Find Your Fundraising Champions

Being a leader isn't enough—you also need followers

October 24, 2022
min read

Greetings, Chief Storytelling Officers.

Another week, another deep dive coming your way.  

This week I'm up in NYC as I'll be speaking at Antler's office here in front of a few hundred founders covering how they can prepare now to become elite storytellers and fundraisers.

Before I forget, I started watching the new Netflix show on the rise of Spotify. It's called the Playlist.

A few things stood out.

  1. The level of conviction from founder Daniel Ek that nothing would stop him from building his vision.
  2. The tagline the music exec in the show came up with to describe the company..."Infinite Digital Jukebox".
  3. The type of champion Daniel's co-founder provided for his vision. Martin Lorentzon went all in supporting.

That 3rd thing brings us to today's deep dive. See you on the other side.

DEEP DIVE: Haaaave You Met Ted?

I’ve said over and over again that when you’re pitching to a potential investor, you’re not just selling your company or product—you’re selling yourself. Investors know that in addition to signing a check, they’re also signing a marriage certificate of sorts, wedding them to you in sickness and in health.

Now let me clear something up. Selling yourself is what amateurs do. The professionals show up as the best version of themselves and know they have what it takes to be special. That's why I say...

Being yourself > Selling yourself

The world-class founders that are able to attract the highest levels of funding, best talent for the team, and create long term brand love all understand how to become that best version of themselves.

When they do this, they become inevitable.

I’ve also stressed the importance of being inevitable, to walk into a room with the swagger of someone who KNOWS you will succeed. Building your ethos is a large part of persuading your audience and gaining their trust.

But it’s also hard to brag about yourself and come off as likable. There’s nothing more annoying than talking to the guy at the party who starts every sentence with I.

So how do you strike that balance between confidence and pomposity? One of the best ways is to get yourself a wingman.

We Are the Champions

Creating champions of your work is an essential but often overlooked part of getting the ball rolling. If you can create a champion, they will do the heavy lifting and spread your message for you.

Think about the Medici family and the champion of the arts they provided in the city of Florence. Brunelleschi, Botticelli, Donatello, and Michelangelo all found champions in the Medici family.

We see examples of this principle at work in both The Bible and Quran. Jesus had the 12 Apostles, and Muhammad had Sahabi, or Companions of the Prophet. In a secular context, The Beatles had a fan club, or with the recent mania around a new album release it's clear that Taylor Swift has a mass of champions.

One of my favorite examples of this principle...Ted Mosby who had his iconic wingman, Barney Stinson.

The How I Met Your Mother character played by Neil Patrick Harris spent the majority of the sitcom seeking his own companion using his infamous Playbook, but he also loved playing matchmaker for his best friend. He did so with a simple introduction: “Haaaave you met Ted?”

Obviously, pitching to an investor is far more nuanced than picking up someone at the bar, but the principle remains the same. The champion has the potential to sell you before the investor even meets you.

An important thing to take away from this newsletter is how much strategy goes into a great fundraise (and this can also apply for sales and recruiting). Finding your champion takes time to build the relationship. It takes time to find the right person. Time to help them see why you're worth championing.

In 1922, Toronto Star reporter Ernest Hemingway moved to Paris to pursue his dream of being an author. He was unknown and unpublished, but he did have one thing: letters of introduction from author Sherwood Anderson. In those letters, Anderson generously described Hemingway as “a quite wonderful newspaperman whose extraordinary talent is sure to take him far.”

The recipients of these letters, which included poet Ezra Pound, Shakespeare & Co. bookstore owner Sylvia Beach, and author Gertrude Stein, gave Hemingway the access to what’s now considered one of history’s most famous artistic networks. In Stein’s salon, Hemingway met F. Scott Fitzgerald, James Joyce, and Pablo Picasso, among many others. Within a year, Stein assisted him in finding a publisher for his first two books (3 Stories and 10 Poems and in our time). His first proper novel, The Sun Also Rises, was published shortly thereafter.

None of that would have been possible without Anderson’s letters. He was Hemingway’s champion.

Finding Your First Followers

So how do you go about championing your champions?

A first step is understanding the First Follower Theory, a concept introduced by entrepreneur and writer Derek Sivers.

In his 2010 Ted Talk, Sivers posits that the leader isn’t necessarily the most important person when trying to start a movement. He says the first follower is equally important, because they’re the one who transforms the lone nut into a leader. When properly nurtured and encouraged, the first follower can lend credibility to what otherwise might be a risky idea.

