Bitcoin for Financial Services Podcast

State regulators may be far more relaxed about Bitcoin in client portfolios than the federal headlines suggest.

Jordan and Wyatt sit down with Mark Dempsey, founder of Crypto Regulatory Solutions. Mark started at FINRA, became chief compliance officer for Navy Federal’s RIA and broker-dealer, and now advises Bitcoin-focused investment advisors and funds. He explains how regulators treat Bitcoin as one more asset class under fiduciary duty, why documentation matters more than the allocation percentage, and what the Cold Card failure means for vendor due diligence and disclosure. They also cover the Clarity Act, the de minimis tax exemption, mining revenue recognition, why the states may move first, KYC/AML and the “honeypot” problem, offshore fund structures, Choke Point 2.0 and debanking, and whether advisors are hiding behind a narrow reading of fiduciary duty.

🎟️ Join Us in Denver, Bitcoin Financial Services Summit

October 20-22, Denver, Colorado. RIAs, CPAs, lenders, miners, treasury companies, and Bitcoin-native operators all in one room. Get your tickets at bffs.media

Guest: Mark Dempsey

Crypto Regulatory Solutions

Website: cryptoregulatorysolutions.com

Host Links

Wyatt O’Rourke

X: x.com/wyattorourke

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors

Unchained Capital

@unchained — bitcoin custody, loans, and IRAs, built so you keep your keys. unchained.com

Sound HSA

@SOUND_HSA — the first bitcoin-native HSA. Save tax-free, grow in bitcoin. soundhsa.com

River Financial

@River — bitcoin-only brokerage, full-reserve custody, zero fees on recurring buys. river.com

Quantify Funds

Asset manager behind the STKd ETF suite, including BTGD — 100% bitcoin and 100% gold exposure. quantifyfunds.com

Falcon, Rappaport & Berkman

@frblaw (LinkedIn) — the law firm behind FRB’s Digital Assets Practice Group. frblaw.com

SustainHash

@SustainHash — a one-stop solution for bitcoin miners, from ASIC hardware to site deployment and repairs. sustainhash.com

Abundant Mines

@AbundantMines — fully managed, hydro-powered bitcoin mining where you own the miners and keep 100% of the bitcoin. abundantmines.com

Stormrake

@Stormrake — full-service digital asset brokerage with a dedicated broker for every client. stormrake.com

Revolution Mortgage

@RevolutionMortgage — modern home lending for bitcoin-forward households, with loan officers who understand balance sheets that include bitcoin. revolutionmortgage.com

Anchorage Digital

@Anchorage — home to Anchorage Digital Bank, the only federally chartered crypto bank in the US. anchorage.com

UTXO Management

@UTXOManagement — bitcoin-native asset management and research across public markets, venture capital, and structured credit. utxo.management

SALT Lending

Bitcoin-backed loans since 2016. Access cash without selling your bitcoin. saltlending.com

Bitcoin Well

Bitcoin Well (TSXV: BTCW) — buy real bitcoin sent directly to your own wallet, across Canada and all 50 US states. bitcoinwell.com

AnchorWatch

Bitcoin custody and insurance, with multi-party vaults and optional Lloyd’s of London coverage. anchorwatch.com

2718 Fund

2718 Capital — a private fund for accredited investors that stays long bitcoin and targets a 10% annual distribution, paid monthly. Distributions are not guaranteed; leverage adds risk. 2718.fund

Snorkel

Handcrafted cedar hot tubs and cold plunges from the Pacific Northwest since 1979. Hosting the bar and backyard patio at the Summit. snorkel.com

Over $200 billion sits in HSAs, and more than half of it is in cash. What if that money were Bitcoin, tax-free in and out?

Wyatt sits down with Jon Gordon, co-founder of Sound HSA and our first recurring guest, to unpack how real Bitcoin goes inside the most tax-advantaged account in the US tax code: tax-free in, tax-free growth, and no capital gains on eligible health spending. They cover the new employer rollout built on payroll integrations, multisig custody with Unchained, Gannett Trust, and Horizon Trust, and where in-kind Bitcoin distributions are headed.

They also get into sats for steps, including 21,000 sats for 21,000 steps at the Summit, and how Jon is building the Chicago Bitcoin Collective and Forking Coin restaurant. Plus: Illinois's new 0.2% crypto transaction tax, and a local doctor whose patients are already paying in Bitcoin.

