Is your favorite startup CEO terminally online?
A quirk of hosting a podcast is that you quickly learn the internet habits of your guests. Some will be up-to-date on every subplot of Silicon Valley internet drama, prepared to riff. If you want to know their hot take on a topic, it’s usually as easy as pulling up their social media accounts.
These are my people, like CEO Shensi Ding, who spoke at an Upstarts event in June. Her startup, Merge, offers infrastructure to help businesses connect to apps and AI tools faster and cheaper. But on X, you’ll find her gonzo posting about everything from model routers to overhearing tech bros on cringey dates.
Then there’s Basis CEO Matt Harpe, who joined The Upstarts Podcast as our final guest of Season 2 a few weeks ago. It fell on Harpe’s co-founder, Mitchell Troyanovsky, to share that conversation on X and LinkedIn when it dropped.
“Listen to Matt (who does too much real work to have a twitter) on what Basis is doing for accountants,” he posted.
I thought about that line frequently this past week, as the Highly Online startup community piled onto a few trending topics: Anthropic making seemingly quite a lot of money; Stripe finally acquiring OpenRouter after a month of rumor and speculation, a new AI assistant agent, Instinct, delighting with its ease-of-use and worrying with its data retention policies.
You can argue that all of those stories have big-picture implications for a wide swathe of people. How Anthropic and OpenAI fare commercially can affect consumers and companies building on top of them, and two potentially massive, bellwether IPOs. A frenzy of interest in model routers, from Stripe, Ramp and others can speak to a moment where businesses are grappling with the costs of using such AI tools. And whether it’s through Instinct, or two other tools getting discussion online – SpaceXAI’s Grok Bot and Town – squint and you can see the path to mainstream AI assistants feeling a little more direct.
But for most people – and even most directly in the startup ecosystem – is knowing more about all of that, and faster, creating some advantage? Or is it scratching a different itch?
The question has a lot of relevance to Upstarts, considering we often publish stories about startups before they’ve become internet main characters, and as I continue to think about the balance of what coverage the startup ecosystem needs versus the coverage it wants.
I’ve had fun diving into a few startup stories in unexpected places in recent weeks, like Henry AI bringing AI to commercial real estate; Ambrook building the QuickBooks for farmers and other physical-world businesses; and Clair, providing a non-predatory alternative to payday loans.
I’m proud of those stories, and hope you’ve enjoyed them. I’m also aware that Upstarts would probably be growing our subscriber base faster if we cynically chased the same trending stories as everyone else. But what would be the fun in that?
On Thursday night, as last-minute, lawyer-driven intrigue delayed an upcoming story, I decided to try an experiment: write a column about some of these thoughts bouncing around my brain. So I pinged Ding and a few other Highly Online tech folks to ask if they feel like they’re getting real benefits from long shifts in the content factory – or simply indulging in 2026’s flavor of brain rot.
“I am massively torn. Very unclear if it’s worth the tradeoffs,” DMs one investor on X. “Good for the brand, bad for the sanity and focus.”
“Maybe I’m psycho, but I f***ing love it,” Ding texts.
My takeaways from those chats – from how AI adds urgency and psychosis, to how everything is a prediction market now – below, featuring Shensi Ding, Olivia Moore, Ken Wattana, Yoni Rechtman, Bilal Zuberi, and Jane Manchun Wong.
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Moving at AI pace
At Merge, Ding seems skeptical that a founder in AI, particularly, could not be fully plugged in.
“I think things change so quickly compared to before, you need to know what’s happening every f***ing day,” she writes. Still, she tries to focus on a few areas of particular importance – infrastructure, AI assistants, and AI governance – while leaving updates on hardware and data center issues for her husband, who works closer to those topics, to fill her in about.
“Anyone who has PMF [product market fit] has it for max six to 12 months, and is required to continuously keep releasing bangers,” Ding argues. “Versus before, you could have dominance for three to five years, and rely on that.”
Trendspotting as value-add
At a16z, investor Olivia Moore says that her online presence is about serving as a curator for her portfolio founders on new products and micro-trends.
