Follow-Up Sequence: Cold Outreach to Technical Founders at Stealth AI Startup

Prospects: 3 technical founders at stealth AI startup
Current Status: First contact 5 days ago, no opens yet
Sequence: 9 touchpoints over 20 days (aggressive cadence with daily touchpoints)
Channels: Email, LinkedIn, YouTube

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Touchpoint 1 (Today - Day 6 from original) - Email

Subject: Quick thought on your stealth AI project

Hi [Name],

I know you’re heads-down building right now. That’s exactly why I’m reaching out - most stealth-mode technical founders I talk to are so focused on R&D that they miss early signals from the market.

I’ve seen three startups this year avoid 6+ months of wasted engineering because they validated one assumption early. Would a 10-minute conversation this week be worth your time?

If now’s genuinely not the right moment, just reply “not now” and I’ll circle back in Q2.

[Your Name]

Why it works: Acknowledges stealth mode reality, references specific founder behavior, permission-based exit, short and direct

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Touchpoint 2 (Day 7) - LinkedIn Connection Request

Hi [Name] - Reaching out about [specific technical problem your solution solves]. I’ve worked with 3 other AI-focused stealth startups at similar stage. Worth connecting?

Why it works: Different channel increases visibility, mentions relevant experience, casual and respectful tone

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Touchpoint 3 (Day 8) - LinkedIn Message (if connected)

Saw you’re building in the AI space. I won’t pitch you - just wanted to share this 2-minute breakdown of how [Company X] avoided a massive technical debt issue during their stealth phase: [YouTube link]

No ask here. Just thought it might be useful given your stage.

Why it works: Pure value-add with no request, demonstrates understanding of their stage, introduces video content naturally

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Touchpoint 4 (Day 9) - YouTube Video + Email

Email Subject: 60 seconds on what I’m actually proposing

[Name] - Rather than keep sending text, I recorded this quick video explaining exactly what I’m suggesting and why it might matter for stealth-stage AI startups: [YouTube link]

If it’s not relevant, no worries at all. Just wanted to be crystal clear.

Video Script (60 seconds):
“Hey [Name], [Your Name] here. I’ve reached out a few times but I realize I haven’t been totally clear on what I’m actually proposing. [30 seconds explaining your specific value prop for stealth AI startups, referencing their tech stack or problem space]. That’s it. If this sounds useful, reply to any of my emails. If not, I’ll stop here. Thanks for watching.”

Why it works: Shows effort and personalization, video stands out in inbox, humanizes outreach, gives clear next step

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Touchpoint 5 (Day 10) - Email (Competitive Intelligence)

Subject: Are you tracking what [Competitor/Adjacent Company] just launched?

[Name],

Not sure if you saw this, but [Competitor in AI space] just announced [specific feature/funding/hire]. Given what I know about the stealth AI space right now, this could impact your launch timing.

I have thoughts on how this shifts the landscape - happy to share if useful.

Either way, figured you’d want to know.

Why it works: Provides genuine competitive intelligence, positions you as industry insider, creates urgency without being salesy

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Touchpoint 6 (Day 13) - LinkedIn Message (Direct Question)

Quick question: Should I keep trying to connect with you, or is this just bad timing?

I’ve reached out 6 times across email/LinkedIn. If you’re genuinely too heads-down right now (totally get it), just let me know and I’ll ping you in 3 months instead.

If you ARE interested but swamped, I can wait. Just need to know either way.

Why it works: Permission-based, acknowledges persistence without being pushy, gives three clear paths forward

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Touchpoint 7 (Day 15) - Email (Case Study: No Ask)

Subject: How [Similar Stealth Startup] reduced their AWS bill 60% before launch

[Name],

I know I’ve been persistent. This is my last value-add with no ask.

Worked with a stealth AI startup last year that was burning $40K/month on infrastructure during dev. We helped them restructure before launch and cut that to $16K. The full breakdown is here: [link to case study]

No pitch. Just sharing in case the AWS bill is getting painful.

