· What do you think is better: Being an Employee or Being Self Employed?

· What are the benefits of being an employee?

· What are the downsides of being an employee?

· What are the benefits of being self-employed?

· What are the downsides of being self-employed?

· Why does voting matter?

· How do you usually lean politically? Are you “Liberal” or “Conservative”?

· What are the most important issues in this election?

· How do Canadian Politics compare to American Politics?

· What’s the difference between being a “generalist” and being a “specialist”?

· Are most entrepreneurs “generalists” or “specialists”?

· Would you become a “specialist” in a field early in your career?

· What are the benefits of becoming a “specialist”?

· In between “reading” and “doing” – which one is more important?

· Why do people get caught up “reading” and avoid “doing”?

· What’s your favourite way to learn?

· Is READING important?

· What’s the difference between “structured” and “unstructured” thinking?

· What’s the difference between a “structured” and “unstructured” routine?

· Are entrepreneurs naturally unstructured thinkers?

· How do you develop an unstructured way of thinking? Is it something you’re born with?

· What are the implications of reopening the economy after COVID?

· What are your thoughts on a 4th wave and another lockdown?

· Which behaviors learned in COVID do you think will stay?

· What were some of your biggest takeaways from the lockdown?

· Why does it seem like the USA is more entrepreneurial than Canada?

· Is it a cultural difference?

· How could Canada become more entrepreneurial?

· What are some of the biggest career transitions you’ve made?

· When should you consider making a career transition?

· What advice would you give someone making a career transition?

· What is inflation?

· What does high inflation mean to the average person?

· Is higher inflation here to stay? What would be the consequences?

Today on The 5AM Grind, we’re delighted to bring you our guest interview with Tim Brady.

Tim Brady is the CEO of Colligo, a provider of email management and document management software that helps better integrate Microsoft 365, unlocking productivity and governance for organizations.

Tim started his career working in finance at RBC and Picton Mahoney (a prominent Toronto based hedge fund) after graduating university. After several years as an investor in the software and tech sector, Tim pursued the path of entrepreneurship, founding Olbia Software and acquiring Colligo in early 2020 to help propel the company into the next generation of SaaS for enterprise content management.

Tim’s story is a great example of how the path to become an entrepreneur can be varied. Instead of building a company from ground zero, Tim’s story demonstrates an alternative path to entrepreneurship, via acquisition. We hope you enjoy this interview!