Meet The Disruptors: Jonathan Kite Of Rent Ready On The Five Things You Need To Shake Up Your Industry

An Interview With Fotis Georgiadis

Fotis Georgiadis
Authority Magazine


Never go it alone, always start a business with co-founders to share the emotional burden of what you are trying to accomplish. I have been incredibly fortunate to have started a business not only with one cofounder, but with two. Having someone to share the wins and celebrate with, but also to share the pains and difficult decisions with is paramount to your survival. Running a company is incredibly lonely — if you have the chance to share that with someone else, you would be foolish not to!

As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Jonathan Kite, the CEO of Rent Ready.

Jonathan Kite is the CEO and Co-Founder of Rent Ready, a technology company that uses an integrated services portal to deliver an end-to-end make-ready service for apartment communities. Based in Charlotte, NC, the startup introduces a modern day solution to an age-old apartment industry problem with the first automated turn board in the marketplace, connecting community staff with service professionals to schedule work orders for all turn services including painting, cleaning, wall repairs, tub/counter resurfacing and more.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I grew up in Charlotte, NC where Rent Ready is currently headquartered. Even as a child, I was enamored with the process of creating and I got into technology because I was obsessed with its use as a creative problem-solving tool. Immediately out of college, I started my career at Microsoft where I held different roles that allowed me to interact with hundreds of different companies, learning how they developed, supported, and evolved software to solve business problems. In my last role at Microsoft, I had an incredible opportunity to work on a team with advanced internal access to cloud technologies that would eventually become Microsoft Azure.

It was an experience that demonstrated first hand how quickly cloud first technologies could enable the transformation of a business idea to execution at a rate never seen before. So when approached by my two other co-founders with the idea of Rent Ready, I knew the time was right to leverage my experiences at Microsoft to help build a company. Ryan McMillan, my first co-founder, worked directly in the multifamily industry, observing and living the challenges of getting vacant units ready for new residents by working with fragmented labor sourced through local vendors without the aid of technology to facilitate the apartment turnover; a highly sequenced and timed multi-stage delivery that must be completed in order to move in new residents. Will, my second co-founder, came from a background in finance and private equity and quickly identified the enormity of market opportunity the turnover process represents in the multifamily industry.

Each of us came at solving this problem from unique backgrounds, a keen observation of the challenge facing the multi-family industry, the business background to identify a go to market plan, and the technology expertise to build and scale a national company.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

The apartment industry prepares recently vacated units for new residents in an entirely manual or analog manner. Apartment managers find and source local vendor relationships across 4–5 different vendors who each provide a unique service that is required in the sequenced process for getting a unit ready for a new resident. They are responsible for coordinating the scheduling of services in that sequence using traditional communication methods. It’s not uncommon for an onsite apartment manager to call, text or email their orders across their 4–5 vendor relationships each time a resident moves out and a turnover is triggered — tracking availability, confirmation and service progress manually on a dry erase board or excel spreadsheet.

This is a time consuming process that eats up anywhere from 4–6 hours of a manager’s time on a weekly basis. Rent Ready is applying technology to help solve that problem by providing apartment managers access to web and mobile applications, connected to a network of skilled vendors also utilizing mobile technology to seamlessly connect the two together. With a few clicks, apartment managers can specify their desired service profile, sequence, and timing requirements, and Rent Ready will automate the rest of the process, suggesting service availability dates, timing, and automatically scheduling work against its network of service providers all with one click. Service providers receive real time notifications of work assignment, and interact with technology that allows managers to gain real-time insight into work progress and timing.

This is a radically different and simplified approach that uses mobile technology to help remove friction and improve the process for both apartments seeking work to be performed, and service professionals providing that work to apartments.

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?

Rent Ready is designed to help make the lives of onsite managers easier, and the technology that Rent Ready provides apartments helps connect them to a marketplace or network of service providers. Building out a network of service providers has been an iterative journey of discovery over the years and one full of lessons. Validating a prospective service providers skill set has always been difficult, and in the early years, it took us time to realize that almost everyone will tell you they have the ability to perform a skill set.

Painting is a great example where if you ask most people if they know how to paint, you will almost always emphatically be told “yes” only to have that individual show up to paint an apartment with a single paintbrush. Early on, that happened more times than I care to admit and was a great lesson in adopting the “trust but verify” mantra needed to build expertise in assessing skilled trades to service our clients.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

One of the most impactful mentors I ever had was actually my first out of college in my first role at Microsoft. Her name was Ellis, and she was a long-time veteran of Microsoft who had been there for over a decade and served in many roles on many teams. She was an inspiration in helping me to realize that there are things in life that are fundamentally more important than work, which is a lesson I hold true even to this day. She famously helped work for and supported several U.S. Military organizations on behalf of Microsoft and was always great at reminding me of the criticality of what I did on a daily basis.

When things were stressful for me or I felt like the world was falling down around me, she constantly reminded me that there are things in life that are truly critical — like ensuring that software systems are operating and functioning to help in aiding tasks like landing pilots on aircraft carriers, things that truly impact life and safety. Those reminders always helped me put things into context with the problems that I faced, and it’s a lesson I try to repeat to my teams on a constant basis whenever they are feeling stressed in the high paced environment of working for a startup. Yes, helping our customers get units turned is critical to our business and important, but we aren’t landing fighter jets on aircraft carriers and there are no lives at stake.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

You often hear the term “10x” thrown around when thinking about what startups seek to achieve. They are seeking to disrupt an industry by solving a difficult problem by delivering a solution through either new technology or business process that is not just better, but truly 10x better than anything a competitor can offer. You see that every day as companies seek to reduce friction in an industry by providing 10x solutions that make the old way of doing something seem obsolete.

