Here Be Dragons

My love of maps started with Winnie the Pooh. Not the stories. The map.

That hand-drawn map at the beginning of the book, showing the Hundred Acre Wood in perfect miniature. Every path marked. Christopher Robin's house at the top, the North Pole discovered by Pooh in the middle, Eeyore's Gloomy Place tucked in the southeast corner.

What captivated me were the edges. Those little notes pointing off the page. "Nice Place for Picnics" floating in white space. "Heffalumps this way." Arrows leading nowhere and everywhere at once.

The real adventure wasn't in the Hundred Acre Wood. It was wondering what lay beyond.

Everyone knows ancient maps said "Here be dragons" at the edges. Except they didn't. Also, apparently, not everyone knows about the marginalia on mappa mundi. But that’s not the point.

Only one globe from 1510 contains those actual words (two if you include the ostrich egg carving it was likely cast from). But we love the idea so much, we've collectively decided it was true.

We need to believe in edges. We need unmapped territories. We need to think there's still somewhere left to explore, even when GPS has catalogued every square foot of earth.

Silicon Valley has its own version of this. Everyone uses the same map: Stanford to startup. YC to Series A. The fundraising timeline. The hiring playbook. It works fine if you're building the 47th iteration of something that already exists.

But Airbnb? "Let strangers sleep in your house" wasn't on anyone's map. Neither was Uber or SpaceX. These companies came from founders who walked straight off the edge of the known world and started building.

I really like to walk. Walking is par for the course in NYC, but I walked a lot when I lived in LA (shocker).

There's something about the motion itself. Podcast playing, random thoughts bouncing around, the city doing its thing. I'm not hunting for hidden gems. I'm just moving through space with no destination.

But that's when you see things. On Melrose, wedged between Supreme and all the hypebeast boutiques, there's this midcentury building completely overgrown with vines. A tree literally growing through the structure. Turns out it was the office of an architect who built tons of LA's midcentury housing stock.

Now nature's reclaiming it while everyone rushes past to buy limited edition sneakers. It’s one of those weird things that you wouldn’t find by looking for something. Rather, it kinda finds you when you're not trying to find anything at all.

I don’t know for a fact that both Maddi & Lauren mentally roll their eyes every time I say this (a lot), but I wouldn’t blame them because it kind of irritates me.

But I keep saying it, because it’s true. At least to me. Between rejection three and cold email one hundred, something shifted. I stopped trying to follow their prescribed routes and started looking for gaps. Where gatekeepers weren't watching. Which doors nobody thought to guard.

I eventually made it to Lazard. Trust me, the view from up there (literally and figuratively) is nice. I learned something else, however. I fell in love with the pursuit itself. The puzzle of it. Getting to Lazard was almost anticlimactic. It’s not that I was ungrateful for the opportunity. It’s just that I learned what I really liked was becoming someone who could make that climb.

I realized that’s a big part of why I loved running WACC (my community college → Wall Street mentorship program). My journey was over. I was at the destination. But that didn’t mean I was out of the game. I got to go right back to the grind and recruit vicariously through our cohorts. I got to watch them transform, get addicted to their own unlikely journeys, and develop that innate self-belief that comes with success.

That's when I realized this wasn't just my story. It was an investment thesis. Founders with real conviction aren't talking about exits. They're talking about tomorrow's experiment. Next week's iteration. They're high on the pursuit itself. The story they're writing matters more than the ending.

Maddi & I built this fund because we learned firsthand that stories that don't make sense on paper can actually make perfect sense in practice.

When you can't follow the prescribed map, you develop different instruments. You learn to read terrain, not just street signs. You build pattern recognition from pure necessity. Every rejection teaches you something the straight path never could.

That's why we can spot founders that others miss. We're not using the same evaluation criteria because we weren't evaluated by those criteria either. We succeeded despite them, not because of them.

When founders pitch us, we don't start with TAM. We start with "What did you notice that nobody else saw?" Because the biggest outcomes come from founders who couldn't help but explore territories others didn't know existed.

You can spot them immediately. They light up talking about problems nobody else has named. They've thought about edge cases that don't matter yet but will. They're not building because it's smart. They're building because they can't not build.

If you need validators who'll confirm you're on the right track according to the standard playbook, we're not it. If you’re one of those people, I don’t need to tell you that anyway. You don’t want my validation. I know for an absolute fact that I once very transparently wanted yours. I still may, but it’s deeper down inside somewhere.

But if your whole career has been preparation for building something only you could build, we should talk.

Every VC fund chases "unicorns." Billion-dollar companies. As if we collectively decided that mythical horses with horns are the perfect metaphor for startup success. It's absurd when you actually think about it. Maddi actually wrote a whole post about this. In this case, a real eye roll from MH is both expected and likely deserved. But c’mon, I'll always do it for the metaphor like some people do it for the plot. 

I’m not going meta for the sake of it. The very creatures that ancient cartographers used as warnings, we see as invitations. The founders everyone else thinks are too dangerous, too weird, too far off the map? Those are our people. Because dragons, not unicorns, guard the real treasure.

Yes, it's a silly metaphor. Yes, we're adding to the pile of overwrought VC analogies. But if we're all going to pretend that mythical creatures are a reasonable way to talk about software companies, we might as well pick the right ones.

Because we don't back founders who follow maps. We back founders who draw them. Who explore not because it's strategic but because they can't help themselves.

The best maps always have arrows pointing off the page. Notes suggesting there's more. Hints that the most interesting territory is still being discovered.

That's where we invest. At the edge. Where the known paths end and the real building begins.

Because that's where our founders live. That's where we live too.

We built Daring Ventures to be the home for founders who love the journey as much as the destination.