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 Could you please ask him to elaborate how his POV differs from Saylor regarding "Medium of Exchange" vs. "Digital Property"? Also: Jeff does not believe BTC can be/should be financialized (no earning yield from BTC!)...can he explain why not?  
 Because yield brought us in this mess in the first place. 
 Not true. There's ample evidence in history of sound monetary systems (gold/silver-backed) where savers would would invest (purchase debt or equity) in capital projects which would deliver their original principle + yield + on-top profits for the banks & entrepreneurs. The British Pound in late 19th and early 20th century is a prime example: people would purchase the British Gilt which would yield a 6% return. Of course, eventually, the BOE f'd it up and printed "paper" against the pound (literally a pound of silver metal) to pay the yield to the depositors, which ended in catastrophe!
My question remains: is it possible on a BTC standard (21M) to offer a yield against risk? What could that look like? Of course, it will likely never be "6% yield, fully backed!" - but what could it be? What could it look like? Or, are we relegated to the fact that BTC can ONLY be a medium of exchange: no yield, no investments, no capital, just MOE...?  
 I suspect that lightning fees (with people holding self custodial) will be the true risk free rate (see Breez) of the new system. 
Which (as fees rise) in layer 1, will push more people to the interoperability layer of lightning, (and provide through supply and demand) a market for fees that is bounded by free market competition and protocols like Fedimint which would have lower fees.  
But the real crux of your question comes down to the world we live in is one of financialization and many people will try to play that same game and people will fall for it (offering higher fees by not being fully reserved) - which will then blow up (with no one to save them)

Still lots of investments and funding of the free market. Our fund is a perfect example where we believe we can beat a 45% IRR (#Bitcoin rate of return in USD) by investing in entrepreneurs building the new system and as a byproduct…..building their balance sheets in bitcoin. (By offering 10x value to users) 
The choice will always come down to an investor’s belief that they can beat the risk free rate by investing in something that outperforms it. (Against the risk of that investment) 
 Thanks Jeff. Would be interesting to dive deeper into what "investing" would looking like under a BTC standard (BTC as a MOE): How could bonds (issuing debt) be valued based on those holding BTC on layer-2 (would today's cost-of-debt, cost-of-capital, WACC equations apply?)? If there is no debt-issuance, how can debt be created - or should it? Would we forego debt all together and only have equity? In your example: Investing in Ego Death, Fediment, etc.: we're purchasing shares (ok, maybe convertible notes that turn into shares....but go with it..) with no guarantee, promise or backing of a return or yield (the investor owns 100% of the risk) Would we just cancel debt-instruments and only have 1. BTC as MOE & 2. Equity (shares)? Is it even possible (under a BTC-standard) to issue equity without debt? What does that look like? As you say, it's hard to see the system, when you're in the system....in this case, it's difficult to calculate how, exactly, capitalism (debt/equity issuance) will function under a BTC standard - would today's financial mathematics even apply in a future BTC world? 
 Happy to dig deeper at some point but simply - today’s version does not exist, and all of the financial mathematics with it. 
That debt - which most people are pricing from is already insolvent and has been for a long time. Ie - it is only solvent due to the belief that governments will come in and save the day and that saving the day results in a concentration of markets and a perversion of a free market system and then on to a creeping totalitarian and control system. All calculations currently are on top of this.  

Most people also believe that the (insolvent) debt is required for people to make investments which is not true. 

Not a light switch from one system to another but a repricing of everything through bitcoin with many hard lessons for people along the way. 
 Which of these "sound monetary systems" were backed by assets with diminishing to zero inflation?  
 Good point. The great unknown awaits. #bitcoin