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!

Luckily I was able to find some time to speak with my friend and mentor Josh Baer (hi Josh) over coffee at the Capital Factory. I explained the situation and Josh saw the look of panic on my face.

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 Hey soandso, Just wanted to keep this at the top of your inbox. Hope to speak soon. Thanks!

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.

