Sean Murray is the President and Chief Editor of deBanked and the founder of the Broker Fair Conference. Connect with me on LinkedIn or follow me on twitter. You can view all future deBanked events here.
Articles by Sean Murray
How AI is Scaling a Veteran Small Business Financing Brokerage to New Heights
March 19, 2025
“There are [AI] voice systems out there that have just blown me away,” said Cheryl Tibbs, owner of Atlanta-based Commercial Capital Connect. “So we are using those and I’m implementing some in my office in my day to day—we have an AI receptionist that answers the phone, it just frees up time.”
As a broker, Tibbs recognizes the value of being able to answer a potential client anytime, anywhere, but there needs to be time to sleep, train others, and expand as well. And thanks to the advent of actual AI, it’s now become increasingly possible to scale on multiple fronts where it wasn’t before. Tibbs told deBanked that she’s been using AI to duplicate herself across anything she can.
“So we train these models on everything about our business, everything about us, and it can just answer questions, either through chat or having a conversation,” she said.
AI can call leads or qualify a customer through online chat at three in the morning if need be—not theoretically; it’s doing it for her already.
“Some mornings I wake up, I see full conversations between the conversational AI and somebody that filled out a lead form,” she said. “The chat agent has the ability to send them a text message with our full application link, or book them on our calendar.”
But more customers coming in the door means more questions from her team about where to place a deal. She’s got a solution for that, a bot she created named BrokerBuddy that can answer on her behalf when she’s not available to do it herself.
“I trained it on most of the lender guidelines that we work with, so they can just go in and just type a question, you know, ‘hey, BrokerBuddy, I’ve got a customer with a 680 FICO score.’ He says, ‘two years time in business, looking to buy a $40,000 skid steer. What else should I ask him? Which lender in our organization do you think will do this deal?'”
There’s a role for AI to just skip the questions and place a deal all by itself using advanced algorithms, something many tech companies tout these days, but the human nuance is a key component to her service, since any deal could be equipment financing, SBA, or working capital rather than solely one thing. It’s not always immediately obvious which one it’s going to be or what the customer would prefer. Way back in the day, Tibbs started purely with MCAs, back when they could only be done via a credit card machine. Since then she added equipment financing, working capital loans, and SBAs. For a long time now, she’s offered it all. She pairs up customers with the best fit and relies on her knowledge and relationships to know what’s going to work and what’s not.
“SBA is a hot button right now and merchants are really excited to know that this is definitely a possibility,” Tibbs said.
One opportunity with SBAs in particular is to consolidate MCAs, which, if the business owners qualify, can have a tremendous impact. Sometimes these business owners find her by seeing her posts online, and they reach out. Maybe it’s her they’ll get right away, or maybe it’s her AI. In any case, all of her experience has long since led other brokers to refer their own business to her, since she has a reputation for being able to get the deals done.
“I’ve been operating as a super broker most of the 20 to 25 years that I’ve been in this alternative space,” she said, “and as a super broker, I’m able to offer my broker partners more stuff than they even thought about. […] I study this stuff. I eat, live, and breathe it.”
While it’s unclear if AI qualifies as alive, her band of automated agents are beginning to breathe the rush of it all right alongside her. So many brokers (and lenders) are diversifying their product sets that her referral business is escalating, and she wouldn’t be able to scale without the assistance.
“Even though we get appointments, if we’re not on the phone with that merchant usually within three to five minutes, sometimes it’s hard to get them back on the phone. And even if they make an appointment, they may not show up. Having that instant engagement it definitely helps.”
Talk to People, Ask Questions, and Deals Are Everywhere
March 17, 2025
“Well, when everybody says it’s tough, that’s when I start smiling, because I’m going to sit there and collect them all,” said Adam Oster, Director of Canyongate Financial. Oster was talking about financing deals for trucks in a tough market, though he’s known to be able to handle any kind of equipment in any kind of market. Part of the joy he gets from the challenge of the job is rooted in just how many great people he gets to speak with. Connecting, helping, and building relationships are his passions. And it never stops for him.
“I like to jump in and do everything. I have to have direction so I got to be talking to somebody,” Oster said.
True to form, when he’s taking a break from talking about semis, box trucks, and medical equipment, he’s marketing 3″ filled bones, beef cheek rolls, and gourmet treats for dogs.
“My fiancée has a dog food company, so Thursday, Friday, Saturday, Sunday, we’re out slinging dog food, we’re promoting her business,” said Oster. That business is called Abby’s Barkery, and he’s proudly featured on the company’s main Shopify page. Sometimes the two worlds overlap—in that he could be processing payments for treats while placing an equipment deal at the same time.
“…by 7:30 you get home and you’re like, ‘I think just every day is Monday.’ That’s how I’m going to look at it. Every day is just Monday in my life,” he said jokingly.
Oster began his career in mortgages, followed by a stint as the owner of a supplements store. He launched Canyongate right in the early days of the COVID pandemic after a colleague said he’d be really good in the field.