🎟️ Join Us in Denver, Bitcoin Financial Services Summit

October 20-22, Denver, Colorado. RIAs, CPAs, lenders, miners, treasury companies, and Bitcoin-native operators all in one room. Get your tickets at bffs.media

Guest: Jon Gordon

Sound HSA

Website: soundhsa.com

Email: [email protected]

X: Bitcoin Yogi

Host Links

Wyatt O'Rourke

X: x.com/wyattorourke

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors

Unchained Capital

@unchained — bitcoin custody, loans, and IRAs, built so you keep your keys. unchained.com

Sound HSA

@SOUND_HSA — the first bitcoin-native HSA. Save tax-free, grow in bitcoin. soundhsa.com

River Financial

@River — bitcoin-only brokerage, full-reserve custody, zero fees on recurring buys. river.com

Quantify Funds

Asset manager behind the STKd ETF suite, including BTGD — 100% bitcoin and 100% gold exposure. quantifyfunds.com

Falcon, Rappaport & Berkman

@frblaw (LinkedIn) — the law firm behind FRB's Digital Assets Practice Group. frblaw.com

SustainHash

@SustainHash — a one-stop solution for bitcoin miners, from ASIC hardware to site deployment and repairs. sustainhash.com

Abundant Mines

@AbundantMines — fully managed, hydro-powered bitcoin mining where you own the miners and keep 100% of the bitcoin. abundantmines.com

Stormrake

@Stormrake — full-service digital asset brokerage with a dedicated broker for every client. stormrake.com

Revolution Mortgage

@RevolutionMortgage — modern home lending for bitcoin-forward households, with loan officers who understand balance sheets that include bitcoin. revolutionmortgage.com

Anchorage Digital

@Anchorage — home to Anchorage Digital Bank, the only federally chartered crypto bank in the US. anchorage.com

UTXO Management

@UTXOManagement — bitcoin-native asset management and research across public markets, venture capital, and structured credit. utxo.management

SALT Lending

Bitcoin-backed loans since 2016. Access cash without selling your bitcoin. saltlending.com

Bitcoin Well

Bitcoin Well (TSXV: BTCW) — buy real bitcoin sent directly to your own wallet, across Canada and all 50 US states. bitcoinwell.com

AnchorWatch

Bitcoin custody and insurance, with multi-party vaults and optional Lloyd's of London coverage. anchorwatch.com

2718 Fund

2718 Capital — a private fund for accredited investors that stays long bitcoin and targets a 10% annual distribution, paid monthly. Distributions are not guaranteed; leverage adds risk. 2718.fund

Snorkel

Handcrafted cedar hot tubs and cold plunges from the Pacific Northwest since 1979. Hosting the bar and backyard patio at the Summit. snorkel.com

Buying Bitcoin gives you zero tax advantage. Mining it, done right, can cut your cost basis in half — and write off nearly every dollar along the way.

Jordan sits down with Paul Palmer, Chief Revenue Officer at Sustain Hash, a full-service Bitcoin mining operator that's scaled from 5 megawatts to 130 megawatts across Alberta, Texas, Iowa, and Kansas in just three years. Paul — a 30-year veteran of financial services and payments who spent time as an RIA himself — breaks down exactly how mining companies help family offices and high-net-worth individuals turn dollars into Bitcoin at a real discount: buying miners, containers, and electricity contracts, all of which are 100% deductible in year one under current tax law, versus a straight exchange purchase that offers no tax benefit at all.

Paul walks through the mechanics that make this work: the difference between on-grid mining (soaking up stranded utility power, with curtailment agreements that let operators instantly power down during storms and get paid to do it) versus off-grid gas mining (converting flared methane into electricity instead of wasting it), and why Bitcoin miners — unlike AI or HPC data centers — are uniquely "pro-consumer" because they can shut off in real time when the grid needs the power back. He gets into the actual math behind mining economics (hash rate, difficulty adjustment, joules per terahash), the operational details that separate profitable sites from money-losing ones (on-site repair inventory, uptime strategy, insurance structuring), and the real-world joint venture structures where Bitcoin believers pair with hard-asset investors to split the economics. Paul closes with a clear framework for advisors: when a client wants to go beyond a simple hosted-mining setup, and what the introduction and handoff process actually looks like.

Starting this week, we're continuing our run of episodes featuring speakers from the Bitcoin Financial Services Summit — leading up to October, we'll bring you conversations with the RIAs, CPAs, miners, and operators on stage in Denver.

