DealMaker: ‘TurboTax for Securities Law’

August 26, 2019

Rebecca Kacaba says her journey from capital markets lawyer to startup entrepreneur started with too many late nights reviewing documents.

Ms. Kacaba, who specialized in securities law for more than a decade, says getting all the required documents together to close a private placement deal was a cumbersome process.

Forms would be printed out and scanned multiple times as they were e-mailed between brokers and investors, and lawyers would often find errors or deficiencies, requiring them to be sent back, she says.

Ms. Kacaba says that when she began a practice focused on startups with colleague Mat Goldstein, they begin developing technology to simplify the paperwork.

“We used it in our practice and got it up to a point where it worked and it made sense and then we decided, okay, we either have to make the jump or stop putting money into this,” she says.

Ms. Kacaba and Mr. Goldstein made the jump, co-founding a company that now operates under the name DealMaker (legally registered as Novation Solutions Inc.) in Toronto. In the summer of 2018, DealMaker launched a cloud-based platform for private placements.

“Think of it like TurboTax for securities law,” says Ms. Kacaba, who is DealMaker’s chief executive (Mr. Goldstein is the company’s chief revenue officer). “You have complex forms that investors need to go through and what our software does is, basically, put them through a securities law-based question flow that directs them to the right exemptions.”

An investor can complete the necessary paperwork in under six minutes, she said, which means private placement deals can close faster. “We can do any kind of deal: debenture, fund formation, flow-through shares, common shares,” Ms. Kacaba says.

Issuers pay transaction fees based on the amount of money raised. Lawyers using the software can customize documents or draft their own.

While any kind of company can use the platform, Ms. Kacaba says the vast majority of issuers currently using DealMaker are in the cannabis sector.

“The cannabis industry is superactive these days,” she says.

Ms. Kacaba says DealMaker is working to develop predictive analytics around the data the company has so it knows when specific industries are slowing down or picking up. Brokers and lawyers would be the customers for that data, she says.

Issuers using the platform have raised money from investors in about 25 countries, Ms. Kacaba says, with 20 per cent of all investors based in the United States.

Between 15 and 20 transactions are being done on the DealMaker platform every month, Ms. Kacaba says, and the company, which currently employs 10 people, has processed deals totalling more than $80-million.

DealMaker, which is in the process of raising an investment round of its own, is aiming to launch a full U.S. expansion within the next 12 to 18 months, she says.

One of the companies using DealMaker to simplify the process of raising money from international investors is Vancouver-based ChemioCare Inc.

The company, which is developing a transdermal delivery system for cancer drugs, has “investors from all over the world,” says Cidnee Vaykovich, its director of operations, which made it complicated to ensure investors were filling out the right forms for the right exemptions in their jurisdiction.

“We’re a small company, so we don’t have a huge back office to manage subscription agreements and track each additional step in the process,” Ms. Vaykovich says.

DealMaker isn’t alone in the space. Many brokers and lawyers are using other technology products to simplify the process of sending and tracking documents.

Devon Cranson, president of Cranson Capital, a boutique investment-banking firm in Toronto, says brokers in Ontario are required to use customer relationship management (CRM) software to track communications with investors.

His firm uses Salesforce, a popular CRM system, that’s been customized “with a few other add-on apps that help us create prefilled documents for investors,” he said. The company also uses DocuSign, an electronic signature system.

Mr. Cranson says he’s looked at other systems, including DealMaker, to manage the paperwork involved in private placement deals, but has stuck with his “homemade solution.”

“Salesforce offers some additional features that the others cannot compete with and our feeling was that if we went to one of the others, we’d still need a separate CRM,” Mr. Cranson says.

However, he says the other systems he’s looked at are aimed more at issuers or brokers, rather than at lawyers. “Everyone’s got a little bit of a different way of tackling this,” he says.

Ms. Kacaba acknowledges there are competitors, but says they aren’t DealMaker’s biggest obstacle. “We say our biggest competitor is the old way of doing things.”

Sara Mattern, a lawyer at Boston-based Foley Hoag LLP who advises startups and renewable energy companies on financing deals, says that when she started practising six years ago, signatures would still come in by fax. Now, e-signatures are the norm.

Changes like that “facilitate deal flow,” she says. “I have seen an acceleration in the pace of deals and the expectations of clients that they can go quickly.”

Ms. Kacaba says she believes faster deals will lead to more deals being done, and that technology can also help issuers reach more investors.

“We closed one deal with over 400 investors,” Ms. Kacaba says. Of those investors, more than 100 – in multiple countries – had completed their paperwork within 24 hours, she says.

