M&A Veteran Brings Deal-Making Innovation to Commercial Real Estate

Written by:

Date:

27 Mar 2025

After executing more than 50 deals over his 20-year career in mergers and acquisitions, Jan Tomaszewski was frustrated by an industry truth that most professionals accept as inevitable: complex transactions are slow, expensive, and risky. Now, he’s bringing his expertise to revolutionize how real estate deals are executed through RedlineDCS, a secure transaction platform designed to streamline the entire process.

“My experience was lawyers are templates and the interactions I have with my attorney, while there are meaningful interactions of genuine counsel that will help make strategic decisions, my lawyer is also doing the secretarial work of putting the PDFs together, having drafts, sending them, meeting invites, and all those interactions are billed, and they add up,” explains Tomaszewski.

This inefficiency is particularly painful in commercial real estate, where complex transactions often involve multiple stakeholders, extensive documentation, and tight timelines. The traditional process relies heavily on email chains, scattered document storage, and time-consuming coordination between parties – all creating significant expense and opportunity for error.

From Investment Banking to Innovation

Tomaszewski’s journey through investment banking, private equity, and corporate development gave him unique insight into transaction inefficiencies. As the head of corporate development at an ed-tech compliance training provider, he noticed that while legal fees might be proportionally reasonable for billion-dollar deals, they became prohibitively expensive for smaller transactions.

“If you’re going to do a $100 million transaction, $2 million of legal fees are a rounding error in the percentages of the cost of the entire deal, but if you’re doing $1 million, $500K, these small deals, $100K of legal fees proportionally is quite high,” Tomaszewski notes.

This observation became particularly relevant when considering real estate transactions, where the process shares many similarities with M&A deals. Both follow standard stages – confidentiality agreements, offer terms, due diligence, and legal documentation – but often lack technological innovation to streamline these steps.

The similarities weren’t lost on Tomaszewski. “The process of which you’re buying a business, versus real estate versus any tangible assets, follow the same process, right? You have first agreement of confidentiality, which is an NDA. Then you have the offer and the terms. And then you go into diligence. And then finally, the legal process where you bring in your outside counsel.”

Three-Pronged Value Proposition

RedlineDCS offers what Tomaszewski describes as “three value prongs”: mitigating deal risk, lowering transaction expenses, and shaving weeks off deal timelines.

The platform’s approach to risk mitigation addresses common pain points in real estate transactions. For example, Tomaszewski highlights the nightmare scenario every deal-maker fears: “It’s as simple as sending the wrong email to the wrong party. James Thompson is your attorney. The opposing counsel could be Jimmy Thompson. It takes just being tired and sending your notes of the latest draft with what may say, ‘hey, what’s the seller’s thinking’ that can go to opposing counsel. That is a big deal risk that you can’t take back.”

Instead of relying on email attachments, RedlineDCS provides secure links that can be disabled if sent incorrectly. The platform adheres to HIPAA standards, recording every login and action for audit purposes – critical for high-stakes real estate transactions where confidentiality breaches can jeopardize deals.

For expense reduction, the platform eliminates inefficient communication workflows that drive up billable hours. When discussing the current process, Tomaszewski points out, “Your communication mechanism could be used directly on the documents, so at your leisure, and then your counsel’s availability, you can just jump in and tackle the document versus traditional means of, ‘Hey, when are you available? I’m available Friday. Okay, how about 3pm? Oh, at three, I can’t.’ That interaction is probably $1,000 worth of fees.”

The time-saving aspect is equally compelling for real estate professionals facing competitive markets where delays can kill deals. By facilitating real-time collaboration during due diligence, RedlineDCS prevents the common scenario Tomaszewski describes: “If you send out the diligence list on a Monday, that afternoon, you can see progress on one or two of the items. Alternative today is send it out on Monday, Saturday morning, you receive a full list of all ‘Not Applicable’ responses. So now there’s a week lost.”

Market Validation

Currently self-funded, RedlineDCS has already garnered significant market interest with 60 organizations using the platform and over 150 in trial phases. The company maintains close relationships with what Tomaszewski calls “Cornerstone customers” – early adopters who provide crucial feedback and validation.

This feedback loop has driven continuous improvement. One notable example came from an investment bank user who requested AI capabilities to analyze virtual data rooms. This led to the development of RedlineDCS 2.0, which incorporates a legal large language model to summarize provisions, explain agreements, and assess risk in responses.

“We’re looking to build that, because that was just a direct ask from one of our users who manages NDA campaigns for investment banks,” Tomaszewski says.

The Great Wealth Transfer

Beyond immediate transaction benefits, Tomaszewski envisions RedlineDCS playing a significant role in what he calls “the great wealth transfer” – the massive transition of assets from baby boomers to the next generation, including substantial real estate holdings.

“There are trillions of assets held by baby boomers that are going to have to transfer, whether it be from family to family, from trust to trust. There’s going to be a mechanism, there’s going to be lawyers involved, bankers involved, advisors,” he explains.

This transfer represents both a challenge and an opportunity for the real estate industry. Without accessible transaction tools, Tomaszewski fears that only large institutional players will be able to participate effectively due to their resources and access to technology. By democratizing deal execution, RedlineDCS aims to give smaller players a fighting chance.

“The goal is to first let the large language model get you to a good point. And then we would have a very similar ‘ask a CPA’ model where built into a contract of M&A attorneys, or real estate attorneys who, you know their rates. And you can say, this guy’s $300 and this gal is $700, they can come in and do a once over on your agreement.”

This approach could reduce legal fees from $25,000 to $5,000 while creating a comprehensive archive of all real estate information – particularly valuable for future refinancing or additional transactions.

Looking Ahead

As RedlineDCS continues to grow, Tomaszewski remains committed to the mission of making deal execution more efficient, secure, and accessible. The platform’s emphasis on security – with SOC2 compliance, private US-based servers, and comprehensive data protection – positions it to address growing concerns about confidentiality in real estate transactions.

For real estate professionals constantly juggling multiple deals, perhaps the most compelling aspect is simply the time saved on everyday frustrations. As Tomaszewski points out: “If my CEO messaged me, ‘Hey, what’s the latest draft of the purchase agreement today?’ I could go through my emails and try to find the latest draft, and that could take 20 minutes, or I can email my attorney, ‘Hey, do you have the latest draft?’ I’m sure they do. Ten minutes later, I get the email and has the latest draft. The interaction: $500.”

With RedlineDCS, that same scenario becomes a quick sharing of a secure link, saving both time and money – a proposition likely to resonate with deal-makers across the real estate industry who understand that in competitive markets, efficiency isn’t just about cost savings, it’s about winning deals.