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.

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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.

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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 

Seth Hertlein is the Global Head of Policy at Ledger and one of the earliest, most persistent advocates for bitcoin self-custody in Washington. Known for his “lone ranger” years as the only lobbyist focused on protecting non-custodial rights, he brings a rare combination of securities law expertise, political insight, and deep conviction about individual property rights. In this episode, Seth joins The Last Free Americans to share how he fell down the bitcoin rabbit hole, why self-custody is a return to humanity’s oldest property norms, and how today’s policy battles will define digital freedom for generations. We dig into the evolution of financial intermediaries, the history of natural rights from Aristotle to the framers, and the real political forces lining up for and against self-custody.

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TIMESTAMPS:
0:00 – Intro to The Last Free Americans & Seth’s unique role in policy
2:20 – How a securities regulator became an “accidental crypto lobbyist”
5:03 – Early bitcoin reading, monetary policy, and recognizing its political nature
7:43 – The aha moment of self-custody: from Ledger device to first withdrawal
12:58 – Ownership vs. possession: how financial markets drifted into full intermediation
16:40 – Why self-custody is not new: property as a natural human right
22:45 – How centralization overtook markets: certificates, DTCC, and efficiency tradeoffs
27:58 – 2021: the year Washington and the industry “woke up” to each other
33:10 – Keep Your Coins Act, Canadian truckers, and why lawful peer-to-peer matters
38:40 – Property rights, natural law, and the framers’ blind spots on privacy
45:55 – Executive Order 6102, takings law, and lessons for bitcoin
52:03 – How the Bank Secrecy Act and third-party doctrine became digital surveillance
59:42 – The three camps opposing self-custody: nats-ec hawks, socialists, and bureaucracies
1:05:40 – The IRS broker rule, CRA repeal, and precedents for stopping overreach
1:11:22 – House vs. Senate language: what “retain the right” really means
1:17:14 – Odds of passage in 2024 and why Senate floor time is everything
1:22:44 – The global landscape: why America is still the last best hope
1:27:50 – What comes next: privacy as the next digital freedom frontier
1:32:10 – Closing thoughts on restoring founding principles through Bitcoin

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 
 → Seth Hertlein’s Twitter: https://x.com/SethHertlein  

Kent is the CEO of Sazmining and a longtime bitcoiner who previously led large-scale solar operations before building a non-custodial bitcoin mining platform. Recently, he became the victim of a sophisticated in-person scam that resulted in the loss of $220,000 worth of bitcoin.

In this episode, Kent joins The Bitcoin Frontier to share exactly what happened during the scam, what red flags he missed, and why he decided to go public. We dig into the psychology of social engineering, how attackers exploit self-interest, and why even experienced bitcoiners remain vulnerable. We also cover how to build operational security inside a business to mitigate social engineering attacks, how families can prepare for deepfake attacks, and why bitcoin’s immutability still strengthens personal responsibility even in difficult moments.

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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 & Kent’s disclosure of a $220k bitcoin scam
3:20 – Why he chose to go public: PSA, law-enforcement pressure, and justice
7:10 – Kent’s background in solar, bitcoin, and building Sazmining
10:05 – The setup: a “family office” deal, travel, and early yellow flags
14:40 – The first meeting in Amsterdam & unusual trust-building exercises
19:00 – How the attackers built credibility and portrayed ultra-wealth
23:15 – The second meeting, Atomic Wallet, and how the sweep unfolded
28:40 – The psychological trap: self-interest, exhaustion, and urgency
34:00 – Why immutability didn’t shake his conviction in bitcoin
37:25 – Internal policy changes: whitelisting, diligence, and cooling-off periods
41:50 – Distinguishing roles: CEO instincts vs. bitcoiner instincts
45:05 – Scam evolution, social engineering, and the danger of urgency
49:20 – Efforts to recover funds & the limits of both private and public options
54:10 – How AI deepfakes raise the stakes for family safety
57:20 – Why code words, local trust, and multisig can protect loved ones
59:40 – Closing thoughts, personal accountability & Sazmining’s mission

WHERE TO FOLLOW US:
 → Unchained X: https://x.com/unchained 
 → Unchained LinkedIn: https://www.linkedin.com/company/unchainedcom 
 → Unchained Newsletter: https://unchained.com/newsletter
 → Kent Halliburton’s Twitter: https://x.com/khalliburton 
 → Timot Lamarre’s Twitter: https://x.com/TimotLamarre 

Zack Shapiro is the head of legal and policy at the Bitcoin Policy Institute and a key architect behind the Peer-to-Peer Rights Fund. He’s spent years on the frontlines where law, technology, and human freedom intersect—helping lawmakers and judges understand what it means to hold value in the digital age. In this episode, Zack joins The Bitcoin Frontier to break down why self-custody is foundational to bitcoin’s value, how the Clarity Act could define financial freedom for a generation, and why the right to hold your own money might be the most American right of all.