🎟️ Join Us in Denver, Bitcoin Financial Services Summit

October 20-22, Denver, Colorado. RIAs, CPAs, lenders, miners, treasury companies, and Bitcoin-native operators all in one room. Get your tickets at bffs.media

Guest: Paul Palmer

Sustain Hash

Website: sustainhash.com

Email: [email protected]

Host Links

Wyatt O'Rourke

X: x.com/wyattorourke

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors

Basilic Financial: Bitcoin-focused wealth management — financial planning, individual wealth management, retirement services for SMBs. basilic.io

Bitment: The first Bitcoin-native accounting platform for CPAs, advisors, miners, and investors. Clean statements, cost tracking, reporting, Plaid integration. bitment.co

Satoshi Pacioli: Full-service accounting and tax partner for the Bitcoin economy. satoshipacioli.com

Partners

Unchained Capital: Collaborative multisig custody, bitcoin-backed loans, trading desk, and bitcoin IRAs — while you keep control of your keys. unchained.com

Sound HSA: The first bitcoin-native Health Savings Account — triple-tax-advantaged HSA benefits with real bitcoin holdings. soundhsa.com

River Financial: Bitcoin-only brokerage — full-reserve custody, zero-fee recurring buys, interest-bearing cash account paid in bitcoin. river.com

Quantify Funds: Asset manager behind the STKd ETF suite, including BTGD — 100% bitcoin and 100% gold exposure. quantifyfunds.com

Revolution Mortgage: Nationwide lender — FHA, VA, USDA, and conventional loans, tech-driven for lower rates and faster closings. revolutionmortgage.com

Anchorage Digital: The only federally chartered digital asset bank in the US — institutional-grade bitcoin custody, trading, settlement, and financing. anchorage.com

UTXO Management: Bitcoin-native investment firm allocating across public markets, venture capital, and structured credit, backed by institutional research. A subsidiary of Nakamoto Inc. (NASDAQ: NAKA), UTXO advises 210k Capital and a family of funds built on the thesis that the bitcoin ecosystem is an investable asset class in its own right. utxo.com

Cash App made almost 10% routing Lightning payments. Most advisors have no idea how, or why that number is real.

Jordan and Wyatt sit down with Chris Ritter, Chief Strategy Officer at Zeus, whose path to Bitcoin ran through a decade coaching Olympic swimmers, a business exit, and a return to school for a master's in finance and a background in computer science before landing at Zeus and co-authoring the Lightning Economics Report with Axiom — 98 sources spanning a century of monetary history. Chris breaks down Lightning as the third major avenue for putting Bitcoin to work (after miner derivatives and MicroStrategy-style digital credit), and unpacks the metric that makes it unique: velocity. Zeus's own node saw Bitcoin turn over 64 times in a trailing 12 months — a number with no real precedent in traditional finance, where the same yield would require 10x bank leverage.

They get into how Lightning's fee-times-velocity model produces real, explainable 3-5% Bitcoin-native yield without giving up custody — thanks to an architecture (built on LDK and the Validating Lightning Signer) that separates the signing keys from the node itself, meaning even a compromised node can't result in stolen funds, only downtime. Chris walks through the "promises vs. conditions" framework for evaluating any Bitcoin yield product, addresses the Cold Card fallout head-on with a breakdown of realistic attack vectors and force-closure mechanics, and makes the case for why Lightning's growing institutional volume (payments now averaging $100-250, not coffee-sized) signals it's finally mature enough for serious capital. He closes with where agentic AI payments fit into Lightning's future — and why getting the risk architecture right matters more than chasing the next narrative.

We're continuing our run of episodes featuring speakers from the Bitcoin Financial Services Summit — leading up to October, we'll bring you conversations with the RIAs, CPAs, miners, and operators on stage in Denver.

🎟️ Join Us in Denver, Bitcoin Financial Services Summit

October 20-22, Denver, Colorado. RIAs, CPAs, lenders, miners, treasury companies, and Bitcoin-native operators all in one room. Get your tickets at bffs.media

Guest: Chris Ritter

Zeus

X: x.com/freecritterxyz

Host Links

Wyatt O'Rourke

X: x.com/wyattorourke

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors

Basilic Financial: Bitcoin-focused wealth management — financial planning, individual wealth management, retirement services for SMBs. basilic.io

Bitment: The first Bitcoin-native accounting platform for CPAs, advisors, miners, and investors. Clean statements, cost tracking, reporting, Plaid integration. bitment.co

Satoshi Pacioli: Full-service accounting and tax partner for the Bitcoin economy. satoshipacioli.com

Partners

Unchained Capital: Collaborative multisig custody, bitcoin-backed loans, trading desk, and bitcoin IRAs — while you keep control of your keys. unchained.com

Sound HSA: The first bitcoin-native Health Savings Account — triple-tax-advantaged HSA benefits with real bitcoin holdings. soundhsa.com

River Financial: Bitcoin-only brokerage — full-reserve custody, zero-fee recurring buys, interest-bearing cash account paid in bitcoin. river.com

Quantify Funds: Asset manager behind the STKd ETF suite, including BTGD — 100% bitcoin and 100% gold exposure. quantifyfunds.com

Revolution Mortgage: Nationwide lender — FHA, VA, USDA, and conventional loans, tech-driven for lower rates and faster closings. revolutionmortgage.com

Anchorage Digital: The only federally chartered digital asset bank in the US — institutional-grade bitcoin custody, trading, settlement, and financing. anchorage.com

UTXO Management: Bitcoin-native investment firm allocating across public markets, venture capital, and structured credit, backed by institutional research. A subsidiary of Nakamoto Inc. (NASDAQ: NAKA), UTXO advises 210k Capital and a family of funds built on the thesis that the bitcoin ecosystem is an investable asset class in its own right. utxo.com

What if you could get Bitcoin exposure with your downside covered by real estate… and never make an interest payment?

