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SendGrid (acquired by Twilio for $2B [1]) famously had their application rejected, and their later success caused YC to update its selection process. From this

SendGrid (acquired by Twilio for $2B [1]) famously had their application rejected, and their later success caused YC to update its selection process. From this Quora answer [2]: > Apparently, only one partner, Robert Morris, reviewed the SendGrid application, and he gave it a highly negative score, calling it a "spam company." That pushed it so far down the application queue that no other partner reviewed it. Paul talks about how they changed the application process after that so that any applications negatively scored by Robert would also get reviewed by Paul. (Interestingly, venture returns skew so highly to big winners that SendGrid's objectively huge outcome would not even have had a material impact on YC's current portfolio value of nearly $1T [3]. I'm not aware of any current $10B+ companies that were rejected by YC, though there may be some.) [1] https://www.zdnet.com/article/twilio-to-acquire-email-api-platform-sendgrid-for-2-billion/ https://www.zdnet.com/article/twilio-to-acquire-email-api-pl... [2] https://www.quora.com/Why-was-SendGrid-rejected-from-YCombinator/answer/Brian-Chu-2 https://www.quora.com/Why-was-SendGrid-rejected-from-YCombin... [3] https://www.ycombinator.com/ https://www.ycombinator.com/

Xx25 4y ago
> YC's current portfolio value of nearly $1T I don't think you mean portfolio value. That would mean YC actually owns $1T in the companies they funded, at their current valuation. The following on YC front page is more meaningful: "Our companies have a combined valuation nearing $1T."
- edouard-harris 4y ago
  Yes, the combined valuation number you cited is the one I was referring to. You're right that it's not correct to call this "portfolio value"; thanks for pointing out the mistake. (But it is still the correct number to compare SendGrid's $2B exit value to.)
colordrops 4y ago
> calling it a "spam company" Was he wrong? Honest question. Looking at their homepage I'm guessing a good portion of unsolicited emails in my inbox went through SendGrid.
- _8j50 4y ago
  They are used by legit businesses and they do a lot in containing spam, so yeah he was wrong.
  - FreakLegion 4y ago
    I don't know or care about spam, but SendGrid is one of the most prolific sources of malware and phishing emails out there. Their opaquely rewritten URLs are an annoyance to security teams everywhere, enough that I've seen enterprises simply block ct.sendgrid.net or any URL with /ls/click, which isn't the kind of thing large companies typically have the will to do.
    - _8j50 4y ago
      I work with phishing emails, I love sendgrid, your sandbox sucks if you are not detonating URLs to see where they lead to and rewriting means as soon as sendgrid finds out about an account sending spam/phishing they can disable all those links which isn't doable when they are doing the same thing with multiple domains, urls, subject lines, attachment names,etc... leaving you with live phishing links you don't know about in someone's inbox. Any modern paid email protection service will also work nicely with sendgrid and the like. You worked at orgs that didn't have the best decision making if they are blocking sendgrid. Talk about throwing the baby with the bathwater. Lazy mitigations made bad security. This is especially true here since sendgrid is hardly the only one of their kind so you will play whackamole blocking all kinds of legit services because... you don't have toolimg that can follow 301's??
      - I_dev_outdoors 4y ago
        What does your phishing email filtering pipeline look like?
- defanor 4y ago
  As a bit of anecdata, I received a spam message from SendGrid about 3 weeks ago (while just a few spam messages per year make it through), and that's how I've learned about them. But I guess they won't stay out of DNSBLs for long if the portion of spam messages will be particularly high.
numair 4y ago
The most amazing thing about this story is that Robert Morris, of all people, was the one who dismissed it as a spam company. Ironic, hilarious, something like that… https://en.m.wikipedia.org/wiki/Morris_worm https://en.m.wikipedia.org/wiki/Morris_worm
- rmetzler 4y ago
  Yeah, viral is just an adjective describing growth. Unfortunately it’s associated with both positive and negative impact.
petrbela 4y ago
Notably, SendGrid went through the Techstars accelerator instead. One of their mentors from the Techstars program [1], Jim Franklin, later became SendGrid's CEO and helped the technical founders grow the company towards the success they eventually achieved. [1] https://davidgcohen.com/2020/09/19/a-review-of-the-first-eleven-techstars-unicorns/ https://davidgcohen.com/2020/09/19/a-review-of-the-first-ele...

Xx25 4y ago

> YC's current portfolio value of nearly $1T I don't think you mean portfolio value. That would mean YC actually owns $1T in the companies they funded, at their current valuation. The following on YC front page is more meaningful: "Our companies have a combined valuation nearing $1T."

edouard-harris 4y ago
Yes, the combined valuation number you cited is the one I was referring to. You're right that it's not correct to call this "portfolio value"; thanks for pointing out the mistake. (But it is still the correct number to compare SendGrid's $2B exit value to.)

colordrops 4y ago

> calling it a "spam company" Was he wrong? Honest question. Looking at their homepage I'm guessing a good portion of unsolicited emails in my inbox went through SendGrid.

_8j50 4y ago
They are used by legit businesses and they do a lot in containing spam, so yeah he was wrong.
- FreakLegion 4y ago
  I don't know or care about spam, but SendGrid is one of the most prolific sources of malware and phishing emails out there. Their opaquely rewritten URLs are an annoyance to security teams everywhere, enough that I've seen enterprises simply block ct.sendgrid.net or any URL with /ls/click, which isn't the kind of thing large companies typically have the will to do.
  - _8j50 4y ago
    I work with phishing emails, I love sendgrid, your sandbox sucks if you are not detonating URLs to see where they lead to and rewriting means as soon as sendgrid finds out about an account sending spam/phishing they can disable all those links which isn't doable when they are doing the same thing with multiple domains, urls, subject lines, attachment names,etc... leaving you with live phishing links you don't know about in someone's inbox. Any modern paid email protection service will also work nicely with sendgrid and the like. You worked at orgs that didn't have the best decision making if they are blocking sendgrid. Talk about throwing the baby with the bathwater. Lazy mitigations made bad security. This is especially true here since sendgrid is hardly the only one of their kind so you will play whackamole blocking all kinds of legit services because... you don't have toolimg that can follow 301's??
    - I_dev_outdoors 4y ago
      What does your phishing email filtering pipeline look like?
defanor 4y ago
As a bit of anecdata, I received a spam message from SendGrid about 3 weeks ago (while just a few spam messages per year make it through), and that's how I've learned about them. But I guess they won't stay out of DNSBLs for long if the portion of spam messages will be particularly high.

numair 4y ago

The most amazing thing about this story is that Robert Morris, of all people, was the one who dismissed it as a spam company. Ironic, hilarious, something like that… https://en.m.wikipedia.org/wiki/Morris_worm https://en.m.wikipedia.org/wiki/Morris_worm

rmetzler 4y ago
Yeah, viral is just an adjective describing growth. Unfortunately it’s associated with both positive and negative impact.

petrbela 4y ago

Notably, SendGrid went through the Techstars accelerator instead. One of their mentors from the Techstars program [1], Jim Franklin, later became SendGrid's CEO and helped the technical founders grow the company towards the success they eventually achieved. [1] https://davidgcohen.com/2020/09/19/a-review-of-the-first-eleven-techstars-unicorns/ https://davidgcohen.com/2020/09/19/a-review-of-the-first-ele...