The David Guttman Podcast

You think rescuing your kids is love? Trystan Trenberth spent years thinking the same thing, until a therapist friend's single question forced him to see that his daughters didn't want him to solve their problems. They wanted to be heard. Trystan unpacks why failure isn't off the road to success but is the road, and how that same contrast principle reshaped his approach to fatherhood, fitness, and the overfunded whole life insurance strategy he uses to build wealth today.

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Timestamps

00:00 - Introduction: Why failure is the road to success

02:05 - UK roots, parents, and an early love of design

04:30 - Hotel management to IT: a career pivot

06:13 - Rich Dad Poor Dad and the move into real estate

08:39 - Raising capital and the relationship-first approach

10:52 - Fiduciary instinct and gut decision-making

11:35 - Building a team, fix and flips, and wholesaling ethics

13:17 - Midlife to Millions and the retirement reset

17:51 - Quick take on crypto

25:12 - Infinite banking explained

27:30 - Overfunding a whole life policy with real numbers

29:34 - Borrowing against the policy and the arbitrage

30:39 - The Rockefeller method and generational trusts

32:27 - Self-taught, Nelson Nash, and where "infinite" comes from

33:30 - UK vs US: where home is now

37:33 - Free speech, capitalism, and crony incentives

39:55 - Losing 70+ pounds at 47 and the skydiving trigger

42:00 - First half marathon under two hours

45:21 - Unexpected mentorship at mile 11

48:23 - 220 jumps in 16 months

51:18 - Two daughters, divorce, and the parenting reset

55:00 - Want to be heard, or want me to solve it

57:09 - Music, Clapton, and shared experiences

58:25 - Where to find Trystan

Watch the “David Guttman Podcast” every Tuesday at 8AM EST on YouTube https://bit.ly/3ZGK2yv

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At 20, Chloe Kosco was just making things for herself in the corner of her college apartment. Then her first drop sold out in seconds, and everything changed.

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Timestamps

00:00 - Intro

01:18 - Growing up around her mom's sewing machine

03:30 - Why she finally asked for her own machine

04:55 - Patchwork pants and the first college experiments

06:30 - Strangers start asking where she got her clothes

07:50 - The first Instagram drop sells out in seconds

09:54 - "I thought you trained your whole childhood"

12:05 - Where her mom learned to sew (no fashion school)

13:38 - Building the first shoppable website

16:43 - The $300 thrifted bedsheet pants

18:58 - Working with her mom as a business partner

43:03 - The three-tier pricing model explained

45:41 - The five-year plan and in-store sewing classes

48:37 - Will there ever be a men's line?

49:33 - The real headcount behind the brand

51:24 - The full rebrand drops in March

52:55 - How she casts her models

53:03 - Where to find Bohemia by Chloe

Watch the “David Guttman Podcast” every Tuesday at 8 AM EST on YouTube https://bit.ly/3ZGK2yv

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There’s a moment Vince Ricci describes where time froze: a gun in his back outside his own home, his wife and newborn daughter inside, and two armed strangers waiting for him to open the door. Untrained and outnumbered, he made a choice that went viral hundreds of millions of times over. But the real story isn’t the shootout; it’s what he learned about getting “civilized,” the Rocky-esque warning about what comfort does to a fighter, and why he believes every man has an obligation to stay dangerous for the people he loves.

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Timestamps

00:00 ​Intro of Show

01:31 Vince Ricci’s Back Story

05:20 Work Ethics and Motivation

07:59 SEAL Mentality

10:03 Entrepreneurial Journey

13:55 Running Trina’s Kids Foundation

19:16 Having a Second Chance at Life

29:33 Parenting Styles and Values

35:13 What’s Next for Vince?

36:21 Running a Cannabis Business

43:35 Wellness and Biohacking Practices

49:00 Vince’s Next Goals

Watch the “David Guttman Podcast” every Tuesday at 8 AM EST on YouTube https://bit.ly/3ZGK2yv

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There’s a moment in most people’s lives when something so raw and undeniable happens that they can no longer pretend the old version of themselves is working. For Roger da Silva, that moment came at two in the morning in one of Rio’s most dangerous neighborhoods, high and staring at a man running toward him screaming “Lucifer.” In this deeply personal conversation, Roger walks me through a spiritual journey that began with a baptism at 14, detoured through addiction and near-death, and ultimately arrived at a life built on faith, family, and purpose.