Jordan and Wyatt sit down with Daniel Holbrook, managing partner at BitHedge, a former 15-year commercial real estate entrepreneur who fully rotated into Bitcoin in early 2025 after realizing real estate's best properties, store of value, scarcity, structural upside, were all better expressed on-chain. Daniel walks through his own path from crypto-curious in 2020 to Bitcoin-only within weeks of serious study, and why he sold most of his real estate portfolio once he ran the numbers on rising debt costs, insurance spikes, and flat rents against Bitcoin's asymmetric setup.

They dig into the mechanics of BitHedge, a three-party structured fund that pairs capital investors seeking downside-protected Bitcoin exposure with real estate owners willing to pledge ultra-conservative (sub-50% LTV) equity positions in exchange for a share of Bitcoin's upside — no interest, no debt, no forced sale. Daniel breaks down why real estate is a better collateral pairing for Bitcoin than gold, how the fund's payout structure works if Bitcoin doubles (or goes to zero), and why jurisdictional and title-enforcement risk make some states a non-starter for the fund's real estate pledges. He also addresses the Cold Card fallout directly, walking through why Anchorage Digital's multi-signer custody model with no single point of failure matters more than ever, and makes the case for why now — mid-bear-market, adoption curve just turning upward — is exactly the right time for real estate owners to put idle equity to work.

Starting this week, we're continuing our run of episodes featuring speakers from the Bitcoin Financial Services Summit — leading up to October, we'll bring you conversations with the RIAs, CPAs, miners, and operators on stage in Denver.

🎟️ Join Us in Denver, Bitcoin Financial Services Summit

October 20-22, Denver, Colorado. RIAs, CPAs, lenders, miners, treasury companies, and Bitcoin-native operators all in one room. Get your tickets at bffs.media

Guest: Daniel Holbrook

BitHedge

Website: bithedge.fund

LinkedIn: Daniel Holbrook

Host Links

Wyatt O'Rourke

X: x.com/wyattorourke

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors

Basilic Financial: Bitcoin-focused wealth management — financial planning, individual wealth management, retirement services for SMBs. basilic.io

Bitment: The first Bitcoin-native accounting platform for CPAs, advisors, miners, and investors. Clean statements, cost tracking, reporting, Plaid integration. bitment.co

Satoshi Pacioli: Full-service accounting and tax partner for the Bitcoin economy. satoshipacioli.com

Partners

Unchained Capital: Collaborative multisig custody, bitcoin-backed loans, trading desk, and bitcoin IRAs — while you keep control of your keys. unchained.com

Sound HSA: The first bitcoin-native Health Savings Account — triple-tax-advantaged HSA benefits with real bitcoin holdings. soundhsa.com

River Financial: Bitcoin-only brokerage — full-reserve custody, zero-fee recurring buys, interest-bearing cash account paid in bitcoin. river.com

Quantify Funds: Asset manager behind the STKd ETF suite, including BTGD — 100% bitcoin and 100% gold exposure. quantifyfunds.com

Revolution Mortgage: Nationwide lender — FHA, VA, USDA, and conventional loans, tech-driven for lower rates and faster closings. revolutionmortgage.com

Anchorage Digital: The only federally chartered digital asset bank in the US — institutional-grade bitcoin custody, trading, settlement, and financing. anchorage.com

This episode was already on the calendar — then the worst-case self-custody scenario happened days before we hit record.

Jordan and Wyatt sit down with Chantel Lillycrop-Kostiuk, VP of Operations at Bitcoin Well, days after a critical entropy bug in Cold Card hardware wallets left seed phrases guessable and drained hundreds of Bitcoin from users who thought they were following best practice. Chantel walks through Bitcoin Well's response in real time — from spotting the first Reddit and X posts, to a 70,000-person customer email sent at 10pm the night the bug went public, to fielding three-hour calls with panicked Bitcoin Well Infinite clients migrating their life savings off compromised devices.