We dig into the constitutional roots of property rights, how U.S. law is being stretched to fit a peer-to-peer world, and why the fight for non-custodial software developers will determine the future of bitcoin in America.

SUPPORT THE PODCAST:
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→ Book a free call with a bitcoin expert: https://unchained.com/consultation?ut...

TIMESTAMPS:
0:00 – Intro & the mission behind The Last Free Americans series
2:00 – What self-custody really means and why it’s the foundation of bitcoin’s value
3:45 – ETFs, financialization, and the fading connection to real bitcoin
5:00 – Why self-custody matters more than ever in 2025
6:15 – How outdated laws are clashing with a peer-to-peer world
7:40 – The Clarity Act and the battle for non-custodial rights
9:00 – Would bitcoin even be valuable without self-custody?
10:00 – How self-custody connects to America’s founding values
12:00 – The Constitution’s protections for holding bitcoin: 1st, 4th, 5th, 9th Amendments
16:00 – The history lesson: Executive Order 6102 and gold confiscation
18:30 – Enumerated powers, the 9th Amendment, and the people’s retained rights
21:00 – Why protecting non-custodial developers is critical to freedom
23:30 – Tornado Cash, Samurai Wallet, and the dangerous new legal precedents
27:30 – Knowledge vs. intent: how the DOJ’s theories stretch the law
31:00 – The risk of calling developers “money transmitters”
33:30 – Steelmanning the other side: why regulators see a loophole
37:00 – How the Bank Secrecy Act evolved from mob busting to digital dragnet
40:30 – From halawa networks to bitcoin: applying old laws to new rails
42:30 – The real ideological divide: state control vs. individual liberty
46:00 – Why self-custody embodies the American idea of limited government
47:30 – If Bitcoin existed in 1776, would the framers have protected self-custody?
49:00 – Strategy going forward: the Clarity Act, education, and vigilance
52:00 – The political battle ahead: Elizabeth Warren, ICOs, and what’s really at stake
54:00 – How bitcoin helps the least powerful—and why that matters most

WHERE TO FOLLOW US:
→ Unchained X: https://x.com/unchained
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Tim Hite is the director of policy at Exodus and a former congressional staffer for Rep. Warren Davidson. He helped shape early self-custody legislation—including the Keep Your Coins Act (a playful nod to “KYC”)—and bridges law, technology, and individual rights. In this episode, Tim’s discussion kicks off The Last Free Americans miniseries to share the origin story of self-custody protections on Capitol Hill, how “keep your coins” language differs from the Clarity Act’s approach, and what meaningful safeguards against CBDCs could look like. We dig into the evolution of property rights in a digital world, why illicit-finance fears are often overstated, and how social media has changed the legislative battlefield.

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 & why self-custody matters now
0:51 – “The Last Free Americans”: series premise
1:16 – Tim’s path: 2017 bull run, law school, FINRA, and meeting Rep. Davidson
3:34 – From Hill staffer to crypto policy: Token Taxonomy Act & early frameworks
6:51 – The spark for the Keep Your Coins Act and naming the bill
11:12 – Two legislative styles: affirming a right vs. restricting regulators
16:24 – Digital ownership as a new chapter in American property rights
19:05 – CBDCs vs. self-custody: opposite ends of the spectrum
22:30 – Social media’s role: sunlight, mobilization, and changing the odds
30:34 – The 2020 “unhosted wallet” rule & why KYCs on self-hosted wallets don’t fit
39:00 – Bank Secrecy Act’s $10k threshold, report overload, and diminishing returns
41:37 – House passage, Senate path, and realistic timelines for the Clarity Act
47:26 – What’s next: tokenized securities and the future of self-custody
52:58 – Peer-to-peer (with an asterisk): whitelists, accounts, and true control
55:01 – Closing thoughts: momentum, vigilance, and “nature finds a way”

