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Launching a Roommate-Matching Site for Women 50+: Karen’s Story

Published on 02/12/2018

After a midlife divorce, a great cohabitating experience would convince Karen to quit her boring job and devote herself to creating Roommates4Boomers.


Tell us a little about your background.
I was born in Atlanta, Georgia. At the age of three, I lost my mother to breast cancer—a devastating loss. My father was abusive to me and my two older sisters. He re-married six months later to a woman who did her best with her step kids—until she had two children of her own. My sisters and I became outsiders during many turbulent years. Having said that, I developed a resiliency and a can-do attitude that have served me well for the rest of my life.

I left home when I was 16 and moved in with a dear friend whose family became mine. I worked during the day as a secretary in an investment banking firm and finished high school at night. I then left for New Orleans to begin my new life, which was in fact the best thing I ever did. Fortunately, my high school counselor—one of many people who has helped me with challenges in my life—lent me $300 for the move, which I did repay, even through it took forever. After waitressing and going to Europe several times (including living in Afghanistan for four weeks), I applied to college and left the South to attend the University of Oregon for undergraduate school. I returned to New Orleans for an MBA at Tulane University. I am the only member of my family to go to college or graduate school.

After receiving my MBA, I returned to Portland, OR, where I worked as a financial analyst for a utility company and then became an energy consultant for the Department of Energy’s World Bank and US Trade and Development. In this position, I managed the development of a feasibility study for a private power project for Kenya Power and Light in Nairobi, Kenya. While this was one of the most amazing experiences of my professional life, I also had two kids under five years old who needed me. I had also married an attorney in private practice in Portland who felt kids were more important than private power in developing countries and (sadly but also happily) I happened to agree with him.


When did you start to think about making a midlife change?
My children were the highlight of my life during those early years. We raised our kids in a wonderful community of like-minded people who supported each other in all aspects of daily life. Education was important to everyone as were healthy lifestyles and exercise. I mean, you live in Portland for those exact reasons! But, like everyone else with kids, they grow up and you have to move on.  

In my case, moving on meant re-evaluating my life and getting divorced from my husband of 25 years and happily starting all over again. During this time and with the help of a friend, I decided to do something “practical” such as starting a manufacturing business making merchandising displays in China. This is something I knew nothing about but being of entrepreneurial mind, I decided to go for it. For seven years, I made displays in China, had customers from large Fortune 500 companies to small mom-and-pop companies and was bored out of my mind with no real meaning in my life.

With Carol, my first roommate

My living situation was my saving grace: I moved in with a good friend in my wonderful neighborhood and began to have the time of my life. Having a roommate was wonderful. I enjoyed coming home to great company, good wine, and no pressure. But, like many things that change, her daughter came home from college and needed a place to live so I had to find myself a new living situation. Fortunately, as things can happen, I got lucky yet again: A friend’s friend decided to live in Berlin part-time so I moved into his condo and lived happily—until my own son came home from college and needed a place to live. Shit happens. So, I rented a house and have lived there ever since.

When I was sharing housing, many of my women friends saw how happy I was. Most of them are well educated and financially secure but were asking questions like, “How do I find meaning?”, “what’s next for me?”, “What if I get divorced? Who will I live with? Where will I go?” All of those questions that many of us asked in midlife.

Because I wasn’t satisfied with my work life, I began to look into the situation of women and shared housing; my background in business led me to conclude that this was indeed a good opportunity.

What is your next act? What do you love about it?
I am the Founder of Roommates4Boomers. It is a national home share matching service similar to Match.com but for boomer women. These women either have a home to share or need a place to live. The process is very simple. You fill out an online form either as a renter or as an owner and then our algorithm matches you based on your preferences. You can contact potential matches and you only pay once you find a person you think you are compatible with.

We currently have almost 4,000 subscribers all over the country. Most people are very happy with their living situations found on our site. Many subscribers need the money and use home sharing to supplement their income. Living alone can be lonely, so having a roommate is a godsend for many people.

Subscribers come to our site from a variety of sources, like Facebook ads, but most come through using search engine option for home share and roommates and we continue to have new people signing up daily.

Funny thing: I met my partner of now seven years on Match.com, which only convinced me more that these online systems work! 

With my partner, Ken

How supportive were your friends and family?
All of my friends and family were supportive and this is one of the most important things in business. Times will be stressful, the future is unknown, money will be tight, but having a supportive network is essential.


