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If there has long been an elusive aspect of being at the helm of a hedge fund firm, it is having a proper exit strategy – a way to gracefully bow out of the business, hopefully with some good retirement coin in hand, while ensuring the continuity of the business and the financial best-interests of the other partners and stakeholders.

It is a problem for any big company, particularly an investment shop with a niche or edge that lies in large part with the expertise and even personality of its founder: What happens when the founder decides he’s had enough with the day job?

Among the ways to graciously exit has been to go public or to merge with another firm, giving the remaining partners a healthy stake in the business as well as some incentive to keep it growing. The less-graceful method was to wind the fund down, return capital to investors and hope what was left was enough to retire in Florida on.

But a succession plan of a very different kind announced recently caught our attention, mostly for its unusual approach of merging hedge fund strategies, seeding platforms and exchange-traded funds (ETFs) into a (and here’s the clincher) a dot-com.

The announced deal is that $1 billion hedge fund firm Weston Capital, founded by Albert Hallac, is being bought by Fund.com, a retail platform with a majority interest in AdvisorShares, which develops and markets ETFs.

Fund.com (which trades over the counter under the symbol OTCPK:FNDM), describes itself as “uniquely positioned” at the center of the pooled investment solutions arena, for both the mass and institutional markets. Through its subsidiary, Fund.com Capital Inc., the firm’s stated objective is to acquire asset managers, hedge funds, mutual funds, ETF issuers, investment product developers and fund service providers. (See Fund.com’s stock performance over the past two years, below.)

According to both firms, the merger brings an institutional-focused hedge fund and seeding firm literally onto the virtual desktops of millions of potential retail investors that “will be able to significantly accelerate increases of assets under management since it now has the ability to seed, originate and distribute hedge funds as well as seed, originate, develop and distribute actively traded ETFs to institutional and retail investors.”

Without delving into whether the new entity will have any kind of issue with regulators over marketing and solicitation, we found it both interesting and unusual to see a dot-com concern buy a hedge fund firm – to our knowledge, the first such merger of its kind.

Certainly more than a few analogies have been made of late between the late 1990s and the current market environment: a global financial crisis followed by a plunge in interest rates and a bunch of stimulus packages that eventually fueled a bubble–in 2000, technology, and in 2010, arguably something else. Way back in 2006, we pondered the uncanny similarities between dot-coms and hedge funds.

But a traditional hedge fund and seeding firm going the dot-com / digital route is, to say the least, an innovative exit strategy. Hallac will remain CEO of Weston Capital, directing its day-to-day operations and business strategy, while Fund.com Chairman Joseph Bianco will become Chairman of Weston Capital.

The deal also marks a whole new realm for M&A activity in the hedge fund space. Indeed, it wouldn’t surprise us to see similar mergers unveil, particularly as the line between hedge funds and other types of alternative investments continues to blur, and as investment firms of all stripes cast their nets ever wider in search of capital, particularly in the digital age.

That’s not even to mention the possibility of a hedge fund ETF emerging out of a hedge fund subsidiary of an online firm that offers ETFs, among other investment products. (See chart below of the IQ Hedge Multi-Strategy Tracker ETF, which trades as QAI.)

Source: ETF Trends

Once again, dot-coms and hedge funds have a lot in common. Back in the dot-com boom, hedge funds were making loads of money buying (then shorting) dot-coms. Now, the dot-com is the one doing the buying. Oh, how the tables have turned.

Source: Dot-coms and Hedge Funds: Not Such Strange Bedfellows