They get into why CoinKite's delayed and inconsistent disclosure did more damage than the bug itself, why self-custody isn't dead but needs to evolve toward better UX and collaborative custody models, and how AI-driven identity fraud (voice cloning, deepfakes) is forcing OTC desks to rethink verification beyond "does this sound like my client." Chantel also breaks down the Bitcoin Family Office Group — the joint venture connecting Bitcoin Well, tax, legal, and mining-depreciation expertise for clients in the $5-50M net worth range — and closes with a clear-eyed comparison to FTX and Mt. Gox: this was a hardware failure, not a Bitcoin failure, and the lesson is the same one it's always been — trust, but verify.

Starting this week, we're continuing our run of episodes featuring speakers from the Bitcoin Financial Services Summit — leading up to the event in October, we'll be bringing you conversations with the RIAs, CPAs, miners, and operators who'll be on stage in Denver.

🎟️ Join Us in Denver, Bitcoin Financial Services Summit

The Bitcoin Financial Services Summit returns October 20-22 in Denver, Colorado. RIAs, CPAs, lenders, miners, treasury companies, and Bitcoin-native operators all in one room. If you want to understand where Bitcoin and finance is going next, this is where you need to be. Get your tickets at bffs.media

Guest: Chantel Lillycrop-Kostiuk

Bitcoin Well

Website: bitcoinwell.com/infinite

Host Links

Wyatt O'Rourke

X: x.com/wyattorourke_

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors

Basilic Financial: Your wealth deserves intention. Basilic is a Bitcoin-focused wealth management firm helping clients find balance between money and meaning. Financial planning, individual wealth management, retirement services for SMBs, and Bitcoin financial services. 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. Clean Bitcoin bank statements, reliable cost tracking, full reporting, and seamless fiat integration through Plaid. bitment.co

Satoshi Pacioli: Run a Bitcoin business? Meet your full-service accounting and tax partner built for the Bitcoin economy. Bookkeeping, financial reporting, tax compliance, and strategic planning for companies and individuals who speak Bitcoin. satoshipacioli.com

Partners

Unchained Capital: Not your keys, not your bitcoin? Unchained is a bitcoin financial services company offering collaborative multisig custody, bitcoin-backed loans, a trading desk, and bitcoin IRAs — all while you keep control of your keys. unchained.com

Sound HSA: Why let your health savings sit in cash? Sound HSA is the first bitcoin-native Health Savings Account, combining triple-tax-advantaged HSA benefits with real bitcoin holdings, automated tax docs, and a receipt vault for medical expenses. soundhsa.com

River Financial: Want a bitcoin-only brokerage built for the long haul? River offers full-reserve custody, zero-fee recurring buys, and an interest-bearing cash account that pays out in bitcoin. river.com

Quantify Funds: Looking to stack scarcity assets? Quantify Funds is the asset management firm behind the STKd suite of ETFs, including BTGD — the first ETF combining 100% bitcoin and 100% gold exposure. quantifyfunds.com

Revolution Mortgage: Buying a home or refinancing? Revolution Mortgage is a nationwide lender offering FHA, VA, USDA, and conventional loans, with a tech-driven process built for lower rates and faster closings. revolutionmortgage.com

Anchorage Digital: Need a qualified custodian that satisfies regulators, auditors, and IPS language? Anchorage Digital is the only federally chartered digital asset bank in the US, offering institutional-grade bitcoin custody, trading, settlement, and financing built for funds, RIAs, and corporate treasuries. anchorage.com

Bitcoin Sports Network: Relationships in this industry get built on the course, not in a webinar. Bitcoin Sports Network fuels the bitcoin lifestyle through championship golf tournaments and community experiences worldwide, plus weekly content on Golf BSN featuring tournament highlights, player stories, and the bitcoin golf nomad lifestyle. bitcoinsports.network

Most real estate owners have never heard of a dual-collateralized Bitcoin loan — but the ones who have are getting better rates, longer holding periods, and a hedge their neighbors don't have.

Jordan and Wyatt sit down with Chris Drzyzga, Senior VP and Principal at Voit Real Estate Services, to unpack how a 15-year commercial real estate veteran ended up building a live, transparent case study on integrating Bitcoin into property treasury, capital stacks, and operations. Chris walks through why orange-pilling real estate owners has been harder than expected despite the obvious parallel (fiat into sound money vs. fiat into hard assets), how tax-free refinance proceeds can fund a Bitcoin treasury without triggering a taxable event, and why the wash sale rule doesn't apply to property-classified Bitcoin holdings.

They also get into the operational side: using Bitcoin mining to heat buildings and cut energy costs (which run ~30% of opex), the difference between mining to subsidize expenses vs. mining to maximize output, and why private family offices — not REITs or institutions — are best positioned to move first. Chris closes with his own metric, satoshis per square foot, for comparing properties through a Bitcoin lens, and makes the case for why some assets should be sold outright rather than "Bitcoin-ified."

Starting this week, we're continuing our run of episodes featuring speakers from the Bitcoin Financial Services Summit — leading up to the event in October, we'll be bringing you conversations with the RIAs, CPAs, miners, and operators who'll be on stage in Denver.

