Tom Grady, a former Florida financial regulator and longtime ally of U.S. Senator Rick Scott, has become a central figure in a legal battle between two competing tech firms: Rippling and Deel. Grady is named throughout Deel’s recent countersuit against Rippling, which accuses Rippling of engaging in a multi-year campaign to damage its business.

Who Is Tom Grady?

Grady served as Commissioner of the Florida Office of Financial Regulation from 2011 to 2012 and was later appointed to the Florida State Board of Education, which he chaired from 2021 to 2023. He also served on the Florida State Board of Administration’s Investment Advisory Council and was a member of the state Constitution Revision Commission. His political ties to Rick Scott include donations to Scott’s campaigns and mutual appointments across several state positions.

Grady and Rippling.

In 2017, the Naples Daily News reported that Grady was an investor in Rippling, a human resources technology firm. That same year, he incorporated the company’s insurance subsidiary in Florida. Grady disclosed Rippling (under its legal name People Center, Inc.) as a client in financial filings covering 2018, 2020, and 2021.

According to Deel’s lawsuit, Grady continued working with or on behalf of Rippling in later years. Then, in 2023 and 2024, he submitted formal complaints about Deel’s licensing status to the Florida Office of Financial Regulation. He sent these directly to Greg Oaks, the agency’s Director of Consumer Finance, who held that position during Grady’s time as commissioner.

The 2023 complaint alleged that Deel operated as an unlicensed money services business in Florida. The office closed the investigation without action. In June 2024, Grady submitted additional allegations, including claims related to a Deel subsidiary and purported connections to sanctioned Russian entities. The agency also dismissed these allegations as not actionable.

Outreach to Former Employees and Legal Recruitment.

In February 2024, Grady’s law firm apparently began contacting former Deel employees. The outreach claimed there was a congressional investigation into Deel’s employee classification practices. According to public records, no such investigation was ongoing. A March 2023 letter from Trump impeachment leader Rep. Adam Schiff and other House Democrats had called for a Department of Labor inquiry, but even Schiff later withdrew that request.

The Grady firm solicited plaintiffs for potential litigation and collected information through a dedicated email address: DeelTruth@gradylaw.com.

Friends With Zenefits.

In 2016, Grady filed a public records request for documents related to a Florida insurance investigation into Zenefits, the company formerly led by Rippling CEO Parker Conrad. The investigation had not yet been made public. Zenefits filed a lawsuit to prevent the release of the documents, citing trade secrets. Grady later withdrew the request without explanation.

In 2017 and 2018, Grady reported receiving consulting income from Zenefits, according to financial filings.

NY & CA Liberal Takes Sudden Interest in Funding Republican Rick Scott.

In October 2024, Parker Conrad, now Rippling’s CEO, made several political donations to Florida political entities connected to Senator Rick Scott. These included:

• $5,000 to Team Rick Scott (October 18, 2024)

• $3,300 to Rick Scott for Florida (October 23, 2024)

• $1,700 to Let’s Get to Work PAC, a Rick Scott-aligned PAC (October 23, 2024)

Conrad also contributed to Kamala Harris’s campaign and had previously maxed out to Joe Biden. Until then, his federal political donations had been directed exclusively toward Democratic candidates. The contributions to Rick Scott-aligned groups represent a notable departure from that pattern, made as Deel and Ripplings were preparing for court.

Conrad was born in New York, studied in Boston, and lives in San Francisco. He has no public affiliation with Florida beyond the regulatory interactions related to the Deel case.

Grady’s Education Nonprofits.

Grady is president of a group of affiliated nonprofits and for-profit education companies in Florida, operating under the Freedom Institute and Quest Educational Foundation names. These groups provide standardized test preparation and college counseling to students in Naples.

Their funding includes state dollars from Florida’s Personalized Education Program (PEP). According to IRS filings, the organization spent $32,748 on curriculum and activities in its most recent year while allocating over $800,000 to salaries and compensation. It also reported $1.5 million in assets managed by Naples Global Advisors, a firm Grady is reported to have invested in and shares an address with his law office.

As of its most recent filing period (July 2021–June 2024), the organization owed more than $160,000 to The Village School of Naples, categorized as “federal income taxes.”

Ongoing Litigation.

The legal dispute between Rippling and Deel is ongoing. Deel’s countersuit accuses Rippling of coordinating a campaign to harm its business interests using legal, political, and regulatory channels. Grady’s role as an intermediary is a key element of Deel’s case. The allegations remain subject to court review and discovery, and as it proceeds, don’t be surprised if the likes of Senator Rick Scott are asked what they knew about all this as it unfolded.

From the moment Trump launched his 2016 campaign, he was under scrutiny by the Federal Bureau of Investigation, which ended up probing him for more than two years for allegedly working with Russia to win the 2016 campaign.

When the Russia investigation failed to land any luck for Democrats, they turned to impeaching him not once, but twice. Eventually, civil lawsuits ensued. But the worst of it may have been the four criminal prosecutions he faced, making history as the first time a former president ever stood trial and was convicted of a crime.

Don Jr., the eldest son of the president, said he does not think his father is bothered by being labeled a “felon” or a “convict.” He told me that, like the mug shot taken in Fulton County, Georgia, over Trump’s state prosecution there, it has all become “sort of a symbol for standing against the corrupt swamp establishment and standing with the tens of millions of everyday, commonsense Americans who supported him.”

“In a weird way, the courtroom sketches, the phony witch hunts, the failed Democrat ads, and the mug shot—it all became sort of a badge of honor, because it represents a courageous and bold stand against abuse of power. It’s a political comeback story like we’ve never seen. And no, I’m not tired of winning,” Don Jr. said.

He also credited the love and loyalty of the American people for motivating the Trump family to continue to campaign despite the mountain of lawfare.

“In fact, the lawfare only made us that much more driven and eager to deliver on the promises to restore equal justice and equal application of our laws. We’re a family of builders—and when you’re building something, you don’t stop until the job is finished. The more the corrupt left-wing lawfare cabal tried to bring him down, the stronger my father became. Because once the corruption got to a certain point, we had no choice but to work harder than ever to deliver a massive victory in November.”

Lara Trump, for her part, said that one day the family will feel comfortable coming out and talking more specifically about the way the political targeting that started nearly ten years ago has impacted each of them, adding that “it has upended all of our lives.”

“It has been very, very damaging to all of our lives in ways probably people couldn’t fathom. When that day comes, I think people will be utterly shocked by the things that have happened to our family and we made it through. I am grateful to the American people that they saw through all the lies and the lawfare and all the nonsense. But it is a really scary process that, had things gone the opposite way in this election, I don’t know what that would have meant for our family, for my father-in-law, and for this country as a whole, because I think once you go past a certain point, I don’t know that you get this country back. So, I feel like we are very fortunate right now.”

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Arguably, America’s decades-long housing crisis was one of the issues that helped propel President Donald J. Trump into office—and rightly so. Decades of establishment failures (read: self-enrichment) have worsened an already dire situation. Soaring prices, stagnant wages, regulatory bottlenecks, and Bidenflation pushed home ownership further out of reach for ordinary people. Trump’s answer on the campaign trail has been consistent and correct: build more homes, and clear the roadblocks that make them unaffordable in the first place.

Under Biden, the home price-to-income ratio hit a record high. In 2022, a median-priced home cost 5.6 times more than the median household income. That’s the worst spread since the early 1970s. The reasons are obvious: inflation, interest rates, excessive taxes, environmental restrictions, and a shrinking supply of available homes.

Trump’s approach is straightforward: get Washington out of the way, and get America building again. Most Democrats, by contrast, seem to want to avoid this outcome. Despite finally admitting that Biden was an effective Oval Office vegetable, they still won’t repudiate Bidenomics. Naturally, they’re lashing out at private sector investment in the single-family rental (SFR) market—one of the few sectors offering working families a path to stability and home ownership.

Single-family rentals are not the problem. They’re part of the solution. They provide access to good neighborhoods and schools at a lower monthly cost than owning outright, which is often critical for my generation, especially those who graduated at the onset of the 2008 crisis and recently endured COVID lockdowns. Right now, renting can save families about 40 percent compared to mortgage payments. Even in a world where we want more home ownership, that matters.

Yet California, Georgia, Nevada, and North Carolina lawmakers are pushing legislation to cap the number of homes providers can own. These proposals are based on the false assumption that providers reduce housing supply. The data doesn’t actually support these claims, by the way. According to the Mercatus Center, institutional investors have never accounted for more than 2.5 percent of home purchases in a single quarter. That’s not exactly a takeover of the market.

Private investment increases the housing supply, creates jobs, and expands options. Attacking the private sector may score points on MSNBC, but it won’t build a single home.

Democrats are attempting to restrict the very actors capable of building, maintaining, and managing housing stock. This is a destructive approach to one of America’s biggest problems. Trump understands what’s required: deregulate, incentivize construction, and keep the government as far out of the situation as possible.

If Washington wants to help Americans become homeowners again, it should stop demonizing investors and remove obstacles. That means cutting bureaucracy, slashing taxes, rolling back zoning restrictions, and encouraging development. It means leadership with clarity and urgency—something the Biden White House never displayed.

Trump has. He’s laid out the blueprint. Americans need affordable homes. The private sector is best placed to deliver. All that’s required is the political will to stop worsening the problem.

Image by Pexels/Brett Sayles

In a world rife with evolving national security threats, immigration policy must be more than a humanitarian exercise—it must be a firewall. Unfortunately, that firewall developed gaping holes under the Biden government, as evidenced by the Department of Homeland Security (DHS) Office of Inspector General’s (OIG) June 2024 report. The report makes clear what many of us have long feared: that systemic failures in our immigration and asylum vetting process are putting Americans at unnecessary risk. Fortunately, President Donald Trump has the record and the roadmap to fix it.

The OIG’s findings paint a troubling picture.

