How to manage your mind while fundraising

Why it is so hard, and what to do about it.

Matt Munson

13 Dec 2024 — 4 min read

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“God, I feel like an absolute loser. Did it ever feel this bad for you?” I asked my good friend and advisor.

“Every single meeting I got turned down in—which, by the math, was almost all of them.”

“How long am I going to feel this way?”

“Probably until the next good meeting.”

This conversation happened about twelve years ago. I was sitting in a parking lot off Sand Hill Road, having just been summarily rejected in a Series A pitch meeting. The person on the other end of the line was an advisor, someone a few companies ahead of me who had raised hundreds of millions of dollars.

As a coach, I now spend my days talking with founders about the hardest parts of the entrepreneurial journey (and life) —and few parts are more mentally challenging than fundraising.

Why Fundraising Feels So Hard

To begin with, it feels like everything is on the line. I remember the weight of years of work my team and I had poured into our company. My entire career and reputation felt at stake. These beliefs, while not entirely accurate, are deeply understandable.

After all, if I don’t get the company funded, we’ll run out of money. If we run out of money, we’ll have to shut down. If we shut down, I’ll have to start over—either building something new or finding a job. And I’ll be tagged as the founder/CEO whose last company crashed and burned. My team, too, will be left searching for jobs from a failed company. The stakes can feel enormous—and understandably so.

Then there’s the math. Fundraising involves hearing a lot of “no’s” before you hear “yes.” For that Series A I mentioned earlier, we ultimately received several term sheets from top firms. But to get there, we endured nearly two dozen rejections. That’s a lot of rejection—even in what turned out to be a successful round.

Another uniquely hard part of fundraising is how lonely it feels. Much of startup building feels like a team sport, but fundraising often feels hauntingly solo. As a coach, I see this shift frequently: CEOs who use “we” when discussing company accomplishments suddenly switch to “I” when discussing fundraising.

It often feels like, “The team has done their part; now it’s all on me.” And if I mess up, I’ll render months or years of team effort worthless. For many founder/CEOs, this burden can feel deeply personal—particularly since many of us CEO-types carry a childhood pattern that we are responsible for everyone’s well-being. It is a heavy weight to carry into pitch meetings where presence and creativity are essential.

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How to Ease the Burden

Given these challenges, how can we effectively manage our minds during fundraising? Below are some strategies to stay present and functional throughout the process.

1. Structure a Tight Process

Decide in advance the total number of investors you’ll pitch—say 80. Break this into 3–4 cohorts. Don’t burn through your entire list in the first pass. Start with a smaller group, say 20, and schedule those meetings over a two-week period—about two meetings per day.

This tight structure has several benefits:

• Focus: It allows you to stay in the fundraising “zone,” alternating between pitching, recovery, and preparation.

• Confidence: Even if one meeting goes poorly, you’ll know others are on the calendar.

• Scarcity: You can tell investors, “We’re taking all first meetings this week and next,” which creates urgency and positions you as a pro.

• Clarity: A defined endpoint lets you reflect and regroup if needed before the next cohort.

To set up this structure:

• Build your target list at least three months in advance.

• Identify intermediaries (for warm introductions) two months out. More on that here.

• Group investors geographically to minimize travel and maximize efficiency.

2. Practice Your Pitch Until It’s Second Nature

Your pitch should be so well-rehearsed you could deliver it in a loud bar with two friends telling you different stories in each ear. This doesn’t mean it should sound robotic—great comedians, for example, seem off-the-cuff, but their sets are meticulously practiced. They know where each joke, pause, and laugh will come. Aim for the same level of comfort.

I recommend an 8–12 slide deck, delivered in the first 10 minutes, leaving most of the meeting for discussion. Before pitching real investors, practice with:

5–10 founder friends.
5–7 friendly investors (who aren’t a fit for your round but can provide feedback on clarity).

When practicing, treat these sessions like real meetings. No caveats or excuses. Do not talk about the pitch, give the pitch.

3. Build a Support Network

Fundraising is mentally grueling. Counterbalance the stress and rejection by surrounding yourself with support. Pick three key allies—people who understand what you’re going through but aren’t directly affected by the outcome (e.g., not employees or investors).

Ask for their commitment in advance. Be specific about what you need: daily calls, check-ins, dinners, or something else. Their role is to remind you that your worth and their friendship are not tied to this process.

4. Plan Your Time Outside the Room

Think like a professional athlete. How you spend your time between meetings will influence your energy, clarity, and presence.

Sleep: Get consistent, quality sleep. Avoid alcohol. Stick to a calming bedtime routine.
Move: Exercise daily—yoga, walking, or weightlifting.
Eat: Prioritize whole, healthful foods at regular intervals.
Nature: Spend time outdoors to recharge.
Recovery: After travel, take time to reset—whether it’s a half-day or a full day for long-haul trips.

5. Have a Bounce-Back Plan

You will have bad meetings. Expect them. Plan for them. Think about what will help you recover—a long walk, a call to a friend, or even a milkshake. When it happens, let yourself feel the discomfort, acknowledge it, and then move on.

Two Final Reminders

1. Fundraising is a Market of One.

You’re looking for one lead investor to write a term sheet. The second term sheet will be much easier. Focus on finding that first “yes,” not on the rejections along the way.

2. You Are Not Alone.

Fundraising is one of the most anxiety-inducing parts of the entrepreneurial journey for nearly every founder. You’re in good company. Reach out to your friends, fellow founders, or even me—I’d love to support you.