“When we came on we were strictly working capital, and working capital has its peaks and valleys, so I needed to fill the gap when working capital was down,” Oster said. “I’m like, ‘Hey, let’s transition here.’ So we started onboarding.”
Onboarding with equipment financing providers is precisely what he did. It helped that some of those providers were located right in his own neighborhood, which shortened the learning curve and helped lead to some great relationships. These days, Canyongate’s business is now 70% equipment financing and 30% working capital. Like others deBanked has spoken to, not everyone who makes deals in equipment financing starts off by knowing everything about equipment.
“I knew enough in transportation, semis, trailers, that we lean there. But then I found very quickly that you got medical equipment—everything is a piece of equipment, essentially. So if I get a lot of invoices and I don’t know what they are, I have to Google it. I’ve got to look because the broker doesn’t tell you what it is. So I’m looking it up. I’m like, ‘Okay, this is a CNC machine… or this is a piece of yellow iron.'”
By now he knows so many things so well that he helps other brokers learn the ropes. As part of that he does coaching and training for large groups of people looking to break in. For example, they recently conducted an orientation for 500 people, where they started off by teaching them to focus on a niche. That could be semis or trailers or something else to get in the game. The deals themselves can come from anywhere, including simply knowing someone at the local gas station who might know someone who, in turn, knows another person—turning into a referral. It’s all about building relationships and asking the right questions.
“At the end of the day, it’s just conversation, ‘what are you trying to buy?’ And they’ll tell you. If I don’t know what that equipment is, I’ll say ‘what do you use that equipment for?’ They’ll tell you.”
For brokers already offering products like MCAs, they’re already on the call to steer the conversation in that direction if they so choose, but it’s important to do it thoroughly since the process to get a deal done is a bit more stringent.
“Ask if they need a truck, ask them what they need to finance,” Oster said. “When you’re submitting an equipment finance deal, it’s not an app and banks with no write up. You’ve got to tell me about the customer. Tell me about their experience. How are they going to use this equipment? There’s a lot of detail that goes into the deal before you even submit for underwriting.”
To that end, he said it’s important to set expectations for brokers looking to do equipment finance deals because it isn’t exactly the same even though it’s similar. On one hand if a broker can already sell a daily or weekly payment working capital deal then surely they’d be able to sell a monthly payment equipment financing deal. It’s a no-brainer when it comes to being able to offer the terms.
“Don’t fear it, ask the right questions,” he insists about taking the leap. And be prepared to ask them anytime anywhere. For example, he’s funded five MCA deals just through relationships he’s made through the Barkery.
“That’s a true story,” he said. “And I have pulled probably six or seven equipment deals out of the last year and a half from working at [my fiancée’s] business. So again, it goes back to it’s just conversation. Look at people’s needs. People tell me, ‘Well, I want to update my little shop and do all these things, I just don’t have the money.’ Well, what do you need? ‘Well, I need shelving, I need this…’ ”
Then he offers to help. Suddenly it’s the perpetual Monday all over again where he’s placing the customer while simultaneously processing payment for a good pup to chew on a lamb foot or a mammoth bone.
“And that’s how deals come about. Opportunity is everywhere. I love it. I get excited, man. I get all hyped up about this.”
Brokers: Making the Leap from Working Capital into Equipment Financing
March 13, 2025
“We can finance anything that doesn’t shoot, fly or float,” says Josh Feinberg, CEO of Everlasting Capital. “So no planes, no boats, no guns.” But any other type of equipment and he’s ready to chat. As a seasoned veteran of the equipment finance industry, that conversational starting point of knowing what to ask and how to answer takes a lot of practice to develop.
“Roleplaying is like stretching before going for a run,” said Feinberg. “It makes it possible for you to be fast on your feet and really be able to have the answers.”
Everlasting Capital is a broker shop based in Rochester, NH that believes strongly in practicing calls with colleagues to develop their skills. It’s a role play. Many shops do it. But becoming seasoned at it for one product doesn’t mean that a broker automatically becomes an expert at any type of call.
“A lot of [working capital] brokers think that they’re the ones that are trying to figure out if the business owner qualifies, but to be honest with you, in the equipment space, it’s vice-versa,” Feinberg said. “The customer is actually trying to qualify you to see if you are apt to be able to finance their equipment.”
Equipment financing flips the stakes and the direction, and with that a fresh need for practice toward managing it successfully. And that’s where some brokers used to other products get stuck, because their confidence drops in being able to navigate something they don’t fully know. To that point, it can feel intimidating to discuss machinery they’re not familiar with or trucks they’ve never driven.
Feinberg believes that anyone can learn this, however, simply by talking to business owners about these things. One doesn’t need to actually spend 20 years in construction to finance equipment in that industry, for example, though it certainly wouldn’t hurt. Feinberg’s own start in the business is very simple to replicate.
“I just started talking to business owners, figuring out what they want. A lot of times [in the very beginning] I didn’t even know what the equipment did. I would have to Google it while I was on the phone with them.”
