Confidence vs. Over-Confidence + Fundraising Fieldnotes 03.25.25

I got to their projections slide and almost threw up. $12M ARR in 2025. "You actually believe this is possible? That seems crazy," I said.

This was a real situation of a founder projecting their business to go from 0 to $12MM in a year. To be fair, I’m all for ambitious goals. But these projections? Crazy town.

And that got me thinking: people always tell founders to project confidence when pitching investors. But I’ve never seen someone draw the line between confidence and overconfidence. It’s a thin line, and crossing it can cost you.

When a Pitch Goes Too Far

Most of your pitch is about the future. You’re making big, exciting statements about how the industry is shifting. You’re pulling up market size estimates that suggest huge potential. You’re laying out financial projections that imply massive upside. Done right, this builds momentum. The investor is nodding along, buying into the vision, seeing the opportunity.

And then you push too far.

Maybe it’s a revenue projection that triples every year. Maybe it’s a claim that you’ll dominate a market that doesn’t really exist yet. Maybe it’s a hiring plan that assumes you can build a world-class team at record speed. Whatever it is, it breaks the spell.

Now instead of nodding, the investor stops. Instead of thinking, “This is promising,” they’re thinking, “No freaking way is this possible.”

And suddenly, the entire tone of the meeting changes. Instead of engaging with your vision, the investor starts picking apart the details. If they don’t believe one number, what else should they be questioning? What other assumptions aren’t grounded in reality?

This is where a pitch goes from compelling to questionable. A great pitch makes an investor feel like they’re catching a train barreling ahead, something exciting, inevitable, and worth jumping on. But when you are too aggressive, it has the opposite effect. Instead of momentum, they sense fantasy. And once an investor starts questioning the believability of your pitch, it’s hard to pull them back in.

Why Overconfidence Kills Credibility

Some founders assume that bigger numbers = a more impressive pitch. After all, investors want big returns, so shouldn’t they want to see big projections?

Not exactly.

Investors want to be excited about an incredible future…but they also have to have confidence that you can bring them to that promise land. When projections feel unrealistic, it doesn’t make you look ambitious; it makes you look like you don’t understand your own business.

Realize your goal isn’t to throw out the biggest numbers possible; it’s to throw out the biggest numbers an investor will be excited to hear from you.

To be excited in big numbers, an investor has to have trust that you can get there

Confidence Has to Be Earned

The tricky part is that the line between confidence and overconfidence isn’t the same for everyone. Not everyone can get an investor excited with the same massive story. If you’re a second-time founder with a big exit, you can push things further than a first-time founder with no track record. If you’ve already raised from top investors, you have more room to be aggressive than someone pitching for the first time.

Your credibility, the trust you’ve built up, and the momentum you have in your process all determine how far you can stretch things.

Investors want to bet on confident founders, even somewhat crazy ones. But they also need to trust you. If they don’t believe in you, they won’t believe in your numbers, your strategy, or your ability to execute.

The best founders walk that line perfectly, bold enough to inspire, grounded enough to be trusted. And that’s what gets deals done.

Recap on how overconfidence breaks trust:

• It makes investors question your judgement. If your numbers don’t feel rooted in reality, they’ll start wondering what else you haven’t thought through.

• It signals a lack of experience. Investors know that nothing ever goes 100% according to plan. If your pitch assumes flawless execution, it suggests you haven’t been through enough challenges to know better.

• It shifts the conversation from “big opportunity” to “Is this even possible?” Instead of talking about why your business is exciting, now you’re stuck defending numbers that don’t add up.

And once an investor stops believing in your projections, they stop believing in your execution. That’s when a pitch falls apart.

How to Check Yourself

So how do you know if you’re pushing too hard? A few ways to test your own projections:

• Do you actually know what assumptions your numbers rely on? Are any of them, let’s be honest, miracles? The founder of my old firm, Greycroft, used to talk about the “cascade of miracles” that would be required for certain projections to hit. If your entire forecast depends on everything going perfectly, your numbers probably aren’t realistic.
  

• What could go wrong? Things always take longer than expected. Hiring slows you down, sales cycles drag, and customer acquisition costs creep up. If your model assumes a straight shot to success, investors will see right through it.
  

• Have you tested your numbers with people who know your industry? Founders, operators, advisors, anyone who can poke holes in your assumptions before an investor does. If they look at your deck and immediately call BS, you’ve got some adjusting to do.

Be chased,
Jason 

I can't underscore how much the ability to take smart ownership of projects/tasks is to me with my team. Earn a CEOs trust and you'll go far.

Just good inspiration on what it means to solve real pain points. Not ones you make up in your head and believe people need...

Currently in Brazil… yeah this checks out 😂🇧🇷. 6 years of high school Spanish …totally wasted

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