The Upshot
“Do you feel more empathy for the startup founders you interview?”
Since launching Upstarts Media, I’ve heard this question enough to have a canned response ready: a rueful smile and an “obviously!”
It’s been nine months since I did the thing, embraced that it’s time to build, and became another man in the arena.
Being the founder of a media startup and a classic ‘tech’ one are similar in some ways. None of us really pay ourselves, and we have conversations with our own brand’s social media accounts. We get a lot of cold inbound from mysterious software vendors and recruiters.
But whether you’re sized more like a small business or an AI unicorn, the emotional rollercoaster of being a founder is probably the same. At Upstarts, I vacillate daily between the exuberance of empire-building, and questioning what it means to really exist.
Upstarts has carved out a niche as a trusted startup-focused voice in what our friends at TBPN call Post Legacy Media, or I think of as independent or “new” media. In nine months of operation this year, we published 80 stories, co-hosted 12 events across 3 states and 2 continents, spoke on countless podcasts and panels and mucked around at an IPO. We worked with great partners like Brex, Mercury, Notion, Structify and Vanta. We gave out some cool hats!
At the same time, Upstarts is a very small business with one full-time employee: me. Yes, we’ve also got Margot as social media manager (dogged work ethic, takes too many naps) and our MVP adviser, Natalie Sportelli. We’ve brought on great people to work part-time on our branding, biz dev and upcoming podcast. But I continue to say “we” in more of an aspirational sense.
We’re a lean operation by choice. Upstarts is deliberately a revenue-driven business, dependent on subscribers like you, to better control our destiny and make sure we’ve nailed product-market fit before we scale. If AI startups can potentially reach $1 billion with 1 employee, why can’t a media startup reach $1 million?
And we already have a ton to be excited about in 2026. In addition to our regular programming, I’ll be hitting the studio to tape episodes of The Upstarts Podcast. Later in January, Upstarts will publish our first magazine-style feature profile, about an under-the-radar Silicon Valley startup unicorn and its media-shy but influential CEO.
As we steam ahead into all of those upcoming projects, I forced myself to slow down for just long enough to read our Audience Survey responses, and go through Substack’s story analytics, to see what resonated with you, our readers, in 2025 – and set 6 resolutions for Upstarts as we look ahead to 2026.
The TL;DR:
Bangers only
Say ‘no’
Refine our voice
Remember why we (sh*t)post
Convene IRL
Have more fun
Before I continue, I must add that it’s not too late to take 20% off a paid monthly or annual subscription via our end-of-year sale. Whether you’re already a supporter or a future one, thank you for reading this year!
1. Bangers only
The Power Law doesn’t just apply to market winners and venture returns: it’s a Substack thing, too.
Every Upstarts story has a healthy audience floor. But it’s a handful of big hits that can drive a hundred-plus paid subscriptions, or tens of thousands of extra views.
Our top story of 2025, a June scoop revealing a then-stealthy startup founded by three OpenAI employees that had raised $20 million, drove our second-biggest revenue day besides our launch in March. Two of the other top five stories came in December, a good sign!
Upstarts Top 5 Stories Of 2025
Scoop: 3 Ex-OpenAI Staffers Raise $20M For New Startup Applied Compute (June)
The New Vibe Coding Startup Taking Aim At Lovable (And Everyone Else) (December)
Deep Dive: As Smaller VC Firms Build AI Tools To Compete, Founders Should (Mostly) Benefit (December)
Inside The Stealthy European Defense Tech Startup Raising $100 Million (July)
Handshake’s CEO Declares ‘Refounding’ Of His $3.5B Startup, All Around AI (October)
Those stories sync with our Upstarts audience survey results. Readers said they most enjoyed reading startup CEO interviews, in-depth features and profiles, then trend stories and analysis. Those were also the stories they said they’d be most likely to pay to read.
Features and trend stories take a lot more work, so it’s a relief that Upstarts readers are savvy and value them more highly, too.
They’re also hard to publish too frequently, given the extra reporting required. But the data is heartening: Upstarts needs to keep taking these big swings even more often. When they land, they can produce the outsized returns that really grow our audience – and our revenue, too.
That will require more efficiency and prioritization, as well as creativity to keep on the zeitgeistI’m confident we can lean on our audience and network better, and ruthlessly focus, to ship more bangers.
Resolution: Do whatever it takes to publish more big stories.
2. Say ‘no’
One way to carve out more time for those big swings: raising the bar on funding round coverage, where we probably got a bit carried away in 2025.
In March, I wrote in our intro post that Upstarts would publish curated funding exclusives on a monthly basis; quickly, that increased to nearly every week. That wasn’t out of some desire to flood the zone with Upstarts content, or to compete with higher-volume ‘trad media’ publications like TechCrunch. They were simply straightforward stories that could be scheduled out, helping Upstarts to publish consistently.
I’m proud of the quality of our Upstarts exclusives, which ran the gamut from new businesses with single-digit millions raised to $100 million-plus. I hope our partners were proud to sponsor the newsletters showcasing many of them, and that you, our readers, found them interesting and fair.
But the harsh reality is: there’s a hard cap to such pieces. Supply for startup funding coverage continues to outpace demand. Startup builders, PR reps and VCs are eager to read and share stories about their network’s startups. A stranger’s startup? Not so much.
Upstarts will continue to proudly cover startups from inception through IPO, and I’ll always personally gravitate towards weird, contrarian or underrepresented founders. But we have to get smarter about it.
