Startup Lawyers for Chicago, Illinois

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.

Experienced business advisor and in-house counsel with extensive litigation experience, representing parties in a variety of complex commercial disputes, including securities, financial fraud, contract, and antitrust litigation.

Former partner in mid-size firms, now a solo practitioner, with over a decade of experience in commercial real estate, including leasing, acquisition and disposition, and real estate finance.

Illinois-licensed attorney with 9 years of experience in public interest work utilizing advanced skills in contract & project management, compliance, investigation, risk management, & training. Proven record developing and managing partnerships to deliver exceptional results in government agencies, non-profits, law firms, and broad community networks leading to multi-million dollar recoveries, risk management, and execution of large-scale program initiatives. Skills include: 1. Project & Contract Management: 9 years in project & contract management tracking project and contract goals, stages, budgets, and deliverables to lead and support program and department initiatives. 2. Compliance, Investigation, & Risk Management: 9 years in law, policy, & programs conducting investigation, research, writing, analysis, and education in administrative agency and court matters relating to: compliance, financial regulation, contracts, employment, workforce development, healthcare, retirement assets, mental health, disability, taxes, immigration, civil rights, grants, benefits, social services, & criminal defense. 3. Training/Teaching: 4 years training co-workers & community partners; 3 years teaching in U.S. & Ecuador (7 total). 4. Technology: Microsoft Office (including Excel), Contract Express, DocuSign, SharePoint, Westlaw, Lexis Nexis, Concordance, GoldFynch, Clio, Smokeball, Qualtrics, Google Forms, Slack, Zoom, Teams, Webex, & Adobe. 5. Spanish: Advanced Spanish skills from 1 year of teaching, studying, & travel in Ecuador, Peru, & Mexico.

As a resident of the Chicago Southside, Attorney Carissa Essex is a dedicated mother, wife, and attorney. Carissa graduated from the Illustrious Spelman College in Atlanta, Georgia in 2012 with a Bachelor of Arts Degree in Political Science. She then returned to Chicago to obtain her Juris Doctorate in 2016 from DePaul University College of Law. After working in Corporate America for several years as a full-time Legal Project Manager practicing law part-time, Carissa decided to devote all of her time to her legal practice and founded Essex Law in early 2024. Focusing on Family Law and Real Estate Law matters, Essex Law provides exceptional and affordable services to all throughout the Chicagoland Area.

Attorney who focuses on all sorts of civil disputes.

I am an Illinois-barred attorney with 20 years of in-house government and affordable housing experience. I have had responsibilities of a member of the Office of a Chief Legal Officer, am an adaptable "Jill of all trades," and have strong operations and business acumen. I'm also well equipped to work in fast-paced, multi-priority environments, learn new areas of law and deal with unique situations.

Over the course of the past 30 years, in both General Counsel roles (3 times) and in private practice, I have built a successful national real estate transaction, construction, and environmental law practice

Ethan specializes in preparing and structuring transactional deals and advising business owners as outside general counsel. Ethan enjoys working with business owners and entrepreneurs who strive to achieve growth through utilizing modern-day solutions and implementing business strategies that get results. Ethan is passionate about helping families and individuals with disabilities to design, form, and administer special needs trusts, ensuring individuals with disabilities remain eligible for federal and state benefit programs while living their best lives. Ethan has experience from previous firms in civil litigation, estate planning, and regulatory matters. Ethan holds a JD from Chicago-Kent College of Law, and a Masters of Law in Taxation (LLM) from Georgetown Law University Law Center. Prior to law practice, Ethan earned a Bachelor’s degree in Journalism from Indiana University of Pennsylvania and was promoted to Chief Editor at a regional news publication.

Walid J. Tamari, founder and named member of Tamari Law Group, LLC, is widely recognized as one of the nation's top litigators. In 2018, Mr. Tamari was one of only 25 attorneys in the United States to be recognized by the prestigious National Law Journal as a Trailblazer Lawyer. The publication features lawyers who have “shown a deep passion and perseverance of their mission, having achieved remarkable successes along the way.” In addition, America's Top 100 Attorneys® and the National Trial Lawyers have included Mr. Tamari in their top 100 Illinois attorneys lists and the Business Tort Trial Lawyers Association has also selected Mr. Tamari in its “Illinois Top 10” list. Further, for several years, Benchmark Litigation: The Definitive Guide to America's Leading Litigation Firms has chosen Tamari Law Group as one of approximately 25 ranked litigation firms in Illinois. Mr. Tamari is also the past national chair of the Commercial Law League of America's complex commercial litigation committee, a committee comprised of attorneys throughout the nation who practice complex litigation. A distinguished litigator, Mr. Tamari represents clients in high-stakes and high profile civil litigation. He provides clients with result-oriented legal advice and representation in a wide-range of disputes, including claims relating to breach of contract, negligence, business tort and pharmaceutical liability litigation. Mr. Tamari has appeared on CBS News, NBC News, WGN News and Fox News and has been quoted in, among other publications, Forbes, Crain's Chicago Business, Chicago Tribune and the Chicago Sun-Times. Mr. Tamari also teaches entrepreneurship law at Loyola University of Chicago's Graduate School of Business. Committed to giving back to the community, Mr. Tamari has established scholarships at the University of Chicago Laboratory Schools and Loyola University of Chicago's Graduate School of Business. He has served on national advisory boards at Loyola University of Chicago, the University of Chicago Laboratory Schools and Northwestern Medical Faculty Foundation's Neurosurgery Council.

I am a corporate lawyer with extensive experience assisting clients of all sizes, from solo practitioners to enterprise-level international corporations. Over the course of my career, I have negotiated, drafted, and reviewed thousands of contracts spanning a wide range of industries and complexities. My practice is focused on delivering practical, business-oriented legal solutions that help clients protect their interests and achieve their goals.

Hi, I’m Kevin Flaherty, an Illinois-licensed attorney with extensive experience negotiating and drafting complex commercial agreements for engineering firms, technology companies, public agencies, and small-to-mid-sized businesses. Over the course of my career, I’ve: Led negotiations on domestic and international contracts, including engineering services agreements, EPC arrangements, SaaS licensing, MSAs, purchase/supply agreements, NDAs, and other mission-critical commercial documents. Developed risk-allocation strategies around indemnities, liability limits, flow-downs, multi-party contracting structures, and high-stakes project frameworks. Built contract playbooks, drafting standards, review matrices, and workflows designed to help clients understand their risks clearly and move deals forward with confidence. Provided training and guidance to internal teams and leadership on contract strategy, compliance considerations, and best practices. I bring not only legal expertise, but also a practical, problem-solving mindset—translating dense legal terms into actionable business decisions and helping clients protect their interests without losing momentum.