“As more people join in, it’s less risky,” Sivers says. “Those that were sitting on the fence before now have no reason not to join in. They won’t stand out, they won’t be ridiculed, they will be part of the in-crowd—if they hurry. Eventually, they will be ridiculed for NOT joining in.”

Next, you have to curate your first followers. They could be an advisor, a prior investor, or close friend who’s tied into a powerful network. But a word of caution: don’t force your connections to be champions too soon.

In a previous newsletter, I mentioned Chris Tuff’s book, Save Your Asks, which details how to form authentic networking connections. In the book, Chris introduces the askhole—someone who repeatedly asks for favors without doing anything in return. “They might be good people overall, but they are way too internally focused on their networking or relationship building,” he writes. “If you’re an askhole, people don’t want to make connections with you because they don’t want their connections to be annoyed. If they do, they’re likely to make half-hearted connections, and they’re not going to connect you with their best contacts. Don’t be an askhole.”

This was one of those lessons I learned early as a trial lawyer. In that world, favors were currency. I had to learn how to navigate both the legal and political world as a prosecutor. Make asks when appropriate and only agree to asks when I knew I could trust the other side.

An interesting side to it in the world as a year, a defense attorney was my opponent. The next, they might be the district attorney and my boss.

Guess what?

That happened multiple times during my career. And they people who built strong relationships benefited. The ones who burned bridges, lost their jobs.

My job rested on my ability to make champions with judges, prosecutors, and defense attorneys.

Like Sivers says in his Ted Talk, champions must be cultivated and encouraged in an organic way. While social media has made connecting with people easier than ever, sending blanket LinkedIn messages to people you barely know asking them to make introductions isn’t effective. In fact, it may have the opposite effect.

Instead, focus on fostering champions with whom you already have a deeper, mutual connection. Think about the people in your network and play Six Degrees of Separation. Trust me, you’re better connected than you think!

The Best Way to Deploy Your Champion(s)

Let's get into how you can use your champions as a founder that's fundraising.

Step 1: Introductions.

If I've said it once, I'll say it one thousand times...warm intros are everything when trying to get meetings.

Some champions can open up 10 meetings for you. Others can open 50 meetings. Some may only open 1 meeting, but it's the perfect fit.

Step 2: Back Channel

Investors like to see that founders have a network and smart people who believe in them. Back channeling is a way to show that network inside of the tech or industry related world. If you're building a tech company in the media space, it's helpful to have champions who send the signal that you know and can navigate it.

There is no such thing as too much back channeling. The more great people who can sing a founder's praises, the easier it is for an investor to make the bet.

I say this not only from watching it happen repeatedly but also from my own POV. I have certain people who if they tell me something, I don't question it. They have proven themselves to me as trustworthy and forward thinking.

Step 3: Keep building the relationship

This isn't a way to deploy the champion but what you will find is by continuously building the relationship new doors will be opened for you. A potential high level hire, a partnership you never dreamed of, or a whole bunch of other things will just appear before you.

Never take them for granted. Always be grateful. Make them look good.

Prioritize finding your champions. Let them tell your story for you.

When it’s done right, the champion does the heavy lifting, and all you need to do is tap the ball into the net.

The easiest goal of your life.

Here's hoping the US Men's team can get some of those in the World Cup next month.

RESOURCES for Founders and Storytellers

In its truest form, being a founder is looking to the future and doing what you feel is right. But as this Forbes article on cultivating champions points out, you are on your own until someone else notices what you are attempting to do and validates your efforts to others by joining in.

Q3 was a mixed bag for the US venture landscape. Deal activity across all stages recorded signs of distress, and investors dealt with a lack of liquidity in the public markets. On the bright side, fundraising rose to record highs during the quarter. This PitchBook analysis captures VC trends in five handy charts.

The robots are taking over! As the enthusiasm around AI image and text generation grows, AI content startup Jasper announced this week that it raised $125 million in its most recent round. The company’s valuation is now at $1.5 billion. This TechCrunch article has all the details.


I want to say a quick thank you for reading each week. I know these are long newsletters that require time and energy.

60% of you read them. 40% don't.

To the 60%, keep putting in the work and big things are coming. The best founders I work with all have an insatiable curiosity and obsession with getting 1% better every day.

By you reading, it tells me you just might be one of those who in a few years is the subject of your own Netflix show about your rise to the top.

I can't wait to see it.

Know someone who might enjoy it? Please pass it along!

Last week I put a message here to reply to this email if interested in working together and the inbox got flooded, so I'll put it again.

If you're a venture backed founder or multi-time founder looking to become world-class at storytelling and fundraising, reply back to this and we will set up some time with our team to see if we can turn you into that world-class founder.

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