Startup Institute: The Sophomore Chronicles

Photo from Startup Institute’s Open Doors Party by Sean Su, on behalf of CloudSpotter (& Snoopy)

The adventures and highlights of my journey in the Startup Institute Chicago 8-week program (Week 3–4). The second blog in a 4-part series. (Click here to read about Week 1–2: “The Freshmen Chronicles”.)

Chapter 2: Sophomore Year— “Flying High”

By Week 3, we began calling the Merchandise Mart are second home.

Throughout Week 3 and Week 4, we started flying high and accelerating our learning at a much faster pace. We began to build our network, we got into the heart of our technical tracks, and we had deep talks to discover who we are and what we want to make out of our lives.

Like the typical college years, as freshmen we were introduced to the campus and learn all the general education type classes. Now as sophomores, we began hitting the books hard to start building our technical skills and began putting words and lessons to action.

We couldn’t have been more excited.

Let’s jump right into it!

The Startup Institute has a well known and respected reputation in the tech industry, and the company has had the privilege to established partnerships with many start-ups to assist with the program. In Week 3 we had the opportunity to meet a few of these companies at our Partner Fair. We had such companies as Growit!, Syndio, Topstep Trader, ITA, Schlep, and Narrative Science come in to meet.

It was a time for us to be introduced to several cool companies in the city and hear about each of their products, their company culture, and much more.

As we were networking with these companies, ‘communication’ was a word that was frequently mentioned. As companies grow, it’s important to hire smart and properly managed the growth right, or else you can lose touch with employees.

In a group, the possible communication connections between individuals for verbal or written communication are called communication channels. Two people talking to each other have only one channel for back and forth information sharing. Add a third person and now you have three possible channels, and incomplete communications can begin.

It’s common sense that the larger teams become, the more communication’s become a challenge. But do you know the numbers behind it?

The communication channels formula is a way to express this “challenge” numerically. Using ’N’ as the number of team participants, you can calculate the total number of communication paths on a team.

The communication channels formula. N = number of persons

4 people = 6 total channels, 5 people = 10 channels, 6 people = 15, 7 people = 21, 8 people = 28 channels, 9 people = 36, 10 people = 45 channels.

If you double the size of your project team from 5 to 10 people, the number of communication channels increases 4.5 times from 10 to 45. Another way of stating it and in reality what it means is that a manager needs to theoretically spend four and a half times the effort to ensure the project team of twice the size keeps informed.

All those channels can be difficult to monitor if not done right. Especially for a project manager!

This formula expresses that the number of people on the project is at the heart of what makes communications a challenge. It’s not the size of the budget or the technical complexity that poses our greatest communications challenge. It is the number of people with whom we need to communicate about our budget and technology that makes it harder, the more people we involve.

The formula also acknowledges, that it is not only the project manager who has to communicate. The formula takes into account that on a 5 people team it is not only the manager who is communicating with 4 others, but it’s everyone talking to everyone. The number of people who are constantly communicating with each other is much larger than that.

It’s no wonder that organizations have difficulty getting everyone on the same page and working effectively. Clearly, a plan is necessary to control the flow of information and make sure that everyone receives the information they need to do their job.

The right product. Done right. Managed right. Those are the pillars of a great software product.

Sam Harris, Founder / CTO of task management software Tribe, came in to present to us how to manage right and provided an overview of the vast number of company management methods and how to use all of the techniques in what he refers to it as “Gumbo Methodology”. Gumbo is industry agnostic and is designed to be flexible to different project needs by pulling pragmatic best practices from agile, waterfall, and lean management philosophies.

Sam comes from a military background and has been a manager at a variety of companies in Education, Finance, Consulting, Defense, and Technology. He knows a thing or two about launching products and managing teams. He gets stuff done and he gets it done fast.

Now launching his new Tribe product, he has taken his management experience and technical skills and created a new management software to organize one’s tasks, projects, and goals. I’ve been a user of practically every type of management product out there (I love to experiment and try every product in the market) and in my eyes Tribe is a game changer. If you haven’t heard of it, I’ll suggest you check it out and instantly notice the difference. I’ve been using it a great deal since being introduced and has helped myself manage the craziness of the number of items I seek to accomplish during my time here at the SI program.

Different types of project management methods
There are so many roles in a company that all need to be working effectively at the same time.
Big Picture Philosophies to always be considerate of.

Through the help from a few of our partner companies, we were going to have the chance to perform mock interviews with recruiters to nail down our interview techniques, but before we practiced we had Betsy McCann, Head of People Operations from Valkyrie Trading come in to give us an intro to interviews.

Betsy went over with us the common logistics of the interview process, small things like asking for water, where to sit, what to wear. Stuff we commonly don’t think about.

Another topic we discussed, one that hit me hard, is the fact that job interviews are weird. They are flawed, they are not normal, and they make no sense.

