MacDonald is currently in custody, as reported by prosecutors. He is the founder of a programming services firm named Oshen, alongside information gathered by the FBI regarding his activities.
According to federal investigators, McDonald’s alleged harassment started following a deteriorating business relationship with one of his investors, who is associated with a prominent venture capital firm in Boston, during 2024.
The investors, who had contributed over $250,000 to a startup called Waev in 2022, expressed growing concerns by March 2024, believing the business might be fraudulent due to McDonald’s lack of transparency about the company’s finances.
Officials indicated that one investor became suspicious that McDonald was operating a “virtual currency scheme,” diverting investor funds into secretive deals. He even warned another potential investor against putting in money, which, understandably, upset McDonald.
The same investor also alerted others about his worries, advising them to cut their ties, which they did shortly thereafter.
Additionally, prosecutors mentioned that McDonald is thought to have harassed two other investors who had purchased a house in Winchester to establish a venture studio. The FBI noted that McDonald was evicted from the property around March 2024 as these investors withdrew their capital.
According to reports, FTX Ventures—tied to Sam Bankman-Fried’s cryptocurrency company—was another significant backer of Waev. This connection brings to mind several issues regarding the misuse of investments.
The building meant to serve as McDonald’s Venture Studio was a high-rise valued at around $2.5 million.
Post-eviction, the homeowner claimed to have inflicted approximately $1.3 million in damage to the house, which included breaking various fixtures.
In July 2025, McDonald faced charges in Woburn District Court for breaking into a home and causing over $1,200 in damage, which ironically included punching walls and sending images of the destruction to three investors. Activities related to this case are reportedly on hold.
After distancing themselves from McDonald, the investors reported receiving a barrage of harassing emails from him daily, which continued for several years.
Over time, the tone of these messages escalated from mere provocations to outright threats, particularly noted around April. One email contained alarming threats about violence if an agreement regarding a property was not reached. Following this, one investor sought a non-harassment order against McDonald.
This investor, who had initially raised concerns, ended up hiring security and installing cameras around his residence due to the nature of McDonald’s threats.
It seems that after McDonald was informed of the restraining order, he began to include this investor in his menacing communications as well.
Reports suggest this partner struggled with heightened anxiety to the point of keeping his children indoors and removing business signage to avoid recognition, describing a life lived in fear. There were even unsettling emails where McDonald edited a picture of the partner accompanied by an alarming message.
McDonald also seemed to want to shift blame for his eviction in Winchester, and his emails indicated a pattern of violent threats, declaring, “If I don’t go home, one of you is going to get shot.”
Other investors voiced concerns that this partner was nearing a breakdown due to the stress of the situation.
One of the investors who owned the Winchester mansion had intended to sell it to McDonald in exchange for a stake in Waev, only to later obtain a restraining order after McDonald reportedly broke into his property in July 2025.
This investor relayed to the FBI that McDonald’s persistent threats against him and his child led to significant emotional strain.
Additionally, another investor recounted relentless mockery from McDonald regarding a personal tragedy involving the death of his adult child.
In May, McDonald reportedly bombarded the group with threatening emails, derogatorily labelling them as “boomers.”
Fearmongering continued, with messages filled with violent imagery and threats about personal harm sprinkled throughout.
McDonald was arrested on May 6 by Cambridge Transit Police after allegedly threatening a person with a knife.
Continuing threats from him were documented through June and July, leading to multiple pending cases in various courts related to harassment and intimidation.
Finally, he was apprehended on Tuesday after not appearing in court for a prior assault case. As of now, an attorney representing McDonald has not responded to inquiries regarding the situation.
