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in one of his recent youtube videosJames Connolly, founder of Root Financial, tries to bust the myth that most of us need to keep working until age 65 to maintain our employer’s health insurance before Medicare kicks in.
“Here’s the uncomfortable truth: It’s the biggest lie that keeps you in a job you no longer need,” he says. “In today’s video, I’m going to show you how Medicare isn’t the gatekeeper to your retirement and what you can do instead.”
Was there a conspiracy? More than 7,900 other viewers of Conol’s YouTube channel were similar.
The post is one of more than a thousand videos and podcasts posted by Conole and his Root Financial partner, Ari Toubalib, since launching the channel in 2017, and is partly credited to Conole for growing his company’s wealth from zero to $2.4 billion in about six years.
“We’ve been able to generate a lot of inbound (customer) demand,” Connolly said of the video and social media strategy. “We try to make it valuable enough that a lot of people want to see it. And we don’t make it complicated or complicated. To do that is a waste of my time and yours, because it’ll just sit on the Internet somewhere and no one will ever see it.”
Encinitas, CA-based Root Financial created money management‘S RIA Edge 100 list for the first time this year. The completely data-driven list includes companies with strong growth rates in AUM, customers and employees, as well as a high percentage of employees with CFP certification, among other metrics.
Along with inbound prospect queries, Root has also seen relatively rapid team growth, adding about 30 consultants over the years. Each of the firm’s advisors has a well-produced, client-facing introduction video on the firm’s website.
Conol knew the value of a consumer-friendly content marketing strategy from his previous success with the popular consumer finance influencer Dave Ramsey’s SmartVestor Pay-Per-Lead ProgramWhich directs incoming queries to qualified consultants.
A somewhat surprising effect of the video content strategy is that it has become a powerful recruiting tool for the firm.
“Once we started posting new jobs after we came on YouTube, there were a lot of people applying who were saying, ‘Hey, we’ve been following your videos for a year or two,'” he said. “Not only are they all involved in what we’re doing because they’re watching, but they’re already somewhat trained on the way we talk and think and the process we go through.”
Root’s client offering focuses heavily on financial planning, including budgeting, retirement strategies, and tax management. The website emphasizes the firm’s focus on “people like you,” though it also notes that most clients have at least $1 million in assets, excluding 401(k)s, real estate and 529 plans. (According to Root Financial’s Form ADV, about 75% of its clients are classified as high-net-worth individuals.)
Root’s consultants use a process developed by Connolly called The Sequoia System, named after the tree with its “deep roots” to “weather any storm.” The system focuses on five areas for creating an individual’s financial plan: finding objectives, reviewing income, optimizing investments, managing taxes, and planning for insurance/estate needs.
Principal Financial Advisor Brett Grau Charles joined Root in 2025 after more than 11 years at Schwab. After interviewing with other firms for years without accepting any offers, he said the ability to provide practical, holistic advice to clients was what attracted him to Root, given his feeling of being restricted in a large financial firm.
“What makes it different is how deep we can go with overall planning,” Grau said. “I can estimate your taxes for this year, and I can look for opportunities like Roth conversions. … It’s really phenomenal how rich these conversations are.”
Grau said in her former job that compliance often sidelined her from such conversations.
“I hope this will change where clients will start asking their advisors for the amount they are being charged,” he said. “At this stage, I think a lot of clients are being charged for things that advisors say, ‘Well, talk to your CPA, you know, or ‘Talk to your estate attorney,’ where really the left hand and the right hand need to talk to each other to do that.”
Grau, who lives in Colorado and is an avid snowboarder, said he expects to stay with Root “for his entire career,” a sentiment he says is not shared by many of his peers in the industry given the movement he’s seen in the broker/dealer and wirehouse worlds.
Conole said he’s trying to keep Root’s technology stack flexible to take advantage of the latest tools for financial planning, tax and estate planning. The company is currently using Right Capital for its financial planning. While it is owned by Charles Schwab, Connolly, motivated by interest in it, has also added Altruist The firm’s artificial intelligence work.
Route is majority owned by Connolly, with Toublib holding a stake. Other employees get a chance to participate in growth through synthetic equity, Connolly said.
And although the founders and team are looking to grow, they said they are not looking for outside capital and have no plans to do so in the future.
“It’s fun to do things that other people aren’t doing,” he said. “This is a very high-performing, fun culture. Why wouldn’t the best advisors in the industry, especially the best emerging advisors in the industry, want to work here and spend their careers here? It’s the core of our value creation process.”
