On Creating A Property Management Software With 55% Revenue Growth YoY

Haley Anastassiou and Chris Cooke
On Creating A Property Management Software With 55% Revenue Growth YoY
from San Francisco, CA, USA
started January 2014
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Become A Property Manager

Hello! My cousin Chris Cooke and I (Haley Anastassiou) are the co-founders of TrueRent, a unique property management software system, targeted to help small to mid-sized property owners run their business. We are here to help the property management community streamline their portfolios by simplifying the process of rent collection, tenant screening, and more.

Our flagship product is our all-inclusive property management software. The software is inclusive of TransUnion Tenant Screening, Free Online Rent Collection, Investment Analytics, Tenant Billing/Scheduling, and more. We also offer a free stand-alone product, TransUnion Tenant Screening system, available with or without a TrueRent account. Our customers range from property managers, landlords, owners, management companies, tenants, and applicants.



What's your backstory and how did you get into entrepreneurship?

Chris and I are cousins and grew up together in the Bay Area. We have always been great friends, and becoming business partners was a very natural transition. Working with one of your closest friends is a privilege, and has helped us grow our business, with our personal and shared investment into the success of the company.

Before TrueRent, I studied Communications at Saint Mary’s College of California, in the pursuit of a career in marketing. After graduation, I worked at a large PR agency, specializing in the digital space.

The first steps of starting a business have no clear roadmap. Starting a business can be overwhelming, to say the least, and to set ourselves up for success we took the time to conceptualize our product. We put ourselves in the shoes of the consumer and made sure we understood every aspect of the software we wanted to create.

Lead in areas you feel confident in, and outsource in areas where you aren’t an expert.

Before TrueRent, Chris was (and still is) in aviation and residential property management. He started investing in duplexes and triplexes in the Bay Area back in the early 2000s. His career as a property owner/manager inspired the creation of TrueRent. As he grew his real estate portfolio he found it harder to keep track of rent payments, work orders, and screening applications. When he looked into finding a system, nothing was available for small to mid-size portfolios, and even the systems targeted towards large-scale management groups weren’t all-inclusive. Every feature was an added cost, and none of the available options had a free ACH payment system. Chris brought on myself to help build the social landscape and create TrueRent’s brand. With my marketing experience and Chris’ business and real estate background, we created TrueRent.

As a real customer of the software we were developing, Chris was able to validate our product and make sure our customers were having a superior user experience. We base our company's success on a happy consumer. We also love hearing from our customers and we reach out to our users to hear about their needs and always encourage feedback. At this time, TrueRent is still privately held. We did not pursue outside funding and have supported our business from the creation.

Take us through your entrepreneurial journey. How did you go from day 1 to today?

The first steps of starting a business have no clear roadmap. Starting a business can be overwhelming, to say the least, and to set ourselves up for success we took the time to conceptualize our product. We put ourselves in the shoes of the consumer and made sure we understood every aspect of the software we wanted to create. With real-life property management experience, we were able to discover not only what we wanted to include in our product, but what was imperative to the success of the product.

Nor Chris or I have a computer science background, so our next step was to secure a great engineering team. With our business and marketing background, we felt confident in leading the business with a strong engineering team by our side. We partnered with an agency based in SF and Bangalore that paired us with an amazing development team. We spent months collaborating with the engineers to understand the product we wanted to build, and went through hundreds of modules. While the engineers built out the software, we worked on building the brand, social media presence, marketing strategy, sales strategy, and customer service foundation. Once we felt confident in the product, business model, and most importantly the software, we launched.

To invest in building a relationship with our team, Chris took the time to travel to Bangalore. To this day, we are working with the same engineers, who understand and support the software.


How are you doing today and what does the future look like?

Year over year, we have increased revenue by 55%. Our expenses had previously netted at roughly the same percentage, but last year our expenses were at a record low with the highest record of revenue. We attribute this to satisfied customers, who retain their software membership and continue to grow their businesses. Additionally, we saw a large growth of new users during the pandemic. Landlords and property owners no longer could conduct business in person. It suddenly became unsafe to collect rent checks or go meet with an applicant. TrueRent showcased itself as a safe online solution. Online property management software became more enticing, safe, and efficient to our audience, which helped user growth, and has continued to grow our database of users.

