Lift Your Legacy: Leveraging help from a Higher Power with Casago CEO Steve Schwab and Rabbi Jacob Rupp

“I prayed and told God that I could do more for people with the company than without it. At that moment, while on my knees praying, I had a call from a realtor who wanted to buy a condo I had bought years ago. I mentioned that I had been trying to sell it for […]

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“I prayed and told God that I could do more for people with the company than without it. At that moment, while on my knees praying, I had a call from a realtor who wanted to buy a condo I had bought years ago. I mentioned that I had been trying to sell it for nearly three years and couldn’t get anyone to even make a lowball offer.”

Steve Schwab is the founder and CEO of Casago, a property management and vacation rental company headquartered in Scottsdale, Arizona. Steve, a 20-year industry veteran and self-described “Property Management Nerd,” founded the company after creating a simple software solution to help manage property bookings, maintenance, payments, and more. Casago has 2,300 units that they manage or rent in a dozen communities across the USA and Mexico, and has served more than 3.2 million guests to date.

Thank you so much for doing this with us! What is your “backstory”? After serving in the military as a US Army Airborne Ranger, I went to New Mexico State University and earned my bachelor’s degree in criminal justice. After graduation, I took some time off and went to Puerto Peñasco, Mexico for the summer. Instead of spending all my time on the beach, I worked odd jobs for a couple who owned a small beach home rental company. When the husband passed away a short time later, I bought the company. The business was in disarray and had lost half of the properties in its inventory, but I had innovative ideas to build the business. I started by finding the old client list and called each and every homeowner and asked them to come back. Most of them did.

After competing with the largest company in town for nearly a year, I caught a break. On Dec 13, 2003, my competition, Rocky Point Management, left town in the middle of the night. The next day, I got a call from the company’s largest client who asked me to take over the account! It was a mess. Many of the homeowners’ bills had not even been paid and we couldn’t get ahold of them. So, we took our own funds and paid their bills. To our surprise, word got out that we had helped these homeowners even though they were still technically our competitor’s clients. After that, our reputation grew and so did my passion for helping homeowners.

Can you share the funniest or most interesting story that happened to you since you began leading your company? 

A funny story that taught me a good lesson about people happened during the early years of Casago. My general manager handed out a drink ticket to each employee to use at the office Christmas party that night. Two of my employees realized you could photo copy the drink tickets on the color printer and make more. That night drinks flowed and there were plenty of tickets to go around. The next day when the bill came, the restaurant informed us that they had more tickets turned in than what we actually purchased. I was furious when I found out what happened! I called a mentor of mine named Mike McCabe and he gave me perspective on the human element of business. As a result, I didn’t fire the responsible employees, and they both became key employees for more than 10 years! In fact, one is still with me 17 years later. Sometimes forgiveness and being magnanimous with your team can create deep loyalties.

What was your biggest challenge to date either personally or professionally and how did you overcome it?

The biggest challenge I have had professionally was overcoming the economic crash that took hold in 2008. I had an 87 percent drop in revenue in one year with 200 employees who depended on me. I sold most of my assets and cashed in all of my retirement to make payroll, then convinced my vendors to give me an extension to pay the bills. I can remember having chest pains from the anxiety that I was going to let everyone down. My CFO told me I would be out of cash in two weeks unless I came up with a miracle, and he tried to convince me multiple times to shut the company down and walk away. But I told him to have faith.

I prayed and told God that I could do more for people with the company than without it. At that moment, while on my knees praying, I had a call from a realtor who wanted to buy a condo I had bought years ago. I mentioned that I had been trying to sell it for nearly three years and couldn’t get anyone to even make a lowball offer. He asked if I would take 235K — exactly what I was asking for! I quickly agreed and questioned if it could close in two weeks. He called back and said yes in fact they could. That money funded into my bank account less than 4 hours before I had to make payroll and my company was saved. My lesson was to always keep faith in God, never quit, be resourceful and never listen to the naysayers.

What does leadership mean to you and how do you best inspire others to lead?

Leadership is the ability to bring people to a place where they want to follow you, not feel like they are forced to follow you. This takes investing in your team personally. They must know you’re not only going to hold them accountable and drive them to be better, but also look out for them when they are struggling. It’s not transactional, it’s a relationship. Just like many relationships, you must look at each person and decide if this is someone you want in your life and around your work family. If they are not a good fit, you got to let them go sooner than later. You can’t fake caring about someone.

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?

I have been blessed with a loyal work family and a community of customers in Puerto Peñasco (Rocky Point) that have been with me through thick and thin. They have given me chances to prove myself and guided me when I needed it. My team was always there for me — even in dark times during the recession.

Was it difficult to fit your life into your business/career and how did you do that?

Because of the extensive travel associated with my work, balance has to be constantly taken into account. I learned to fly an airplane, focused on my calendar and set days aside for my personal life that were not negotiable. I also found that traveling to new places to explore is a pressure relief valve for me.

The struggle with growth is that it gets harder as your company gets bigger until you can afford the kind of talent that takes the heavy burden off of you. To see continued growth year after year, you must grow through the pain and hire the right talent to support your current and future growth.

Did you find that as your success grew it became more difficult to focus on the other areas of your life?

Personal relationships can suffer when you work long hours and are traveling for work. The real key is to find someone who you are aligned with to be part of your life. I found a wife who loves adventure, understands my workload and supports me. It’s been one of the happiest changes to my life and my work, and it has made me much more of an effective leader.

Can you share five pieces of advice to other leaders about how to achieve the best balance between work and personal life?

  1. Organize your time and make time to get away, then buy a plane ticket so you can’t get out of it.
  2. Invest in your body, your mind and your soul every day for 1 to 2 hours a day. It will change your life.
  3. Force your employees to turn off their phones and rest. This will let you rest also and keep all of you from burning out.
  4. Sleep. We all want to take pride in our lack of sleep because we think it shows how hard we are working. But this dulls your mental edge. You’re a mammal, mammals sleep a lot.
  5. BUILD A COMPETENT TEAM YOU LIKE AND TRUST! This will save you an infinite amount of time and stress.

What gives you the greatest sense of accomplishment and pride?

Watching my son grow into a man. He’s on a journey to becoming a very special man and it gives me immense pride to witness his transformation.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Realistically, I would love to build housing for the poor by processing recyclable materials that are sourced locally. I’ve been working on this idea for a while now and I am excited for its potential.

What is the best way for people to connect with you on social media?

About the author: Jacob Rupp is a coach, author, speaker, podcaster, and rabbi. He is the founder of Lift Your Legacy, a community that helps people live a more authentic life. He has a regular, syndicated column that appears in ThriveGlobal and Medium magazine. To learn more about him or to listen to the Lift Your Legacy podcast, search iTunes or visit his site:

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