A Short Course on Scaling as a Startup CEO

By David Frankel, Managing Partner

Working with a board of directors is one of the key challenges facing founders. While tech has an egalitarian mien, there are material power imbalances and they can cause tremendous stress for founders. Some thoughts on how to manage those concerns:

👏 Your investors want you to succeed

There’s a belief that VCs are keen to replace founders at the first misstep. Nothing could be further from the truth. The reality is that you are more likely to be replaced if your startup *succeeds* than if it struggles.

At the early stage, investors know that firing a CEO is likely to kill the company. Practically speaking, it’s also very hard to find talented outside CEOs who are keen to take over an unprofitable business with an uncertain future.

The thing to fear more at the early stage is that those of your investors who are expected to invest at each stage will choose not to invest *at all* in the next stage. This signal is damaging and potentially fatal. Fear this way more than a pink slip.

🏆 Your VCs expect you to level up

Part of being a CEO is getting comfortable on the expectations treadmill. You have signed up to be a peer to Mary Barra, Jeff Bezos, and Sundar Pichai If you want to compete, you must scale the learning curve. Rapidly.

You are going to make mistakes. Your investors know this and expect it. The important thing is not to make the same mistakes repeatedly, and critically, to recognize and fix those mistakes. Your reaction to a mistake is often viewed more critically than the mistake itself.

Fair or not, you are going to be compared to the highest performing CEO in each VC’s portfolio. That’s a lot of pressure. Take heart, every great CEO you now look up to was once in your shoes. It is doable.

🤬 Don’t overreact to criticism

You’ll likely get a lot of feedback from your VCs, and at times, it will feel harsh. Your investor may get frustrated with you. This can be worrying, but it’s also (sometimes confusingly) a sign that they care and believe in you.

It’s not a perfect analogy at all, but the relationship between a startup CEO and VC is like that of Olympic-class athletes and their coaches. It’s punishing, it may even feel adversarial at moments, but it’s ideally in the name of pursuing excellence together.

Most founders were high-performers in previous roles and unaccustomed to the incredibly high expectations of being a CEO. Learning to be a CEO is a job unto itself. I’ve gathered some tips on how to build the necessary skills in this post:

There is no other space, in my experience, where career acceleration happens as quickly as in startups. In closing, when choosing a VC, make an effort to find partners who have a demonstrated track record of helping CEOs develop and fulfill their potential.




Our mission is to be the most aligned VC for founders at seed. #ProudInvestor in @Uber @TheTradeDeskinc @Buzzfeed @Cruise @Diaandco @PillPack @SeatGeek & more.

Love podcasts or audiobooks? Learn on the go with our new app.

Recommended from Medium

The untold horror stories of hiring remote developers

When do you #startup?

The Surprising Way Your Professional Network Might Be Making It Harder to Fundraise

Indoor air quality startup Clairify successfully closes seed funding

Six things I’ve learned in sales as a newbie

Estimated arrival time in Shibuya w/Startup Visa 🛬

Hiring for Your Startup Doesn’t Have to Be as Hard as You Think

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Founder Collective

Founder Collective

Our mission is to be the most aligned VC for founders at seed. #ProudInvestor in @Uber @TheTradeDeskinc @Buzzfeed @Cruise @Diaandco @PillPack @SeatGeek & more.

More from Medium

YC Application Tips from a First-Time Applicant Who “Barely” Made It (S21)

Startup Confessionals: Combat the Awkward Convos around Vesting

Building a startup at the end of the world

Building Startups in a Bear Market 🐻