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Reggie Middleton
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As a serial entrepreneur and perpetual student, Reggie Middleton's unconventional experience has given him the ability to recognize value, or the lack thereof, well before much of the professional populace. His ability to identify opportunity and his "out-the-box" mind-set are due to years of entrepreneurial pursuits in insurance, financial valuation/modeling, technology, media, and real estate

After attending Howard University in Washington, D.C. from which he obtained a BBA in business management. Reggie returned to NY and joined the ranks of Prudential Insurance, training in financial product sales. Feeling constrained in his ability to pursue institutional clients, he moved to a small securities firm and became a series 7 broker. Again feeling constrained in his ability to creatively pursue his ideas, in his early twenties he struck out on his own and created margined mutual fund timing programs for his own trading account. This was the first in many unorthodox proprietary investment and risk management strategies Mr. Middleton has created .with great success

In the early 1990s, Reggie, an entrepreneur in his early twenties, entered the insurance and risk management field by brokering insurance for entire municipalities and political subdivisions on an exclusive basis. He also conceptualized, marketed, jointly prepared and submitted LORIE (the Livery Organizations Reciprocal Insurer Entity - a reciprocal insurer owned by the insureds) - to the NYS insurance department for licensing.

Reggie then formed Municipal Risk Management - a venture with a major accounting/consulting firm to offer risk management, consulting and brokerage services to small and medium sized municipalities.

Mr. Miiddleton also pioneered derivative and structured product use in health insurance via his concept, "Financial Re", a tax advantaged, ERISA compliant, off shore financial reinsurer. It was designed to securitize FASB 106 retirement medical liability risk to be sold through the debt markets using Reggie's own ‘Max Notes' (option embedded notes linked to a proprietary medical loss index). He recruited the assistance of partners from the big five accounting and consulting firms for purposes of validating and marketing Financial Re's derivative debt securities. These securities (Max Notes) had near-zero correlation to conventional equity and debt markets and as such were designed to appeal to institutional investors looking to diversify risk.

In the midst of the boom era, Reggie, a self-taught technology buff and student in financial valuation, recognized opportunities to incorporate his passions for technology and financial valuation and transitioned to the distributed technology and media industries Again, as an entrepreneur, Reggie created, marketed and sold web-based, decision support and financial modeling systems featuring file sharing, collaboration and team based productivity for M&A, LBO, private equity and corporate valuation deals. These high-end financial models, financial modeling techniques, corporate valuation techniques, and methodologies quantitatively captured the intangible assets from technology companies that represented a significant portion of their value such as human capital, brand value, viral marketing and network effects. Reggie's modeling experience includes information technology TCO/ROIC, LBO, M&A, private equity analysis and valuation, financial derivatives, partnership valuation, real estate analysis and valuation, derivative and structured product engineering, and corporate valuation via proprietary economic profit methodologies.

Mr. Middleton was one of the early entrepreneurial dot.commers to adopt the off shoring model, coding entire software platforms at below market cost through engineering relationships with off shore IT consulting shops & development sites in Bangalore, India. In addition, he expanded this platform to a full featured Application Service Provider platform, web-based office suite and web-based collaborative knowledge sharing platform - known as NuoMedia, which competed with Microsoft's Office suite as a desktop office productivity solution. NuoMedia was the first to market publicly available Web-based office productivity suite and first to be introduced to the public through the media (beating Microsoft and Sun Microsystems as seen in Reggie's interview on CNNfn's Digital Jam, Sept. 1, 1999).

Mr. Middleton began investing in residential real estate, sensing the boom portion of the boom bust cycle in the year 2000. He engaged in real estate investment/management, returning several multiples of the broad market averages, approaching four digit returns from 2000 to 2006.

