OP #302: Keep Building Like No One’s Watching

Early-stage energy isn’t a phase. It’s a mindset.

Author

Darren Herman
July 08, 2025

Hope everyone in the U.S. had a solid July 4th weekend—time with people you love, some good music, sun, maybe a break from the inbox.

I got a little of that… plus a bit of work sprinkled in.
I’m not complaining though. Some of that work was deep in the weeds: synthetic research projects for a couple portfolio companies. Which means I’ve been dusting off my Python skills and writing way too much JSON.

Honestly? I love it.
It takes me back to how I learned the internet in the mid-90s—tinkering, breaking things, reading source code at 2am. Hands on keyboard. Still my favorite way to learn.

The last few OPs hit a nerve around productivity and effectiveness. Appreciate all the replies—turns out there are a lot of Remarkable fans in this community. I’m a few weeks in and fully converted.

It’s already paid for itself: searchable, digitized notes that I can pipe into my personal SLM (small-language-model).

It’s like giving my second brain a filing cabinet—and a caffeine shot. OP reader, former colleague, and longtime friend, Kevin Ghim (ex-Consensys, Mozilla), pinged me about this after last week’s note. He introduced the concept which is written at length here and mentioned a few companies going after the space: Fabric, Saner, Iki.ai, and even Notion.

I was chatting with my buddy Bruce this past weekend and he recommended I check out a band called Wet Leg. The best way I can describe them is a female-duo indie rock band influenced by The White Stripes, The Strokes, Kings of Leon, and Bloc Party. Apparently they won a Grammy for Best Alternative Music Album. Bruce recommended I listen to Wet Dream (Spotify) and Catch These Fists to get a taste of them. As I write this OP, I’m listening to their albums and I’m digging them. I hope you enjoy them too.

On a whole other topic, another OP reader, Jeff Tarullo (Shopify) sent me one of the better breakdowns and case studies of an influencer marketing campaign. If you are a consumer marketer, you should absolutely read this piece on Fashion Nova. Even fi you are a b2b marketer, you can learn a bunch here.

OK, lets get started. A few fun links below:

And last before we begin, webmaster, err, John Ebbert (founder of AdExchanger) is back writing again, although this time, trading programmatic ads for artificial intelligence’s domination of advertising called Tipsheet. Check it out.

I hope you enjoy the OP! I’ll be taking the next couple of weeks off due to some personal and business travel. But just wanted to say: I see the replies. I appreciate the ideas. Keep ‘em coming.

Be well, do good.
Darren

Your Stock Just Got Tokenized. Now What?

I’ve been into tokenized assets for a while now.

Backed some early-stage personal angel bets like Dibbs (acq. Bastion) and the company that came before Zero Hash.
It wasn’t cool. It wasn’t mainstream.
It was weird. But it made sense to me.

Take a thing, break it into digital pieces, let more people own it. Baseball cards, bourbon barrels, startup shares.
Fractional access, 24/7 markets, fewer gatekeepers.
In theory, it was elegant. In practice, messy.

So when I saw Matt Levine’s latest piece—“The Stocks Will Be Tokenized”—I felt that old itch again.
Because it’s not just theoretical anymore.

Robinhood just launched a platform in Europe where you can buy tokens that represent real shares of U.S. stocks—Apple, Nvidia, Microsoft. You don’t get voting rights, but you get dividends.
And the kicker: they’re talking about adding tokenized shares of private companies like OpenAI and SpaceX later this summer.

It’s one part access, one part liquidity, and a big part "What does this even mean for ownership?"

Levine, in his signature style, doesn’t hype it. He dissects it.
The tension is this: the form of ownership is changing, but the power structure isn’t.
Tokens give you economic exposure—not governance. Robinhood still holds the real shares.

It’s like letting you into the casino but only to play the penny slots.

And yet—
This stuff is going to change how markets work.
Not overnight. Not perfectly. But directionally.

