The Face of Entrepreneurial Counsel
With an MBA and firsthand entrepreneurial experience, Thomas R. Del Monte brings a practical, real-world perspective to his work in business and real estate law. Having built and run his own company, he understands the challenges SMT clients face and applies that insight to every engagement. Thomas sees his role as stepping in when challenges arise and guiding clients forward. “I like to dig in and really understand what’s at stake,” he says. He often helps resolve issues before they escalate. Outside the office, Thomas focuses his time on his young family and serves on the board of Legal Aid of Sonoma County.
Thomas Del Monte, 707-524-1900 tdelmonte@smlaw.com, smlaw.com
The Face of Business Lifecycles
“DJ” Drennan is a business attorney with deep experience guiding companies through every stage of the business lifecycle, from formation and growth to mergers, acquisitions and succession planning for family-owned businesses. He helps SMT clients understand complex legal issues through practical, experience-driven advice. In high-stakes M&A transactions involving multiple legal disciplines, DJ coordinates SMT’s attorneys to keep deals moving efficiently while securing strong outcomes for clients. He describes SMT’s culture simply: “We take the work seriously, but we don’t take ourselves too seriously.” Outside the office, DJ enjoys traveling, spending time outdoors and crafting the ideal cocktail.
Douglas J. “DJ” Drennan, 707-524-1900 ddrennan@smlaw.com, smlaw.com
The Face of Trusted Counsel
Barbara Gallagher brings decades of experience across business, real estate, trusts and estates and intellectual property law. Her practice has long focused on helping business owners navigate both professional and personal matters, often building relationships that span decades. Barbara believes effective counsel begins with listening. “What’s most important is that clients feel they were listened to and that they believe I care about what happens,” she says. Known for her thoughtful and relationship-driven approach, she helps clients see the bigger picture while addressing complex legal and strategic issues. Outside the office, Barbara enjoys hiking, Pilates, pickleball, traveling and spending time with her children and grandchildren along the Sonoma Coast.
Barbara Gallagher, 707-524-1900 bgallagher@smlaw.com, smlaw.com
The Face of Business Transactions
A business attorney focused on building long-term relationships with his clients. Andrew Spaulding began his career in litigation before shifting to business-focused work to emphasize collaboration and shared outcomes. “I value relationships that last decades, not just transactions,” he says. Andrew takes a proactive and personal approach to understanding each client’s needs, helping them navigate change and growth over time. Outside the office, he enjoys spending time with his family and is involved in youth-oriented nonprofits—including Luther Burbank Center for the Arts and the Children’s Museum of Sonoma County— supporting arts and education initiatives in Sonoma County.
Andrew Spaulding, 707-524-1900 aspaulding@smlaw.com, smlaw.com
The Face of Conflict Resolution
A fierce advocate for his clients in trial and arbitration, Regan Masi is a civil litigator with extensive courtroom experience. While fully prepared to litigate when necessary, his approach focuses on the efficient and strategic resolution of conflicts through negotiation and settlement when it serves his clients’ best interests. “My goal is to solve problems,” he says, noting that many disputes can be resolved with thoughtful conversation before going to trial. Regan works closely with attorneys across SMT’s practice areas, drawing on the firm’s broad subject matter expertise to support clients facing complex legal disputes. A lifelong Sonoma County resident and Air Force veteran, he brings both perspective and determination to his practice.
Regan Masi, 707-524-1900 rmasi@smlaw.com, smlaw.com
The Face of Strategic Business Counsel
David Chu advises SMT clients on corporate, securities and real estate matters with a strong understanding of both legal and business realities. He works as a strategic partner, blending legal analysis with practical business insight to help clients make informed decisions. As he puts it, “You can be on solid legal footing, but that doesn’t always make it the best business decision.” David helps clients balance risk, cost and opportunity to achieve real-world results. Outside the office, he enjoys playing chess, a pursuit that reflects his ability to anticipate challenges and think several moves ahead.
David Chu, 707-524-1900 dchu@smlaw.com, smlaw.com
The Face of Employer Defense
With a strong litigation background, Kari Brown represents employers in nearly all areas of employment law and litigation, helping them navigate complex and often overwhelming situations. She brings strong analytical skills to her work, with a focus on resolution and practical outcomes. Kari describes her approach as “breaking things down into smaller digestible steps so clients can move forward with their business and with life,” even when challenges feel daunting. She is known for making difficult issues approachable and actionable. Kari has two young children and spends much of her free time with her family, often at sporting events, enjoying time together and staying active.
