Rebecca Kacaba

Co-founder & CEO, DealMaker

FintechTorontoOn TechTO stages since 2026

Rebecca Kacaba is co-founder and CEO of DealMaker, the Toronto platform that runs online capital raises end to end. She practised capital markets law for over a decade and left a partnership at the world's largest law firm to start the company with Mat Goldstein. She testified before the US House Financial Services Committee on capital access in February 2025.

On the TechTO stage ×1

BEST OF TECHTO11:09

She Left Bay Street to Build a $100M+ Capital Raising Platform | Rebecca Kacaba, DealMaker

Best of TechTO · April 2026

Watch on YouTube ↗

First seen on the TechTO stage in 2026. Every talk is searchable — ask the archive about Rebecca ↗

In their words

sometimes when you find a great co-founder, 1 + 1 = 5

Best of TechTO, Apr 2026 · watch at 03:32 ↗

capital always needs to be strategic for you guys, the founder — it has to be doing something to propel the business forward

Best of TechTO, Apr 2026 · watch at 04:56 ↗

everybody has a great plan until they get punched in the face

Best of TechTO, Apr 2026 · watch at 06:19 ↗

A few quotes can’t cover everything Rebecca said on the TechTO stage. 1,600+ talks are searchable.Ask about Rebecca ↗

More from TechTO ×6

Podcast

TechTO Firesides ft. Rebecca Kacaba of DealMakerTechTO Together · their episode

2023

Newsletter

$1.7B in 2023. $2.5B today. Here's what changed.The TechTO newsletter · mentions Rebecca

2026

Newsletter

July 17, 2023: The art of the dealThe TechTO newsletter · mentions Rebecca

2023

Newsletter

January 23, 2023: Test Your Product on Your ParentsThe TechTO newsletter · mentions Rebecca

2023

Newsletter

January 20, 2023: What We Can Learn from Waabi's Recent InvestmentThe TechTO newsletter · mentions Rebecca

2023

Newsletter

January 13, 2023: Learn from this companies surprising turnaroundThe TechTO newsletter · mentions Rebecca

2023

Around the web ×1

Podcast

Empowering Entrepreneurs through Technology with Rebecca KacabaCanadianSME Small Business Podcast

2024

Quick answers

What is DealMaker?

A Toronto company whose software runs online capital raises — subscription paperwork, investor eligibility, payments and investor records — founded by Kacaba and Mat Goldstein, both former capital-markets lawyers.

What was the data point that changed DealMaker's direction?

Kacaba told the Best of TechTO stage that founders logged into the platform 25 times per deal while lawyers logged in six. The company rebuilt around the founders.

What has she been recognised for?

Lexpert's Top 40 Under 40, one of the Financial Times' most innovative lawyers in North America, Canada's Top 100 Most Powerful Women in 2022, and Waterstone's Most Admired CEO for 2023.

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Maintained by TechTO · facts sourced and dated · last reviewed Aug 1, 2026