Lessons Every Entrepreneur Should Know

Pillow.com founder Sean Conway reveals the secrets behind the success of his startups and what he would tell any budding entrepreneur.

Sean Conway is on the ski slopes. A 2007 graduate of the University of Arizona with a marketing and entrepreneurship degree, he recently sold to Expedia his runaway-success company, Pillow, a short-term apartment rental platform that benefits both owners and tenants. Now, after 10 years of startup hard work, he is kicking back a bit more.

“We ended up growing Pillow.com for about five and a half years, raised a bunch of money, hired a bunch of people, and Expedia acquired us in 2018,” Conway says. Today, Expedia is merging Pillow into its Expedia multifamily platform.

A seasoned entrepreneur with more than one startup under his belt (he also founded Notehall, an online marketplace that allows college students to buy and sell class notes and later acquired by education technology company Chegg), Conway shares how he found success in his most recent venture and the tips he wishes he’d known 10 years ago.

Find Your Why: “There isn’t anything I enjoy more than traveling, exploring new places and understanding cultures. Through these adventures, especially in developing countries, l couldn’t help but grapple with why I had the ability to travel and most of these locals didn’t.
Ever since then, I’ve devoted myself to breaking down the barriers that keep people feeling separate, isolated and tied down by a place or a label.”

Know What Your Customers Want: “Rental expense is a high financial burden for many people, with the average renter spending 28.4% of their income on rent. At the same time, our surveys indicated they were gone 41 nights a year on average. We decided we wanted to give residents the freedom to short-term rent, open up their doors to guests and find financial freedom. Residents who were traditionally barred from subletting their units now have the opportunity to use their rental as a financial asset and can earn extra income; once-reluctant landlords now benefit from transparency and increased net operating income (NOI).”

Understand Yourself: “Know what you’re good at, what you want to get better at, what you’re not good at, and what you should delegate. Also know what/who gives and takes energy from you. Then write these down. As you begin to understand this, you’ll develop a routine and environment with friends and colleagues that propel you to run a business at your highest capabilities.”

Set Goals: “Five years ago, I was introduced to objectives and key results (OKRs), which is basically goal setting on steroids. These OKRs became the guiding compass for our team. Early on, I recommend resetting OKRs every one to two months. Then every three months once your team reaches 10 to 12 individuals. OKRs have created such a [return on investment] in my professional life that I’ve now implemented them as a goal-setting structure in my personal life.”

Take Pride: “One of my favorite parts of the business was hearing stories about the Pillow residents — who they were and the opportunities Pillow has given them, such as a group of flight attendants who could now afford their own places versus living with roommates, or teachers who said they could now afford traveling on summer break. These stories are what get me excited and differentiate us.”

Prepare for the Challenges: “Jumping into each startup is one of the most exciting and stressful, but gratifying, things I’ve ever done. However, be ready to make sacrifices. Life happens around you while you’re running a business, especially in the first few years.”

Invest in a Network: “Entrepreneurship is tough, and you’ll naturally run into adversity. When you don’t need advice, you’ll want someone to just commiserate with. Our fundraising events and both acquisitions were each seeded through introductions from my network. Ask for introductions, foster those relationships you care about that will spawn into more.”

Build your professional network on the Bear Down Network, a platform that connects University of Arizona alumni and provides access to resources that foster career development.

By Lacey John
Lacey John