Brokers
James Webster to Speak at Broker Fair 2025
March 31, 2025
James Webster, Founder and Executive Chairman of ROK Financial, will be a guest speaker at Broker Fair in New York City on May 19th.
James brings a passionate and innovative mindset to the businesses he and his company help grow on a daily basis. Since the age of 18, James has managed multiple sales floors, which allowed him to develop a strong business understanding and a passion for small business.
With nearly two decades of experience in financing and commercial lending, James and his team have helped thousands of business owners secure nearly $2 Billion in business financing, created thousands of new relationships with partners and strengthened their lender relationships, making them a true leader within the landscape. James and the team pride themselves on helping businesses identify their strengths and weaknesses, as well as educate them on the ways they can build on their successes by creating perpetual opportunities with business financing.
In addition to his role at ROK, James sits as the co-chairman of the Small Business Financing Association Broker Council, a non-profit advocacy organization dedicated to ensuring that small businesses can access financing solutions that are clear, secure, and fair. In this role, James establishes responsible and transparent practices for alternative lending brokers while also educating policymakers and regulators about the technology-driven platforms that have emerged in the small business lending market.
James was born and raised on Long Island where he currently lives with his wife, Melissa, and their two children, Lilyanna and Jameson. He is an active member of the Long Island community and feels a special connection to local businesses. Philanthropy plays a big role in James’ personal and business life. ROK’s main philanthropic initiative includes donating 50 meals for every deal that funds with ROK Financial, with the hope of helping end hunger in America.
When not at the office, You will either find James on a golf course or enjoying his other interests such as skiing, fishing, boating, traveling, live sporting & music events but, most of all, spending time with his family!
Role-playing and The Value of Practicing Sales Calls
March 31, 2025deBanked asked several brokers over the past month about the value of role-playing with colleagues to prepare for real life sales engagements. Below are some excerpts of what they said.
Cheryl Tibbs, Commercial Capital Connect: “Before my broker life, I was a call center supervisor, so just really familiar with call centers making cold calls and that type of thing. So it’s very important [to role play], I think you have to practice. You don’t want to read a script, you don’t want to sound robotic, but you want to be engaged enough where you can have a good conversation with people without having to really think about it.”
Is there a point where practice is no longer necessary?
“Our industry changes day-to-day, little by little, things are changing. So I think it’s just always incumbent upon us to sharpen our skills. That means practicing at least once a week.”
Josh Feinberg, Everlasting Capital: “Role-playing is like stretching before going for a run. It makes it possible for you to be fast on your feet and really be able to have the answers when you’re talking to a, let’s just say, a construction company that does equipment financing, and they’ve financed all of their equipment. A lot of times they’re going to be more knowledgeable about the equipment financing and leasing product than a lot of the brokers that are going to be talking to them in regards to it.”
Is this something you do with your own reps?
“Yes, especially when someone is newer or starting out, role playing is essential to even a point just like on Equipping The Dream, we need to make sure that we’re call-coaching too. While we’re listening to them on the phone we’re in their ear telling them what to say, just to have them get used to it. And then we do a bunch of different role playing…we’ve done it hundreds and thousands of times over the years”
Adam Oster, Canyongate Financial: “We have a set list of questions: understanding the merchants needs and building that relationship. And if I know somebody’s really good but they’re not doing well, then we’ll go back and say, ‘Hey, let’s role play. Because there’s something—you’re too complacent, you’re missing something, or you’re not listening to the customer.’ So role play is very important.”
How does this take place?
“If they’re here locally, we’ll do it in-house a lot of times. I’ve got a couple people—one in California, one in Austin, Texas, so we have to do it over the phone. And if somebody’s thriving, I’ll ask them, ‘What are you doing? What are you saying to your dealerships or your customers that are helping you get deals?'”
How Mike Brooks Battled in the Ring and Won Top Broker in Equipment Financing
March 6, 2025
“Equipment Financing is HUGE,” declares Mike Brooks, CEO of New York-based Best Connect Capital and recent winner at Broker Battle 2025 in the equipment finance category at deBanked CONNECT MIAMI. If his name sounds familiar, it’s probably because he appeared on stage as one of six finalists in the previous year’s competition. He refused to give up after his loss and returned this year for round two, leading to him securing a title and prizes along with it. To hear him tell it, it had been a long road to get there.
When Brooks got his start as a 27-year-old broker in 2015, for example, he had technically been battling in a ring for most of his life already.
“I had [boxing] on my mind in high school, without any influence,” says Brooks, “and I walked into a gym one day and the rest was history.” That history includes 60 fights in just amateur-level boxing, resulting in 45 wins and 15 losses. When he followed that at the pro level he went 11-2-1.