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 
 → Tim Hite’s Twitter: https://x.com/TimHite 
 → Jose Burgos (Director of Media Production): https://x.com/DeFBeD

Joe Kelly is the co-founder and CEO of Unchained. In this latest episode, Joe shares his story and Alaskan roots that shaped a deep respect for self-sufficiency—an experience he now applies to the digital frontier. In this episode, Joe joins The Bitcoin Frontier to share why Unchained is launching a new miniseries, The Last Free Americans, how self-custody became his life’s work, and why the conservation movement offers a powerful analogy for protecting financial freedom. We dig into the frontier phases of new assets and ideas, the role of ETFs as a bridge (not the destination), and how policies like developer protections and “keep your coins” language can ring-fence essential rights.

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: The Last Free Americans and what’s at stake with self-custody
1:06 – Alaska, boats, and learning self-sufficiency
2:54 – Conservation mindset: preserving wilderness and preserving peer-to-peer money
4:03 – From accounts to keys: the “aha” of sending bitcoin yourself
5:39 – Seeing the water we swim in: intermediaries, fees, and privacy tradeoffs
8:03 – Frontiers and phases: from prospectors to politics—how new assets mature
10:57 – Gold rush parallels: excess, scams, and integration into the mainstream
12:55 – National parks as a model: ring-fencing what matters for future generations
15:00 – “The last free Americans”: a proud warning about peer-to-peer rights
17:02 – Building Unchained on bitcoin’s assumptions, not fiat rails
19:16 – ETFs as a useful bridge vs. living the peer-to-peer experience
21:03 – Who are today’s “John Muirs”? Gear, guidance, and making self-custody approachable
23:42 – Beyond one bill: culture, developer protections, and keep-your-coins language
26:34 – Free speech, code, and the very American fight for financial privacy
27:34 – Short memories: SVB, protests, and why self-custody matters before the next shock
29:16 – What to expect from the series and the intellectual adventure of bitcoin

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 
 → Timot Lamarre’s Twitter: https://x.com/TimotLamarre 

Pierre Rochard is one of the original bitcoin thinkers, builders, and educators — now serving as CEO of The Bitcoin Bond Company. Known for popularizing the term “speculative attack” in the bitcoin space, Pierre has long explored how bitcoin can replace legacy finance from the inside out.
In this episode, Pierre joins The Bitcoin Frontier to discuss how banks adopting bitcoin could strengthen global stability, how fractional reserve banking might evolve on a bitcoin standard, and why he believes governments buying bitcoin is inevitable. We dig into the rise of bitcoin treasury companies, the idea behind bitcoin bonds, and whether bitcoin’s decentralization can withstand institutional adoption.

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 & bitcoin’s ideological roots in libertarianism
3:00 – Why banks holding bitcoin could prevent future financial crises
7:20 – Can fractional reserve banking exist on a bitcoin standard?
10:50 – MicroStrategy and the rise of bitcoin treasury companies
12:40 – Why collapsing banks would be dangerous for society
16:00 – Financial intermediation, savings culture, and a soft landing to a bitcoin economy
18:00 – “Money for enemies”: Why state adoption isn’t betrayal
20:00 – Bitcoin in U.S. and state reserves: From Texas to Trump
23:00 – Can governments or corporations co-opt bitcoin?
25:00 – What bitcoin bonds are and how the Bitcoin Bond Company works
29:30 – Bringing bitcoin into institutional portfolios through structured credit
35:00 – Comparing bitcoin bonds to MicroStrategy’s convertibles
37:00 – Why treasury companies are undervalued and what investors are missing
40:00 – Hyperbitcoinization, speculative attacks, and soft landings
45:00 – How adoption is accelerating asymmetrically across nations
50:00 – The ETF era: Collaborative custody and the path from convenience to sovereignty
55:00 – Have we peaked in self-custody? UX, education, and generational change
58:00 – Is bitcoin’s freedom money inevitable — and what are the real threats ahead?
1:02:00 – Quantum computing, Satoshi’s coins, and the future of protocol resilience
1:03:00 – Where to find Pierre online and closing thoughts

WHERE TO FOLLOW US:
 → Unchained X: https://x.com/unchained 
 → Unchained LinkedIn: https://www.linkedin.com/company/unchainedcom 
 → Unchained Newsletter: https://unchained.com/newsletter
 → Pierre Rochard’s Twitter: https://x.com/BitcoinPierre 
 → Timot Lamarre’s Twitter: https://x.com/TimotLamarre 

Marty Bent is a bitcoin investor, media founder, and host of TFTC — one of the longest-running bitcoin podcasts. He’s also a managing partner at Ten31, supporting companies building critical bitcoin infrastructure. Marty is uniquely positioned at the intersection of bitcoin, energy, and now artificial intelligence.
In this episode, Marty joins The Bitcoin Frontier to share how AI is transforming the bitcoin ecosystem, how his team at TFTC is leveraging it to streamline media production, and how it’s fueling his latest creative projects. We dig into how he built Opportunity Cost, why AI drives decentralization in mining, and how bitcoiners can use these tools to stay ahead of the curve.

