[solarisos]

That 'punch in the gut' feeling from a samey subject line is a great way to put it. I think we’ve reached a point where the 'standard' advice for cold outreach (use a catchy hook, keep it short, use AI to personalize) has been so overused that it now functions as a negative signal.

You're spot on that PMF solves many deliverability issues—if people actually want the thing, they'll dig it out of the 'Promotions' folder. But my technical curiosity is about the gap before that: if a startup does have something genuinely useful for a specific person, are they even getting the chance to be seen? It feels like the 'noise' from low-quality AI pitches has forced ISPs to move to a 'guilty until proven innocent' model for any external domain. Google definitely benefits from that shift, as it pushes everyone back toward their walled garden of ads.

[PaulHoule]

Last time I did cold outreach for an enterprise product that didn't quite exist yet (about 10 years ago) I sent hand-written emails to individuals and can't recall not being able to get an audience with someone that I wanted to get an audience with. [1]

Last year I knew somebody in a similar situation who had a long list of "fish that got away" but they were pitching to celebrity bloggers, people in the gatekeeping-idustrial complex, etc. He was getting much worse results but he was pitching something really hard to sell.

[1] looking back I find that hard to believe but I think that selective recall helped me handle the hustle

[solarisos]

Selective recall or not, that 100% success rate from 10 years ago points to a different era of the inbox. Back then, a hand-written email was a signal of 'Proof of Work.’

The problem I'm seeing now is that AI has made 'hand-written' style emails incredibly cheap to forge at scale. If an enterprise lead receives 50 'personalized' emails a day that all look like they took 20 minutes to write (but actually took an LLM 2 seconds), the recipient’s internal filter just shuts down. Do you think the 'gatekeeping-industrial complex' you mentioned is now purely a social barrier, or have the technical filters (spam/quarantine) finally caught up to the point where even a genuinely 'hand-written' cold email from a stranger might never even be seen?

[felixdoerp]

I think this is a very interesting problem. I feel we would already win a lot if we had something like a bot-protection / captcha for inboxes. That little increase in friction would already up the relevancy I feel.

[PaulHoule]

Well the people he was talking to were at places like The New York Times who are so convinced of their superiority that they wouldn't talk to startup royalty (founder of Waze, backed by a16z) who had a polished product, never mind us!

I dunno how bad it is with email. My current adventure in marketing has been a hybrid of in-person and social media, I go “out” as a fox-photographer to get smiles from people, get approached several times a day, hand out a lot of business cards, my fame spreads and I get approached more often. It’s changed my point of view on a lot of things.

[solarisos]

The 'fox-photographer' approach is brilliant because it’s a high-friction, high-signal activity. It’s the ultimate proof that you aren’t a bot.

My takeaway from your story is that the 'inbox' isn't just a technical place anymore; it's a social one. Ten years ago, the barrier was just finding the address. Now, the address is public, but the barrier is 'Proof of Humanity.'

Do you think we’re heading toward a future where B2B 'cold' outreach only works if it's preceded by an offline or social signal? If so, the entire 'Verified List' industry is essentially selling a map to a city that has already pulled up its drawbridges.

[xenadu02]

Do things that don't scale.

No one built a business by starting out with huge email blasts. At least not anytime recently.

You start by finding individuals and addressing them as individuals. When you find one such person who finds your product extremely useful they will often generate leads for you to others who need to solve the same problem. Keep doing that high-touch direct contact.

In other words: sow the seeds.