“I started fighting at the regular club shows, the Golden Gloves, the metro tournaments, national tournaments, and at one point, I was ranked number seven in the whole country,” Brooks recalls. “I beat some really good fighters, lost to some really good fighters and I made it to the highest levels in the country.”
Some of those fights even aired on live TV. As he bobbed and weaved for years in the ring, he started to think about what a possible career in business might look like afterwards. When that day came, he went to work for a local financial service company on Long Island who taught him about helping small businesses access working capital. Eventually he realized it was a business that he was uniquely suited for and now he runs his own company doing it.
First, there’s the endurance aspect, he explains. There’s a lot of calls, leads that don’t pan out, and heartbreak that hits when deals get declined at the finish line.
“A very small percentage of people can be a successful broker,” Brooks says. “You have to be able to take rejections all day long.”
To that point, Brooks noticed that as the industry grew he was not the only broker offering revenue-based financing to a client. Sometimes there were even as many as four or five other brokers talking to the same client at the same time, which meant that he wasn’t going to win every one and he did not want to bend his ethics just to eke it out. That’s when he started considering another approach and expanded his offerings.
“An equipment financing deal was my first big check during [the covid] lockdowns,” Brooks says. It was a $200,000 deal for a packaging plant. The terms were very attractive and he had the help of an equipment finance veteran who mentored him through it. When it worked out, he knew he had something very big in his arsenal and he’s been offering it ever since to anyone that qualifies for it.
“I said to myself anybody that needs equipment, this is a no brainer right here,” Brooks recalls of it. Now Brooks says when there is competition, he’s almost always the only one asking questions about equipment and the only one prepared to actually move forward with a deal tied to it. Of that experience, Brooks says he’s realized that some brokers have become so accustomed to the mindset of telling customers to take a specific deal, that they don’t stop to consider what they actually want. So his approach is to go in and diagnose what it is they’re trying to do first and then advise them of their options accordingly. And that’s what he does day after day.
At Broker Battle 2025, it was very much like time spent in the office. He was expected to be his normal self, but on stage in front of a large audience, while three judges played the role of prospective client and asked him questions about what they should do. The end result of it all was that Mike Brooks, former fighter in the ring, walked away as the Broker Battle champion in the equipment finance category in 2025.
“It felt amazing to be able to showcase what I do on a daily basis,” Brooks says, making it a point to say that even the venue took note of his win and offered him a personal congratulations on social media.
In the final photo-op on stage with his prize check, Brooks was the epitome of his dual life—the suit and tie spoke of business, while the cigar and sunglasses hinted at his former life in the ring. “I was a crowd pleaser,” he jokes. “You want to be like ‘bam bam bam’ and the crowd to be like ‘AHHHH!!!’ I want them to do that. I had a great time at deBanked.”
Ryan Showe on Winning This Year’s Broker Battle
March 3, 2025
“What being a broker means to me is servicing your clients in the best way possible, really putting their needs before anyone else’s,” says Ryan Showe, VP of Sales at Long Island-based Lexington Capital Holdings. “Ultimately, at the end of the day, we don’t have a job if our clients aren’t happy, so just constantly doing the right thing, putting your best foot forward, and making sure that you’re doing everything ethically and honest.”
Showe was the winner of the 2025 Broker Battle at deBanked CONNECT Miami for the revenue-based financing category, earning him the recognition of Top Broker and the recipient of some prizes along with it. Showe has been in the business for just a little over three years, starting at Lexington during its beginnings. Back then, learning the ropes while doing the work meant putting in 70-80 hour weeks on a regular basis. That included not only seeking out advice from the experts but also watching videos and reading books to fully immerse himself in the mindset of what it would take to become successful.
That effort is paying off and today Showe specializes in the most delicate part of the process at Lexington, helping clients who have applied get to the finish line with a deal while managing lender-side negotiations and communications. On the latter side, that means being highly familiar with the guidelines of more than 60 financial service companies at any given time.
“Anybody can get someone to apply and just fill out a quick one-page application, send over a couple bank statements, but really selling the deal, there’s a specific art to it,” says Showe. “It’s really important to be an expert in your industry and know all the lender guidelines, know what the backend process looks like, because every lender is going to have a different process, whether there’s certain steps that some lenders want, whether it’s a manual-login or DecisionLogic. There’s so many ins and outs to every different lender. And just being able to know all that off the top of your head and just really sound like an expert.”
