Claude Pro for Plug and Play IndianaA working reference, built by Tucker Carlile
Built for Brandon Noll
You bought Claude Pro. Here's the playbook to actually get 10 hours a week back.
This isn't a feature tour. It's the small handful of habits, prompts, and connectors that turn $20/month into your most-used staff member, built around how you actually run Plug and Play Indiana.
Last updated 2026-06-01 · Companion to our Tuesday session · Tucker Carlile, Carlile Advisors
Learn these four habits and you'll outperform 95% of Claude users, including most VCs.
1. Make Claude interview you before it answers
The single highest-leverage habit. Before Claude writes the partner email, the IC memo, or the market map, tell it to ask you 3 to 5 questions first. You'll get an output 3x better with half the back-and-forth, because now the model knows what "good" actually means to you.
Before you respond, ask me 3-5 specific clarifying questions about:
- Who the audience is and what they care about
- The tone and length I want
- What MUST be included and what to avoid
- What "good" looks like for this specific output
Wait for my answers before producing anything. Skip this only
for clearly mechanical tasks (reformatting a list, summarizing
a single doc).
Save this snippet. Append it to any non-trivial prompt. It works on every model.
2. Save your prompts. They become skills.
A "skill" is just a prompt you keep using. Most people start a fresh chat every time and re-explain themselves. Instead: when a prompt works, save it. Drop it in a Claude Project as the system prompt. Now it's a reusable tool: the deal triage skill, the partner briefing skill, the Monday standup skill.
Inside Claude, Projects are how you do this. The system prompt = your skill's "operating instructions." The uploaded files = its knowledge. Build 5 to 10 of these over 2026 and you have an AI staff.
3. Have Claude write your prompts
Prompt engineering is itself a Claude task. This is the meta-move that compounds.
I want to build a Claude prompt for the following job:
[describe the goal in plain English, messy is fine]
Write me a system prompt that would make Claude great at this.
Include:
- Role and persona
- Inputs Claude should expect
- The format of the output
- Things to flag instead of guessing
- A "verify before relying on this" reminder
Then ask me what's missing before I paste it into a Project.
Paste the result back into a new Project. You just built a custom skill in under 90 seconds.
4. Connectors turn Claude from chatbot into operating layer
The version of Claude you've used so far is the chat box. Once you turn on connectors (Gmail, Calendar, Drive, eventually Salesforce/HubSpot/Slack), Claude can read your inbox, prep meetings from your calendar, and pull from your actual cohort files. That's where "AI tool" becomes "operating system upgrade." See the connectors checklist below.
The pattern
Interview-first → save the winners as skills → let AI write the next version → wire it to your real data. That loop is the entire job.
02Prompts & Projects
6 prompts to paste tonight
Curated from a longer list. These are the ones that pay off fastest for an accelerator director. Click any card to expand the full prompt, then copy or send it straight to Claude.
0160 to 80% faster first-pass memo
PnP Indiana Deal Triage
Use as a Claude Project system prompt. Drop any deck into the chat and you get a structured pass back.
You are an analyst supporting Brandon Noll, Director of Plug and
Play Indiana. PnP Indiana runs two accelerators:
- Warsaw Medtech (sponsors: Zimmer Biomet, Paragon Medical,
OrthoPediatrics, Parkview Health)
- Indianapolis Lifetech (sponsors: IU Health, IU, BioCrossroads, CICP)
For every deck or company I drop, return:
- 1-line company summary
- Team: founders + most relevant prior experience
- Traction: numbers only. Flag anything hand-wavy.
- Ask + use of funds
- Top 3 risks
- Fit to PnP Indiana (score 1-10) + which corporate partner would
care most and why
- 3 specific diligence questions for the founder
- "Human review required" checklist before relying on this
Cite sources where you can. If a claim is uncertain, mark it
uncertain instead of guessing.
Expand prompt▾
02save 3 to 5 hrs/week on cohort ops
Batch Co-Pilot
One Project per cohort. Upload founder one-pagers, partner notes, monthly updates. Ask it anything about the cohort.
You are Brandon's cohort operating co-pilot for [Warsaw Medtech
Batch 5 / Lifetech Batch 1].
You know:
- Every company in this batch (load their one-pagers)
- Each company's milestone, biggest blocker, best partner fit
- The corporate partners and what they care about
- Upcoming expo, demo day, and partner-meeting dates
When I ask anything, your output should be:
- Brief enough for a busy regional director
- Partner-safe (do not disclose sensitive founder details unless
I explicitly ask)
- Action-oriented (owner, next step, deadline)
Discovery-first rule: for any non-trivial request (drafting a
partner update, prepping a founder intro, writing a follow-up),
ask me 3-5 clarifying questions first. Then wait for my answers.
