Why Saying No Is Hard

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This post originally appeared on The New Hive a year ago this week.  

Being an investor isn’t easy for a number of reasons. But the hardest part for me is saying “No.” I meet hundreds of entrepreneurs each year, and at RRE Ventures we invest in only a small percentage of them. VC’s generally invest in less than 1% of companies they meet. So if you do the math, you know I have to say “No” a lot.

There are countless reasons why we choose not to back an early stage venture. Market size. Wrong team. Bad timing. Competition. Traction. Lack of monetization. Little or no competitive advantage. Outside our expertise. Valuation. I could go on. 

But regardless of whether I exchange a quick email with a founder or spend hours getting to know him or her, passing is the worst. It’s the only part of my job that I truly hate. And it’s not just because I lose the option to invest down the road. I hate passing because my daily work with entrepreneurs has given me a good look into their struggles…what founders sacrifice daily to ensure that their company is in a better place tomorrow than it is today. It becomes personal, emotional…it’s only human to feel for the founders who…

  • Sleep on an air mattress or couch
  • Max out credit cards
  • Part ways with a cofounder
  • Drop out of school
  • Borrow money from family and close friends
  • Spend days, weeks and months on the road
  • Miss family events and moments
  • Relocate, thousands of miles from home
  • Fight for a spot in an accelerator
  • Sell a product that doesn’t yet exist
  • Lay awake at night
  • Spec, wireframe, code for countless days, nights and weekends
  • Hear family and friends call you crazy
  • Overcome nerves before big meetings
  • Work around the clock for virtually no pay
  • Interview dozens of candidates to fill an open role
  • Kiss away virtually all of your “free time”
  • Pull all nighters to hit deadlines
  • Hear “NO” over and over again
  • Have an investor back out in the 11th hour
  • Stalk bloggers to get some press
  • Volunteer at a conference to get free entry
  • Miss another vacation
  • Sell prized possessions for startup capital
  • Wait for months to get that first contract signed
  • Quit your well paid job
  • Pivot again to nail product market fit
  • Show up to work when you’re sick or down
  • Are the first one in and the last one out
  • Pray you’ll get that lucky win
  • Cold call hundreds of potential customers for just one “Yes”
  • Break up with your significant other 

I think you get the point. Founders endure enormous struggles just for a chance to pitch an investor like me. I recognize it, and I take it very seriously.  So much is on the line.  

That’s why it’s so hard for me to say “No.”

The Author

A VC in NYC

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