At Lexington, one of the recent educational team-building strategies was to host an internal Broker Battle in which 30 employees participated in a double-elimination competition. The company’s CEO, Frankie DiAntonio, devised the format and questions—not only role‑playing scenarios but also testing general industry knowledge with trivia. Showe says it’s good practice to be put on the spot in front of a crowd, because a key part of sales is thinking on your feet and executing when it counts. Doing it together with colleagues made for a fun experience in a company that prides itself on a family‑like atmosphere, while also mirroring the competitive nature of the industry where many brokers vie to serve the same customers. It’s game time all the time.
“I even tell my clients, ‘competition is always going to breed the best results,'” Showe says. “If you want the best of the best, you have to make people compete. And it goes down to even selling a deal, right? So if I have a deal and another company has a deal, compare my numbers against their numbers. I’m going to do anything I can to win that business.”
By happenstance, Lexington’s Corey Digiantomasso was one of the six finalists selected to compete in deBanked’s inaugural Broker Battle in 2024, where he put up a very impressive performance. This year was Showe’s turn where contestants weren’t given much background on the format other than that it would be roleplay-based. Showe kind of liked the mysteriousness of it.
“I’m best at showing up and just getting the job done,” Showe says. “So just doing what I do every single day made it easier for me at least.”
On his victory, Showe described the feeling as awesome while also recognizing that his opponent in the Battle, Joe Sasson, was a very worthy competitor. A large crowed showed up to support both of them during the championship.
“It was great to just see all the hard work that I’ve been putting in over the last three years pay off and be crowned #1 in the industry. It goes a long way for not only myself, but for the company as well.”
Broker Battle 2025 Champions
February 24, 2025Broker Battle 2025 took place at the Fontainebleau on February 20th during deBanked CONNECT MIAMI. Video highlights and more will be available soon. In the meantime, here are the results and the top brokers:
Revenue Based Financing
Top Broker: Ryan Showe, Lexington Capital Holdings
Runner-up: Joe Sasson, Advance Funds Network
Equipment Financing
Top Broker: Mike Brooks, Best Connect Capital
Runner-up: Yaro Yarema, Capital MBS
Two Broker Battle Judges Starred in This Show
January 31, 2025
Josh Feinberg and Will Murphy, both judges for the equipment finance category at the upcoming Broker Battle at deBanked CONNECT MIAMI, previously starred in the sales reality show Equipping the Dream. The six-episode show series debuted in February 2022 where they helped train new reps at their equipment finance brokerage Everlasting Capital in New Hampshire and awarded the best of the group. The unscripted series is the most watched show in history of its kind. All the episodes are here.
Any broker or sales rep that is knowledgeable about equipment financing can enter to compete in the short Broker Battle competition on February 20th at the Fontainebleau by submitting their name here and registering for the event here. The prize is $3,000, a trophy, the title of top broker, and the opportunity to be interviewed for a feature story. The two other categories, revenue based financing and SBA lending, also offer the same prizes and can be entered into using the same links.
Compete to Be The Top Broker in Person and Win Cash, Trophy, and the Title
January 23, 2025
If you sell revenue based financing, SBA lending, or equipment financing, deBanked MIAMI invites YOU to compete in Broker Battle 2 in Miami Beach at the Fontainebleau on February 20th. It’s simple, just register to enter it here if you’re already attending the event, and be judged in a short qualifying round in person during deBanked MIAMI. The two highest scored contenders for each of the 3 aforementioned categories will compete on stage at the conclusion of the event for a short championship.
THE WINNER OF EACH CATEGORY GETS:
- $3,000
- TROPHY
- TITLE OF BEING TOP BROKER
- INTERVIEW WITH DEBANKED (AT YOUR DISCRETION)
This year, Anthony Truglia, the winner of Broker Battle 1, will return as an MC! The judges are a mix of previous participants and industry veterans who are ready to make the competition one you won’t want to miss participating in. All attendees of deBanked MIAMI will get to watch the battle as part of the day’s normal course of activity. See the photos from last year’s inaugural battle here or watch the full video to see what it was all about below!
BROKER FAIR IS BACK! – NYC
May 2, 2022
Broker Fair is coming back to New York City on October 24th at the New York Marriott Marquis in Times Square. Anticipated to be the biggest Broker Fair ever, brokers from the small business lending, commercial financing, revenue-based financing, leasing, factoring, and MCA industries, will come together in the heart of New York.
“It’s amazing to have participated in the industry’s growth over the last four years,” said Broker Fair founder Sean Murray. “Our first event launched in Brooklyn in 2018 and now the demand has brought us into a massive newly-renovated venue in the middle of Times Square.”
Brokers, lenders, funders, factors, equipment financiers, fintechs, and the whole small business finance ecosystem can expect a full day of education, inspiration, and high quality networking opportunities.
Register here. For inquiries or questions, email events@debanked.com.
See last year’s sizzle reel:
