If you’re going to put an image in your signature footer, at least make sure the dimensions are set correctly so they don’t squish your face.

I literally despise SEO garbage people, so allow me virtually punch Sujith here:

Sujith, you and other SEO garbage people fill my inbox every day with your requests to “review your article” or “write high-quality content for me”, when what you are actually doing it literally actively harming the internet with spam garbage and forcing smart people to invent ways to circumvent your pollution.

So here you go: haha, you look like a dork.

Dissecting a Sales Email

I received this email a few days ago:

I know who Gary Vaynerchuk is. He’s the CRUSHING IT! guy. He’s done more stuff in his life and made more money than I will on either account. Along the way, he’s gained some huge fans. He’s also said some stuff that is was incredibly cringe-worthy and, to me, things that came across as wildly disingenuous. He makes me cringe in the same way I cringe at Corey Feldman. It’s Trump-like in that how did you get so far but are seemingly so dim?

I feel like I would get it more if, for example, I knew him in real life and he was a real charmer. Or if I had some email correspondences with him and I could feel his business savvy oozing out of it. But based on the email above, well, I just don’t get it.

WARNING: I’m doing a bit of bridge-burning here I suppose. By way of general advice, this is a bad idea. But I’m rather fed-up with bad email so I’m calling it out.

Allow me to translate bit by bit.

It’s Gary Vaynerchuk and I’m interested in your brand.

I have literally no idea who I’m emailing. I used to tell people that personally interacting with people was part of the secret of my success, but now I just send out impersonal mass-emails.

We at VaynerMedia.com do $125 million dollars in annual revenue managing digital marketing campaigns for some of the biggest companies in the world. 

I’m flexing. I want you to be super impressed and feel honored even to be reading this email. My Lamborghini is red and my penis 12 inches soft.

We’re expanding our services by offering search engine optimization or backlinks for entrepreneurs and corporations which has had huge social media success. 

I’m hoping you don’t read this too closely. I just said a bunch of buzzwords and you should bask in them. Please don’t think about the fact that SEO is… for… websites, and not social media? And that backlinks is a part of SEO not an “or” thing.

I’d like to ask to pay you by sending an email out to promote it at $5 per every contact email address you can send out. 

I’m trying to get you on the hook for something here, but don’t try to understand what it is. I’m sort of making it sound like I’ll pay you $5 for every single email address on a newsletter mailing list, but there is no way I’m actually going to do that. Like I know some people have multi-million user emails lists, and there is no way in hell I’m cutting a 10 million dollar check for a 2 million user email. Even though it sorta sounds like I will, just wait for this next paragraph that makes more clear that I will not.

I’d be sharing the campaign results with my 15 million plus social media followers which means your business gets exposure across all of my social media channels which means more exposure for you. 

Exposure! You little dingleberries listen to me. Cough up your email lists, I’m gonna put those emails in my motherfucking CRM and email them myself. Then I’m gonna make a fake chart about how good it did and email you that back and tell you that you did dun good, child.


OK sorry sorry—I got off the rails there. I literally have no idea what he’s trying to do here. I’m not going to find out, because I don’t like any part of what I read. But I don’t actually know if it’s actually nefarious, just accidental poor communication, or what. Although I would say buying email addresses of people and sending them shit they didn’t opt into is nefarious territory. Which actually makes some sense. That’s certainly one path to getting rich.

End of Mailplane?

I was a little sad to get this email:

I’m a Gmail user and I really like the Mailplane tabbed interface for doing email on different accounts. There are alternatives (like Shift), but it sounds like all the apps similar to Mailplane will be affected by Google’s changes which they say are trying to fight man-in-the-middle attacks.

But I’m not that sad. I’ll find a new workflow. It won’t make me worse at email.

On the Gmail mobile apps, I can be logged in to multiple accounts in one app and then use the “All Inboxes” feature to see them all at once. I’d like to see that come to the web client (I’m not missing something, right? You can’t do that on the web?).

I’m also thinking Firefox Multi-Account Containers might be a fairly easy way to replicate it. I just have doubts it will be as nice as a dedicated app just for this. For example, I really like how I can just close the whole damn Mailplane window and it doesn’t unload the apps, it just hides the window, and I can bring it back to the exact state it was in just be clicking the icon in the dock. Browsers don’t really work like that. I’d have to more explicitly Command-H hide. Oh well, just some new muscle memory to build.

The One Way

You know what’s a weird email archetype? The one way.

It’s when you get an email from someone that very much wants to tell you something. Maybe they read something you wrote. They saw something you made. They cross paths with some part of your life. They type it all up and send it to you. You get it, read it, and respond to it, but then never hear back ever again. That email they sent was a one-off one-way anomaly.

One-ways feel weird because email is this highly established two-way street where communication flows easily both ways. But in this case, it behaves more as they sent you a letter with 123 black hole avenue as a return address.

If that’s the intention of the email, the respectful thing is to say so.

No need to reply to this email. I probably won't see/read the reply if you do, because of [insert legitimate reason here]. 


Get well-written AI-generated rejection emails that reduce your writing time by 95% so you can focus on the things you love.


Hi (Founder name),

Thanks for waiting! We had the chance to sync up internally after our conversation.

I personally find what you're building awesome, but unfortunately, we're struggling to gain conviction as a result of some of the metrics, but it's great to see a significant improvement since launching.

This is the only thing that matters for you to be a multi-billion $$ business.

Best of luck with the round. Here’s a Medium article we wrote that might be helpful.

(Your name)

Don’t want to

You don’t have to level up to this, you can just say it.

I mean, you probably can’t to your boss, but you can say this to all those other emails you get where you don’t have any particular obligation.

If you think that “I don’t want to” is a bit harsh, you can be honest but still soften it. I told someone the other day, while delivering a “no”, that I’m trying to wrestle some of my personal time back. That’s true, I am. That way it prevents them from reading in between the lines that you don’t want to because you they suck or their thing sucks.

If you think that, don’t answer at all. This is email. While I think answering things is generally good and I’m broadly against bridge-burning, you don’t owe random people asking you for things responses.

My Trust Issues with Small Businesses and Custom Domains

I got a referral the other day to a physical therapist that is good with backs. A literal paper business card. This email was something like this:


Now I’m an indie-web kinda guy for the most part. I’m all about people owning their own websites and taking control over their little slice of the web. And yet. My trust level with random small businesses managing their own email on their own domain is super low. I get this little twang of distrust when I have to type in an email address like this.


Their email was busted.

It could have been anything. They could have let their domain name lapse. The DNS (MX) records could have gotten screwed up somehow. They could have been trying to move to GSuite, for example, and gotten those records wrong. They could be moving hosts and something got funky. Who knows.

That stuff is complicated for me, and I’ve been working on the web for decades.

That’s why even though I like the idea of doing as much as you can yourself on the web, I think using a managed email service is a smart move for most. Even if you do “do it yourself”, you’re leaning on so much rented technology anyway, it’s not that different.

If I see an email like: small-business@hotmail.com – all my doubt is gone on if they are actually going to get that message or not. Heck, I even prefer just seeing an email like that on the website itself (rather than a contact form), because the contact form is just one more bit of technology that can go wrong.

I get the desire to have email on your own domain as well. “It looks more professional” I was just told the other week by someone I was helping out with a website. But there are other pokes too. Like if that small business uses MailChimp, MailChimp will literally tell you that your “from:” email address should be your own domain, not something like Gmail.

The middle-ground for me is using my own domain, but using Gmail on top of it. So I still have to deal with MX records, but once it’s set up correctly, I just never change it. It works for every company I run and every project I have that has a custom domain and email.