Stefan Whitwellin the media.
Stefan Whitwell, CFA, CIPM, Co-founder of Chaos Holdings, LLC, is a frequent podcast guest. He brings a builder's view of AI and automation inside a regulated firm, from AI in investing to keeping the human relationship as the work speeds up. He is co-author of If Done Right, the AI governance framework for regulated financial firms. Audiences also remember the story: losing everything in 2009, owning it, and rebuilding; Zen and Jujutsu; and raising four children.
The builder behind the framework.
Hosts invite Stefan for a builder's view of AI, business, and money. Audiences remember the story. Four threads run through every conversation he has.
He builds with AI inside a regulated firm
Stefan does not only talk about AI. He deploys AI and automation inside a working advisory firm, from an around-the-clock concierge line to research workflows, without losing the human relationship. He is co-author, with Brandon Veldman, CFA, of If Done Right: The AI Governance Framework for Regulated Financial Firms.
He lost everything in 2009, owned it, and rebuilt
In the middle of the Great Recession, a bank declined to renew one loan on Stefan's real estate portfolio. The default spread to every other loan, and he lost everything, with three children at home. He owns his part plainly: he was over-concentrated and had no asset protection or tax plan. A mentor told him, "You know, you walk through fire. You should advise others." He rebuilt from there, starting a wealth management career that led him to found Whitwell & Co. in 2017.
“The hardest part was in bankruptcy court; it was telling my kids we can't afford summer camp.”Watch: his origin story→
Zen, Jujutsu, and 40 years of violin
Stefan spent a year in Japan studying martial arts and apprenticing with Zen Master Sanshu at the Saijo-ji temple. He holds a black belt in Hakko-Ryu Jujutsu and a brown belt in Brazilian Jiu-Jitsu, and has played the violin for more than 40 years. He brings the same patience to markets, to clients, and to the long work of building a firm.
“So show up, even when it sucks. That principle will help you build wealth, will help you get better on the mat, will help you build teams. No flash, just reps.”Watch: Consistency Beats Intensity→
A father of four, first
Stefan grew up watching his own father, a school teacher, start a self-publishing business to make ends meet, and noticed that it meant his dad was around when he needed him. He runs his firm to follow that tradition: a thriving business, and a family that thrives along the way. Three of his four children are grown; the youngest is at home with him.
“I think my most important job is being dad.”Watch: The Real Me→
Podcast and media appearances.
Stefan's guest appearances on AI, business, and the human side of building something that lasts. Upcoming and unreleased episodes come first, then everything that has aired, newest first. Episode titles are each show's own wording.
Upcoming
2027
Sharkpreneur
Hosted by Kevin Harrington and Seth Greene
Topic: Entrepreneurship and wealth.
Recorded, not yet released
2026
Passion Millionaire Podcast
Hosted by Robert Roth
Topic: Background, entrepreneurship, and general financial planning.
Podcast
September 4, 2026
Win Make Give with Ben Kinney
Hosted by Chad Hyams
Episode: “The Holistic Wealth Paradigm: Health, Wealth, and Purpose with guest Stefan Whitwell”
Topic: Wealth, health, and purpose.
Podcast
August 25, 2026
CEO Sales Strategies Podcast
Hosted by Doug C. Brown
Episode: “When $100 Million Makes Decisions Harder”
Topic: Decision-making and wealth at scale.
Podcast
July 26, 2026
The Unforget Yourself Show
Hosted by Mark and Katie
Episode: “When Success Stops Feeling Like Success with Stefan Whitwell”
Topic: Purpose, wealth, and life decisions.
Podcast
June 25, 2026
Business Leaders of America Podcast
Episode: “What Great Advisors Understand About Wealth, Risk, and Life”
Topic: What good advice looks like across wealth, risk, and life.
Podcast
February 19, 2026
The Ambitious Generation
Hosted by Jack Wagoner
Episode: “He Lost $35 Million, Went Bankrupt, Then Rebuilt Everything | Stefan Whitwell | 123”
Topic: Losing everything in the Great Recession, and rebuilding.
Video interview
December 27, 2023
Founder Wisdom Podcast
Hosted by Charles Cormier
Episode: “travels, wealth, jiu jitsu and priorities with stefan whitwell”
Topic: Travel, wealth, Jiu-Jitsu, and priorities.
Podcast
July 18, 2023
7 in 7 Show with Zack Ellison
Hosted by Zack Ellison
Episode: “How AI Transforms The Investment Industry With Stefan Whitwell, Founder & CIO, Whitwell & Co.”
Topic: AI in the investment industry.
Video interview
July 15, 2022
Changing Reality with Harsha
Hosted by Harsha
Episode: “Changing Reality with Stefan Whitwell, Founder and Chief Investment Officer at Whitwell & Co”
Topic: A career across global finance.
Conversations Stefan can carry.
For a technology, business-owner, or leadership audience. Each stands alone as a segment or a full episode.
Governing AI in a regulated firm
What it takes to put AI to work where an examiner can ask to see the work: knowing which tools are in use, setting guardrails that hold, and keeping a record that stands up. Drawn from If Done Right.
Automation without losing the relationship
Where AI and automation belong in a client-facing business, where they do not, and how a firm can move faster without feeling less personal.
Losing everything in 2009, and rebuilding
What it was like to lose it all in the Great Recession with three children at home, what he got wrong, how he rebuilt, and why resilience is built before the crisis, not during it.
Discipline: Zen and Jujutsu
A year apprenticing with a Zen master in Japan, a black belt in Hakko-Ryu Jujutsu and a brown belt in Brazilian Jiu-Jitsu, and what daily practice teaches about building systems and teams.
Invite Stefan on your show.
Email stefan@chaos.holdings. Approved bios, host intros, headshots, and show-notes wording are in his full press and speaker kit on the Whitwell & Co. site.
Last updated October 13, 2026. These appearances are general educational conversations. They are not investment, tax, legal, or compliance advice. The shows and their hosts are independent of Chaos Holdings, LLC; episode titles are the shows' own, and some episodes were recorded years ago and reflect conditions at that time. Stefan is also founder, CEO, and Chief Investment Officer of Whitwell & Co., LLC, an SEC-registered investment adviser. Chaos Holdings, LLC is a separate company and does not provide investment advice. CFA®, Chartered Financial Analyst®, and CIPM® are registered trademarks owned by CFA Institute.