Playbook: Alex for Entrepreneurs and Founders

Your reference for using Alex across the startup lifecycle. Ready-to-run prompts for strategy, fundraising, hiring, and building.

What This Guide Is Not

This is not a habit formation guide (see Self-Study Guide for that). This is a founder’s toolkit — the specific ways Alex can accelerate your company-building, and the prompts that work.

Where to Practice These Prompts

Every prompt in this guide works with any AI assistant — ChatGPT, Claude, GitHub Copilot, Gemini, or whatever tool you prefer. The prompts are the skill; the tool is just where you type them. Pick the one you’re comfortable with and start today.

For an integrated experience, the Alex VS Code extension (free) was purpose-built for this workshop. It understands startup and founder context, lets you save effective prompts with /saveinsight, and brings your playbook and practice exercises into one workspace. VS Code is a free editor that takes minutes to set up, even if you’ve never used it before.

You don’t need a specific tool to benefit. You need the habit of reaching for AI when the work is genuinely hard — not just when it’s repetitive.

Core Principle for Founders

Building a company means making high-stakes decisions with incomplete information, at speed, across every function simultaneously. Alex’s highest value is in giving you a rigorous thinking partner when you’re the only person in the room — someone who pushes back, steelmans the opposition, and helps you see what you’re missing.

The key pattern: bring real context. Your actual numbers, your actual problem, your actual market. Vague inputs produce vague outputs. Treat Alex like a smart advisor who needs to understand your situation.

The Seven Use Cases

1. Strategy and Decision-Making

When to use: Big forks in the road. Market entry, pivots, build vs. buy, go-to-market.

Prompt pattern:

Help me think through this strategic decision:

Decision: [what I'm deciding]
Options: [the alternatives I'm considering]
What I know: [facts, data, constraints]
What I don't know: [key uncertainties]
Stakes: [what happens if I get this wrong]

Help me:
1. Identify what assumptions underlie each option
2. Find the crux — what is this decision actually about?
3. Steelman the option I'm currently against
4. Identify what information would change my mind
5. Give me your honest recommendation with reasoning

Follow-up prompts:

I'm leaning toward [X]. What am I missing?

If I'm wrong about this, what does the failure look like?

What would a smart skeptic say about this plan?

Try this now: You are deciding whether to pivot from B2C (consumer app, 2,000 MAU, $3 ARPU) to B2B (3 enterprise pilots at $2K/month each). You have 8 months of runway and a team of 4. Paste those numbers into the strategy prompt and ask for the strongest case for each path. The output will not make the decision for you — but it will force you to confront the unit economics you have been avoiding.

2. Fundraising and Investor Communication

When to use: Pitch decks, investor updates, term sheet navigation, fundraising strategy.

Prompt pattern:

Help me with fundraising:

Stage: [pre-seed / seed / Series A / etc.]
Traction: [key metrics and milestones]
Ask: [amount and use of funds]
Target investors: [who you're pitching]
Current deck: [describe or paste key sections]

Help me:
1. Sharpen the narrative arc of the pitch
2. Identify the 3 things investors most need to believe
3. Anticipate the hardest questions
4. Prepare answers to standard objections
5. Make the "why now" and "why us" more compelling

Follow-up prompts:

An investor says "your market is too small." How do I respond?

Write the one-paragraph company description for the deck.

What's missing from this pitch that Series A investors will ask for?

3. Customer and Market Understanding

When to use: ICP definition, customer discovery, competitive positioning.

Prompt pattern:

Help me understand my market:

Product: [what you're building]
Current customers: [who's buying, any patterns]
Problem you're solving: [how you describe it]
What you've learned: [customer interviews, feedback]
Competitors: [who else is in this space]

Help me:
1. Define the ideal customer profile (ICP) precisely
2. Identify the job-to-be-done that drives the purchase
3. Map the competitive landscape honestly
4. Find the positioning that's true AND differentiated
5. Identify which customers to say no to

Follow-up prompts:

Customers say they love it but don't buy. What's happening?

