The Bitcoin Frontier

Denny is a wealth manager and bitcoin research lead at Morgan Stanley, where he bridges traditional finance and bitcoin for high-net-worth investors. He operates inside one of the world’s largest financial institutions while developing frameworks to help advisors understand and allocate to bitcoin.
In this episode, Denny joins The Bitcoin Frontier to share how investors should think about bitcoin in a portfolio, the three core investor buckets driving adoption, and his thoughts on determining whether you’re underweight or overweight bitcoin. We dig into bitcoin’s market cycles and seasonal framework, the role of global money supply in driving returns, and practical strategies for gaining exposure in a volatile asset.
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TIMESTAMPS:
0:00 – Intro & Denny’s role bridging traditional finance and bitcoin
2:00 – From equity research to leading bitcoin insights at Morgan Stanley
4:20 – The three investor buckets: digital gold, venture, and diversifier
7:30 – How institutions evaluate volatility and correlation
10:50 – Where bitcoin fits in portfolios today (risk asset vs store of value)
14:00 – How to determine if you’re underweight or overweight bitcoin
18:00 – Why most investors are still early (0–4% allocation range)
21:40 – Will the three investor frameworks converge over time?
23:10 – Bitcoin cycles: macro liquidity vs halving-driven supply shocks
26:30 – Using cycles for rebalancing vs long-term holding strategies
31:20 – Tail risks: quantum computing and “earthquake” scenarios
36:10 – Bitcoin as a global store of value and M2-driven returns
41:10 – Modeling long-term returns: monetary expansion + adoption
48:30 – How to build a position: dollar-cost averaging and timing
52:15 – Seasons of bitcoin: winter, spring, and portfolio adjustments
55:00 – What it takes for bitcoin to become a standard portfolio allocation
WHERE TO FOLLOW US:
→ Unchained X: https://x.com/unchained
→ Unchained LinkedIn:   / unchainedcom 
→ Unchained Newsletter: https://unchained.com/newsletter
→ Denny Galindo’s Twitter: https://x.com/DennyGalindo 
→ Timot Lamarre’s Twitter: https://x.com/TimotLamarre

Allen Farrington is an investor at Axiom BTC Capital and a writer known for sharp, contrarian takes on bitcoin and adjacent topics like bitcoin venture capital, fiat “plumbing,” and stablecoins. With Axiom, Allen uniquely focuses on clients’ returns not coming from financial engineering, but from productive deployment of capital to solve real world problems.
In this episode, Allen joins The Bitcoin Frontier to share how bitcoin exposes the fiat distortions inside venture capital, why clear lines between saving and investing change founder and limited partner (LP) behavior, and what a bitcoin-first stack means for payments and stablecoins. We dig into local capital allocation on a sound-money standard, free/open-source dynamics and moats, and why lightning + ecash may be the endgame for stablecoins.

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TIMESTAMPS:
0:00 – Intro & disclaimer; setting up VC in a world of finite money
2:12 – Bitcoin as “fixing the plumbing”: unwinding fiat distortions vs fantasizing about the end state
4:45 – How artificially low rates monetize other assets and push allocators out the risk curve
7:28 – Pension funds, liabilities, and why flows into venture decouple from fundamentals
9:46 – “Thousand-x or bust”: why LP incentives shape VC behavior (and fund crypto)
12:02 – Saving vs investing: why buying bitcoin ≠ venture investing (and Axiom’s thesis)
16:05 – Local investing on a sound-money standard and higher opportunity costs for founders
20:52 – Measuring in bitcoin terms: hurdle rates, returns, and what “outperforming bitcoin” really means
27:15 – Trusted third parties are security holes… so where do businesses add value? (non-custodial services)
32:06 – Moats in a FOSS world: compete by delivering value, not lock-in
36:50 – “Zero to One,” monopolies, and why ruthless excellence beats user exploitation
41:10 – Open vs closed source: the healthy tension in bitcoin-native companies
44:22 – Allen’s “half-baked” stablecoin thesis: why new “stablecoin blockchains” are a dead end
47:06 – The Genius Act: fully reserved dollars, surveillance tradeoffs, and limited real-world impact so far
48:55 – Lightning as settlement layer for fiat tokens; taproot assets / RGB today, ecash tomorrow
55:00 – Could fully reserved rails hollow out small banks? Centralization pressures and unintended consequences
56:44 – Closing: where to find Allen and Axiom BTC
WHERE TO FOLLOW US:
→ Unchained X: https://x.com/unchained
→ Unchained LinkedIn: https://www.linkedin.com/company/unchainedcom  
→ Unchained Newsletter: https://unchained.com/newsletter
→ Allen Farrington’s Twitter: https://x.com/allenf32   
→ Timot Lamarre’s Twitter: https://x.com/TimotLamarre
→ Jose Burgos (Director of Media Production): https://x.com/DeFBeD