“What is your greatest weakness?”
“Why should I hire you?”
“Describe yourself in three words.”
What’s your favorite color and why?”
“Would you rather fight 1 horse-sized duck, or 100 duck-sized horses?"

Who asks these type of questions in normal life??? No one.

Let me ask these types of questions the next time I go out on a date and see how that works out. I may get banned from Tinder for asking questions like this.

Similar to every interview question you will ever get asked.

As Soren Kierkegaard, famed philosopher said many years ago -

“Life can only be understood backwards, but it must be lived forwards.”

Questions like these are asked because it’s the only way to understand a person, but will it predict an employee’s future success? Who knows.

It’s a hard truth that this is how every job search is handled, by reviewing one’s past to attempt to get a grasp on who a person is, but it’s hard because interviews are terrible predictors of job performance. Many technical skills, team skills, intelligence (I.Q. & E.Q.), attitude, and more can’t be measured accurately during an interview. Here’s a list of 50 of the most common interview problems.

Interviews should focus on the value a person can add in the future, not their past.

Unfortunately, there is no sure-fire right answer to solve this weird, flawed problem. It is important that you are at least aware of the things because it can ultimately impact the results of your interview. One of the most common traits that can affect your interview success is being nervous and not confident as you present yourself.

Of course, getting nervous before any big moment in life is natural. We’re all human after all. The best piece of advice I can offer for a job interview is to relax, be honest, and be yourself. It’s just a conversation. If anything, make it a fun conversation.

Interviews can be the one curve ball in a person’s (the interviewer’s) day. Make it fun curve ball that leaves the person in awe and wanting to learn how you did that.
“Your interviewer is also hiring a coworker, someone to eat lunch with, someone to hang out with outside the office. You need to be honest, because the truth will come out.” — Betsy McCann

We all spent the night taking in what we learned from Betsy and the next day we had the opportunity to sit down with professional head recruiters, in a group setting, to practice the interview process and receive real-time feedback from other students and the recruiter.

It was great because generally interviews are a one-way road. You answer the question, and the person(s) on the other side of the table analyzes your answer, makes a judgment, and moves on, and you truly never know how well you answered that question. Was I right? Was I wrong? The answers change for everyone and you only know if you did well if you get offered the job or not.

Performing these mock interviews and having that second person break down how you answered that question, handled the conversation, what your body language was like, etc., opened up our eyes and helped us all tremendously. The buzz in the room was great afterwards, and we each felt good on what we need to work on to nail the actual interview when they happen.


Continuing with our fire-side chats series, during Week 3 and 4 we met three incredible entrepreneur’s, two of them affiliated with Techstars, and each with their own incredibly valuable advice.

A man that needs hardly any introduction, Troy Henikoff from Techstars Chicago stop by from his supremely busy schedule to provide us with a gold-mine amount of advice.

Troy Henikoff from Techstars Chicago being interviewed Lauren Zaleski

Troy meets with hundreds of leaders and entrepreneurs every year and from his career, he believes that some of the best qualities of entrepreneurs are tenacity, coach-ability, and being stubborn.

Why stubborn?

Because stubborn people know what they want and what they don’t want.

But….one of the worst traits an entrepreneur can have is when they believe their opinion is the only right answer and being too stubborn about it.

Important to balance that appropriately.

Another thing Troy excels at, he knows what separates a good startup pitch from a great startup pitch.

One of the key parts of Troy’s job is practicing with the Techstar’s companies pitches and breaking down each and every single word down to the syllable by continuously asking Why, Why, Why, Why, Why (The Five Whys) to find the true root of their pitch and optimizing it.

The goal of this is to make that a great first impression to your customers, because like we discover last in the last blog, typically for startups you only get one shot to present your pitch.

As you test your pitch, you may get feedback like…

That’s a great idea! I’m going to tell my friends.

That may sound good, but is that the answer you want to hear?

What you want to hear is…

That’s a great idea! Here’s my credit card. I’m in.

Hard to build a startup, until you convert your customers.

Regarding building your team, a classic quote in the startup world is…

“Hire slowly. Fire quickly.”

And it’s one that needs to be stressed a lot in startups. It’s important you get the right people for the right reason. Quality > Quantity should be the foundation of a startup’s recruiting values.

Consider startups like a chain. At early growth companies, each employee has a key place within the company. A chain is only as strong as it’s weakest link. If one member of the team doesn’t perform well, the whole team will fail.

Troy knows a lot about what it takes to find the right people for your company, but what about finding the best company for you? Two of his top tips to getting into the right company are;

  1. Be passionate about what the company and what the team is doing.
  2. Find a person or team who you can learn from.

If you have found that company that answers both #1 & #2 , then get into that company anyway you can.

People in a startup move up so fast. Even taking a job as an unpaid intern or volunteering (and performing well) can pay off quickly.

