Cleared Hot – Episode 408

Guest: Josh Tomeoni
Theme: Life, Divorce, Rebuilding, and Financial Security
Air Date: September 22, 2025
Host: Andy Stumpf

Episode Overview

Andy Stumpf hosts Josh Tomeoni, a financial planner and divorce coach, for an in-depth conversation about navigating life's upheavals—especially divorce, its emotional and financial fallout, rebuilding purpose, and modern masculinity. The episode weaves stories of personal transition, the “midlife crisis,” male vulnerability, personal growth, addiction, and the realities of seeking (and offering) support through dark times.

The tone is candid, humorous, occasionally irreverent, and always deeply honest—aimed at demystifying taboos around men’s struggles, especially as they relate to identity, emotional health, and relationships after significant life changes.

Key Discussion Points & Insights

1. Podcasting, Ethics, and Business Models

[00:34–04:12]

• Andy and Josh discuss the phenomenon of podcasts charging guests, with both expressing distaste for the practice.

• Reflection on creating authentic business models versus profit-driven (and “icky”) approaches in new media.

  “I mean, we're talking five figures, which doesn't make sense to me. For one episode.”
  —Josh, [01:55]

2. Community, Moving, and the Value of Neighborliness

[04:13–07:27]

• Both reflect on moving from urban to rural areas seeking authentic community.

• Stories of neighbors helping each other, contrasting the surface connections in cities with the deeper reliance found in rural towns.

  “One of the reasons we moved up here is we bought an investment property ... but, like, out there, you know your neighbors. And they've helped us.”
  —Andy, [06:20]

3. Politics & City Life—Portland, San Francisco, Homelessness, and Policy

[07:30–12:04]

• Discuss Portland’s protests, changes in urban policy (homelessness, drug decriminalization), and the slow pace of recovery in major US cities.

  “...Portland just fell apart and they rioted for like 100 days straight. ... It's like two city blocks. And Portland is huge.”
  —Josh, [08:21]

4. Life As a Financial Planner & Market Realities

[12:07–15:47]

• Josh shares his two-decade background in financial planning, explaining market unpredictability and debunking the fantasy of easy wins (Bitcoin, stock picking).

  “If you look at The S&P 500 ... about five of them ... has been about 40% of the return. ... Anything happens to those companies...and the whole S&P 500 dramatically shifts.”
  —Josh, [14:02]

5. Divorce: Identity, Purpose, and Male Vulnerability

[15:25–20:06]

• Josh and Andy both recount divorces, discussing how loss triggered profound reflection on identity, purpose, and masculinity.

• They critique societal messaging that leaves middle-aged men isolated, caught between stoicism and “over-pussified” therapy culture—arguing for a “middle space” of honest support.

  “We don't really have a space where we can be open about that or that we can explore ... this sucks. I don't know what my identity is anymore.”
  —Josh, [17:08]

  “Some of the saddest people I've ever seen are the ones that portray the happiest. And it sucks to see.”
  —Andy, [19:55]

6. The Divorce Process: Coaching, Therapy, and Systemic Gaps

[20:12–27:33]

• Josh explains “divorce coaching”—distinct from legal and financial advice—aimed at helping people transition emotionally and practically.

• Both share personal experiences with therapy: its value, pitfalls, and the reality that lasting change requires doing the work oneself.

  “A therapist's job, in my humble opinion, is to help you get from past to present. ... A coach is looking at you present to get you forward.”
  —Josh, [28:24]

7. Masculinity, Generational Change & Relationship Roles

[33:11–36:24]

• Discussion on shifting roles of men across generations, from defined provider-protector models to more flexible, discussion-based dynamics in modern relationships.

  “If you find somebody that you love, you shouldn't have to be stressing about, oh, I need to do this... Just talk out with your partner.”
  —Producer Michael, [35:22]

8. Parenting Through Divorce & The Impact on Kids

[36:30–43:39]

• Andy expresses concern for the impact divorce had on his children, especially his eldest.

• Both share how they try to model resilience and openness, and foster healthy attitudes toward relationships—even after personal heartbreak.

  “A failed relationship...does not mean that all relationships are going to fail. If you find the right person, you can make it work.”
  —Andy, [39:58]

  “I ask them what they failed at during the day ... to just be okay with the fact that things are going to not work out the way that you wanted them to work out.”
  —Josh, [43:10]

9. Failure, Social Media, and the Myth of Perfection

[44:34–45:08]

• The hosts highlight how social media obscures life’s struggles, making failure taboo when it’s normal and essential for growth.

  “People are looking for this painless, joyous, stress-free life...it’s not real.”
  —Andy, [44:36]

10. Addiction, Escapism, and Present-Moment Living

[47:00–54:42]

• Josh reframes addiction as the “escape from the present moment,” expanding it beyond substances to include overwork, exercise, relationships, even morning routines.

• Talks about 12-step programs, authenticity vs. vulnerability, and the challenge men face admitting powerlessness or asking for help.

