How I Traveled the World, Started 2 Companies and a Charity, Wrote a Book, and Still Managed to Fail 100 Times by Age 24

Jordan Gross

There are a few secret words in here that are the keys to everything

I’m not sharing this to gloat.

I’m not sharing this to impress.

I’m not sharing this to garner attention.


I’m sharing this to reflect.

I’m sharing this to inspire.

I’m sharing this to engage.

I want to show all kinds of people out there, not just those who are my age or younger, that life is a tortuous series of events, and I have the ability to dictate the story and craft the scenarios in a way that I wish for them to occur.

I want to show people that there are a few critical ingredients I have determined throughout my journey that must be included to build the life of achievement, creativity, and fulfillment I desire.

I will simply walk you through the last 5 years of my life when all of this came to fruition (ok maybe I’ll start a little bit earlier).

I will give the lows and the highs, the why’s and the how’s, and of course the essential components I have come across along the way that have led me to a life of a lot, in a little amount of time. Each story I tell will display these 4 principles, which I truly believe are the most important characteristics in any experience I have in my life.

Back to the Beginning

Ok, so I lied. I actually started 3 businesses. The first one just happened to be when I was 7-years old.

It’s difficult to remember specific days, events, ideas, and conversations from my single digit years. Even what I do believe I remember is most likely just hazy depictions from friends and family describing the event, and me creating a memory out of the details I hear.

However, September 11th, 2001 I do remember.

I remember being taken out of school.

I remember looking at the TV.

I remember asking how and what could make so much smoke.

I remember seeing the tears roll down the faces of family and friends.

The destruction of The World Trade Center is one of those moments everybody remembers. Everybody knows where they were, who they spoke to, what they said. This is an unfortunate attribute of devastation.

But what I also remember is immediately wanting to do something to help.

I wanted to save people,

I wanted to change people,

I wanted to make people smile again.

So, another one of my earliest memories came on September 21st, 2001. With a few friends a few parents, some lemons, some cookies, and some water, we set up shop on a busy street corner and started selling.

But this was no ordinary lemonade stand. I mentioned I wanted to give back, and from that young age I started to think a little bit differently than everybody else.

Rather than pocket this money and make people smile simply by starting this stand, I decided that I wanted to give the money to the families who were impacted by the 9/11 tragedy.

Thus, the 9/11 Memorial Lemonade Stand was born.

I mentioned these 4 lessons that go into every story. And although this isn’t necessarily a business, and starting a lemonade stand may not be the first thing that comes to mind when thinking about a life of ultimate fulfillment, this is the first story in which all 4 of these words came into play.


I also said that I have experienced over 100 failures. Well this was the first one. In that feel-good story of young kids selling lemonade for families affected by 9/11, I didn’t mention that after an hour in the hot sun and no sales, I wanted to pack our things and go home.

But, it was the encouragement from some wise adults, the wisdom that we could not make a difference by doing nothing, and these wordsdetermination and persistence that I learned that day that have stuck with me all this time.


I mention the people involved in this effort. Without them, none of this would have occurred. The people in my life are everything to me, and the relationships I have with them are what I care about most.

I am still friends with the group that set out to make this lemonade stand. This was a meaningful experience to me and I was able to do it with people who mattered to me, and this bond has lasted a long time.


I always think a little differently. I am never scared to be unique. I know that if I want to be remarkable, I have to do something a bit unreasonable.

I knew that this lemonade stand was about more than just making money by selling these goodies. It was about being conscious and creative in the way that the proceeds were distributed, and this is why we became neighborhood superstars.


To achieve a lot, you have to do a lot. I am never reluctant to take on a new project or test an idea I have been thinking about.

I always allow the fear of the “what if” to outweigh the fear of the actual doing.

That is, I am more afraid to look back and think about what could have been.

What if I had asked her out?

What if I had started that business?

What if I had quit that job?

It is scarier to wake up and realize who you could have become than it is to take part in the process of who you want to be.

Failing Freely

A beautiful phrase by my good friend Brandon LaBella, this is now the part of the story in which I received my next 25 failures.

