Ending Soon! Save 33% on All Access

The 5 Lessons I've Learned From 5 Years as an Entrepreneur What I'd tell the 21-year-old version of myself if I could go back in time.

By Jess Ekstrom

Opinions expressed by Entrepreneur contributors are their own.


I recently celebrated the five-year anniversary of my college startup, Headbands of Hope, which gives a child with cancer a headband for every one sold.

I was inspired to start my company after an internship with a wish-granting organization. I discovered kids losing their hair to chemotherapy often wanted to wear headbands instead of wigs or hats.

To date, the business has done some incredible things. We've been featured on Good Morning America, Vanity Fair, The TODAY Show, Seventeen Magazine, Cosmopolitan and worn by countless celebrities. But, the milestone I'm most proud of is donating over 100k headbands to children's hospitals across America and six countries.

Sometimes, when you have a business and you're constantly looking forward, it's hard to realize how far you've come. That's why I wanted to look back at my junior year in college when I founded the company.

I've learned so much. I continue to learn every day (usually by making mistakes . . . but we'll get to that later), but here are five key things I've learned in five years of entrepreneurship.

1. Use your resources

I started my business with a small account of funds I saved up from my Disney World internship the year before. I never sought out investors or thought about the funding I didn't have; I looked at what was on the table for me right then and there. Beyond money, the biggest resource I had was being a college student. As a communications major, I knew very little about entrepreneurship (it took me forever even to learn how to spell it!). So, in between classes, I set up meetings and appointments with students and professors at the business school to share my idea and get their input. I started to tap every department I felt could help me: design school, textiles school, marketing department and the list goes on. Little by little, Headbands of Hope evolved into a strong startup because I used all the different areas of expertise my college had to offer.

You can always come up with a list of things you wish you had, but that's not an efficient use of time. Instead, identify what's right in front of you and start there. You'd be surprised what you can accomplish when you're resourceful.

Related: How to Start a Business With (Almost) No Money

2. Take care of your people

I used to think great entrepreneurs and business owners were successful because they were all really smart and hard-working. That could still be true, but there's a key element even more important than hard work and brains: your team. My company would not be what it is today without the people around it, and I find the most important element of my job is making sure my team has everything they need to do the best job they can -- whether that's tech tools or just my support and trust.

Steve Jobs most likely didn't come up with the iPod, but he built a team of people who believe in innovation and were trained to think outside the box. I've learned being a leader isn't about being the smartest or having the best ideas, it's about creating a team that cultivates innovative ideas and passionate work.

Related: 22 Qualities That Make a Great Leader

3. Show up

When I look back on the turning points in my business, I can usually pin point a time where I chose to just show up. It may sound silly or simple, but opportunities won't happen to you if you're not there for them. It's easy to stay at home and work from your computer, but that's not where life happens. I used to weigh opportunities by who else was going to be there, what could I get out of it, what the expense was etc. Now, I try to not look at things so transactionally and instead understand that it's always worth meeting new people.

One time, I was asked to speak last minute at a conference in Raleigh. I was busy that day but decided to show up to give a quick talk and then get back to work. Turns out, the other speaker was Jeff Hoffman, the co-founder of Priceline.com. We hit it off. Now (two years later), he serves on my board of advisors. We talk regularly. He's been an amazing mentor and a wonderful friend.

Don't have an agenda or a list of people you want to meet, just come as yourself and be open to opportunity. You never know what will happen.

4. When you fall, make it a part of your dance

When you slip up, just weave it into your story. Failures don't have to be a red light or a brick wall in front of you; consider them a pivot or an extra step.

I've found that people who have perfect track records usually become a prisoner of their own success. They're afraid to take risks for fear it might mar that perfection. Because of that, they usually stay right where they are or play it safe. Safe places aren't where growth happens.

Once, when I was in a business competition at Under Armour, I made it to the final round and lost. But when I was there, I developed a great relationship with Under Armour and we ended up repurposing their extra materials to make donated headbands for John's Hopkins Children's Hospital. It wasn't the outcome of the competition I was hoping for, but it still developed into an incredible experience.

You might not always get what you want, but always look for value in the experience.

Related: Inspiring Quotes to Help You Get Through Your Work Day

5. Remember why you started

Starting a company can be really, really hard. There, I said it. Starting and building my business has been the most challenging thing I've ever done, but it has also been the most rewarding. I've learned that meaningful work doesn't mean it's easy -- it means it's going to be worth it. Whenever times get tough, I pull up a file on my computer of all the pictures and letters we've received from hospitals (thousands of them) and remember why I started this in the first place.

At the end of the day, success is not what it looks like to others, it's what it feels like to you.

Jess Ekstrom

CEO and Founder of HeadbandsOfHope.com, Speaker and Author.

Jessica Ekstrom founded Headbands of Hope when she was a senior in college in 2012. She created the company to bring joy back to kids who have lost their hair and help fund childhood cancer research. Headbands of Hope has given tens of thousands of dollars to childhood cancer research and has donated headbands to every children's hospital in the United States.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Business News

TikTok Reportedly Laid Off a 'Large Percentage' of Employees as the App's Fate in the U.S. Remains Unclear

Laid-off TikTok employees were notified Wednesday night through Thursday morning.

Business News

More People Are Exploring Entrepreneurship Because of This Unexpected Reason

More new business applications were filed in 2023 than in any other year so far.


8 Subtle Hints that People Don't Respect You — and How to Fix Them

While you have to earn respect, you don't have to deal with disrespect in the meantime.

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.

Business News

Four Seasons Orlando Responds to Viral TikTok: 'There's Something Here For All Ages'

The video has amassed over 45.4 million views on TikTok.