Let’s talk about what it actually takes to build a legal career that doesn’t hollow you out along the way. Not the glossy version. Not the “grind harder” myth. The real thing—loans, losses, courtroom pressure, and the slow work of becoming yourself in a profession that often asks you to disappear. Today, Ron and Clinton sit down with trial attorney Jared to trace a non-traditional legal path shaped by grit, independence, and a defining trial that changed how he measures fear, failure, and success. From public defense to a solo med-mal practice, Jared’s story challenges what a “successful” lawyer is supposed to look like. What’s it like entering the legal profession without money, connections, or a roadmap? How did public defense and homicide work permanently reset Jared’s stress tolerance? What happens when your very first solo trial is a three-week, multi-defendant med-mal case? How do you recover—financially and mentally—from losing a case you poured everything into? What does real confidence look like when it’s earned the hard way? Why did Jared choose a lean solo practice instead of scaling for volume? How much individuality can lawyers actually bring into the courtroom—and why does it matter? What does it take to build deep, lasting client trust, even when outcomes aren’t perfect? How should young lawyers think about networking, skill gaps, and early responsibility? Why is protecting your health and time not optional—but essential—in this profession? That’s all for today! Huge thanks to Jared for sharing a story that’s honest about pressure, loss, and resilience—and for showing what it looks like to build a modern legal practice without surrendering your identity or your life. Ron and Clinton close by connecting Jared’s journey to the “1958 Lawyer” thesis: a needed shift away from burnout-driven models and toward firms that are both profitable and livable. If you enjoyed this episode, don’t forget to subscribe, leave a review, and share it with a lawyer who’s quietly wondering if there’s another way to do this work. Thanks for listening—we’ll see you next time. About Jared Reynolds:Jared M. Reynolds is a Chicago-based trial lawyer and solo practitioner focused on nursing home abuse, medical malpractice, personal injury, and wrongful death, recovering over $15.7 million for clients to date. A Chicago-Kent College of Law graduate, he clerked throughout law school for the Cook County Public Defender’s Office as a Supreme Court Rule 711 licensed law clerk, handling more than 70 oral advocacy proceedings and trying both jury and bench trials, and he won the National Veterans’ Law Moot Court Championship in Washington, D.C. Jared has served on the board of LAGBAC, Chicago’s LGBTQ+ Bar Association, since 2016, where he leads a mentorship program that has doubled in size and significantly expanded in diversity. Originally from upstate New York, he is an accomplished distance runner, marathoner, and live-music fan who also enjoys backcountry hiking, camping, skiing, and playing drums. Connect with Jared Reynolds: LinkedIn: https://www.linkedin.com/in/jaredmreynolds/ To connect with Jared, you can use this Link to share information. https://forms.gle/VAYwy8WEjKpQPwG2A Connect with Ron Bockstahler: Email: ronb@amataoffices.com LinkedIn: https://www.linkedin.com/in/ronbockstahler/ Company website: https://amatacorp.com/ “Don't Lose Your Balance” book: https://www.amazon.com/Dont-Lose-Your-Balance-Business/dp/1964046467 Show notes by Team Podcastologist Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.
Let’s talk about what it actually takes to build a legal career that doesn’t hollow you out along the way. Not the glossy version. Not the “grind harder” myth. The real thing—loans, losses, courtroom pressure, and the slow work of becoming yourself in a profession that often asks you to disappear. Today, Ron and Clinton sit down with trial attorney Jared to trace a non-traditional legal path shaped by grit, independence, and a defining trial that changed how he measures fear, failure, and success. From public defense to a solo med-mal practice, Jared’s story challenges what a “successful” lawyer is supposed to look like.
That’s all for today! Huge thanks to Jared for sharing a story that’s honest about pressure, loss, and resilience—and for showing what it looks like to build a modern legal practice without surrendering your identity or your life. Ron and Clinton close by connecting Jared’s journey to the “1958 Lawyer” thesis: a needed shift away from burnout-driven models and toward firms that are both profitable and livable.
If you enjoyed this episode, don’t forget to subscribe, leave a review, and share it with a lawyer who’s quietly wondering if there’s another way to do this work. Thanks for listening—we’ll see you next time.
About Jared Reynolds:
Jared M. Reynolds is a Chicago-based trial lawyer and solo practitioner focused on nursing home abuse, medical malpractice, personal injury, and wrongful death, recovering over $15.7 million for clients to date. A Chicago-Kent College of Law graduate, he clerked throughout law school for the Cook County Public Defender’s Office as a Supreme Court Rule 711 licensed law clerk, handling more than 70 oral advocacy proceedings and trying both jury and bench trials, and he won the National Veterans’ Law Moot Court Championship in Washington, D.C. Jared has served on the board of LAGBAC, Chicago’s LGBTQ+ Bar Association, since 2016, where he leads a mentorship program that has doubled in size and significantly expanded in diversity. Originally from upstate New York, he is an accomplished distance runner, marathoner, and live-music fan who also enjoys backcountry hiking, camping, skiing, and playing drums.
Connect with Jared Reynolds:
LinkedIn: https://www.linkedin.com/in/jaredmreynolds/
To connect with Jared, you can use this Link to share information. https://forms.gle/VAYwy8WEjKpQPwG2A
Connect with Ron Bockstahler:
Email: ronb@amataoffices.com
LinkedIn: https://www.linkedin.com/in/ronbockstahler/
Company website: https://amatacorp.com/
“Don't Lose Your Balance” book: https://www.amazon.com/Dont-Lose-Your-Balance-Business/dp/1964046467
Show notes by Team Podcastologist
Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.