365 Days Later: Lessons At An Early Stage Startup


                                            Aerial view of downtown Chicago at night.

A little over a year ago, I moved to Boston for the summer to attend a new program, then called Boston Startup School, now known as Startup Institute. Motivated to learn more about the startup community and gain a valuable skill set to prepare me for a career in tech, I took a leap of faith and never looked back.

Fast forward one year.


In the past twelve months, I transitioned from student to alum to employee. I have met hundreds of companies, worn about a dozen hats, held four job titles, lived in three cities. Throughout the process, I had a front row seat in watching the program that I once attended change the lives of countless people.

As I reflect, I am reminded of a blog post posted exactly a year ago, in which I wrote about why I decided to join Startup Institute as an employee. In it I confessed…

“I am a total nerd. I love to learn. I strive to be challenged. I like it when my brain hurts. I am, what some may call, a perpetual student.”

Well, I can tell you that my brain certainly hurts. The past 365 days have presented me with some of the most challenging and exciting experiences I can think of, and what’s more, it’s been a ton of fun! To keep with the theme, here’s a few things that I have learned so far from being an employee at an early stage startup:

  • Do not ask for permission, beg for forgiveness - Productivity is a necessity on a small team. Successful startup employees are growth-minded. They are able to identify problems that have not even occurred yet,. Understand the next steps that need to be taken and push forward to drive action.
  • Does it make you nervous? – If yes, then do it! If you are uncomfortable doing something because it is challenging to you intellectually, you are doing something right. Strive to be surrounded by people who are smarter than you every single day.
  • Failure is OK- Entrepreneurs are not afraid of failure. They stare it in the face everyday and defy the odds. So, if you have failed then it means that you have learned. If you fail, own it. Learn from it. Move on and do not repeat the same mistakes.

One year later, as I sit in the Chicago office, I am as humbled by where Startup Institute has been and where we are headed. I am excited to be a part of this team, this community, and to continually be given more responsibility than I probably should.

As I head into year two at Startup Institute, I continue to seek opportunities to be challenged and nerd out. Cheers to a whirlwind first year and to our new campus in the Windy City.

Give Kailey a shoutout on Twitter @kaileyraymond. Interested in Startup Institute Chicago? Check us out. #SIC