The Freshman Chronicles: Highlights From My Journey at Startup Institute Chicago

This article by John Egan first appeared on Medium.

Preface: Snoopy and I Are A Lot Alike.

The world’s most talented beagle once sought out a new career as a writer. With little to no experience, Snoopy brought his typewriter up 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 Startup Institute in Chicago to gain the knowledge, skills, and close network of companions that one needs to break into this industry.

Inspired by Snoopy, here begins my blog of experiences going through the Startup Institute program. As 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 try to write the world’s greatest novel like Snoopy, but I will be breaking my overall experience into four parts. The Startup Institute path is just like school all over again. You go through your freshmen year (weeks 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 my journey, tell stories, and provide great advice (at the end of this blog I share 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.


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 were 100% sure, but it’s so hard to explain it to another person who doesn’t quite understand the big picture and what you want to do.

Joining Startup Institute is a great idea!

After considering all the benefits that Startup Institute provides, why I want this, and more, I think it finally made sensed to them. Or, at least they said that it did 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 day-to-day logistics, and just dealing with the feeling that I didn't know what I'd be doing during the next eight weeks (that drove me crazy).

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

Day 1 came and getting to the location was a big puzzle in itself. Startup Institute has the proud pleasure of having a dedicated room in the Chicago famed tech incubator 1871, in the Merchandise Mart. Took me 10 minutes just to find the 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 are you bad at?

It’s a question you don’t often ever ask yourself and here we were asked to share with everyone what we are self-conscious about. It turned out that many of the things that we individually suck at, many others are bad at as well. It created a very honest and open environment from the start that helped each of us share 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 have 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 four pillars of EQ:

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

He also mentioned a few things to consider in your first 30 days of a new job:

  1. Your knowledge and methods are completely different from your coworkers' in this new role
  2. You'll have to learn 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 of CEO of the Year from of Moxie Awards (Chicago tech award ceremony by BuiltIn Chicago) Amanda Lannert from Jellyvision.

Amanda's mantra in life and for her company is “be helpful.” These are simple words, but 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 five 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 hard (and it does get hard)
  4. Embrace new rituals
  5. Lead by example vs with policy

Amanda's core values and just her enthusiasm made her presentation a remarkable one for our class.

You get what you give. — Amanda Lannert

[bctt tweet="You get what you give, says @AmandaLannert via @John_M_Egan" username="StartupInst"]

I didn’t know Amanda was a New Radicals fan (who isn’t though? 90s music is the best), but she’s suggesting that if you put in hard work, you’ll reap life’s rewards. Science proves that this will better your life. This type of mentality on Day 1 is a thought I’ll be repeating every day as I go both through this program and through my new career. I 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 Amanda with a presentation on How to Introduce Yourself.

Two main points come up when 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. —Rick Desai

[bctt tweet="Develop your voice and then build your brand. It's all about impressions, says @rickdesai" username="StartupInst"]

Going through this program, how we introduce ourselves when networking will be very important, and something 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 impact of tech in Chicago.

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 anyone heard of great tech companies here in Chicago. Considering how prominent Chicago is, that amazed me. It’s time our city breaks into the tech bubble that is Silicon Valley and New York. Chicago is coming.[bctt tweet="It's time our city's on the map for great #tech. Chicago is coming, says @John_M_Egan" username="StartupInst"]

We soon went over crafting our career theme, led by Kailey Raymond from It was a time to think deeply about who we are and what our goals are in life and our careers. As Kailey said, "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. —Kailey Raymond

Each of us spent a few minutes thinking 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 grouped by 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 most from this exercise is that out of the entire cohort’s total of 68 cherished career moments, only one of those moments was money-related. It made me so happy to see that our group admires helping others and improving our inner-selves over the money we make. We have a good group of people here.

A few slides here from RJ Pahura with Venture Connects and one key quote about raising money from investors.

You only get one shot when you go out to investors. Make it count. —RJ Pahura

[bctt tweet="You only get one shot when you go out to investors. Make it count. — @rjpahura via @John_M_Egan" username="StartupInst"]

The top 20 reasons startups fail.
Not even 20% of pitches get funded!

Then, Martin McGovern from Startup Institute and IdeaLemon—one of our staff leaders—went into more detail about Chicago’s prospecting startup ecosystem. Chicago is 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 ecosystems, there’s a new best city in America for startups ;)

Packed into our tight schedules, we had chances to relax and have friendly fireside 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 goals. There are no shortcuts to success. Some wisdom from David:

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 of1871ended 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: Web Design Courses

In Startup Institute, there are four 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 Startup Institute is to improve your technical skills. You can visit 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, between finding our career themes, 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 this experience. Follow me on Twitter at @John_M_Egan as well. I post cool things (I think).

Bring on Sophomore year!