The Albatross artwork

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 10 · updated from the feed

Landing the long/short plane with BlackRock's Taotao Cai

For tax-aware long/short strategies, some see the leverage as cost-effective, amplified exposure to the underlying manager, while others need to have a plan to land the p

Oct 9
20 min

IRS on "solid ground" going after suspicious §351 transactions - Bob Elwood and Ray Holst

Last week, Treasury released Notice 2026-62 and Rev. Rul. 2026-20 concerning IRC §351 transactions, nowadays popularly used to seed new exchange-traded funds (ETFs) in-ki

Oct 5
32 min

Too much tax alpha, too little diligence with Steve Curley

There's a flavor of financial adviser that understands how powerful tax alpha sounds to prospects and clients, but who hasn't thought too much about what could go wrong.

Oct 1
18 min

Abusive §351 is dead, long live routine §351

For the last few years, the ETF industry has used Section 351 of the Internal Revenue Code to let investors seed new exchange traded funds with appreciated securities, mo

Sep 30
10 min

Exchange Fund Replication using Options with BlackRock's Eric Metz

Exchange fund replication is a hidden gem in the concentrated public stock de-risking toolkit. Exchange fund replication is a 4-legged options trade that collars a singl

Sep 25
22 min

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

Chart trend

Position in the Investing chart (US), last 90 days.

#84
all-time peak
5
days in the top 100 since Aug 2026

Chart positions

Where The Albatross ranks today in each Apple Podcasts chart (US, Oct 13, 2026).

#135 ▼ 11 Investing US

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About The Albatross on Reason.fm

Here you find the Apple Podcasts chart positions of The Albatross, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

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