Insecurity is the enemy of improvement
Plus, rebuilding lifelock for a scammy future, Figma, dinner with designers, and lots of events
Since the pandemic, every summer has been less “summer-y” than the summer before in venture land. Used to be there was alpha in just showing up to work in July, now it’s probably 90% as busy as the rest of the year. You can work from anywhere so you can always work!
Everyone loves talking about how "chips on shoulders put chips in pockets." Bear Stearns used to seek out new hires with “PSD or poor, smart, and deep desire to get rich”. They win because they have to.
This is right and is a great case to bet on people who didn’t start on 1st (or 3rd) base or have been otherwise overlooked. People with something to prove and are motivated to outwork and outcompete through the hardest parts of the journey.
It’s very easy to confuse mere insecurity for a chip on the shoulder. And insecurity is the mind/company/morale killer. Avoid pathologically insecure people at all costs. Insecurity leads to overcompensation (you know what they say about guys with big trucks) and a tendency to externalize problems.
Pathologically insecure people depend on constant external validation; they struggle to incorporate feedback, bounce back from challenges, and manage relationships (with talent, customers, and capital). Every slight is personal and deeply cutting and therefore must be fought and rejected rather than considered dispassionately. In numbing themselves to critique and reflection, the most insecure people sabotage their own pace of learning and improvement.
Yes, everyone (who isn’t a robot or a psycho) has some measure of insecurity, anxiety, imposter syndrome, etc. If you don’t, you’re either lying to yourself (self-ignorance is the other mind killer) or you have a wildly overinflated view of yourself (and no one is perfect). It’s fine to cop to that.
Obviously doing anything really special requires some degree of irrational self-belief and vision. But we can all recognize the difference between self belief in the face of overwhelming odds and something darker.
Identifying this and distinguishing it from its positive counterpoint (profound work ethic, motivation, and a chip on the shoulder) is really important and really hard. I’m still trying to figure out where the line is and what is just ex post facto rationalization/categorization. For now, my best approximation is assessing (or at least paying attention to) motivations and self-awareness/self knowledge as leading indicators. If nothing else, they’re things I’m trying to cultivate in myself.
In the future everything will be AI and fake. Time to rebuild Lifelock/Norton.
AI is opening up massive new surface area for fraud and scams, and totally novel new vectors by which to perpetrate them. Identity theft, viral hoaxes, pig butchering, blackmail, romance scams, etc. are all going to go exponential in the next few years. Modern problems require modern solutions; obviously you need a healthy immune system (cogsec) but where are the vaccines?
Gen Digital (which owns LifeLock, Norton, Avast, etc.) does over $3B in revenue and over $1B in net income. It's the biggest names in consumer privacy, identity, and fraud prevention and they are not going to win this. So why not you?
The whole business mostly consists of bulk buying to help settle data breach lawsuits, and subscriptions from people who forgot to cancel. Lifelock et al is in the middle innings of managed decline.
There’s an obvious opportunity to rebuild and remarket consumer fraud prevention for the post-AI-everything-is-fake world we’re streaming toward. In the past, when people tried to rebuild LifeLock, it was mostly just LifeLock with better design. Now we can actually build the product better:
Is this phone call fake? Is this text a scam?
Record my screen to warn me before I do something dumb
Tell me how I'm most likely to get scammed and what steps to take first
Pen testing so I don't fall for the real thing
Alert me if my account is compromised before I realize it myself.
I don’t know what all the features can/could/should be - but you do!
We are often our own worst enemies online. We need to be nagged and helped and calmed down. We need guardrails and assistance that is always on and always helping. This is quietly already happening at the top of the market but there's no mass market, easy-access product here yet.
I Read
Goodbye Gentle Parenting, Hello ‘F—Around and Find Out’ - WSJ. I don’t really have any strong POV parenting (I don’t have kids!) but I’d like to imagine that I will be pretty FAFO with my own kids one day. Those were the best, most valuable parts of my childhood. My parents let me get into a lot of trouble, figure stuff out, and suffer some (natural) consequences from time to time. I’d like to think I’ll do the safe
Behold the first AI-native investment bank - Financial Times. Cool story about a Offdeal which is an investment bank built for small biz transactions. Use lots of AI, be more efficient, be able to do smaller deals, win market share, etc. It seems like I got this one wrong (time will tell of course). When I met Offdeal I was probably too focused on owning the businesses (“if you can do all the deals why not buy the targets yourself”). What I failed to grasp/appreciate that they were owning the business - the bank! I already had this on my list of things I regret/would come to regret passing on. One of those instances where the team was clearly great and I was quibbling over details. It’s a long journey of course but it seems like the initial story is going great. Congrats to Ori and the team! Mea culpa.
Microsoft’s Rivals Lean on AI to Pry Away Longtime Customers - The Information. The “AI will reduce switching costs” story is starting to play out. From The Information, “It isn’t clear who will come out on top as enterprise app providers go after each other’s customers, but chief information officers say they’re already saving money as software switching costs fall. That’s especially true for older businesses that can use AI to move away from proprietary software sold by the likes of Microsoft or Salesforce in favor of open-source alternatives or competing apps.” No - it is clear! The winners will be the customers (duh) and the people managing the transitions (the system integrators, ETL platforms, etc.). Read more in The Complexity Crisis. The cost to move will go down and so more moves will happen.
The Largest Arbitrage in Technology. - Evan Lyseng. This is a nice piece on the whole trend of AI rollups and vertical companies. Very thoughtful and rigorous.
More takes
What we learned from dinner with 12 product designers. The big takeaways were 1) pitching demos not memos in the age of vibe coding 2) teams are getting really senior/top heavy as they move to become reviewers, not producers (RIP junior talent) and 3) domain experience is becoming much more important for designers to contribute. Fun time with folks ranging from big tech, to growth stage, to research labs, and independent consultants.
The Figma IPO was obviously a huge win for a bunch of folks (congrats, genuinely) and will now inevitably set off a round of discourse about the IPO market being “open.” But the IPO market never closed! It just sometimes becomes more tolerant of so-so or mediocre businesses. A great business like Figma (approaching a $1B of topline, profitable, growing fast, great team, good-to-great AI story) could go public in all but the most frozen markets.
Engineering Dinner
I’m hosting a private dinner for senior engineers in a couple weeks with my good friends at Work-Bench. I have a couple seats left for some really sick engineers in NYC.
If you or a friend wants to come, reach out and I can see if it’s the right profile.
Conference
In October I’m hosting the SF version of my annual NYC mini conference for young partners, principals, and emerging managers. This is an invite-only setup but I’m always down to meet new people, especially if they’re referred in from people I know/like/trust.
In May we had an awesome group together in NY and it’s gonna be a good one again.