Startup Institute: The Freshmen Chronicles

John Egan
11 min readJul 11, 2016

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The adventures and highlights of my journey in the Startup Institute Chicago 8-week program (Week 1–2). The first blog in a 4-part series.

Preface: Snoopy and I Are A Lot Alike

The world’s most talent beagle once sought out a new career as a writer. With little to no experience, Snoopy brought up his typewriter on his big red doghouse and began writing. Scared, unsure, and hesitant, he began a new career path in spite of skeptics.

Recently I decided to leave good, stable career path to set towards the technology and startup industry to start a new career as an aspiring tech rockstar. Scared, unsure, and hesitant, I applied and was accepted into the Startup Institute in Chicago to help gain the knowledge, skills, and close network of companions that I one needs to break through in this industry.

Inspired by Snoopy, here begins my blog of my experience going through the Startup Institute 8-week immersive tech program.

Now the world famous author, Snoopy, always begins his novels with the phrase “It was a dark and stormy night…”.

I’ll need luck writing a blog for the first time too.

I won’t be like him trying to write the world’s greatest novel, but I will be breaking my overall experience into four parts. During the first week, we were told that the SI path is just like school all over again. You go through your freshmen year (Week 1–2), sophomore year (Week 3–4), junior year (Week 5–6), and senior year (Week 7–8). Sounds like a pretty good way to write up my journey by, tell stories, and provide great advice (at the end of this blog I posted a list of recommended books and resources from several key individuals). And because the Peanuts comic is my favorite, I’ll be including comics along the way.

Chapter 1: FRESHMEN YEAR

It was a dark and stormy night….

Leaving my previous job and informing family friends I plan on going back to ‘school’ was a weird and confusing discussion. It was one of those conversations when you knew you are 100% sure about this, but it’s so hard to explain it to another person that doesn’t quite understand the big picture and what I want to do.

Similar talks I have when telling people I’m going back to a ‘school’
Joining Startup Institute is a great idea!

After going through all the benefits that the Startup Institute provides, why I want this, and more, I think it finally made sensed to them. Or at least they said that just to change the conversation. Who knows! But the main thing is, I’m 100% positive about this big move.

Leading up to Day 1, I felt like a nervous freshman all over again. Doing my pre-homework, researching logistics of my days, and just dealing with the feeling that you don’t know what you will be doing during the next eight weeks (that drove me crazy).

The ‘first day of school’ feeling still applies as an adult.

Day 1 comes and getting to the location was a big puzzle in itself. The Startup Institute has the proud pleasure to have a dedicated room in the Chicago famed tech incubator 1871 in the Merchandise Mart. Took me 10 minutes just to find 1871 office space. The Merch Mart is massive.

The big, scary, castle that is the Merchandise Mart.

9:30 AM came around and it didn’t take long getting to know my classmates (the other brave souls) as we started off with what has to be the ultimate icebreaker —

“What do you suck at?”

It’s a question you don’t often ever ask yourself and here we were about to share with everyone what we are self-conscious about. It turned out that many things that we individually suck at, many others suck at it as well. It created a very honest and open environment from the start that helped each of us shared our past and focus on the future together as a group of friends.

Meet our friendly and fun cohort! We’re a bunch of (smart) weirdos.

Throughout the Week 1 and Week 2, we crammed our brains with new knowledge, technical skills, career advice, and so much more. Here are some of the highlights…

Brent Williams from Clique Studios came in talk to introduce us about EQ and IQ. I’m sure a lot of people heard about IQ (intelligence quotient), but I bet most people know don’t about EQ (emotional intelligence quotient). It’s a vital trait many don’t think about when acting out.

There are 4 pillars of EQ;

  1. Self-Awareness
  2. Self-Regulation
  3. Empathy/Social skills
  4. Relationship Management

He also mentioned a few things to worry about in your first 30 days of a new job;

  1. Your knowledge and methods are completely different.
  2. Learning the company culture.
  3. You will be a slow-learner.
Ayesha Curry’s freak out during the NBA finals was an emotional time for her

We were then introduced to a very special guest, recent winner ‘CEO of the Year’ from of Moxie Awards (One of Chicago’s tech award ceremonies by BuiltIn Chicago) CEO of the year Amanda Lannert from Jellyvision.

Hello, it’s Amanda Lannert. I am glad after all these years we met.

Her mantra in life and for her company is “Be Helpful”. They are simple words and it’s a simple mission for Jellyvision and their culture proves this. Consistently ranked as one of the best places to work in Chicago, Jellyvision’s culture is gaining an infamous fan base in the Chicago tech community.

She passionately spoke about 5 core values she believes in for company culture;

  1. Don’t hire slowly, hire thoughtfully and deliberately.
  2. Part ways quickly, with transparency, generosity, and with compassion.
  3. Stick to your values even when it gets harder (and it does get harder).
  4. Embrace new rituals.
  5. Lead by example vs. with policy.

“The people closest to any problems, have the best solutions.”

A story about Captain Michael Abrashoff (see ‘It’s Your Ship’ book in the resources), her core values and just her enthusiasm made her presentation a remarkable one for our class.

“You get what you give.” — Amanda Lannert

Didn’t know Amanda was a New Radicals fan (who isn’t though, 90’s music is the best), but she’s suggesting that if you put in hard work, you’ll reap life’s rewards. Science proves this that it’ll better your life. This type of mentality on Day 1 is a thought I’ll be repeating every day as I go through this program and throughout my new career. Think I found my new daily morning wake-up jam — Thanks Amanda!

