From: myfirstmillionpod
Michael Harris, known as Harry O, was a prolific entrepreneur from a young age, boasting 11 different businesses by the age of 26 [00:00:00]. His ventures spanned various industries, showcasing an early and persistent entrepreneurial spirit and diverse business interests.
Early Ventures and Business Acumen
Harris’s first major business was a limousine service, which became quite profitable [00:02:13]. By the age of 23, his limousine company boasted approximately 30 luxury ultra-stretch cars [00:02:51]. He effectively managed bookings, often advertising extensively and then “farming out” excess business to other car services, earning a 50% commission on those transactions [00:03:31].
Beyond the limousine service, his diverse portfolio of businesses included:
- Construction companies [00:02:21]
- Production companies [00:02:23]
- Music companies [00:02:24]
- Beauty salons [00:02:27]
- Real estate investment companies [00:02:32]
He also produced concerts and plays, and supported clubs in Los Angeles [00:02:41]. At its peak, Harris’s collective businesses employed between 100 and 150 people [00:07:18], generating millions in revenue [00:07:33].
Foundations of Business Knowledge
Harris’s early business experiences significantly shaped his entrepreneurial approach. As a child, around 11 to 13 years old, he worked at a shoe shine parlor in his neighborhood, learning about competition and how businesses were run [00:04:40]. He keenly observed business owners, preachers, and even “people from the street,” learning diverse approaches to business [00:05:21]. This taught him not to “judge a book by its cover,” recognizing potential clients beyond initial appearances [00:05:44]. He always sought lessons from every experience, asking, “How do I use this moving forward?” [00:06:31].
His mother, who owned a restaurant, also provided a direct example of effective business management, customer relations, and staff interaction [00:06:40]. She even rose from working for the previous owners to acquiring the business herself [00:06:53].
Real Estate Investments
A core component of Harris’s financial strategy was investing in real estate [00:07:46]. He sought out deals across various locations, purchasing both rehab properties, luxury properties, and business outlets [00:07:55]. At one point, he owned an estimated 30 to 40 buildings [00:08:14].
Transition to Entertainment
Harris’s entry into the entertainment industry evolved from his existing ventures. He opened a studio called “The Jingle Factory” in a building he owned, producing commercials for local businesses and radio stations [00:09:13]. This brought him into contact with musicians, producers, and singers [00:09:35]. His limousine service also catered to production companies and artists, further connecting him to the industry [00:10:06].
He established his own production company, “Why Not Production,” to provide opportunities for individuals who looked like him, and who lacked the financial means to produce their own work [00:11:09]. This led him to produce plays, which he saw as a creative space for movie professionals between jobs and a way to bring entertainment to his community [00:11:45]. He produced a play called “Checkmate,” taking it to various cities and ultimately to Broadway with Anita Landers [00:12:52].
Business Philosophy
Harris’s approach to business involved taking a managing partner role in his investments [00:13:51]. He prioritized learning everything about the specific business he invested in, combining that knowledge with his management skills to elevate the venture [00:14:10]. This hands-on, learning-oriented approach was a consistent part of his entrepreneurial journey.
Personal Challenges and Reflections
Harris’s adventurous business ventures included involvement in the drug business, where he stated his sales reached “two million a day” [00:19:16]. He reflects that while it was exciting and enterprising, it also destroyed his community and made him “poor in spirit” [00:19:45]. He acknowledges that he was “young and misguided” in that venture [00:20:21].
His life “came crashing down” when he was arrested and sent to prison, just as his Broadway play was about to fully launch [00:13:05]. He was initially charged with attempted murder (later exonerated after 23 years [00:18:02]) and drug conspiracy [00:17:49]. Despite being incarcerated for 33 years [00:22:52], Harris’s entrepreneurial drive persisted.
Founding Death Row Records from Prison
While in San Quentin, Harris helped establish Death Row Records [00:24:21]. He described it as the “next iteration” of Ruthless Records, capitalizing on Dr. Dre’s discontent with his previous situation [00:26:56]. Harris and his attorney, David Kenner, assembled the company while Harris was behind bars [00:29:11]. The name “Death Row” was inspired by Harris being housed on death row in San Quentin and witnessing younger individuals sentenced to death [00:28:33].
Death Row Records, featuring artists like Dr. Dre, Snoop Dogg, and Tupac, quickly became a game-changer in the music industry [00:29:55]. The label’s success with albums like “The Chronic” and “Doggystyle” was rapid, selling millions of copies and influencing the music landscape [00:42:07]. Harris saw this as a “legitimate venture” making significant money, a stark contrast to his past illegal activities [00:43:24].
Legacy and Continuous Entrepreneurship
Harris’s entrepreneurial journey is marked by an enduring spirit, regardless of circumstances. He viewed Death Row Records as a “choo-choo train” that connected them to major companies like Universal and Warner Brothers, changing the game for many rappers [00:31:19]. He is now the CEO of the new Death Row, which he helped create decades ago [00:32:34]. He continues to embody the “creating something out of nothing” mentality, which he finds relatable between hip-hop entrepreneurs and tech innovators [00:55:42]. His story is a testament to the diverse and often unexpected business ventures one can undertake.