Kerry Kirby

Founder of 365 Connect

Kerry W. Kirby is an American entrepreneur, software designer, philanthropist, and the founder of 365 Connect, an award-winning technology firm within the multifamily housing industry. Over the course of his career, Kerry has been the recipient of an array of highly acclaimed awards, including the esteemed Louisiana Governor’s Technology Award. He has been named to the Silicon Bayou 100 List of most influential entrepreneurs for nine consecutive years and has received a prestigious Titan Entrepreneur Award for his technological achievements.

An acclaimed speaker, author, and award-winning podcaster, Kerry has been a guest lecturer, presenter, and panelist at numerous universities, conferences, and events. He has been featured on the BBC Digital Planet program, NPR News, and various other media platforms and outlets. Kerry has contributed to an array of articles and studies on the convergence of technology in the rental housing industry, in addition to co-hosting an award-winning webcast series, which has reached over one-million listeners from around the world.

Kerry serves on the Board of Advisors of Rainbow, a national nonprofit organization that provides service-enriched housing programs for affordable housing communities across the country, and also serves on the Board of Advisors of the Multifamily Women’s Summit, an event that allows women to strengthen their expertise, influence, and professional network in the multifamily housing industry. He is Chair of Technology Initiative for the Multifamily Innovation Advisory Council, a private, members only group focused on assisting owners and operators of multifamily communities by reducing risks associated with vetting new technologies and implementations.

Kerry and his wife Melinda are highly recognized fixtures in the philanthropic community and were recently acknowledged with a global Communitas Award for their charitable initiatives. This award further established the couple’s dedication to educational, healthcare, and equality programs that focus on accelerating progress for all people.

Where did the idea for 365 Connect come from?

I know the multifamily housing industry from the ground up. Prior to founding 365 Connect, I developed apartment communities across the Southern United States. While developing a large apartment community, I was thinking about new ways to connect people looking for an apartment. The internet was emerging at that time, and it seemed like a fresh approach to take. My thinking was, I’d like to connect people to their community no matter what day of the week, what time of day, and be accessible every day of the year, hence the inspiration for the company’s name.

What does your typical day look like and how do you make it productive?

My typical day starts between three and four in the morning, I like starting early, that’s when I’m at my best and most creative. I start by checking to ensure our platform systems are performing optimally. From there, I get ready, head into the office, and consult my daily list of tasks. I have my priority project always on top of the list and depending on what the rest of the list looks like, that is where I start and get as much done as I can before any of my team pulls on me for other projects.

How do you bring ideas to life?

I installed a giant whiteboard when we built our office, I always make use of it whenever a new idea comes up. I take all new ideas to my product team to make sure my vision fits inside our roadmap. We often make an array of rough sketches on the whiteboard, but it’s those hand drawn versions we are most proud of, as it symbolizes the rawness of the evolution of products. We are in the problem-solving business, so we are always seeking a solution that technology can solve. For example, sending a lease to a renter has proven difficult considering staffing shortages our customers are having, but we found an answer to that with technology. Regardless of whether our ideas work, or we have to scrap them, the process from whiteboard to a final product is fluid, and it can move at a pretty interesting pace trying to flush it out.

What’s one trend that excites you?

Currently, it’s automation. I’m very excited about figuring out how to automate more tasks that people do daily, because I think many businesses underutilize people with redundant tasks that we can use technology to accomplish. I have been learning all I can about self-driving vehicles. Some people don’t feel that they’re safe because there isn’t a person behind the wheel. But when you look at the technology involved, it always drives the speed limit, stays inside the lanes, and keeps a safe distance from other vehicles through an array of built-in sensors feeding information back to its software system. It makes perfect sense how automated vehicles do not have the same limitations or safety risks of vehicles piloted by humans. By taking advantage of automation technology and using it to do the redundant daily tasks that can be time consuming or tedious for our staff, we can repurpose people to roles that require more critical thinking. Technology is great, and automation can certainly help meet some of the challenges we are facing today.

What is one habit of yours that makes you more productive as an entrepreneur?

