Greetings, Chief Storytelling Officers.
It's good to be settled back in Miami for a few weeks. I'll be heading down to Brazil to spend some time with the rapidly growing Latam startup and venture ecosystem alongside my friend Jason Yeh.
This week I took a listen to Rick Rubin's interview on Joe Rogan.
A few things stood out.
First, was how different the creative process is for Eminem and Jay-Z. Eminem writes relentlessly. Jay-Z sits in silence and then go off the top of his head. These are two of the greatest of all time. Just shows there's no "right way" to create magic.
Second, was the reason Rick Rubin found success in the industry. According to him he said it was his his lack of experience with the traditional frameworks of production that let him think differently. He wasn't constrained by industry standard practices or dogma.
The second point hit home since so much of my approach to storytelling and fundraising comes from my 7 years as a trial lawyer and 4 years coaching the national mock trial team at SMU Law School. I don't rely on old ideas in the venture capital space because I didn't come up in that world.
For you, I hope it shows how you can turn a perceived weakness into a strength. You don't need to be ex-google, ex-uber, ex-rappi, or ex-whatever to be successful as founder.
You just need a great idea, grit, resilience, and an obsession with excellence.
Let's get into that more with today's Deep Dive.
DEEP DIVE: Planning for D-Day
On June 6, 1944, Allied troops launched Operation Overlord, the largest seaborne invasion in history. More than 5,000 vessels, 1,200 planes, and nearly 160,000 troops crossed the English Channel and landed in Normandy that day.
We all know about D-Day and its orchestrator, General Dwight Eisenhower. But what often isn’t remembered is the story of its organization.
Documents now suggest President Roosevelt and Winston Churchill began talking about the “second front” attack as early as March, 1942. Every aspect had to be considered, including how supplies would be transported to troops and how German reinforcements would be blocked. The planning involved significant setbacks, including a devastating German ambush that resulted in over 1,000 casualties during a D-Day rehearsal.
Not everything went according to plan on that day, of course, but ultimately, Operation Overlord was a success. “Plans are worthless, but planning is everything,” Eisenhower said.
The same is true when you’re fundraising. A great fundraise is months—if not YEARS—in the making. It’s not going to happen overnight, and it’s not going to happen by magic.
The thing is, you’re never going to read about all of the work successful founders put into their prep. All you’ll read is the headline on TechCrunch or PitchBook—Startup raises $X Million in recent round. They make it look so easy.
But all you’re seeing is the tip of the iceberg. Why? Because all of the work leading up to that successful round is incredibly unsexy. No one wants to hear about how the founder put together a great CRM and identified warm intro sources. No one wants to hear about the weeks the founder spent getting their FAQs in order, how they honed their frame and structured their pitch in a way that’s concise, precise, and clear.
Here are some tips to help you plan for your own D-Day.
Discipline, Not Motivation
If I asked you if you were motivated to be successful, the answer would obviously be yes. But in order to succeed, motivation isn’t enough.
See, motivation isn’t as powerful as we think it is. We can see that just by looking at the word’s definition. Motivation: (n): The general desire or willingness of someone to do something. In other words, motivation can inspire you to accomplish something, but it’s just a desire—and it’s often fleeting.
“Motivation is a wonderful thing to take advantage of when it strikes,” writes Flabs to Fitness founder Allison Wojtowecz. “It gives us unusual powers of focus and productivity. But motivation is finite…We can almost think of it as a separate being from ourselves that chooses when to visit. We can’t beg, force, or manipulate it into sticking around longer than it wants to.”
Another way to think about motivation is what the ancient Greeks call “the Muse”—the inspirational goddesses of literature, science, and the arts. Artists often attribute the Muse as the source of their greatest work. When the Muse visits, the artist is merely a conduit through which the other-worldly genius flows.
But as any successful artist will tell you, waiting for the Muse to visit isn’t enough. “Don’t wait for the Muse,” novelist Stephen King writes in his memoir, On Writing. “As I’ve said, he’s a heard-headed guy who’s not susceptible to a lot of creative fluttering. [Writing] isn’t the Ouija board or the spirit-world we’re talking about here, but just another job like laying pipe or driving long-haul trucks.”
So if motivation or waiting for the Muse isn’t enough, what does being successful take?
Unlike motivation, which is a noun, discipline has a verb form. To train by instruction and exercise; to drill.
For about a decade, heavyweight boxer Mike Tyson was unbeatable in the ring. He knocked out opponent after opponent with a frightening amount of power. While natural talent certainly played a role in Tyson’s success, his training regimen was insane.
According to a Sport Bible article, Tyson would spend eight-to-10 hours working out each day, beginning with a three-mile run at 5 a.m. Over the course of his day, he’d complete 2,000 squats, 2,500 sit-ups, 500 dips, 500 push-ups, 500 barbell shrugs, and 10 minutes of neck exercises.
