Financial advisors have unique name, investing approach
January 9, 2026
BENNINGTON — In a sense, Dan Cunningham, the founder and CEO of One Day in July financial advisors, has completed a circle.
His growing firm recently opened an office at 351 Main Street in his former home town. It’s the company’s seventh office in Vermont and ninth overall.
“In some ways it is really special because of that,” Cunningham said. “I still know a lot of people in Bennington, and it is definitely a town where people know each other. Which is nice too, because if you do good work in a town like Bennington, people talk to each other about it.”
Cunningham, who now lives in Burlington where the business is headquartered, added that it’s also fun meeting classmates and others he knew growing up here and going to Mount Anthony Union High School.
“You know, when one of the referees from my middle school basketball days shows up,” he said. “That really adds something special to it all that the other offices don’t.”
The new office is located on the Main Street side of the Putnam Block development at Bennington’s Four Corners.
Area residents can find contact and other information about the business on the company’s website, including how to reach financial advisor John Bass to arrange a consultation.
Company history
Among his primary motivations in creating One Day in July, Cunningham said, was “to lower the costs for people while also not resorting to a call center [service]. People really like to be able to come in and meet a person. They really like to have that consistency over the years where it’s not just somebody in a call center answering a phone.”
Beyond personal accessibility, Cunningham said the unusually named company – and there’s a story behind that – was specifically founded with the idea of emphasizing market index funds that carry low fees and full transparency about the firm’s interests when advising clients.
The company’s fees can be found just below the logo on the website, he said, and One Day in July acts as a fiduciary on its accounts.
“Being a fiduciary means that we are legally and ethically obligated to always put the interests of our clients ahead of our own,” Cunningham said.
Interest sparked
Cunningham went to Princeton University after high school, and at college first became interested in index funds. Those investments essentially follow an index like the S&P 500 Index or the Russell 2000 Index, meaning they generally gain value when stock value in an index of companies rises and lose when it goes down.
This differs from actively managing investments in an attempt to “beat the market” by outperforming a financial benchmark like the S&P 500.
As a student, Cunningham said he read a ground-breaking economic study that showed “almost no one over time was beating the index. You had this gigantic financial industry and no one was beating the index.”
Yet financial advisors benefit from fees related to highly managed investment portfolios, he said, while often promising more gains than they can produce.
“Many, many highly paid people basically had their hand in the cookie jar, and that just seemed incredible to me to have such a big industry that basically wasn’t providing very much to people,” he said.
He added, “I thought that was a very interesting concept, but I didn’t go into the financial field initially, but kept working on [the index concept] after college. And more and more academic work was coming out and showing that this [investing approach] was really bullet proof in its logic.”
About 10 years ago in Burlington, Cunningham said, “More and more people were asking me to take a look at their portfolios.”
Around that time, he read a large longitudinal study “that showed that the average American gets an average of one of every eight dollars of market return. And that was actually the ‘one day in July.’”
According to a post on the company website: “Dan had had enough. It was July 22, 2015, and on that one day in July, he decided this was going to change.”
Cunningham said he knew that a new firm was needed “because I looked at it and just decided that there is no way the industry is going to change itself; it is way too profitable behind the scenes.”
Fees
As he talked to people in the Burlington area about their experiences with financial advisors, Cunningham said, “It was incredible to see how much financial firms were billing people, and almost none of them were above the index. Your chances were really close to zero.
“These people were trusting [advisor firms] with their life savings, and I thought the best thing to do would be to index that with very low fees for people, because that is what the academic work has shown to be optimal.”
He added, “You can always look back at stock market charts and say, ‘Wow, look at that gain.’ But along the way there are a lot of down periods.”
For clients, he said, his firm is “trying to create a more balanced approach where their upside may not be as big but their downside may not be as big either. It makes them a lot more comfortable and helps them to reach their goals.”
No commissions
“It is eye-opening to people how many different ways financial firms are able to make money,” Cunningham said.
He said it is legal for companies “to give commissions to advisors like us and to fly us all over the world at their expense. We won’t allow any of that. We don’t allow anybody to pay us or compensate us through the back door. We really feel that is what we would want if the situation were reversed.”
He added, “We feel clients are hiring us to represent them; they’re not hiring us work for them but then also get paid by funds behind the scenes, and that is all over the financial business; and it’s not just Wall Street; it’s all over Vermont and everywhere else.”
According to a statement on the website: “We do not sell commission-based products and never accept compensation for choosing particular funds. Portfolios are built using only what is best for the client, with the goal of growing and preserving wealth over the long term through clear, cost-effective strategies.”
One Day in July lists its services as investment management, retirement planning and fiduciary advice.
With investments like “IRAs and brokerage accounts to pensions, inheritances, and endowments, One Day In July advisors provide guidance across a broad spectrum of financial needs,” according to the website. “We construct portfolios primarily using low-cost, tax-efficient index funds and maintain client relationships that prioritize transparency and simplicity.”
In a release announcing the Bennington office opening, Cunningham said, “We place a large focus on building relationships with our clients. Every client has a dedicated advisor – someone who really understands their situation and knows their history.”
Putnam Block
In addition, a number of years ago in Burlington he did some work with an organization that was related to initial designs for the Putnam Block redevelopment project in Bennington, where the One Day in July office is located.
“So it is nice to be there,” Cunningham said. “You know, I think there is some new energy. You can really see it downtown; we can feel it as a firm.
“We have a fair number of clients in that area,” he said. “It is a pretty social business so you hear a lot about what is happening, and we think there is a rejuvenation that is occurring in Bennington.”
Bennington County Regional Commission Executive Director Bill Colvin said of the new business, “We are delighted to add One Day in July to the tenant mix at the Putnam Block, as we continue to look to add additional occupancies to further the vitality of both the block and downtown Bennington.”
The firm, Cunningham said, is “generally one of the 50 fastest growing advisory firms in the United States. And I think that is kind of a testament to the trend of indexing, the low-fee, the personal service … And that’s not just Vermont; that’s the whole nation.”
He said One Day in July employs 24 people in its nine offices.
The Bennington office can be reached by calling 802-503-8280, or via email at welcome@onedayinjuly.com.
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