🎟️ Join Us in Denver, Bitcoin Financial Services Summit

The Bitcoin Financial Services Summit returns October 20-22 in Denver, Colorado. RIAs, CPAs, lenders, miners, treasury companies, and Bitcoin-native operators all in one room. If you want to understand where Bitcoin and finance is going next, this is where you need to be. Get your tickets at bffs.media

Guest: Chris Drzyzga

Voit Real Estate Services

Podcast: The Real Estate Standard

X: x.com/chrisdriz

Website: chrisdrizga.com

Host Links

Wyatt O'Rourke

X: x.com/wyattorourke_

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors

Basilic Financial: Your wealth deserves intention. Basilic is a Bitcoin-focused wealth management firm helping clients find balance between money and meaning. Financial planning, individual wealth management, retirement services for SMBs, and Bitcoin financial services. 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. Clean Bitcoin bank statements, reliable cost tracking, full reporting, and seamless fiat integration through Plaid. bitment.co

Satoshi Pacioli: Run a Bitcoin business? Meet your full-service accounting and tax partner built for the Bitcoin economy. Bookkeeping, financial reporting, tax compliance, and strategic planning for companies and individuals who speak Bitcoin. satoshipacioli.com

Partners

Unchained Capital: Not your keys, not your bitcoin? Unchained is a bitcoin financial services company offering collaborative multisig custody, bitcoin-backed loans, a trading desk, and bitcoin IRAs — all while you keep control of your keys. unchained.com

Sound HSA: Why let your health savings sit in cash? Sound HSA is the first bitcoin-native Health Savings Account, combining triple-tax-advantaged HSA benefits with real bitcoin holdings, automated tax docs, and a receipt vault for medical expenses. soundhsa.com

River Financial: Want a bitcoin-only brokerage built for the long haul? River offers full-reserve custody, zero-fee recurring buys, and an interest-bearing cash account that pays out in bitcoin. river.com

Quantify Funds: Looking to stack scarcity assets? Quantify Funds is the asset management firm behind the STKd suite of ETFs, including BTGD — the first ETF combining 100% bitcoin and 100% gold exposure. quantifyfunds.com

Revolution Mortgage: Buying a home or refinancing? Revolution Mortgage is a nationwide lender offering FHA, VA, USDA, and conventional loans, with a tech-driven process built for lower rates and faster closings. revolutionmortgage.com

Anchorage Digital: Need a qualified custodian that satisfies regulators, auditors, and IPS language? Anchorage Digital is the only federally chartered digital asset bank in the US, offering institutional-grade bitcoin custody, trading, settlement, and financing built for funds, RIAs, and corporate treasuries. anchorage.com

Bitcoin Sports Network: Relationships in this industry get built on the course, not in a webinar. Bitcoin Sports Network fuels the bitcoin lifestyle through championship golf tournaments and community experiences worldwide, plus weekly content on Golf BSN featuring tournament highlights, player stories, and the bitcoin golf nomad lifestyle. bitcoinsports.network

Most people think of Bitcoin onboarding as either "buy an ETF" or "run your own node" — Stephen Cole, co-founder of Castle, is building the entire financial stack in between.

Jordan and Wyatt sit down with Stephen to talk through Castle's journey from an automation-first on-ramp called Orchestra to a full Bitcoin-powered financial stack for businesses — cash accounts, revenue-percentage Bitcoin buys, and now high-yield exposure through Strategy's STRC. They dig into why Castle went to market with business entities first, how KYB compliance shapes onboarding, and why personal accounts are now opening up to retail individuals for the first time.

Stephen breaks down Castle's custody model with BitGo, why self-custody is always the goal but never the barrier to entry, and how the platform is quietly building treasury management tools — multi-sig-style approvals, permissioned roles, and governance — for businesses that want Bitcoin-native financial infrastructure without the operational headache. They also get into the STRC debate, stablecoins' place in a Bitcoin-first stack, and why Stephen thinks the term "Bitcoin treasury company" needs a much bigger tent than Wall Street headlines suggest.

Starting this week, we're kicking off a run of episodes featuring speakers from the Bitcoin Financial Services Summit — leading up to the event in October, we'll be bringing you conversations with the RIAs, CPAs, miners, and operators who'll be on stage in Denver.

