AI mental health screening · Grace Chang · Series A, post-PMF · San Francisco

• Cold emailed Grace twice — first email high signal, no reply. Followed up a week later with a better hook → got a reply and a meeting
• Built Kintsugi's business case from first principles before the call
  • Mapped the core inefficiency: manual, human-dependent screening
  • Quantified: insurers lose ~$1.26B/yr from missed depression in chronic-disease members
  • Fermi estimate: flag 1% of calls + convert 20% to care → ~$240M saved → ROI of 120×
• Mapped smart outreach, automated ops workflows (BD meeting summaries → Slack + HubSpot)
• Got an assignment from Albert (COO): build a CXO pitch deck — shipped with full autonomy, went beyond the brief
• Shipped a Loom walking through the work before the next call

• Got the offer (~$120k/yr) and declined
• Wanted apprenticeship access to a founder I admire, not a contract. Long-term games with long-term people. Walked away respectfully.

Remote patient monitoring · Naren Nachiappan, 4× founder · Pre-PMF · California + Bengaluru

• Identified the core constraint: clinician time
  • One physician capped at ~20 patients/day
  • 78Health's model unlocks 1,500+ patients per physician
• Built the revenue math: $6M run rate = 0.2 take rate × $250k/physician × 120 physicians
• Mapped the full funnel — physician signing to first live patient. Flagged missing denominators: active patients per physician, CAC, retention speed, activation rate
• Ran a pre-mortem on the fundraise and two-market risk (US + India bandwidth split)
• Asked the hard questions: EMR integration risk, platform risk from Epic/Cerner, why two markets simultaneously

• Got to offer discussion — equity, comp, onboarding — before fundraise timing created uncertainty

Mental health platform · Dr. K · Texas

• Built two distinct ICPs with job-to-be-done mapping
  • Guides ICP: 18–32, male-skewed, gamer identity, self-diagnosed ADHD/anxiety. Trigger: "I've watched 40 Dr. K videos, time to go deeper." Value prop: $120 vs $200/therapy session
  • Membership ICP: 18–35, long-term Dr. K follower. Wants ongoing growth, not a one-off fix. $10–15/mo frictionless
• Mapped both funnels end-to-end
  • Guides CVR at 0.5–1% of 1.5M monthly site visitors
  • Membership: 6–12K active subscribers, $72–144K MRR, 8–15% monthly churn
• Identified revenue bottlenecks and built the 6-month path to 50% growth: $1M → $1.5M

• Asked hard questions in the interview because I genuinely cared what moves the needle — got a generic rejection with zero context
• Flagged it directly to Dr. K: "For a company whose mission is built on trust, care, and honest conversation — these small interactions carry disproportionate weight." Said my part. Moved on.

Stealth healthcare startup · Ex-Palantir · NYC

• Read his blogs. Watched his podcast. Played Factorio. Then cold emailed with a personalised video — mission-aligned, not credential-matching
• Deep research: his writing, podcast appearances, publicly shared frameworks
• Ask was deliberate: start with a tiny problem, earn the rest

• Nabeel replied, watched the video, engaged genuinely
• Stalled on visa. Not merit.

WTFund / Zerodha · Bengaluru

• Went deep into NK's world — podcasts, investment thesis, WTFund cohort — before building anything
• Mapped why energy transition is his highest-conviction bet, bottom-up:
  • GHGs → renewable shift → CO2 halved
  • UEI as the energy trading layer
  • CPO incentive alignment as the real unlock
• Built a Figma mindmap validating the whole thesis. Researched his portfolio: Ossus, SolarSquare, Matel. Ranked 10 key insights. Did the full work.
• Then didn't send it.

• Caught myself mid-way: the drive was "get a 10x career jump" — ego, not mission. Chose not to reach out from that place.
• The self-awareness that stopped me is the thing he'd respect most.