Expand prompt▾
0315 min prep instead of 90
Corporate Partner Briefing
Before any Zimmer / IU Health / Paragon meeting, run this against the Project that has your cohort context.
Create a 1-page briefing for my upcoming meeting with [partner].
Include:
- Why they should care about this cohort right now
- 3 startups in our current batches most relevant to them, with
a 1-sentence "why this matters to YOU" for each
- Suggested intro angles
- Risks / sensitivities to avoid
- 5 smart questions I should ask
- A draft follow-up email I can edit
Keep it under one page. Cite the cohort docs you used.
Expand prompt▾
042-day analyst task → 20 min
Lifetech Market Map
Run for any vertical: AI medical imaging, surgical robotics, RNA delivery, digital health, etc.
Build a market map for [sub-vertical].
Include:
- 3 incumbents (public or late-stage)
- 5 venture-backed challengers (with last round + lead investor)
- 3 emerging / stealth-ish companies if you can defensibly name them
- A 1-sentence moat for each
- Who buys this and what the regulatory path looks like
- Where [PnP Indiana portfolio company name, if relevant] fits
Cite sources for every claim. Flag weak evidence explicitly. If
you can't defensibly name a stealth company, say so instead of
making one up.
Expand prompt▾
05passive listening → reusable content
Podcast / Video Synthesis
Drop a transcript from a medtech, FDA, VC, or founder podcast. Get 10 takeaways and 2 LinkedIn drafts in your voice.
Analyze this podcast transcript for Brandon Noll at Plug and Play
Indiana. Extract:
- 10 key insights
- 5 implications for medtech / lifetech founders
- 3 implications for corporate partners (Zimmer, IU Health, etc.)
- 3 questions Brandon could ask a founder based on this
- 2 LinkedIn post drafts in Brandon's practical, Indiana-first
voice (not buzzwordy)
- Any claims that need verification before reuse
Output as markdown. Don't bury the headline, lead with the
single most useful takeaway.
Expand prompt▾
06no more notebook tax after meetings
Voice Note → Relationship Notes
After a founder meeting or partner dinner, dictate a 60-second voice note. Drop the transcript. Get structured CRM-ready output.
Turn this voice note into structured relationship notes.
Extract:
- People (name, role, company)
- Email / LinkedIn if mentioned
- Opportunity or context
- Promises I made
- Follow-up owner + deadline
- Suggested next message (3 lines, in my voice)
- What should be logged to CRM vs. kept as personal note
If anything is uncertain, mark it uncertain. Don't invent
details I didn't say.
Expand prompt▾
03Plumbing
Connectors to wire up this week
All of these are native to Claude Pro. None require Tucker. About 15 minutes of setup, biggest leverage you'll get from your $20.
1
Do these now
Free · 5 min each
Gmail. Search and draft emails, summarize threads, prep partner replies.
Google Calendar. "What's on my plate Tuesday?" "Prep me for the 2 PM with IU Health."
Google Drive. Point Claude at your cohort folder. Now Batch Co-Pilot can read every one-pager.
2
When you're ready
1 to 2 weeks
Slack. The wedge demo. Imagine a private #pnp-claude channel where you ask questions and Claude answers using everything connected. This is the real "operating system" moment.
Notion or Confluence. If you keep batch notes there, plug it in.
3
The advanced playbook
Once you're fluent
HubSpot / Salesforce. When ready, Claude can read your CRM and answer questions like "who haven't we followed up with since the Indy 500 dinner?"
Monday.com. Partner update generation from current cohort milestones.
Scheduled morning brief. 7 AM ET every weekday: Indiana medtech/lifetech news, fundraises, partner mentions, FDA changes. Lands in Slack or email.
Why this order matters
Most people try to architect everything at once and stall. Turn on the three free Gmail/Calendar/Drive connectors first. Use Claude with real data for a week. Then you'll know exactly which Phase 2/3 connector matters most.
04Sequence
A 30-day roadmap
What to do Monday, what to do week 2, and the advanced moves to graduate into.
Week 1 · you, solo
Create the PnP Indiana Deal Triage Project. Paste system prompt #1 above.
Create the Batch Co-Pilot Project for your current Lifetech or Warsaw cohort. Upload one-pagers.
Turn on Gmail, Calendar, Drive connectors.
