Taking a Leap of Faith With Some of Cramer's Discards

They may be in the Hurtin' Thirty, but look at McLeod, Akamai and Entrust as long-term options of a sort.
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Jim Cramer's Hurtin' Thirty was the perfect eulogy for an era. It's time to bury the garbage that was foisted upon us by the former Masters of the Universe, otherwise known as the Sand Hill Road crowd and the investment bankers who did their bidding. I will not name names. The world is too small. I might want something from these guys when the next cycle comes around. But, I have to disagree with Cramer on a few of his choices for the Hurtin' Thirty. I hate disagreeing with Cramer because he's so smart.

I'm a fan of intelligent speculation. Not hoping and praying, but rather, placing bets that offer leveraged returns. I believe that a few of the companies on the Hurtin' Thirty list offer great option value. They should be viewed as a sort of Long-Term AnticiPation (LEAPs) option rather than stocks. As with options, investors should be prepared to lose the entirety of their capital. However, there is an opportunity for significant capital appreciation if we get a few of these right. This strategy is not an alternative to buying

Citigroup

or

Viacom

. This strategy is an alternative to going to Vegas. No free drinks, but the odds of winning are considerably higher.

I like

McLeod

(MCLD)

, which Cramer knocked in

Part 5 of his series. The CLEC (competitive local exchange carrier) opportunity is a real one. The Bells control 92% of local voice and data traffic, and this number is going down. The companies in the CLEC sector have been justifiably crushed for terrible capital structure management. The weak economy, too much competition, and the monopolistic tendencies of the Bells have negatively affected operating results.

While the economy shows no signs of getting better, the competitive landscape is improving as numerous emerging carriers go out of business. Additionally, FCC Chairman Michael Powell seems sensitive to the plight of the CLECs. McLeod has reasonably good management, and Forstmann Little (who sits above the common stock holder in the capital structure with preferred stock) has stood by the company. The stock is a dollar. It is never going back to $25. Over the next two years, the stock is going to either zero or $8. It is not a stock. It is an option.

I like

Akamai

(AKAM) - Get Report

. The words "content delivery" and "Internet infrastructure" make me cringe. But they have some of the smartest guys on the planet working for them, and $260 million in cash. As Cramer pointed out,

the name means "smart" in Hawaiian. These are not just smart guys. These are rocket scientists. I like betting on rocket scientists with cash. Who knows what might come out of their laboratory? However, they have $300 million of convertible debt outstanding. This represents stunningly stupid capital structure management. Not exactly Morgan Stanley's finest moment. Oops. I named a name.

The bonds are trading in the 40s with a 24%-plus yield. I like the bonds. When

Cable and Wireless

bought Digital Island, the convertible bonds tripled while the stockholders received no premium. Importantly, Akamai is cutting its burn rate ($73 million to $54 million quarter over quarter) and its capital expenditures ($24 million to $18 million quarter over quarter). Akamai's EBITDA losses are declining at a fast rate. Moreover, they claim to be fully funded. While more people lie about their fully funded status than lie about their golf game or investment performance, I believe these guys. Again, it's not a stock. It's an option.

Finally, I like

Entrust

(ENTU)

. Cramer seems able to generate only the

slightest level of disgust for this company. Actually, fatigue rather than disgust. As Cramer said, Internet security services is a neat little business. The company has $169 million of cash against a market capitalization of $275 million. It lost $14 million last quarter, and is adjusting its cost structure to reflect the hostile operating environment.

Head count has been reduced from 1,200 to 806. The company's revenue mix between software and services continues to improve. Entrust anticipates narrowing losses over the next two quarters and a return to profitability in the first quarter of 2002. Entrust's burn rate is minimal, and it expects to end the year with $150 million in cash. There could be significant upside if these guys execute. Again, it's not a stock. It's an option.

Note: Just a reminder, as of Sept. 10, my columns will no longer appear on TheStreet.com -- they'll only be available on RealMoney.com. I hope those of you who have been reading my column on TheStreet will take a look at RealMoney and decide to join us there. You can sign up for a free 30-day trial by clicking here.

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Brett Messing is partner of Oscar Capital Management LLC, an investment adviser that is based in New York and Los Angeles, registered with the SEC and has approximately $1 billion in assets. At the time of publication, Oscar Capital and its clients were long McLeod, Akamai and Entrust, though positions may change at any time. Under no circumstances does the information in this column represent a recommendation to buy or sell stocks. Messing appreciates your feedback and invites you to

send it along.