James Lepore founded Cascade Financial in his hometown of Wooster, Ohio. He came to this work by choice, learned it one family at a time, and built the discipline before he built the firm.
James’s working life began on a manufacturing floor here in town, cutting titanium to spec. In that world, risk is not an abstraction. A gap in the process becomes a loss with a date and a dollar figure attached. The habit of naming things and counting them was formed there, years before it had a strategy named after it.
James went west after school and spent the better part of a decade managing other people’s operations: a Best Buy service department, then five years with Starbucks, where he ran a high-volume store and a team of fifteen. The financial career started at a folding table. James was working a Saturday booth in Washington State when he struck up a conversation with the man at the next table, a financial advisor named Sterling Gurney. James had assumed the work required a finance degree and years in the industry. It required, Sterling said, the intangibles and the willingness to do the job. James applied that afternoon with Sterling’s name on the form, started with Edward Jones that October, passed the Series 7, Series 66, and insurance exams over the winter, and spent the first months of 2017 knocking on doors in Mount Vernon.
Four established advisors in town had each handed the new office a slice of their books to start it. A year and a half later, one of them, a senior leader in the region, came back and entrusted fifty of his own families to James. Experienced advisors do not do that on a hunch. They do it after watching.
By the third year the door-knocking was over. From 2020 on, the practice sustained itself on referrals alone, and some of the strongest relationships of those years were opened, planned, and funded entirely over video with people James has still never met in person. One couple, a self-employed electrician and a hair stylist sent by a friend, never once turned their camera on. The method held without the handshake.
Fifteen years away ended where everything began. James returned to Wooster and founded Cascade Financial as an independent practice, affiliated with LPL Financial, because examining the whole of a family’s picture requires an open platform with nothing of its own to sell. The office sits a block off the square downtown, a few minutes from that first shop floor. Most conversations happen over Zoom, with families anywhere in the country.
Hundreds of relationships taught James one pattern. When a plan got into trouble, the trouble almost never started with the portfolio. It started with a risk nobody had named.
Early on, a couple came to him expecting a fortune. They had lent money to a man who claimed to have invented a new kind of engine, and had been promised a share of the patent sale. Their daughter was sending him money every month. James asked for the documents any real transaction would produce. Nothing came. Over several months he helped the family understand that there was no patent, no buyer, and no money on the way, and then helped them untangle themselves from it. He never earned a dollar on that engagement. It remains the clearest example he has of what the work actually is: not choosing investments, but finding the thing that will hurt a family before it does.
The same instinct built the method he used with retirees. Work out what a household actually needs to live on. Fund that from income the portfolio produces, so the check arrives whether or not the market cooperated. Invest the remainder for growth. Families who know the floor is under them can sit through a bad year without selling at the bottom, and most of the money James has saved clients over the years was saved that way.
“The question is never what to buy. It is what will hurt this family, and whether anyone is watching it.”
Sell what the house makes. He turned down an offer from an insurer whose advisors could only sell the insurer’s own products, and chose LPL for the opposite reason. The right tool for a family might be an annuity, an insurance trust, a hedge against the dollar, or a portfolio of ordinary index funds. It should never be the thing the firm needs to move this quarter.
Build the portfolio first. The investments are one of ten parts of a family’s picture, and the last one James settles. He will not put money to work until the risks around it have been named and numbered, because a well-built portfolio inside an unexamined picture is still exposed.
Take a token account. If a family is not ready to share the whole picture, the honest answer is not yet. A small account opened as a courtesy serves no one, and James has learned not to accept one.
James and his wife are raising five children in Wooster. His grandmother was raised here, and a great-grandfather was the Lutheran pastor in Smithville, so the roots on his mother’s side run deep in the county. The practice was built to run over Zoom so that home could be chosen rather than assigned, and James chose the one with his mother, his sister, his kids’ cousins, and a YMCA with three pools.
His years of service outside the practice include eight on the councils of his Orthodox parishes, in Washington and now in Ohio, and a term as president of a business referral group in the Pacific Northwest, where he rewrote the bylaws so that a networking meeting could stop pretending to be a board meeting. Both jobs have the same spine as this one: show up, keep the accounts faithfully, and be answerable to the people who trust you.
Ask his wife what he is like with money and she will say he treats it as a tool. Not the goal, and not the score. The thing that lets a family spend time with the people who matter to them and build what they care about.
“A practice built where you are raising your children is a practice you answer for at the grocery store.”
James holds the FINRA Series 7 and Series 66 through LPL Financial and has advised families since 2017: Edward Jones from 2016 to 2024, Cascade Financial since. He holds a Bachelor of Arts in History from The Ohio State University. Check his background at any time on FINRA’s BrokerCheck. We would rather you look than wonder.
You now know more about the advisor than most families learn before a first meeting. What remains is the part that matters: an unhurried hour, both decision-makers present, about your picture rather than ours.
201 E Liberty St, Suite 100B · Wooster, Ohio · (330) 201-8760 · james@cascade.financial