An amazing founder DM’ed me last week. I knew this deal wouldn’t last. Here’s the exact timeline — from cold X message to wire transfer in just five days…

Tracking a Recent Investment, Minute by Minute

Tuesday, June 23:

1:42pm: Cold X message received

4:49pm: I reply and ask for Calendly link

10:22pm: Calendly link arrives

11:00pm: I book first open slot

Wednesday, June 24:

10:30am: Meet with founder, promise a decision by EOD Thursday

Thursday, June 25:

3:47pm: I request allocation

4:17pm: Founder confirms allocation received

Saturday, June 27:

2:30pm: Docs and wiring instructions received

Sunday, June 28:

5:24pm: Docs signed, wire transfer initiated

Why Speed Is Critical for Investors

I’ve been at this for five years now. I know what I’m looking for.

When I see it, I move fast.

Some investors take 3 weeks to respond to an e-mail. At that point, you’re not competitive.

Is a great founder going to wait 3 weeks? By that time, the round will be full.

But What About Due Diligence? 

Diligence still matters. I looked into this startup quite a bit, reading reviews, digging into team backgrounds, etc. 

But for a small, early stage check, diligence can’t drag on forever. 

When I see a great deal, I work late into the night doing diligence. Then, I sleep on it.

That’s a trick I learned from Hetty Green, the “Witch of Wall Street”. She never made an investment without sleeping on it first. 

By the next day, I have an answer.

Wrap-Up

Founders are used to hearing “no.” What’s worse is hearing nothing. 

If I’m not ready to invest, I give a quick “no” or “not yet”. I don’t want to waste their time. 

But when that rare deal makes my heart race, I’m not waiting around.

More on tech: 

You’ve Got Your First Customer. Now, How Do You Raise Money?

Is Y Combinator — Gasp! — Actually a Bargain Now?

I Left $157,000 on the Table: How I Missed a Great Investment

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