Gumroad / Antiwork · NYC

• Studied the business cold: balance sheet, Antiwork's north star ($10M EBITDA), product philosophy, open-source strategy, PM stance
• Sahil posted a $1K story bounty — wrote the sci-fi story with AI, then declined the money. Cold email: "I don't want the $1,000. I want to work with you."
• Built a personalised video: why his "Reflecting" post was the moment I knew I had to reach out, how I could create leverage starting tomorrow

• Got ghosted — then noticed he'd blocked me on X and deleted my comment on his thread
• Reached back out: "Felt weird and unlike you — curious if something went wrong on my end." No reply.
• Chose not to force it. Moved on clean.

1. There is no finite wealth in this world. Wealth can be created — somebody doing well doesn't always come at someone else's expense.
2. Go where the demand is / obvious needs exist.
3. Go where capital is (capital is leverage).
4. Good decision making and high leverage >>> mere hard work. Decision making is a leverage touch point — use clear thinking (via Shane Parrish) to maximise odds of success: define clear goal, track least resistant path to get there; leverage LLMs to see your blindspots, cheaply validate hypotheses.
5. Entrepreneurship feels right (an obvious choice for me) — not like I am choosing this for a set period of time.
6. Luck exists. It's an arbitrary multiplier — all successful startups got lucky (luck was part of the equation, not the only variable).
7. I want to be in an environment with maximum leverage — gravitating towards high concentration of long-term players with abundance mindset.
8. Truths internalised: there are no set rules. There are no "adults" — everyone is figuring it out along the way. All humans are suffering in their own ways, because life (having desires) is suffering (via Buddhist philosophy).
9. What you work on + who you work with >>> how hard you work (via Naval).
10. Double down on asymmetric bets, tail events via Taleb (capped downside, asymmetric positive upside). Absolute probabilities of future events are useless — what you want to look at is tail events.
11. There are always going to be waves to surf — I just need to position myself at the right place and be ready with my surfing gear.

1. What exact problem I am excited to solve for fellow humans — unique insight, thesis, wedge (why this problem, why me, why now). Currently actively exploring Mental health, Healthcare, GenAI B2B SaaS. One area: no. of professionals as bottleneck in Mental health care in the USA (10 professionals / 100,000 patients). How can AI help augment professionals to scale more patients?
2. Right community and environment where I will flourish.
3. + Many more things I haven't figured out — if I already had, I wouldn't be writing this and would have already reached where I want to.

1. I have an entrepreneur's DNA.
2. I am doing this 100% for me — it aligns internally with what I want to spend my time on (value creation, problem solving, practising autonomy).
3. I want to solve problems where the product materially improves the user's life.
   
   
4. Embodied — Steve Jobs, circa 1994: "When you grow up, you tend to get told that the world is the way it is and your life is just to live your life inside the world... Life can be much broader once you discover one simple fact, and that is: everything around you that you call life was made up by people that were no smarter than you. And you can change it, you can influence it, you can build your own things that other people can use. Once you learn that, you'll never be the same again."

• Finding the right tribe — being around right people, right environment, playing long-term games. I know I can't do it alone; efforts can only multiply with people. Leverage of right community is needed.

Create value — Utility × Scale (inspiration from Elon Musk). "How useful have you been to your fellow human beings times how many people?"

Creating massive value for a very long period of time requires intentionality, space and depth. I am on that path.

I am very confident this is bound to happen. It's okay if people around can't see it right now — the right people will come along the way, and I shall keep moving forward.

Entrepreneurship simply is solving offering gaps in a market.

🧠 Nudges I use to Think Bigger

1. Use "What if it works?" as a forcing function.
2. What would it take for this to be the next default behavior? Musk thinks: "What must be true for this to be inevitable?"
3. Peter Thiel's "secrets" lens: What do you believe is true that most people don't? What will compound in value and defensibility over time?
4. Work from physics, not vibes — identify a constraint you can break (latency, cost per inference, regulatory bottleneck) and re-architect the stack around it.
5. Secrets + Aggregation Theory: look for markets where you can aggregate fragmented supply/demand with a superior UX and own the demand.

PMF

1. You can't motivate a user — solve for existing behaviours. High-frequency chores a persona hates and is prone to errors → automate via LLMs. Make something people want.
2. Solve for existing pains (world is full of inefficiencies — my job is to look at the right one and solve for it).
3. 0 → 1: 100 users who absolutely love your product >>> thousands who like it (via Sam Altman, YCombinator).