I had 25 schools on my wish list for where I could go and play soccer. I reached out to 25 coaches around the country, received 25 opportunities to impress, and failed at all 25 of them.

I received 0 offers.

But I persisted, I was determined. I had explored 25 universities, and I chose one where I would have the best experience. I attended Northwestern University in Chicago and never looked back.


Did I want to stop after the first 10 rejections?


Did I?

Absolutely not.

The 20th or so school was Northwestern, and with soccer out of the picture, I could not have made a better choice.


Had I not gone to Northwestern, had I not met these people along the way, I would be nowhere near who I am today.

It’s that simple.


I took a creative approach to choosing a school once my soccer aspirations were cut short. I wanted a school with great academics and great athletics, but I also wanted to be a little different (there is that theme).

Rather than going a normal route, I looked more at what schools students from my high school were attending less frequently, and Northwestern was right on the money.


Again, it’s all about starting. Had I not been proactive about finding a school I desired, I never would have ended up where I deserved to be.

Traveling the World

Everything in this story in one way or another leads into the next thing. I don’t often say that everything happens for a reason, but just maybe they do. One thing is certain:

Everything happens, and then regardless of the reason, you create the response that leads to what happens next.

How many failures am I at?

26, thanks for reminding me. How about we add 10 more?

Sophomore year of college, I was going down the traditional investment banking route so many of my peers craved. I was straying away from my creativity and uniqueness, but something great happened!

I applied to 10 firms, and I got rejected from all of them!

Needing to do something with this important summer, I went to the handy dandy school summer opportunity list to see what I could do, and got back to my creative roots.

Through an immersive experience, I ended up traveling to London, exploring all of Europe and Asia, and getting class credit! It was magical!


Just because I did not get the banking job I wanted did not mean I would sit back and relax all summer. I struggled forward (thanks Tim Rettig), and I came up with something new and adventurous.


The people I met on this excursion are some of my closest friends to this day. Additionally, without the proper guidance from the awesome ladies I met in the study abroad office, I would never have been afforded this opportunity.


I had to think quickly and think outside the box to come up with an experience that I may never receive again, and one that would be impressive enough to get the job I wanted the next year.

I did my research, I made my connections, and I came up with something not many other students do, and it paid off.


It may seem like this opportunity or all of my opportunities came due to some sort of privilege. However, this is not the case. Especially with this one, I had to apply through a rigorous process, learn and study the ins and outs of a program I may not be accepted to, and make the right connections and relationships to be accepted into the program.

Had I not gone out and found this great program, I would have been on the couch and things may have been extremely different in my future.

One Man’s Failure is the Same Man’s Treasure

36 failures and climbing.

Let me slap on another 10 consulting firms, 2 tech firms, a startup proposal, and a non-profit idea, and I am halfway there!

Again, I was convinced to adhere to the norm of my peers and apply for consulting jobs. A blessing in disguise, I did not get any. At the same time, I was also exploring the startup world, loving entrepreneurship, and my grandpa had just passed away from Alzheimer’s.

At his funeral when giving a brief eulogy, I did the only logical thing I could think of on the spot, and committed myself to starting an organization devoted to supporting Alzheimer’s patients and carepartners (a common Alzheimer’s phrase) around the country.

I sent in my first proposal, no luck.

After revising the objectives, activities, and scalability of the group, I was on my way to starting something.

My group, They Forget, We Remember would focus on Alzheimer’s Awareness through Volunteering, Support, Education, and Fundraising. All proceeds went to Northwestern’s Alzheimer’s Disease Center.

This allowed me to help lead a nationwide effort called The Youth Movement Against Alzheimer’s spreading awareness for the disease from a youth perspective. I went on to pursue a master’s degree to work on my management skills.


After getting rejected from more jobs and hearing no about my application for this charity the first time, I easily could have taken a step back and pursued a different route. But, I knew that what I was doing was going to make a difference, and I would not allow a minor setback to stop me from doing what I knew could benefit the greater good. So I rethought, I recreated, and I pushed forward.


I started this organization with 2 or 3 core members, and grew it to 30. I met Alzheimer’s patients and carepartners around the country, I appeared in documentaries, I met celebrities, and I still interact with these people on a regular basis in an effort to fight this horrid disease.

