Planting the Orange Flag

Planting the Orange Flag

Author: Wyatt O'Rourke & Jordan Guess December 10, 2025 Duration: 1:00:42

What happens when financial advisors dismiss Bitcoin as a passing trend, only to watch clients walk away? How do you build trust in an industry riddled with scams and short-term thinking?

In this first episode of BfFS, we explore the gaps in traditional finance, where fear meets opportunity, and what it means to "Plant the Orange Flag" as a professional.
From tax strategies to custody tradeoffs, the rules are being rewritten. Will you adapt or get left behind?

Chapters
00:00:00 Welcome to Bitcoin for Financial Services
00:03:11 Wyatt O'Rourke: Basilic Financial background
00:05:52 Jordan Guess: CPA and Bitment introduction
00:08:41 Origin story: how we met and teamed up
00:12:39 Planning and running the inaugural summit
00:23:49 Why advisors must embrace Bitcoin now
00:30:50 Business model shifts and custody questions
00:36:12 Due diligence for Bitcoin service providers
00:46:12 Podcast details and community building
00:57:14 Events, announcements, and closing statements

Host Links
Jordan Guess:
X: https://x.com/jordanguess
Discord: https://discord.com/invite/Xg55GVkc3f

**Wyatt O'Rourke:
**X: https://x.com/wyattorourke_
Website: https://www.basilic.io/

**Bitcoin for Financial Services Media Links:
**X: https://x.com/BFFS_media
Website: https://bffs.media/
YouTube: http://www.youtube.com/@BFFS_Media

Check out our awesome show sponsors!

  • Basilic Financial: Your wealth deserves intention. Basilic Financial is a Bitcoin-focused wealth management firm that helps clients find balance between money and meaning. Basilic integrates sound‑money strategies across four personalized services: financial planning, individual wealth management, retirement services for SMBs, and Bitcoin financial services. https://www.basilic.io/
  • Bitment: Tired of messy CSVs and broken cost basis? Bitment is the first Bitcoin-native accounting platform for CPAs, advisors, miners, and serious investors, delivering clean Bitcoin bank statements, reliable cost tracking, full reporting, and seamless fiat integration through Plaid. Ditch the headaches with robust accounting for the hardest money on earth. https://www.bitment.co/
  • Satoshi Pacioli: Run a Bitcoin business? Meet your full-service accounting and tax partner built for the Bitcoin economy. Satoshi Pacioli handles bookkeeping, financial reporting, tax compliance, and strategic planning for companies and individuals. Work with advisors who speak Bitcoin and keep you compliant while building long-term value. https://satoshipacioli.com/

You’ll find Bitcoin for Financial Services Podcast lives at the intersection of established finance and a rapidly evolving digital asset landscape. Hosts Wyatt O’Rourke and Jordan Guess bring distinct, grounded perspectives to each conversation. Wyatt, author of The Bitcoinization of Finance and founder of Basilic Financial, operates daily in the practical work of connecting traditional wealth management with Bitcoin’s emerging economy. Jordan’s complementary expertise allows them to dissect complex developments with clarity. Together, they move beyond hype to examine the tangible mechanisms, regulatory shifts, and institutional adoption that are actively restructuring financial services. This isn't about abstract theory; it's a close look at the tools, strategies, and real-world implications for professionals and serious investors. Each episode of this podcast feels like a focused discussion, unpacking how Bitcoin technology influences everything from portfolio construction to payment systems. If you're navigating the convergence of legacy systems and cryptographic innovation, the dialogue here provides a necessary and nuanced compass. Tune in for analysis that respects the depth of both finance and the foundational technology changing it.
Author: Language: English Episodes: 22

Bitcoin for Financial Services Podcast
Podcast Episodes
1 Billion Users: Why the Lightning Network is Winning [not-audio_url] [/not-audio_url]

Duration: 48:18
We sit down with Lightning Network executive Bobby Shell to explore how Bitcoin is maturing from a tinkerer's hobby into an essential enterprise powerhouse. We break down the massive shift in payment rails, revealing how…
Mortgage Insider: Use Your Bitcoin To Qualify Now! [not-audio_url] [/not-audio_url]

Duration: 52:31
We explore a massive breakthrough for Bitcoiners looking to enter the real estate market. For years, traditional banks have forced us to liquidate our stack or denied loans because our wealth is not in fiat. In this epis…
Why Your Business Needs An Anti-CBDC Strategy Now [not-audio_url] [/not-audio_url]

Duration: 59:50
In this episode, we sit down with Adam Simecka to discuss the critical importance of building tools for independent value transfer in an increasingly surveilled world. We explore why self-custody is the only true protect…
Why 99% of Advisors Will Be Unemployed in 3 Years [not-audio_url] [/not-audio_url]

Duration: 1:08:45
We sat down with Zach Wischler, Director of Sales at Casa, to dismantle the false security of the ETF narrative and explore the future of wealth preservation. While Wall Street pushes paper Bitcoin, the real value for hi…
CFO Reveals the 4 Types of Bitcoin Treasuries [not-audio_url] [/not-audio_url]

Duration: 1:01:52
We sit down with Travis MacDonald, a CPA and CFA who left the traditional M&A world to build financial infrastructure for the Bitcoin economy. He breaks down why the Bitcoin Treasury narrative is often oversimplified and…
Profitable Businesses Choose Bitcoin [not-audio_url] [/not-audio_url]

Duration: 56:49
In this episode, we sit down with Brandon Karpeles of Sovereign to unpack why so many businesses are failing under leverage and why Bitcoin changes that equation. Brandon shares his journey out of traditional finance, wh…
Building Bitcoin Rails For HSAs [not-audio_url] [/not-audio_url]

Duration: 52:35
We sat down with Jon Gordon and Stuart Lackey, co-founders of SoundHSA, to unpack why healthcare costs keep rising, why patients rarely see real prices, and where incentives break when third parties sit between doctors a…
The Fiduciary Case for Bitcoin Allocation [not-audio_url] [/not-audio_url]

Duration: 54:09
In this episode, we sit down with Jirayr, co-founder of Citrin Capital Advisors, to discuss the evolution of a San Francisco-based wealth management firm integrating Bitcoin. We explore the critical comparison between tr…
Bitcoin for Business in Practice [not-audio_url] [/not-audio_url]

Duration: 51:53
In this episode, we sit down with Wesley Schlemmer, President of the Bitcoin Bay Foundation and Executive Director of the Florida Blockchain Business Association. Wesley shares how Florida’s Bitcoin ecosystem has grown f…
Building Intentional Wealth [not-audio_url] [/not-audio_url]

Duration: 1:07:12
In this third episode of BfFS, we sit down with Jim Crider to explore what it means to build intentional wealth in the Bitcoin era. When does Bitcoin belong in an allocation, and when is holding dollars the responsible c…