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Cliff and Angela Osbon of Office Evolution: “Time Together ”

Time Together — We enjoy spending time together. We travel (when possible!) and enjoy getaways to the mountains, the beach or other fun destinations we love, like New Orleans and Las Vegas. We can’t wait to travel internationally again (soon hopefully!). We also love live music — both small venues and concerts. As a part of our series about […]

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Time Together — We enjoy spending time together. We travel (when possible!) and enjoy getaways to the mountains, the beach or other fun destinations we love, like New Orleans and Las Vegas. We can’t wait to travel internationally again (soon hopefully!). We also love live music — both small venues and concerts.


As a part of our series about lessons from Thriving Power Couples, I had the pleasure of interviewing Angela and Cliff Osbon.

Angela and Cliff Osbon, co-owners of Office Evolution of Flowood, are longtime Jackson area residents and serial entrepreneurs. They have four children and one grandson. After their careers in legal and health care professions, they are excited to be participating in the growing flexible workspace industry and thrilled to be supporting other dreamers, risk-takers and doers in their community.


Thank you so much for doing this with us! Can you tell us a story about what brought you two to your respective career paths?

In the Spring of 2019, Cliff saw a segment on the CBS Sunday Morning Show about the growth of coworking and flexible workspace providers. Having seen fractional ownership of various other things — like Uber and Lyft for cars, or like AirBnB or VRBO for vacation homes — we thought that business model, which is similar to fractional ownership, offered a lot to entrepreneurs like us. That set us off to investigate various franchises that would align with our lifestyle. Ultimately, we found Office Evolution and attended Office Evolution’s Discovery Day. We saw an opportunity to offer close-to-home, flexible workspace to the businesses in the greater Jackson area.

Can you share the most interesting story that happened to you since you two got married?

After negotiating the sale of a business in 2017 that Cliff had co-founded in 2002, we thought that we were entering into a period where things would be slowing down. But nothing could be further from the truth. After our marriage in 2016, it was just a few short months before we learned that we were to become grandparents! Soon after that amazing addition to the family arrived, we completed the sale of the previous company and rapidly participated in the launch of three more businesses with a fourth coming soon! As entrepreneurs, we have many stories, so it’s a little hard to nail down just one “most interesting” story!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Well, opening in early 2020 at the front end of a global pandemic might count as a mistake! Or, better yet, a challenge that we were up to tackling. We pushed forward and became part of Office Evolution’s Ohana — Hawaiian for family. Even though we could not participate in face-to-face events like we normally would have, we, along with our Business Center Manager, sought every available virtual opportunity to engage with the community and prospective member clients. We even hosted virtual conferences in our business center, where the leaders and presenters could still socially distance but also present to hundreds or thousands of people via a web conference in real time. We learned to be innovative and think about creative win-win ways to support our members.

What do you think makes your company stand out? Can you share a story?

We are entrepreneurs serving other entrepreneurs. We are not successful unless our members are successful. It is in our DNA to support our members as they move forward during this pandemic. Our business center stayed open during the pandemic to ensure we were providing the support our members needed while following safety protocols. We hit the ground running every day, with this mission in mind.

Are you working on any exciting new projects now? How do you think that will help people?

We are partnering with local businesses that work virtually with others during the pandemic and beyond. We have clients in areas like telemedicine and life coaching that can perform their services from our state-of-the-art facility.

What advice would you give to other CEOs or founders to help their employees to thrive?

Listen to your team. If you have identified and engaged good team members and if you’ve equipped them with the technology and resources they need, they are usually more “client-facing” than you. Actively solicit their input and use it! Empowering them to make decisions is good for everyone.

How do you define “Leadership”?

Peter Drucker defined Leadership this way: “Leadership is lifting a person’s vision to high sights, the raising of a person’s performance to a higher standard, the building of a personality beyond its normal limitations”. We think that’s a great definition!

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 about that?

Cliff: I have a background in pharmacy. I attended pharmacy school and practiced in many non-traditional settings that used my pharmacy education, working with clients like pharmaceutical manufacturers, specialty pharmacies and health plans that provided pharmacy benefits to their members. I’m grateful for the two brothers that owned a local drugstore where I worked after classes in pharmacy school. “Johnny and Joe Sampognaro really taught me a lot about business and a lot about people. I always remember them fondly.”

Angela: I have a background as a paralegal. I have worked in multiple legal settings such as private practice firms, with the U.S. Department of Justice and for Entergy (Legal) Services. I am most grateful, both professionally and personally, to the late Frank M. Youngblood, Sr., who was my first employer in the area of law. His hard work, integrity and compassion with people was admirable. He was also an excellent “teacher” of the law.

How have you used your success to bring goodness to the world?

We have a real soft spot for the vulnerable. Some faith traditions talk about the need to help “widows and orphans”, meaning those who cannot help themselves. We currently support organizations that seek to provide food, shelter, medication and education for children and those who seek to rescue boys and girls from sexual trafficking. Recently, we worked to support a constitutional amendment passed in our state that would make medical marijuana legal for those who are sick, suffering or dying. Additionally, we support a local ministry that is highly active in serving inner city youth and their families.

What are the “5 Things You Need To Thrive As A Couple”? Please share a story or example for each.

  1. Time Together — We enjoy spending time together. We travel (when possible!) and enjoy getaways to the mountains, the beach or other fun destinations we love, like New Orleans and Las Vegas. We can’t wait to travel internationally again (soon hopefully!). We also love live music — both small venues and concerts.
  2. Time with Family — We have a blended family of four adult (and “almost adult”) children and one grandchild. With the kiddos living across several states, getting everyone together can be a challenge — and an adventure! Holidays and summer trips to the mountains keep everyone anticipating the next get together!
  3. Time Alone — We feel that “alone time” for exercise, self-reflection, reading, music and relaxation nurture the body mind and spirit.
  4. Time with Friends — With an active social circle, we share good times with a group of long-term friends regularly.
  5. Time to Grow — Growing a business (or three, as is currently the case) helps us learn together and continue to grow together while meeting needs and serving others.

You are people 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?

Considering the world today, we feel that inspiring others to treat one another with more kindness, less hostility and more grace and compassion would be a benefit that would trickle into every part of our personal and professional lives. We love to encourage people to be less reactionary and more thoughtful and slower to respond to stresses and agitations in their lives.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Cliff: my favorite verse, was written about 2,500 years ago by a man name Micah in a small village called Moresheth in the Middle East. Micah wrote, “He has shown you what is good and what does God require of you? To act justly, to love mercy and to walk humbly with God.” I believe that people of all faiths (or none) can hopefully agree that to act justly, to be merciful and to be humble is a lifestyle that could be good for us all.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

Cliff: I would love to meet American novelist James Lee Burke. Burke is America’s best living novelist. I’d be happy to meet him anywhere in the country for breakfast and coffee! I’ve read everything that Burke has published — forty novels or collections of short stories so far!

How can our readers follow you online?

We both maintain various social media accounts but our LinkedIn accounts are best:

https://www.linkedin.com/in/angela-reeder-osbon-048849163/ (Angela)

and

https://www.linkedin.com/in/cliff-osbon-94084a5/ (Cliff).

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