“This could all just be cope for my ridiculously high screen time :)”
“I feel like it’s the least we can do to have an understanding of what’s going on in the broader ecosystem to the extent that it can be helpful to our founders,” she writes to Upstarts.
Moore still subscribes to the idea, amplified by Elon Musk when he acquired Twitter in 2022 and later renamed it X, that the site serves as tech’s “digital town square,” providing exposure to new data points and arguments.
“This could all just be cope for my ridiculously high screen time :)” she adds.
An outsider’s way in
“Not knowing what’s happening may be a badge of honor,” notes the founder Ken Wattana – a sign you’ve made it enough not to be hustling.
Wattana, the founder and CEO of agentic payments startup Conto, says that he monitors ‘Tech Twitter’ similar to how finance professionals have historically watched their Bloomberg terminals. Being so online helps him to understand Silicon Valley dynamics, and what insiders might find compelling.
“I’m not in the inner circle, so it’s my way of trying to be as informed as possible,” he says.
Posting frequently has also helped drive a mix of inbound interest for his startup and a feeling that he’s in on the joke. “I’d like to think it helps with distribution and just being ‘known,’ Wattana writes Upstarts. And while his “shitposts” may not reach prospective buyers directly, “It is fun to see notable VCs and founders engage with them.”
Anything goes
Bilal Zuberi, founder of Red Glass Venture, says he’s often online for two reasons: to be more accessible to startup founders; and to encourage them to feel comfortable to be authentic in public, “vulnerabilities included.”
There’s a darker side to this, too, though: a devaluing of “real, serious journalism” means that anything is fair game to say, Zuberi adds. “People are rewriting history in real time, and those with big, loyal followings seem to think that insulates them from criticism – however deserved it may be.”
He points to Turner Novak’s satirical tweet from earlier this past week, in which the investor and podcast host jokingly announces he’s making a full circuit of non-journalistic, often investor or tech-owned ‘new media’ properties.
Everything is a market
Yoni Rechtman, a partner at Slow Ventures, sees the irony in investors who back early-stage startups for a decade or more acting more like day traders on social media.
“It’s just another symptom of how private markets are coming to look more and more like public markets,” he says.
And it feels like no coincidence that the rise of sports betting and prediction markets has dovetailed with increased interest in trading startup equity before these companies go public. It used to be that revenue milestones or new valuations were indirect, longer-term signals. Increasingly, as Robinhood and others look to provide financial vehicles for retail investors to gain exposure to tech unicorns, they’re potential trading signals.
Can’t get into Anthropic or OpenAI’s upcoming IPOs? You can trade them indirectly, through markets on Kalshi and Polymarket for who will go out first, or at what price.
For startups and investors, Tech Twitter can provide a pulse, or a view of emerging consensus, but fewer immediately actionable insights, Rechtman adds.
“I think it’s generally very useless to try and send tweets and articles to my founders, being like, ‘Did you see this?’” he says.
Avoiding X psychosis
Late last year, writer and researcher Jane Manchun Wong says she found herself too plugged in – unsustainably online.
So she set up her own feed to syndicate posts from accounts and topics she cares about, like a new-look RSS feed. She also leans on her subscription to Techmeme to help her see just enough about a new story or controversy, without getting sucked down a rabbit hole.
“I’m not going to click thousands of posts. I’m just going to look into it, and then think, ‘Oh, makes sense,’ and then move on,” she says.
As people spend more time talking to AI coding agents or assistants, their disconnect from reality could grow. While Manchun Wong still checks X frequently for “chatter” and general sentiment, she’s also changed things up by using her account to post new restaurants local to her in the Bay Area (what she sees as influencer-free, grassroots promotion) while prioritizing more in-person meetups.
When Ding calls herself a “psycho,” it’s hard to know how much she’s joking. But Rechtman seems prescient when he warns that too much time on Tech Twitter – much like in ChatGPT or Claude – could be dangerous.
“It is increasingly important to have an actively maintained cognitive security and cognitive hygiene,” he says. “Because the meme cycle and the feverish breaking news coming out of startup land right now will truly break your brain.”