Between October 2017 and March 2023, over 400,000 affirmative asylum applicants were not properly vetted because U.S. Citizenship and Immigration Services (USCIS) failed to fully utilize all federal databases, including critical classified data sources.

Meanwhile, Customs and Border Protection (CBP) lacked access to key information to screen migrants crossing the border. This isn’t a clerical error—it’s a critical national security vulnerability, potentially allowing bad actors to exploit our follies.

EXTREME VETTING.

President Trump’s Executive Order 14161, signed in early 2025, wisely recognized this danger and moved to restore rigorous screening processes across the federal government. In contrast to the Biden era’s open-door naïveté, EO 14161 returns to the core doctrine that defined Trump’s first term: extreme vetting.

The term—coined by Trump in 2016—captured the national mood then and remains even more relevant today. But reinstating vetting protocols isn’t enough. We must fund them sustainably and fairly. The solution? Charge visa applicants from high-risk countries a supplemental fee to finance their own enhanced background checks.

Think of it as a “national security co-pay.”

If you want to enter the United States from a nation with a documented history of terrorism, failed governance, or limited identity infrastructure—Syria, Afghanistan, Yemen, Somalia, and the like—you must pay an “extreme vetting fee.” This is not a punishment; it’s policy with a purpose. The U.S. taxpayer should not be financially penalized for shouldering the costs of assessing whether a Syrian national spent the last five years working in a store or a sleeper cell.

America has finite resources. The Biden government failed to allocate or coordinate those resources, allowing asylum backlogs to balloon while scrutiny waned. Their own Inspector General literally wrote the book on the damage. Trump can fix that—not by throwing more taxpayer money into the bureaucratic bonfire–but by making the system’s users pay into it.

Some will cry foul, claiming this introduces a barrier to entry for impoverished refugees. But let’s be honest: if someone from a terrorist hotbed can’t afford an extra $200 so we can dig deeper into their background, do we want them? This is not about denying access to the truly vulnerable; it’s about denying entry to those who think of our vetting process as a box-check instead of a national security gauntlet.

And yes, deterrence has its place. If a would-be applicant from a war-torn region rethinks their plans because the vetting process is too rigorous or too costly, that’s not a bug—that’s a feature. The United States is not obligated to open its doors to every person seeking a better life. It is obligated to protect its citizens first. Every dollar we fail to spend wisely on immigration security is a dollar we may spend responding to attacks, criminal activity, or even bureaucratic chaos.

JOINING AN INTERNATIONAL CONSENSUS.

Let’s also address the elephant in the policy room: even under the best conditions, verifying the identities and intentions of migrants from unstable nations is extraordinarily difficult. In Afghanistan, for example, biometric data may be inconsistent, records may have been destroyed, and corruption can undermine documentation. In Syria, passport fraud is rampant, with ISIS and other groups having exploited government printing presses to produce fake credentials. In these cases, the notion that we can vet applicants on a shoestring budget is laughable. We need not just more data, but more time, more cross-agency collaboration, and more human intelligence—all of which cost money.

President Trump understood this from the outset. His original travel restrictions in 2017, heavily criticized then, were eventually upheld by the Supreme Court because they reflected a sober assessment of risk, not an arbitrary rejection of immigrants. Critics shouted “Muslim ban” while ignoring the actual methodology: countries were chosen not based on religion, but on their ability—or failure—to provide reliable information for vetting. That principle should guide any future Trump policy, only now with added teeth: If we go to extraordinary lengths to confirm that someone is not a threat, they should help pay for that effort.

Such a policy would not be unprecedented. The United Kingdom already charges noncitizens visa fees scaled by category and risk. Australia levies surcharges for security and medical screenings. These countries understand that sovereignty is not free, and neither is safety. By implementing a risk-based pricing model for visa vetting, the U.S. would join this rational global consensus.

PAYING FOR THE LOCKS.

Moreover, this strategy would help depoliticize immigration enforcement. Instead of debating abstract quotas or arbitrary bans, we would apply an objective financial filter tied directly to risk. Want to migrate from a stable, transparent country? Fine—your visa costs stay low. Want to enter from a nation where vetting takes three times longer due to fractured civil registries and terrorist infiltration? Prepare to pay more for the privilege.

Most Americans support this kind of common-sense approach. A 2023 Pew Research poll found that 72 percent of Americans favor stronger vetting for migrants from high-risk countries, and a majority believe immigration should be tied to national interest rather than emotional appeals. The Biden government ignored this sentiment. A second Trump term must embrace it. Trump has secured our Southern Border with Mexico – now he must clean up Biden’s mess and secure our visa process.

“Extreme vetting” is not a buzzword—it’s a necessary evolution in a dangerous world. The most effective way to operationalize it is through a sustainable, self-funding mechanism that aligns with fairness, accountability, and national interest. The Trump Administration can make it official policy: If you want to come to America, you’ll have to go through the front door—and help pay for the locks.

Matt Gaetz served on the Judiciary and Armed Services Committees of the United States House of Representatives from 2017-2024. He hosts “The Matt Gaetz Show” nightly on One America News.

Image by Gage Skidmore (CC)