Companies Owned by Michael Girdley: Stakes, Investments & Exits

Girdley runs a small-town version of a conglomerate, assembled one relationship at a time in San Antonio. Unlike a fund manager, he does not raise a pool of money and then look for deals; he starts or backs businesses where he already knows the operator, often taking the chairman's seat while a hired or co-founding chief executive runs the company.

The parts have very different cash profiles. Alamo Fireworks earns almost all of its money in two short selling windows around Independence Day and New Year's Eve, which means buying inventory months in advance, financing it, and hoping that drought-driven bans do not cancel a season. Dura Software sits at the other extreme: recurring licence and maintenance fees from more than 3,500 customers, with low capital needs once a product is bought. Hire With Near earns placement and service fees that follow the US hiring cycle.

That mix gives the group a useful internal hedge. A wet summer that hurts fireworks has nothing to do with software renewals, and a weak hiring market barely touches either. The trade-off is that no single management system or set of synergies ties the companies together, so the group's value depends heavily on Girdley's judgment about people and on the quality of each chief executive, such as Paul Salisbury at Dura and Hayden Cohen at Near.

Outside capital has entered at the most scalable points. Peterson Partners' commitment to Dura and Dry Line's investor base behind CyberFortress both bring institutional expectations, board rights and, eventually, pressure for returns. Girdley also earns attention and deal flow from a large social media audience, a paid course on holding companies and the Acquisitions Anonymous podcast. The visible weaknesses are regional concentration, key-person dependence and reputational exposure, which became concrete when Codeup collapsed in December 2023.

Girdley governs from the chairman's seat almost everywhere he invests. He chairs Alamo Fireworks, Dura Software, Hire With Near, CyberFortress and Scalepath, while professional or co-founding chief executives handle daily decisions. That structure lets one person steer five organisations at once, but it also means his influence works through people rather than through day-to-day authority.

The strength of that influence varies by cap table. At Alamo Fireworks, a family company he has led since 2004, his say is probably the most direct. At Dura, Peterson Partners' growth investment of up to $50 million almost certainly came with board representation and consent rights over major decisions such as debt, acquisitions or a sale. At Near, two operating co-founders share founder equity with him. At CyberFortress, control sits with Dry Line Partners as a group, where he is one of three founding partners.

The chairman model suits Girdley's temperament and scale, yet Codeup showed its blind spot. The coding school, which he chaired, assured students on 8 December 2023 that it remained committed to their education, then closed on 28 December 2023. Many students were veterans relying on GI Bill funding. Whatever the underlying finances, the episode shows that a board can lose sight of a deteriorating situation until it is too late for an orderly wind-down.

For outsiders, the useful distinction is between authority and accountability. Girdley's authority at any one company is shared and partly invisible, but his public profile makes him the face of all of them. That asymmetry is manageable when businesses thrive and painful when one fails, because the reputational cost lands on him even where the operating decisions were not his alone. Our view is that his control is broad but shallow, which spreads risk financially while concentrating it reputationally.

There are two Girdleys in the investment record: the civic venture backer of the 2010s and the cash-flow buyer of the 2020s. The first co-founded the Geekdom Fund, helped start Alamo Angels in 2016, sat on the board of the RealCo accelerator from 2016 to 2020 and co-founded Codeup to train local programmers. Those bets aimed to build San Antonio's technology scene as much as to make money.

The second Girdley is more interested in businesses that already make money. Dry Line Partners, formed in February 2021, made its debut by backing Jungle Disk's purchase of three data-backup companies from J2 Global, a deal Girdley said would create the second-largest private technology company in San Antonio. The rebranded CyberFortress gives the partners a services platform with recurring contracts rather than a speculative startup.

Dura Software bridges the two eras. It began as a founder-led roll-up, buying Moki Mobility in June 2018 and Nordic IT and 6Connex in 2019 after a $10 million raise led by Ozone Capital Management, and then, in April 2023, accepted up to $50 million from Peterson Partners to accelerate acquisitions, with a pipeline of more than $25 million of recurring revenue targeted at the time. That deal brought institutional validation and also an investor whose returns ultimately depend on Dura either compounding steadily or, despite its never-sell stance, finding liquidity some day.

Returns from the venture era are not public and early-stage funds take a decade or more to show their quality. We would therefore judge Girdley's investing less by individual outcomes than by the shift in method. Moving from funding startups toward buying profitable businesses, while teaching that approach to a large audience, signals a conclusion drawn from experience: predictable cash beats promising ideas. The lingering risk is that institutional partners at Dura and Dry Line will want exits that sit uneasily with his permanent-ownership message.

Girdley has sold very little, and the one clean sale he made was small. Red Runner Coffee, a San Antonio chain he launched in 2021, was sold after he and his team concluded in late 2022 that other owners would do better with it. He described it publicly as a good business that could redeploy capital at strong yields, which suggests the sale was about focus rather than distress. An earlier seed bet also paid off: ParLevel Systems, a vending-technology startup born at Geekdom, was bought by 365 Retail Markets in 2022 for a price reported in the tens of millions of dollars.

Codeup ended the opposite way. The bootcamp opened in 2013, trained hundreds of developers, many of them military veterans, and charged tuition of roughly $28,000 to $31,000. About a quarter of staff were laid off before it closed suddenly on 28 December 2023, leaving students to chase refunds and transfers. No buyer took over the programmes. That is a failure, and we count it as one rather than dressing it up as an exit.

Some entries on his record are roles rather than ownership. Board seats at RealCo and Propertyaxe ended in 2020, and his product management job at BEA Systems ended in 2000, years before Oracle bought that company. Those departures carry no proceeds and do not belong in a tally of business sales.

Where could a real liquidity event come from? Dura Software is the strongest candidate, because institutional investors such as Peterson Partners eventually need returns and acquired software portfolios attract strategic buyers. CyberFortress is the second, as private equity platforms like Dry Line's normally sell within a fund's life. Either would test Girdley's preference for holding forever, and either would deliver him a share of proceeds rather than the headline price, since partners and co-investors sit alongside him in both. A sale of Dura would also be a public test of whether its never-sell pledge to acquired founders can survive an investor's need for liquidity.