Anna Chekhovich is a Russian activist who manages the Anti-Corruption Foundation’s finances while living in exile. She runs payrolls, budgeting, and fundraising for a movement that faces surveillance, asset seizures, and sanctions. What sets Anna apart is her operational playbook for keeping an organization alive when banks fail you. In this episode, Anna joins The Last Free Americans to share how bitcoin became ACF’s plan B for payroll and donations, how activists build practical off-ramps under hostile regimes, and how she co-designed a simple three-day training that now serves activists from more than 50 countries. 
SUPPORT THE PODCAST:
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 → Book a free call with a bitcoin expert: https://unchained.com/consultation?utm_source=youtube&utm_medium=social&utm_campaign=podcast
TIMESTAMPS:
0:00 - Intro, disclaimers, and why Bitcoin self-custody matters for human rights
1:04 - Running ACF finances under surveillance and in exile
3:23 - Bank freezes and the shift to bitcoin as plan B
4:52 - Paying 300 plus staff when accounts are seized
5:57 - Donor safety in authoritarian regimes and why self-custody is essential
7:10 - Explaining self-custody in the U.S. context
9:37 - The HRF webinar design and why simplicity wins
12:09 - Day 1 playbook: custody types, first wallet, sending sats
12:41 - Day 2 playbook: last mile options, P2P, meetups, and ATMs
13:52 - Day 3 playbook: self-hosted crowdfunding with BTCPay Server and cold storage
16:22 - Why lightning for live demos and choosing simple wallets like Muun
20:57 - Sanctions and supporting family via P2P off-ramps
31:19 - Multisig for nonprofits and where Unchained fits
35:02 - Privacy by default with coinjoin and better ops hygiene
39:14 - The peace time case for self-custody and financial dignity
WHERE TO FOLLOW US:
 → Unchained X: https://x.com/unchained 
 → Unchained LinkedIn: https://www.linkedin.com/company/unchainedcom 
 → Unchained Newsletter: https://unchained.com/newsletter
 → Joe Kelly’s Twitter: https://x.com/josephkelly 
 → Anna Chekhovich’s Twitter: https://x.com/AnyaChekhovich

Mark Connors is a veteran credit analyst and macro thinker who’s spent nearly four decades on Wall Street, from the bond desks of Solomon Brothers to the hedge fund trenches. What makes Mark unique is his ability to pull the lens back—connecting regime changes in global finance to bitcoin’s rise as the asset with true integrity.
In this episode, Mark joins The Bitcoin Frontier to share how his career shaped his understanding of risk, why bitcoin is the next monetary regime shift, and how Wall Street is still missing the plot. We dig into why bitcoin’s volatility is actually a superpower, how financial plumbing is breaking beneath the surface, and why institutions will eventually be forced to adopt bitcoin as pristine collateral.

