How a Bad Money Experience Inspired One Entrepreneur to Develop a Roommate-Rating App Chillow co-founder Stephen Rankin discusses the launch of this real estate platform.

By Entrepreneur Staff

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In this ongoing series, we are sharing advice, tips and insights from real entrepreneurs who are out there doing business battle on a daily basis. (Answers have been edited and condensed for clarity.)

Who are you and what's your business?
My name is Stephen Rankin. I am the co-founder of Chillow, a mobile app that's available on IOS and the Google Play Store. We provide a platform for roommates to find a place to live and also provide the ability for people to review, rank and endorse current and former roommates. Our algorithm allows renters to be matched based on location and lifestyle choices. We also partner with property management companies to reduce tenant turnover and fill complex vacancies.

Related: It's Never Too Late to Launch Your Dream, Say These Skincare Entrepreneurs

What inspired you to create this business?

In 2010, two roommates and I had an unfortunate experience with our fourth roommate, who was responsible for turning in the rent each month. Instead of paying it to our apartment complex, they went to Las Vegas and lost it gambling. We were evicted and forced to cover the costs of finding a new place to live. At that time I thought, why isn't there somewhere I can review what my living experience was like with this individual so that others are aware and someone else isn't wronged? I kept the idea for 8 years before putting it into action, starting a business, and developing a mobile app.

What has been your biggest challenge and how did you pivot to overcome it?

A big challenge we faced came when we paid a freelance developer $35,000 upfront for the contracted work, and later found out that they weren't following through on what their commitment. I pivoted by hiring an intern to document the mistakes and track the lack of progress. From there I was able to allocate a new developer to take over and fix what had been done wrong.

Rankin with his wife and co-founder Alexis Rankin after winning the Boise Startup Week competition in 2020.

What advice would you give entrepreneurs looking for funding?

Look for investors who have participated in your field. But before you start having those conversations, make efforts towards a seed round, a crowd-funding round, or friends and family raising. One thing that will greatly benefit you is if your business is making revenue before you speak to investors.

Related: You Don't Have to Be a Business Owner to Think Like an Entrepreneur

What does the word "entrepreneur" mean to you?

Ideally, being your own boss and creating a life by design, not living a life by default. Creating a product/service that benefits others. Growing the business to the point where you can step away and have it run efficiently. If not, you're an employee of the company you started. I've also considered an entrepreneur to be someone who is an active go-getter. They set their mind to achieving something and have zero distractions in accomplishing their goal.

What is something many aspiring business owners think they need that they really don't?

Many aspiring business owners think they need their idea to be a secret. You do not need to keep your idea a secret. Share your idea with others, gather their feedback, and gauge whether your product/service is something that others find beneficial. In the process, you may uncover your market.

Is there a particular quote or saying that you use as personal motivation?

"It is easy to be pleasant when life flows by like a song, but the man worthwhile is the one who will smile when everything goes dead wrong. For the test of the heart is trouble, and it always comes with years, and the smile that is worth the praises of earth is the smile that shines through the tears." — Ella Wheeler Wilcox.

There will be good days and bad when you embark on your career journey. You cannot appreciate one without the other. This quote is a testament to that and I've read it many times when times are tough.

Related: Forget a Business Plan. Here's All You Really Need to Launch, According to This Art Book Entrepreneur.

Entrepreneur Staff

Entrepreneur Staff


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