Be weird

A guide to founder-led outbound (and life)

I am currently running fully automated outbound for Waffle with a >50% reply rate (n = 500+). 90%+ of these replies are positive. Here’s how I do it. But first, a short, necessary detour.

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I’ve given a one-sentence piece of advice that has gotten many friends into HBS + GSB: Be so weird they can’t not interview you.

Everyone who applies to these fancy MBA programs is accomplished. They’ve all done well at McKinsey or Goldman and on their GMATs. They all get stellar recommendation letters. They write compelling essays. By doing all the right things, their applications are indistinguishably bland.

I learned that weirdness wins during my HBS interview. My interviewer spent the interview just trying to figure me out: “Let me get this straight… you have no work experience, played in a metal band, danced Bhangra, and spent your free time wandering around rural Tanzania. Uh… what are you?”

That’s when it clicked: They interviewed me - this barely-above-average middle-class kid from a state school - because I was too weird not to interview. They let me in, probably, for the same reason.

The point? Being weird - “n of 1” - is infinitely more valuable than being “very good” or even “in the top 1%” of anything. This key unlocks many doors in life, but let’s just focus on outbound.

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Founders neuter their weirdness in their outbound messages. In Finding Pull workshops, I’ve seen every flavor of outbound message there is… all of which result in 0% response rates.

There’s the sales haiku, a 20-word message that is so “clever” it can only work for salespeople selling sales courses to (gullible) salespeople:

John — want the secret to hitting Presidents Club this year? Success GUARANTEED - only 4 slots left.

There’s the Hubspot Standard, a message based on a 2017 HubSpot blog post that formally pitches a value prop as if we’re selling spices to a Dutch merchant in 1607.

Dear Sir or Madam, I hope this message finds you well. Have you considered that your business might benefit from Artificial Intelligence (AI)? It could certainly solve some major pain points for your workflows.

There’s the Predictable Revenue Bank Shot, which says “I didn’t do my research, could you do it for me?” (This made sense before we had good sales data.)

Hey - who’s the right person to talk with in your org about customer success?

And don’t get me started on the breakup email, or pointless personalization.

When you use these kinds of messages, you wind up spending months iterating endlessly on messaging that will never work. You stay stuck at 0% reply rates because you’re doing what MBA applicants do: Optimizing for “good” versus “weird.”

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How do you do founder-led outbound that actually works? By leaning into your particular weirdness — sending a message that is so weird they can’t not respond.

My favorite example is from a Finding Pull workshop, where a team’s original message was a bland HubSpot Standard (0% reply rate), and the revised message was this:

Hey - Snoop Dogg invested in us, would love to get you involved too. We’re working on X, open to chat?

This worked, because obviously it did.

Another example that was less weird but still weird enough:

Hey - I’m a 2x CEO building something I've really needed in my other companies: X. In early stages; building a brain trust of smart people to help advise. open to a call?

These messages work because they are weird enough to be interesting. They get you at-bats, and then it’s your job to find intense demand and adjust your targeting + messaging + approach from there.

For now: You have to actually talk to a ton of people, and in order to do that you need messaging that is sufficiently weird they can’t not respond.

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PS:

• I’m back in action next week from paternity leave. Planning the next Finding Pull cohort - learn more here & secure your spot before it’s full!

• Thanks for all the replies last week about Waffle’s attack vector. It seems like people are actually buying Waffle to easily deploy & manage backends on AWS without AWS expertise. Just so happens that SOC 2 compliance is an added benefit. FUN!