• Omer Winrauke

What No One Tells You About the First 200 Days of Startup Life

Updated: Jul 30, 2020

Last May, I decided to take the leap and pursue my dreams of founding a company with my classmates at Cornell Tech. It’s been a crazy few months and there’s a lot that I learned along the way that I realized no one really prepares you for. So I decided to write them down for anyone thinking about taking the leap:

1) Embrace the emotional roller coaster

There will be days that you feel on top of the world, days where you feel like you are at rock bottom and days where you are constantly fluctuating between both. While it is important to celebrate the wins and learn from experiences that are not, it is also important to learn how to manage your emotions so that no matter what happens that day, you can continue progressing towards your goals.

2) Learn how to process constant criticism

The first thing anyone will do when you tell them about your product is say, “But what about…” or “Have you thought about…” I don’t know why the human brain works like this but they will inevitably try to think of holes in your product or suggest what they think will be the next big feature. Learn how to listen to these thoughts, extract what you need and file away the rest.

3) Your team is everything

Startup life is not a solo sport and it will absolutely be a roller coaster. No one is going to understand your bad days or celebrate your wins like your team will. And no matter how close you and your founders are, you will get into arguments. So, it is important to find a team that is not only talented but will stick around during the tough times, support each other and work it out. I would not have made it through 200 days and Pilota would not have made the progress that we have without our entire team.

3) Your team is everything

Whether you are speaking to an investor or pitching to a client, you will walk in with a game plan but you need to make sure you don’t just walk in and execute this game plan. Take the time to read the room and understand the person or company’s situation and motivations. Mentally adapt your game plan accordingly to make sure you are hitting the right notes and connecting with your audience.

5) Check your ego at the door

Being a successful startup founder will require you to find support in others, whether it is from other founders, investors or startup communities. What I have learned in these 200 days, is that no one loves to tell you about their successes like startup founders but also no one will help you like they will. So you need to be someone who will engage in their stories, compliment their successes and have the humility to ask them for help.

6) Don’t be afraid to ask for help

It can be easy to feel like you and your team are alone on this journey but this is not the case. There is support all around you, whether it is in the form of your co-founders, other startup communities, mentors or even your friends and family. If you get stuck, there are so many places to ask for help, so instead of wasting time being stuck, go ask for it!

7) Every second is valuable

If you look for them, opportunities will begin to present themselves to you. It is important not to get distracted by these opportunities and make sure that the ones that you engage in are ones that will be worth your time, money and effort down the line.

8) Get organized

When you first start out, you are going to start using Notes, Excel Sheets and random Google Docs to keep track of things. But as you quickly start to make progress, these easy solutions actually end up getting very messy and take up more of your time. Establish some practices for you and your team: where important documents get saved, where meeting notes go, etc. so that you can spend more time making progress and less time looking for those notes from three Mondays ago.

The bottom line: The first 200 days are going to be simultaneously exciting and terrifying. Embrace the uncertainty!

Check out my startup Pilota! We use AI to predict flight disruptions ahead of time and proactively book travelers a back up flight for free during disruptions!


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