“Starbucks is Not Always the Best Option for Free WIFI” The 5 Lessons I Learned Being a 20-Something Founder

I had the pleasure of interviewing Jordan Gross.

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I had the pleasure of interviewing Jordan Gross.

Jordan Gross, Writer, Executive Leadership Coach, Speaker, and Personal Trainer, and Author of the #1 best-selling book Getting COMFY: Your Morning Guide to Daily Happiness. Jordan founded multiple companies and organizations in college, went into the management world, and then left at the age of 23 to pursue his goal of adding value to others without expecting anything in return!

Jean: Thank you so much for doing this with us! What is your “backstory” of how you become a founder?

In my 23-year existence my career path has been quite tortuous, but certainly not torturous! It began in high school, working summers in a warehouse for cleaning supplies, unloading and loading boxes 9–5, and then staying an extra hour to teach the other workers English.

I then attended college at Northwestern University, and worked my first summer as an Inside Sales Intern for a software development company, making 300 calls per day. I took on a project consulting for a non-profit that provides independent housing for disabled adults and closed that year with an internship in finance at Merrill Lynch. The following year I was consulting at a Chicago firm called Accelerated Growth Advisors, where I worked with rapidly growing clients like rxbar and Spikeball. Meanwhile, I had started a student organization providing support, volunteer efforts, and funds for Alzheimer’s awareness. This is when I developed my life motto: Add value to others without expecting anything in return.

I spent a 5th year at Northwestern, enrolling in The Kellogg School of Management’s Masters of Science in Management Studies Program. While there I continued to pursue opportunities to add value by doing independent consulting projects for food delivery companies Chowbus and Wise Apple, and I also started my own company called Feed My Mates, which delivered healthy meals around the Chicago area and incorporated an online negotiating experience for each customer. I finished school and took a corporate management role with Hillstone Restaurant Group where I was in charge of day-to-day restaurant operations for their location on Park Avenue in New York City. After 4 months of 14–16 hour days, I needed to get back to my roots of adding value, building relationships, and growing something. I quit in November 2017 and began what I do now.

Jean: What do you think makes your company stand out? Can you share a story?

Getting COMFY stands out because it is totally people based. It is a burgeoning brand that aims to guide young students, workers and entrepreneurs from the second they wake up in the morning. The most exciting opportunity right now is the willingness to try new things. We have created a variety of courses, campaigns on social media, and contests for people to get involved and more importantly, engage with the brand!

We did a full day in the life video series, starting at 4:30am and going all the way until 7pm, which highlighted what exactly it is a morning routine based entrepreneur does every morning and every day!

Jean: Are you working on any exciting projects now?

Yes, a bunch! I am about to become the youngest Marshall Goldsmith Certified Executive Leadership Coach in the United States (it would have been the world, but a girl in Russia got certified a week before her 24th birthday, and I will be a week after), so I will be working with leaders in an effort to change their behavioral strategies with the key stakeholders at their companies.

I am also working on two more books, one fiction and one non-fiction which are both super exciting!

I am also working on a speaking engagement tour in Ghana, where I will empower youth to wake up to their full potential every single day!

Jean: Do you have a favorite book that made a deep impact on your life? Can you share a story?

I have 2 — the first is Dale Carnegie’s How to Win Friends and Influence People, which are basically the guiding principles with which I live my entire life.

The second is Hal Elrod’s The Miracle Morning, which I based the concept of my book, Getting COMFY off of. I heard about this book on a podcast when I was hungover sitting on the runway on a plane, and my hangover was instantly cured because of how engaging and revolutionary I thought the strategy was!

Jean: What are your “5 Lessons I Learned as a Twentysomething Founder” and why? Please share a story or example for each.

1. Starbucks is not always the best option for free wifi — I often like to get out of my apartment to do work, and I often go to Starbucks for free wifi, air conditioning, and food and drink access, even though I don’t really drink coffee!

One day, I got there a little later than usual and it was particularly packed. I could not find a seat for over 2 hours, and I ended up doing work standing up and holding my computer that day!

I like Panera now instead!

2. Funny looks should be viewed as exactly that — Many people will question your courage, your out of the ordinary career path, and give you questionable looks. But, this is all they should be viewed as: funny looks. These people are unwilling to comprehend the level of discipline, the mental fortitude, and the determination and persistence it takes to take on an experience like this.

3. Some people are really REALLY interested — Unlike the last group of people I mentioned, this group of people are your breath of fresh air. These are your lifelong supporters, your loyal fans, and the ones you should aim to interact with most!

I have made friends with people from around the world! One guy from India messages me regularly just asking for updates on what I am doing! A little creepy, but humbling I guess?

4. It is lonely but not lonely — I am talking to people all day long on every single mode of communication, but sometimes it feels like I have nobody by my side. Sure, this can be tough sometimes, but then you receive the supportive messages, the ones that instill hope, and are inspired to push forward.

5. Pursue every opportunity because you never know and should never stop learning and conversing, but they sure won’t all be great — 2 stories here, 1 good and 1 bad. I have been on a lot of podcasts and most are small, newish ones, and I still do them to get my name out there of course.

One actually ended up becoming huge, with the guest right after me being Phil Hellmuth, World Series of Poker Champion!

One however, was a 11:30pm radio show (should have known right then and there) that ended up being the most vulgar, vile and inappropriate 20 minutes of my life!

You should never say no just to say no, but make sure you do your research!

Jean: Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

Jessica Alba, let’s grab lunch! For two reasons mainly. First because she has been able to reach peak performance in two of the toughest and most competitive spaces in the world — acting and consumer products in business.

And second because she made a bold career choice and transition that some may have viewed as questionable but ended up absolutely knocking it out of the park. She is one of the most impressive and successful people I could ever imagine meeting!

— Published on July 19, 2018

Originally published at

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