I was engineer 12 at SendGrid and left after IPO and subsequent acquisition by Twilio. Being infrastructure and the backing many email marketing companies, we did really well. Kind of like selling shovels in the gold rush. We struggled more on the product front breaking into the much larger marketing space. Learned a lot there leading and scaling teams and scaling the email infrastructure to support over 8 billion daily sends.

I fell in love wirh Zenbe back in 2009 and i’m still angry at Facebook for acquishutting them down in 2010

I’m surprised Hey isn’t mentioned. That’s the only example I know of someone recently trying to reinvent email. Maybe it wasn’t included because it’s part of Basecamp and not its own company. But I think it’s important to discuss if your argument is that “no one has successfully reinvented email”.

Actually recent email innovation I enjoyed is Mimestream, the macOS native client for Gmail. Apple’s smart inbox is half baked but better than nothing. Cloudflare now also has a pretty good email forwarding service.

My first thought was wow - 20% of email startups succeed? That’s actually pretty good.

What's left to conquer in email land?

Most of the large marketing ecommerce/enterprise market was captured via ExactTarget/Salesforce, Oracle/Responsys/Eloqua, IBM/SilverPop/Acoustic, Adobe/Neolane/Marketo by the mid 2010's.

SendGrid/Twilio was another a few years later, Amazon SES is ok, then you have some of the smaller market players (MailChimp, Constant Contact, etc).

Hard to scale/grow a startup in any real way when there are so many fairly well entrenched solutions across industries and company sizes.

Mailbox raising 6M, having a 100M exit and getting called out failure is crazy