Investors turn founders into insecure little teenagers

Many founders lose confidence when they meet with investors. On the quest for validation, their entrepreneurial courage goes right out the window.

Founders often believe that investors have all the power, so they accept bad advice and make promises they can’t keep. But when external forces are the key to a company’s success, that’s a red flag.

Here’s a simple piece of advice:

Stop worrying about whether investors like you. Instead, decide whether you like investors.

Want to rebuild your confidence? Reclaim some of your power. Investors don’t guarantee success—you do. It’s your responsibility to explore balanced, mutual relationships with investors, and you can’t do that if you’re always worried about impressing them.

Want more actionable advice on getting founders to back your startup? Download our free guide Fundraising Hacks For Founders.

When you meet with investors, you need to...

Understand your goal

You’re meeting to explore the potential for a partnership—you’re not there to convince anyone to invest. Leave your powers of persuasion at the door. This isn’t the time to sell yourself or your company. In fact, don’t sell anything at all. Just ask yourself, “Is there a mutual fit?”

Speak honestly. See if you like each other. You’re simply there to evaluate whether another conversation should take place.

Be yourself

When founders try to impress investors, the opposite tends to happen. Most good investors can see right through your bullshit, so show them the real you. If you’re nervous, that’s fine—own it and move on. It’s also okay to acknowledge your weaknesses, as long as you have a plan to address them in the future. Be confident that you have a solution, even if the solution hasn’t been implemented yet.

Want to know what happens when you’re not genuine?

  • You lose the investors who are right for you
  • You attract the investors who are wrong for you

And besides, you’ll never be the right investment for every VC firm. That’s just how things go. What matters is that you find the right investor for you.

Ask questions

Investor meetings shouldn’t be one-sided conversations. If you answer all of their questions, you don’t win a prize.

Here are a few questions you should ask early on:

  • If we ever run into a problem, how would you interact with us?
  • What should we expect from you if we’re not hitting our numbers or the market shifts? What do you expect from us?
  • Which of your investments are you most proud of and why?
  • If you were in our shoes, what other questions would you have about this partnership?

When investors make suggestions or provide advice, don’t forget to ask follow-up questions. For example, if they say something like, “We think you need AI in this software,” ask, “What do you mean when you say AI? Why do you think it’s a good idea?” Make sure you have as much context as you need to respond with confidence and clarity.

Listen carefully to their answers. Pay attention to how they respond to your questions. What does your gut tell you? Are they being genuine or are they just telling you what they think you want to hear?

Gather as much information as you can. You don’t want to make a decision without knowing everything you can about how investors operate and what their expectations are.

Push back

You’re the only one who can help investors understand your business, so don’t be afraid to push back. When someone makes a suggestion, there’s nothing wrong with saying, “I don’t think we should do that for these reasons,” or “We thought of that, but there are some considerations that could prevent us from pursuing this option.”

You’re not being rude or ungrateful—you’re just offering your perspective, which has tons of value since you know your company better than they do.

Be a founder who can push back and be open-minded. Be a founder who looks for feedback and advice, but who can make the company successful with or without investors.

When investors yell, “Jump!” you don’t have to say, “How high?” Just because they send an email doesn’t mean you have to reply right away, especially if you’re working on something more pressing.

Pushing back, when appropriate, allows investors to interact with the real you. For example, in my early days as an entrepreneur, I received an email from a potential investor that read like this:

Hi Steli,

I’m writing to you from X COMPANY, 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 HUGE STARTUPS RUN BY YOUR ENTREPRENEURIAL HEROES.

Travis Goodman (who is a founding partner at the firm) was impressed by YOUR LITTLE COMPANY and asked me to find out more about you and your financing plans.

Can you make time for a brief call in the next couple of days? When would be good for you?

– Stacey

Sounds cool, right? But if you’ve interacted with investors in the past, you know they probably just wanted to schedule a call with a junior associate, who would ask a million questions and have zero decision-making power. Nothing against junior associates but, even back then, I wasn’t in the mood for that conversation. So I said:

Thanks for reaching out, Stacy. I’d be happy to jump on a quick call with Travis sometime this week. Best would be Thursday or Friday.

She replied:

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

Nope. So I wrote:

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 responded:

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 meet with Travis.

Totally reasonable, but that didn’t work for me. So I said:

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

She made another attempt to convince me to speak with the associate first, but I didn’t respond. Finally, a few days later, Travis, the senior partner, sent 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!


When you understand that investor meetings are two-way streets, you’ll feel much less anxiety about them. If they can’t meet you halfway, if they’re unable to see things through your eyes, if they get hurt when you push back, they’re probably not the right investors for you anyway.

Investors are people, not gods

You need to dispel the myth that investors can make or break your company. They’re humans. They have pressures, commitments, rationales, and biases just like the rest of us. Their goal is to make money—they have quotas and goals, too.

Ultimately, investors are bankers. They provide cash so that you can run your business more effectively. They expect, if nothing else, a return on their investment. The relationship is fundamentally transactional. Investors aren’t magicians and they can’t guarantee your success—so it's important that you've already considered alternative funding options (like bank loans, securing a high-limit business credit card, a loan from friends and family, or otherwise) if having investors on board for the long-haul doesn't sound like your best call.

Success is your responsibility

Investors can accelerate growth, but they’re not the driving force behind it. If you decide that an investor makes sense for you, and you can work together to make your company stronger, go ahead and pursue that partnership. But it’s primarily on you to evaluate their value, not the other way around. The success of your company doesn’t depend on anyone else.

Want to get our best tips on getting the right investors to back your startup? Download our free guide!

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