Is It Ok To...email, email,email

Ok, Kelly,

How many times is it approach to contact any investor with feedback on a company submitted before it gets annoying? Things get lost in email and people are super busy, so what's the right cadence? 3 emails? once a week?

- Founder Fiona

Ok, Fiona -

Your networking question sounds like it is coming from a rather anxious-eager-to-please-and-get-it-right-cause-I-need-the-money-active-fundraising perspective. Am I right? If yes, my answer MAY not be the quick-fix salve you’re seeking.

Because in two word answer (without more facts and my very strong opinion that what is the right communication strategy for one investor is NOT the strategy for every investor), to your communication cadence question, is…it depends.

Cadence depends on (and this is BY NO MEANS a full, and complete list of factors which could have an effect on the investor’s response rate to your email outreach):

• your relationship with the investor (prior connection, just met, old buddies, or a WTFRU reaction to your cold outreach);
• what you know about how the investor seeks new investments (is their investment funnel primarily through their network or do they actively welcome unsolicited inbound pitches);
• what you know about how the investor operates (do they hand out their email address freely - then immediately forget how to log into it, are they preoccupied with putting out fires with their exiting portfolio companies…);
• how they are investing right here, right now at this very moment (sector, series, status of their fund, state of the market, treasury bond yields etc.);
• the month of the year you’re trying to get their attention (vacations, holidays, school breaks etc. sideline the best of intentions and email inboxes); and
• insert any number of business, technology, personality and/or life factors here.

Ok, with so many unknowns working against your self-imposed fundraising timeline, what’s an anxious founder to do?

Focus on what you can control.

Here’s what immediately pops to mind for me, as I ponder your situation:

1. You control the agenda for your venture. Remind yourself of this each time you go to your laptop to craft an email to an investor asking for feedback or money or both. Does the investor operate on the same timeline as you, who knows but I suspect not. Remind yourself that while it is your venture and your agenda, you can’t impose these two items on someone else simply because you stated it to be so in an f’g email.
2. You should remind yourself (constantly) that there is no “any investor”. An investor is not an ATM. There is not a one-size-fits-all-communication-outreach formula that you can plug your pitch into which then causes money to suddenly spit out in the amount, on the terms and in alignment with your desired timing.
3. You should also remind yourself (frequently) that no one cares about your product-service-venture as much as you do. Not your mom. Neither your first employee nor your first paying customer. You. You f’g love your venture the most. You love it more than anyone - as you should, as that love and belief in what you are doing/building/creating/disrupting provides the stamina to get you through the lack of responses to your outreach and other fundraising BS.

So, after reminding yourself of 1, 2 and 3 above (I know, I know, once again I’m terribly f’g sorry there is not a handy-dandy communication checklist for this journey through fundraising hell you have embarked on), do this:

Assume best intentions (i.e. the investor is not a rude asshat, she or he just lost your email or the dog ate it).

Craft a personal message - as in you (not a template or “a friend used this email and it worked for them”), you should write the type of email which if the inbox tables were turned, you would not be thinking ‘who is the asshat sending me this!” upon reading your own email.

After the first email, send a “just popping this to the top of your inbox” (forwarding the first email) email, after that you may want to add a “hey, the reason I’m enthusiastic to talk to you about my venture is__________________ [networking pro-tip: this is where insights on the investor come in handy!], if that is of interest to you, I’d love to get your feedback on what I’m building”.

Now whether there should be additional email outreach to the non-responsive investor after this “hey” third email - sigh - I return to my original answer - it depends. So Fiona, you can email me more facts, as for now, this is what I’ve got.

Ok?

K.

p.s. Got a Is It OK to… question, I’d love to hear from you.