We have two very different customer types. Which do we focus on?

Help me write the positioning statement.

4. Hiring and Team Building

When to use: Defining roles, evaluating candidates, building culture.

Prompt pattern:

Help me with hiring:

Role: [what you need]
Stage: [company size, funding]
What success looks like: [specific outcomes in 90 days]
What you can/can't offer: [comp, equity, mission, growth]
Mistakes to avoid: [what's hurt you before]

Help me:
1. Define the role by outcomes, not job description
2. Identify the 3 things that predict success in this role
3. Create interview questions that reveal those things
4. Evaluate the tradeoff: speed vs. fit vs. cost
5. Assess whether to hire now or wait

Follow-up prompts:

I'm choosing between a great culture fit and a stronger operator. How do I decide?

Write the job description that attracts the right people.

A key person wants to leave. How do I think about this?

5. Product and Roadmap

When to use: Prioritization, MVP scoping, product direction, saying no.

Prompt pattern:

Help me think through product direction:

Current state: [what you've built]
What customers want: [request list, feedback]
Resources: [team size, timeline]
Business goal: [what you need this product to accomplish]

Help me:
1. Find the MVP cut that maximizes learning
2. Distinguish user wants from user needs
3. Prioritize by learning value, not feature count
4. Identify what not to build
5. Define what success looks like for the next 90 days

Follow-up prompts:

I have 10 feature requests and capacity for 2. How do I choose?

Customers keep asking for [X]. Should we build it?

We're shipping too slowly. Where should I look for the bottleneck?

6. Operations and Scale

When to use: Processes breaking down, team growing, things falling through the cracks.

Prompt pattern:

Help me fix this operational problem:

What's breaking: [describe the issue]
Current process: [how you do it now]
Team size: [how many people involved]
Stakes: [what happens if this isn't fixed]

Help me:
1. Find the root cause (people, process, or tools?)
2. Design a lightweight fix that won't create bureaucracy
3. Identify what to systemize vs. what to keep manual
4. Define clear ownership
5. Create a way to know if the fix worked

Follow-up prompts:

I don't have time to fix this properly. What's the 80% solution?

A process that worked at 10 people is breaking at 30. How do I redesign it?

Create a simple runbook for [repeating process].

7. Resilience and Clear Thinking

When to use: When you’re stuck, spiraling, or need to think through a hard situation.

Prompt pattern:

Help me think clearly about this:

Situation: [what's happening]
What I'm feeling: [honest assessment]
What I'm afraid of: [the real fear]
What I've tried: [what hasn't worked]

I need help:
1. Separating what's real from what I'm catastrophizing
2. Identifying what I actually control
3. Seeing the options I'm not considering because I'm stressed
4. Finding the next small concrete action
5. Getting honest feedback on whether my plan makes sense

Follow-up prompts:

Is this a real problem or am I overreacting?

What would I tell a founder friend in this exact situation?

What does getting through this look like?

Your AI toolkit: These prompts work in ChatGPT, Claude, Copilot, Gemini — and in the Alex VS Code extension, which was designed around them. Start with whatever you have. The skill transfers across all of them.

What Great Looks Like

After consistent use, you should notice:

• Sharper thinking before high-stakes decisions
• Better-prepared investor conversations
• Clearer customer and market understanding
• Faster hiring with fewer mistakes

The goal isn’t for Alex to run your company — it’s for Alex to be the thinking partner that helps you run it better.

Practice Plan

Month 2–3

Shift from guided exercises to independent workflows — build templates, integrate AI into your real projects, and create reusable prompt libraries for repeating tasks.

Track Your Growth

/saveinsight Strategic Decision Frameworks: decision framing that clarified [specific fork in the road]

/saveinsight Pitch Refinement Patterns: narrative structure that resonated with [investor type]

Continue your practice: Self-Study Guide has weekly challenges to keep building your skills after the workshop ends.