When it came to an agent - who's only 2 years his elder - Gardland wanted someone reliable. He needed an agent who cared enough to simply answer his phone calls whenever he needed to chat.
"To be real, I'm not a big-time prospect right now," Garland said.
"I wanted someone that I can call and who'll pick up the phone or have something for me. I wanted someone who cared for all their players equally, someone who isn't very high-profile and was willing to do what I'm trying to do: work from the bottom to the top."
And Berkowitz brought his "A" game from the beginning. He left his commercial transactions final exam in Durham, N.C., to fly north to the Portsmouth Invitational in Virginia to pitch his client to NBA scouts.
Berkowitz has helped Garland inch closer to an endorsement deal with Under Armour; connected him with Kendrick Williams, a trainer who works out elite combo guards; and is attempting to make arrangements for him overseas if the NBA draft process doesn't work out.
But with little experience with professional basketball between the two, they are learning as they close in on their goal: to get the 6-1 Garland to play basketball at the highest level.
"What he has to overcome is his size and range and I have to overcome my age," Berkowitz said. "We are going to market ourselves to NBA teams.
"Even if he spends a year in Europe, our goal is ultimately signing that NBA contract. We are just two hustlers who are fighting to get into the league. Together."
In Garland's first season with the Explorers, it was his postseason dominance that drove La Salle to its first Sweet 16 in decades. Garland averaged 13 points and 1.2 steals per contest.
There were holes in his game, but Garland was determined to improve in hopes of making the jump to the NBA after his senior season. Following an early exit in the Atlantic 10 Tournament, Garland was left without any opportunity to impress in a postseason tourney.
However, he finished his senior year strong by ending it with what originally brought him to college - a degree, in sociology.
"I was really focused on graduating school and locking down my grades for graduation," Garland said. "I was focused on the next step, but I had to graduate school. That degree is very big to me. I told my mom I was going to graduate college and I just wanted to put that smile on her face."
Now, Garland has a legitimate opportunity to play professionally overseas, and work toward his real goal of getting to the NBA.
For Berkowitz, who balances working on law papers and European professional basketball contracts in Duke's library, his bond with Garland will continue to grow. Berkowitz said it's about creating family, and his relationships with clients go beyond contractual obligations.
"He can utilize a year overseas," Berkowitz said. "In the same way that many players go through the predraft process, similar things happen with a first year in Europe with high-level competition being examined by each team's European scouts. How he rebounds from a year of struggling and how he adapts will be a tell-all sign for teams, and they'll see [him] as a professional."
On Twitter: @TylerRickyTynes