entrepreneurial leap

Making the Entrepreneurial Leap: The Wins, the Woes and Everything in Between

Starting your own business can sometimes seem like an unachievable pipe dream; something that will forever remain in the back of your mind as you struggle through a day job that you don’t enjoy. And as many will love to remind you, making that leap is less like a big-yet-feasible challenge, and more like scaling your own personal Mt. Everest.

My own entrepreneurial journey began in New York. I’ve always been good with numbers, so a career in finance seemed to be the best option for me coming out of college. But after a while in the industry, I realized it didn’t give me the fulfillment I desired.

Growing up, the great outdoors was a major part of my life – especially skiing. My father owned a brick-and-mortar ski shop and some of my best memories are from heading up to the slopes with my friends and family. While my job in New York gave me financial freedom, it constrained me from pursuing things that I actually enjoyed. I decided to start my company in 2014 and it turned out to be the greatest decision of my life. 

Sometimes it’s difficult to know when you need to take the leap into a bold new industry. Having lived through this decision, I know how to approach the ups and downs of beginning your own entrepreneurial journey.



Making the leap

I remember my “aha!” moment like it was yesterday. Growing up in a skiing-obsessed family, my father always lent out ski apparel to close friends and acquaintances who didn’t own their own winter clothing. While many ski resorts offer equipment rentals, there are very few options to rent ski apparel to use on the mountain. And the ones that do often only offer basic options unassociated with the name brands. When talking to my dad one day, it all became clear: Why not turn this into a full-time business? And so, I started Kitlender: a short-term ski apparel rental service.

My advice is to jump in before you’re completely ready and the rest will follow. Of course, this doesn’t mean you should start your business with absolutely no planning. Make sure you have the structure of your company well thought out beforehand. Determine how you will access capital and how long you can run the business on that capital. Remember that things will always end up costing twice as much and taking twice as long to do.

But nobody thinks they’re ready, and to be completely honest, they’re right. You’re going to make mistakes no matter how prepared you are. The best advice is to not dwell on them. Instead, learn and adapt as you go. I beat myself up on things that I wish that I had done differently in the beginning stages of my company. You can’t predict everything that will happen and expecting everything to be perfect will only make things harder.

Balancing work life with more work life

If you’re not totally confident that your new business will take off, sometimes it makes sense to hold on to your day job while you figure things out. I have a perfectionist attitude, so I wanted to make sure that I had everything in order before I quit my 9 to 5. But as you can imagine, working two jobs pushed me to extremes I didn’t know I could reach. 

My 9 to 5 soon became a 9 to 10, then 12, and the next thing I knew I found myself working throughout the entire night. I barely got any sleep as I devoted any extra hours to developing my own company. Soon, my personal life had completely disappeared. I lost the ability to engage in activities that I enjoyed. And most importantly, I didn’t have time to do the thing I loved most: skiing.

So I took a step back and asked myself if I was happy. I asked myself why I continued to kill myself working a finance job I had no passion for. And then the decision became easy: I decided to quit my day job and devote all my attention to my own company.


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Finding purpose

Working in finance was great in some ways. It gave me all the money I could possibly need to live in one of the greatest cities in the world, New York. But after years sitting behind my desk helping rich people sort their money, I realized that the job didn’t give me the fulfillment I needed in order to truly feel happy.

I started my company in large part because skiing is something I’m passionate about, but also to have the flexibility to support causes that I care about. Most recently, I worked with an organization called Knights of Heroes, which organizes trips for children whose parents recently died serving our country. We ended up donating 30 kits to the organization for their skiing trip. 

I still get emotional thinking about this partnership. A mother of one of the kids sent me a personal note telling me how much the trip meant to her son, and how great it was to see a smile on his face. I simply couldn’t help out in a more hands-on way while working in finance, and the ability to give back is a major part of why I enjoy owning my own business. While finance brings in the money, it simply doesn’t offer the kind of real world value that I’m passionate about.

Owning your own business allows you to have the flexibility to pursue opportunities in whatever areas are important to you. When you own your own business, the opportunities are virtually endless.

Five years later, I fondly reminisce on the beginnings of my company. I started working out of a small area in a basement, and now I’ve expanded to a 7,000 sq. ft. facility and am looking to expand even further. I used to do everything: marketing, finance, fulfillment – I was a true one man band. Now, I have a dedicated staff that do these things for me much better than I ever could. I’ve had both wins and losses, struggles and triumphs throughout these five years. And I look forward to experiencing much of the same in the future.

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