What challenges did you face?
This was the worst part. While I did possess more business savvy than many people in midlife, what I didn’t anticipate was how important social media was to a business like this and how to use it effectively. Using social media to connect renters to owners is a major challenge—or I should say, an opportunity with a huge learning curve. Finding qualified marketing people to help with this was the hardest thing and then evaluating how to spend marketing funds was even harder. For example, do you spend money on a national Facebook marketing campaign or do regional TV/Newspaper advertising? I mean really. This was hard.

With my son and daughter

 What did you learn about yourself through this process?
First, I was so proud of myself about this one. I was told to seek funding from the Venture Capital community in Silicon Valley. This would mean I’d have to sell myself as a midlife entrepreneur trying to get funds from men in a man’s world. I recognized early on that 1) these men want to work with other men their own age and 2) most venture capital people don’t like funding non-technical businesses and funding an “Aging in Place” business venture would be next to impossible. Thankfully, I realized this early on and didn’t waste time pursuing this funding source. So, we self-financed the business through savings.

Second, I also realized how much I like working with people who are trying to find solutions for the challenges faced by people our age. There are many new businesses in this area and I continue to be optimistic about this work. People frequently contact me wanting to do stories on this business and I am asked to join women’s groups all of the time, most having to do about aging. Encore.org is one of my favorite sites. I enjoy the challenge because I understand the importance of the work we do.


Looking back, would you have done anything differently?
Yes. While I was happy with my ability to find the right people to set up the web design and infrastructure in order to make this business run effectively, my understanding of how to utilize social media was seriously lacking. I spent way too much money on things I didn’t understand and I would caution others not to do this if possible.


What advice would you give to women seeking to reinvent in midlife?
Just do it. I mean I hate to borrow that phrase since I am from Portland, where Nike is headquartered, but it is true. Still, midlife reinvention is hard so don’t rush into anything. Talk to as many people in similar situations as you can. I go to yoga classes and find women experiencing similar feelings. I tried a watercolor class but it wasn’t my thing; still, I met other women wondering what their “next step” would be. As I mentioned before, organizations like Encore.org and The Transition Network all have programs and speakers that address these issues. 

At a conference on aging, AARP, Washington DC

What about advice for those interested in launching an Internet-based service?
Find a mentor or partner who has skills you don’t have. Do research and write a business plan. Copy any other business model you can which is relevant and adapt it to your idea. Talk to other business owners. Don’t spend money you don’t have. Make sure you have a support group and then go for it.

Facebook and Google ads are great ways to target boomer women and it can be done very inexpensively. BlogHer is also a good place to learn about social media and what works and what doesn’t. It is also a great place to see what other women are doing.


What about advice on cohabitating later in life?
I think the idea of having a roommate is really scary at first. I encourage people to have coffee, go for hikes, talk about issues such as pets, kids, overnight company, music, money, wine habits, etc. All of those things are deal breakers if not handled correctly.

I also encourage people to try it for a couple of weeks if possible and see how it goes. Just like dating, you get a good feel for a potential roommate fairly quickly and I strongly recommend it. I found my honey on Match.com, but had I not had to move from my first home share situations, I think I would have been very happy staying in either of those shared arrangements.

My daughter and I at the women’s march


What resources do you recommend?
Sharing Housing, A Guidebook to Finding and Keeping Good Housemates by Annamarie Pluhar
My House Our House: Living Far Better for Far Less in a Cooperative Household by Karen M. Bush and Louise S. Machinist
The Art of Possibility: Transforming Professional and Personal Life by Rosamund and Benjamin Zander
Good to Great: Why Some Companies Make the Leap and Others Don’t by Jim Collins

“How to Draft a Roommate Agreement – 13 Steps”

Ted Talks:
“Life’s Third Act” – Jane Fonda
“Why We Do What We Do” – Tony Robbins
“How to Build a Company Where the Best Idea Wins” – Ray Dalio
“The Surprising Science of Happiness” – Dan Gilbert
“Let’s End Ageism” – Ashton Applewhite
“My stroke of insight” – Jill Bolte Taylor
“The Power of Vulnerability” – Brené Brown


Connect with Karen Venable
Email: Karen@roommates4boomers.com
Website: http://roommates4boomers.com/
Facebook: https://facebook.com/Roommates4Boomers


HeleneTStelian Musing
I’m Hélène Stelian, the Midlife Mentor with a passion for facilitating personal development in women 40+. Through my THRIVE Courses, I help introspective, curious, action-oriented women 40+ deepen their journeys of self-discovery and growth—and create their next chapter with courage and intention.



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  1. Rena

    What a terrific idea! So many women I know would love something like this.

  2. Haralee

    Golden Girls goes 21st century! I love it!!

  3. Antonietta

    I loved this idea of a matching website for women, I found it very useful. The women are reenventing again.


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