SUPPORT THE PODCAST:
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 → Send us an email: [email protected]
 → Learn more about Unchained: https://unchained.com/?utm_source=you...
→ Book a free call with a bitcoin expert: https://unchained.com/consultation?ut...
TIMESTAMPS:
0:00 – Intro & Mark’s 40-year Wall Street journey through credit and crisis
3:15 – Lessons from Solomon Brothers to Bitcoin Park: where integrity lives
6:05 – How bitcoin fits into the third monetary regime since Bretton Woods
8:00 – The “hacks” that brought bitcoin into Wall Street’s line of sight
10:00 – Bitcoin as collateral and the coming collateral crisis
12:20 – Understanding volatility: why bitcoin’s risk is asymmetric
17:00 – The myth of volatility and the truth about upside variance
21:00 – “Good vol” vs “bad vol”: how bitcoin surprises to the upside
25:00 – Why rebalancing into bitcoin beats traditional 60/40 portfolios
29:00 – Can Wall Street co-opt bitcoin through paper markets?
31:00 – The importance of holding your own keys and verifying collateral
35:00 – Convincing older investors and rebuilding credibility post-FTX
37:00 – Regime changes, Bretton Woods, and how history rhymes
43:00 – How the dollar was “saved” by energy and the petrodollar system
46:00 – Hidden cracks in the financial system and repo stress explained
49:00 – How new liquidity facilities show a fragile, patched-up system
52:00 – Will Wall Street adopt bitcoin for safety or profit?
55:00 – The slow cultural shift toward integrity in finance
57:00 – The ultimate incentive: clients demanding bitcoin exposure
1:00:00 – Risks to bitcoin: mining centralization, paper supply, and innovation
1:02:00 – Where to follow Mark and how he’s educating advisors
WHERE TO FOLLOW US:
→ Unchained X: https://x.com/unchained
→ Unchained LinkedIn:   / unchainedcom 
→ Unchained Newsletter: https://unchained.com/newsletter
→ Mark Connors’s Twitter: https://x.com/riskdimensions 
→ Timot Lamarre’s Twitter: https://x.com/TimotLamarre

Peter Van Valkenburgh is the Executive Director of Coin Center, a leading nonprofit research and advocacy group focused on cryptocurrency policy. In this episode, Peter joins The Bitcoin Frontier to explore why defending the right to self-custody is about much more than bitcoin — it’s about the future of individual freedom, open-source innovation, and financial privacy. We dig into the parallels between the 1990s “crypto wars” and today’s digital sovereignty battles, the threats facing developers of privacy tools, and the constitutional foundations for privacy and property in the digital age.
SUPPORT THE PODCAST:
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 → Leave a review
 → Share the show with your friends and family
 → Send us an email: [email protected]
 → Learn more about Unchained: https://unchained.com/?utm_source=you...
→ Book a free call with a bitcoin expert: https://unchained.com/consultation?ut...

TIMESTAMPS:
0:00 – Intro and Peter’s journey from acting to bitcoin policy
2:00 – Discovering the cypherpunks and the roots of internet freedom
4:00 – Entering bitcoin through law school and meeting Jerry Brito
6:00 – Founding Coin Center and defining “permissionless innovation”
9:00 – The mission: protecting the freedom to build and use open blockchains
11:00 – Bitcoin’s privacy problem and the legal risks of building privacy tech
13:00 – Educating DC: explaining bitcoin to Congress in the early days
16:00 – Navigating the SEC, ICOs, and defining what counts as a security
18:30 – The evolution from education to constitutional litigation
22:00 – Bitcoin as the revival of a “bearer instrument” economy
26:00 – The “secret right to cash” and the Fourth Amendment’s blind spot
30:00 – Privacy, property, and what bitcoin reveals about constitutional limits
35:00 – The Keep Your Coins Act and why it matters for financial sovereignty
43:00 – The DOJ’s shift toward prosecuting developers — and why it’s dangerous
46:00 – Inside the Tornado Cash and Samurai Wallet prosecutions
50:00 – How Coin Center is fighting for software publishing rights
54:00 – Legislative progress: Clarity, Keep Your Coins, and BRCA
1:00:00 – Lessons from the 1990s encryption wars
1:03:00 – How liability protections shaped (and centralized) the internet
1:08:00 – The convenience dilemma: why self-custody must become easier
1:12:00 – The Bank Secrecy Act, mass surveillance, and new legal challenges
1:19:00 – Coin Center’s constitutional lawsuits for privacy and association rights
1:23:00 – Why the BSA is ripe for reform — and bitcoin’s role in that debate
1:27:00 – Zero-knowledge proofs, AML, and a future of privacy-preserving compliance
1:29:00 – How self-custody wallets enable digital identity and personal sovereignty
1:31:00 – Closing thoughts: bitcoin as the foundation for a freer digital future
WHERE TO FOLLOW US:
→ Unchained X: https://x.com/unchained
→ Unchained LinkedIn:   / unchainedcom 
→ Unchained Newsletter: https://unchained.com/newsletter
→ Joe Kelly’s Twitter: https://x.com/josephkelly
→ Peter Van Valkenburgh’s Twitter: https://x.com/valkenburgh