For me, it’s staying organized with everything that I do. I rewrite my task list every day because it keeps it fresh and on my mind. I’m a firm believer that, if you stay on top of your priorities, things will work out for you in the long run. I make sure to keep up my reminders and allow myself the time to focus on the business, its products, and be available to our team to work through any problems they may encounter.

What advice would you give your younger self?

Learn all that you can. Everyone has some advice to give, you might not use it at that moment, but don’t forget it, because you may need it later in life. Things will always change, learn to take the good with the bad. It is how you react to things that will determine your success in life. The saying “It is not how many times you get knocked down, it is how many times you get back up,” will ring true in everything you do. And, most importantly, don’t worry too much about things that don’t work out. You can’t move forward if you are always looking back, learn from your mistakes and move on.

Tell us something that’s true that almost nobody agrees with you on.

I would say there is always someone that will agree with you regarding something being true or not – so that is a hard question to answer.  But what I do believe in that maybe others will not, is that karma is a real thing. I believe that if you put good into the universe, good things will come back to you.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

There are a few things that work for me. First, I find inspiration in small things, it could be something I read, saw on the news, or remembered in a movie. There is a saying I operate under, “Rest if you must, but never quit.” If you believe in something, never give up and never give in. Find your inspiration and pull on it when you need it. Beyond that, I would suggest to always be on-time, be prepared for the unexpected, be passionate about what you do, and of course, make a list, keep it fluid, but execute something on it daily.

What is one strategy that has helped you grow your business?

Never stop looking for a way to resolve a problem with what you do. Businesses of all sizes have challenges, and they are looking for a solution to ease those pain points. In my case, I’m always looking for a way to resolve problems with technology, be it through efficiency, scale, or removing redundant tasks from operations. That strategy has greatly helped our business grow over time, we see opportunity in making things work, which others deem too complex. It has enabled us to get a seat at the table when businesses need a solution to a challenge they face.

What is one failure you had as an entrepreneur, and how did you overcome it?

The miscalculation of the adoption of tech in my industry. When I first started, the implementation of technology was taking place at a slow rate, I thought I would build some technology-based solutions and they would take off like a rocket ship, but the process took longer than I thought, and it required a bigger commitment than I originally calculated. I had to also take on the role of an educator and advocate for people to understand the benefits of our products. On the other side of that, we overcame the slow adoption cycle by sticking to our vision, adjusting our marketing strategy, and taking a fearless approach to changing an industry.

What is one business idea that you’re willing to give away to our readers?

All my current ideas are centered around automating things, since I see that as a solution to so many problems businesses are facing today. If I were a new entrepreneur, I would look at how people are interacting with things that could conceivably be automated. I would focus on a way to use automation to help supplement the workforce and better utilize people. If you look at workforce demographic data, we will need digital workers across all industries well into the foreseeable future.

What is the best $100 you recently spent? What and why?

The best hundred dollars I spent recently would be taking my wife out on a date night. I love getting away from everything and spending quality time with her – it is my favorite thing in the world.

What is one piece of software or a web service that helps you be productive?

Microsoft has done some amazing things with their Teams product. It helps keep me connected with our entire team, no matter where they are. It provides phone, chat messaging, video teleconferencing, calendar syncing, and file access in one package. I can message, call, or screenshare with any of our team members, whether they are in our main office or at one of our global locations on the other side of the world.

What is the one book that you recommend our community should read and why?

Start With Why by Simon Sinek. It talks about why some people and organizations are more innovative, influential, and profitable than others. It is great inspiration for any entrepreneur and helps lay the groundwork for what is possible if you think differently about how people connect with products and services by simply understanding the “Why” behind them.

What is your favorite quote?

“Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing you can’t do is ignore them. Because they change things. They push the human race forward. And while some may see them as the crazy people who are crazy enough to think they can change the world, they are the ones who do.”  – Steve Jobs

Key Learnings:

  • Give yourself the time and space to be creative.
  • Treat all people the best that you can, we are all created equal.
  • Never stop chasing your dreams, one day you will catch them.