Extended Conversation: Gary and Tony Sheng - Life, Work, and Future Directions

Summary

A wide-ranging conversation between brothers Gary and Tony Sheng covering Gary's departure from Alpha School, emerging opportunities in ministry and Web3, Tony's struggles with his crypto startup, and both brothers' philosophical reflections on work, purpose, and finding the right path forward. The discussion reveals both brothers at inflection points in their careers, seeking meaningful next steps while processing lessons from recent setbacks.

Key Topics

Gary's Current Situation

Emerging Opportunities

Gary describes multiple opportunities materializing through what he sees as divine providence:

Web3 Marketing Connection:

• "This one lady, she does a lot of Web 3.0 marketing, and people that represent nation states are hitting her up"
• Norway mentioned as one potential nation-state client
• The woman was praying when Gary's name came to her mind, despite minimal prior connection
• "The extent that she knew of me was a friend tried to introduce us in May, but then we connected in September when she was praying, and then my name came up"

Church Ministry Work:

• Helping a church in a small town outside Houston for free
• Tony's response: "That gives you heaven credits... You're doing yield farming"
• Gary: "Faith coin"

Philosophy on Work and Opportunity

Gary has shifted to a more receptive, less anxious approach:

• "Things kind of just keep emerging if I just take seriously what comes to me"
• "What I consciously have shifted away from is needing to feel hyped up about something"
• "The Bible says, Let tomorrow's worries be tomorrow's. I'm just literally... Things will emerge"

Alpha School Post-Mortem

Gary provides devastating insights into Alpha School's dysfunction:

Financial Reality:

• "They spent a half a million dollars per kid. Of these early kids"
• "He's burned half a billion dollars getting these initial outcomes"
• Student retention: "50% chance they drop off" from freshman to sophomore year
• Annual cost: "About 60k a year"

Organizational Dysfunction:

• "Internally the greatest shit show"
• "When you have a soulless, rabid capitalist billionaire that's ultimately affecting people's kids' lives"
• "They have no one close to a CTO type person there. No one close"
• Joe Lonsdale is "unable and unwilling to delegate"

Toxic Culture Example: Gary shares story of Andy Price (high-level Trilogy executive):

• Joe called Andy during a baseball game he'd been looking forward to for months
• Threatened his job over Alpha School issues: "Who am I going to fire, Andy? Is it going to be you?"
• Andy left the game in front of others, "staring blankly"
• Gary: "It's like a brutal corporate caricature"

Impact on Families:

• Nate Jones (former A16Z venture partner) revealed his daughter "almost killed herself" after attending Alpha School
• School expelled her despite good grades after parent asked too many questions

Gary's Assessment:

• "What he's done is he's memed some ideas that other people will do way better than him"
• "I can totally see myself getting involved with a way better run version of it"
• On Joe's hiring: "You hire 100 mediocre people. Hiring another 100 mediocre people doesn't fix the problem"

Tony's Professional Challenges

Cozy Protocol Hack

Tony's company suffered a security breach in October 2025:

• "Our project got hacked. For a small amount. It was like 400k"
• Technical details: "Integration issue... router contract was implemented incorrectly on the front end"
• "Luckily, it was our investors money. And then we just gave them the money back"

Business Struggles

• Product-market fit issues: "People just don't really care that much about the safety side of things"
• Team morale: "Payam is feeling burnt out. I've felt like mildly burnt out since starting the company"
• Financial position: Raised $18 million, approximately $9 million remaining
• Considering exit: Potential acquihire (possibly Coinbase), complicated by divorce proceedings

Divorce Complications

• Ex-wife owns significant portion of company shares (community property)
• Negotiated payout waterfall with cap for ex-wife
• Tony: "If we're getting acquihired for a little bit, then I feel like maybe this setup doesn't work that well for me"

Personal Development and Interests

Tony's Current Activities

Learning Japanese:

• Using it to prove "my brain still works"
• "The biggest feeling I have coming out from Japan is... I will never be a part of this"
• Partner/wife is fluent in Japanese but can't read or write

Gaming Depression Phase:

• Played TeamFight Tactics (TFT) intensively with friend Tim
• "Tim's music career is stalling out... We're just grinding to grandmaster at TFT"
• "It was kind of awesome. But it was also kind of sad"

Peptides Research: Tony has gone deep on peptide therapeutics:

• "When I saw crypto, I was like, oh, this is going to infinity. When I saw peptides, I was like, this is going to infinity"
• "Obesity is gone. It's over"
• Friends using Selank for anxiety: "Their anxious thoughts are just gone"
• Most close friends now on various peptides
• Sees massive market opportunity but regulatory challenges

Business Ideas and Philosophy

Education Disruption Concept

Extended discussion about disrupting Kumon:

Tony's Vision:

• "Why don't you just disrupt Kumon?"
• Not competing with schools but supplementing: "School sucks, they're not going to teach your kids"
• "You just plug a student in to their terminal and they just automatically learn"
• Economics: Could charge $10-50/hour, minimal supervision needed
• Kumon makes $600-700 million annually

Gary's Addition:

• China already has successful AI tutor systems
• Alpha School is essentially "a fork of Acton Schools" plus apps
• The apps are "a wrapper of free tools"

Investment Philosophy

Tony questions active business building:

• "Almost nothing makes sense to allocate your money into other than just like assets... equities and crypto"
• "If the best answer for me is to just be passive, like it's kind of sad"
• Mentions Joe Lamont's strategy: "Buying software companies and then just firing everyone and replacing them with a few Indians"

Philosophical Reflections

On Finding Purpose

Gary:

• Shifted from needing to feel "hyped up" about projects
• "When I'm in this hyped up, almost anxious... Need to be doing something... I end up working with the wrong people"
• Referenced Steve Jobs: "Everything is built by humans"
• "The only boss you should have is God. Who's going to give you insight into the biggest possible thing you're supposed to be doing"

Tony:

• "I have felt a bit of a lack of pull from something. Nothing's felt that important"
• "The thing that I like doing the most is picking up something new. And then getting really good at it"
• "There's no reason not to think as big as possible. Solve the biggest possible problem"
• References Kushner solving Middle East: "He's just a dude"

On Past Patterns

Gary on his tendencies:

• "It's usually I take on... Stuff that's not even that relevant. Because I'm insecure about not doing something all the time"
• Gave up coffee and "all other drugs" including microdosing mushrooms
• Mushroom dealer congratulated him: "He knows that it's not like... You don't want people to be dependent on that"

Notable Quotes

On Alpha School:

• Gary: "It's a precarious. I think when you have a soulless, rabid capitalist billionaire that's ultimately affecting people's kids' lives, it's different from selling monster energy"

On Work Philosophy:

• Gary: "You don't need to feel super fulfilled in every aspect of your life... There's different kinds of fulfillment"
• Tony: "You have a fixed amount of energy and bandwidth to put towards something. You might as well put it towards something that has the potential to really scale"

On Current State:

• Tony: "I need an angle. That's how I've been feeling for a while. What's the angle?"
• Gary: "The insight I just know will come. It's because there's... There's always something"

Action Items and Offers

1. Tony offered Gary potential role: "We could probably use you for... Like a growth engineer, marketer type person"
2. Gary to explore: Connection between Web3 marketing lady and pump.fun founder for promoting technical projects
3. Tony to send: More information about his company for potential collaboration

Key Takeaways

1. Both brothers at crossroads: Gary post-Alpha School, Tony with struggling startup
2. Shift in approach: Gary moving from anxious hustle to patient receptivity
3. Shared skepticism: Both questioning traditional startup/business models
4. Search for meaning: Both seeking work that provides both impact and fulfillment
5. Family support: Despite individual challenges, brothers maintain close relationship and explore collaboration

Context and Implications

The conversation reveals two highly capable individuals reassessing their approaches to work and life after experiencing the limitations of traditional Silicon Valley-style ventures. Gary's spiritual awakening and Tony's practical struggles with his startup represent different but parallel journeys toward finding more meaningful and sustainable ways to create value. Their discussion of education disruption and the peptides revolution shows they remain engaged with transformative opportunities while being more selective about where to invest their energy.