Proof of Pain

In this episode of Proof of Pain, Tony sits down with Nik Lentz, former UFC veteran and quantitative analyst, to talk about Bitcoin, MSTR, STRC, and the risks around digital credit. We also get into Nik’s path from MMA to finance, how he learned to think like a quant, and why he has become skeptical of Wall Street’s version of Bitcoin. Nik is not anti-Bitcoin. He makes the case that Bitcoin wrappe...

In this episode of Proof of Pain, Tony sits down with Nithu Sezni of True North and the Orange Pill Investor to talk about digital credit, STRC, SATA, and the current BIP-110 fight. We break down who these products are actually for, why Strategy and Strive matter, and whether Bitcoiners are right to dismiss treasury companies and just buy BTC. We also cover Bitcoin as collateral, SATA risk vs STRC...

In this episode of Proof of Pain, Tony sits down with Jim Crider, certified financial planner and founder of Intentional Living FP. They talk about what money is, why so many people in finance still misunderstand Bitcoin, and how Jim thinks about portfolio construction in a world shaped by inflation, money printing, AI, and rising uncertainty. They also cover Jim’s path into financial planning, ho...

In this episode of Proof of Pain, Tony sits down with Richard Byworth, Chairman at Future Holdings and an active participant in the H100 expansion into Switzerland. We talk about Bitcoin treasury companies, MSTR’s capital markets evolution, preferreds vs convertible bonds, and whether “paper Bitcoin” is a real concern. We also cover why Bitcoin denominated convertible bonds matter for smaller trea...

In this solo episode of Proof of Pain, Tony covers two Bitcoin headlines driving the week, then pulls up the chart to check the levels he is watching. Tony talks about the Jane Street “10AM slam” chatter and why ETF mechanics can create weird looking moves around the market open. Then a quick look at spot Bitcoin ETF dip buying and what it might signal when price is chopping in a tight range. To f...

In this episode of Proof of Pain, Tony sits down with UFC bantamweight Aiemann Zahabi to talk about Bitcoin in plain English. We break down why Bitcoin feels like money on your phone, how you can send it to anyone anywhere without permission, and why self custody matters. No maintenance fees. No transfer approvals. Full control of your money. Watch the full video episode on YouTube: https://youtub...

In this episode of Proof of Pain, Tony sits down with James (@ourgoodlifeuk), a UK podcaster and Bitcoin adoption advocate. He shares his path from early mining days, to ignoring Bitcoin for years, to going deep in 2024 and then diving into Bitcoin treasury companies, especially Smarter Web (SWC). We talk SWC from IPO vibes to drawdowns, the Bitcoin treasury flywheel under stress, what James would...

In this episode of Proof of Pain, Tony sits down with Bob Burnett (Barefoot Mining, board member at Ocean, ex Gateway CTO) to break down off grid Bitcoin mining, cost of production, and why public miners often get valued like tech stocks even though mining is a commodity business. We also dive into Core vs Knots, block templates, spam and inscriptions, OP_RETURN, the SegWit discount, and why Bob i...

In this episode of Proof of Pain, Tony sits down with Mike Flaum (Grain of Salt) to break down Bitcoin investing through a product manager lens: optionality, taxes, IRAs, and why “shares per Bitcoin” can be the clearest way to understand Bitcoin treasury companies like Strategy (MSTR). We also go deep on AI research workflows, how to battle models, and why preferreds changed the treasury playbook....

In this episode of Proof of Pain, Tony sits down with Nithu Sezni (founding member MSTR True North) to talk Bitcoin, options, leverage, and Bitcoin Treasury Companies. We get into Poor Man’s Covered Call mistakes, Tesla drawdowns, MSTR’s long game, and the controversial “0% credit cards to buy Bitcoin” strategy. We also debate Core vs Knots, spam, node incentives, and the real costs of custody. Wh...

In this episode of Proof of Pain, Tony sits down with Alexandre Laizet, Director of Bitcoin Strategy at Capital B, a Bitcoin treasury company building in Europe. We talk about maximizing Bitcoin per share, why Alexandre believes you do not sell Bitcoin, and how the treasury flywheel evolves across market regimes, including equity, converts, and preferred style structures. We also get into mNAV pre...

In this episode of Proof of Pain, Tony sits down with Pierre Rochard for a deep Bitcoin conversation that connects economics, investing, and Bitcoin’s design. We cover Bitcoin Treasury Companies and why the market is starting to group them into Digital Asset Treasury Companies (DATs), why Strategy (MicroStrategy, MSTR) behaves differently than spot Bitcoin, and the Core vs Knots debate around OP_R...