing the thing.
Now go pitch your startup like a pro. Or at least like someone who cares. That’s usually enough. 💙