A company that is currently working with Troy and going through the Techstars accelerator program is Partyslate (an event planning company) and the lovely founder Julie Novack visited to share her unique background and she described her experience going through the Techstars program.

Kate Garrity with the party planner of the city, Julie Novack.

We heard about her background and her steps to starting a company. How that idea originated and going through the steps in her personal life to make that switch to becoming an entrepreneur and starting a company from nothing.

Starting a company is always difficult. There are so many unknowns you will never consider until you try.

We questioned her on how do you set the baseline of your KPI’s (key performance indicators) during the beginning of a startup when you don’t have any data to start with. A great hint is to A/B test your KPI’s. See what numbers and metrics are working best for you and make that the standard, but be realistic about it.

Going through Techstars program, she’s spends a great amount of time perfecting her pitch and a helpful exercise to work on this is to perform A/B tests on pitch decks as well. Will help you discover key parts, what works, what doesn’t, to prepare for the big date when you do present.

Since Julie is a party planner, we couldn’t let her go without asking what are the key things for throwing a great party.

Her top 4 tips for throwing the best party in town;

  1. Lighting and music are key (more important than you think).

  1. Welcome your guests as they arrive.
  2. If having speakers, keep their presentations short and concise.
  3. Build the party around the bar / kitchen.
Learn from Snoopy and Julie, and don’t be afraid to try new things.

Dima Elissa from Vismed 3D (a startup providing 3D surgical patient replicas for state-of-the-art treatment and training of doctors) visited to remind us to “Be Authentic” and align yourself with people who believe in you. If there is something that you want, prepare for it, practice your skills, and find the direct messengers who can help you get what you want.

Dima was recently on the Tech In Chicago podcast. I recommend listening to hear more about Dima and her amazing vision. She is a prominent woman entrepreneur doing amazing things for the industry. Keep an eye out for her in the future.

To break away from the career learning and technical courses, we went on our first walkabout (or adult field trip as I like to call it) and checked out a few of the coolest tech offices in the city.

Spot #1 — The Nerdery (a custom software development firm)

It’s the Nerdery!
Being welcome to the Nerdery early in the morning.
The office map inspired by the Chicago Transit Authority.
The “Steam” room aka the game room that host many, many games of intense Halo.

Stop #2 — TangoCode (custom software firm)

Final Stop #3 — The WeWork Fulton Market, a co-working space.

WeWork Fulton Market’s conference room

As we approached the halfway point, it was time to celebrate and enjoy some brews and tacos at the annual Startup Institute Open Doors Party. It’s an event held each season for alumni, current students, hiring partners, and members of the tech community for an evening of making new connections, reuniting, and having fun.

This season’s Open Doors party was graciously hosted on the rooftop of the Opternative office. We were having so much fun enjoying the view and networking with over a hundred people, that Mother Nature wanted to join us! Oh boy did she bring a lot of water to the party. Most of the party prevailed in ponchos for a while, but it still all worked out as we swung by a nearby bar for an after-party.

This event was the first time I got the chance to meet the Startup Institute community and in a short time, I was welcomed by many awesome, unique, and talented individuals. This is truly a network of go-getter’s, that are fueled by great companies with extraordinary talent and personalities.

An awesome photo of our awesome staff team. (Photo from Startup Institute’s Open Doors Party by Sean Su, on behalf of CloudSpotter)

Like mentioned at the beginning, these two weeks we have begun hitting the books hard to solidify our technical skills and learn all we can. This will be one of the main focuses as we head into our junior year (week 5–6).

I am on the Web Design track learning the steps, languages, and skills with aspirations to become a Product Manager, UX Designer, and Web Developer. I’m a jack of all trades guy, I aim to excel in it all. So let me continue to study, research, and get my hands on every coding and design book out there, and I’ll present to you what I have learned at the end of this program.

So in the meantime, my personal site is under construction.

BRB while I rebuild my portfolio :) (yes I have a lot of extensions)

Whoa….we’re halfway done.

Through the leadership of our wonderful staff, we established a great foundation to act upon. Our tremendous director spoke to us about this one day during our daily morning stand-up;

“Now is our time for us to be like Picasso and create our own works of art.” — Lisa Schumacher

As we begin the second half of the program, you can guarantee we are ready to put words to action and execute. We are a hungry group of individuals.

Continue to follow us along on Twitter #SIChicago as we continue flying high through this program and give this guy a follow on Twitter @John_M_Egan. I love staying in touch with everyone and helping anyway I can.

I’ll leave you with this fun comic (before the cool resources). Considering all the election talk happening, seems appropriate.

(Note: Much of this blog are direct quotes or lessons I learned directly from the teachers / guests / speakers. Credit goes to the mentioned person in each part.)


Troy Henikoff (Techstars) //

Martin McGovern & Rajiv Nathan (Idealemon) //