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Five minutes with … Jordan Allen, Founder & CEO, Stay Alfred

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We catch up with Jordan Allen, Founder & CEO, Stay Alfred, to learn about his career milestones and most valuable lessons

Jordan Allen founded vacation rental start-up Stay Alfred in 2011 and has since grown the business to over 2,500 apartments with hotel-style amenities in 33 cities across the US. Prior to entering the travel industry, Allen spent almost seven years in the US Army, which had a key influence on his entrepreneurial journey. Having recently been named the EY Entrepreneur of the Year in the Pacific Northwest region, Allen shares some of his career insights and advice.

Jordan Allen, CEO, Stay Alfred
Jordan Allen, Founder & CEO of Stay Alfred, with wife Nancy Allen.

Click.: What were the key moments in your career that defined your position now?

Allen: I had some pretty wild jobs growing up, from a milkman to a repo man. I worked as a butcher in high school. My first career was the Army, which I joined after college. I was able to attend Airborne and Ranger schools, and served in both Iraq and Afghanistan. That was critical for my success as an entrepreneur trying to storm the beach.

[At Stay Alfred] Feedback from guests and employees has been absolutely critical. When you create an open culture and allow your employees to speak up when things need to get fixed, surprise, they get fixed.

Click.: What has been your major success?

Allen: Our biggest success is maintaining and living by our values. The 6 H's: happy, humble, honest, hungry, high performing and H-loyal [sic]. They have never let us down, and those that have them succeed.

Click.: What have been the challenges (and how did you learn from them)?

Allen: Oh, the challenges. Competition, regulatory, the pursuit of perfection and never hitting it. We have to make a concerted effort to bring up all the good we do along with the items that need fixing.

Click.: What do you wish you’d known at the start of your career?

Allen: If I had more industry experience, or put a plan together, we never would have got off the ground. I think understanding the various financing options out there would have helped.

Click.: What has been the most surprising moment of your career?

Allen: The thing that continues to surprise me is how our team rallies behind each other when needed. They are simply awesome at this and it gives us the confidence to achieve anything put in front of us.

Click.: Did you have anyone that mentored or inspired you?

Allen: Tons of folks. Tom Simpson, a very knowledgable investor. Jon Wood and Jeff Elowe, the masters of real estate. Tim Barash, the master of growth and gas pedal. They are all fearless leaders who inspire confidence.

Click.: What one piece of advice would you have for someone starting out in the travel industry?

Allen: Make sure you have intestinal fortitude, and don't wait for perfection to come along.


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  • Jordan Allen is CEO of Stay Alfred,  a serviced-apartments start-up with over 25,000 properties in 33 US locations
  • Prior to entering the travel industry, Allen worked for the US Army, serving in Afghanistan and Iraq
  • He recently won the EY Entrepreneur of the Year in the Pacific Northwest region in the consumer service category