BUSINESS DEVELOPMENT

My Business Journey

Twenty-five years building one of Canada’s leading SaaS companies, from an idea in a pub to half a million customers.

Over 25 years, I helped build one of Canada’s leading SaaS companies, and we grew every single year along the way. LegalWills started as an idea over a drink in a pub. It evolved into a service that has helped more than half a million people prepare their legal documents, and culminated in a partnership with Costco, one of the world’s most recognized and respected brands.

In 2026, I retired as CEO of LegalWills and handed the company over to a new management team. I remain a co-owner and Director.

Tim Hewson and Henry Raud
Writing a will on LegalWills.ca

ABOUT

LegalWills

My business partner, Henry Raud, and I created LegalWills to allow people to create common legal documents in a very easy, convenient, private, secure and cost-effective manner, without the need to pay the high expenses of a lawyer. Since starting in 2001, we have helped around half a million people prepare their estate planning documents in Canada, the United States, the United Kingdom, and South Africa.

MEDIA

Articles, Interviews, and Features

Tim Hewson on CTV Morning Live

08-01-2026

CTV News

The importance of updating your will.

Tim Hewson on Daytime Ottawa

11-18-2022

Daytime Ottawa

Take a look at the Daytime Ottawa segment on LegalWills.ca and “Make a Will Month.”

Insights and Straight Talk podcast

05-06-2025

Insights and Straight Talk

A podcast conversation on building and running a business.

INSIGHTS

Business Lessons & Trends

Articles and videos on what 25 years of building a business taught me, and the trends I’m watching now.

The first articles are on their way.