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The journey and legal technology to lawyers better

Two lawyers are building a platform to save you 1000s of hours (and headaches)
The journey and legal technology to lawyers better

Join Peter, Natalie, and special guest co-host Laura van Wyngaarden as they speak with Rebecca Kacaba and Mat Goldstein from DealMaker about their journey to create a new way for companies and investors to streamline the capital-raising process. Rebecca and Mat share their insights into how implementing workflows, thinking outside the box, and collaboration with experts outside the legal industry can help you build a better product. 

Rebecca Kacaba


Rebecca Kacaba, DealMaker

Rebecca is the Chief Executive Officer and Co-Founder of DealMaker, winner of Lexpert's top 40 under 40 and named one of North America's most innovative lawyers by the Financial Times. She practiced law on Bay Street for over 10 years, founded the startup practice group at one law firm and was co-chair of the Toronto Venture Technology and Emerging Growth Companies Group at another. She regularly acts as an advisor to startups in corporate structuring and other matters.

Mat Goldstein


Mat Goldstein, DealMaker

Mat practiced law in New York City before returning to Bay Street. With past startup business experience Mat has been providing his growth company clients with guidance on strategy, operations, team-building and corporate development. His skill set and cross-border expertise continue to supercharge DealMaker's growth strategy. 

Peter Aprile


Peter Aprile, Counter Tax Lawyers

Peter Aprile is a senior lawyer specializing in tax dispute resolution and litigation. His vision as Counter’s founder and his everyday role at the firm are one and the same: to be an agent of change, uncovering opportunities and developing strategies that achieve more than anyone expected. A creative thinker, Peter studies problems from all different angles to find what others have missed. He’s also convinced that he likes winning more than most people.

Different people describe Peter in different ways. At the CRA and the federal Department of Justice, the word relentless comes up quite a lot. Admittedly, so does the word a**hole – but it’s often said with a certain grudging respect, if not affection. Peter’s clients call him a saint. Well, some of them, anyway. His colleagues describe him as empowering and harddriving, but fair. Peter’s friends call him loyal. His wife describes him as a lot to deal with, but worth it. Peter encourages his young daughter and son to call him “The Big Homie,” though with limited success. His mother describes him with the single word mischievous – before going on to complain that he should call more.

Read Peter’s complete bio →

Natalie Worsfold


Natalie Worsfold, Counter Tax Lawyers

Natalie is a tax lawyer who represents individual taxpayers and owner-managed businesses in disputes with the Canada Revenue Agency (CRA). She also successfully challenges CRA decisions denying taxpayer relief and helps facilitate applications under the Voluntary Disclosures Program.

But what you really need to know about Natalie is that she’s a tax litigator with heart. When she takes a case, it’s not out of technical interest – it’s because she cares. And if she believes the government has got something wrong, she won’t stop until it’s been put right. She’s fierce.

Natalie is the co-architect behind many of Counter’s process workflows, software and data analytics systems, as well as our comprehensive knowledgebase (loving named Hank). And when it comes to preparing cases, she’s Counter’s secret weapon – happiest when elbow-deep in evidence, meticulously building creative solutions to seemingly impossible problems. Because the fact is Natalie sees things that other people don’t.

Natalie’s family and friends describe her as loyal, selfless, understanding and fun. They also mention stubborn. To her Counter colleagues she’s a combination of stellar brainpower and contagious enthusiasm who elevates the game of everyone around her.

Read Natalie’s complete bio →

Laura van Wyngaarden

Guest Host

Laura van Wyngaarden, Diligen

Point of View

You are building NewLaw.

Are you working to build a great NewLaw firm? An exciting legal tech company? Or, a product set to transform the legal industry?

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