SUPPORT THE PODCAST:
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→ 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 & why bitcoin and AI are converging faster than anyone expected
2:00 – Marty’s projects: TFTC, Ten31, and bitcoin mining
5:00 – The evolution of TFTC and what the rebrand to “Truth for the Commoner” means
8:30 – How the team integrates AI tools across research, writing, and production
12:00 – From Perplexity to Claude: learning to use AI as a research assistant
15:00 – Automating TFTC’s backend workflows with AI and no-code tools
18:00 – Clipping, editing, and distribution: using AI for speed and quality
23:00 – Building Opportunity Cost: turning fiat prices into sats in your browser
27:00 – Why open-source and privacy-preserving design still matter
30:00 – The birth of AI-generated storytelling
33:00 – Storyboarding, JSON prompts, and producing viral AI bitcoin videos
38:00 – The Trojan horse approach: spreading bitcoin ideas through culture
46:00 – Bitcoin and AI’s overlap: how energy demand is driving decentralization
50:00 – Paying for compute with bitcoin and why eCash may win
55:00 – AI, energy, and the physical limits of growth
58:00 – How bitcoin founders are using AI to build faster and cheaper
1:00:00 – Practical advice: using AI without compromising your craft or security
1:01:30 – Where to follow Marty and watch his latest creations

WHERE TO FOLLOW US:
→ Unchained X: https://x.com/unchained
→ Unchained LinkedIn: / unchainedcom 
→ Unchained Newsletter: https://unchained.com/newsletter
→ Marty Bent’s Twitter: https://x.com/MartyBent
→ Trey Seller’s Twitter: https://x.com/ts_hodl 

James Check (aka Checkmate) is the co-founder of Checkonchain and one of the leading voices making onchain data accessible for everyday bitcoiners. Known for his ability to turn complex charts into compelling stories, James blends his engineering background with market analysis to help people see human behavior imprinted in bitcoin’s ledger. In this episode, James joins The Bitcoin Frontier to share why realized cap is one of the most powerful adoption metrics, how to interpret profit and loss across holders, and what onchain data is saying about the current cycle. We dig into the role of ETFs and treasury companies, the impact of derivatives on market structure, and why the future of onchain analytics remains deeply human.

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→ 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 & why onchain data matters for bitcoin
1:30 – Buying the 2017 top, engineering background & finding bitcoin
4:50 – Realized cap, cost basis, and why it just crossed $1T
7:30 – From civil engineering to onchain analysis
10:00 – Orange pill moments, macro influences, and early metrics
12:40 – Human behavior, fear & greed mapped onchain
15:00 – Turning raw data into stories people understand
18:00 – State of the market in 2025: leverage, ETFs, and demand
22:00 – Cycles, late-stage dynamics & institutional flows
26:00 – Rethinking market cycles: the three-cycle structure
31:00 – Sell-side pressure, hodlers, and ETF dynamics
35:00 – Are ETFs and treasury companies changing onchain analysis?
40:00 – Profit, loss, and building decision frameworks for different price scenarios
46:00 – Key support zones: 110K, 90K, and Sailor’s liquidation line
49:00 – Derivatives, ETFs, and how flows shape volatility
54:00 – Risks of leverage, banks entering, and future fireworks
58:00 – Rapid fire: desert island metrics, entry point for retail, and data wish list
1:02:00 – The Australian bitcoin community & grassroots conferences
1:05:30 – The future of onchain analytics, AI, and Checkonchain’s next report

WHERE TO FOLLOW US:
→ Unchained X: https://x.com/unchained
→ Unchained LinkedIn:   / unchainedcom 
→ Unchained Newsletter: https://unchained.com/newsletter
→ James Check’s Twitter: https://x.com/_Checkmatey_
→ Connor Dolan’s Twitter: