Dennis W. Hollman, Business Attorney in Milwaukee, Wisconsin
focused on Business and Trusts
Milwaukee, WI
Trusted business attorney serving Milwaukee.
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Quick answer
Dennis W. Hollman is an attorney based in Milwaukee, WISCONSIN. The practice focuses on Business and Trusts.
- Based in
- Milwaukee, WISCONSIN
- Experience
- attorney
- Known for
- Business · Trusts
- Handles Business and Trusts matters from Milwaukee, WISCONSIN.
- Recognized with Best Lawyers in America — Corporate Law (2026).
About Dennis W. Hollman: Dennis W. Hollman is an attorney based in Milwaukee, WISCONSIN. The practice focuses on Business and Trusts.
Areas of practice
Legal matters Dennis takes on
Dennis concentrates on business and trusts. Each area below outlines the kind of case Dennis handles, typical outcomes to expect, and how the intake process starts.
Business cases in Milwaukee, Wisconsin
Dennis takes business matters in Milwaukee, Wisconsin. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before Dennis agrees to represent you.
Trusts cases in Milwaukee, Wisconsin
Dennis takes trusts matters in Milwaukee, Wisconsin. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before Dennis agrees to represent you.
Biography
Meet Dennis W. Hollman — business lawyer in Milwaukee
Dennis W. Hollman is an attorney based in Milwaukee, WISCONSIN. The practice focuses on Business and Trusts.
For over forty-five years, Dennis has advised business owners in all areas of contract and corporate law. He focuses primarily on assisting his clients with business succession planning, estate planning, contract and corporate law—with an emphasis on mergers and acquisitions, and shareholder/partner disputes. One of the founding members of the firm in 1973, Dennis has assisted hundreds of business owners and their companies in structuring successful business succession plans. These comprehensive plans have included assisting business owners in their estate planning, providing the owners—if necessary—with retirement income as part of the plan, and determining who would control the business in the future and when and how changes would occur.
Dennis Assists Clients With
- Business Succession Planning
- Estate Planning
- Mergers and Acquisitions
- Shareholder/Partner Disputes
- Business Financing
- Complex Contractual Matters and Negotiations
- Financial Workouts
Experience/Representative Client Work
- When assisting clients with the transition of the family businesses to the next generation, Dennis structures succession plans which allow the business to remain strong, generate retirement income—if needed—for the transitioning owners, minimize taxes, treat the children equitably to preserve family harmony, and transfer control of the business to children who are best able to continue the successful growth and operation of the business.
- Successfully planning over a thirty-five year period for four generations of family members in a company that grew from a very small contractor to the fourth largest of its type in Wisconsin.
- Facilitated successful management buy-outs of businesses by key employees from existing owners.
- Assisted many family business owners with their retirement planning by structuring purchases of the family business by next generation family members in a setting that provides the owner with retirement income in a secure transaction that does not adversely affect the continued operation of the business.
- Assisted numerous business owners in structuring buy-sell agreements among the owners to create a market for their closely-held stock in the event of their death, disability, retirement or termination of employment at a fair value, while assuring continuity of management and continued operation of the business.
- Structured agreements between sole owners of businesses (who had no heirs interested or involved in the business) and their key employees to allow the owner’s interest in the business to be purchased by the employees at fair market value in the event of the owner’s premature death, while still allowing the owner the right to sell the business at any time during his or her lifetime.
- Successfully negotiated and closed numerous purchase and sale transactions for client’s businesses, including both tax-free and taxable exchanges.
- Facilitated settlements in numerous stockholder disputes without the need for litigation. In a recent case, Dennis’ clients obtained more than eight times their initial settlement offer.
- Provides sophisticated estate planning for affluent clients, by assisting them in transferring, by gift or tax-free sale, large portions of their estates to spousal lifetime access trusts or descendants’ trusts–which are outside of their taxable estates and can substantially reduce estate tax exposure.
Awards/Distinctions
- Selected for inclusion in Wisconsin Super Lawyers, Law & Politics and Milwaukee Magazine.
- Martindale-Hubbell® Peer Review Rating™–AV, reflecting an attorney who has reached the height of professional excellence and is recognized for the highest levels of skill and integrity.
- Selected for inclusion in The Best Lawyers in America®–Corporate Law and Trusts & Estates 2011–present.
Articles/Presentations
- Frequent speaker for business and professional groups on business succession planning and estate planning, including “Transferring the Family Business to the Next Generation,” State Bar of Wisconsin, July 1994.
- Authored numerous articles and an educational handbook on business succession planning and estate planning.
Community Involvement
- Director of the Hebron House of Hospitality Foundation
- Past President and a Director of the Society of Financial Service Professionals–Milwaukee Chapter
- Hunger Task Force of Milwaukee–MATCH Campaign
- Legal Advisor, Tyme Out Youth Center
Education
- University of Wisconsin Law School (J.D.)
- University of Wisconsin–Milwaukee (B.S., Accounting)
How Dennis handles business matters
For over forty-five years, Dennis has advised business owners in all areas of contract and corporate law. He focuses primarily on assisting his clients with business succession planning, estate planning, contract and corporate law—with an emphasis on mergers and acquisitions, and shareholder/partner disputes. One of the founding members of the firm in 1973, Dennis has assisted hundreds of…
Who Dennis represents
Dennis reviews new inquiries case-by-case for business and trusts matters in Milwaukee and the surrounding Wisconsin area.
