Follow-Up That Doesn’t Feel Spammy: Timing, Tone, and Cadence for Investors

September 12, 2025 · Founder DIY

TL;DR — The Cadence Card (Copy/Paste)

The 2×2×2 System

2 bumps max per investor thread.
2 angles only: new proof or better fit (portfolio/thesis).
2 time options in every ask.

Default Timeline (edit to your pace)

Day 0: First message.
Day 3–5: Bump #1 (new proof or clearer fit).
Day 7–10: Bump #2 (polite close + tiny CTA).
Stop. Move on. Revisit after a real milestone.

Ready-to-Send Scripts

Bump #1 — New Proof (2–3 lines)
“Quick update, [Name]—[new metric/logo] since last note. Still happy to do a 15-min fit check. Free [Day/Time 1] or [Day/Time 2]?”

Bump #1 — Fit Angle (Portfolio/Thesis)
“Noticed your [thesis phrase / PortfolioCo] focus. We help [same buyer] with [product]. Current proof: [metric/logo]. 15-min to compare notes [slot 1] or [slot 2]?”

Bump #2 — Polite Close
“Looping this once and parking if not a fit. Can send a 5-slide teaser or hop on 15-min [slot 1] / [slot 2]. Either way—thank you for the time.”

After a Call — Next Step Summary
“Great chat, [Name]. Recap: [1 line problem] → [1 line solution] → [proof]. Next step: [your ask]. Open [slot 1] / [slot 2] to confirm?”

“Later” Response — Milestone Follow-Up
“Got it—thanks for the quick read. I’ll circle back after [milestone + date] with fresh numbers. Cheering from the sidelines till then.”

Do / Don’t

Do: keep to 2–4 short lines, one clear reason to care, one tiny ask.
Do: change angle on each bump.
Don’t: send daily nudges. Don’t add new asks mid-thread.
Don’t: dump a calendar link without offering two human time options.

Why follow-up works (and when it doesn’t)

People are busy, not rude.

A gentle bump helps them decide quickly.
It respects their time.
It shows you execute.

But follow-up only works when the fit is real. If your list is off, even perfect bumps will fail. Fix targeting first, then cadence.

Timing windows (simple rules)

Send during work hours in the investor’s timezone.
Space bumps by 2–5 days so you don’t stack pressure.
Match your bump to something new (a metric, a customer, or a clearer fit).
Avoid weekends for first touches; use them for drafting, not sending.

Tone and length (how to sound human)

Short sentences. Plain words. No hype.
Lead with one reason to care.
Ask for a 15-minute fit check, not a long meeting.
Offer two exact time options. Add a link only as a fallback.

The 2×2×2 system in action

Two bumps: Enough to be persistent, not pushy.
Two angles:
1. New proof (fresh metric/logo, pilot, velocity).
2. Better fit (portfolio adjacency or thesis mirror).
Two time options: Reduces back-and-forth and speeds booking.

Templates by situation

They accepted but never replied
“Thanks for connecting, [Name]! [user] use us to [outcome]. Proof: [metric/logo]. Open to a 15-min fit check [slot 1] / [slot 2]?”

They viewed the message but didn’t answer
“Saw the view—appreciate the look. Since then: [new proof]. Still happy to compare notes for 15-min [slot 1] / [slot 2]?”

They asked for a deck first
“Sharing a 5-slide teaser here. If it resonates, we can do a 15-min fit check [slot 1] / [slot 2] to tailor the full deck.”

They said ‘not now’
“Understood—thank you. I’ll circle back after [milestone/date] with fresh numbers. If you’d like, I can send monthly snapshots instead.”

Post-meeting nudge
“Following up on our call: [one-line recap]. As discussed, next step is [ask]. Does [slot 1] / [slot 2] work to finalize?”

Cadence by investor type (light guidance)

Angels: faster cycles. Try Day 3 then Day 7.
MicroVCs: similar pace. Day 3–4, then Day 8–10.
HNIs: relationship-led. Keep tone warmer, spacing 4–5 days.
Family Offices: slower review. Space 5–7 days and keep updates tidy.

Quality gates before every bump

Do I have one new thing to say?
Is my ask still 15 minutes with two slots?
Is my tone calm and brief?
If they pass, do I know when I’ll return (after which milestone)?

What not to do (ever)

Don’t send more than two bumps on the same thread.
Don’t stack multiple asks (intro + NDA + deck + meeting).
Don’t argue with a “no.” Thank them and move on.
Don’t fake urgency. Let the numbers speak.

Simple tracker (columns to copy)

Update it once a day. Patterns show up fast when you label the angle used.

Your 7-Day Follow-Up Plan

Day 1: Label every open thread with next touch date and angle.

Day 2: Send Bump #1 to 5–8 A-list investors.

Day 3: Log replies. Book calls. Draft teasers if asked.

Day 4: Refresh proof lines (one metric/logo). Re-score list if accept% is low.

Day 5: Send Bump #2 to non-responders.

Day 6: Add 5 new A-list names; reset angles for next week.

Day 7: Review data. Keep what worked. Cut what didn’t. Celebrate one small win.

FAQ

How long should a follow-up be?
2–4 lines. One reason to care. One tiny ask.

What if I have no new proof?
Switch to the fit angle (portfolio/thesis). Or wait until you have a real update.

Should I keep bumping if they ghost after a call?
Send one clear next-step message. If silence holds, set a milestone re-touch date and move on.

Is it okay to send a calendar link?
Yes, but after offering two human time options. Links are a fallback, not the opener.

Final word

Polite persistence wins.

Two bumps. Two angles. Two time options.

Short, clear, human.

Then let your numbers—and your fit—do the rest.