11 things to nail for a successful fundraise

Greetings, Chief Storytelling Officers.

The Roman Empire is having a moment in pop culture right now. Rome placed a huge emphasis on effective oratory and rhetoric. There’s a reason their ideas, leaders, and history have continued to survive.

They were one of the greatest storytelling empires in history.

Now let’s get into a Deep Dive packed with help for you.

-Robbie

11 things to nail a fundraise

The buzz in the startup world is palpable; the sheer number of founders I've spoken to who are gearing up to pitch in this September through November window is staggering.

The timing is no coincidence. It comes hot on the heels of the August lull, a period when investors traditionally break for summer. But with this opportunity also comes a stark reality – the competition is set to be ferocious. The question every founder should be asking themselves right now is: how do I stand out in this bustling marketplace?

The answer, while straightforward, requires unwavering commitment. Immediate preparation is key.

With a fundraising endeavor demanding a 4-6 week lead time for thorough preparation (at least), the clock is ticking. This is your chance to craft a compelling story, one that resonates and sticks.

Last week a Series A VC told me, "the story shows us if they will be able to raise more money and lead a team".

Beyond that narrative, the intricacies lie in building a robust Investor CRM, seeking those invaluable warm intros, and honing your conversational acumen. While the temptation might exist to take shortcuts, remember: improvising often ends in disappointment.

The way you manage your fundraising journey speaks volumes to investors about your professionalism.

After all, Kobe Bryant's relentless offseason training wasn't for naught. It was a testament to his dedication and it's what set him apart.

Founders, take note. The same could hold true for you.

Let’s dive into how you can hit the Fall fundraising season… HARD.

1. Don’t rely on the pitch deck

In the startup world, there's a story we hear a lot: a place where investors eagerly give money to founders with big ideas, inspired by big names like Uber, Facebook, and Peloton. Many see these big companies as the ultimate goal and try to copy them. For instance, there are millions of search results on Google showing how to make a pitch deck like the big companies did years ago.

But why would today's thinkers use old ideas?

Here's the funny part: even as people talk more about these presentations, they're actually becoming less important. A study from Docsend shows that investors spend only three minutes looking at them, and this time is getting shorter. Still, many founders spend too much time and money on them, thinking it's the key to success.

What they miss is that real relationships and trust are becoming more valuable. Big names in the industry, like Peace Mitchell and Chris Tuff, say that we're moving from just sharing info to building real connections.

For investors, it's not just about the numbers, but about the person and their story.

That said, pitch decks can still help. They're good for organizing thoughts and can be shared after a good chat. But, top investor Jason Lemkin says he often makes up his mind in just 20 minutes. So, for founders, it's time to be themselves, tell their real story, and connect on a deeper level. In the end, it's not about copying old ideas but about being genuine and passionate.

2. Focus on the story

Researchers have long concluded that a standard business presentation will activate the language processing areas of the brain but not much else. A story, on the other hand, activates much more, including the areas we’d use when experiencing the events ourselves.

The fancy term that’s been used is neural coupling. If you ever saw the movie Pacific Rim, it’s a bit like that mind meld that happens with the Jaegar pilots. Mirror neurons fire and syncs the listener’s brain with the speaker’s brain.

Investors care because if you can tell a story, you can lead an organization to success.

3. Know WHAT to Say

Knowing what to say is all about getting the content right. It’s the Goldilocks rule: not too much, not too little, but just right.

In the beginning stages of learning how to tell stories, we often think every detail and factoid is precious. But the best storytellers know that often, less is more.

Think about Neil Armstrong in 1969. He was able to encapsulate the entire majesty of landing on the freaking moon in just 11 words: “That’s one small step for man, one giant leap for mankind.”

Or what about Abraham Lincoln, whose 1863 Gettysburg Address lasted all of two minutes.

(Fun fact: this speech echoes a much earlier speech from The History of the Peloponnesian War by Thucydides. In Pericles' Funeral Oration there are similar themes and structures as in the Gettysburg Address. I point all this out to remind you that great artists borrow, remix, and find inspiration in many places).

Lincoln’s speech was preceded that day by former Harvard dean and renowned orator Edward Everett, who spoke for over two hours. Unless you’re a real history buff, I doubt you’ve even heard of him.

There is nothing worse than being unheard of.

4. Know HOW to Say it

This is where things like tone, pacing, volume, and musicality come into play.

Great storytellers can use delivery tactics to influence their audience.

In his “Finest Hour” speech, Winston Churchill used a slow, measured pace to convey calm and confidence to the British people in the face of Nazi bombardment. Martin Luther King, Jr. employed the musicality of Shakespeare and Southern preachers to compel his audience to action.

Without rhythm, pacing and musicality, a story will sound boring.

With rhythm, it sounds like music.

And music sticks with people and moves them.

5. Know how to FEEL the story

An effective storyteller can actually sync their brain waves with their audience (remember that neural coupling idea from earlier). That’s what’s happening when you get so engrossed with a story that your surroundings melt away.

At this highest level, you’re actually creating change within the brain, carving neural pathways that didn’t previously exist. The listener adjusts what they’re thinking and feeling at the same time.

The name of the game here is authenticity and vulnerability. The story isn’t just a story—it’s REAL. In order to get to this place, you must remove the mask you usually wear in the world and let your audience see who you really are—warts and all.

There’s a level of talent needed to get to this stage that simply can’t be taught. It’s the X factor—the je ne sais quoi—that separates the great storytellers from the truly elite.

Storytelling is BOTH an art and a science. The FEEL part is the art. It takes dedication to achieve this.

