My first money in was from a local angel investor. He committed very early over a lunch with a handshake, before there was even a clear plan. I was ecstatic. I called my wife (girlfriend then) and gushed. I e-mailed the team and told them we got our first money committed. I was on top of the world!
Then…nothing happened. I couldn’t get him to respond to my e-mails to sign the documents. I even sent him echosign documents so it was one click for him to sign. I thought something was wrong. I thought he was backing out of the deal. I sent him some emails of questionable tone trying to get a response. I was totally crushed!
Josh said: Calm down Amir. He’s a good guy, and his word is good. He’s just very busy, and you’re not a priority.
Then he gave me the advice:
Just be persistent.
Josh laid it out for me:
- Let a few days go by, and then remind him.
- Let a few more days go by, and remind him again.
- After a few of these just start reminding him every day until he signs the docs or he tells you to go away.
Of course, it worked! Over the course of about 3 weeks I reminded this investor about 7 times. Eventually I did get a response from him and we scheduled lunch. I brought the documents with me to lunch and we signed after a great conversation. I prefer to use e-signatures but in this case I just wanted to get it done.
It turns out the investor was in the process of launching a new product and was just entirely underwater. It was nothing personal and his word was good. He has since become a huge resource, and mentor to me. Now that I am a priority to him I get an immediate response on any questions I have.
When I first heard the advice about persistence I was very worried about turning the investor off by being a nuisance, or appearing needy. This is a real fear but I’ve since learned there is a right way to be persistent - without being a turnoff. In fact, done well, it can strengthen the connection.
With some guidance and a long process of refinement I’ve arrived at a formula that has worked very well for me. Here’s how I remind people about a commitment they’ve made to me (not just investors):
- I’m extremely friendly and my tone is entirely positive.
- I’m short and to the point.
- Here is the most important part: I’m never even slightly annoyed.
Even if I want to scream with frustration I don’t allow that tone to seep into my reminder e-mails.
Here is a (slightly doctored) sample of an actual email I sent the investor in question:
Re: Your investment in lark.io
Just wanted to keep this at the top of your inbox. Hope to speak soon.
Josh’s advice freed me to tap my natural relentlessness. I was pulling my punches because I was afraid of being too pushy. (Rightfully so; It is entirely possible to be too pushy!). I’ve since been able shed that fear to great reward. I have turned several “Nos” into “Yes” by being persistent.
What I’ve learned from this and future experiences:
- Persistence works
- There is a right way to be persistent
- Once you’ve gotten a yes treat it like a yes until you explicitly get a no.
For the curious, that first check was the hardest to close and I’ve never had to work quite that hard since.
A great follow up read on this topic is Y Combinator's Handshake Deal Protocol.