Maybe that means more brevity in some of our early-stage coverage, or we save more in-depth reporting about a funding round for a more special, curated monthly edition closer to the original Upstarts road map.
I’ll be experimenting with this one, and welcome your ongoing feedback. I might even dig the tips@upstartsmedia.com email inbox out of its current radioactive state.
Resolution: Be smarter about our funding news and early-stage exclusives. Less is more.
3. Refine our voice
Upstarts isn’t a personal blog – we’re building a hub for trustworthy and fun coverage of the startup ecosystem.
But we’re also not a wire service or newspaper, in tenor or tone. Many of the newsletters I enjoy reading the most myself, like Eric Newcomer’s, Platformer, Big Technology, and Sources in tech, or Feed Me, After School by Casey Lewis and Emma Apple Chozick’s in culture, have embraced more of a personal tone.
Upstarts is named the way it is in part because I want this to be a community, with readers comfortable talking with me and meeting each other and sharing ideas.
To do that, I think it’s important that you all know and trust me, and anyone else who might take up the Upstarts banner. Hiding that behind a faceless house voice doesn’t help anyone.
We’ve dipped our toes a little bit in this regard, like when we wrote about the latest in pet tech and showcased Margot, but there’s much more we can do to be “voicey”, whether it’s in a column format, or simply intertwined throughout, without compromising our reporting.
Resolution: Be bolder about finding and using our own voice to benefit our coverage.
4. Remember why we (sh*t)post
For all the time it takes to post Upstarts stories across social – X, LinkedIn, Bluesky and Threads, maybe even an Instagram story if we’re feeling wild – and the hours spent checking notifications and ‘brand-building,’ you’d think social was a key driver of our growth.
In reality, it’s important – but not how you might expect. Social can drive discussion and create awareness, particularly among tastemakers and industry leaders. It does not drive readers.
Substack’s analytics are good about showing what sites drive traffic, and for Upstarts’ top stories, the answer is not much. Using the Top 5 from before as a sample, Twitter/X only drove 10% of traffic to our OpenAI scoop. LinkedIn has pleasantly surprised with its large-sized reach and quality of comments and discussions on Upstarts story points; it’s also driven a meaningful number of paid subscriptions. For each of our top 5 stories, it drove less than 5% of traffic.
Looking at our overall Upstarts traffic, LinkedIn and X are important, but they’re dwarfed by newsletter reads, direct link sharing and Google Search. We can caveat this partly by the fact that Upstarts doesn’t have a sophisticated social strategy (though we are looking for some extra social support next year).
It’s a safe bet that Upstarts will post more, not less, in 2026. But it’s also healthy – and smart business – to remember that social is more valuable for brand awareness and vibes than actual readership.
Resolution: Embrace social media for what it’s good at – which isn’t people reading specific work.
5. Convene IRL
When thinking about favorite moments in the Upstarts journey this year, many of them were when we got to leave the keyboard behind and engage with you, the Upstarts community, face to face.
Whether it was at our launch party in New York, our reader event in San Francisco, or our Tech Week founder events in both places; our big spring event in London; or our two-day tour around Utah; or at the various dinners and small meetups we co-hosted this year in-between; we left every meetup feeling energized.
I know intimately now how busy founder life is, and how much of a distraction it can feel to stop by endless events. Upstarts events are designed with that in mind: tactical, handpicked, maybe even a little cathartic.
There’s so much more we can do in 2026, though, starting with a more consistent cadence to our dinners and reader meetups, then expanding out to reach startup communities in more geographies. We’ll be back in London in February, and readers have suggested Austin, Boston, Chicago and Paris. We welcome such feedback, sponsors, and any local partner introductions.
Resolution: Let’s get together more, not just because I’m a solo founder without coworkers.
6. Have more fun
Nvidia’s Jensen Huang is a master of soundbites, and one recent quote of his struck a chord:
“A healthy dose of ignorance and irreverence for how hard something is, is an essential quality of startup CEOs and founders.”
After spending my entire career talking to founders and startup CEOs, it’s hard for me to turn on that blissful ignorance. I’m acutely aware of how difficult of an industry I’m building in, how fractured our information, and how many things can always go wrong.
For me, the bigger challenge is to put the restlessness and pragmatic worrying aside more, because: Upstarts is doing great, and I am so lucky to make money building the place I want to work.
My natural instinct is to dwell on the 99% of the journey we haven’t reached yet. Writing about so many hyper-growth companies (even knowing that such stories are seldom so straightforward), it’s hard not to set the same high standards.
When I think about the most fun I’ve had with Upstarts so far, it’s been shipping new and weird projects, gathering curious people, and above all, spending time exploring the possible with those irreverent founders that Huang also loves.
My bet for 2026 is that if we’re really excited about something Upstarts is cooking, the wider community will be, too. And if you can tell I’m passionate about a story, or our podcast, it’ll be contagious. While there are important and serious conversations to be having in the startup world, let’s take ourselves a bit less seriously along the way. All the rest will follow, with good execution and enough time.
If that sounds exciting to you, too, I hope you’ll reach out with ways to collaborate, or share Upstarts with other people in the year to come. If it’s something your company would want to stand beside, we also maintain a Sponsorship Interest Form.
Resolution: Build Upstarts into a place that’s fun to work – even if it’s still just me doing so – and remember how cool it is that I get to think about startups and new possibilities every day.
Lol “we have conversations with our own brand’s social media accounts”
Who won the arguments?!?
Loved this, Alex! Thank you!!