🎟️ Join Us in Denver, Bitcoin Financial Services Summit

The Bitcoin Financial Services Summit returns October 20-22 in Denver, Colorado. RIAs, CPAs, lenders, miners, treasury companies, and Bitcoin-native operators all in one room. If you want to understand where Bitcoin and finance is going next, this is where you need to be. Get your tickets at bffs.media

Guest: Stephen Cole

Castle

Website: savewithcastle.com

Host Links

Wyatt O'Rourke

X: x.com/wyattorourke_

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors

Basilic Financial: Your wealth deserves intention. Basilic is a Bitcoin-focused wealth management firm helping clients find balance between money and meaning. Financial planning, individual wealth management, retirement services for SMBs, and Bitcoin financial services. 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. Clean Bitcoin bank statements, reliable cost tracking, full reporting, and seamless fiat integration through Plaid. bitment.co

Satoshi Pacioli: Run a Bitcoin business? Meet your full-service accounting and tax partner built for the Bitcoin economy. Bookkeeping, financial reporting, tax compliance, and strategic planning for companies and individuals who speak Bitcoin. satoshipacioli.com

Unchained Capital: Not your keys, not your bitcoin? Unchained is a bitcoin financial services company offering collaborative multisig custody, bitcoin-backed loans, a trading desk, and bitcoin IRAs — all while you keep control of your keys. unchained.com

Sound HSA: Why let your health savings sit in cash? Sound HSA is the first bitcoin-native Health Savings Account, combining triple-tax-advantaged HSA benefits with real bitcoin holdings, automated tax docs, and a receipt vault for medical expenses. soundhsa.com

River Financial: Want a bitcoin-only brokerage built for the long haul? River offers full-reserve custody, zero-fee recurring buys, and an interest-bearing cash account that pays out in bitcoin. river.com

Quantify Funds: Looking to stack scarcity assets? Quantify Funds is the asset management firm behind the STKd suite of ETFs, including BTGD — the first ETF combining 100% bitcoin and 100% gold exposure. quantifyfunds.com

Revolution Mortgage: Buying a home or refinancing? Revolution Mortgage is a nationwide lender offering FHA, VA, USDA, and conventional loans, with a tech-driven process built for lower rates and faster closings. revolutionmortgage.com

Kendall Weihe, Jordan's co-founder at Bitment, joins the pod for a rare deep dive into what actually changed in software engineering — and by extension, financial services — over the last 12 months.

Kendall walks through his path from a corporate software engineering job at KFC to Coinmetrics (Nick Carter's data analytics company), to Jack Dorsey's Block, where he worked on the TBDEX decentralized exchange protocol, and finally into stablecoins before going all-in on Bitment. Along the way: why cold emails still work, why he thinks the "VC talking his book" critique of Nick Carter misses the point, and what it was actually like spending two days a year frying chicken as a corporate KFC policy.

The back half is the real meat: Kendall argues that since roughly December 2025, AI coding tools have fundamentally changed what it means to build software — he barely writes or reads code anymore, and instead manages AI agents the way he'd manage employees. He breaks down why software was ground zero for this shift (Linux standardization, decades of developers automating their own jobs) while human systems like finance, law, and government will take much longer to diffuse. He also makes the case for vibe coding as a communication tool rather than a shortcut, uses a "skyscraper" analogy for why AI-assisted engineering is still laborious, and lays out his vertical-vs-horizontal, diffusion-vs-standardization framework for what a real AI-native operating system for financial services actually requires.

Chapters

00:00 Introduction

01:35 How Kendall and Jordan Met

03:22 Kendall's Background: KFC to Coinmetrics to Block

06:27 Inside TBDEX: Building a Decentralized Exchange at Block

08:56 The KFC Colonel Question

10:35 Cold Emails and Getting Into Coinmetrics

12:46 Is Nick Carter Misunderstood?

16:07 Double-Entry Bookkeeping, Bitcoin, and AI for Financial Advisors

22:03 "Learn to Code" Aged Poorly: AI and the Disruption of Software Engineering

28:35 Vibe Coding: Powerful Tool, Dangerous Shortcut

33:41 The Skyscraper Theory of AI-Assisted Engineering

36:38 Diffusion vs. Standardization: Decentralizing Big Tech

43:56 Vertical vs. Horizontal: What It Takes to Build an AI-Native OS

47:40 Closing Thoughts

Host Links

Wyatt O'Rourke

X: x.com/wyattorourke_

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors

Basilic Financial: Your wealth deserves intention. Basilic is a Bitcoin-focused wealth management firm helping clients find balance between money and meaning. Financial planning, individual wealth management, retirement services for SMBs, and Bitcoin financial services. 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. Clean Bitcoin bank statements, reliable cost tracking, full reporting, and seamless fiat integration through Plaid. bitment.co

Satoshi Pacioli: Run a Bitcoin business? Meet your full-service accounting and tax partner built for the Bitcoin economy. Bookkeeping, financial reporting, tax compliance, and strategic planning for companies and individuals who speak Bitcoin. satoshipacioli.com

