Investing · Brent Sullivan

The Albatross

by Brent Sullivan

The Albatross is about managing concentrated wealth. Each week, I interview an expert, and we discuss the risks of holding public and private single-asset positions and the numerous ways of exiting thoughtfully. This includes tax-loss harvesting, hedging with options and variable prepaid forwards, exchange funds, qualified opportunity funds, numerous charitable strategies, estate planning vehicles, and several other solutions for private stock and other assets.

Latest episodes

Showing 5 · updated from the feed

Covered Calls Are Not For Hedging With Roy Haya

Covered calls are in the single-stock management canon, but not because they meaningfully hedge risk. Roy Haya, Partner and Head of Derivative Solutions at Fort Point Ca

Sep 18
29 min

The Cost of Holding a Concentrated Position with Antti Petajisto

Antti Petajisto and I talk about concentration drag resulting from the many, many, many public companies that go bust, and the tiny slice of the market that vastly outper

Sep 14
22 min

Opportunity Zones Won't Save a Bad Deal, But Can Accelerate a Good One

The biggest criticism of Qualified Opportunity Funds is that the tax tail is wagging the dog so hard that investors completely lose sight of investment viability. Nick R

Sep 3
26 min

Investing in Three Dimensions with Paul Bouchey

Paul Bouchey is the Editor of the Journal of Wealth Management, Managing Director of Applied Research at Morgan Stanley, and the former Chief Investment Officer at Parame

Aug 28
33 min

A Good Problem

The Albatross is about navigating concentrated wealth. Markets are at all-time highs, and founders, executives, early employees, and investors have become rich... but hi

Aug 14
1 min