Little Did I Know

Excerpt #2 From My Upcoming Book

“This seed round is looking out of sight.

If I hustle harder, it will all end up alright.

Unfortunately, that’s not how it works despite

Their best intentions—they forgot to mention:

If you’re not part of the inner circle,

You can’t get over the final wall, you can’t get over the final hurdle.

If you’re not a local, you gotta get vocal,

Get on Twitter, you can become the focal point.

I’m not your average founder, I’m sorry to disappoint,

But you’re not gonna pay attention if I send you my PowerPoint.

Look at me—I’m writing a song, got your attention, maybe you’re even humming along.

F#*k consensus, I want to be polarizing,

You look at me, your LPs, and you look like you’re compromising.

You’ve never met a founder quite like me—I’ll build a unicorn and be the startup rap king.

It’s an insiders’ game; I’ve got pattern recognition, but once I’m in, I’m giving everyone else admission.

You wonder, "Who the hell is he?" They call me Mat, but I only got one T.”

- Mat Sherman

I wrote this song and recorded me singing it inside Sip Coffee in Old Town Scottsdale November 6th, 2019. At the time, I was at the tail end of running my company, PubLoft, which had failed to secure funding. I was deep enough in the game to understand what I had done wrong—but not deep enough to know how to change my circumstances. I felt frustrated, so I channeled that frustration into music. I’ve always enjoyed blending my love for music with my insights from the startup world.

I wrote this song after spending years trying to make my startup at the time, PubLoft, work. At the beginning of that year, we received a $100K check from Jason Calacanis and joined his LAUNCH accelerator. Through that, we had the chance to pitch people like David Sacks at Craft, Roelof Botha at Sequoia, and nearly hundreds of other tier one Bay Area investors. Before Jason’s backing, we had grown PubLoft from $0 to $24K in MRR in just a handful of months. Everything seemed to be going right. For me, at least, it felt like this company was the one.

But it wasn’t. The company was toast within a year of securing our first investor. I was confused. How could something that seemed to be going so well fall apart so quickly? How had I made such fundamental mistakes that led me down this path? We had the revenue. We had the logos. We had the backing. So why couldn’t we convert all that into startup stardom—a billion-dollar company?

The answer, I’ve come to realize, is context. Before the accelerator, we knew our business. I knew how to grow it. My cofounder, Jeremy, knew how to retain customers. We knew how to work with each other. We understood our business model—our edge, our strengths, even our weaknesses.

But once we got thrown into the world of Silicon Valley, we were lost—before we even knew it. We didn’t have the right reference points for how this world actually worked. Of course, we thought we did. And of course, Jason taught us to the best of his ability. But there’s a difference between reading Venture Deals and Secrets of Sand Hill Road, and actually living it.

There’s an implicit set of rules in the Valley—a kind of high-context culture—that my batchmates and I had to decode while also trying to keep our companies alive. It wasn’t just about building; it was about understanding the language, the power dynamics, the unspoken norms. And if you didn’t grow up in it—or weren’t coached by someone who had—it was easy to miss the cues entirely.I operated how I thought I needed to operate to win the game. But the reality is—I was so far off from what was actually required that I tanked the company in the process.

I see this in many founders. They’ve got something good going, but they twist and contort their company to fit the Silicon Valley mold. And I get it. It’s the status. It’s the capital. It’s the thrill of playing in the big leagues just to see if you can. But in the process, we experience carnage that doesn’t need to exist.

Simply understanding how Silicon Valley works can feel like a full-time job. And everyone thinks they’re a 7/10 in their understanding of it—when they’re likely a 2 or a 3. I call this the slope of enlightenment.

Personally, I thought I knew enough to be dangerous. In hindsight, I was a 2. So I had my time in Silicon Valley. I watched my company get eaten alive by my own bad decisions—decisions made trying to play a game I didn’t fully understand. And I was frustrated. So I wrote the song you read above. Seemingly stuck.

Little did I know…

• Little did I know that within a year of writing that song, I’d start another company—one that would be seeded by Eric Ries (author of The Lean Startup) and Dave Goldblatt (early Facebook employee), two people I didn’t even know at the time.

• Little did I know that I’d go on to interview nearly a thousand founders on a podcast I created—some of whom would later raise from Sequoia, a16z, and go on to become unicorn founders.

• Little did I know I would amass a following of over 10,000 on X, made up almost entirely of people in tech I hadn’t met in real life.

• Little did I know that I’d eventually work at Product Hunt—the very site that first introduced me to Silicon Valley back in 2016.

And little did I know that my journey would be indicative of so many others—founders trying to raise money without truly understanding the rules of the game. That’s the issue I keep coming back to: the carnage founders face simply because they lack context.

They think they’re 6’6” and ready to hoop, but in reality, they’re 3’5”. Their company might be 6’6”, but their soft skills—their implicit understanding of how capital really flows—might only be half that. Just like I was back in Jason’s accelerator.

And that brings me to this book.

I genuinely believe this culture and context can be taught—if it’s shared through the right medium. I believe a great founder, who has never stepped foot in Silicon Valley, can learn these rules and play the game as well as anyone.

This book is my attempt to communicate the context that lives within the Bay Area. Or, in other words: I’m hoping this book—if read and acted on thoughtfully—can serve as your admission into Silicon Valley and the fruits that come with it.

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Excerpt #1 can be found here

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