Unchained Capital: Not your keys, not your bitcoin? Unchained is a bitcoin financial services company offering collaborative multisig custody, bitcoin-backed loans, a trading desk, and bitcoin IRAs — all while you keep control of your keys. unchained.com

Sound HSA: Why let your health savings sit in cash? Sound HSA is the first bitcoin-native Health Savings Account, combining triple-tax-advantaged HSA benefits with real bitcoin holdings, automated tax docs, and a receipt vault for medical expenses. soundhsa.com

River Financial: Want a bitcoin-only brokerage built for the long haul? River offers full-reserve custody, zero-fee recurring buys, and an interest-bearing cash account that pays out in bitcoin. river.com

Quantify Funds: Looking to stack scarcity assets? Quantify Funds is the asset management firm behind the STKd suite of ETFs, including BTGD — the first ETF combining 100% bitcoin and 100% gold exposure. quantifyfunds.com

Most Bitcoin conferences are 30,000 people, vanilla panels, and a badge you never look at again. The Bitcoin Financial Services Summit is the opposite — 200 curated seats, speakers you can actually walk up and talk to, and a room where roughly 80% of the people on stage are founders or executives still building through the bear market.

No guest this week — Wyatt and Jordan take a rare solo pod to break down everything coming to Denver October 20–22, and why this year's summit is bigger and better than year one.

They start with the venue: The Space, a member-run Bitcoin citadel in Denver with miners heating the floors (and the hot tub), and walk through the new Tuesday–Thursday schedule built for Bitcoiners with families — golf scramble and welcome party Tuesday, core summit Wednesday and Thursday, wine and bourbon tastings, and a private-land mountain hike. Long group meals, intentional networking blocks, and zero chance you're scarfing down a burrito while someone herds you back to a talk.

Then the big announcement: continuing education. BFFS and Unchained are bringing real CPE credits for CPAs and financial advisors to the summit — with CLE for attorneys on the roadmap and a self-serve web platform launching later this year. If professionals are forced to grind out credits every December anyway, why not earn them learning about Bitcoin custody, tax, and estate planning — and stop bleeding high-net-worth clients to advisors who scoff at the asset?

They run through the sponsor lineup — Falcon Rappaport & Berkman, Quantify Funds, Sound HSA, River, and Unchained — and the first wave of speakers: Joe Kelly (Unchained), Stephen Cole (Castle), Matt McClintock, Tim Kotzman, Jeff Walton, and Eric Yakes, with a possible moderated Bitcoin treasury debate in the works.

They close with the case for showing up now: the people at a Bitcoin event 40–50% off the highs are the core group. In five years, when the Big Four are offering Bitcoin CPE, you'll wish you'd been in this room.

🎟️ Join Us in Denver, Bitcoin Financial Services Summit The Bitcoin Financial Services Summit returns October 20-22 in Denver, Colorado. RIAs, CPAs, lenders, miners, treasury companies, and Bitcoin-native operators all in one room. If you want to understand where Bitcoin and finance is going next, this is where you need to be. Get your tickets at bffs.media

Chapters

00:00 Introduction

01:06 Welcome to Bitcoin for Financial Services Media

02:03 A Rare Solo Pod: Summit Edition

04:51 The Space: Denver's Bitcoin Citadel Venue

07:52 Golf, Hikes, Tastings, and a Family-Friendly Schedule

11:01 Bitcoin Only — No Crypto, No "Digital Assets"

13:57 Why In-Person Events Matter More Than Ever

17:06 The 2026 Sponsor Lineup

21:44 Sound HSA, River, and Unchained

24:51 The Big One: Bitcoin CPE for CPAs and Advisors

30:15 Inside the Three-Day Schedule

36:50 First Wave of Speakers (and a Possible Treasury Debate)

42:40 Bear Market Conferences: Why You Want to Be in This Room

Host Links

Wyatt O'Rourke

X: x.com/wyattorourke_

Website: basilic.io

Jordan Guess

X: x.com/jordanguess

LinkedIn: linkedin.com/in/jordan-guess-cpa

Website: bitment.co

Bitcoin Financial Services Media

X: x.com/bffs_media

Website: bffs.media

YouTube: @bffs_media

Show Sponsors Basilic Financial: Your wealth deserves intention. Basilic is a Bitcoin-focused wealth management firm helping clients find balance between money and meaning. Financial planning, individual wealth management, retirement services for SMBs, and Bitcoin financial services. 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. Clean Bitcoin bank statements, reliable cost tracking, full reporting, and seamless fiat integration through Plaid. bitment.co

Satoshi Pacioli: Run a Bitcoin business? Meet your full-service accounting and tax partner built for the Bitcoin economy. Bookkeeping, financial reporting, tax compliance, and strategic planning for companies and individuals who speak Bitcoin. satoshipacioli.com