Hey friends of Soapbox! Welcome to our November newsletter. 🥂
We’re entering November with elections, daylight savings, and even the first snowfall for some of our Midwest friends. Hope you had a fun (and spooky) October, and are settling into cozy season.
When do you start decorating for Christmas/The Holidays?
Soapbox of the Month
2nd Hand Insights
passed along learnings are like hand me down clothes
Written by Maria
One of the first lessons in venture “pattern matching” is to back founders with domain expertise. These are people who have lived, breathed, and worked in the problem space they are building in. A former HR leader at Facebook building a payroll tool, for example, starts with a sharper reference point than if I started cooking up the next Rippling competitor.
That said, great companies are often built by outsiders. With AI lowering the cost of building, the goalposts have moved. I’d argue there’s little lasting “moat” in tech today (more on that another time). What matters is speed and distribution, and this domain knowledge functions like seeing the puzzle before everyone else. You move faster from A to B because you already know which pieces click.
Spencer Bledsoe from Survivor, who memorized most likely puzzles prior to his season, solved this one in 15 seconds.
When founders build in an unfamiliar space, they often try to close the gap with “second-hand insights”: advice and patterns borrowed from people who’ve been in the industry. Helpful, yes, but second-hand insights are like hand-me-down clothes: a step behind the trends and a bit ill-fitted. Second-hand insights carry the original owner’s context, and what worked under one set of constraints, incentives, and market timing may not "size" to the present.
Relying solely on second-hand insights keeps founders working at a constant disadvantage. You’re waiting to learn the hard way or chasing someone else’s lessons. There’s already enough learning the hard way in startups. The thoughts of others (advisors, investors, etc.) can’t substitute for the founder’s own lived context; without it, those insights don’t compound.
he was an advisor with more equity than the CTO for "insights"
This is why, as VCs, we hesitate to back teams without a unique angle or background, not because those without the domain experience can’t win, but because at the pre-seed stage, proprietary insight is usually what creates founder conviction. And founder conviction is what creates our conviction that the company could derive a billion-dollar outcome.
1st Hand Insights:
“At X, I saw/learned X, that influenced X, which I am now building with X”
Second-order effects: Clear articulation around early vision & product
“I want to move from X GTM to X GTM just like I did at my previous company/employer.”
Second-order effects: Speed to market, robust pipeline of prospects or pilot customers
“What most don’t understand is X, because I know this, I am able to do X thing 10x better than X.”
Second-order effects: Speed of iteration, revenue ramping post launch
2nd Hand Insights:
“Our advisor shared that X was their experience, and so we are trying/doing/experimenting with X.”
Second-order effects: Slow speed to launch, multiple versions of product (V1,V2,V3)
“The sales cycle is long in X, so we are doing X, because it is how X person did it at X.”
Second-order effects: Quick no’s from prospects, prolonged sales or implementation cycles, customer feedback that the problem isn’t “urgent” enough to solve for at this time.
“X industry has been historically slow to adopt X, because X” (when broad, non-specific**)
Second-order effects: Lose to the incumbent or new solutions, slow growth, no customer network effects
All of the above is not new – but the gap is widening. I’m watching it in real time. The world is stochastic, and it's better to have your own framework to build on than wait for someone to share theirs.
CAREER 🧑💻
One of our FAV podcasts, Per My Last Email by Morning Brew, recently dropped an episode titled 5 Life Experiences That Unexpectedly Make You Better at Your Job.
Hosts Kaila and Kyle (a fellow Minnesotan!) walk through the personal and professional experiences that have shaped their growth. We loved it, so we pulled together a quick summary of the five themes they highlight:
1. Failure
It sounds cliché, but failure truly is fuel for growth. It teaches you to take feedback, build resilience, and come back stronger.
2. Build an identity outside of work
Have hobbies!! Try new things. Learn for the sake of learning. The best insights often come from experiences that have nothing to do with your nine-to-five.
3. “Just do things!”
Agency is one of the most powerful traits you can build. When you take initiative and make things happen without waiting for permission, you stand out. People are drawn to those who create momentum and bring ideas to life.
4. Multicultural experiences
Travel, meet people, and immerse yourself in different ways of living. Expanding your worldview makes you a better teammate, communicator, and problem solver.
5. Unexpected networking
Some of the best connections come from stepping outside your usual circles. Send the cold email. Go to the random event. You never know where it might lead.
Go listen to the pod and their other episodes - they have a lot of great content on career. 🎉
CULTURE 🌈
Alix Earl & Val Chmerkovskiy on this Season of DWTS (where our votes go every week)
🪩💃 Dancing with the Stars is cool again 💃🪩
What was a comfort show for older audiences, with a median viewer age of 63.5 in 2022, and a cast list that felt like “where are they now” in sequins, has now turned into a must-watch every Tuesday for us and our Gen Z friends.
What changed in 2 years? Gen Z began meme-ing routines on TikTok. Producers leaned in and cast creators who already know how to go viral (Charli D’Amelio, JoJo Siwa, Harry Jowsey, Alix Earle), athletes still in their prime (Iman Shumpert, Ilona Maher, Stephen Nedoroscik, Jordan Chiles), and reality leads we are currently arguing about in group chats (Whitney Levitt, Dylan Effron). The ballroom did not fundamentally change. The incentives did. Every dance is now built to live twice: once on TV, and again on TikTok.
The renewed obsession with DWTS isn’t all about the better casting or smarter social strategy. After a decade of on-demand, watch-whenever content, DWTS offers something very simple. Show up at a specific time. Watch the same thing everyone else does. React together online. In a culture that feels fragmented and extremely online, that kind of scheduled, collective experience starts to feel valuable again. As Glamour put it:
What once felt a little cringey now feels knowingly campy, a subtle but crucial difference. The show is still sparkly and over-the-top, but it’s owning it instead of being embarrassed by it. In a cultural moment where pop-culture maximalism is back … the kitsch of the ballroom doesn’t seem so analog. The stars genuinely seem excited to be there, and the camaraderie is more palpable in recent seasons, which sends viewers a message that this is low-stakes fun and maybe even a cool thing to do—because anything is cool these days if you own it.”
CAPITAL 💸
Ever wondered when most founders actually close their rounds?
According to Carta data from 2016–2024, the week of December 15 consistently sees the highest volume of signed venture deals.
It’s likely the holiday rush to wrap up in-process deals before year-end, paired with the natural close of the fall fundraising season. Other peaks tend to happen in late March and late April, while the first and last weeks of the year are nearly silent.
Deals happen year-round, but mid-December is when many deals cross the finish line.
From Our Feed to Yours
Tweets, Memes, and other things from our feed that gave us a laugh.
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