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Today’s gem is this 2021 Forbes article on Robert Brockman (the title is clickbaity, but the content is great… including the Darth Vader image).
You may have heard of Brockman in the news before because of his tax evasion case. But outside of this, there is not much information out there on his actual business dealings & investments (obviously by design). This article is the first I’ve read that highlights how he was a pioneer in vertical market software (VMS).
To put it in perspective, Constellation Software, another early VMS player, was founded in 1995 and reached $1bn capital deployed in 2015/2016. Compare that to Brockman’s VMS empire which by 2000 was already generating enough cash flow that he was able to commit $1bn ($1.8bn in 2023 dollars) to Vista Equity’s first fund. And that’s just a single investment, presumably, Brockman had deployed capital elsewhere too. Not to mention, Brockman had never raised outside equity – this was all his own money.
Brockman’s Universal Computer Systems, founded in 1970, specialized in mission-critical software for car dealerships. It was probably the first-ever truly VMS business. UCS laid the foundation for Vista Equity and its operating practices (which have since been widely adopted by many other software acquirers).
Brockman also set up a complex web of offshore entities to allegedly avoid paying taxes. The IRS indicted him in 2020 on tax evasion charges, claiming Brockman owes $1.4bn in unpaid taxes. This was Brockman’s (known) offshore entity structure:
Brockman passed away in 2022, right in the middle of the tax evasion case, so we may never really know the full story.
Anyway, enjoy the article, it’s fascinating. If a business bio were ever to be produced on Brockman, I would certainly read it.
Shoutout to Turtle Bay for sharing this article.