How to Become More Confident at Fundraising
Written by Dave Bailey
Written by Dave Bailey, Aug 07, 2025
Many founders tell me they want to feel confident before they kick off a fundraise.
It’s a reasonable wish. Confidence helps you sell.
So they spend weeks building the perfect pitch deck, rehearsing their story, polishing their data room. And don’t get me wrong, those things really help.
But even when you’ve prepared as well as you possibly can, you still might not feel confident.
Confidence Comes Last
That’s because confidence isn’t an input. It’s something that builds along the way.
There’s a framework by Dan Sullivan called The Four Cs:
- Commitment
- Courage
- Capability
- Confidence
You only get confidence after you develop new capabilities. And capability only grows when you commit . . . before you know how things will turn out.
That’s where courage comes in.
We often picture courage as a steel-faced warrior charging into battle. But real courage means you’re scared—and you do it anyway.
Clarify The Capabilities You’ll Build
Fundraising is a huge learning experience for CEOs. Framing it that way doesn’t just reduce the pressure—it actually unlocks energy and curiosity.
Start by capturing the capabilities you want to build:
- Learn how to run an effective process
- Learn how to best present your business to investors
- Learn what sort of investors you’d like to work with
- Learn how to negotiate a term sheet
This isn’t about proving something. It’s about learning something.
Set Better Goals
The way to build a new capability is to set goals.
But not just any goals. Goals you can actually control.
A good goal meets three criteria:
- They’re realistic
- They increase your chances of a good outcome
- They don’t rely on anyone else
That last one trips up most founders.
Getting an investor to say ‘yes’, or even like you, isn’t a good goal. It’s outside your control.
Instead, focus on controllable behaviours. Here are examples of good, goal-worthy actions you might set during a fundraise:
- Start every pitch with a smile.
- Pause every few minutes to check in.
- Answer questions succinctly.
- Set aside five minutes at the end to book the next meeting.
- Write down three positive learnings after every call.
Clarifying and committing to goals like this helps you create a Game Plan for every investor meeting—the three things you’ll do in your next meeting, no matter what.
Suddenly, building capability isn’t a mystery. It’s just setting goals and following through.
Forget Confidence, Choose Courage
If you’re waiting to feel confident before you fundraise, you might be waiting forever.
Instead, commit to doing your best, grow your capabilities, and confidence will soon follow.
Related Reading
- How to Craft a One-sentence Origin Story
- How Great Founders Present Their Vision
- How to Build a Better Business Strategy
- Three Principles to Staying Sane While Running a Startup
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Originally published Aug 7, 2025, last updated Jul 19, 2026.