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Timestamps

00:00 ​Intro of Show

03:30 Roger da Silva’s Back Story

13:06 Changing His Life through Christ

18:39 Why He Suffered from Addiction

20:15 Transforming His Life for Good

29:51 Leaving His Baggages behind

31:36 Becoming an English Teacher despite His Learning Disabilities

38:14 Following His Mission

49:00 “Luciferian” Syndrome

54:37 Judgment vs. Evaluation

58:02 Advice for People Seeking Faith

1:04:42 How to Pray over/for Someone

1:08:00 What’s Next for Roger?

1:10:04 Connect with Roger

Watch the “David Guttman Podcast” every Tuesday at 8AM EST on YouTube https://bit.ly/3ZGK2yv

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Before you play a single hand of poker, before you take a single golf swing, Jaymes Rosenthal already knows who you are. In this episode, we explore how elite-level pattern recognition, developed through years of live poker and trading, becomes a lens for navigating every area of life. We go deep on humility, momentum, servant leadership, equity structures, and why the soft skills nobody talks about are the ones that actually compound.

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Timestamps

00:00 ​Intro of Show

01:02 Lessons from Poker and Golf

03:07 Reading People Instantly

08:19 Pattern Recognition in Poker

12:56 Developing Passion for Golf

15:17 Emotional Control and Tilt

18:05 Self Awareness and Discipline

20:29 Balancing Emotions and Intellect

22:35 Not Addressing the Root Cause

26:31 Financial Strategies and Reality

29:48 What Makes Entrepreneurs Successful

33:34 Servant Leadership in Business

39:22 Ownership and Incentives

42:39 Building Strong Teams

46:44 Transparency in the Company

49:06 Learning from Young Entrepreneurs

53:17 Getting into Trading

57:38 Importance of Humility

01:01:20 Breakthrough in Trading

01:02:29 Living a Life of Risk

01:05:23 Teaching Kids to Think

01:08:13 Passion Project Bitcoin

01:16:48 Connect with Jaymes

Watch the “David Guttman Podcast” every Tuesday at 8AM EST on YouTube https://bit.ly/3ZGK2yv

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Tanner Chidester spent over $3 million on coaches, masterminds, and mentors, and he has zero regrets. In this episode, he shares how he used to evaluate which investments in himself were worth making, why he fired coaches after 30 days if results weren’t materializing, and how a chance lunch with a family friend changed the entire direction of his life. What’s the one investment in yourself you’ve been putting off that could change everything?​​​​​​​​​​​​​​​​

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Get Tanner Chidester’s book, “Infinite Income: The Eight-Figure Formula for Your Online Business”:⁠⁠ ⁠⁠⁠⁠https://bit.ly/48gpL88⁠⁠

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Connect with Tanner Chidester

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Timestamps

00:00 ​Intro of Show

01:55 Tanner Chidester’s Back Story

05:21 Motivation from His Upbringing

08:43 Athletic Journey

11:08 Pivoting to Entrepreneurship

15:47 Family Life

17:45 Investing $3M in Mentorship

22:05 Lessons from His Experience

24:18 Business Scaling and Exit, Sabbatical Leave, and Book Publishing

27:59 Investing in Private Equity

38:42 Red Flags in Portfolio Companies

41:13 Values to Look for in Business Collaborations

43:08 Views on Charlie Kirk

46:20 Legacy Perspective

49:37 Defining One’s Purpose

52:41 Managing Romantic Relationships

58:16 Goal-Setting for the Future

1:00:13 Connect with Tanner

Watch the “David Guttman Podcast” every Tuesday at 8AM EST on YouTube ⁠⁠https://bit.ly/3ZGK2yv⁠⁠

Connect with David Guttman

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Most people spend their entire lives waiting for others' approval, never stopping to ask what they actually want. Travis Chappell grew up inside a fundamentalist Baptist world so insular that he graduated kindergarten through college on the same 140-acre campus, committed to full-time ministry at age 12. In this episode, Travis and I unpack how radical self-awareness isn’t something you’re born with, but it’s something pressure forces out of you.

