To many casual investors, the current market conditions (Dow Jones now gearing up to test the 15,000 support) have created an environment where double-down investment is untenable. But for Wall Street veterans, stock market analysts, and security-averse millennials--many of which are first-time traders, the new normal of market volatility presents a unique opportunity for speculation. But with the potential for outsized rewards comes the added possibility of catastrophic losses. Nowhere does this Covid-19 trading reality ring more true than in the case of Dell Technologies and VMware.

Since June of 2019, Dell stock traded in range, bouncing back and forth between $45 and $55. Between February 14th and March 20th, Dell stock cratered, eventually changing hands at $28. While it might first appear that Dell’s losses could be wholly attributed to the Covid-19 pandemic, the reality is far less black-and-white. Dell has been piling on debt since 2016, increasing it’s liabilities from 13.48 billion to 52.6 billion. This debt exposure is a cause for concern, highlighted by the weariness of many tech bulls to jump into the discounted stock while simultaneously gobbling up Microsoft, Apple, Amazon, etc. Adding to Dell’s debt concerns is the overwhelming control of Dell by CEO Michael Dell. While shareholders can reap the rewards of Dell profits, there’s always a question of whether shareholder priorities are taken into account regarding company direction.

Then on March 20th, Michael Dell made headlines by doubling-down on his company, insider buying to the tune of 828,199 shares of Dell Technologies Inc. Further complicating the situation is another Dell headline, this time from March 26th: Dell Pulls 2021 Guidance. The company cited the "rising level of uncertainty resulting from the pandemic." So just days after investing north of 26 million in Dell stock, Michael Dell tempered shareholder expectation. And this last development doesn’t even account for VMware, arguably Dell’s golden goose.

VMware is a global leader in cloud infrastructure & digital workspace technology, seen by many analysts as a future behemoth. But just like majority shareholder Dell, VMware pulled their 2021 guidance, after having just reported their projected revenue for 2021 to soar, reaching $12.05 billion.

While it is certainly a positive sign that tech CEOs and Wall Street insiders are confident in a quick economic recovery, there is also reason to proceed with extreme caution. Should the pandemic become more unwieldy than anticipated, and should less-cash-rich companies fail to weather the storm, a bottom-up domino effect could further weaken an already-weakened U.S economy. Lets just hope for the sake of 401k holders, casual investors, and first-time millennial investors that Michael Dell knows something we don’t.