Fundraise with the "INEVITABLE" Mindset

How harnessing conviction closes VC rounds

Hey there, Chief Storytelling Officers.

Thanks for spending some time with me. Last week, I talked about how Hollywood could help us become better storytellers. Today, I want to dive into the mindset it takes to transfer confidence and conviction from you to a VC. I call this the "inevitable" mindset.

And, as always, I’ve got a couple of great resources to keep your storytelling saws sharp.

Buckle up.

— Robbie

DEEP DIVE: You Are Inevitable

What if you could accomplish everything you’ve ever wanted with a snap of your fingers? It’s possible, you know. At least, it worked for Thanos.

Okay, I understand the Marvel supervillain is a fictional character. I also get that he’s not exactly a role model unless genocide is your thing. But there’s one part of Thanos that I really admire—and something you can learn from him, too.

This is one of those topics that will completely transform the way you fundraise.

For those not deeply engrossed in the MCU, here’s a quick primer: Thanos is an alien warlord whose mission is to collect six Infinity Stones that will give him the power to wipe out half of the universe’s population. He’s the primary bad guy in Marvel’s “Infinity Saga”, and the Avengers chase him around for a couple of movies trying to stop him.

The thing that makes Thanos so terrifying isn’t his superhuman strength or tactical skill; it’s his steadfast belief in himself.

Thanos KNEW it was his destiny to cop the Infinity Stones and accomplish his goal, no matter what the cost. It’s a confidence best encapsulated by his line from Avengers: Endgame: “I. Am. Inevitable.”

This jaw-dropping scene makes for great cinema, but it’s also a mindset I think all founders should adopt.

The best founders in the world all know they’re going to succeed long before it happens. They possess a sense of knowing the future, and that it’s their destiny to succeed. There are NO other options.

If you look at successful people in any domain—athletics, art, business—they all maintain that same sense that their success is inevitable. Let’s look at a few examples:

Usain Bolt

Eight-time Olympic gold medalist Usain Bolt is widely regarded as the greatest sprinter of all time. He got there through hard work, of course, but also a dogged self-belief. “A lot of legends…have come before me, but this is my time,” Bolt said. Many have criticized Bolt over the years for what they perceived as cockiness, but time and again, Bolt silenced them with his results. “I told you all I was going to be number one, and I did just that,” he told reporters after setting an Olympic record in 2008.

Arnold Schwarzenegger

Austrian bodybuilder Arnold Schwarzenegger knew he wanted to be a Hollywood movie star since he was 14 years old and saw a magazine article about Mr. Universe starring in a movie. “[I thought], if he could do it, I could do it!” Schwarzenegger said. “I’d win Mr. Universe. I’d become a movie star.” But the path wasn’t easy. Filmmakers said Arnold’s body was too large for the screen, and his Austrian accent was too thick. During his first role in 1970’s Hercules In New York, all of his lines had to be overdubbed by an uncredited voice actor. But Arnold believed something movie producers didn’t. “I knew I was a winner back in the late sixties,” he said in a speech. “I knew I was destined for great things. People will say that kind of thinking is totally immodest. I agree. Modesty is not a word that applies to me in any way—I hope it never will.” Fourteen years later, that same thick Austrian accent delivered what would become one of the most iconic lines in movie history: “I’ll be back.”

Conor McGregor

UFC Champion Conor McGregor used doubt as motivation his entire career. He said he knew even when he was broke and living with his parents that he’d become the world champion. “Saying I’m going to do something, putting it out there for the world to see, and then going out and doing it—there’s no better feeling than that,” McGregor said after he won his second UFC world title. “I’ve been listening to them laugh my whole career. ‘He’s all hype, he’s all talk, he’s a joke.’ Laughter all around at the joker. Then the joker goes and wins a world title.”

Kanye West

In 2002, Chicago native Kanye West had made a pretty big name for himself as a producer. He’d written hits for Jay Z, Ludacris, and Alycia Keys, but he had his sights set on something bigger: he wanted to be a rapper. West recorded his own album and peddled it to labels, but execs were reluctant to sign him because he didn’t portray the bad boy image prominent in hip hop at the time. But Kanye knew he was destined for more—so much so that he convinced his friend to follow him with a camera and document his rise to fame. “I am Warhol, Kanye said in a now-famous interview. I am the number one most impactful artist of our generation. I am Shakespeare in the flesh.” Roc-a-Fella Records ended up releasing Kanye’s first album because he wouldn’t stop bugging them about it, and, well, you know the rest.

What do all of these greats have in common? A sense of inevitability. And that level of conviction comes through in the way that they present themselves.

Whether you realize it or not, how you show up in the world affects your success as well. When you possess an unwavering faith in yourself—when you KNOW that you’re going to deliver, that you’re going to be successful—guess what happens? Success follows.

