This week, we’re talking:
Why successful VCs need a time-intensive hobby 🎨📸🎸⛳ (Hint: It’s not just for fun.)
The paradox of founders 😈💥 (Brilliant, driven… and sometimes their own worst enemy.)
VCs scratching their heads over why US-based AI startups needed so much money—while DeepSeek did it on a budget 💸💸💸
The OG IP thieves calling out IP theft 💰🚨💰 (Irony levels: off the charts.)
Grief apps are making bereavement support more accessible—but at what privacy cost? 🪦👀
How unpermissioned data is quietly sabotaging your competitive edge 🧹🪣
Let’s get into it…
My Take:
I’ll take your questions now…
(Introducing Mail Bag, a new section of this newsletter where I answer reader questions)
In response to last week’s post, a reader commented: Do any of the lessons about balancing autonomy and oversight translate to the investor space? It’s a great question. Founders and investors share many of the same struggles when it comes to walking the tightrope between giving autonomy and maintaining oversight. But here’s the rub: founders are in the trenches every day. Venture capitalists support the cause, but they’re not taking direct hits on the field.
Let’s start with a reality check: While a few successful VC’s are former operators (and relished hands-on operations while they held the reins), venture capitalists are not operators. Career VCs generally don’t know how to build a culture of collaboration. Their job is to find and fund the real operators—the people who can rally a team, ship a product, and keep the wheels on the bus. Ask a VC about their firm’s internal dynamics over a weekend martini or two, and they’ll probably admit it’s rough sledding: politics, palace intrigue, jockeying for carry. If you’ve seen VC dysfunction, you know first-hand that a venture capital partnership is an outright abuse of the word ‘partnership.’
Startups have structure—metrics, KPIs, performance reviews. VCs? They have offsites. Offsites in bougie locations with vague agendas, vague goals, and lots of really delicious wine. And look, I’ve got to be fair: you can’t measure VC performance the same way you measure a startup employee. It takes at least a decade to figure out if a VC’s bets are going to work. Still, the contrast is stark.
For all their perceived power, venture capitalists actually have a pretty limited toolkit. They can hire the CEO. They can show up at board meetings and critique the CEO’s craftsmanship. They can try to nudge the CEO into following their advice. And they can fire the CEO. That’s about it.
The Paradox of Founders
Here’s the trouble: you want a founder with demonic intensity—someone who thinks they’re on a mission from God. The type of person who slays dragons and builds billion-dollar companies. But when they’re wrong? Holy hell. Watching someone with that level of conviction drive a company off a cliff is like watching an F-22 pilot crash a $25 million jet. And as a VC, you’re strapped in the back seat, powerless to stop it.
This is why I’m not a venture capitalist. I just don’t have the temperament to be a successful VC, which is a big part of the reason I pursued the startup studio model at super{set}. I want to empower and invest in a new generation of entrepreneurs, but I want to build alongside them. I need to have my hands on the ball. A lot of serial founders look at what VCs do and think, “That looks easy enough,” and they start their own shops. But most of them fail because demonic intensity—the very quality that makes them great founders—doesn’t work when it comes time to relinquish ball control, let someone else play the game, and suggest plays from the sideline.
Having been lucky to work with a number of great VC’s and a few not-so- great ones, I’ve accumulated a reasonably informed perspective as to how an effective VC manages the interplay between giving and claiming authority.
Balancing Autonomy and Oversight as an Investor
Get a Time-Intensive Hobby
A legendary VC famously advised his younger partners to pick up a time-intensive hobby. Why? Because if you try to helicopter-parent founders, it’s going to end badly for everyone. Founders need space to do their thing.Hire Well and Then Trust
Your most important job as a VC is to bet on the right people. If you don’t trust the founder to make good decisions, you’ve already lost the game. Your job is to support them, not micromanage and second-guess them.Provide Guardrails, Not Chains
Be the bumpers on the bowling alley, not the bowler. Offer advice and resources, but let founders execute a vision you fully understand – which was presumably the basis of your decision to fund them in the first place.Know When to Intervene
Sometimes, you’ll see a founder heading for disaster. When that happens, step in thoughtfully and with concurrence from other investors. But always keep the perils of intervention and the power of evidence-based persuasion firmly in mind.Get Comfortable with Discomfort
Investing is messy. You won’t have all the answers, and you won’t always be in control. See point 1
As a VC, you’re not the gladiator. You’re the patron in the stands, cheering them on, maybe tossing a coin for luck. You can fund the gladiator’s training, give them the best sword money can buy, and shout encouragement from the stands. But once they’re in the arena, it’s just them and the lion. Your job is to pick the right fighter and trust them to deliver.
Thanks for the question,
. Have a question you want me to answer in a future post? Drop a comment or send me a message.Around the Web:
They Invested Billions. Then the A.I. Script Got Flipped. via NYTimes 💸💸💸
For two years, venture capital firms have been engaged in a funding frenzy, pouring more than $155 billion into A.I. start-ups between 2023 and 2024, according to PitchBook, which tracks start-ups. Two of those A.I. companies — OpenAI and Anthropic — have raised $24 billion and $16 billion with the goal of building A.I. that is as intelligent as humans. OpenAI’s valuation has hit $157 billion — more than Pfizer or Citigroup — while Anthropic’s valuation has reached $20 billion. What DeepSeek did has now called that funding fever into question. If a Chinese upstart can create an app as powerful as OpenAI’s ChatGPT or Anthropic’s Claude chatbot with barely any money, why did those companies need to raise so much cash?
OpenAI says it has evidence China’s DeepSeek used its model to train competitor via FT 💰🚨💰
OpenAI has evidence that China’s DeepSeek used OpenAI’s models to train its competitor, David Sacks, Donald Trump’s newly appointed AI and crypto czar, has said. In an interview with Fox News, Sacks said there was “substantial evidence” that DeepSeek had used a technique known as “distillation” to build its AI models.
Grief Apps are Turning Death into Data via BBC 🪦👀
In soothingly serifed fonts and tasteful colour palettes that are muted but never sombre, Untangle and a number of other new "grief apps", including DayNew and Empathy, seek to remake mourning for the modern era. They have the potential to democratise access to support that can otherwise be hard to find. But in doing so, privacy experts say these apps are introducing corporate technology – and all the problems of the digital age – into the vulnerability of grief.
News from the Hive:
We did a study on dirty data, and the results should make you nervous.
That might sound like a BuzzFeed headline circa 2012, but nothing much has changed. The main difference is that AI has upped the ante on sources and uses of data everywhere



You can read the full report over at Ketch, but here's the BuzzFeed headline Tl;dr to stay on theme: You're building your AI on dirty data, and you probably didn't even know it.