Sensing the top of the real estate market in 2004, Mr. Middleton started liquidating his portfolio and searched for alternative assets in which to invest. Failing to find any real assets worth pursuing, he spent a year caring for his newborn daughter while contemplating his next venture. In 2007, he opted to start a private alternative investment fund consisting solely of his own account, which could benefit from what he saw as an extremely overpriced credit and real asset market entering the bust phase of the boom-bust cycle. As a fine tuning of his Boom Bust micro/macroeconomic investment methodology, which was an extension of his technology and real estate investment principals, he implemented these principals in his trading account as a real-time demonstration while documenting them publicly via the The blog is a global macro investment publication through which he freely publishes his research, opinions, and reasoning behind his investment decisions.

Blog Entries by Reggie Middleton

Less Than 24 Hours After My Warning of Extensive Legal Risk in the Banking Industry, Massachusetts Supreme Court Drops the Bomb

Posted January 11, 2011 | 04:07:26 (EST)

The day after I posted “As JP Morgan & Other Banks Legal Costs Spike, Many Should Ask If It Was Not Obvious Years Ago That This Industry May Become The “New” Tobacco Companies” wherein I made clear my opinion that the legal and litigation risks that the banking industry...

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Is Illinois Worse Off Than Greece With a Little LTCM and Bear Stearns Thrown In?

Posted August 23, 2010 | 16:34:40 (EST)

In early 2008, I warned my readers that several states and municipalities in this country are going to run into some very rough times, with the spectre of default definitely on the table for a few. See Municipal bond market and the securitization crisis – part I and...

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Black Eyes for the Blackberry? A Complete Forensic Analysis of Research in Motion

Posted August 20, 2010 | 14:56:22 (EST)

A couple of weeks ago, I penned the piece “After Getting a Glimpse of the New Windows Phone 7 Functionality, RIMM is Looking More Like a Short Play“. As explained in that article, many are prematurely discounting the success of Microsoft in the mobile space. It wasn’t the...

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Empirical Evidence of Android Eating Apple

Posted August 17, 2010 | 16:10:15 (EST)

Android's market share is growing by nearly 900%, causing competing OSs and associated hardware vendors to experience negative smart phone market share gains. Many believe that Apple is not included in this category. Here I present hard evidence that Android is eating Apples along with everything else.

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How Google is Looking to Cut Apple's Margin and How the Sell Side of Wall Street Will Enable It

Posted August 12, 2010 | 17:21:42 (EST)

The Apple Forensic Analysis and Valuation is nearly complete and will be available to subscribes in a few days. In the meantime I will discuss a few salient points and logic that went into the design of the model. As I have said several time in the recent past, Apple...

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What Do Goldman Sachs and B.B. King Have in Common? The Thrill Is Gone, Baby!

Posted August 10, 2010 | 13:21:25 (EST)


From Bloomberg: Goldman Sachs Lost Money on 10 Days in Second Quarter

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Lodging Management Spins Crafty Tales as Consumer Macro Data Continues to Verify What I Susptected All Along - We Never Left the Recession!

Posted August 6, 2010 | 16:05:23 (EST)

A few days ago I warned my subscribers that the lodging industry, and the economy as a whole, were not truly recovering to any material extent (see and We Think Management Have Been a Little Optimistic). Y-o-Y comparisons made...

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RIM.... Hmmm... Maybe RIP: Crackberries in the Smart Phone Wars...

Posted August 4, 2010 | 11:25:13 (EST)

Last week I stated “After Getting a Glimpse of the New Windows Phone 7 Functionality, RIMM is Looking More Like a Short Play“. I meant it,...

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Math and the Pace of Smart Phone Innovation May Take a Byte Out of Apple's (Short-lived?) Dominance

Posted August 3, 2010 | 15:59:45 (EST)

It appears to be official. Apple’s iPhone is no longer the fastest growing smart phone in the world’s largest and most important smart phone market – the US! This is a very critical time for Apple and its investors, for Apple has executed wonderfully in the smart phone space and...

