Stop sending 100 DMs. Try this instead.

A founder recently told me they sent 100 cold DMs.
Zero replies.

Their instinct? “Maybe I just need to send more.”
Another founder exclaimed, “Maybe never do outreach again!”

Mine? Do not send 100 outbound messages at once.

When you are a new founder in the $0-1 stage, statistical significance does not matter.

You have to assume that you are going to be wildly wrong about at least one, usually most, of the following strategic components:

1. Customer segment - who you selected to message

2. Positioning - why you are better than alternatives

3. Messaging - what you actually said

4. Playbook - tools, subject line, follow-up, etc.

To figure out which of these needs iterating, you need clear signals from real humans who might become your first paying customers.

That’s why I always recommend: step 1 - articulate your go-to-market fundamentals (4 components above are some of the key ones), and step 2 - micro-testing.

This 2-step process will help you get clear on what you are testing so you can run the tiniest experiment to (in)validate core components.

For outreach, here’s what the micro-testing process could look like:
✔️ Send 10 messages
✔️ Track responses (leading indicator = reply, lagging = sale)
✔️ Hypothesize why it worked, or didn’t
(this is where you refer back to the fundamentals you were testing)
✔️ Double down on what works
✔️ Go drastically different with what doesn’t

This approach saves time — but more importantly, it builds clarity.
You learn why something worked (or didn’t) and you can get sharper with every round.

If you’re not sure how to structure your first outreach micro-test, try this:

• Pick one very specific customer segment

• Write 10 messages that brings your positioning to life
  (Pro tip: when getting started, I suggest writing custom messages to each person but staying true to your core positioning hypothesis)

• Track responses in a simple sheet: Yes, No, No Response

• After 10, pause to adjust before sending more

Here’s the key to making this work: you have to commit to sending these messages consistently. You have to work past the cringe - and other excuses like “I don’t have time” 🙄 and just hit send.

(I discovered that working through outreach avoidance can be such a big blocker for founders, that I added outreach accountability sessions inside the Founder-Led Marketing Club for this summer!)

What’s stopping you from making meaningful progress on getting more happy paying customers? Hit reply to share your blockers. Maybe it’ll inspire my next newsletter and you’ll get the advice you need to get unblocked. 🙂 

Rooting for you!
Sweta
CEO @ Happy Paying Customers

P.S. If you haven’t yet created your go-to-market plan - your outreach is unlikely to work - or you won’t know what to adjust / replicate. I am not talking anything fancy, just articulate your fundamentals — your customer segment, positioning, pricing, and repeatable playbook. If you want a proven go-to-market design methodology used by 80+ founders to find and keep their early customers, get the GTM Design Pack.