In specialty finance, closing a deal is never just about the numbers. It’s about reading people, adapting to pressure and turning complexity into opportunity. This year’s Rainmakers prove that the real edge comes not from a pitch deck, but from persistence, partnership, and precision under fire.
“We all want to win together.”
For Alexandra S. Scoggin, Senior EVP at nFusion Capital, closing a $46 million facility that initially slipped through her fingers was a defining moment. “It was a roller coaster ride,” she recalls. “But it reinforced the value of persistence, strategy and speed in a competitive market.” Scoggin’s philosophy? Be more than a lender. “Clients know they can rely on me for strategic guidance, industry connections, and long-term support.”
“If it hasn’t been done before, that doesn’t mean it can’t be.”
Jeremy Baker, Managing Director at Wells Fargo Capital Finance, thrives where conventional structures fail. “My boss told me we couldn’t do that, it had never been done before,” Baker says of a $750 million ABL solution he helped close. “But I had already worked out all the potential pitfalls … Who cares if it hasn’t been done?”
“There’s something special here.”
David Estrakh of Express Trade Capital won over a skeptical CFO and helped a client grow into a Star Wars-licensed powerhouse. “The owner’s wife printed one of my longer emails and highlighted parts she thought exceptional,” Estrakh says. “She basically said, ‘This guy is clearly no banker; there’s something special here.’” For him, deals are about more than funding — they’re about intuition and connection.
“Deliver what I promise.”
In distressed finance, Heidi Lipton, Founding Partner at Rock Creek Advisors, knows that time is the enemy. “It’s never over until the wire hits the bank,” she says, recalling the successful sale of Kologik. “I don’t like to ‘talk the talk’, I like to deliver results, even in tough markets.”
“It’s impossible to fake authenticity.”
Blake Kenny, Managing Director at Great Rock Capital, believes that there is not a specific one size fits all strategy to building relationships: “We all generally want to work with others that are relatable, who genuinely care, have high integrity, a strong work ethic, and that don’t take themselves too seriously. I believe prospects, clients, and partners can see these qualities in our entire team, which makes for an easy working relationship. At the end of this journey, it is highly unlikely that anyone will talk about my title, notable deals, or any specific achievements. I do hope that they talk about a great relationship and the positive achievements accomplished together. Most reading this have a full appreciation that when in the trenches of an active transaction and working all hours of the day (sometimes seven days a week), it’s impossible to fake the above.”
“If you have to push too hard, it’s likely not the right fit.”
Andy Dillard, SVP at Porter Capital, emphasizes patience and listening. “Closing deals successfully isn’t about chasing,” he says. “It’s about positioning. If the value is clear and the structure makes sense, the deal will come together naturally.”
“Being prepared is everything.”
For Kyle C. Shonak of Gordon Brothers, experience from the back end of deals informs how he makes them now. “Time is not your friend; it will kill a deal,” he says, reflecting on a transaction with Big Lots. “No deal is a straight line … It’s all the experience on the back end that allows me to be more effective today.”
“Every stakeholder has a threshold.”
Anthony Pirraglia of Loeb & Loeb underscores the need for clarity and compromise. “Fairness is critical throughout the negotiation process,” he says. “When parties feel heard and treated fairly, they’re more likely to honor the agreement.”
“You either have it or you don’t.”
While many believe great dealmaking can be taught, Baker sees it differently. “In my opinion, you either have it in you or you don’t,” he says. “Being coachable and having an insatiable will to win are absolutely necessary traits.”
“Trust, but verify.”
Estrakh adds a cautionary note: “While I give real weight to good history and demonstrated character, I still tend to lean on the adage, ‘trust, but verify’.” His balance of warmth and vigilance is part of why his clients stay for years.
“Greatness is built on reps.”
Shonak compares the grind of dealmaking to elite training: “It’s comparable to an athlete’s or a doctor’s training … The more reps you complete, the more effective you become.”
“You get to play this game.”
Estrakh puts it all in perspective: “A deal is just a deal … don’t take it too seriously and have fun! Far enough into your career, you’re probably not trying to close a deal to put food on the table. Be grateful you get to play this game.”
Closing Thoughts
Specialty finance isn’t for the faint of heart. It’s a field where setbacks are routine and certainty is rare. But for these Rainmakers, the thrill is in the challenge — and the rewards come not just in dollars, but in trust earned and deals done right.