But once mastered… the world is yours.

6. Craft your Founder Origin Story

Every superhero has an origin story, and as a world-class founder, so should you. Your mission in crafting your origin story is twofold:

1 — To build trust with your audience.

2 — To set your frame.

When you properly craft your origin story, you establish yourself as a character that your audience wants to root for. Do it right, and your audience will sympathize with you—no matter the circumstances.

Answer these THREE questions:

How did you get here? What makes you special? Why do you care?

So, when you tell your story and answer these three questions with honesty and vulnerability, you're not showcasing perfection.

Instead, you're revealing the perfect founder

That's something entirely different from the stuffy suit-and-tie stereotype with impeccable hair and rehearsed lines. People don't want that. What they crave is the raw and real you.

7. Craft your Startup Origin Story

Once you’ve established your personal origin story, it’s time to craft your company’s. This is all about showing why what you’re doing is important NOW, as well as demonstrating that people WANT what you’ve built, and making it HUGE in the future.

This is one of the most difficult storytelling skills for founders to acquire. For some reason, as soon as people begin to describe their business, they go brain dead and start speaking in jargon, technicalities, and features.

The way to craft your Startup Origin Story is by using the three Ps:

Purpose, Passion, and Potential.

Purpose is all about identifying the problem and solution. What problem will your product solve, and why is now the right time to do it?

Passion gives you the opportunity to share your emotion and transfer it to your audience. You want to explain why you and everyone else involved—your team, your customers, and your investors—should too.

Potential is when you lay out how big this opportunity can be. You instill confidence by demonstrating how you will defend your vision and make sure you win.

8. Craft your Future Vision Story

Whether you realize it or not, you’re very familiar with Future Vision Stories. Pop culture is filled with them. “The Jetsons” told a Future Vision Story of what life would be like in the 21st century. Ditto The Matrix, Black Mirror, Demolition Man, Star Trek…the list goes on and on.

The first step is to determine which Future Vision is right for you. Do you want to describe the short-term future—one-to-two years—or the long-term—five-to-10?

Once you do that, ask yourself what that future looks like if everything goes perfectly. What does the world around you look like?

Like I said before, this is the most creative skill of the three, and as such you should employ literary techniques just like novelists do. A great device to use is imagery, wherein you describe not just what things look like visually, but what they sound like, smell like, and taste like. Engage every sense however you can.

This is true world building. It’s my personal favorite as it’s pure art.

9. Speak Like a Pro

Remember this: clear speaking is a sign of clear thinking.

Articulation isn't about speed; it's about control.

So, slow down.

Many people sound out of control because they talk too fast, causing their brain to lag behind their mouth. The outcome? Rambling, stuttering, and overusing filler words.

Think of it like skiing. If you ski too fast and lose balance, you end up tumbling.

You may not think it’s fair. You may not like hearing it.

Doesn’t change that investors are judging you on your performance. And yes, it is a performance.

The best speakers, from Oprah to Barack Obama to Steve Jobs, have a controlled pace. By slowing down, you give your brain the advantage to process and present your thoughts clearly.

10. Prepare set piece for your speech

Think of speech like sports. Before the big game, teams practice set plays - specific, well-rehearsed movements. Similarly, articulate speakers have set pieces - a toolbox of stories, analogies, metaphors, and quotes that they've mastered and can pull out when needed. Some tips:

Have 5-10 personal stories ready to share.

Think of relatable moments from popular culture, like movies or sports.

Powerful lines from famous figures, books, or poems that support your message.

11. Record and Review

Record yourself.

Athletes watch their performances to improve, and speakers should too. This will help you identify and rectify quirks or habits that hinder your articulation. Maybe you have a speech tick, use upspeak, or start sentences with 'so' too often. By identifying these, you can work on eliminating them.

I watch game tape of all the founders I work with to see what they are doing right and where they can improve. I bring lots of tough love in those sessions and it’s a big part of why founders improve at such fast rates.

Wrapping up

It may seem like a lot—to have to learn all of this for fundraising.

But I’m telling you: investing in this learning is one of the primary ways that World-Class founders separate themselves from the pack.

Investors expect a founder to be great at fundraising. They know it’s the lifeblood for your business. Remember, even an IPO is a form of fundraising. You’ll still be telling the story to get people to value your business the right way.

By mastering these 11 skills, you won’t ever have to worry about being lost in the stack of 1,000 pitch decks.

In fact, if you do it right, you won’t be in that stack to begin with.

An exchange between Keith Rabois and Danny Miranda

Keith Rabois: "Famous athletes, famous DJs, famous politicians- none of them who are successful are humble. You may not know if it from their public persona. But definitely- these people have significant confidence from in they're doing. And it's backed by reality."

Danny Miranda: "Do you think the bravado came before the actual action?"

KR: "That's a great question. I think sometimes yes- people know when they're really good at something. I said to him [Derek Jeter] when you see a rookie in spring training, can you tell from the first at-bat whether they're going to be successful? And he said yes. I thought it'd be something about swing, or technique. But he said 'it's their confidence.'"

Resources of the week

Bill Gurley spoke at the All In Conference and since I shared his 1999 article last week, here’s some thoughts from him these days.

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Conclusion First storytelling video that breaks down how to do this especially when talking with people who want to know what’s in it for them.

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If you’re headed to NY Tech week in October here is a growing list of the events scheduled.

Looking for help on your fundraise or storytelling?

I want to help as many world-class founders as possible and that has led to a full client roster right now.

If you want to work together in the coming months apply below as the most promising founders and companies will get the first openings as they come up.

If it’s crazy urgent, let me know.