
"I thought if I went to law school, I could have my cake and eat it too. I like to debate, and there's no math," he said.
Isaac attended Western State University in San Diego (which is now called Thomas Jefferson School of Law), graduating 10th in his class, something he had thought would never be possible. Once he graduated from law school in 1976, Isaac clerked for a lawyer and went into practice with him very shortly thereafter, forming the legal clinic of Flickinger & Isaac.
"We ended up becoming partners within literally a month of my graduation," Isaac said. "I had no experience, and he had 10 years."
At the time, legal-services advertising was just starting to gain momentum, and Isaac was excited to lead the way in this landmark leap. He opened up a series of legal clinics, becoming the first lawyer in San Diego to advertise law services. Soon after his partner retired, Isaac had a career-changing epiphany.
"I really started realizing that I don't enjoy being a paid gladiator. I did a lot of divorce law and a lot of reactive law that is not really fun," he said.
Once he had ditched law, Isaac got into sales for about a year; then he returned to law, practicing in the area of personal injury. Still "disenchanted" with law, Isaac left the legal profession yet again. But this time he opened his own business—a bagel shop called Bagel Town Café. Describing that experience as "grueling," Isaac ultimately sold his bagel shop and went back to his original love: helping people with their legal issues.
When he was running his bagel shop, Isaac was able to make a connection with a local DJ who had him on his show to promote the store. After he went back to law the second time, he started an organization called Legal Assist, a paralegal group that he led, which offered certain legal services to average people at affordable prices. Isaac was brought back onto the radio show to promote this venture, and he eventually landed a spot on the show, providing legal advice twice a week. This is how his new approach to law was born.
Once his success and popularity on the radio escalated, Isaac was asked to host his own show, The Lawyer in Blue Jeans, which is also a nickname that illustrates his down-to-earth and relaxed outlook and approach to law.
"I wear blue jeans literally every day—I have 49 pairs. It's part of my uniform now. It's more than what I wear. It's the philosophy of how I act as a lawyer," he said. "I believe that law is too esoteric; lawyers are too 'holier than thou' in many cases. I bring law down to earth. I say things in ways they [clients] can understand and make them feel comfortable. There's no intimidation."
Soon after his reputation as the Lawyer in Blue Jeans expanded, Isaac renamed his legal group, Legal Assist, The Lawyer in Blue Jeans Group. This company aims to provide easy-to-understand and affordable legal documents to all types of individuals. Isaac focuses much of his effort on living trusts, which he finds to be very important for everyone to have.
"Living trusts protect everyone from probate. It's so important to have that because it literally distributes your assets immediately without the interference of the government or lawyers," he said.
Isaac has modeled his legal outlook on that of Gerry Spence, along with his dressed-down look. He also has drawn significantly from author and motivational speaker Wayne Dyer. Dyer's books and speeches taught Isaac how to lead a seminar and handle affairs in front of the public. Isaac's father also provided him with a great foundation, career-wise.
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Isaac suggests that law students and lawyers start to think about the profession and what they want from it as early as possible. Before becoming the anti-lawyer attorney that he is today, Isaac saw just how many lawyers do not love what they do.
"Most lawyers are unhappy," he said. "I have plenty of experience with lawyers in court, and the topic of conversation in court is 'How do I get out of this profession? We're stuck. I'm not qualified to do anything else.'"
"When you have to bow down to judges, you're a slave to your calendar, and you have to play the game. Most lawyers are done with it after a while," he added.