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A New Spin on Bank Fraud: Banks Defrauding Their Investors, Auditors and Regulators, Which Also Helps Delinquent Mortgagees

Posted July 28, 2010 | 17:45:28 (EST)

Last week, I made clear to my readers and subscribers that the bank malaise is not over, despite what may appear to be encouraging moves by the executive staff. Housing prices are still on their way down, save temporary blips from government bubble blowing and the outright concealment of non-performing...

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Are Blogs Truly Competitive With the Mainstream Media in Terms of Quality of Content?

Posted April 21, 2010 | 13:56:10 (EST)

A very interesting article was published in Crain's New York this morning, both in print and online, titled Prophet of doom. The article was about blogs, and the potential for them to raise capital and compete with the mainstream media. There's...

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Is the Threat to the Banks Over? Implied Volatility Says So

Posted April 3, 2010 | 13:14:37 (EST)

Implied volatility for the big banks is down across the board, just about where it was before the system went into convulsions. This implies the coast is clear, as do the share prices of many banks.

Hardcore forensic and fundamental analysis implies otherwise. So does the Fed's...

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Lies, Damn Lies, and Sovereign Truths: Why the Euro Is Destined to Collapse!

Posted March 24, 2010 | 16:20:00 (EST)

If this article goes viral around the web, I wouldn't be surprised if the euro tanks and several European sovereign states' spreads blow out. I have busted several of them in another of a long series of "creative" economic forecasting schemes to fudge the appearance of "austerity."

Well, its official...

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Amid a Depression and Linked Heavily into Western Europe, Latvia's Government Collapses Today!

Posted March 19, 2010 | 13:51:32 (EST)

From the UK TelegraphLatvia government collapses amid economic crisis.

The People's Party, the largest group in a five-party coalition, walked out amid disputes over how to cope with the country's severe problems.

Unemployment has now hit 20 per cent and the economy contracted by 18...

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Lehman Brothers Dies While Getting Away With Murder: Regulatory Capture

Posted March 12, 2010 | 07:13:26 (EST)

Let's get something straight right off the bat. We all know there is a certain level of fraud sleight of hand in the financial industry. I have called many banks insolvent in the past. Some have pooh-poohed these proclamations, while others have looked in wonder, saying "How the hell...

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It's Official: The US Housing Downturn Has Resumed in Earnest

Posted March 12, 2010 | 05:39:23 (EST)

The year 2009 was the year of reflation theories and bubble blowing. Theses of "Green Shoots", catching the bottom, and QE reigning supreme were the order of the day. Sure enough, asset prices (nearly all of them) went one direction, straight up. We all saw it coming, but guys...

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The Depression is Already Here for Some Members of Europe, and It Just Might Be Contagious!

Posted March 12, 2010 | 04:22:50 (EST)

This is the 2nd to last installment in my Pan-European Sovereign Debt Crisis series. After covering western and southern Europe, we are moving eastward. Before we go any further, be sure you have caught up on the previous portions:

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Smoking Guns Are Beginning to Litter EuroLand, Sovereign Debt Buyer Beware!

Posted March 12, 2010 | 04:11:03 (EST)

There are broad indications hinting that Italy and Greece are not the only countries that have used SWAP agreements to manipulate its budget and deficit figures. France and Portugal may be two other European economies which have resorted to similar manipulations in the past in order to qualify as part...

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Reality Check for Bank Investors, Mortgage Investors and Home Buyers

Posted March 12, 2010 | 03:35:27 (EST)

Last week I posted a Bloomberg news article supporting my suspicions that investors are putting bad loans back to the banks at an increasing rate. I used JP Morgan as a specific example -Banks Swallow Another $30 billion or So in More Losses as Their Share...

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The Uncosted Rewards of Bankers' Bonuses

Posted March 11, 2010 | 17:40:10 (EST)

This post originally appeared on the Financial Times' website,

A bank employee recently asked me: "As a trader, my bonus is derived directly from my profit and loss, which is accrued over the quarter and kept in a separate account. It does not go into...

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