  “Addiction is just escaping the present moment. ... I could use alcohol, drugs, pornography, shopping, dating, rebound relationships.”
  —Josh, [47:09]

  “We relate better to being authentic than to being vulnerable.”
  —Josh, [53:20]

11. Toxic Masculinity, Power, and Social Narratives

[56:01–65:00]

• Josh argues that “toxic masculinity” is a cultural misnomer, positing that authentic masculinity and femininity are healthy—“toxic” is just toxicity, disconnected from genuine masculine or feminine traits.

• Andy agrees the catchiness of the term causes damage to perceptions of manhood.

  “I don't believe toxic masculinity exists...masculinity itself is actually a very healthy thing.”
  —Josh, [58:29]

12. Life Cycles, Growth, and the “Midlife Crisis”

[68:01–77:41]

• The two explore the “seven-year life cycles”—points of crisis, pruning, rebirth, and reflection through life’s decades.

• The “midlife crisis” is reframed as a spiritual, emotional reset, necessary for advancing to the next personal level.

  “From my experience, life tends to cut me down when I think I have it figured out...”
  —Josh, [111:08]

13. Male Friendship, Shared Trauma, and Depth

[81:23–90:11]

• Both discuss the rarity and value of honest male friendship in the absence of competition—how shared trauma (military, divorce, or otherwise) forges trust, vulnerability, and deep connection.

  “Some of the most trust-built friends that I've ever had came from shared experience...us all going through divorce at the same time.”
  —Josh, [86:00]

14. Divorce’s Darkest Moments: Identity & Loss

[90:11–101:27]

• Both share the hardest moments of divorce—not the legal process, but the emotional gut-punch of losing identity and sense of self-worth.

  “It was the moment where I realized just how big the chasm was...I convinced myself...somehow it was still gonna be okay. ... Oh, wow. This is not going the other way, and it's just getting worse.”
  —Josh, [92:10]

  “The divorce. For me, people think that going through SEAL training was hard. ... the divorce was harder...emotionally just shattering sense of self.”
  —Andy, [100:21]

15. Rebuilding, Forgiveness, and Acceptance

[101:27–104:21]

• Stories of forgiveness and rebuilding, agreement that the pain was worth it for the personal transformation—and for their kids.

  “Would you go through it all again to arrive at the place right now? I would as well.”
  —Andy & Josh, [103:08]

16. Commitment & Remarriage After Divorce

[115:31–120:57]

• Debate on the value of remarriage, especially for men—given legal, financial, and emotional realities post-divorce. Emphasis on commitment over ceremonial paperwork.

  “I don't see a lot of advantages for marriage anymore. ... It's more about the commitment than it's about anything else.”
  —Josh, [116:05]

17. Playful Close: Dogs, Movie References, and Staying Human

[121:13–126:59]

• Light-hearted banter about pets (Andy’s miniature dachshund), the importance of confidence and authenticity—and a detour into cult films (Boondock Saints).
• Josh shares his Instagram handle (@joshthederelict) as a resource for men seeking guidance or community during divorce or major life transition.

Notable Quotes & Moments

• Josh on masculine crisis:
  “The highest suicide rate in America, 35 to 50 year old men. Why? We're at the peak of everything. ... We are defined by our similarities, not our differences.” [18:36]

• Andy on failure and parenting:
  “I ask them what they failed at during the day... I want them to understand... to just be okay with the fact that things are going to not work out the way that you wanted them to work out.” [43:10]

• Josh on moving forward after loss:
  “It's just a new layer of okay, here's another failure. How do I look at this? Do I see myself again as this shameful person ... I wouldn't change a thing.” [102:42]

• Andy on camaraderie:
  “What is camaraderie? ... laughter and suffering, probably coexisting back and forth in a matter of seconds.” [87:36]

Timestamps for Major Segments

• Podcast Business Ethics: [00:34–04:12]
• Small Town vs. City Life: [04:13–07:27]
• Portland/Urban Policy Disasters: [07:30–12:04]
• Financial Markets & Life as a Planner: [12:07–15:47]
• Divorce & Male Vulnerability: [15:25–20:06]
• Divorce Process, Therapy & Coaching: [20:12–27:33]
• Masculinity & Generational Roles: [33:11–36:24]
• Parenting Through Divorce: [36:30–43:39]
• Failure & Social Media Perfection: [44:34–45:08]
• Addiction & Escapism: [47:00–54:42]
• Toxic Masculinity, Language & Society: [56:01–65:00]
• Life Cycles and Midlife Crisis: [68:01–77:41]
• Friendship and Trauma: [81:23–90:11]
• Hardest Moments of Divorce: [90:11–101:27]
• Remarriage & Commitment: [115:31–120:57]
• Closing: Community Resources & Culture: [121:13–126:59]

How to Connect with Josh

• Instagram: @joshthederelict
• Josh offers community, coaching and resources specifically for men (especially ages 35–50) navigating divorce, rebuilding, and seeking authentic connection.

“We're often just asking ourselves the question that we're telling our kids.”
—Josh, [43:10]

“Suffering is universal. We are not alone, even when life feels darkest.”
—Andy, throughout