Business

Winnipeg’s Two Entrepreneurial Brothers Who Have Invested Millions Before Their Mid-Twenties

Published

5 years ago

February 8, 2021

Winnipeg’s real estate market has been steadily increasing over the last few months, which is a surprise to many, considering the pandemic’s recent results. It’s a great time to take advantage of things and purchase or sell a property, especially for those starting out in real estate. Thanks to current low-interest rates, there’s no better time to try one’s hand in the industry, and that’s exactly what brothers Jordan and Luke Lintz have done.

Co-founders of HighKey Holdings Inc. and the companies under it, the duo have recently launched their real estate brand. Though less than a year old, HighKey Real Estate has already bought up two apartment buildings, totaling over $5 million. These aren’t small numbers, especially for the city of Winnipeg, but the brothers aren’t stopping there.

Over the next few years, they have plans of renovating their apartment buildings, with over $1 million-worth of work going into each one. One of HighKey’s goals is to bring value back to the area by fixing things up, but also adding to the neighborhoods; they’re preserving the charm of Winnipeg. Though it will take a couple of years to see the grand reveal of each building, it will be exciting to see what Jordan and Luke come up with when the time comes.

The two brothers haven’t been in this by themselves, though. Their real estate brand has been collaborative work with a local real estate coaching company named BlackCard University. BlackCardU is the lasting legacy of the late Stefan Aarnio, a self-made millionaire, and entrepreneur as well as a former business partner of Jordan and Luke.

Before his passing in May of 2020, Stefan was a well-known real estate investor and coach in North America. He began his own company named BlackCardU, a coaching program for real estate investors and trainers to grow their skills surrounding the industry. Based in Winnipeg, Manitoba, the company has already helped hundreds of people in finding new careers for themselves.

Jordan and Luke quickly realized how beneficial it would be to team up with BlackCardU as they scaled HighKey Real Estate. The team of professionals at the company, especially Canadian real estate experts Damon Woodward and James Dmytriw, were a massive help in getting things in order and securing deals. Their vast knowledge of the industry played a big part in making sure everything was up to HighKey’s elite standards.

For the future, the brothers are hoping to expand their portfolio of the company’s with luxury developments and apartment buildings and offer more to their clients. This will happen in the form of investment options through HighKey Real Estate, which will be available to clients and friends.

It’s clear the brothers aren’t taking things slowly as they scale their business, and we’re interested to see what their future holds. To keep up with the HighKey brand yourself, you can find them on their Instagrams, @HighKeyCo, @HighKeyClout, @HighKeyAgency, and @HighKeyRealEstate.

Business

Click for Counsel: YesLawyer Wants to Make Lawyers as Accessible as Wi-Fi

Published

1 day ago

April 1, 2026

Matthew Wiles

Photo Courtesy of: YesLawyer

Byline: Andi Stark

For many people facing a legal problem, the most difficult part is not understanding their rights but finding a lawyer willing to speak with them in the first place. Long wait times, unclear pricing, and administrative hurdles often delay even the most basic consultations. YesLawyer, an AI-enabled plaintiff firm operating across all 50 states, is testing whether technology can shorten that gap.

Founded in 2024 by 25-year-old entrepreneur Rob Epstein, the platform offers free intake, automated screening, and, in many cases, same-day conversations with licensed attorneys. The idea is simple: reduce the friction between a client’s first request for help and an actual legal discussion. In this interview, Epstein explains how the system works, where artificial intelligence fits into the process, and what problems the company is trying to address in the broader legal system

Q: When you say you want lawyers to be “as accessible as Wi-Fi,” what does that mean in practical terms?

A: It’s a way of describing speed and availability. Someone dealing with a workplace dispute, a serious injury, or an immigration issue should be able to move from an online form or phone call to a real conversation with counsel in hours, not weeks. YesLawyer is structured so that a client begins with a free case evaluation, goes through automated conflict checks and basic screening, and, in many instances, speaks with a lawyer the same day.

Q: How does the process work once someone contacts the platform?

A: We use a structured workflow. It starts with a short questionnaire and an initial conversation to capture basic facts. That information feeds into conflict checks and internal review. The system then proposes a match with a licensed attorney and provides a calendar link for a virtual consultation, often within 24 hours. After the meeting, the client receives a written legal plan outlining next steps, deadlines, and estimated fees.

Q: Where does artificial intelligence fit into that process, and where does it stop?

A: AI is used for organizing and routing information, not for giving legal advice. It helps with conflict checks at scale, case categorization, and structured summaries so attorneys can focus on the substance of the matter. Every consultation is conducted by a licensed lawyer, and all decisions about strategy or next steps are made by humans.

Q: What problem is this model trying to solve in the current legal system?

A: Delay and cost are still major barriers. Many civil plaintiffs face long waits just to get a first appointment, along with high retainers and hourly billing that make early legal advice risky. We try to respond with faster consultations, flat-fee options, and financing. The idea is to remove administrative friction so lawyers spend less time on logistics and more time speaking with clients.

Q: Some critics say platforms like this blur the line between a technology company and a law firm. How do you describe YesLawyer?

A: We describe ourselves as a national, AI-enabled plaintiff firm that connects clients with independent attorneys. That structure does raise regulatory questions, especially around responsibility and oversight. We focus on licensing verification, attorney-written case plans, and clear communication about fees and services.

Q: You’ve said the main bottleneck is “systems” rather than people. What do you mean by that?

A: The issue isn’t that lawyers don’t want to help more people. It’s that the systems around them make it hard to scale their time. Intake, scheduling, and document handling take hours. Automating those parts means attorneys can handle more matters without being overwhelmed by repetitive tasks.

Q: Does this model risk favoring only the most profitable cases?

A: That’s a real concern in legal technology. Automation often works best for repeatable, high-volume disputes. Our view is that lowering administrative cost can actually make it easier to take on smaller or more complex cases that might otherwise be turned away. Whether that holds over time depends on the data.

Measuring Impact Over Time

YesLawyer’s attempt to compress the timeline between inquiry and consultation reflects broader changes in how legal services are being delivered. As artificial intelligence becomes more common in administrative work, firms are experimenting with new ways to reduce wait times and clarify costs.

The company’s early growth suggests that many clients value faster access to an initial conversation, even before considering long-term representation. Whether this platform-based model becomes widely adopted or remains one of several emerging approaches will depend on regulatory developments, lawyer participation, and measurable outcomes for clients. For now, YesLawyer’s experiment highlights a central question in modern legal practice: how quickly can help realistically be made available to the people who need it.