Jeffery is CEO and the “Chief Ideator” behind Hardboot Inc., a custom software development company that delivers end-to-end digital solutions and project management to over 30 clients. Since inception in 2007, Jeffery has grown his team to more than 40 people globally with offices in Toronto, New York, Philippines, and Pakistan.

We interviewed on the 9 year anniversary of Hardboot Inc. October 27, 2016 and it gave Jeffery the perfect trigger for stories of his past and how he’s come to where he is now. Ups & downs and even a few people he admired who seemed to reject him, pushed him to grow.

Without a doubt, Jeffery talks pretty quick but his stories have value! He talks about the value in learning how to work with others well “helping them get their wins”, how he fell into sales even as an introvert and now it’s the business piece that drives him the most, the impact of a lit teacher who was reading up on Linux and offered him a teaching gig, and how he got over his stage fright and lack of speaker skills that would literally keep him up at night.

Have you ever been judged unfairly by someone and had it become a huge motivator for you?

Jeffery tells us about key stories from his largely entrepreneurial career:
* His first boss who told him he had to get out there (leave his job and do MORE)
* Another potential boss who in the interview told him that he mitigates risk too much, and has a need to always rely on others, but then this person later contracted his services and of course, apologized for misjudging him
* How he eventually became the guinea pig of his own business model, taking over the digital department lead and forming HardBoot Inc.

Listen in as Jeffery shares insights in how he finally became comfortable with the title CEO, and realized it was time to start applying it. The value and importance of titles (or not) became clear to him when he was mistaken by a colleague for being “an MBA”.

To learn more about Jeffery and connect with him around his Silver Lining Story please visit or email him / connect with him on LinkedIn using

Debbie Horovitch

Debbie Horovitch is the creator & publisher of the bestselling series The Silver Linings Storybook,an anthology book of personal stories from business leaders. Interviews are published in articles and radio shows.