As obsessed with technology as I am, I have always been torn between the new and the old, still loving and preferring the preservation of old experiences that so many new companies have disrupted today. The convenience of streaming music is certainly an example of an experience that is 10x better than consuming music in analog with a CD or record, but as a music enthusiast I still prefer the process of seeking out and collecting music in analog, which is why I continue to collect and have amassed a huge collection of records. While I can’t deny that the experience of streaming music overall is a positive disruption for 90% of the addressable market, it has had a negative impact on the enthusiasm and culture of the remaining 10% of loyal fans who will always prefer the hobby of collection and music appreciation.

Sometimes disruption can be so focused on the tangible measures of an industry; cycle time, cost, convenience, etc that you lose sight of the intangibles of an industry that make it truly unique.

Can you share five of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

1. Take care of the people, the products and the profits in that order — The culture that we built at Rent Ready has always been focused on creating an incredible work opportunity for our employees and putting them first. When the pandemic hit we were singularly focused not only on surviving but preserving as many jobs as possible, even if that meant that all of us had to make a sacrifice to do that — most companies did not make those types of decisions, instead laying off, focusing on profitability first. We took another path, and most of our team stuck with us not only through the toughest of times in the pandemic but all the way back to our eventual return to work.

2. The difference between success and failure is not a combination of brilliant strategic moves, or innovative ideas, it is the willingness to never quit and to continue to grind it out. I was once told that a C+ plan carried out with 100% commitment and execution is infinitely superior to an A+ plan carried out with 80% commitment. There are countless examples within our business of a truly “great idea” not panning out, which can often be a demotivator to those helping to build our business, but we consistently try those failing ideas again and again until they succeed.

3. You only experience 2 emotions running a startup: euphoria and terror. Nothing better highlights this lesson than the challenges of raising capital to continue to survive and grow your business. The agonizing lead up to closing a successful funding round to the sheer bliss of actually signing the documentation to close a round, immediately followed by the realization that you have zero time to celebrate because the expectation of your success has only raised exponentially only helps to highlight how true this statement is.

4. Never go it alone, always start a business with co-founders to share the emotional burden of what you are trying to accomplish. I have been incredibly fortunate to have started a business not only with one cofounder, but with two. Having someone to share the wins and celebrate with, but also to share the pains and difficult decisions with is paramount to your survival. Running a company is incredibly lonely — if you have the chance to share that with someone else, you would be foolish not to!

5. Always ask yourself, what am I not doing that I should be doing? It’s a question I try to ask in each 1:1 I have with employees, especially those I don’t directly manage. Some of our best ideas come from those who help support our customers in the day to day — and simply asking that question, what am I not doing, or what are we not doing that we should be doing almost always sheds light on a new process or business idea that can fundamentally change the business.

We are sure you aren’t done. How are you going to shake things up next?

Rent Ready continues to see the challenges of fragmentation in not only the labor that is provided into the multi-family turn process, but also the advanced acquisition of materials and other services. While we have been predominantly focused on normal turnover services such as painting, cleaning, and carpet cleaning; one missing component is our ability to help apartments facilitate more complex turns that require more in depth services like flooring replacement in a unit that is being made ready for a new resident.

This is a different product offering vs. what Rent Ready traditionally provides, and while apartments have access to much larger nationally relevant service providers offering this service, the same challenges of coordination and incorporation into the larger turn sequence still persist. Rent Ready can help improve that through our technology interface for customers, but can also help provide value to these service providers by building technology that can help these companies improve their business operations and customer interaction too.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

The Hard Thing About Things by Ben Horowtiz is the absolute best book anyone starting a company should read. It’s full of not only inspiration and practical advice but also recognition of the journey you are on starting a company. It’s not a management book full of self-evident observations or recommendations of optimizing an already established or well performing business that completely miss the mark on how you handle the extreme highs and lows you will face. Instead, it highlights the harsh realities you implicitly feel but can’t articulate by pointing out truths like: your emotions are at odds with your logic, and things are hard because you are both doing things and making decisions about things that you have no experience with and there is a high likelihood that no one else does. This has been such an impactful book for me, because it operates more like a soul piercing therapy session than a management book, acknowledging that the way you feel is normal, the challenges you are facing while unique to you, are not unique to starting a business and that things will only continue to get hard, not easier — and if that’s not for you, then you shouldn’t be running a business.

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

“You have to lie down to be a doormat” is a life lesson taught to me at an early age that has always resonated with me. For me, it is what has always sparked my relentlessness, which not only helped me in starting a business but to continue to build that business and overcome the many obstacles we have faced. Oftentimes people are too quick to accept the response of “no,” or resign themselves to accept defeat, be that through bad luck, bad negotiation or a lack of self confidence in pushing back. Advocate for yourself, don’t be shy to ask “why,” when even if you do hear “no” — you deserve to know why so you can constantly improve yourself and get to “yes” the next time you try it again!

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. :-)

I’ve always been obsessed with bicycles as a form of transportation, ever since I was a kid. When I lived in Seattle and worked at Microsoft, I never drove, I biked literally everywhere; to see friends, to grocery shop, or to get to work. Americans often feel like cars are a necessity, and in many cities that aren’t bike-able or don’t have great public transportation that may be true, but it doesn’t have to be. Making decisions about where we live and what we need in our lives are all related, and oftentimes most don’t see that by making trade-offs like not owning a car, many of us can afford to lead different lifestyles like living closer to work.

I wish I could find a way to help inspire and encourage others to adopt a car free lifestyle, to help change the way our cities in America are designed, flow and operate so others can find ways to adopt a more urban and dense way of living led by the bicycle!

How can our readers follow you online?

You can follow me on LinkedIn or the Rent Ready blog here.

This was very inspiring. Thank you so much for joining us!



Fotis Georgiadis
Authority Magazine

Passionate about bringing emerging technologies to the market