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It’s strange how entrepreneurs who are large risk takers and bold personalities turn into insecure little teenagers when facing investors.

“Do they like me? Do they think I’m fat? Oh god, they think I’m stupid and my idea will fail. I WILL NEVER SUCCEED IN MY LIFE!”

Ok, this might be pushing it, but you get the point. Investors are the one group of people entrepreneurs are dying to get validation from. You desperately want every investor to love you and your startup, but you can’t emotionally deal with the outcome when they don’t.

That’s the problem. When you enter any relationship with a desperate desire for love and validation, you usually won’t get it. It’s a pretty unattractive attitude. Investors can smell desperation and often make the emotional conclusion that you’re probably a bad bet (they call it “pattern recognition”).

And sometimes, investors take advantage of entrepreneurs who are dying to be just like Zuckerberg or Jobs.

Entrepreneurs spend hours and hours reading the latest news and gossip about the coolest new startup, the most badass founders, and the most powerful investors. They daydream about how it would feel like to be one of the “cool kids” but deep down are afraid that they may never be good enough.

It’s a shame. We’re talking about entrepreneurs here. People who didn’t listen to their families and friends when they quit school or their well-respected job to go and pursue their dreams. People who by definition have to be unreasonable. Movers and shakers.

But when it comes to investors, most of them lose their edge.

And the worst thing is that it’s that kind of emotional insecurity that turns investors off. It makes them feel like you’re weak and don’t have what it takes.

Investors, too, daydream about finding the next Zuckerberg and look at you to see if you “act” just like the “cool kids.”

You know what they say – if you look like a Zuck, swim like a Zuck, and quack like a Zuck, you have to be a Zuck!

Let’s stop all this nonsense. Step back and relax. Adjust your point of view. When you talk to investors, ask yourself, do you like them?

Case in point, two days after I wrote a similar post about working with investors on my blog, I received an email from a potential investor that read something like this:

Hi Steli,
I’m writing to you from BIG MONEY Capital, an early-stage venture capital fund based in San Francisco with offices around the world. You might know some of our portfolio companies, which include THE BIGGEST STARTUPS RUN BY THE ENTREPRENEURS YOU LOOK UP TO.

Travis Goodman (who is a founding partner at the firm), was impressed by YOUR DARLING COMPANY and asked me to find out more about the team behind it and the company’s financing plans.

Could I ask you to make time for a brief call in the next couple of days? When would be good for you?

– Stacey

Sounds awesome, right? But, if you’re experienced in interacting with investors, you’ll know that this probably means they want to schedule a call with a junior associate, who will ask a million questions about my business and learn as much as possible without having any decision making power when it comes to actually investing.

That’s how VC firms work. Lots of associates do the groundwork and a few partners actually make the decisions. Nothing against associates, but I want to talk to the decision makers.So I say:

Thanks for the kind words and for reaching out.
I’d be happy to jump on a quick call with Travis sometime next week. Best would be Thu or Fri.

She responds:

Many thanks for getting back to me. I would like to schedule a call with Justin, one of our team members working closely together with Travis. Would that work for you?

Yeah that’s what I thought. Nope – not really interested in that.

So I write:

I hear you – but I’d love to talk to Travis, let me know when he’s free and we’ll schedule a call.

To which she responds:

Understood. Unfortunately, Travis’ schedule is pretty dense so we always gather some data points first. Should that go well, we would certainly appreciate it if you could do a meeting with Travis.

Yeah that sounds totally reasonable but doesn’t work for me.

My response:

I’m happy to jump on a quick call with Travis. I’m cool postponing a discussion until he has time.

She makes another attempt at convincing me to do a call with the associate first but I don’t respond.

Finally, a few days later, Travis, the senior partner, sends me an email:

Steli –

Looks like you are following your own advice!  :) Just read your blog post about not being intimidated by investors.

My assistant is copied on this email, coordinate a time for us to talk ASAP!


In my early entrepreneurial days I would never have had the guts to say no to any request by a VC firm. But then again, in my early entrepreneurial days I wasn’t successfully raising money!

So stop worrying about whether investors like you and if you’re worthy of their love and attention. Think about whether they’re people you really want to work with. Can they talk about your space intelligently? Do they have value-add? Would you like to go on another “date” to learn more and see if this is a relationship with a future worth investing in?

Simply be yourself and be confident. Because confidence not only makes you more attractive to the opposite/same sex but also works wonders on investors.

Steli is a high school dropout, self-taught entrepreneur, anonymous learning addict, and owner of a one-way ticket that took him from Europe to San Francisco where he founded Supercool School, VibaTV, and SwipeGood. As an alumni of Y Combinator, Steli recently launched Elastic, Inc., offering sales-as-a-service to other startups here in Silicon Valley and throughout the U.S.

[Top image credit:  Ariwasabi/Shutterstock]

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