Diary of a CEO
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Top Bitcoin Holder: He Asked AI to Build Something That NEVER Existed, Here's What Happened!

Diary of a CEO · 6 August 2026 · 1h 39m · 7 Egleze moments
Top Bitcoin Holder: He Asked AI to Build Something That NEVER Existed, Here's What Happened! ▶

What happened in this episode?

Michael Saylor, founder of MicroStrategy and a prominent Bitcoin advocate, argues that fiat currency persistently loses purchasing power and frames Bitcoin as “digital capital” that can be held without reliance on banks or states. He contrasts Bitcoin with cash, gold, equities and property, urging people to hold scarce “capital assets” rather than consumables or commodities that can be produced in large quantities.

A central section focuses on his claim that he used ChatGPT to help design a new financing instrument after saying MicroStrategy had “maxed out” conventional equity and convertible bond routes for funding further Bitcoin purchases. Saylor says the company created a Bitcoin-backed convertible preferred stock, STRK, including a mechanism to change the dividend rate monthly. He links this to raising large sums of credit to continue buying Bitcoin, including a claimed $2.5bn IPO for the instrument.

Saylor also addresses MicroStrategy’s leverage and recent sales of Bitcoin. He cites $6.5bn in convertible debt, $15bn in preferred stock and about $58bn in assets, and claims the firm would remain overcollateralised even if Bitcoin fell to $5,000. He says the company sold some Bitcoin to rebut a market narrative that it could not sell without crashing Bitcoin or its own shares.

The conversation ranges into AI-driven automation, arguing that abundant consumer goods may coexist with scarce “trophy” assets, and includes Bartlett’s first-hand description of being shown a Meta wristband concept linked to smart glasses. Saylor predicts Bitcoin will appreciate around 30% annually for two decades before slowing.

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Programme
Diary of a CEO
Published
6 August 2026
Duration
1h 39m
Original episode
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Egleze verifies the speaker, source and timestamp for each linked moment. Unless a moment is explicitly marked independently verified, statements remain attributed claims by the named speaker rather than established facts.

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7 moments from this episode

Source-linked · editorially selected
01
Money

Michael Saylor says ChatGPT helped design a new Bitcoin-backed security

at 34:48 · Attributed speaker claim
So, we used AI to design a a convertible preferred stock called STRK. when we did it, no one had ever created a preferred stock uh that was backed by Bitcoin before and uh and we'd never issued it.

MicroStrategy founder Michael Saylor says he used ChatGPT to help design a new convertible preferred stock, STRK, which he describes as a Bitcoin-backed instrument. He frames it as a novel hybrid between equity and debt after he says the firm had “maxed out” both equity markets and the convertible bond market for raising capital to buy more Bitcoin.

02
Money

Saylor claims AI-assisted STRK issuance enabled $15bn in new credit

at 37:14 · Attributed speaker claim
Because the short of it is we brought that IPO to market. It became a $2.5 billion IPO, the biggest IPO of the year to date.

Saylor claims the STRK preferred stock launch amounted to a $2.5bn IPO, later followed by additional sales via a shelf registration. He links the financing to his earlier claim that using AI-enabled design work helped the firm raise around $15bn to buy more Bitcoin.

03
AI & Tech

Host says Zuckerberg showed him a Meta wristband linked to smart glasses

at 43:35 · Attributed speaker claim
When I met um Mark Zuckerberg, he showed me the the device that's on the way from Meta. This is not a secret because I know they've talked about it publicly, which is just a it was just a plain wrist strap with no screen on it, but it linked to the glasses.

Diary of a CEO host Steven Bartlett says Meta CEO Mark Zuckerberg showed him a prototype-like “wrist strap” device designed to link with glasses, enabling control gestures without a screen. Bartlett describes seeing virtual “screens” in his peripheral vision while using the setup.

04
Money

Michael Saylor says MicroStrategy has $6.5bn convertible debt and $15bn preferred

at 1:23:46 · Attributed speaker claim
I guess we've got about $6.5 billion of convertible debt and $15 billion of preferred stocks outstanding. and we're sitting on top of about $ 58 billion of assets right now.

Michael Saylor says MicroStrategy’s capital structure includes roughly $6.5bn in convertible debt and $15bn in preferred stock outstanding. He also claims the company is “sitting on” about $58bn in assets while pursuing its Bitcoin accumulation strategy.

05
Money

Saylor says Bitcoin could drop to $5,000 and firm stays overcollateralised

at 1:24:34 · Attributed speaker claim
Bitcoin could fall to $5,000 a coin, we would still be over collateralized against the debt.

Asked how far Bitcoin would have to fall before MicroStrategy faced trouble, Saylor says the firm would remain overcollateralised even if Bitcoin traded at $5,000. He frames this as protection against claims that the company’s debt depends on perpetually rising Bitcoin prices.

06
Money

Saylor says he sold some Bitcoin to rebut “can’t sell” market narrative

at 1:26:14 · Attributed speaker claim
we sold some Bitcoin a few weeks ago because there was a narrative or a belief in the market that our company had become so systemically integrated or important to Bitcoin that we could never sell and if we sold, Bitcoin would go to zero and our stock would go to zero.

Saylor says MicroStrategy sold Bitcoin recently to counter a market belief that the firm was unable to sell without collapsing Bitcoin and its own shares. He argues the company needed to demonstrate it could sell without moving the market in order to validate its credit and dividend strategy.

07
Money

Michael Saylor says Bitcoin could rise 30% annually for 20 years

at 1:31:03 · Attributed speaker claim
I think it appreciates about 30% a year for the next 20 years. Right. And then it'll slow down to being appreciative about 20% a year.

Michael Saylor predicts Bitcoin will appreciate by about 30% a year for the next two decades, then slow to roughly 20% annual gains. He argues this makes Bitcoin a superior long-term capital asset and says it could outperform the S&P by 1.5 to two times.