Stephen Dela Cruz


Our entrepreneur for September is Stephen Dela Cruz. Stephen is known in the San Diego entrepreneur community for running San Diego’s number one coaching and mastermind program.

Stephen was introduced to entrepreneurship at a young age, but not by his parents. He got started on his own by finding beanie babies and reselling them at family events or school.

Although Stephen found himself creative with an entrepreneurial spirit at an early age, he spent most of his childhood, let’s just say, not playing by the rules. He was in and out of the system getting in trouble with the law, never believing he would amount to anything at all. He finally reached the breaking point and was sentenced to juvenile hall.

Ending up in juvenile hall turned out to be the most impactful event up to this point in Stephen’s life. Here he was told he had two choices in life - live a life of crime or find a mentor and end the cycle. It was also during this time, Stephen found Jesus and began to believe there just might be more to life for someone like him.

Stephen chose to end the cycle and by finding a mentor he successfully started his first business. His first venture was photography. Though initially just a hobby, Stephen enjoyed having the best of the best and soon discovered he had to find a way to pay for this new and expensive hobby. He quickly found himself with a vast amount of debt from buying new lenses, cameras, and anything that would move his new hobby forward.

It didn’t take long for his mentors to instruct him to either make money off of it or take it back. Stephen chose to make money off of it and that year he went from a massive amount of debt to filing his taxes with multiple six figure incomes.

This was just the beginning of Stephen’s time as an entrepreneur. Soon thereafter he found himself owning multiple corporations employing hundreds of employees, but his true passion came in 2015 at the age of 28 when a tragedy fell upon the Dela Cruz household.

Up and until this point, Stephen and his wife Angela had been living in a beautiful house in La Jolla, California, where he spent his time running his businesses. This left him overworked and very stressed. One sunny morning while Angela was out of the house, Stephen was deep in the grind when half his body suddenly went numb and collapsed on the floor. He used his tongue to text his assistant who couldn’t hear him calling for help because she was downstairs. She came quickly to Stephen’s aid and called 911. Stephen was so engrossed with a business mindset at this time, that he even argued with the paramedics, stating, “This is not in my budget.”

That was the day Stephen realized that if he had died right then and there, he would leave nothing behind in this world except money. His fortune would be quickly handed over to the name brand stores his wife Angela loved so much. It was in that moment, Stephen decided he wanted to leave behind more from his life. He wanted to leave a legacy - a legacy that was not just money.

Since finding his true calling two years ago, Stephen now devotes the majority of his time teaching entry level entrepreneurs how to live a life that is fulfilled, successful, and flourishing.

It was 2016 when Stephen decided to start his mastermind program to help a few friends learn the importance of having a budget, personal development, and time freedom. After starting out with a mere nine members, today Stephen’s dream has successfully become San Diego’s largest coaching and mastermind group. When asked what makes his program different, he simply said, “Anything that is healthy grows.”

Stephen and Angela have always been devoted to serving their community and solving as many problems as they could. This gives them the edge to think on their feet and solve problems in an instant. A fantastic example is in 2008 when Stephen and Angela had a few real estate holdings. The market took a turn for the worse and it appeared their only option was to sell the real estate for much less than they owed. Having the entrepreneurial mindset they had, they knew there was always more than one option. Somehow they needed to figure out how to turn their real estate holdings into income producing assets. So they hunkered down in prayer and came up with the idea of in-home daycares.

This kind of thinking is what it takes to become a high level entrepreneur in today’s world. This kind of thinking is what Stephen wants to inspire in everyone around him.

Stephen’s desire with his coaching and mastermind program is to give that same inspiration that he received from mentors so long ago. When asked what his “why” is, Stephen told us, “to leave people fulfilled, successful, and flourishing.” At Stegela Success Mastery, the focus is not just on giving you the success in business you crave, but also teaching you the importance of success with significance.

Stephen works tirelessly to build a community that not only focuses on how to build wealth, but also on how to build yourself. When we asked him what the one thing was he wished to inspire in his mastermind group, he replied “I wish to inspire each member to believe in themselves and to live their life to the fullest extent possible.”

From that one day in juvenile hall to today, Stephen has spent his time designing himself to be the best leader and teacher he could be. Now he aims to pass that on to you through his mastermind, podcast, and this magazine.

One piece of advice Stephen would like to leave you with is that it’s your choice. It’s your choice to do or not do. It’s your choice to become or not become. Whatever the choice you make, make it the best choice for you.

Kristen Crooks


Kristen Crooks is a personal assistant, ghostwriter, event planner, and speaker. She works closely with all their clients to truly understand their passions, tone, and ideas so their vision can unfold in front of their eyes. In a world that is increasing more digital Kristen hopes to bring her personal touch to each article, and event that she works on. While working with Stegela Success Mastery Kristen found her passion in writing and planning events for those around her. Starting out in Cosmetology and Barbering Kristen has always enjoyed the freedom that entrepreneurship allows but was not living her passion! Now Kristen focuses on helping others through amazing events, and making sure their stories are told, and heard! While events and ghostwriting are part of her passion, the true joy comes form helping people achieve their goals, and ultimately see others dreams unfold before their eyes.