In addition to preparing his body, Tyson also prepared his mind. He studied film of his opponents fighting, and then rehearsed his technique with 10 rounds of sparring.
That type of dedication didn’t just come from a motivation to win. It came from discipline.
“I don’t care how good you are in anything,” Tyson said on the Joe Rogan Experience podcast. “If you don’t have discipline, you ain’t nobody. You’re nothing without discipline, ‘cause you give up under the slightest struggle without discipline. Discipline is doing the thing you hate to do, but do it like you love it.”
Unsexy Work = Sexy Results
Let’s go back to that Stephen King quote for a second. Despite having written over 50 best-sellers and making millions of dollars in his career, King STILL likens his work to a blue-collar job—like “laying pipe or driving long-haul trucks.” He shows up to work every day and gets it done.
In a similar anecdote, author Steven Pressfield (whom I’ve mentioned before) said in an interview that he wears work boots to his writing desk every day as a reminder to punch the clock and do the work.
The work itself is not sexy. It is boring, lonely, frustrating, and never-ending. No level of romanticizing could dress it up. Why do you think Rocky Balboa’s months of preparation were compressed into a three-minute training montage? Because watching him train in real time would’ve put the audience to sleep!
Guess what all of these world-class people discovered about doing the unsexy work? If you show up consistently and without fail, the RESULTS are sexy. The Muse shows up.
Here’s the second half of that Stephen King quote from On Writing: “Your job is to make sure the Muse knows where you’re going to be every day from 9 ‘til noon. Or 7 ‘til 3. If he does know, I assure you that sooner or later, he’ll start showing up.
I found that to be true in my law career as well. The more consistently I showed up, the more I prepared for a case, pouring over documents and testimony, the more often the Muse visited me. My track record in the courtroom was no accident—it came from doing the unsexy work.
"Preparation Creates Precision"
This quote comes from Justin Mikolay who's a good friend and also the former speechwriter for General Petraeus, Secretary Panetta, and General Mattis. We've talked at length about his speechwriting process and it's mind blowing how much work goes into crafting every single speech these political leaders make.
With that in mind, let's get a bit tactical.
How can you prepare to run and execute a smooth fundraising process?
The biggest thing to think about early, and I mean 6-12 months early, is building relationships with founders, operators, and VCs.
No matter what anyone says about cold outreach working or funds being open to cold pitches, it works for maybe 1% of founders. It's a losing strategy for 99%. That means warm intros continue to rule when it comes to getting meetings with investors.
Build a list early. 100-150 investors that would be good for what you're building. Then start building relationships with people who can introduce you to them when it's the right time. Please understand that this takes time. If you want to fundraise in January, you should've been doing this since at least July of this year.
Next, prepare the team to run the day to day while you fundraise.
Finally, work on your mindset. It's the make or break for most founders in the process. Build your resilience. Build your stress tolerance. Push yourself so nothing can break you in the fundraise.
Because you will be pushed and tested.
So if you want to build a billion plus dollar company, embrace fundraising as part of the game.
Fundraising takes grit and setting the board long before you're ready to start playing the game. Nobody shows up to a meeting and gets handed money. But with the right mindset—prioritizing discipline over motivation—and the willingness to do the unsexy work, when your D-Day comes, you’ll be the hero who orchestrates the largest scale attack in history.
RESOURCES for Founders and Storytellers
CVCs have historically been criticized as tourist investors, but a new PitchBook report shows that even in a cooling market where asset managers, private equity firms and others are taking a more cautious approach, they’re still writing checks. CVCs have participated in more than a quarter of US VC deals this year, the report shows, which is the highest rate in a decade.
There’s plenty of talk about battening down the hatches in the tech startup world, but according to attendees of the TechCrunch Disrupt conference in San Francisco, they’re still shooting for the moon. Read more about the industry’s rose-colored outlook here.
All that optimism said, the outlook isn’t so rosy for web3 funding. An article in CrunchBase this week reported funding to VC-backed Web3 startups—as well as the number of deals—dropped to its lowest since the end of 2020. See more details on the dip here.
I saw The Kite Runner on a limited run while I was in NYC. That performances were powerful and left me feeling a flood of emotions. I never read the book and had no idea what the play was going to be about.
I warn you that the subject matter is tough and highly charged but it's an amazing story. If you're looking to study great storytelling, you might want to pick up the book.
As always, great to have you reading. See you next week.
Performative Speaking is a consultancy working with and advising venture backed founders to become world-class storytellers, fundraisers, and founders. If you want to speak with us about our process and results, you can apply at Performative Speaking.
A former trial lawyer and prosecutor in Dallas, TX, Robbie trains founders to become world-class storytellers and venture capital fundraisers.
In barely two years, he's helped founders raise $575,000,000 of venture capital.