Go-To-Market Playbook

AskMyStack Launch Strategy

January 2026

Goal: 50 paying customers and $2,500 MRR within 60 days of launch

The Opportunity

“You pour your heart into writing posts... and then they just sit there, stagnant and dead in your archive.”

The Problem

3M+ Substack newsletters exist today
Average archive: 100+ posts, rarely revisited
New readers can't explore the back catalog
Writers lose connection to their best work

AskMyStack Solves This

Let your readers talk to your entire body of work. Every post becomes discoverable through conversation.

Why Us: Writers First, Founders Second

Luke Deasy

Infinite Zest on Substack

4+ years writing on Substack
600+ posts published
Built AskMyStack for his own readers first
Understands the writer's journey intimately

The Positioning Advantage

We're not outsiders selling AI tools to writers. We ARE writers who built this to solve our own problem.

“I've been writing on Substack for 4 years. I built AskMyStack because I was tired of watching my best posts disappear into the archive.”

Target Audience: The Prosumer Sweet Spot

100-1K

Subscriber Range

50+

Posts in Archive

$50/mo

Price Point

Why This Segment?

Committed enough to invest in their publication
Not yet big enough to have custom solutions
Hungry for tools that give them an edge
Most engaged with their reader community

Avoid (For Now)

<100 subs: Not ready to pay, still finding voice
>10K subs: Different needs, longer sales cycle
Tech writers: Will try to build it themselves

Three-Phase Launch Strategy

Phase 1: Week 1

Soft Launch on Reddit

Community validation in r/Substack. Authentic sharing, not selling. Gather feedback, build social proof.

Phase 2: Weeks 2-4

Cold Email Outreach

Targeted campaigns to Substack writers by category. Personal, writer-to-writer messaging. 50-100 emails/day.

Phase 3: Month 2+

Scale & Iterate

Double down on what works. Expand categories. Consider Substack Notes, partnerships, content marketing.

Goal: 50 paying customers in 60 days → $2,500+ MRR

Phase 1: Reddit Soft Launch

Target Subreddits

Subreddit	Members	Approach
r/Substack	~25K	Primary target
r/Blogging	~300K	Secondary
r/writing	~2.5M	Careful approach
r/creators	~15K	Newsletter focused

Posting Strategy

Lead with story: “After 4 years and 600 posts on Substack, I built something...”
Show don't sell: Share the problem, your solution, invite feedback
Be genuinely helpful: Answer questions about Substack, AI, writing
No spam: One quality post per subreddit, then engage in comments

Note: r/Substack prohibits self-promotion. Use their pinned threads or share as genuine community discussion.

Phase 2: Cold Email Category Strategy

Category Prioritization

Based on paid engagement rates (Newsletter Circle research)

Category	Paid %	Priority
Music	34%	🔥 High
Faith & Spirituality	27%	🔥 High
Sports	22%	🔥 High
Literature	20%	Medium
Culture	18%	Medium

Why These Categories?

Higher paid conversion = writers who invest
Passionate audiences = more archive engagement
Less tech-savvy = won't try to DIY
Personal topics = emotional connection to content

Avoid Initially

Tech/Business: Low paid % (12-14%), will build themselves
Politics: High volume but contentious, low conversion

Lead Generation Pipeline

1. Data Sources

Apify Scrapers — $5-10 for 2K publications
Reletter — Top 50 charts by category
Sidestack — Niche directories
Substack Leaderboards — Official rankings

2. Email Enrichment

Substack Bios — Many list email directly
Apollo.io — $49/mo, 5K credits
Prospeo/Snov — $39/mo alternatives
Social profiles — Twitter/LinkedIn lookup

3. Airtable CRM

Prospects (name, email, category, subs)
Outreach Campaigns
Outreach Log (sent, opened, replied)
Engagement Tracking

Total cost to build 2,000 qualified leads: ~$50-80

Cold Email Template

Subject: Your [category] archive deserves better

Hey [First Name],

I've been writing on Substack for 4 years (600+ posts at Infinite Zest), and I always hated how my best work just... disappeared into the archive.

