JHong and I have been collaborating deeply this month. Two separate posts, this podcast, and a live in the future.
Here’s a few nuggets I’ve learned from this episode:
Jen is incredibly kind and present, intelligent on many fronts - AI, marketing, the evolution and state of business in America, why communities should own the platforms they love - she knows her stuff, and,…, overall is someone who you would be blessed to have in your network.
If you are a subscriber of The Updraft I HIGHLY recommend checking out JHong .
AI changes many things and in some ways changes nothing, it shouldn’t be called AI, and how we engage with AI should be similar to how we vote, chose products, and enter legal agreements… AI is occurring and developing with or without us. Through our involvement, we can help shape its future to be something that serves us.
Curation of a personal brand happens in the same way. Our choice becomes how we harness and nurture that brand over time.
If my nugget left you with questions, yep. Me too. Folks like Jen are here to cut through the noise and put to bed harmful folklore and mythos that muddy the current AI landscape.
Natural Intelligence X The Updraft
Curious about how AI changes the concentration of work in our day to day?
About the degrees we were told to get and AI’s impact on the future job economy?
Pondering the BoF x McKinsey State of Fashion 2026 report and what it means for you?
What are my favorite birds?
How do I use AI when I own an emotional intelligence company?
Why I take screenshots of AI written notes that use the word ‘Clarity.’
About The Episode
Is AI actually intelligent, or just a very good mirror of us? Jennifer Hong, fractional CMO and writer behind the Substack Natural Intelligence, joins Dan Korus for a conversation that moves fast: why image generators keep failing to render real human faces (she calls it “the centroid problem”), why she switched from OpenAI to Anthropic and compares the two to Tesla and Volvo, and why she picked a public fight with Substack’s leadership over its handling of death threats and deepfakes on the platform.
They also get into:
Why “AI fluent” describes less than 1% of users, and what that number actually means
The 95/10 to 15 self-awareness gap and what it means for leaders specifically
The difference between a jerk and an asshole at work, and why only one is a dealbreaker
How two life crises rebuilt Jennifer’s relationship with control, trust, and delegation
Why personal branding is a prenup you’re already signing whether you write it down or not
The plan to buy back Letterboxd for its community instead of selling to private equity
A conversation about self-awareness, trust, and what’s left for humans once machines get good at mimicking the average.
Timestamps
0:00 Intro
0:38 Does “intelligence is no longer ours alone” still hold a year later
2:53 If not intelligence, what would you call it: the “centroid” problem
9:47 Why she switched from OpenAI to Anthropic: Tesla vs. Volvo
13:57 Growing up in Los Altos, getting kicked out of Berkeley
20:37 The rules she breaks: buying back Letterboxd from private equity
25:12 Substack’s Nazi problem, the open letter, and getting threatened for it
29:38 “Low-key Buddhism” and letting go of control
35:05 Trust and delegation as a leader
36:09 The health crisis that became her line of demarcation
48:31 Personal branding is a prenup you’re already signing
58:12 The 95/10-15 self-awareness gap and EQ diagnostics
1:03:39 Lightning round: good leadership, first-day advice, advice for execs
1:15:09 Where to find Jennifer Hong
Follow Jennifer Hong
Substack (Natural Intelligence): hongjennifer.substack.com
JHong’s LinkedIn: https://www.linkedin.com/in/jennifer-hong-100/
More from Kestryl Edge
Website: www.kestryledge.com
The Updraft (Substack): dankorus.substack.com
Hashtags
#EmotionalIntelligence #Leadership #ArtificialIntelligence #SelfAwareness #Substack #PsychologicalSafety #PersonalBranding #AIEthics #Podcast #KestrylEdge