At the end of the day it’s all about people.


I mentioned that all proceeds from fundraising went to Northwestern’s Alzheimer’s Disease Center. This was the difference maker. The fact that I had strategically come up with a partner that could use the benefits of our services in a tangible way, rather than a large organization in which nobody really knows how funds are allocated, set this group apart from so many others.


This was all about taking action. This was about making a statement to others and holding myself accountable to it.

A great way to stick to what you say is to be open about it and create some accountability by telling others.

The Entrepreneurial Bug

Having started my own business and getting into management techniques and styles, I was starting to become fascinated by starting things and watching them grow. It was time for my own startup. I worked with a professor to go through ideas.

5 shot down immediately, 55.

One however piqued her curiosity. I was complaining about order time using all the food delivery apps, and we thought it’d be a cool idea to figure out a way to minimize this. Thus, I created Feed My Mates.

Based off of what I was already doing in preparing a meal for my roommates, the startup offered 1 meal offering per night, with options Meal? Or No Meal?

With considerable growth and 5 team members over a few month process, I thought it’d be a wise time to test out investors.

My team and I cold emailed 40 investors and received 0 bites.


The company continued on though, and we actually pivoted to focusing on a cookie we had been giving out for free as a token of our gratitude.

This cookie, a mandel bread cookie baked by my mom, became known as MomdelS, the second company I started. This one is still a work in progress!


Many times relentlessness leads to the “big win”. Stories of, “The final attempt was when I got the call I was looking for”, run rampant in the entrepreneurial success story world.

But I didn’t have the big break. Rather, I celebrated diversions that led me down different paths, I kept at it and other opportunities arose. Opportunities that led me to where I am today.


I’m like a broken iPhone, but the people I went along this journey with, I still speak to a year later. We still share stories and reminisce about the awesome times we had.


The concept behind Feed My Mates was based on being different from other services. Making a small change, making a small shift, making a small improvement is creative enough to make something work.


I had an idea, I tested it, I built a team, and I worked on it.

It’s that easy!

Proof of concept is sometimes all that is necessary to go all out on an idea. It is all about doing rather than sitting back and waiting for somebody to do it before me.

Lighting up Others

Fast forward a few months to November 2017, I just quit my corporate job, and it’s time to do what I truly want to do with my life —

Add value to others without expecting anything in return.

I decided to do so in the form of a book that focused on overcoming stress and anxiety by practicing a morning routine to enhance productivity, energy, and happiness.

My youthful exuberance, optimism, and most of all naïveté forced me to believe that a traditional book publishing deal with a massive advance was within my reach! 23-year old corporate refugee with a solid background and education, no problem!

I was very wrong.

I sent my proposal to 5 publishers and guess what?

96, 97, 98, 99, 100.

100 failures by age 23 and a half.

But this certainly didn’t stop me.

I ended up self-publishing my book and have been on this journey to empower others ever since.

One last time:


Could I have tried 50 more publishers who may have given me a chance? Possibly. But, instead I chose a route more fitting to the situation, I put my luck in my own hands, I did everything I could for this book, and I am proud of it.

And by the way, I will not stop reaching out to publishers for the next book!


You all here on Medium! This entire Medium journey began out of an idea to promote the book using this platform. I aim each day now to inspire the people I have met and have yet to meet on Medium to continue doing what inspires others, and what lights them up inside.


The morning routine, just like everything else I do, has its own flare to it.

C O M F Y. Getting COMFY is the name of the game, the acronym for how to wake up each morning, and the way we should all live our lives.


I quit my job, took a calculated risk, and I did it.

Just do it. Nike certainly has something going for it.

I think about these 4 words when embarking upon any journey or experience.

My relentless attitude in achieving what I desire.

My amazing relationships I will make throughout the process.

My creative approach to everything I do.

My ability to take initiative and pursue my dreams.

I have succeeded, I have failed. I have won, I have lost.

I have done a lot in my almost 24-years here on this earth, and I do not plan on stopping any time soon!

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Reimagining Personal Development

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