Why it works: High-value content specific to their situation, acknowledges persistence, genuine “no ask” builds credibility

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Touchpoint 8 (Day 17) - Email (1-2-3 Framework)

Subject: Last check: 1, 2, or 3?

[Name],

I’m going to guess one of these is true:

1. Not interested - doesn’t fit what you’re building
2. Interested but slammed - too heads-down on product right now
3. Interested but need more context - want to understand the value better

Can you just reply with 1, 2, or 3?

If it’s #2, I’ll follow up in April. If it’s #3, I’ll send you a detailed breakdown instead of these short messages.

Why it works: Makes responding incredibly easy (one character), shows understanding of their constraints, offers tailored next steps

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Touchpoint 9 (Day 20) - Final Break-Up Email

Subject: Last email from me

[Name],

This is genuinely my last message. I’ve tried 8 times across email, LinkedIn, and even a video. That’s either impressive persistence or borderline harassment depending on your perspective.

If your AI project reaches a point where [specific problem you solve] becomes a priority, feel free to reach out. I’ll be here.

And if you have 30 seconds: What could I have done differently in this sequence to actually get your attention? Your feedback would genuinely help me stop bothering technical founders who are clearly not interested.

Best of luck with the launch.

[Your Name]

P.S. - If you DO want to talk after all, just reply “yes” and I’ll set something up immediately.

Why it works: Genuine break-up, asks for feedback (humanizing), leaves door open without pressure, self-aware humor about persistence

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Execution Calendar

Day	Date	Channel	Message Summary	Status
6 (Today)	[Insert Date]	Email	Stealth mode value prop	SEND NOW
7	[+1 day]	LinkedIn	Connection request	Remind
8	[+2 days]	LinkedIn	YouTube case study share	Remind
9	[+3 days]	YouTube/Email	60-sec video explanation	Remind
10	[+4 days]	Email	Competitive intelligence	Remind
13	[+7 days]	LinkedIn	Permission check-in	Remind
15	[+9 days]	Email	Case study (no ask)	Remind
17	[+11 days]	Email	1-2-3 response framework	Remind
20	[+14 days]	Email	Final break-up	Remind

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Multi-Stakeholder Threading (3 Founders)

Days 6-10 (Early Touches)

• Send individualized emails to each founder with role-specific angles:
  • Technical founder: Infrastructure efficiency, technical debt avoidance
  • Product founder: Customer validation, avoiding building wrong thing
  • Business founder: Competitive positioning, launch timing
• Vary LinkedIn connection requests by 1 day each to avoid looking automated

Days 13-15 (Mid-Sequence)

• Continue 1:1 threading - don’t loop them together yet
• If ONE founder responds, ask if you should include others
• If ZERO responses, mention: “I’ve reached out to [Co-founder Name] as well”

Days 17-20 (Late Sequence)

• Consider ONE group email to all three with subject: “Last attempt - looping in [Name], [Name], [Name]”
• Creates social accountability - founders often respond when peers are CC’d

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Response Handling Guide

Early Response (Touchpoints 1-4):
They were genuinely heads-down; persistence paid off. Say: “Thanks for getting back - I know stealth mode is intense. Want to do 15 minutes this week?”

Mid Response (Touchpoints 5-7):
Multiple touches needed - normal for technical founders in stealth. Respond warmly and reference their pain points.

Late Response (Touchpoints 8-9):
The break-up email worked. Say: “Hey, the break-up email always works! Let’s find 15 minutes.”

No Response After Full Sequence:
Set 3-month reminder. Monitor for funding announcements, product launch, or hiring signals. Re-engage with: “Congrats on [milestone]. Back in [Month] I reached out during your stealth phase - figured now might be better timing.”

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Technical Founder Adaptation

Communication preferences:

• Direct language, no fluff, no marketing speak
• Proof over claims (case studies > testimonials)
• Async-first (prefer written breakdowns over “quick calls”)

Pain points for stealth AI startups:

• Infrastructure costs spiraling during development
• Technical debt accumulating before launch
• Competitive landscape shifting while heads-down building

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Expected response rate: 15-25% (at least 1 of 3 founders responds)