Use Project #1 on three real decks. Use Project #2 to draft Monday's standup.
Week 2 · getting comfortable
Try the "make Claude interview you" pattern on every non-trivial prompt for a week. You'll feel the lift by Friday.
Save the prompts that worked. Drop them into new Projects.
Have Claude write a custom prompt for one workflow it can't do well yet (use the meta-skill #3 template).
Month 1+ · the advanced playbook
A scheduled morning brief that lands at 7 AM with Indiana medtech/lifetech news, partner mentions, and FDA changes.
HubSpot or Salesforce connector wired up so Claude can read your CRM.
A "founder coach" skill: paste a pitch transcript, get critique in three corporate-partner voices (Zimmer / IU Health / investor).
A cohort-wide Slack agent so the whole team can query the same brain you've been building.
The frame for ROI
Claude Pro is $20/month. If the Deal Triage and Batch Co-Pilot Projects save you even 5 hours/month at a regional-director hourly rate, that's a ~100x return. Realistic target is 15 to 25 hours/month within 60 days.
05Field notes
What YC, All-In, and operators are saying right now
Curated from a 2026 YTD pass on Y Combinator's channel and a recent All-In Podcast deep-dive on Anthropic vs OpenAI. These are the patterns that actually matter for accelerator directors, not the hype.
The big pattern across 30+ YC videos in 2026
YC's 2026 uploads are overwhelmingly about AI-native company design, not just AI products. The repeated message: make company knowledge legible, centralize operating data, give agents controlled access to tools, and let workflows improve recursively while humans focus on judgment, taste, and relationships.
Translation for PnP Indiana: HubSpot/Salesforce shouldn't just be a contact database. It should become the relationship graph, startup memory, intro history, and corporate-partner intelligence layer that Claude queries. The accelerators that win will be the ones whose ops are agent-ready.
5 episodes worth your time
YC · Lightcone · 2026-05-27
Inside YC's AI Playbook
Pete Koomen walks through how YC built internal agent infrastructure with one central database, a shared tool registry, reusable skills, and recorded organizational context. The takeaway: treat AI as the company's operating system, not an add-on.
How to Build a Self-Improving Company with AI, by Tom Blomfield
Argues founders should build recursive AI loops across product, support, and ops so the company gets smarter while the team stays small. Same logic works for a regional accelerator: every founder meeting and partner intro can feed a scoring loop that improves the next match.
Tokenmaxxing: How Top Builders Do the Work of 400 Engineers
Solo operators using AI orchestration (prompts, skills, agents, memory) now compete with large engineering teams. For PnP: you don't need to hire an analyst, you need a Project that acts like one.
Products will soon need both a human UX and an agent UX. Documentation, APIs, permissions, and structured outputs become distribution surfaces. Useful for diligencing AI startups: ask whether their data and APIs are agent-readable.
Anthropic's Generational Run, OpenAI Panics, AI Moats, Meta Loses Lawsuits
Sacks calls Anthropic's recent quarter a "generational run": Claude Code plugins, Co-work (Claude executing cron jobs across Gmail and Notion for business users), and Opus 4.6 dropping back-to-back. Jensen Huang and Michael Dell both publicly flagged Opus 4.6 as "the first true agentic model" and an industry inflection point. Anthropic's bet (API + enterprise coding tools, not consumer chat) is converting; OpenAI is pivoting hard in response.
Translation for PnP Indiana: the "Claude as cron job across your inbox + docs" pattern is exactly the Brandon-shaped workflow. Monday standups, deal-flow triage, partner updates, all running on a schedule against the data already in your Workspace. Same episode also touches AI moats collapsing under agents and SaaS valuations getting reshuffled, context worth carrying into founder conversations.
"Plug and Play brain" thesis. Treat HubSpot as the venture operating system. Add agent-friendly fields: sector thesis, AI technique, proprietary data source, partner fit, intro status, diligence risk, next best action. Then point Claude at it.
AI-readiness as a diligence axis. For every AI startup that comes through, score them on: data advantage, workflow embedding, model dependency, reasoning/evaluation harness, cost curve, buyer urgency. That's a defensible diligence framework heading into 2027.
Corporate-partner pain maps. Convert every partner meeting into structured pain points + buying triggers in Claude. Match startups to partner pain, not just industry tags. Better referrals, better follow-throughs.
Full YC 2026 YTD briefing (30+ video summaries with per-episode "what this means for PnP" notes) lives in Tucker's workspace at data/yc_2026_brandon_noel_briefing.md. Happy to email the full version on request.