We’re excited to introduce you to the always interesting and insightful Caroline Leo. We hope you’ll enjoy our conversation with Caroline below.

Caroline, thanks for joining us, excited to have you contributing your stories and insights. Let’s talk legacy – what sort of legacy do you hope to build?

Professionally, I would like to be remembered for community block development efforts made in neglected, overlooked, underserved and forgotten communities. Providing beautiful, designer forward new homes as better rentals as well as 1st time homebuyer opportunities for hardworking people at affordable price points. That we took the extra time and energy to work with potential buyers on credit issues, financial health and wellbeing, and preparedness for the big step of wealth building and future legacy for their families. The commitment to change an entire neighborhood by building 10+ homes on a any given block that creates significant change for the future of that community. To breathe new life into struggling communities that otherwise would fail.

Personally, I would like to be remembered for the passion of rescue for a very misunderstood breed of dogs — Chow Chows and Chow mixes. Those ones who are damaged, injured, senior, shy, terrified, wounded — the ones who are deemed ‘unadoptable’ by most groups and who are 1st to be euthanized in overcrowded shelters.

Caroline, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

At 72 years old, I’ve had many wonderful opportunities to be independent, creative, and inventive. In my 20s, I started as a fashion designer creating beautiful ball gowns and travel clothing for the DC embassy elite.

In my 30s, I went back to college and graduated as an Interior Designer working for high-end clients in and around the DC & metropolitan areas. I had the good fortune of working with several custom home builders as their client liaison providing overall design plans, specialty product design and procurement, management, and on-site visibility during construction.

In 1991 I moved to Baltimore and opened a private studio for design, creating exciting designs for high-end clients in Baltimore, Howard counties, and throughout the city. For more than 20 years, DARE Designs, LLC participated annually in Decorator Showhouses for the Baltimore Symphony, Historic Ellicott City, Harford County Cancer Center, Anne Arundel Hospital Center, and several others to help raise funds for their efforts.

In my 40s, my husband, Leo, and I opened yet another company. We were invited to show and sell exceptional home, garden & gift items at wine festivals, Spring & Fall shows, decorator showhouse boutiques, prestigious holiday marketplaces, and smaller, local fundraisers for churches and community centers. We participated in as many as 25 boutiques shows a year from Pennsylvania to North Carolina.

In 2005. in my 50s, we decided to open DARE Development, LLC to invest, renovate and provide community support to some of the most neglected, overlooked, and struggling neighborhoods on the city’s West Side. We chose blocks where generations of families had lived and were now struggling to stay afloat. Younger generations had moved out; houses had grown vacant development interest was non-existent.

We started small and bought our 1st house on a little one-way street where the existing homeowners/residents were well into their senior years and didn’t want to relocate or couldn’t afford to leave. To date, we have renovated 12 new homes on this block, increased the value, and created better housing opportunities for high-demand rentals with buyer options.

As we grew and became stronger as a crew, we were able to take on collapsed & burned-out buildings on several other blocks in and around Bon Secours hospital. We entered into agreements with the city and the hospital to create a middle-income 1st time homebuyer market with affordable pricing to help diversify that footprint. To date, we accepted the challenge and have taken on whole block projects, renovated full gutt buildings to new. In 2019 we initiated a rent-to-own program to help address the credit issues of potential buyers and perpetual tenants to help in their financial health to educate on the value and benefits of homeownership and legacy. To provide the needed support and guidance to ensure their success throughout the homeownership process.

To date – we have built over 100 units and continue participating in the blocks where we started. We have seen and taken joy in the impact and changes from our efforts. We are grateful that other community associations have asked us to join their revitalization efforts. The hurdles and roadblocks are immense in these neighborhoods. We know our time is a bit limited at our age, but we will finish what we started and, hopefully, will be able to pass along the value and ethics of conscious development to others who work with us along the way. It’s hard work, but you can’t imagine the rewards and joy until you’re there.

To see neighborhoods come alive again, families moving in, children playing, flowers planted, porch furniture placed, car washing, block parties. We are even starting to see existing homeowners investing money into their homes with improvements to keep the increased value of the block going! It’s amazing!

Can you share a story from your journey that illustrates your resilience?

1991 ——- my life took a lot of changes ——- after graduating from design school in 1988 —– immediately took a position as full partner in a successful design firm in the DC metro area ——– loving everything about interior design — the business, the clients – my partner ——— and then ——-BOOM!!!!! 1991 was one of the hardest hit recessions for the design industry ever seen before!!

My design partner decided to close the business, I moved to Baltimore and decided to open a private design studio taking only 1 existing celebrity client. I participated in a decorator showhouse on a shoestring — which landed me a very wealthy client. Everyone thought I was crazy to start a new design business in the financial climate that ruined so many super stars in the design world.

I was on a great roll — until 1993 ——- my marriage broke up — I was on my own facing a very uncertain future. My design studio was flourishing through it all.

1994 — the stock market crashed! I lost a fortune!!! Everything was gone!!! I met a wonderful man who later became my husband.

1998 — married that wonderful man ———- but the design industry was changing so fast in a downward spiral —— 1800 numbers for DIY cropped up everywhere and literally put us all out of business. We had to come up with something fast! So, we started taking left over inventory to boutique shows —- set up booths —— and worked weekends for months and months — which evolved into a pretty profitable adventure.

2005 — we decided to open up a small development company thinking if we could renovate a few homes as rentals – would give us passive income to help out. We bought our 1st investment property in a very run down and little known community and got to work. We did most all of the work ourselves with then help of friends and colleagues — initially, we weren’t terribly well received in the neighborhood — the neighbors really made us ‘pay our dues’. However, in the end we proved that we were sincere in helping make things better —- and quickly became entrenched in the community. We bought other houses to renovate on the block over time ——- and have now completed 12 beautiful new homes. The community association reorganized. The neighbors began taking more interest in their properties. Block parties, flower planting, car washing, families started moving back in. We realized how important community development really makes a difference in people’s lives living in overlooked and neglected blocks.

We started buying properties on other blocks in the immediate area — and to date we have successfully completed over 100 renovations — many of those renovations are on blocks where we have completed 10+ homes for better rentals and now have a rent to own program (initiated in 2020) for potential buyers who have credit issues.

How about pivoting – can you share the story of a time you’ve had to pivot?

2008 ——— the banking/real estate industry totally crashed! We had grown to a crew of 30 — working on 45 homes at a time — had an inventory of ‘to be renovated’ buildings of about 45 —— on target for 20 homes a year on the struggling west side of the city.

Financial investors were really scared – and pulled back significantly. Over the following 12 months – sadly – we were forced to systematically downsize — we lost a lot of really talented guys. We couldn’t finance out of completed buildings since the banks were busted. Our values dropped faster than we could build houses. We were forced to rent — which was scary because people were also losing their jobs at an increased rate. We turned to assistance rental programs. And with skittish investors not willing to start new projects ——– we found ourselves forced to do other investor/owner service work. It kept the doors open – even with a small crew of 4 —— we survived ——–

2011 — investors cautiously came back to start new projects —– but we felt it was important to stay small this time – and now work on 3 – 4 new renovations at a time —– all the while managing the rentals that had grown to about 40.

Contact Info:

• Website: daredevelopment.net
• Linkedin: Caroline Leo

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