Consultant, Coach, and Comedian sounds like an odd combination until you meet Brian. The self-proclaimed ‘reluctant entrepreneur’ will tell you it’s the only thing that makes sense when you look at the career he’s had.

The self-proclaimed ‘reluctant entrepreneur’ has made a career out of adapting to whatever situation he finds himself and finding ways to thrive, not just survive.

After looking back over the past 30 years, those three roles are the only that make sense.

Brian started his career in user experience working at Apple on the notorious Newton Message Pad. The role placed him squarely between marketing and engineering where he saw firsthand the calamitous effects of poor communication between teams. When the Newton finally shipped – a year late – it went on to become famous for being Apple’s biggest failure. 

Working at Apple in the years that followed, was like getting an MBA in how NOT to run a technology company. So he left and pursued the nascent field of web design and development and leveraged those skills to break into his dream job with advertising. 

Ironically, living that dream for a year made him appreciate the tech business more and he returned to Apple. Only this time, he went into marketing bringing with him the pain of being one of their customers during the days of Gil Amelio, and a few other disastrous CEOs. 

Exactly one day after Brian returned, Apple bought NeXT Computers, and with it came Steve Jobs. Despite the two events being unrelated, they are still relevant to the rest of the story. 

Even though Steve Jobs’ second stint at Apple has been well-documented, Brian’s have not. The second time around, Brian ran marketing for the creative industry, before switching to technology manager of desktop line for the iMac, G3, and G4.

While working full-time at Apple he was approached by his friend Scott to do a startup, you know, like everyone else was doing in the late 90s. Scott’s idea to create a permanent, personal email account for a couple bucks a month sounded like a great idea if you did the math. A week into our venture, HotMail came out with the same idea, but with a twist. Free. 

Undeterred, they kept at it and eventually landed on the idea of scanning email attachments for viruses and removing them before people had a chance to open them. This idea, plus creating a host of email-centric services became the idea for a company originally called SafeStamp. One feature we thrown in almost as an afterthought was SPAM blocking. It occurred to them that blocking SPAM had little value if you didn’t know how well it was working. So they created a Quarantine feature to see blocked messages and let through the ones it shouldn’t, and changed the name of the company to Postini. That feature is known as the first commercially successful SPAM filter and turned out to be one of the biggest selling points and many patents that made the company attractive to Google, who bought it in 2007 for $670M. 

Full Bio

His journey began at the University of Illinois where he studied Art and Speech Communication at an institution mostly known for Engineering and Accounting. It was there that he discovered the sport of rugby and focused on his passion for live music. While his peers were pulling all-nighters studying differential equations and carried interest, he was busy developing the social and cognitive skills that are often overlooked and undervalued among the STEM disciplines.


It wasn’t until he was a subject in an experiment studying the effects of technology on communication, that  he realized the value of saying what everyone else was thinking. Confused by the objective of the study, Brian pointed out what he felt didn’t make sense. 

This led to Brian getting hired by the professor behind the experiment to help with his research. While transcribing hours upon hours of videos, he noticed something the research played out. People who were more skilled at using computers were being perceived as being more competent even in domains they had little knowledge. 

People who were more skilled at technology were often perceived as having more competence in a particular domain 

he saw an incredible opportunity created by poorly designed products. The research uncovered an interesting insight. 

The research lead to an insight. 

I’m trying to say this. I was a subject in an experiment. I spoke up and said what everyone else was thinking. It got me a job working for Nosh. It was there that I saw the incredible opportunity