Diary of a Serial Entrepreneur: Five Things I’ve Learned

Ethiopian-born D.C. businessman Yimaj “Steve” Kalifa offers his thoughts on surviving and thriving in business

ST. AUGUSTINE, Fla. – — A self-described serial entrepreneur, Washington, D.C.-based Yimaj “Steve” Kalifa began building his business portfolio about 30 years ago. As an immigrant from Ethiopia who first settled in Los Angeles, one of his initial forays into the world of being the boss involved taking over Rap Pages magazine from adult entertainment mogul Larry Flynt, after drooping advertising revenue and dwindling profits forced a shutdown in 1999. 

However, hitting a home run in the publishing business resulted in a mediocre at-bat. After some initial success that put it on par with other titles covering the hip-hop music scene like Vibe, Source and XXL, Rap Pages eventually shuttered, this time for good, due to the same market conditions that led Flynt to drop the publication in the first place. 

As he went back to the drawing board to figure out his next move as an entrepreneur, Kalifa began crisscrossing the country opening branches of a three-doctor-owned home health care company based in Los Angeles. As he grew this company to a $300 million industry behemoth, he soon recognized that an empire of his own was within grasp; it would just take a potent combination of cash on hand and the right opportunity. 

Cash he had. The right opportunity came his way on a routine sales call in north-central Pennsylvania.

“On one trip, I went to Allentown, Penn., where the property owner offered to sell me the whole building for $30,000,” Kalifa said. “Coming from L.A., that was a great price. That was the first property I purchased. But, from that point, in every state that I purchased a property, I leased it back to the three doctors. It was a lot of work starting out on my own, but that was the start of Capital View General Construction Inc.”

Capital View General Construction is now a multimillion company specializing in commercial, road and residential construction, as well as renovation projects in Colorado Springs, Colo., Denver, and Washington, D.C. CVGC and Mechanical Solutions Inc., a Denver-based heating, ventilation and air conditioning company, make up the bulk of Kalifa’s business portfolio. 

He also operates Capitol Medical Supply Inc., a durable medical equipment company in the District, and Source Cuisine, which outbid the former owner of Taylor Gourmet in a 2019 bankruptcy auction to reopen four locations of the popular D.C. sandwich shop.

Although his associate Armstrong Williams, the political commentator, estimates Kalifa’s current personal fortune at $100 million, he’s still had some setbacks. 

He was outbid in 2017 by venture capitalist and sports franchise owner Mark Ein in an attempt to purchase Washington City Paper, a weekly alternative newspaper. Even now, Taylor Gourmet, like most eateries, is suffering the ravages of the coronavirus pandemic, struggling to make payroll while turning a diminishing profit.

Kalifa has turned every setback into a setup, gaining a perspective that guides his everyday stewardship of his company portfolio. In his own words (with a gentle edit for clarity), he shares the five lessons that have kept him in business for the last 30 years:

Hard work pays off
I’ve learned the importance of working hard and giving my best efforts to every task I take on. Even if I’m not successful, just knowing I gave it my best shot allows me to accept the outcome and be satisfied because I know I tried my hardest.

Experience — good or bad — is a good thing
From start-up ventures to companies in publishing, high tech, banking, construction and healthcare, I have acquired so many businesses over the last 30 years. Some have been successful, some not so much. But, all experiences prepared me better for the next acquisition or startup. All experiences are useful, no matter what they are.

Dependability and reliability
Being the head of multiple companies has taught me the importance of being dependable in all aspects. Trust, reliability and sticking to your word are traits that can’t be bought and that show a person’s true character. Your reputation precedes you in the business world, so it’s important to use these traits and apply them to not only business situations, but also generally in life.

Have a goal and take risks
It’s important to have a detailed plan to get to your goals, but I wouldn’t be where I am today if I hadn’t stepped away from my original plan and taken risks outside of my comfort zone. However, it’s important to not take these risks blindly; you should always weigh out your options. It’s challenging, but without it, we wouldn’t reach new levels.

Dream big; don’t dismiss opportunities
Many often dismiss certain opportunities as “too big.” But, you never know if this opportunity will be the one to change your life or lead you to a more successful path. Don’t be afraid of failure.

(Edited by Matthew B. Hall and Carlin Becker)