Kassandra Rose – Founder of Rent My Way

Stop trying to convince people of your worth. Just be on the lookout for the believers — they are out there.

Kassandra Rose is a successful entrepreneur living outside Seattle. She founded Rent My Way after the real estate housing crash left countless uprooted homeowners wondering where their next homes would be. Hearing their stories compelled her to find solutions using the untapped potential of rental properties. Her brainstorm resulted in a new online management tool for landlords, property managers, and renters. Rent My Way assists all parties involved in matching inventory to client needs. A salesperson at heart, Kass has been active in businesses such as auto sales and real estate, using these opportunities to study tens of thousands of people actively making buying decisions. By her mid-20s, she was already a proven businesswoman; now, as an author, she wants to share her knowledge and pass it forward.

Kass believes in a balanced life, falling deeper in love with her two sons, and diving into adventure with her romantic partner and his son, along with Ophelia, their new puppy. At any given time, you will find her traveling the world, always living in the moment, and totally immersing herself in foreign cultures, exotic foods, spiritual arts, and music. She believes life is an endless adventure of self-discovery, self-actualization, and constant evolution. Helping others navigate the path of not-knowing to all-knowing is one of her true joys.

Where did the idea for Rent My Way come from?

I own a property management company, RentLucky, that I built from the ground up. My team and I have leased thousands of vacant homes in Washington, and we currently manage hundreds for only $99 a month per door. I kept thinking, “There has to be a better way to get my job done, but the technology platforms are mediocre or only do part of the job.” We operate on nearly a dozen platforms to run our company. These platforms do not talk to one another, so we are constantly doing double and triple data entry. The biggest piece that has been missing in the leasing life cycle is a connection through authentic communication and accountability.

With Rent My Way, we hoped to bridge the gap and streamline the process for all parties involved, not just the property managers and landlords. Our secret sauce is that we focus on empowering the renter, which in turn creates better synergy with property managers and landlords. Our goal is to create the largest pool of prequalified renters in America.

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

If I can go from 100 emails in my inbox to less than 30, I call it a success! I like forward motion. As long as all the wheels are in motion, I’m pleased.

How do you bring ideas to life?

I jump! I collaborate. I drive myself crazy until I can find a way to make it happen.

What’s one trend that really excites you?

Shared economy — people being able to work for themselves and share their talents with the world. I love the authentic movement that’s occurring. I love people who are uniquely themselves, fully supported, and feeling less discouragement than I was exposed to on my way up.

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

I take risks.

I am not afraid to push an industry that many believe should stay the same.

I’m willing to take a bullet for what is right and eliminate negative forces working against people.

I believe humans are the commodity, not just the product. Treat people well, and the money will follow.

What advice would you give your younger self?

Stop trying to convince people of your worth. Just be on the lookout for the believers — they are out there. If you are pitching, selling, and begging for attention, you are barking up the wrong tree. Also, most people who reject you are actually in no position to help. They may make you think it’s because your idea is weak or you’re not ready, but the truth is they just don’t “get it” or don’t have the resources or ability to commit. So don’t be fooled!

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

I have the right to say what I want when I want and often suffer the consequences. I believe most people like to play it safe or play all sides of the field. I like to be bold, authentic, and true to myself.

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

Practice being a mind Jedi. Learn to flow in and out of awareness without attaching judgment or expectations. Get out of your storytelling, and simply create new good vibration experiences.

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

I built a tribe. Finding people who resonate with you and have similar drive, commitment, and desires is just as hard in business as it is in finding love. Don’t give up. Good people are out there, and they are coming — you will attract them. It all takes time. So be patient while you ebb and flow through good and bad energies.

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

Trusting people based on their word and believing them to be something reputable before they displayed any evidence of it. Bad hires, bad associates, bad vendors, dishonest partners, and dishonest advice can cost a lot of time and money.

But, ultimately, you will always grow from the experience. So move on, and be on the lookout. Once you find someone you think may be a good fit, put her on a sustainability test, and watch her for inconsistencies for a minimum of 90 days.

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

Skydiving. You learn a lot about yourself in those 55 seconds of free fall. There is freedom on the other side of fear.

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

BombBomb video emails. It allows us to send personal messages to people to create a deeper connection. Plus, you don’t have to type out all your thoughts. Turn on the video, be authentically yourself, and make the end user smile! It’s a super easy and fun way to connect.

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

The Lean Startup” by Eric Ries. Build it, test it, change it. Repeat. Gone are the days of blowing through money and finding out the hard way that no one actually wanted your product.

What is your favorite quote?

“When someone shows you who they are, believe them.” — Maya Angelou

“You’ve had the power all along.” — Glenda the Good Witch

“If you haven’t anything nice to say, come sit next to me.” — Alice Roosevelt Longworth

“When it feels scary to jump, that is exactly when you jump. Otherwise, you end up staying in the same place your whole life, and that I can’t do.” — J. C. Chandor

“I defend those who are unable to defend themselves.” — Diana Prince (aka Wonder Woman)

Lessons Learned

  • Collaboration, regardless of circumstance, is key.
  • Empower your target audience.
  • Take risks, and always stand up for what is right.
  • Humans are the commodity, not the product.


Kassandra Rose on LinkedIn:
Rent My Way on Twitter: @RentMyWay
Rent My Way on Instagram: