The Power of Ask Prompt Library

I want you to act as a sharp, experienced business strategist helping me find the hidden assets already sitting inside my business — the ones I've stopped noticing because they feel normal to me.

Here is context about my business. Answer as completely and honestly as you can, even in rough bullet points:
1. What does my business sell today, and to whom?
2. Roughly what is my annual revenue and how many people work here?
3. Who are my best customers — not just my biggest, but the ones who get the most value, refer others, or stick around the longest? What makes them different from an average customer?
4. What problems do I solve for customers over and over again, almost on autopilot?
5. What do customers constantly ask me for — especially things that are slightly outside what I officially sell?
6. What am I (or my team) unusually good at, in a way that would be hard for someone else to copy quickly?
7. What information or data have I accumulated over time just by running the business (customer behavior, complaints, patterns, requests, seasonality)?
8. What processes, workflows, or internal tools have I built to make my own operation run better?
9. What do I currently do for customers without charging separately for it — the "of course we'll just take care of that" things?

Once I've given you this information, I want you to identify 15-20 specific Hidden Assets in my business, sorted into these 11 categories: Customers, Relationships, Data, Expertise, Process, Technology, Trust, Distribution, IP, Unused Capacity, and Problems Solved For Free.

For each Hidden Asset, give me:
- A specific, concrete name for the asset (not a vague category label)
- Why it matters — why this is genuinely valuable, not just "nice to have"
- Who might value it — a specific type of buyer or partner, not "everyone"
- How it is currently monetized (often the honest answer is "it isn't")
- One possible future use that would turn it into new revenue

Finally, call out the top 3 most undervalued assets on the list — the ones I am most likely to be sitting on without realizing their potential. Be direct and specific. Avoid generic business advice — ground everything in the details I actually gave you.

I want you to act as a creative business strategist running a divergent brainstorm. Your job right now is quantity and range of genuinely distinct ideas, not judgment — we will evaluate them later.

Here is a Hidden Asset from my business (or a short list of them):
[Paste one or more Hidden Assets here — a name, why it matters, and who might value it. If you don't have this yet, describe an asset in your business: something valuable you already have but haven't fully monetized — a customer base, a dataset, a skill, a process, a piece of technology, a relationship network, or something you already do for customers for free.]

Using that asset (or assets) as raw material, generate as many distinct new business possibilities as you can, deliberately forcing yourself through each of these 19 different lenses so the ideas don't all sound the same:
Subscription, Software, Data, AI Agent, API, Marketplace, Certification, Licensing, White Label, Education, Membership, Premium Service, Low-Cost Product, New Buyer, New Industry, Partnership, Acquisition, Performance Pricing, and Inversion (flip who pays for what, or what's given away vs. sold).

Aim for at least 25-30 possibilities if you can, even if some feel like a stretch — a wide net is the point of this exercise. For each one, give me:
- A short, memorable name
- The customer it's for
- The specific problem it solves for that customer
- Which hidden asset it leverages
- The business model (how it would actually make money)
- A realistic potential price point
- Why now — why this is a reasonable bet to test today rather than five years ago or five years from now

Don't filter for "good ideas" yet — I specifically want range, including a few ideas that feel unconventional or slightly uncomfortable. Judgment comes in the next step. Present the results in a scannable list grouped by lens.

I want you to act as a disciplined, unsentimental investor evaluating a list of business opportunities. Creativity is done — this is the judgment step, and I want you to be honest even if it means telling me an idea I like isn't actually strong.

Here is my list of possibilities (paste as many as you have — ideally 10-50, each with a name, customer, problem, business model, and pricing):
[Paste your list of possibilities here.]

Score each one from 0-10 across these 12 categories, and briefly justify each score in a few words:
1. Customer Pain — how acute is the problem, really?
2. Willingness to Pay — would this customer actually pay for a solution?
3. Customer Access — how easily can I reach this customer today?
4. Existing Asset Leverage — how much does this rely on something I already have vs. something I'd have to build from zero?
5. Speed to Revenue — how fast could this generate its first dollar?
6. Cost to Test — how cheap is it to find out if this idea is real?
7. Gross Margin — how much of each dollar would actually be profit?
8. Recurring Revenue — does this generate repeat or ongoing revenue, or is it one-and-done?
9. Scalability — can this grow without growing my costs at the same rate?
10. Defensibility — how hard would this be for someone else to copy?
11. Founder Dependence — could this run and grow without me personally in the middle of every transaction?
12. Market Timing — is right now a good moment for this, based on trends, behavior, or technology?

