College football stars shine in private equity

The second-oldest of nine siblings, it would have been easy for Will Weatherford to make his career mark solo, without being smothered by family.

He was on his way, first in real estate and soon after in politics. On the latter, Weatherford, a Republican, had a meteoric rise: He went from campaign employee to Florida State House representative to Speaker of the House in roughly a decade. He represented Wesley Chapel.

But Weatherford didn’t think much about going to work with any of his five brothers. At least not until November 2014, when his Speaker term ended. That’s when Weatherford, now 39, and two of his brothers, Sam, 36, and Drew, 34, chatted about going into business together. The other Weatherfords had been in finance and private equity, and that interested Will Weatherford. “I never wanted to be a lobbyist,” says Weatherford, avoiding the route many take after elected politics. “I couldn’t really get excited about that.”

Those conversations led to the formation of Tampa-based Weatherford Capital, a private equity firm that invests in companies with a combination of its own money and funds from family offices nationwide. In its first four years, Will Weatherford, managing partner, says the firm has quietly amassed a portfolio of eight companies, with three exits. It’s invested more than $100 million since 2015, says Will Weatherford, with an internal rate of return in the top quartile of private equity firms nationwide.

Weatherford Capital is also at a crossroads of sorts: the eight-employee firm has big plans to increase the amount of its investments, to up to $200 million a year — potentially more than doubling its current output. That puts it in the upper end of private equity firms in the region, while also doubling the risk and due diligence side.

The Weatherford brothers — all played college football, including Drew, a star quarterback for Florida State — choose companies to invest in based first on what they call shared values. Not in politics, or business model or industry, but in integrity, high-energy and a competitive streak. 

“We are in a bunch of different spaces,” says Will Weatherford, “but the unifying factor is working with quality people. If someone is just in it for the money and material purposes, it’s not going to work for us.”

Two more factors the brothers seek in investments: businesses, says Will Weatherford, that are “hypersensitive to (finding) value for customers” and firms with executives who practice servant leadership. “We put as much time into analyzing the managers as we do the companies,” adds Drew Weatherford. 

An example of the firm’s investments include PayIt, a software and digital payment platform that works with a myriad of government agencies. Weatherford Capital has invested more than $25 million into Kansas City,-based PayIt, including a significant recent investment. Another major portfolio business is Dallas-based Safe Harbor Marinas, where the investment has exceeded $50 million.

'The unifying factor is working with quality people. If someone is just in it for the money and material purposes, it’s not going to work for us.’ Will Weatherford, Weatherford Capital

Weatherford Capital’s core challenges lie in the hunt, both in finding the just-right deals and securing investment partners from the network of family offices nationwide. Family offices, having grown in prominence over the last decade, are investment arms from wealthy families or individuals. 

Finding solid investment opportunities, say the Weatherfords, is akin to finding a football placekicker who can tackle: it’s rare. The firm looks at hundreds of deals a year, and usually picks three or four, being pickier about managers and potential returns than deal volume. “Debt is so cheap right now,” says Will Weatherford, “and it’s hard to find deals that aren’t overvalued.”