A New Kind of Startup is Coming, Don't "Fake It Till You Make It", and more!
Everything we published this week
Apr 23, 2023 · 6 min readUpdated Jun 26, 2026
Hello and happy Sunday!
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Now, onto the articles!
A Few Things I Believe About AI
Dan Shipper / Chain of Thought
AI has felt like riding a rocket for the past six months. Given the fast pace of progress, Dan takes some time to reflect on what he believes. He comes up with three theses that govern his work at Every and beyond:
- Knowledge orchestration is the most significant bottleneck for AI applications
- Startups integrated end-to-end over a process will be dominant
- AI will make progress where traditional science has struggled due to its ability to make predictions without requiring explanations
If you want to get a handle on where AI is going, read this piece.
A New Kind of Startup is Coming
The dawn of AI-native startups is upon us, and they're set to reshape the business landscape. Smaller, faster, and weirder than their predecessors, these startups will leverage AI to achieve staggering scale with minimal manpower, possibly even going public with less than 100 employees.
Nathan explores this new organizational form, examining how AI will assist in areas like building products, working with data, and automating sales, ultimately changing the role humans play in company building. As these AI-driven startups emerge, so too will an array of innovative and unconventional ideas that could become the next big thing.
Don't "Fake It Till You Make It"
Founders should ditch the "fake it till you make it" mindset and embrace a more honest approach, advises psychologist Dr. Gena Gorlin.
In her article, Gorlin explores the concept of "remembering what you know" as an alternative to faking confidence in high-stakes situations. By taking a step back and assessing your own unique skills, perspectives, and character traits, you can present yourself authentically in situations like pitching to investors or attending job interviews. Gorlin offers research-based guidance on how to apply this framework in emotionally charged moments and as a general practice, ultimately leading to wiser decision-making and increased self-assurance.
You Probably Shouldn't Work at a Startup
Are startups really the dream job they're made out to be?
Evan challenges the popular perception of working for a startup, addressing the financial and emotional realities that often go unmentioned. From the extreme business model risk to the financial sacrifices made for equity, he provides a detailed and cautionary insight into the world of startups, laying out the factors to consider before joining one. Discover the truth behind the hype, and learn from his personal experiences to better evaluate your startup opportunities.
Why Investors Love Vertical Labor Marketplaces
The future of work is shifting as vertical labor marketplaces rise, tailoring job placements to industry-specific needs. From healthcare to agriculture, these marketplaces offer unique features, creating growth opportunities and leveraging embedded finance.
Adam Keesling explores the reasons behind this trend, including the historically high rates of workers leaving jobs, the shift towards hybrid work models, and labor shortages in multiple industries. As vertical labor marketplaces continue to grow, they are set to become significant investments in the coming years, making them worthwhile considerations for job seekers, employers, and investors alike.
Succession Episode 4 Review
Hey there! As a fun addition to the Sunday Digest, Evan will be writing a mini-review for the final season of Succession. Each review will discuss the themes, writing, and dynamics of the show.
“You’re not a killer. You have to be a killer.”
If there is one quote that defines Succession, this gem from the Season 2 finale is it. Over and over again the kids fail to defeat or impress Logan because they have some personal weakness and refuse to go for the jugular.
Episode 4 was the first time that Kendall became a killer. In the final moments of the episode, he instructs Hugo to start a smear campaign against his dad (who hasn’t even been dead for 48 hours yet.) His justification: “It’s what he would’ve wanted.”
Kendall’s smirk after forcing Hugo to do the deed
Kendall has always flirted with the knife. At various points in the series he has lightly lacerated or half-heartedly backstabbed, but rarely has he tried to kill and meant it. He would be casually cruel to the help or bully Tom, but when it really counted he always missed his target. Even when he literally killed someone in season two, it was by accident.
In particular, it is in his relationship with Logan that Kendall struggles to backstab properly. In season one his vote of no confidence went nowhere. His season two and season three betrayals had little evidence and failed miserably. Only in his father’s death can Kendall finally blossom into the violence that is his birthright. Earlier this season, Logan describes himself as “a hundred feet tall. These people [everyone else] are pygmies.” The elimination of Logan’s looming shadow has left the airspace available for Kendall to finally grow.
A little side bar on the killer instinct: for the past few months, I’ve been working my way through various biographies and histories of media and tech executives. (Most recently, I publicly wrote about Steve Jobs). CBS, HBO, NBC, GE, Sequoia, on and on. I’m still not at the point where I feel that I have a defendable, publishable thesis, but I have noticed that one common quality held by the founders of these organizations is a knack for selective ruthlessness. Sure, they have moments of kindness, but there are many, many more instances of bloodthirsty cruelty. They’ll crush anyone that gets in their way—and without hesitation. Logan has this knack and now, apparently, so does Kendall.
While it works well as a power play, I’m not convinced that this is a good thing—these founders often hurt those who are closest to them. And Succession is a show where we see the damage done by the “killers.” But now, for the first time, it may be that Waystar Royco is ok? If Kendall fully matures into his father’s son and escapes his past demons, we may see him somehow pilot the company to safety. In the meantime, while Kendall cuts a new path, the people around him will be left hurting. Shiv is pregnant and on the verge of a divorce. Roman is in denial. The old guard at the firm are jostling for position and power. GoJo is looking to swoop up the Waystar Royco assets.
The test for the rest of the season will be who can become a true killer—and who is just human.
Early-bird pricing expires in 24 hours for our chatbot course!
Learn to build your own personal knowledge assistant in 30 days with Dan Shipper. Get access to the course for $1,500—a 25% savings. This price expires tomorrow, and almost 60 students are already signed up. Grab your slot while we still have openings!
That's all for this week!
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