Why a good fundraise feels like a storm

The best way to navigate the chaos to a successful round

April 9, 2023
min read
Greetings, Chief Storytelling Officers.

This is the 40th edition of the newsletter. I've shared over 60,000 words and we've grown this to over 2,000 founders and storytellers.

As we think about what's ahead for this newsletter it would be great to hear your thoughts. Back in my trial lawyer days I walked back to the jury after every case and asked them to be brutally honest with me and give me their feedback. They understood the brief. It was in fact BRUTALLY HONEST.

So do you mind doing me a quick favor and replying back with your thoughts on these questions below.

What do you like? What don't you like? What would you like to see more of? How could the newsletter be improved?


DEEP DIVE: Eye of the Hurricane

There’s this great movie from the mid-’90s called Twister, starring Bill Paxton and Helen Hunt. The pair are storm chasers who drive across Oklahoma attempting to deploy weather instruments into the heart of the country’s most violent tornadoes.

(Fun fact: I wanted to see this movie in theater but my mom wouldn't let me since it was rated PG-13 and I was only 9 at the time.)

Their job is literally to put themselves in the path of the worst storms Mother Nature has to offer.

It’s terrifying to think about. The National Weather Service reports around 80 people die from tornadoes each year, causing 1500 injuries and $229 million worth of damage.

But watching this movie, you’d never get that feeling. Paxton and Hunt are sanguine, even happy to put their lives on the line. Their dialogue is littered with deadpan observations and witty banter. They THRIVE on the chaos of the storm.

I felt this same way when I was a trial lawyer. Every case was filled with some form of chaos, and it was my job to keep my cool. I had to make sure the jury never saw it or felt it. I had to make sure the defense attorney never saw a flicker of doubt or weakness cross my face.

That experience helped me navigate one of the most important parts of my role when I’m working with founders trying to get funding—staying calm in the storm.

Because you’d best believe that a great fundraise is like driving into a tornado. Chaos is everywhere. Lead investors get excited, and it feels like the deal is inevitable. Then they come back with questions, making it feel uncertain.

Follow-on investors might likewise say they’re in, but then they’ll come back saying only at certain terms. It feels like it could fall apart.

All of this back and forth can give you whiplash if you’re not careful. It’ll also make lesser founders head for the storm bunker. But I promise you, inside the storm is where you want to be.

Why Storms Are Good

Some people I talk to disagree with my belief that a good fundraise should include chaos. They argue that if you prepare the right way from the beginning, it should be smooth sailing.

I push back on that because to me, the storm indicates energy. There’s momentum. Chaos means that investors are sitting up and taking notice. There’s a buzz in the air, much like that electricity you feel in the atmosphere before a big storm.  

Think about it this way: which is going to make more waves—a light summer rain or a hurricane? Which event is going to cause people to turn on the news, or run to the store and stock up on bread and toilet paper?

I’m not saying you shouldn’t have a plan, that you should run headfirst into a deal with no preparation and try to shoot from the hip. But to think that you can predict every move, every question, every objection a potential investor might have is asinine.

Mike Tyson said it best: “Everybody has a plan until they get punched in the mouth.”

Finding Calm in the Chaos

I’m not going to lie, chasing storms is scary for founders. A potential deal will send you through a rollercoaster of emotions. It’s something I got very used to during some of my tougher cases as a trial lawyer.

One of the craziest cases of my life involved two stabbing victims both in the ICU, a deaf and mute witness who also had lost 6 of his fingers, a judge who hated the case, a convicted murderer as a key witness, and a convicted drug dealer who showed up to trial 3 hours late and walking into the courtroom with sunglasses on.

It would take 10,000 words to tell that story but throughout that entire trial, nobody knew I was feeling the walls close in on me. The outcome was a long prison sentence for the defendant who had nearly killed two different men in the stabbing spree.

There are multiple instances of greats finding calm in the chaos throughout history. One of my favorite examples is from Martin Luther King. In 1962, King was speaking at a Southern Christian Leadership Conference when a man jumped from the audience and punched King in the face. Rather than retaliate, King dropped his hands and allowed the man to hit him again. When King’s security came to escort the man away, King said “Don’t touch him. We have to pray for him.” He took the man backstage and talked with him for several minutes before returning to the stage and finishing his speech, holding an ice pack to his bruised face.

As a founder, you WILL be thrown into some chaotic situations when seeking funding, and you need to know how to handle yourself. Keep perspective and know this is part of the game. Control what you can control and let everything else fall away. There’s no sense in wasting time and energy on things beyond your control.

Ernest Hemingway once defined courage as “grace under pressure,” and I think that’s an apt way to think about going into your funding rounds. You must be prepared to run toward the storm, and once there, handle yourself in a manner that will ensure your success.

You may not be chasing real tornadoes, but it will certainly feel that way at times. Many of the founders I work with know that firsthand.

Remember that chaos is a part of life. It’s how we handle it that decides the outcome. And always be on the lookout for the storm. The storm is what causes the rainbow.

And at the end of that rainbow? Your pot of gold.  

RESOURCES for Founders and Storytellers

Want some tips on staying calm in the midst of chaos? Check out this article from author Kevin Daum, courtesy of Inc.

Founders massively over-index on pitch decks. Here's why that happens and how you can avoid the traps.

A deeply insightful thread from Julian Weisser who does a ton of angel investing and is a co-founder of On Deck. He gets into why VCs aren't able to help a founder on their narrative, negotiation, and communication strategy for fundraising. This is exactly why after trying 102 jury trials, being in a courtroom for over 1000 days, and teaching trial advocacy at SMU Law School that I started Founder Fundraising and Competitive Storytelling.


"Turning pro is a mindset. If we are struggling with fear, self-sabotage, procrastination, self-doubt, etc., the problem is, we're thinking like amateurs. Amateurs don't show up. Amateurs crap out. Amateurs let adversity defeat them. The pro thinks differently. He shows up, he does his work, he keeps on trucking, no matter what." -Steven Pressfield (author of my top 3 favorite books, Gates of Fire).

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Looking for more on how we work with founders looking to fundraise? Check out Founder Fundraising to learn more and apply.

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