Business

From Contracts to Counsel: Your Essential Guide to Hiring a Probate Attorney in Chicago

Published

2 years ago

March 31, 2024

Like many people, you’ll come across the term probate after a loved one, such as a parent or spouse, passes away. So, what is probate, and why do you need an attorney for it? As defined in Forbes, probate is a legal process that occurs after death. It entails transferring the assets of the decedent (the person who passed) to beneficiaries named in their last will.

With that in mind, having a probate lawyer by your side is essential. The last thing you want to do is deal with the legal complexities of settling a loved one’s estate while grieving. A probate lawyer oversees the validation of the deceased’s will and the fair distribution of assets among family members. One challenge lies in finding a top-quality probate lawyer.

In this guide to hiring a probate attorney in Chicago, we’ll discuss the tips to identify the right legal professional for probate proceedings.

Understand the Responsibilities of a Probate Lawyer

It’s difficult to hire a talented probate lawyer when you don’t know what they do: Start by understanding the roles they play.

When you work with a Chicago probate lawyer, some tasks they might do include:

Act as an estate executor or administrator
Collect proceeds from the life insurance policies of the deceased
Identify and secure the decedent’s assets
Get an appraisal for the deceased’s estate
Pay debts and resolve estate tax issues
Prepare and file documents required in probate court
Transfer assets to rightful heirs
Represent you in litigation proceedings if someone challenges or contests the will

A probate lawyer could also help you and your family navigate state inheritance laws if a loved one dies without a valid will. That way, you can avoid unnecessary taxes or other ramifications of not creating a will, such as losing ownership rights of the deceased’s business or financial support.

Search for Lawyers Online and Offline

You’re probably thinking, where do I find the best lawyer to hire? You could seek referrals from friends or colleagues. Friends who worked with probate attorneys before might provide important details, such as how the lawyers communicate and handle the probate process.

Alternatively, do a simple online search using the terms “probate lawyer near me” or “probate attorney in Chicago.” Go through various websites or online directories and write names of lawyers with positive ratings and customer testimonials. Then, contact the potential lawyers to set up free consultations. Note that not all legal professionals offer free consultations, so make sure to ask before setting a time in your calendar.

Ask the Right Questions

A free consultation provides opportunities to ask questions to better understand if the lawyers in question have the qualifications to handle your probate case.

Four questions you might ask attorneys during the initial meeting may include:

Do You Have Experience in Probate Law?

When evaluating lawyers, prioritize experience. An experienced probate lawyer is aware of common pitfalls that can result in the probate petition being postponed or dropped by a judge. To feel more comfortable about an attorney’s expertise, ask them if they’ve handled probate cases similar to yours before.

For example, let’s say the deceased owned a substantial estate or had complicated assets like royalties and mineral stocks. Working with an attorney with a track record of successfully handling cases like that could save you time and money in the long run.

What Do Other Clients Say About You?

Experience alone doesn’t make a probate lawyer perfect for your case. Look for someone with an outstanding reputation. These reviews likely live on Google next to their business profile or are featured on their website. If you can’t find any endorsements, ask for testimonials written by past clients.

One point to focus on is what reviewers say about the lawyer’s efficiency and speed. Beyond that, does the lawyer offer expert guidance, conflict mitigation, and proper asset management during probate?

A probate attorney in Chicago, IL, should be an efficient expert in asset preservation. This can be crucial to helping avoid hefty taxes and excessive debt claims. Additionally, if the lawyer receives positive feedback on conflict mitigation, it suggests they have experience in resolving or mitigating family conflicts that tend to stall the probate process.

How Long Does Probate Last?

One way to test a probate lawyer’s knowledge is by asking them, “How long does probate last?” While the numbers vary, probate can last for a few months to over a year in many states, including Chicago. When highlighting factors that affect the duration of probate, your counsel might mention things like estate size, family disputes, debt and taxes, absence of a will, and state laws.

A knowledgeable lawyer can explain clearly why your probate case could last a few months or even years. A lawyer that makes too brazen or hard-set of promises might not be the most honest.

How Do You Want Us To Communicate?

There’s no hard rule on how you and your probate attorney communicate. You can talk via text messages, email, video calls, or phone calls. More importantly, check that the attorney communicates in simple language to help you understand your case.

In fact, one essential of a lawyer’s dos and don’ts to gaining clients’ trust is to avoid making clients feel clueless. If a potential lawyer uses complex legal terms or avoids communicating directly, search for probate services elsewhere.