We are operating with the original team today, but have undergone a large software upgrade in the last two years. We redesigned the software in 2019 to make the software more user-friendly and up to date. It was important for us to make the software easy to use, and easy to understand. While we have some landlords with 100 units, we have other users with 1 unit. We want the software to fit the model of the user, and attain the capabilities that they need, while not overwhelming them with what they don't.

In addition to the redesign, we added new features based on user feedback, and our personal experience with the site. We now offer free tenant screening through TransUnion, free online rent collection, and just initiated free next-day ACH funding. We are one of the few, if not only property management software on the market, that offers free next-day funding.

Our operations today greatly focus on customer support, customer retention, new user growth, paid media, and sales/email marketing. We plan to keep expanding our business and reach new user growth records month after month.

Through starting the business, have you learned anything particularly helpful or advantageous?

The biggest challenge in starting your own business is that you simply can’t do it all in a day. One person can’t tackle sales calls, campaign builds, customer service emails, QA testing, etc. in one business day. My biggest lesson in growing our business is to know what you excel in and don’t be too proud to outsource in areas that aren’t your expertise.

For example, I was in marketing for years specializing in digital campaigns in FinTech. I worked directly with the paid media team, but didn’t manage paid media. Through trial and tribulation, we took a financial risk in testing out paid media strategies. Essentially, I was shooting darts in a world where I didn’t specialize. There are experts in all fields, and amazing agencies, and freelancers that will be more effective for your business practice. Lead in areas you feel confident in, and outsource in areas where you aren’t an expert.

It’s also easy to get discouraged when owning and operating your own business. Every entrepreneur will receive a disheartening customer support email, experience a glitch in the software, get hung up on by a prospect. Have grace with yourself in running a business, and know that each element of your business needs to be tested in order to succeed. Every mistake, or “failure” leads to a better business model and an overall superior user experience.

As far as outside influences, or trends, our business can attribute a large amount of success due to the regularity of online payment solutions. When we started our company, Venmo was around, but not nearly as prominent. While we process ACH payments rather than credit cards, the ease of paying people through technology has become customary. Other applications have regulated that process and encouraged users to make their payments online, promoting businesses such as ours.

What platform/tools do you use for your business?

We use many different tools for our business, our favorite being a CRM tool. We use Zendesk to manage our customer support platform, providing email, phone, and chat support to our users. This tool makes it so we don’t miss any support inquiries, and can provide a range of support options to best fit our customers' needs.

What have been the most influential books, podcasts, or other resources?

I frequently listen to the podcast, “How I Built This with Guy Raz - NPR.” Guy Raz interviews CEOs and co-founders of majorly successful businesses on how they got started and where their company currently stands. Hearing these CEOs talk about their small idea that grew into a multi-million and/or billion-dollar corporation is immensely inspiring. I would recommend that any entrepreneur listen in, and note the failures that these leaders experienced. Every entrepreneur will experience hardship, whether that is a small hiccup or a million-dollar mistake, and listening to the way these leaders dealt with these roadblocks has had a great impact on my business. The one underlying message of this podcast is belief in your product, and these CEOs succeeded because they believed in their product, listened to their customers, and fought for the success of their company. Give it a listen, you won't regret it.

Advice for other entrepreneurs who want to get started or are just starting?

When starting, my advice would be to make thoughtful decisions when selecting the right team. It’s easy to quickly make decisions when you have a large overhead or pressure to start making revenue but take time to work with people that understand you and believe in your product. My other piece of advice is to constantly check in with yourself. Why are you running this business? Who are you helping? How can you make the user experience that much better? It's easy to get swallowed by your business and lose track of why you are here. Always emphasize the importance of the user experience, and remind yourself that you built this product to help the consumer, and how are you keeping them in mind through every business decision you make.

Where can we go to learn more?

Haley Anastassiou and Chris Cooke   Founder of TrueRent
Pat Walls,  Founder of Starter Story

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