Snoopy would agree with Amanda’s mantra.

Rick Desai from Dashfire and Listen, followed up Amanda with a presentation on ‘How to Introduce Yourself’.

Two main points when it comes to introducing yourself; 1) You have to get over your fear and 2) It’s all about impressions.

“Develop your voice and then build your brand.”

Going through this program, how to introduce yourself while we begin networking to many individuals is VERY IMPORTANT and one we will often be practicing.

Personal Image 101 from Rick Desai

Fred Hoch from the ITA came in and welcomed us to the exciting Chicago Tech community. It was great to be well received by one of the key leaders of the city. The ITA is doing the most when is comes to measuring the tech impact.

He mentioned a story that blew my mind. He talked about how recently a few Chicago companies went to New York’s Techweek and during the week-long event hardly any one heard of some of the top / great tech companies here in Chicago. Considering how prominent Chicago is, that amazed me. It’s time our city break into the tech bubble that is Silicon Valley and New York. Chicago is coming.

We soon went over on what crafting our career theme means to each of us lead by Kailey Raymond from Hired.com. It was a time to have deep thoughts on who we are and what are goals are in life and our career’s.

“A job is a way to make money. A career is something you dedicate your life to. ”

“Find something or a moment where you reach flow.

Each of us spent a few minutes to think about four moments in our career when we reached ‘flow’ and moments that are cherished. Then we were to identify each of them by a list of career themes. Below is a summary of the cohort’s career moments.

Our cherished career moments with career themes

Now I did not write down all of the career themes, so some of these abbreviations I can’t currently recall. But what impressed me the most from this exercise is that out of the entire cohort’s 68 (4*17 = 68) cherished career moments only one of those moments were money related. That made me so happy to see that our group admires helping others and improving our inner self over the money we made. We have a good group of people here.

A few slides here from RJ Pahura with Venture Connects and one key quote when it comes to raising money from investors.

“You only get one shot when you go out to investors. Make it count.”

Top 20 reasons startups fail
Not even 20% of pitches get funded!!!

Then Martin McGovern from IdeaLemon, one of our staff leaders, went into more detail about Chicago’s prospecting startup ecosystem. Chicago currently #7 in the world for startups, and we’re moving up and up this list each new year.

We’re coming for you Silicon Valley.

Speaking of startup ecosystem, there’s a new best city in America for startups ;)

Packed into our tight schedules, we had chances to relax and have friendly fire-side chats with successful individuals in the industry. These might be some of my favorite times because we get to relax, interview smart mentors, and hear honest opinions.

David Gardner, CEO of Colorjar shared his story about how being an entrepreneur is a lot like being an athlete (David is a former pro basketball player). He is defined by working hard and hustling to achieve your goals. There are no shortcuts to success.

“There’s never a perfect time to start something. The most important part is starting.”

“Company names that involve an image is typically better. They’re easier to picture and easier to remember. i.e., Blue Bottle, Colorjar”

“Start small and build it up. You’ll learn more.”

Starting and running a company is a lot like driving your car at night in the middle of nowhere. You’re driving your car in the pitch dark, and your headlights only shine 20 feet ahead of you. You don’t see what’s ahead of you, but you always must be ready for anything that might jump in front of you. You need a good car to handle the unpredictable.

David Gardner, CEO of Colorjar
An easy going conversation with Chris Campbell, CEO of Review Trackers

To finish off the freshmen year, Howard Tullman CEO and godfather of 1871, ended Week 2 and blew our minds with an incredible presentation on the startup industry and being an entrepreneur. If you EVER have the chance to see Mr. Tullman present, make it a must go-to event. We walked away with tons of wisdom within this hour-long presentation. I can’t wait to see him speak and chat with him more often.

Howard’s definition of success

My Technical Track

In the Startup Institute, there are 4 unique technical tracks that a student can choose to pursue; Web Design, Web Development, Sales and Account Management, and Marketing. I am in the Web Design track with the aspirations to be a Product Manager, Front-End Developer, and Product Designer.

Between meeting these great people and hearing these presentations, one of the main focuses of the Startup Institute is to improve your technical skills. You can go to the Startup Institute website to learn more about the individual tracks and curriculum, but let me just say that WOW I’m learning a lot and will be coding away on my computer non-stop for the next eight weeks and beyond. Also, the instructors teaching us these lessons are real professionals in the working world with cool jobs and much expertise. They’re awesome :)

A few classmates were saying the first week felt like a month, since every minute of the eight-hour day we had a scheduled activity. Maybe it’s the radical change of being “busy” every minute of the day (I hate the word ‘busy’ BTW but that’s a blog for another day), but soon I guarantee we will all reach a state of ‘FLOW’ during this program with finding our career theme, perfecting our technical skills and conversations, and much more.

Time to accomplish big things today, to achieve great things tomorrow.

Follow us along on Twitter #SIChicago as my fun cohort and I tackle on this experience! Follow me on Twitter at @John_M_Egan as well. I post cool things (I think).

Bring on Sophomore year!

RECOMMENDED BOOKS AND RESOURCES FROM WEEKS 1–2 :

Startup Institute Staff //

Brent Williams (Clique) //

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