So if you’re building in fintech, sitting on a cap table, or just thinking about how the future of access and ownership collides, here are a few questions I’m chewing on:

  • When shares become tokens, and tokens become liquid, what happens to control?

  • Are we democratizing investing—or just creating a new wrapper for the same old hierarchy?

  • Could tokenized private equity create a secondaries market before there’s even a first?

  • What does LP reporting look like in a world where a Series B position is trading on-chain?

The work we do in the boardroom—capital allocation, governance, strategy—assumes a stable definition of ownership.
But what if that’s the part that’s shifting under our feet?

We’re not there yet. But we’re closer than most think.
And if Robinhood pulls this off in Europe, it won’t be long before others try here.

I’m still watching the space—not just as a former investor in it, but because the next generation of growth-stage companies might raise, operate, and exit under a completely different set of rules.

If curious, here are some good reads/listens:

The Edge of the Idea

I had coffee last week with Vinodh Bhat, co-founder of Saavn and one of the original minds behind [212] Media. Sitting across from him at Tatte in our building at 200 Clarendon, I got that same rush I used to get walking into their office nearly two decades ago. That mix of chaos, creativity, and conviction.

Taken by Vin

Back then, 212 Media felt like a clubhouse for builders—kind of like Betaworks just down the street. Vin and Neal Shenoy ran the studio, spinning out companies like Saavn and LeagueApps before “venture studio” was even a thing. It reminded me of CMGI, the OG incubator I obsessed over in the Silicon Alley Reporter, Red Herring, and Business 2.0 days—where ideas became companies, companies became LLCs, and teams got built around conviction, not slides.

I wandered into 212 sometime between 2004 and 2007—still early in my own journey. I met the founding teams, gave feedback on product mockups, and stayed close with folks like Brian Litvack, who went on to build LeagueApps into a real force in youth sports. Saavn eventually merged with Jio in a billion-dollar deal. LeagueApps recently raised from Accel-KKR. I’ve kept in touch with many of them since.

But here’s what’s been on my mind:
Why does that early-stage energy feel so electric—and why is it so hard to recreate later?

I work mostly with later-stage companies now. More structure. More process. More at stake. But I still crave that early-stage tension—that weird mix of optimism and paranoia. The “we might be onto something, or we might be crazy” feeling. And the truth is, some of that can still be used—even in $800M businesses.

So I’ve been reflecting on what I learned in those early days—and how it still applies.

1. Every big outcome starts as someone’s irrational belief
When I met Vin and Neal, Indian music streaming wasn’t a category. Brian was pitching rec league infrastructure software in a world still dominated by Excel. None of it made sense—until it did.
Later-stage leaders need to borrow that irrationality—especially when carving new product lines or entering new markets. Vision doesn’t scale unless you keep restocking it.

2. Feedback is free. Judgment is expensive.
At 212, they invited feedback constantly—from users, advisors, interns. But they didn’t confuse it with consensus. They knew how to listen without obeying.
That’s a muscle later-stage companies forget how to use. The best leaders synthesize input without outsourcing their judgment.

3. Talent is attracted to momentum, not perfection
People didn’t join those early teams because the org charts were clean. They joined because something was happening.
Too many growth-stage companies recruit with polish. Try momentum instead. Show the mission, the mess, and the movement. The right people will lean in.

4. Central functions should create speed, not slow it down
212 had a studio model that let ideas flow through a system. Today’s later-stage companies often have the inverse—functions that add process but no pace.
Flip the model. Ask: does this function accelerate iteration, or dampen it?

I left that coffee with Vin buzzing—not just from the iced tea, but from the reminder of what it feels like when a company is in motion—before the market notices, before the board weighs in, before the slide decks get made.

I want more of that. Even at scale.

And maybe that’s the real unlock:
Early-stage isn’t a phase. It’s a posture.
Keep building like no one’s watching.

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Against “Brain Damage” (Ethan Mollick) - this goes out to my daughter who says I’m getting dumber for using AI

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