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
