1099 Contract Lawyers for Illinois

I am a solo-practitioner with a practice mostly consisting of serving as a fractional general counsel to growth stage companies. With a practical business background, I aim to bring real-world, economically driven solutions to my client's legal problems and pride myself on efficient yet effective work.

A seasoned attorney with deep General Counsel experience and a flexible, business-minded approach to legal leadership. Skilled in collaborating with product, sales, operations, finance, and executive teams — not just to mitigate risk or ensure compliance, but to enable growth, innovation, and efficient deal execution. In my current practice at GCBench, I offer scalable, on-demand counsel tailored to organizations’ changing needs. Legal rigor is combined with operational sensibility, making guidance a facilitator rather than a hurdle. Whether structuring transactions, advising on regulatory matters, or shaping policies, legal strategy is aligned tightly with business objectives.

My name is Ryenne Shaw and I help business owners build businesses that operate as assets instead of liabilities, increase in value over time and build wealth. My areas of expertise include corporate formation and business structure, contract law, employment/labor law, business risk and compliance and intellectual property. I also serve as outside general counsel to several businesses across various industries nationally. I spent most of my early legal career assisting C.E.O.s, General Counsel, and in-house legal counsel of both large and smaller corporations in minimizing liability, protecting business assets and maximizing profits. While working with many of these entities, I realized that smaller entities are often underserved. I saw that smaller business owners weren’t receiving the same level of legal support larger corporations relied upon to grow and sustain. I knew this was a major contributor to the ceiling that most small businesses hit before they’ve even scratched the surface of their potential. And I knew at that moment that all of this lack of knowledge and support was creating a huge wealth gap. After over ten years of legal experience, I started my law firm to provide the legal support small to mid-sized business owners and entrepreneurs need to grow and protect their brands, businesses, and assets. I have a passion for helping small to mid-sized businesses and startups grow into wealth-building assets by leveraging the same legal strategies large corporations have used for years to create real wealth. I enjoy connecting with my clients, learning about their visions and identifying ways to protect and maximize the reach, value and impact of their businesses. I am a strong legal writer with extensive litigation experience, including both federal and state (and administratively), which brings another element to every contract I prepare and the overall counsel and value I provide. Some of my recent projects include: - Negotiating & Drafting Commercial Lease Agreements - Drafting Trademark Licensing Agreements - Drafting Ambassador and Influencer Agreements - Drafting Collaboration Agreements - Drafting Service Agreements for service-providers, coaches and consultants - Drafting Master Service Agreements and SOWs - Drafting Terms of Service and Privacy Policies - Preparing policies and procedures for businesses in highly regulated industries - Drafting Employee Handbooks, Standard Operations and Procedures (SOPs) manuals, employment agreements - Creating Employer-employee infrastructure to ensure business compliance with employment and labor laws - Drafting Independent Contractor Agreements and Non-Disclosure/Non-Competition/Non-Solicitation Agreements - Conducting Federal Trademark Searches and filing trademark applications - Preparing Trademark Opinion Letters after conducting appropriate legal research - Drafting Letters of Opinion for Small Business Loans - Drafting and Responding to Cease and Desist Letters I service clients throughout the United States across a broad range of industries.

I received a bachelor’s degree in philosophy from Northwestern University in 1996 and then got my JD at University of Illinois College of Law in 1999. I have been a lawyer helping people with legal issues in the United States and Internationally since then. That includes drafting and reviewing contracts. I am also passionate about helping small and medium businesses with trademark registration and trademark-related legal projects. The law can be confusing and complicated for people, and I am passionate about providing professional legal services to my clients while simultaneously making the legal process less confusing and stressful for them. My goal is to help clients navigate through both good and difficult times by tailoring my skills, experience, and services to their specific needs.

