Keep Calm, Carry On
Welcome back y'all,
This past week I met up with one of the founders I work with here in Miami. It was an enlightening conversation in so many ways.
The biggest reminder from him is that because we were able to help him raise 12m instead of his targeted 5m amount, he's been able to hire absolute rockstars on his team and make huge progress with his company.
His words: "Robbie, here's what I didn't realize. By raising 12 instead of 5, I was able to hire every single person I wanted. The best of the best. At 5m I would've never been able to and we'd be struggling."
A great fundraiser is a great storyteller. It's the 2nd order consequences of the fundraise that matters.
Better valuation so there's less dilution. Better talent who can get the job done (think 10x engineers). Greater security for the team to not worry about layoffs so they can do their best work. The ability to operate from a position of strength with future investors because of longer runway.
Now, to our deep dive.
DEEP DIVE: Cool as a Cucumber
I was recently talking with an MP at a VC, and I asked them for their biggest piece of advice for founders who are fundraising. Their answer was simple: never let them see you sweat.
One of the toughest things to master when you go into a high-stakes situation—meetings, pitches, business conversations—is presence. When I watch founders present to investors, many times I see them lose their presence. An investor asks them a question they either weren’t prepared for or that stings a little bit, and their facade crumbles. They lose control of their emotions—their facial expressions, their body language, their tone of voice. All of a sudden, the founder is no longer in control of the conversation. The power dynamic has shifted, and once it’s gone, it’s VERY difficult to wrestle back.
Today, I’ll talk about why this skill is so important, as well as ways to keep your cool in the face of just about anything an investor can throw at you.
The Pressure Cooker
There’s this great scene in the movie Old School where Owen Wilson’s bogus fraternity is going through a series of tests in order to win their charter. After failing an event, Wilson gives a pep talk to the team, and Will Ferrell chimes in. “We can’t have anyone freak out out there!” Ferrell screams. “We’ve gotta keep our composure!” Then he slams a folding chair against a locker.
This moment is exaggerated for the sake of comedy, but the irony of Ferrell’s point resonates. No one believes his inspirational advice because HE has lost his composure. I haven’t yet seen a founder bang a chair against the wall (though I’ll never say never), but I’ve certainly seen them crack under pressure. Most often, this looks like answering a question in an aggressive or defensive way. Their brows furrow or their tone shifts from measured confidence to a tremble of panic or dagger of annoyance. While these changes may seem subtle, you can feel the mood in the room change. The founder is on their heels.
The truth is, you’re inevitably going to be in situations where investors are going to ask you questions you don’t like. They might ask a question you think is dumb or one you were unprepared for. Often, they’ll ask a tough one you don’t want to answer.
The first thing you want to do when faced with a dumb/hard/scary question is stop making assumptions about why it’s being asked. The moment you start thinking “this investor is dumb and they’re asking me dumb questions,” you’ve made an assumption. You’ve now given THEM control.
You have no idea why the investor is asking the question. Sometimes investors are testing you. They’re purposefully trying to push buttons to see how you respond in the moment.
You might say “Robbie, that’s not okay, they shouldn’t do that.” But why shouldn’t they? These investors are trying to figure out if you can lead a company and handle tough questions. If you’re successful, you’re going to be talking to press. You’re going to be talking to shareholders. Do you think those people are going to tie every question up with a pink bow?
We all know this. The press is not out to be your friend. They’re trying to make a good story, which means they want to push on you and make you respond emotionally so that you give them something juicy to write about. Sometimes, investors are just pressure testing you to see how you’ll stand up in the future.
Other times, you get some bad questions because investors make a mistake. They’re human, and they have bad days. Something might be going on at home or at work that you have no idea about. They’re certainly not going to share that with you.
The bottom line is that when you make an assumption, you’re working with bad information, and you’re allowing that information to affect your performance and response. Like Will Ferrell said, keep your composure.
Frame to Maintain
Now that you understand why keeping calm is so important, how do you do it?
It’s a common question founders ask me ALL THE TIME. My answer is to maintain your frame.
At its root, a frame is the lens through which you view the world. It’s influenced by your beliefs, values, perspectives, and personal quirks. Obviously, everyone’s frame is slightly different, and your goal in a meeting or presentation is to get your audience to see the world through your frame.
This is easier said than done. When your audiences’ frames don’t match yours, a power struggle ensues. You both push against each other to bend your frames so they’re more congruent.
A good way to think about frames and frame control comes from USC management professor Kathleen Kelley Reardon, whose book, The Secret Handshake, describes frame control as a series of up, down, or across moves. When you one-up someone, you’re taking control of the conversation and acquiring power. When you one-down, you’re ceding control, and when you one-across, the power remains neutral.
Here’s an example of what I mean, courtesy of an article from The Power Moves:
Because of the way Laura responds in this interaction, she cedes power to Matt and doesn’t maintain her frame.
Let’s look at the same interaction, this time with Laura maintaining her frame:
As seen through this interaction, the way to maintain frame is not to let anything affect you. Absorb, absorb, absorb. Once you do that, think it through: what is the tone that I want to display in this setting?
One of the best examples of maintaining frame comes from the Netflix show, Peaky Blinders. If you haven’t seen it, put it in your queue now because it’s one of the best-written shows out there. The main character Tommy Shelby is not only a badass, he’s the coolest-headed character ever to grace the screen.
Over the course of the show, Tommy has stared down some of the scariest criminals in the world. He’s been threatened, kidnapped, beaten, poisoned, and shot. But when faced with a conflict, Tommy NEVER reacts emotionally. Stoic and calm, he takes in the information and always pauses before he responds. He sits back and thinks through what he’s going to say next.
There’s a great moment in one episode where Tommy is asked about his job. A woman whom Tommy outbid for a racehorse says “I breed racehorses and train them. What is it you do?” Tommy takes a moment, and without flinching replies: “I rarely answer questions is what I do.”
It’s that thoughtfulness—being able to reframe the woman’s question—where he maintains his frame and control.
You can see this throughout the entire series. He’s always keeping his wits, making sure his facial expressions never give away how he’s feeling internally in that moment. There are absolutely times in the show when he gets super angry, but it’s always in private. You’ll never see him deliver a message in anger. Internally, he may be enraged and in chaos, but he never lets his workers or the opposing party feel that.
Another (non-fiction) example of unflappability is this famous clip of Steve Jobs answering an incendiary question at the 1997 Worldwide Developers’ Conference. Jobs had just returned to Apple as an adviser, and he was under immense scrutiny as he tried to guide sweeping change at the company.
In the clip, Jobs takes a long pause before answering and identifying why he did the things he did. He maintains frame. He demonstrates he’s the expert—someone who doesn’t get rattled, who doesn’t respond emotionally and instead replies in an articulate, thoughtful way that maintains control and power over the conversation. He replies the way HE wants to, not the direction the questioner is goading him.
When you can master that, you can understand how to maintain presence and control frame so that you seem unshakable. Keep your tone strong. KNOW that you’re the expert in the room, and that nothing can stop you from being successful.
This doesn't mean you aren't passionate about your idea. This doesn't mean you aren't warm in your tone. This doesn't mean you don't show enthusiasm about your team and idea.
It means you don't let an investor rattle you.
You maintain control, no matter what.
When you do that as a founder, you’re going to see the results that you deserve, the results you expect, and the results that would make Tommy Shelby proud.
RESOURCES for Founders and Storytellers
Is there anything sweeter than redemption? Not for the USA men’s basketball team, a collection of NBA stars who found themselves in a surprising underdog position heading into the 2008 Summer Olympics. Their inspiring journey is captured in a new Netflix documentary called The Redeem Team. It’s an incredible example of how leadership (from legendary Duke coach Mike Krzyzewski can make a difference. It’s also a great showcase of Kobe’s Mamba Mentality, which you know I love.)
While many in the VC world liken partner-founder relationships to a marriage, the reality is that often it's easier to get divorced than to kick someone off your cap table. Jess Lee, partner at Sequoia Capital, has sat on both sides of the table, and in this Tech Crunch article shares her insights for founders wanting to understand what makes the big VCs tick.
It’s not a founder’s market anymore. At least, that’s what this PitchBook report claims. Market investors are starting to take advantage of falling valuations and rising interest rates with more structured equity deals. This recent increase in structured equity is "yet another sign that the pendulum has swung in investors’ favor after the end of a long bull market during which founders, who often received more offers of financing than they needed, could cap investor returns or impose other terms.” Structured financing in new fundraising rounds can come at a cost to founders, and even to new investors.
A beautiful reminder from one of my favorite authors and one of the greatest storytellers alive today.
"Storytelling is the essential human activity. The harder the situation, the more essential it is." -Tim O'Brien
If you want to work with me on your fundraising or storytelling, you can reply to this email to speak with our team about what that looks like. Our consultancy is highly selective but we are always happy to point you in the right direction if it's not the right fit.
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.