Jun 25, 2026 · 32 min · 14 segments
In this episode of Deep Dive Podcast, host Rachel Wolfson sits down with Jason Leibowitz, head of business development at Meanwhile, to discuss Bitcoin life insurance. Jason explains how Meanwhile…
Jason LebowitzGuest
Rachel WolfsonHost
Bitcoin has matured a lot from when you entered, right? What are your thoughts on that maturity? And do you think that that's a good thing? Do you think we're going to continue to see the sector mature moving forward?


You have the micro strategies of the world, which are amassing the most massive piles of Bitcoin and other digital asset treasury companies, other companies and people just allocating to Bitcoin because they recognize that it is a non-sovereign uncorrelated asset that has nothing to do with inflation and fiat currency devaluation.

And so, you know, you see all this investment advice, whether it comes from global macro fund managers or banks or other asset managers or financial advisors saying you should have two or five or eight or 10% of your portfolio in Bitcoin, among other assets, equities, fixed income, real estate, etc., because it gives you this diversity and it gives you this, we call Bitcoin a highly convex asset because it has this asymmetric upside potential.

And so it's always good to have an asset that has this long tail potential in your portfolio.

They don't understand how this thing that we don't know who invented it has any value and it's not backed by anything.

But when you really look at anything in the world that has a price to it, it's only worth what someone's willing to pay for it.

Whether that's gold, whether that's your house on an island, or your apartment on the 80th floor of a skyscraper.

if you look at gold intrinsic value, you can't eat it in the worst of times.

And I believe that Everything that happened leading up to the moment of the internet was its own era.

And now that we're in this internet networked age with the power of network connectivity, everything is different.


And to them, as they get older, what's going to have more value? Something digital or something physical and heavy metal like a rock? And to me, it's obvious that everything is going to be digital.

And so would you rather invest in the future of digital gold or antiquated pre-internet physical gold? And I think that this is like a common example of digital gold, Bitcoin digital gold, but I see it.

I see it every day that the digital age is here and is only going to get bigger and more important.

Bitcoin has matured a lot from when you entered, right? What are your thoughts on that maturity? And do you think that that's a good thing? Do you think we're going to continue to see the sector mature moving forward?


You have the micro strategies of the world, which are amassing the most massive piles of Bitcoin and other digital asset treasury companies, other companies and people just allocating to Bitcoin because they recognize that it is a non-sovereign uncorrelated asset that has nothing to do with inflation and fiat currency devaluation.

And so, you know, you see all this investment advice, whether it comes from global macro fund managers or banks or other asset managers or financial advisors saying you should have two or five or eight or 10% of your portfolio in Bitcoin, among other assets, equities, fixed income, real estate, etc., because it gives you this diversity and it gives you this, we call Bitcoin a highly convex asset because it has this asymmetric upside potential.

And so it's always good to have an asset that has this long tail potential in your portfolio.

They don't understand how this thing that we don't know who invented it has any value and it's not backed by anything.

But when you really look at anything in the world that has a price to it, it's only worth what someone's willing to pay for it.

Whether that's gold, whether that's your house on an island, or your apartment on the 80th floor of a skyscraper.

if you look at gold intrinsic value, you can't eat it in the worst of times.

And I believe that Everything that happened leading up to the moment of the internet was its own era.

And now that we're in this internet networked age with the power of network connectivity, everything is different.


And to them, as they get older, what's going to have more value? Something digital or something physical and heavy metal like a rock? And to me, it's obvious that everything is going to be digital.

And so would you rather invest in the future of digital gold or antiquated pre-internet physical gold? And I think that this is like a common example of digital gold, Bitcoin digital gold, but I see it.

I see it every day that the digital age is here and is only going to get bigger and more important.
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