That, of course, has changed with experience. Now he and his firm have become so well acquainted with certain industries that they’ve integrated themselves within them. The dump truck market, for example, has become one of their core areas of expertise.
Despite this attainable path to success, some brokers throw up their hands and assume the process will be too hard or the financial incentive too low to even try equipment financing—even though that is generally not the case. In an era where working capital has become so competitive, it should be considered as an additional offering to maximize value at the bare minimum.
“[When] you have the one person calling like, ‘hey we have monthly payments that are single digit rates, and we can do monthly payments one to five years.’ It’s really easy to spark up a conversation and be able to ask the questions that you need to do, and then get answers back,” he said.
Advocating for other brokers to adopt his approach might seem like it would increase competition, but Feinberg explained that the market is wide open with opportunities. Moreover, he feels strongly about matching business owners with the right solution. To that end, he is also the co-founder of Equipment Broker School, a system designed for anyone needing a jump start or a refresher on the art of equipment financing. His company previously starred in an online reality show where new salespeople were trained in person in the office, and Feinberg himself recently appeared as a judge at deBanked CONNECT’s Broker Battle in Miami Beach this past February. The event was a roleplaying competition that evaluated brokers on their ability to diagnose needs and propose solutions. It was like just another day in the office for him.
“It made me really excited to be able to be a part of the Broker Battle, just as a lot of people know, and you know especially just for myself, being able to train people on how to be able to promote, how to be able to work, and how to be able to just partake in equipment financing,” Feinberg said. “It has been a super big passion of mine, especially just within the deBanked community as a whole.”
We Used AI to Make a Loan Broker Video Game
March 13, 2025As AI continues to progress beyond LLMs into doing just about anything one wants, I took the liberty of having it create a very simple javascript-based online game (for Desktop browsers only) to see what would happen. With about 5 minutes worth of work, it created something functional that it calls Loan Sales Office v1.0. The game gives the user the option to earn points either by answering a customer objection correctly or by moving the character around the office and racing against the NPC competitors to collect signed contracts. First one to 50 wins. It created the questions and answers itself.
The purpose of the exercise is to bring further awareness to AI.
If you are on a desktop browser, click below to try the game.
HOW TO PLAY
Compete against two other sales reps. First one to 50 deals wins.
Move your character with the keyboard arrows or the on-screen controls.
Collecting a signed contract = 5 deals
Answering a question right = 1 deal
The good leads are elusive. Signed contracts spawn at random.
Must use desktop browser. Good luck!
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.”
Jack Dorsey is Satoshi Nakamoto?
February 25, 2025If you’ve seen the analysis that connects Jack Dorsey to Satoshi Nakamoto floating around the web, that was researched by yours truly. I first proposed the possibility on February 24, 2024 and have since discovered a lot of compelling evidence to really support it. Here is a link to the recent tweet that went viral on the matter and a mirror of that tweet with source links. This is hardly all that I have. I did tag Dorsey so that he could see it but he did not reply to it or directly weigh in.
I have been following Dorsey’s company Square for deBanked since 2011.
In early 2024, a legal trial commenced on the matter of Satoshi Nakamoto’s identity (Crypto Open Patent Alliance v Craig Steven Wright) for which Dorsey played a key role to prove that an individual named Craig Wright was NOT Satoshi. Wright had been claiming such for some time.
As part of the trial, a large trove of new emails and testimony surrounding Bitcoin’s founding were disclosed, including many emails written by Satoshi himself (Emails with Martti Malmi / Emails with Nicholas Bohm). Before the judge made a ruling on the outcome, Dorsey made interesting remarks in Block’s Q1 2024 earnings announcement on May 2, 2024. He mentioned Satoshi the person as the basis for the company’s crypto strategy. While skeptics have chalked this up to simple fandom or ideology, it was wholly unnecessary to reference Satoshi the person and potentially risky if he doesn’t know Satoshi’s true identity. Coinbase, for example, lists “the identification of Satoshi Nakamoto, the pseudonymous person or persons who developed Bitcoin, or the transfer of Satoshi’s Bitcoins” as a risk factor to revenue. Block makes no such disclosure despite nearly half of the company’s revenue being derived from Bitcoin sales.
From Dorsey’s Block shareholder letter on May 2, 2024:
These statements could have been made without referencing Satoshi by name, especially in an era where longtime Bitcoin advocates have sought to minimize the influence of Satoshi the individual today. However, these statements would be very fitting if the CEO was speaking about himself.
Block has also self-published a book titled My First Bitcoin and the Legend of Satoshi Nakamoto which glorifies Satoshi and concludes by stating that “Satoshi’s vision is having an impact all around the world.” Hard copy print versions of the book were also made and distributed. deBanked obtained a copy.
That viral post again with source links can be found here. I am not an investor in bitcoin or Block. My experience with Bitcoin over the past 10+ years is as a payments mechanism, namely as peer-to-peer cash.
My email is sean@debanked.com
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
