Pitching is pain

I want to write your startup's story with you, not judge a dog-and-pony show

Things were looking rough: More than a month into attempting to raise a seed round for our company, Beme, my cofounder Casey and I had little to show for it. We had pitched around 20 investors in New York, netting a couple of small checks and some infuriating “maybes.”

The East Coast was not treating us well. So, in a century-old cliche, we decided to try our luck out West. Investors in SF then seemed to be taking bigger risks. They didn’t look nauseated at the mere mention that we were building a new social media product.

(You might be surprised to hear we had trouble raising money. But it was 2014. Casey was not yet “Casey Nesitat from YouTube, oh my god!” He was a filmmaker who was just starting to vlog. I was an engineer who had helped build exactly one successful social product, Tumblr. Social media was presumed dead and dominated by Meta. We were not important. Fundraising was brutally difficult. )

Casey and I strategizing before a meeting. I’m a bit sad for founders who raise money on Zoom and don’t get to have these embodied moments.

Out West, we had spent a week driving the cheapest rental car available—a little red Yaris—endlessly back and forth between downtown SF and Sand Hill Road. It was our last day in town, and we still had no lead investor. We were in our car on one of downtown SF’s many unsavory corners. I felt about as deflated as the man across the street who was passed out on a crumbling office chair in the middle of the sidewalk.

We did this fundraise entirely wrong. I can see that only now, having been on the investor’s side dozens of times. The endless chasing and the stunt we were about to pull should have been warning signs.

One investor who kept eluding us was Matt Mazzeo, famous then for having made a bet on Gimlet. We were desperate to meet him, and weren’t trying to hide it, having called in every favor and mutual connection to make it happen.

Suddenly, Casey’s phone rang, flashing Mazzeo’s name. Maybe, finally, we would be able to meet this guy. Maybe he would be the lead investor we were seeking.

Speakerphone on:

Mazzeo: Hey Casey, sorry to give you guys the run-around, but I’m actually headed back to LA in a couple—

Casey: Where are you right now?

Mazzeo: I’m at a coffee shop in South Park, just finished a meeting and about to head to the airport.

Casey looked at me for a signal. His sense of the layout of SF was so bad he had booked us a hotel next the Golden Gate Bridge, near approximately zero of our meetings. I pointed down the block and held up five fingers.

Casey: Meet us in the park in 5 minutes.

I had already plugged South Park into Google Maps. Committing a variety of minor traffic violations, we got there right in time. Casey took inspiration from the gritty flavor of the neighborhood and grabbed a brown paper bag from the backseat. It was the kind of bag someone might use to disguise a beer on the street. “Load up the demo and put your phone in here.” I did as instructed.

We walked into the park and took a seat at a picnic table, shivering, as one always is in SF. Two minutes later, Mazzeo joined us. He was charming and warm as you’d expect from a former talent agent. But underneath the smile, he did not seem thrilled. Our pitch was standing between him and the end of a long day.

After some brief pleasantries, Casey slapped the brown bag on the table and slid it across to Mazzeo. “Brought you something.”

It was a beautiful act of theater: a fledgling company asking for a million dollars, in a gesture that would have looked to any passerby like a minor drug deal.

The mood shifted entirely. Mazzeo burst out laughing as he took the phone from the bag. I talked him through our demo. He listened intently to our now well-oiled pitch. For a moment, we thought we might have found our man.

The other shoe soon dropped: “I don’t think I could get there on this.” That’s VC for “haha no way am I backing this (yet).” Even though the pitch landed perfectly, all the effort had been for naught. He gave us some sage advice and a couple of helpful introductions and we parted ways.

Boil investors like frogs

Where did we go wrong?

We should have made writing a check the logical conclusion to a months-long conversation. Instead, we were showing up out of the blue, with a fully baked plan. Rather than give investors like Mazzeo time to get to know us, we demanded an immediate thumbs up or down.

Casey and I had been prototyping and iterating on Beme for six months. We are thoughtful people, and were probably among a few dozen of the most focused-on-social-video humans on earth at that moment. Many investors who we ended up talking to in the loaded environment of a pitch would have gladly spoken to us much earlier in the process. They would have had time to get to know us, to see that we had made appreciable progress, and to understand our vision.

And yet we hid off in our bunker. We were terrified to speak with investors until we had nailed the entire story and built a fully usable first version of the product.

I absolutely would not go back in time and show investors the horrific early Framer prototypes of our product. First impressions matter a lot, and all these early versions of the product were true flops. I absolutely would, however, have brought investors into our thinking.

We should have developed relationships months earlier, instead of driving around the Valley in a moderately controlled panic, trying to find a VC willing to sign up for a shotgun wedding.

Recruit me, early and often

Now that I’ve been sitting on the other side of the picnic table for a few years, I see things differently. First meetings are the beginning of a personal and financial relationship that will last a decade, with risks to my career as well as yours.

For early stage investors like myself, it’s a ferocious privilege to have founders share their companies! I love meeting founders early in their process, and not just ones already in my network. When the idea isn’t yet fully baked, I feel the thrill of getting to author the story with the founder. I am recruited to your team, not acting as your judge. And most importantly, you are developing a relationship and strong answers to the hidden questions that actually underlie most early investment decisions—about resilience, depth of thought, and founding team chemistry.

Raising money for the first time is as vulnerable as walking into every meeting with a bloody nose. A perfectly practiced pitch seems like armor against this vulnerability. Counterintuitively, though, the pitch becomes a wall between you and me.

Want the brass tacks? Aaron Harris has a great tactical guide to having coffee with investors.

Are you a star engineer who wants to build a consumer product, but feels like no one would ever fund it? Are you a deep expert in an industry, tinkering with an idea but unsure how it becomes a company? Is there a part of the healthcare system that has been driving you mad? A niche change in the way people watch, buy, eat, live, do, that you know is going to become the mainstream in a few years?

Your company might not be a company yet. It might be just you. But you can see how the world is going to play out, and you know precisely what mark you want to make on it. You have the threads and beats and pieces of the story, but they don’t really fit together yet.

This is the perfect time. Find some investors who care about what you’re building, be concise and intriguing in the way you contact them, and don’t get discouraged by some silent no’s.

It doesn’t take a phone in a paper bag to start building relationships that can become funding and lasting partnerships.