Shifting your mindset

The way we think about ourselves is how we show up. Science has repeatedly shown that our actions—and our results—are drastically affected by our self-identity. Author James Clear points out in his book, Atomic Habits, that many people would be more successful if they set identity-based goals instead of results-based ones. Don’t set a goal of losing 20 pounds, Clear writes, BECOME a health-conscious person who makes exercise a part of their daily routine. Likewise, a Proceedings of the National Academy of Sciences study found that people who identified as “voters” were more likely to head to the polls than those who simply “voted.” Changing the word from a verb to a noun impacted turnout because when an action is part of our identity, we’re more likely to do it.

Self-identity can negatively impact you as well. Telling yourself that you’re bad at math or not a morning person bakes that belief into your identity, and it becomes a self-fulfilling prophecy. If you think “I might fail,” you are attracting failure into your life. If you know you’re going to succeed, you know what you’re attracting? Success.

But here’s the catch: you can’t just label yourself a successful founder and it will be so. You’ve got to be speaking from the heart. When you actually BELIEVE, your energy will change. And people will notice.

At the end of the day, fundraising comes down to a transfer of conviction and confidence from you, the founder, to the investor. If you don’t have that conviction and confidence, you can’t give it to the investor.

Why are investors willing to get on board with you? Most would say it’s because they believe—not in the product, but in the founder. Sure, the potential success of your product is important, but it’s rare for startups to go to market without pivoting. An EPFL study found that 73% of businesses pivot their market or product at some point. Investors understand that—what they’re investing in is YOU.

Investor insight into "inevitable" mindset

Super-investor Chris Sacca said finding unicorns like Twitter, Instagram, and Uber was fairly easy for him because their founders had a different air about them. “[Instagram founder] Kevin Systrom, back when he was coding solo…when you talked to him about Instagram, he would say without any hint of irony or doubt would say ‘when we get to 50 million users, that’s when we’ll launch this new filter,’” Sacca said. “In his voice there was so much inevitability that he was going to get there. You talked to Travis [Kalanick] in the early days of Uber, and it was clear they were going to take over the world. There’s something about founders who, when you sit down with them, they just know they’re working on something bigger than the rest of us. They can see in the future, and you want to jump on that train before it leaves the station.”

That’s what I’m talking about. That’s the level of success and thinking about success that enables conviction from investors.

As a founder, what I encourage you to do is think about that level of inevitability. Nothing is going to stop you. You are DESTINED for that level of success.

So take a lesson from Thanos. Whoever your favorite success story is. I guarantee you if you go look at them and you study how they got there, there are going to be moments where they predicted it before it ever happened.

The Greatest of All Time

In February 1964, up-and-coming boxer Cassius Clay earned a bout against heavyweight champion Sonny Liston. Clay made a spectacle of the weigh-in, calling Liston a “big, ugly bear.” “I am the greatest,” Clay said. “15 times I told the clowns what round they were going down in, and this chump ain’t no different.”

Seven rounds later, the boxer who would later change his name to Muhammad Ali secured a TKO victory from Liston, becoming the youngest heavyweight champion of all time. “Eat your words!” he shouted at the press, who’d listed his odds of winning at 7-1. “I am the greatest! I shook up the world! I’m the prettiest thing that ever lived!”

That’s what it takes. It takes that level of belief in yourself. Not something you’re making up. You can’t make up that belief, conviction, confidence. It comes from inside of you. It’s when you know you’re going to succeed, that you’re the best in the world at what you do.

Show up day in and day out and do the work. If you do that, you have the ability to transfer that conviction. You have the ability to show up as the best version of yourself.

Most of all, you have the ability to become inevitable.

RESOURCES for Founders and Storytellers

CVCs (Corporate VCs) often have a reputation for being fair-weather investors, but in the decade since the dot-com crash, they’ve significantly ramped up their participation. The recent market downturn has resulted in everyone pulling back a bit, but Q2 data suggests CVCs might not retreat as much as they have in the past. Why? Many CVCs are taking more traditional investment approaches, becoming more financial-first than they have in the past.Read PitchBook’s full analysis on the future of CVC investments here.


Earlier, I mentioned that Kanye West thought his fame was so inevitable, he invited his childhood friend Coodie to follow him around with a video camera and document his rise. What resulted was nearly two decades of footage, which Coodie turned into the Netflix documentary jeen-yuhs: A Kanye Trilogy. I’ll admit, the third episode is a little tough to watch because you get an inside look at the wheels falling off the bus, but the first two episodes that document Kanye’s rise are nothing short of inspiring. Put aside what you think you know about Kanye and let his mindset spur you to greatness.


Need some more inspiration for gaining confidence in your pitches? Startup mentor Alexander Jarvis has a great podcast episode about just that. In it, he underlines the importance of not what you say to investors, but HOW you say it. Give it a listen here.


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