Pay It Forward: "Have a Vision With Purpose. A Clearly Defined Plan. And Take Steps To Achieve Your Goals"

"Success takes clarity, consistent action, determination and commitment. It is important to not waste too much energy or attention when you want to give-up. Keep your eye on the prize, stay focused and keep moving," says Deb Cleveland of Small Town Dynasty.

Deb Cleveland, Courtesy photo

Deb Cleveland is the founder & CEO at Small Town Dynasty. Cleveland is an entrepreneur and real estate investor, and she mentors women on how to flip houses and build personal wealth. 

What has been your biggest challenge or obstacle as a woman in your particular role/? How have you overcome those obstacles? At my age and experience, I don’t face some of the challenges I did when I was younger and less experienced. When I was younger, I faced quite a bit of sexual undertones when working with men that had power to make critical decisions. I chose to always handle myself and business in a very professional way. This approach has always served me well. The other challenge is that the guys have a way of hanging out together, which is normal and natural for them. Men are less likely to do this with women in business and women are less likely to do this with other women in business. The way I have overcome this obstacle is by having immaculate follow-up and follow-through, being a person that honors my word and providing A-plus service to my clients.

What about your current role are you most happy with? I love being my own boss and I love the freedom that owning your own business gives you. I tried to retire because that is what we are told to do after you have been successful in your industry and you reach your 60s – this seems to be particularly true for women. I love spending time with my family, but I enjoy doing meaningful work that makes a difference and that is why I started mentoring women through Small Town Dynasty. I now get to work with women like me who have been successful and want to leave a legacy so it is the most fulfilling part of my career. Choosing to come out of retirement and get back into business was a big decision for me. Now, I work at a very different pace, which has made it fun and enjoyable.

What is the best piece of advice you have received that has helped you succeed in your industry? I have received consistent advice throughout my entrepreneurial life about success. The most important counsel has been to have a vision with purpose, create a clearly defined plan, commit and take steps every day to achieve your goals. I have successfully applied this advice to many areas of my life. The advice I would give to the next generation is to be in the life that has been given to you. Life isn’t lived through text messaging or staring at a computer screen.


Would you advise your son or daughter to begin a career in CRE? Yes, I have advised my son and younger folks to invest in real estate. Unless you were born into a family that owns real estate investments, chances are unlikely that you would be informed about the industry. If you are, it is more about becoming an agent versus an investor. I wasn’t given any advice about becoming a real estate investor. I stumbled into it when I was researching ways to invest money I was making from a small business I owned. I knew I needed to do something other than investing in the traditional ways. I remember how amazed I was at how much passive income and wealth was possible by owning rental income. It seemed so easy and made so much sense.


Please share with us the best lessons learned or a surprising component about your unique journey. I am a planner. I planned to retire financially free at the age of 48 – so I did. What I wasn’t prepared for was how retirement wasn’t for me. What I learned from this experience was how much I enjoy business, making a contribution, having fun, being in the community, making a difference and money too as a real estate investor. I decided to invest in a small Finger Lakes city right after the 2008 crash. I put together a small crew, we dug in and renovated over 87 properties helping this area turn around. I then was approached by several other retirees who wanted to do the same. Our neighborhoods, smaller towns and cities would benefit greatly from having folks that truly care, make the commitment and want to take part in being part of these communities.”

In your opinion, what takeaways did we learn from the COVID-19 crisis? I feel that just like the 2008 crash it was a wake-up call of a different flavor. I feel that mother nature has her way of course correcting. I feel the pandemic truly forced families to look at what is important.”

Commercial real estate has historically been a challenging industry for women. Where would you say commercial real estate needs to improve for women? I feel that there aren’t many women role models in commercial real estate. I also feel that unless women create desire and interest in the industry, men don’t feel that motivated to invite women into the arena. Women tend to only look at the commercial real estate business from the perspective of being an agent, but there are so many other possibilities for women.

How can women better position themselves for success both in general and in your specific area of focus? Get the right information and knowledge you need so you understand if becoming a real estate investor, or any other business endeavor you are considering, is right for you. I take clients through an introductory training called the GPS Foundational Course for Beginners. This gives clients the roadmap they need to start investing. Once they have a clearly defined plan, success is determined by execution, which takes commitment and consistent action.

I used the GPS process each year when I started and then built three multi-million dollar businesses from scratch as a single mother with no education. When you have a roadmap of where you are going and where you want to end up, it is easier to stay on track. Success takes clarity, consistent action, determination and commitment.  It is important to not waste too much energy or attention when you have one of those days, which we all have, where you want to give-up. Keep your eye on the prize, stay focused and keep moving.”

What, in particular, can women bring to the table as the industry continues to grapple and come out of the COVID-19 crisis? Women are highly intuitive by nature. Listen and trust this part of yourself.

Find more CRE career advancement tips and inspiring stories from industry leaders in our Pay It Forward series.


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