The Tax Cuts and Jobs Act (“TCJA”) of 2017, has been viewed as a “win” for domestic businesses and economic growth, as lower taxes expanded corporate earnings and boosted investor returns. Individual taxpayers also benefitted from tax breaks and touted simplified filing requirements. But, how is one supposed to realize last year’s 20%+ market return, not to mention the over 4x return since the S&P500 bottomed in early 2009, without having to give up a meaningful chunk of those gains to the IRS. Business-builders and entrepreneurs with low cost basis stocks face the same tax planning conundrum. In fact, it is estimated that there is as much as $6 trillion in unrealized capital gains held (or trapped?) in investment portfolios.