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Steven Van Alen: “Here Are 5 Things I Wish Someone Told Me Before I Became CEO of Sleepyhead

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Steven Van Alen. Steven is the CEO of Sleepyhead and is passionate about both sleep and mitigating the effects of poor sleep can cause on college students. Throughout the years Steven has cultivated an understanding of business which […]

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As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Steven Van Alen. Steven is the CEO of Sleepyhead and is passionate about both sleep and mitigating the effects of poor sleep can cause on college students. Throughout the years Steven has cultivated an understanding of business which has been infused in his company: Sleepyhead.


Thank you so much for joining us! Can you tell us the story about what brought you to this specific career path?

The idea for Sleepyhead stemmed from my sister’s experience. When she was a college student, she was homeless, and had to sleep on the hard concrete floor while being nine months pregnant. Also, I saw the need while visiting friends who lived in the dorms and were given a thin, worn down, and unhygienic mattresses to sleep on. When it was my turn to begin college, there was much confusion as to where a mattress topper could be bought, and which one would be right for the beds. Despite trying to find the correct topper, their toppers were worn and ruined by the end of the first semester.

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

One of our first shipments of mattress toppers were shipped from overseas in a Hanjin container. Little did we know, they filed for bankruptcy. When our shipment reached the LA port, we were unable to access the toppers because the vessel that held them was seized and held up in bankruptcy court, even though the product within the vessel was ours. From this experience, we learned to work with freight forwarders who book cargo ships without financial issues.

What are some of the factors that you believe led to your eventual success?

How I conduct business has a lot to do with my success. I am a founder who is cash efficient, scrappy, and pragmatic.

“Success occurs when opportunity meets preparation. If one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours.”

“Nothing in the world can take the place of Persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and Determination alone are omnipotent. The slogan “Press On” has solved and will always solve the problems of the human race.”

What are your “5 Things I Wish Someone Told Me Before I Became CEO”?

  1. The CEO position is lonely. I think a misconception people have with being a CEO is that there are many assistants and helpers, which can be true, but often times it’s just the CEO who carries the weight of everyone and everything. With everything riding on my shoulders, I spend a ton of time thinking to try to figure out solutions to problems. I oftentimes have to isolate myself to think things through.
  2. In my opinion, being a CEO is the most challenging job one can pursue, which is probably why they are paid so much. Most employees have just one job such as admin, Facebook advertisements, or sourcing. But, a CEO wears multiple hats where they have to manage and oversee all the employees and all the processes. It can be difficult to figure out a way to manage everything without getting too burned out.
  3. The typical “term” for a CEO within a company is 3–5 years, because CEOs get too burnt out around the 2–4 year mark. Again, it’s a lot of pressure and there are many variables that the CEO constantly has to think about. For example, I talk with customers and investors who both have different worries and different styles of language. I have to quickly adapt to the situation in order to meet the need at hand.
  4. I wish someone would have guided me on the people I should and shouldn’t work with. It’s an extreme waste of time to work with people who end up being scammers. I’ve found that working with people who I’ve known prior to Sleepyhead has attenuated this problem immensely. The people who I know I can trust, and I know how they present themselves. Sometimes you meet people through networking, only to find out later that your ideas do not align.
  5. Finally, I wish someone would have told me about all the fires I would be responsible for. Being a CEO is like being a firefighter, in a way. Every day is different, but at the end of the day my sole purpose is to prevent fires, put out fires, and clear brush for new growth.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

This is an excellent question, because burnout can occur quickly without some mitigation. For me, the passion and the purpose help motivate me and prevent burnout. My work is fulfilling and it serves my purpose and passion, and I chose to develop a company that met those needs. Some people end up in CEO roles as a stepping stone or for the paycheck, which is fine, but ultimately burnout will ensue a lot faster.

I got an email from an NBA agent about a recently drafted 20-year old who would be playing for the New York Knicks. He was interested in our product, so we sponsored/endorsed him on the journey he was about to embark on. This is an example of what we do at Sleepyhead; sponsoring and endorsing professional athletes who were once -or still are- college students. We support college students’ dreams. This experience helped refuel me. I hope to sponsor more professional athletes in the future, however, I recognize this is no easy task and will keep my flame lit.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

The majority of my help has come from Shawn Nelson who is the founder and CEO of LoveSac. My family was not of much help to me; my father suffered from mental illness and my mother became a teacher. Entrepreneurship is in my DNA and it’s something I was born with. However, with Shawn, we both specialize in ecommerce and selling furniture, so he has been a huge asset to my growth, and an amazing mentor. Our relationship is comparable to that of Eminem and Dr. Dre.

What are some of the goals you still have and are working to accomplish, both personally and professionally?

I still have many goals that I wish to accomplish for Sleepyhead. I want to put Sleepyhead in a position where we can make a lot of noise in the mattress topper industry or be more public. We have our work cut out for us to get to this position. As time passes, I’m growing significantly as a founder and CEO and learning about things that I did not and would not learn in school. For example, in school I do not learn about the process for raising capital and who to raise it from. Real world implementation of school-taught ideas presents challenges that only critical thinking can solve. I want to be a better leader and have a good reputation, but I also will not allow people to walk all over me. Because I am young, people try to take advantage of me because they assume I do not have the same experiences, which is not true. With good habits, and a good head on your shoulders you can make a positive impact. On a more personal note, I would really like to get into mindfulness meditation to help see things clearer and further prevent burnout.

What do you hope to leave as your lasting legacy?

I know that Sleepyhead will not be the last company I work on, but I am passionate about sleep, homelessness, and college students getting better sleep. I want to infuse those concepts into my legacy regardless of what I do. I am also passionate about the environment, climate change, and the issues circulating those topics. I hope to help people also figure out how they will be successful in the financial markets and set themselves up for retirement properly. In sum, I want to leave behind that I’m passionate about helping others, and passionate about the environment.

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

Sleepyhead already has a charity component embedded into the company where we donate a mattress topper to a person in need for every ten sold. This philanthropy is incredibly important to where we are located, within the USA because 9–14% of college students are considered homeless and do not have a permanent address. I am also passionate about eliminating air pollution, and am the owner of a nonprofit which switches gas powered lawn mowers out with battery powered ones to help mitigate air pollution. I’d like to start a movement that encompasses these two ideas of saving the environment and bringing resources to people in need.

How can our readers follow you on social media?

IG: @StevenVanAlen and @SleepyheadUSA

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