Getting to Yes: Effective outreach, business development, and mentorship over the internet

I’m really not into the extensive writing people do about how to hustle as an entrepreneur blah blah blah. But, I’ve been writing hundreds of emails the last few months for a gig I have at an investment fund, and also have made a lot of intros for people/volunteered a lot of my time. Here are some guidelines that I wish were more widely understood:

  1. If someone doesn’t respond, follow up. People are busy. I promise you I’m 10x more likely to respond to a second email asking if I got the first one than the first one from someone that may have gotten in on a very busy day. Boomerang for Gmail is a great tool to help with this.
  2. BCC people when they’ve introduced you to someone. They don’t want to be in your 17-email chain coordinating a meeting.
  3. Thank people. Taking time to make an intro or give advice is something people are happy to give, but they’re way more excited about it when their effort is acknowledged. It often takes more work than you think
  4. Always, if you’re asking for an intro, give people something to use to intro you that’s written in third person. EG, if I were asking you for an intro to Barack Obama, I’d give you something like “Hey Barack. How’s it going. You going to miss Air Force One? I’d like to introduce you to my friend Dan. Dan is doing some really interesting things and I think you should work with him after the Presidency.”
  5. On that note, the double blind intro: ask someone if you can introduce them to someone before just doing it. There could be 20 different, legitimate reasons why they don’t want to be introduced, and they don’t want to be in the awkward position of either taking a call they aren’t in a good position to take, or having to shut someone down who was eager to talk to them.
  6. Keep your emails short. I’m guilty of overly long emails. I mean, this post is already too long. The longer it is, the less likely it will be to get read.
  7. Relatedly: Put a summary at the top, so if it is too long, they at least still get the point.
  8. PROOFREAD: It’s annoying. I wish I got it right every time. I don’t. And, it matters less with close friends/colleagues. But small errors are a sign of sloppiness.
  9. Use smaller words. Seriously. Emails are generally a bore.
  10. To save yourself time, use Canned Responses in GMail for the basic facts of something you’re sharing, BUT:
  11. Make sure to personalize the intro! People don’t read form emails.
  12. As annoying as it is, send personal emails if it’s important, even if you’re sending the same basic intro to many many people. Mass emails for something that takes time, and isn’t necessarily exciting unto itself for the recipient, rarely get read.
  13. Make sure you have your contact info in the signature. It’s professional, helps you get more attention, and who knows what happens if your email gets forwarded around.
  14. Always assume your email will get forwarded, and that the forwarder won’t redact personal details. If you’re writing your friend Sarah to ask her if she would mind connecting you to her friend Alejandro who runs that really cool solar company in Nicaragua, don’t mention how much fun you had at Burning Man last month. Alejandro might pass it on to his friend Roberto who actually runs another solar business — and Roberto may be a good guy, but really conservative, and get turned off by Burning Man
  15. If you’re asking someone for their time, and especially if working with a team, offer them times ahead of time that work for you/your team - and it’s ok if not all members of a big team join. I mentored some college students recently, and they insisted all six students on the team be on the call — and the only times they offered as mutually agreeable were 9PM on Saturday and 7AM on Sunday. Thanks but no thanks — but congrats on being go-getters!
  16. I get a lot of requests to tell people the full version of what it was like starting Runa because of its relevance to the food/beverage company they’re starting. I love telling stories, but I’d rather be as directly useful to someone in the most efficient way possible. Retelling the Runa story, when it’s available online and easily found in a Google search, isn’t the best use of that time. So, if you’re asking someone for advice, please come with specific questions, and put them in the email ahead of time. Someone may be too busy to take a call, but happy to give some quick feedback via email. Goes without saying, make it concise.
  17. This is an old adage, but asking if you can “pick someone’s brain” is annoying AF. Be specific about asking for help, and also offer any way you can support. “picking someone’s brain” is an extractive activity. Nobody wants their brain picked. But they’d often love to give you the gift of their advice. Phrasing matters.
  18. Don’t insist on an in-person meeting. Yes, we both live in NYC, but running around to 10 coffees a day is tough. Please don’t take it personally if I ask to have a phone call, especially if you asked for the meeting. I promise I will pay attention to the call and not be watching Youtube videos of cats in Santa costumes in the background. Though now that I think of it, that video sounds like fun… [UPDATE: I FOUND THE HOLY GRAIL:]
  19. If you are meeting someone in person, do your best to be agreeable about location most convenient for both of you. If you asked for the meeting/a favor/an opportunity to share your product or service, go to that person. It’s the courteous thing to do.
  20. Likewise, if you asked for the meeting, and it’s not super pricey, offer to buy coffee/lunch/yoga class/chia pudding. If someone proposed somewhere pricey for your budget, try to push for somewhere more affordable (but find a better rationale) — and if they insist on the Plaza Hotel, it’s ok to offer to split it. Never assume someone will pay for you, even if you’re 95% sure they will.
  21. Did I mention, thanking someone always puts a smile on their face? Especially if you make it personal. Flattery never hurts, as long as it’s genuine.
  22. Always offer whatever you can to support someone else — and not as a quid pro quo. It’s just the good thing to do.

Go get ‘em!