Featured in the Globe and Mail. Original Article Link can be found HERE

Monogram Case Study - DealMaker (Embed)

When VCs said no, Monogram turned to retail investors. That decision powered their rise from startup to publicly traded company—and even helped them raise an additional $13M privately after their Nasdaq debut.

Monogram at NASDAQ celebration

The Challenge: Raising Capital on Their Terms

The Challenge: Raising on Their Terms

Monogram Technologies was founded with a bold vision: to revolutionize orthopedic surgery with a robotic joint replacement system using custom 3D-printed joints. The market for this technology is massive—approximately $19.6 billion, with over 1 million knee replacements per year. But it's a capital-intensive, regulation-heavy space—and traditional VCs weren't biting.

Instead of compromising, co-founders Dr. Doug Unis and Ben Sexson went all-in on a different path: retail capital. Why?

  • Control and ownership: Not only were they able to raise the capital they needed to grow the business—they did it on their own terms.
  • Long-term asset: They wanted to build an army of true believers who wanted to see the company succeed and would continue to reinvest over the years.
  • A value-add network: Raising from retail allowed Monogram to amass a waiting list of thousands of patients eager to participate in future trials.
  • Aligned incentives: Their mission to improve patient outcomes and build a better future for those struggling with joint pain resonated with retail investors.

The Power of Retail: Monogram's Capital Journey

Start Date End Date Type Platform Amount Raised # Investors
3/13/193/31/20A+SeedInvest$14,588,6686,000
11/16/201/16/21A+StartEngine$2,965,5018,000
1/17/212/18/22A+StartEngine$23,647,85314,082
7/15/223/16/23CFDealMaker$4,673,0002,249
3/1/234/8/23A+Republic$232,275120
3/1/235/23/23A+DealMaker$15,958,3645,198
5/18/23-Nasdaq listing
7/2410/24Unit OfferingDealMaker$12,990,1032,745

Monogram Capital Raise Timeline

Monogram's first direct-to-investor raise was a $14.6M round in 2019. Since then, Monogram has raised retail capital six additional times, using Reg A+ as a springboard to a Nasdaq listing in 2023.

Each raise brought in new believers—and more importantly, kept bringing them back. That's the long-term power of retail capital. It's not just one campaign—it's a compounding asset that grows with the business.

$80M+
Raised across seven campaigns
~40,000
Investors championing Monogram's vision
20%
Of each raise came from previous investors

Marketing Excellence

DealMaker Reach provided strategic investor acquisition services, helping Monogram connect with the right audience through high-impact channels.

Premium Publications

Targeted campaigns in premium publications like Morning Brew captured qualified investors

High-Engagement Webinars

Engaging events that generated over $4.3 million in investments

Community Building

Strategic approaches that fostered a loyal shareholder base

Investment Momentum

Innovative approaches that amplified investment momentum

Monogram's Journey to Success

Monogram's journey has been defined by relentless innovation, strategic fundraising, and breakthrough advancements in robotic-assisted joint replacement. From early-stage research to a Nasdaq listing and beyond, Monogram's milestones reflect its evolution into a pioneering force in orthopedic surgery:

  • Filed its first patent application in 2017
  • Conducted clinical studies at UCLA and University of Nebraska
  • Expanded the team with key hires
  • Attracted a top-tier advisory board to guide clinical innovations
  • Signed their first distribution partnerships
  • Made headlines with cutting-edge live demonstrations
  • Secured 501(k) FDA clearance for the mBôs surgical system

Nasdaq Debut & Beyond

In May 2023, Monogram Orthopaedics successfully listed on the Nasdaq—a significant milestone offering liquidity and growth opportunities for the company.

For most companies, that would be the end of their story in the private markets. But for Monogram, it was just the beginning of a new chapter.

Public perception says you can't raise privately post-IPO. Monogram proved that wrong.

Defying conventional fundraising norms, Monogram raised an additional $13 million from private investors, powered by DealMaker. This move highlighted the power of a dedicated investor community and provided additional strategic growth capital. Meanwhile, strategic digital marketing for the private offering helped boost the public share price—a win-win for the company and its investors, both public and private.

This was retail capital at its best: strategic, repeatable, and aligned.

One vision. Zero compromises.

This wasn't a one-time raise. It was a multi-year capital strategy.

Retail capital helped Monogram:

  • Go from concept to commercialization without relying on VCs
  • Retain ownership and control in a high-burn industry
  • Build a base of loyal shareholders who invested not once, but over and over again
  • Uplist to the Nasdaq, and still keep raising post-IPO

This is what makes retail capital different. It doesn't expire—it compounds. And DealMaker is built to maximize that long-term value.

Dr. Doug Unis Quote
Ben Sexson Quote

Ready to Raise Capital on Your Terms?

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