Add up an overall score out of 100 for each idea. Then rank them and narrow the list down in two stages: first cut it to your top 10, then to your final 4.

For the final 4, sort each into one of these archetypes and explain why:
- Boring Winner — high confidence, modest ceiling, fast and cheap to prove
- Hidden Gem — underrated relative to the effort required, strong margins
- Scalable Winner — high ceiling with a credible, low-founder-dependence path to scale
- Moonshot — high risk, high reward, uncertain timing or access, but potentially trajectory-changing

Finally, tell me which single opportunity you would choose to test first over the next 30 days if you were in my position, and explain your reasoning in plain language.

I want you to act as a rigorous startup validation coach. My instinct is to start building — your job is to stop me from building anything until I've proven someone will actually pay. Don't build it yet. Ask first.

Here is the opportunity I've chosen to test (paste what you have — name, customer, problem, business model, pricing):
[Paste your chosen opportunity here.]

Help me turn this into a real, cheap, fast 30-day market test. Specifically, give me:

1. Customer Hypothesis — the specific, narrow type of person or company I believe will want this, stated precisely enough that I could identify 20 real examples of them today.
2. Problem Hypothesis — the exact problem I believe they have, stated in their words, not mine.
3. Simple Offer — the smallest, simplest version of this offer I could put in front of a real customer this week, stripped of every feature that isn't essential to test the core value.
4. Initial Pricing — a specific price to test, along with the reasoning behind that number.
5. 10 Customer-Discovery Questions — real questions I could ask 10-15 prospective customers this week that would tell me whether the problem and willingness to pay are real, without leading the witness.
6. Beta/Pilot Offer — a specific, low-risk way to get a handful of real customers to say yes in the next two weeks.
7. 30-Day Validation Plan — a week-by-week plan for what I do, who I talk to, and what I'm watching for.
8. Kill Criteria — the specific, honest signal that would tell me to stop and walk away from this idea rather than keep pushing.
9. Maximum Validation Budget — a realistic dollar and time cap I should not exceed before I have real evidence.

Finish with a section called "YOUR NEXT 3 ASKS" — the three specific, concrete actions I should take in the next 7 days to start getting real answers, ranked in the order I should do them. Make these asks unmistakably clear and specific — not "talk to customers" but the literal first message I should send and to whom.

I want you to act as a relationship strategist helping me identify and approach the specific people who could meaningfully change the trajectory of my business — the people I have been avoiding asking because it feels too big, too bold, or too uncomfortable.

Here's context on where I'm headed:
1. What is the single biggest thing I want to accomplish over the next 12 months?
2. What kind of help would make the single biggest difference to that goal — customers, capital, mentorship, a warm introduction, media coverage, a strategic partnership, an acquisition, or key talent?
3. Who have I been putting off reaching out to, even though part of me knows I should? List anyone who comes to mind, no matter how unlikely or intimidating.

Using that context, help me build a Dream 100 list, organized into these categories: Dream Customers, Strategic Partners, Investors, Mentors, Connectors, Media, Acquisition Targets, Talent, and Other. For each category, suggest 3-5 realistic types of people or specific names if I've given you any, and for the ones I've already named, help me build a real plan.

For each specific person, give me:
- Why They Matter — the specific reason this relationship could change my trajectory, not a generic reason
- What You Can Give — something genuinely valuable I could offer them, so this isn't a one-sided ask
- Smallest First Ask — the smallest, lowest-pressure first step that could realistically get a yes
- Potential Warm Path — any realistic way I could get introduced rather than going in cold
- What Not To Ask Yet — the ask that would be premature and could burn the relationship if I made it too soon
- Exact Outreach — a short, specific message I could actually send today, in my own voice, with no generic template language

Finally, as a bonus, pick the single most intimidating name on my list and write me "The Ridiculous Ask" — the version of the outreach I'd send if I knew, for certain, that they couldn't say no. Then help me find the real, respectful version of that same courage I could actually use today.