Credentials
Education, bar admissions, and languages
University of Wisconsin–Milwaukee
BS
Jurisdictions
Dennis's state bar admissions
Wisconsin, State Bar
ACTIVE
Dennis studied at BS in University of Wisconsin–Milwaukee.
Law school and academic background
Dennis completed BS in University of Wisconsin–Milwaukee. Formal legal training is one signal of substantive knowledge — the day-to-day practice Dennis runs in Wisconsin is where that training gets applied to real client questions.
Recognition
Recognition and thought leadership
Dennis has received 10 formal recognitions from bar associations, industry bodies, and peer-review services.
Best Lawyers in America — Corporate Law
2026
Best Lawyers in America — Trusts and Estates
2026
Best Lawyers in America — Additional Areas of Practice:
2026
Best Lawyers in America — Mergers and Acquisitions Law
2026
Best Lawyers in America — Securitization and Structured Finance Law
2026
Best Lawyers in America — Special Focus:
2026
Best Lawyers in America — Estate Planning
2026
Best Lawyers in America — Awards:
2026
Best Lawyers in America — Selected for inclusion in Wisconsin Super Lawyers, Law & Politics and Milwaukee Magazine.
2026
Best Lawyers in America — Selected for inclusion in The Best Lawyers in America–Corporate Law and Trusts & Estates 2011–2024.
2026
Legal awards and honors
Best Lawyers in America — Corporate Law (2026). Best Lawyers in America — Trusts and Estates (2026). Best Lawyers in America — Additional Areas of Practice: (2026). Best Lawyers in America — Mergers and Acquisitions Law (2026). Best Lawyers in America — Securitization and Structured Finance Law (2026). Best Lawyers in America — Special Focus: (2026).
Locations
Dennis W. Hollman's office in Milwaukee
Dennis's primary office is at 111 East Wisconsin Avenue, Suite 1400, Milwaukee, Wisconsin, 53202. In-person meetings are by appointment; a phone intake usually comes first.
Client feedback
Client reviews of Dennis W. Hollman
Dennis has not yet collected verified client reviews on LawyersListed. Reviews here are all from confirmed clients; anonymous ratings are moderated out.
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Schedule your consultationHiring guide
How to hire Dennis W. Hollman — what to expect in your first consultation
Working with a new business attorney should feel structured. Here's how the first two conversations with Dennis usually go, from the moment you request a consult to the day representation begins.
Consultation formats and pricing
Dennis charges for the initial consult. That fee is credited toward representation if you retain Dennis's office.
What to bring to your first meeting
Bring any documents you already have — police reports, medical records, filed pleadings, correspondence from an insurer, a copy of the contract at issue. If you're not sure, err on the side of bringing everything; Dennis will tell you what matters and what doesn't.
Questions to ask a business attorney in Milwaukee, Wisconsin
A short list to run through before you commit: How many business matters have you handled in the last year? What's your fee structure? Who else in the office will work on this? What's your realistic estimate of timeline and range of outcomes? How do I reach you between meetings?
Fees & payment
Fees, payment methods, and consultation options for Dennis
Dennis discusses fees during intake so the arrangement fits the matter. Contingency, hourly, and flat-fee options are all common in business practice — ask which fits.
Hourly rates, contingency fees, and flat-fee options
Every business matter is priced differently. Simple document review might be a flat fee. Injury litigation is often contingency. Complex commercial disputes usually run hourly with a retainer. Dennis confirms the model in the engagement letter before any work starts.
Payment methods and payment plans
Dennis's office accepts standard payment methods. Ask about payment plans if the retainer is a stretch — many business practices work with clients on structured schedules.
Frequently asked
Frequently asked questions about Dennis W. Hollman
How much does it cost to hire Dennis for a business case?
Cost depends on the type of matter, the fee model (contingency, flat, hourly), and how contested the case becomes. Dennis walks through the likely range during the consult so there are no surprises.
Does Dennis offer a free consultation?
Dennis charges for the initial consult; that fee is credited toward representation if you retain Dennis's office. Some business attorneys offer free consults — check Dennis's current terms during booking.
How long do business cases in Wisconsin typically take?
Simple business matters can wrap in a few weeks; disputed cases can run 6–18 months from intake to resolution, longer if the matter goes to trial. Dennis gives a realistic estimate for your facts at the consult — vague answers here are a red flag.
Can Dennis take my case if I'm outside Milwaukee?
Dennis is licensed in Wisconsin. Matters governed by Wisconsin law are the natural fit. Out-of-state matters are handled case-by-case, sometimes with local co-counsel. Ask during intake — Dennis will tell you if the case is a fit or refer you to someone closer to your court.
What should I bring to my first meeting with Dennis?
Bring every document that touches the dispute: contracts, correspondence, police or medical reports, filed pleadings, invoices, photographs, insurance letters. Also bring a written timeline of what happened, in your own words. Dennis will filter what matters — over-preparing at intake is always cheaper than needing a second meeting.
Is Dennis accepting new business clients right now?
Dennis's intake status shifts week to week. Submit the form; the office will confirm availability or refer the matter out.
Areas served
Business attorneys serving Milwaukee, Madison and Waukesha in Wisconsin
Dennis handles business matters throughout Wisconsin. Each city below is a direct link into the search page for verified business attorneys in that community.
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