Always an Athlete Podcast
Hosted by Jonathan Osborne
A former college athlete and current trial lawyer interviews high-performers on how lessons from sports translate to life, business, and leadership.
This is a long-form interview show where a lawyer and former athlete unpacks the careers of other high-achievers. The central theme is that the mindset forged in competition—discipline, resilience, and dealing with failure—is a blueprint for success in any field. Conversations often pivot from a guest's athletic past to their current professional life, drawing direct lines between the two.
“The host's dual identity as a former D1 athlete and a practicing trial lawyer gives him a unique lens, allowing him to probe both the emotional highs of competition and the analytical aspects of a professional career. Unlike many sports podcasts, the focus is less on stats and scores and more on the transferable 'software' of the athletic mindset.”
Who hosts this show
Jonathan Osborne is a practicing trial lawyer, former federal prosecutor, and shareholder at the Gunster law firm in Florida. He hosts the "Always an Athlete Podcast," where he explores how the lessons from sports carry into business, law, and leadership. A former collegiate basketball player at UNLV and the University of Alaska, Osborne earned his law degree from Georgetown University Law Center and now represents clients in complex legal challenges and investigations.
Credentials & credits
- Shareholder & Chair, White Collar Defense & Internal Investigations, Gunster
- Former Assistant United States Attorney
- J.D., Georgetown University Law Center
- M.A. in Communication Studies, UNLV
- Former collegiate basketball player (UNLV, University of Alaska)
Other ventures
- Holding Court (Blog)
What kind of podcast
- Country
- United States
- Region
- usa
When new episodes drop
- 01
- 02
- 03How Roy K. Altman Teaches His Sons to Love America | Always An AthleteMay 17, 2026 · 3 min
- 04
- 05Who is Roy K. Altman’s Book About Israel Written For | Always An AthleteMay 15, 2026 · 6 min
- 06
- 07
- 08
Notable episodes
- 01The Dive That Changed Everything - Brian Ramos on Fear, Failure & Success
This episode is a perfect encapsulation of the show's premise, as All-American diver Brian Ramos details his athletic highs, a heartbreaking public failure, and his transition to a successful business career.
- 02How Roy K. Altman Teaches His Sons to Love America
In this personal clip, Federal Judge Roy K. Altman tells a heartfelt and humorous story about fatherhood and values, revealing a side of a high-achiever that goes beyond professional accomplishments.
- 03The Jury Box Method: Roy K. Altman on Finding Truth About Israel
This episode demonstrates the podcast's range, moving from sports to applying a legal, evidence-based framework to complex geopolitical issues, showcasing the host's interest in rigorous thinking.
What you'll be asked on this show
Jonathan Osborne runs a methodical, narrative-driven interview. He often opens by stating the show's premise, framing the conversation around the theme of translating athletic lessons to life. He uses open-ended prompts like "Talk about..." to cede the floor to his guests for long, uninterrupted stories. Osborne connects his own knowledge of a guest, like a LinkedIn post, to create informed questions. He consistently builds the conversation from a guest's origin story towards their present-day career, before concluding with a signature two-part finale: a lighthearted question about their past sport and a deep, reflective question about their ultimate legacy.
The show is a calm, single-guest interview format. Host Jonathan Osborne is a patient, active listener who uses broad, open-ended prompts ("Talk about...") to let guests tell their stories at length. He often prefaces interviews by explicitly stating the show's mission and closes with a signature two-question set about the guest's past and future legacy.
Questions Jonathan Osborne keeps coming back to
11 cataloguedIf you're going on this show as a guest, expect some version of each of these. Each note explains when Jonathan Osborne reaches for it.
origin
1- Q.01
“What inspired you to get into your sport?”
This question typically opens the exploration of a guest's athletic backstory.
mindset
2- Q.01
“What did it feel like to be the best at something?”
He asks this to explore the guest's mindset and ego during their peak athletic success.
- Q.02
“Did you ever experience heartbreak in sports?”
This question is used to surface a key story of failure and the resilience that followed.
future
2- Q.01
“What did you see for the future as your college career was ending?”
This question probes the guest's mindset and planning during a critical life transition.
- Q.02
“What's your vision for yourself, personally, family, or professionally?”
This is a forward-looking question asked near the end to understand current priorities.
career
2- Q.01
“What does a career in [your sport] look like after college?”
He asks this to understand the professional landscape, especially for niche sports.
- Q.02
“Tell me about what you do now and what your company does.”
This serves as the primary pivot from the guest's athletic past to their current profession.
values
1- Q.01
“What do you attribute your success to?”
A broad question designed to reveal the guest's core values and support system.
process
1- Q.01
“What does your book contribute to the literature on this topic?”
When interviewing authors, he asks this to get to the core thesis of their work.
personal
1- Q.01
“When was the last time you [did your sport]?”
This is the first of a two-part signature closing, reconnecting the guest to their athletic identity.
legacy
1- Q.01
“What do you want your legacy beyond your sport to be?”
This is the host's signature final question, aimed at uncovering the guest's ultimate purpose.
Signature segments
- · The 'Always an Athlete' premise introduction
- · Signature two-question closing (Past sport & future legacy)
Topics covered repeatedly
Who gets booked here
The show books former elite athletes (e.g., All-American diver Brian Ramos) who have transitioned into successful professional careers, as well as experts in fields like law and politics (e.g., Federal Judge Roy K. Altman) who embody a competitive, high-performance mindset.
- Brian Ramoson The Dive That Changed Everything - Brian Ramos on Fear, Failure & Success | Always An Athlete
- Roy K. Altmanon The Jury Box Method: Roy K. Altman on Finding Truth About Israel | Always An Athlete
Where to find this show
Audience & reach
The podcast does not appear to feature sponsors or ads in the provided evidence. The audience is likely educated professionals, making it a potential fit for B2B services, financial planning, or high-end consumer brands (Estimated).
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
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People also ask
- What is the 'Always an Athlete' podcast about?
- It's a podcast featuring interviews with former athletes, coaches, and business leaders, exploring how the lessons learned from competition apply to sports, business, law, and leadership.
- Who is the host of the podcast?
- The host is Jonathan Osborne, a trial lawyer, former federal prosecutor, and former collegiate basketball player for UNLV and the University of Alaska.
- What is the format of the show?
- It is a long-form, single-guest interview show. The host is a patient listener who asks broad questions to allow guests to tell their stories in detail.
- Is the podcast still active?
- Yes, based on the provided episode data from May 2026, the podcast is actively releasing new episodes.
- What kind of guests are featured?
- Guests are typically high-achievers, including former elite athletes who have transitioned to new careers (like diver Brian Ramos) and experts in fields like law (like Judge Roy K. Altman).
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
- [01]Jonathan Osborne | People - University of Nevada, Las Vegasunlv.edu
- [02]Jonathan Kent Osborne | Business Litigation | Gunstergunster.com
- [03]Gunster Shareholder Jonathan K. Osborne Hosts Federal Judge and Bestselling Author Roy K. Altman on the Always an Athlete Podcastgunster.com
- [04]Always an Athlete Podcast - YouTube Channelyoutube.com
- [05]Roy Altman - Wikipediaen.wikipedia.org
- [06]Brian Ramos - University of Miami Sports Hall of Fameumsportshalloffame.com
- [07]Media - Holding Court with Jonathan Osborneholdingcourt.co
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