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Connect with Travis Chappell

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Instagram: https://bit.ly/4bWBzxm

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Timestamps

00:00 ​Intro of Show

01:31 Travis Chappell’s Back Story

09:28 Growing Fundamentalist Baptist Church Community

14:21 Going the Unconventional Route: Leaving the Church

28:26 Accepting Truth Wherever You Find It

32:00 Identifying Blind Spots

35:45 Launching Guestio

38:32 Podcasting = The Best Networking

43:38 Leaving the Church with His Wife

52:52 Having an Objective View of Reality

55:16 Travis and David’s Political Views

59:40 What’s Next for Travis?

Watch the “David Guttman Podcast” every Tuesday at 8 AM EST on YouTube https://bit.ly/3ZGK2yv

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There’s no dress rehearsal for the moments that define you, and David Temko has lived that truth more than once. In this episode, I’m with the founder and CEO of C2 Financial to unpack a life shaped by entrepreneurial parents, a starter marriage, his father’s passing, and the unexpected clarity that comes when everything converges at once. David shares how traveling through 20 countries, cutting his teeth in commercial real estate, and eventually building his own commercial lending division prepared him for a leadership role he never asked for but was always being built toward.

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Connect with David Temko

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Instagram: https://bit.ly/4bGSJii

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Timestamps

00:00 Intro of Show

01:19 David Temko’s Back Story

04:06 David’s Entrepreneurial Journey

08:54 His Father as His Mentor

17:36 Transitioning to Mortgage Brokerage

21:15 David’s Leadership Style

23:17 Retaining and Motivating Talents

26:55 David Guttman’s Cancer Misdiagnosis

35:58 Personal and Family Goals

43:21 Teaching Resilience to Children

49:52 Benefits of Mentorship

54:52 Lessons from Past Marriage

58:47 Connect with David Temko

Watch the “David Guttman Podcast” every Tuesday at 8AM EST on YouTube https://bit.ly/3ZGK2yv

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Growing up in the shadow of a celebrated father isn’t a head start, it’s a gauntlet. Frank Ioppolo built his legal career largely to prove something to himself, channeling that chip on his shoulder into becoming the youngest partner at Greenberg Traurig and eventually running his own firm, with his father in the office right beside him. The three years they spent working desk-to-desk taught Frank more than his previous two decades of practice combined, and the two are still collaborating today. 

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Get Frank Ioppolo’s book, “ILG Blue Book” here: https://bit.ly/4dn9QrY

Connect with Frank Ioppolo

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Timestamps

00:00 Intro of Show

01:55 Reconnection of Frank and David

05:50 Frank Ioppolo’s Back Story

13:10 Lessons from His Mentors 

20:06 Managing Romantic Relationships

28:38 Advice to His Children

33:26 Leadership Perspectives

37:48 Stance on Charlie Kirk

44:58 Marriage Journey

49:54 What’s Next for Frank?

55:32 Message to His Children

Watch the “David Guttman Podcast” every Tuesday at 8AM EST on YouTube https://bit.ly/3ZGK2yv

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Six hundred rejections in six weeks sounds like failure, but Seve Ortale called it his education. In this episode, Seve shares the unexpected journey from philosophy major and volunteer firefighter to founding a payment processing company, and what wrestling, fire scenes, and door-to-door sales all have in common when it comes to building real character. What does it actually mean to stay coachable when you’re already winning?

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Connect with Seve Ortale

Website: https://bit.ly/4rWVVNL

YouTube: https://bit.ly/4uj0dRd

Instagram: https://bit.ly/4sz3ni0

TikTok: https://bit.ly/40hTYiX

X.com: https://bit.ly/46NsmWx

LinkedIn: https://bit.ly/3OXe8MK

Timestamps

00:00 Intro of Show

01:27 Seve Ortale’s Back Story

06:47 Volunteering in the Fire Department

10:05 Lessons Learned from Volunteerism

13:03 Entering the Payment Processing Industry

19:36 Early Sales Struggles and Rejection

21:23 Seve’s Biggest Learning Curve

22:57 Perspective on Residual Income

24:32 Building and Scaling the Business

28:44 What’s Next for Payments University?

30:00 Working with His Partner

35:43 Seve’s Faith and Values

41:26 AI & Cryptocurrency in the Financial Industry

45:14 Crypto Startups vs Giant Companies

50:14 Ego, Curiosity, and Humility

56:47 People That Keep Seve Grounded

58:32 Long Term Plans

1:00:06 Connect with Seve

Watch the “David Guttman Podcast” every Tuesday at 8AM EST on YouTube https://bit.ly/3ZGK2yv

Connect with David Guttman

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