Conclusion: Finding a Probate Attorney in Chicago

Reviewing the will of a loved one after their death and ensuring fair distribution of their assets often involves complex legal issues. For this reason, consider hiring an attorney who specializes in probate law.

To maximize your chances of finding the right probate lawyer, familiarize yourself with their responsibilities. Next, search online for lawyers within your state or ask for recommendations from people you trust. Then, interview prospects to help ensure they possess experience, a remarkable reputation, communication skills, and knowledge of probate law.

Settling the affairs of a loved one who has passed on can be an overwhelming time. A probate attorney can help lift some of the pressure off your shoulders as you focus on grieving and healing.

Business

Derik Fay and the Quiet Rise of a Fintech Dynasty: How a Relentless Visionary is Redefining the Future of Payments

Published

5 days ago

October 17, 2025

Matthew Wiles

Long before the headlines, before the Forbes features, and well before he became a respected fixture in boardrooms across the country, Derik Fay was a kid from Westerly, Rhode Island with little more than grit and audacity. Now, with a strategic footprint spanning more than 40 companies—including holdings in media, construction, real estate, pharma, fitness, and fintech—Fay’s influence is as diversified as it is deliberate. And his most recent move may be his boldest yet: the acquisition and co-ownership of Tycoon Payments, a fintech venture poised to disrupt an industry built on middlemen and outdated rules.

Where many entrepreneurs chase headlines, Fay chases legacy.

Rebuilding the Foundation of Fintech

In the saturated space of payment processors, Fay didn’t just want another transactional brand. He saw a broken system—one that labeled too many businesses as “high-risk,” denied them access, and overcharged them into silence. Tycoon Payments, under his stewardship, is rewriting that narrative from the ground up.

Instead of the all-too-common “fake processor” model, where companies act as brokers rather than actual underwriters, Tycoon Payments is being engineered to own the rails—integrating direct banking partnerships, custom risk modeling, and flexible support for underserved industries.

“Disruption isn’t about being loud,” Fay said in a private strategy session with advisors. “It’s about fixing what’s been ignored for too long. I don’t chase waves—I build the coastline.”

Quiet Power, Strategic Depth

Now 46 years old, Fay has evolved from scrappy gym owner to an empire builder, founding 3F Management as a private equity and venture vehicle to scale fast-growth businesses with staying power. His portfolio includes names like Bare Knuckle Fighting Championships, BIGG Pharma, Results Roofing, FayMs Films, and SalonPlex—but also dozens of companies that never make headlines. That’s by design.

Where others seek followers, Fay builds founders. Where most celebrate their exits, Fay reinvests in people.

While he often deflects conversations around his personal wealth, analysts estimate his net worth to exceed $100 million, with some placing it comfortably over $250 million, based on exits, real estate holdings, and the trajectory of his current ventures.

Yet unlike others in his tax bracket, Fay still answers cold DMs. He mentors rising entrepreneurs without cameras rolling. And he shows up—not just with capital, but with conviction.

A Mogul Grounded in Real Life

Outside of business, Fay remains committed to his role as a father and partner. He shares two daughters, Sophia Elena Fay and Isabella Roslyn Fay, and has been in a relationship with Shandra Phillips since 2021. He’s known for keeping his personal life private, but those close to him speak of a man who brings the same intention to parenting as he does to scaling multimillion-dollar ventures—focused, present, and consistent.

His physical stature—standing at 6′1″—matches his professional gravitas, but what’s more striking is his ability to operate with both discipline and empathy. Fay’s reputation among founders and CEOs is not just one of capital deployment, but emotional intelligence. As one partner noted, “He’s the kind of guy who will break down your pitch—and rebuild your belief in yourself in the same breath.”

The Tycoon Blueprint

The playbook Fay is writing at Tycoon Payments doesn’t just threaten incumbents—it reinvents the infrastructure. This isn’t another “fintech startup” with a flashy brand and no backend. It’s a strategically positioned venture with real underwriting power, cross-border ambitions, and a founder who understands how to scale quietly until the entire industry has to take notice.

In an age where so many entrepreneurs rely on noise and virality to build influence, Fay remains a master of what can only be called elite stealth. He doesn’t need the spotlight. But his impact casts a long shadow.

Conclusion: The Empire Expands

From Rhode Island beginnings to venture boardrooms, from gym owner to fintech force, Derik Fay continues to build not just businesses—but a blueprint. One rooted in resilience, innovation, and long-term infrastructure.

Tycoon Payments may be the latest chess piece. But the game he’s playing is bigger than one move. It’s a long game of strategic leverage, intentional legacy, and generational wealth.

And Fay is not just playing it. He’s redefining the rules.