Clear, strategic legal guidance when you need it most—whether you're planning ahead or defending a position. Legal challenges shouldn't feel confusing or overwhelming. Whether you're building an estate plan, structuring a business, or navigating a dispute, my practice is built on clarity, care, and practical strategy. I work with clients who want real solutions—not just paperwork—through planning and advice that truly fits their goals, families, and businesses. Planning & Structure I focus on estate planning, asset protection, and business succession, helping individuals and entrepreneurs organize their assets, reduce risk, and prepare for every stage of life. Whether you're setting up your first living trust, shielding your business from liability, or updating an existing estate plan, you'll receive clear guidance, fixed-fee pricing, and responsive support from start to finish. Each plan I design is tailored to your real-world priorities: preserving wealth, avoiding unnecessary taxes and probate, and ensuring the people you love are protected when it matters most. I also focus on general business matters outlined below. Disputes & Defense When legal conflicts arise—disputed contracts, demand letters, settlement negotiations, or litigation decisions—I provide realistic risk assessment and strategic guidance. I help clients understand their actual exposure (not just best-case scenarios), identify leverage points, and navigate toward efficient resolution. If you're facing a legal claim or need to evaluate your position before responding, I can walk you through the realistic options and their costs. Services: Estate Planning & Asset Protection --Simple wills and powers of attorney --Living trusts for small estates --Buy-sell agreements for family businesses Business Formation & Agreements --LLC or S-Corp formation filings --Operating Agreements / Shareholder Agreements --Founder or Investor Agreements --Bylaws and Minutes templates --Registered agent setup guidance Contracts & Commercial Matters --Service Agreements (consulting, marketing, software, design, etc.) --Independent Contractor Agreements --Employment contracts and offer letters --Non-compete, non-solicitation, or confidentiality agreements --Employee handbooks or HR policy updates --Termination or severance agreements --NDAs (Non-Disclosure Agreements) --Partnership or Joint Venture Agreements --Sales or Vendor Contracts --Licensing or IP Agreements Terms and conditions SaaS Platforms --Terms of Service --Privacy Policy --Independent Contractor Agreements --Customer/User Agreements --Liability Waivers --Cancellation & Refund Policy --Non-Solicitation Clauses --Marketplace compliance documents Real Estate --Commercial lease drafting or review --Residential lease review --Purchase & sale agreements --Short-term rental (Airbnb) contracts --Property management agreements Professional Approach: I leverage modern legal research and writing technologies—including AI-assisted tools—to enhance the quality, speed, and clarity of my analysis. Like many legal professionals today, I use these tools to organize research, improve communication, and catch errors. On research tools: case law and statutory verification runs through a vLex/Fastcase subscription, and drafting and first-pass review is AI-assisted. Every analysis I provide is thoroughly reviewed and reflects my independent professional judgment as a licensed attorney. AI is a tool that supports my work; it does not replace it.

Navy veteran with 15 years experience practicing law in Chicago.

Mr. McElvenny has extensive experience handling and developing strategy for complex commercial and real estate cases. He’s drafted hundreds of complaints ranging from simple breaches of contract to complex commercial claims including breach of fiduciary duty, constructive trusts and misappropriation of trade secrets. He has an excellent record in trial, arbitration and mediation. He also has significant experience in motion practice in both state and federal court. Through his work in corporate law, Mr. McElvenny has developed considerable experience with Limited Liability Company member disputes and general corporate governance. He’s drafted a number of industry-specific documents such as Operating Agreements (for Limited Liability Companies), commercial leases, settlement agreements and employment contracts. Mr. McElvenny has also represented criminal defendants in felony matters and assisted in the defense of civil matters arising from alleged SEC violations. He has represented individuals appearing before the Illinois Department of Professional Regulation as a result of SEC proceedings. After graduating with a B.A. in Philosophy, Mr. McElvenny proceeded from Loyola University-Chicago to DePaul University College of Law, receiving his JD from that institution in 2002. In 2010, he earned his Master’s of Science in Accounting from Loyola University-Chicago’s Graduate School of Business. Mr. McElvenny was selected to Illinois’ Super Lawyers Rising Stars in 2010, 2012 and 2013.

Financial Services, Business, Corporate, Personal Injury, and Healthcare. I've represented fortune 100 companies and defended individuals in personal debt litigation. Wide breadth of experience, ready to assist.

2008 - Present: Sole Practitioner – Dennis W. Winkler, P.C. Practice primarily in finance and business transactions, as well as commercial real estate transactions. Represent developers, investors, lenders, and businesses, in such matters as: corporate entity selection, drafting and negotiating complex asset purchase agreements, corporate mergers and sales, stock purchase agreements, and various other business contracts for closely related businesses. Involved in a variety of real estate developments, multi-family apartment buildings, construction and acquisition financing, commercial leasing, sophisticated workout transactions, joint ventures, and tax-deferred exchanges. Advise on tax and other savings incentives available to business owners and real estate owners in Illinois. Advise companies involved in related real estate activities such as sales, leasing, property management, brokerage, and construction. Tax experience that includes the representation of taxpayers in State and Federal controversies including: sales/excess tax disputes and responsible parties’ tax assessment protest. Additionally, Dennis has experience in the protest of real estate taxes of commercial and multi-family real estate. As a legal and business advisor, Dennis is committed to helping clients find, develop, and close deals that further their business objectives. Dennis regularly advises entrepreneurs and closely held businesses on matters incidental to their day-to-day business operations as well as their capital raising and start-up needs, corporate structure, private equity raises, and operating agreements. Much like general counsel, Dennis’s breadth of experience allows him to not only provide strategic planning and routine business transactional support to companies, but he also regularly advises on a number of unique issues facing companies by spotting issues and engaging specialists when needed, such as intellectual property, environmental, and bankruptcy counsel. As such, Dennis has been actively involved in sales and acquisitions of manufacturing companies, trucking companies, and logistics companies.

Senior experienced contracts/transactions attorney in the Software Technology space. Also very versed in general corporate legal matters relating to business operations.