What Are Some Signs You Should Give Up On Your Startup?

I drove home from Sand Hill Road. We had just been turned down. Again. This was the 63rd VC that decided not to invest in our company.

And this rejection was particularly vicious. We had gone through weeks of diligence, and the last thing we needed to do was present to the full partnership.

Then, on Monday morning, we were told they were passing about two hours before we were supposed to present. It was a crushing blow.

The partner leading the deal asked if I wanted to debrief with him. I knew whatever I was going to hear was not going to pleasant, but I said yes.

The partner told me the reason they weren’t investing was due 100% to me. He said the background checks they performed on me “were the worst ones ever.”

“No one we talked to thought highly of you,” he said.


So there I was driving home in the slow lane on 280 watching the traffic fly by at 75MPH. I was just trying to keep it together until I got home.

I was a wreck to say the least.

I got home, took off my jacket and I started crying. I asked myself over and over again, “What have I done?”

Throughout my journey well meaning people that cared about me had been telling me to give up. They weren’t wrong.

After all, how much rejection can one person take?

But I couldn’t quit. At least not yet. At least not until I played out the hand.

My feeling was I didn’t want to have any regrets if we failed. I was going to leave everything I had on the field.

I thought, as I picked myself up for the 63rd time, about the progress we were making:

  • The team was much strong, and…
  • The pitch was much better, and…
  • It seemed like the investor reaction was much better.

I talked with one my cofounders over the weekend about what happened. He asked me, “Do you still want to keep going?”

I said that I did.

There were two more VCs left on our list to meet. So we set up a meeting with the 64th and 65th VCs on our list.

The 64th VC ended up investing after just three meetings. We didn’t even have to pitch the whole partnership.

Only you know when it’s time to give up. I’m glad I didn’t listen to the well meaning people that suggested I quit.

I would have never known the incredible joy and happiness of working with an incredibly talented group of people and building a company.

For more, read: 7 Survival Tips For Startup CEOs

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