So I built something: a way for readers to actually explore your entire body of work through conversation. Think of it like giving your archive a voice.

I noticed you've been writing about [specific topic from their recent post] — exactly the kind of rich archive that readers would love to dig into.

Would you be open to trying it? It takes about 5 minutes to set up, and I'd love your feedback as a fellow writer.

Here's what it looks like: [link to demo]

— Luke
infinitezest.substack.com

Key Elements

Credibility first: Lead with your Substack experience
Emotional hook: The pain of archive neglect
Personalization: Reference their actual content
Low ask: Try it, give feedback
No jargon: “AI chatbot” never appears

Subject Line Variants

“Your [topic] posts shouldn't be buried”
“Fellow Substack writer here...”
“What if readers could explore your whole archive?”

Brand Voice: Language That Resonates

❌ Never Say

“AI chatbot” / “chatbot” / “bot”
“AI-powered” (overused, generic)
“Revolutionary” / “game-changing”
Technical jargon (RAG, embeddings, vectors)
Anything that sounds like a pitch deck

We're not selling AI. We're selling deeper reader engagement.

✅ Instead Say

“Let readers explore your archive”
“Give your writing a voice”
“Bring your posts to life”
“Readers can ask questions about your work”
“Create your AskMyStack”

Warm, benefit-focused, writer-to-writer.

Core emotional message: “You pour your heart into these posts. They deserve to be discovered, not buried.”

60-Day Success Metrics

2,000

Emails Sent

20%

Open Rate Target

Reply Rate Target

Paying Customers

Funnel Math

Emails sent	2,000
Opens (20%)	400
Replies (5%)	100
Trials (50%)	50
Paid (50%)	25-50

Revenue Target

50 customers × $50 avg	$2,500/mo MRR
Annual run rate	$30,000 ARR

Stretch: 100 customers → $5K MRR by end of Q1

8-Week Launch Timeline

Week 1

Launch & Reddit

Deploy to app.askmystack.com. Post to r/Substack. Gather initial feedback.

Week 2

Lead Gen Setup

Build first 500 leads (Music, Faith categories). Set up email infrastructure.

Weeks 3-4

Email Campaign 1

50 emails/day to Music & Faith writers. Iterate on messaging.

Weeks 5-6

Expand Categories

Add Sports, Literature, Culture. Scale to 100 emails/day.

Week 7

Optimize & Scale

Double down on best-performing categories. Walter handles follow-ups.

Week 8

Review & Plan

Analyze results. Plan Month 2 expansion (Notes, partnerships).

End of Month 2

Milestone Check

50 paying customers, $2,500 MRR, clear path to $5K

Operational Roles

Walter Handles

Scraping & building lead lists from Apify/Reletter
Enriching emails via Apollo or bio scraping
Drafting personalized email variants
Managing Airtable CRM (logging, tracking)
Follow-up sequences after initial contact
Morning briefings with outreach metrics
Researching new categories to target

Luke Handles

Initial Reddit posts (personal credibility)
Approving email templates before send
Responding to warm replies (personal touch)
Demo calls with interested writers
Strategic decisions on category expansion
Product feedback integration

Recommendation: Create walter@askmystack.com for outreach automation. Luke reviews templates, Walter sends at scale. This keeps luke@askmystack.com pristine for warm leads.

Immediate Action Items

Today (Launch Day)

Deploy to app.askmystack.com
Test full user flow on production
Draft Reddit post for r/Substack

This Week

Post to Reddit (soft launch)
Set up walter@askmystack.com
Pull first 500 leads (Music + Faith)
Warm up email domain
Finalize email templates

Decision Needed

Do you want Walter to have direct send access via walter@askmystack.com, or should he draft emails for your approval first?

Recommendation: Start with drafts for approval, then move to autonomous sending once messaging is dialed in.

Time to Ship.

We have the product. We have the credibility. We have the playbook.
Now we execute.

app.askmystack.com