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Updated 2026-10-28 12:00 UTCnext update 2026-10-29 00:00 UTC
Confirmed · 3 sources703 words

Three Operators on Building Things That Last

In podcast episodes published October 27 and 28, Mark Cuban argues health care needs price discovery, Bill Ackman explains a decade without an activist campaign, and Flexjet chairman Kenn Ricci describes growing an aviation business by staying narrow and deep.

Key facts
  • On the a16z podcast, Mark Cuban argued the health care system lacks competitive dynamics because it lacks price discovery, and said his company Cost Plus Drugs grew from 111 medications at launch to about 4,000 SKUs. m:…5986
  • On the In Good Company podcast, Bill Ackman said Pershing Square has not launched an activist investment in 10 years and runs a concentrated portfolio of 12 to 14 investments. m:…4379
  • On the Founders podcast, Flexjet chairman Kenn Ricci said he bought his first aviation company for 27,500 dollars using the company own cash reserves, and described a strategy of staying narrow and deep in aviation alone. m:…7430

Cuban: make prices visible, then let competition work

Mark Cuban told the a16z podcast that the health care industry lacks competitive dynamics because it lacks price discovery, and his prescription starts with transparency rather than with new technology. Cost Plus Drugs, the company he founded, grew from 111 medications at launch to approximately 4,000 SKUs, and it pays independent pharmacies a 12 dollar fill fee, a design choice aimed at keeping local pharmacy infrastructure viable while prices stay public. m:…5986

Cuban also argued that employers can significantly reduce health care costs by running benefits contracts through AI tools to identify unfavorable terms, and he claimed that if 67 percent of employers audited their contracts that way, the current vertically integrated insurance and pharmacy benefit system would collapse. That is an argument about bargaining power, not a forecast to take literally: the point is that opaque contracts survive because nobody reads them at scale. m:…5986

His policy proposal follows the same logic. Cuban said a solution involves mandating public disclosure of all contracts involving taxpayer money, and he cited the scale of the opacity he is describing: UnitedHealth manages over 3,000 subsidiaries and conducts 150 billion dollars in annual intercompany transfers, according to Cuban. He also described modular manufacturing pods costing approximately 20 million dollars each that can be configured to produce specific drugs, and noted the 365,000 dollar cost of applying for an abbreviated new drug application plus additional fees. m:…5986

Ackman: concentration, patience, and permanent capital

Bill Ackman told the In Good Company podcast that Pershing Square has not launched an activist investment in 10 years, a notable shift for a firm once defined by campaigns. The firm now runs a single portfolio of 12 to 14 investments, with Amazon, Meta, and Microsoft representing about one-third of it, and its investment team is compensated on overall portfolio performance rather than individual profit and loss. m:…4379

Ackman described the next step as transforming Pershing Square toward a Berkshire Hathaway-style permanent capital vehicle, in part by turning Howard Hughes into an asset-light real estate company whose capital can be reinvested into insurance operations. The insurance team behind that plan includes Mark Grandison and David Gansberg, according to the conversation. The through line is durability: capital that does not need to be returned on a fund cycle can afford to wait. m:…4379

On process, Ackman said the best way to gain conviction in an investment is to rebut the arguments of the best short-seller in that stock, a discipline that forces a thesis to survive its strongest critic before capital follows. He also argued that AI is making market participants increasingly short-term by enabling instant analysis of filings, which makes his long-horizon posture a deliberate bet against the direction of the market around him. m:…4379

Ricci: narrow, deep, and on the balance sheet

Kenn Ricci, chairman of Flexjet, told the Founders podcast that he purchased his first aviation company, Corporate Wings, for 27,500 dollars using the company own cash reserves, and grew from there to a fleet including 85 Gulfstreams, making Flexjet the largest operator of that aircraft type in the world. The global private jet fleet grew from 5,000 aircraft in 1985 to 35,000 today, according to Ricci, so his growth rode a large market expansion as well as his own execution. m:…7430

His stated strategy is to remain narrow and deep by investing exclusively in aviation, and he argued that mergers and acquisitions are often a sign of weakness that can cause significant cultural damage to a business. In capital-intensive industries like aviation, Ricci argued, the balance sheet matters more than the income statement, because aircraft and infrastructure commitments outlive any single year of earnings. m:…7430

Two operating details round out the picture. Flexjet empowers frontline employees to resolve customer service issues, including compensating trips, without supervisor approval, pushing decisions to the people facing the customer. And Ricci advocated transferring wealth to children while alive in order to provide mentorship, rather than using trusts to control them from the grave, a personal coda consistent with his business theme: control less from above, and build the people below you. m:…7430

The three conversations share a discipline worth naming. Cuban wants prices visible so competition can function, Ackman wants capital patient so concentration can compound, and Ricci wants scope narrow so operations can deepen. Different industries, same instinct: remove the structural excuse, then do the work. m:…5986

What is still unresolved

  • Whether employer contract auditing at scale actually moves health care prices, or only shifts bargaining between intermediaries.
  • Whether Pershing Square permanent capital structure delivers the stability Ackman describes across a market downturn.
  • Whether Flexjet narrow aviation focus holds as the private aviation market matures or consolidates.

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Cited Manifest ids (3)
  • 1793185200235665986
  • 1793162815943244379
  • 1793180984197337430
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Provenance ledger

ManifestTitleSourceClaims usedPublished
1793185200235665986Mark Cuban's Plan to Make Healthcare Affordableandreessen-horowitz-a16z-show-podcast1793185396284219799, 1793185396278302983, 1793185396286648753, 1793185396283373034, 1793185396291909687, 1793185396297856209, 1793185396281053364, 1793185396289450989, 179318539629538951310-28 00:00
1793162815943244379Bill Ackman: Concentrated Investing, Permanent Capital, and the Value of Being Challengedin-good-company-podcast1793163457743944189, 1793163457747625776, 1793163457755912338, 1793163457769714883, 1793163457759645744, 1793163457763667796, 1793163457768763160, 179316345774957398110-28 00:00
1793180984197337430From a $27,500 Charter Company to a $4 Billion Private Jet Giant | Kenn Ricci, Flexjetdavid-senra1793181671463242150, 1793181671451760502, 1793181671461048521, 1793181671454371735, 1793181671456308069, 1793181671460698138, 1793181671453251410, 179318167144702149810-28 00:00

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