Although Montgomery started his career in real estate and artist promotion, in the early 1980s he became enamored by technology and personal computers, in particular with the Commodore Amiga.

During this time, Montgomery worked for Trip Hawkins at video game pioneer Electronic Arts as a product manager.

[3] When Electronic Arts decided to focus product development efforts on the Apple IIGS computer rather than the Amiga, Montgomery left and moved to Topeka, Kansas to help Jenison build NewTek.

[2] Montgomery brought fellow FAUG members Allen Hastings and Stuart Ferguson to NewTek to create Lightwave.

Lightwave was used to create animation and special effects for many television and feature films including Babylon 5, Star Trek, and Titanic.

After several months, the group founded Play Incorporated together with Amiga software leader Digital Creations and video hardware developer Progressive Image Technologies, and focused their efforts on the Microsoft Windows platform.

"[10] Play's next consumer-oriented product was Gizmos, a suite of utilities, games and multimedia software for Windows personal computers.

[15] Play folded following Montgomery's death, with many employees, including Kiki Stockhammer returning to NewTek, which by then had redirected its efforts also into the Windows platform.

[16] Montgomery's enthusiasm for technology and people helped both NewTek and Play develop a passionate customer base, including high-profile celebrity users.

Early users of the Video Toaster included Todd Rundgren, Herbie Hancock, Penn and Teller, U2 and Oingo Boingo.

[17] Montgomery's leadership and marketing skills helped NewTek and Play obtain major national press attention for its products, including feature stories on NBC Nightly News and an article in Rolling Stone Magazine.

[18] NewTek employees were often spotted roller blading, playing laser tag, video games and working long hours.