Kari Brown, 707-524-1900 kbrown@smlaw.com, smlaw.com
The Face of Workplace Counsel
Lisa Ann Hilario helps businesses navigate employment law through a distinctly human lens. Specializing in labor and employment law, she focuses on the intersection of compliance and workplace relationships, helping SMT clients build stronger organizations while navigating complex legal requirements with confidence. “Employment law allows me to focus on the human perspective, not just its complexity,” she says. Lisa Ann works closely with business owners and HR professionals to provide practical guidance that helps them make informed decisions and avoid unnecessary risk. Outside the office, she educates the community about the legal risks associated with hiring private caregivers and domestic employees.
Lisa Ann Hilario, 707-524-1900 hilario@smlaw.com, smlaw.com
The Face of Modern Estate Planning
Jessica L. Alys brings a thoughtful, people-first perspective to her work as an estate planning attorney. She was drawn to estate planning because it combines “complex legal nuance with real human impact.” She focuses on understanding each client’s needs, helping SMT clients navigate decisions with clarity and care. Her approach balances intellectual curiosity with empathy, ensuring each plan reflects her client’s intentions. Having lived in five countries and speaking four languages, Jessica brings a global perspective that shapes how she connects with clients from diverse backgrounds.
Jessica L. Alys, 707-524-1900
jalys@smlaw.com, smlaw.com
The Face of Client-Centered Estate Planning
Kevin T. O’Connor brings a steady and compassionate presence to his work in estate planning, trust administration and probate. It’s an approach shaped by his background as a hospice social worker. He was drawn to estate planning as “a part of the law where I could work with clients to help things go smoothly rather than fighting over them.” Kevin helps SMT clients navigate emotional decisions with clarity, ensuring that plans are thoughtful, complete and easy to understand. His calm, reassuring style makes complex processes feel manageable. Outside the office, his hospice experience continues to inform how he supports families through some of life’s most meaningful transitions.
Kevin T. O’Connor, 707-524-1900 koconnor@smlaw.com, smlaw.com
The Face of Complex Estate Planning
With a background in science and a natural affinity for numbers, Candice L. Raposo brings analytical precision to her work in estate planning, trust administration and probate, with a strong focus on tax strategy. “I’ve always been drawn to the numbers side of the legal profession,” she says, particularly when navigating estate and gift tax issues while recognizing the personal and family considerations involved. Candice is committed to helping clients understand their options so they can make informed, confident decisions aligned with their goals. Outside the office, she volunteers in her children’s classrooms and supports legal education efforts within the Sonoma County legal community.
Candice L. Raposo, 707-524-1900 craposo@smlaw.com, smlaw.com
The Face of Intellectual Property
Warren Dranit practices intellectual property and technology law. With a background in software engineering and advanced training in math and computer science, he brings an analytical rigor that helps SMT clients protect and grow their business, ideas and brands. He is known for his collaborative, thoughtful approach to problem-solving. Outside the office, Warren spends time hiking Northern California’s trails, where he finds space to think and recharge.
Warren Dranit, 707-524-1900 wdranit@smlaw.com, smlaw.com
The Face of Litigation Strategy
A litigation attorney who focuses on research, strategy and motion practice, Annette Holland brings more than 35 years of experience to her work. She collaborates behind the scenes with attorneys across SMT to develop sound legal strategies grounded in a deep understanding of how courts think and decide cases. “A strong argument comes from understanding both the law and how it’s applied,” she explains. Annette’s work strengthens every case the firm handles. Outside the office, she enjoys live music and dancing, often attending performances throughout Sonoma County.
Annette Holland, 707-524-1900 aholland@smlaw.com, smlaw.com
The Face of Business Growth
With a background in engineering, Don Winkle brings a practical, solutions-oriented approach to mergers, acquisitions, and corporate finance. A substantial portion of Don’s practice is in the craft beer and wine sectors. He views his legal work as a means to move businesses forward, not hold them back. “I’m at the positive end of business,” he says. “I help people build things, not argue over them.” Don focuses on delivering solutions that are efficient, realistic and aligned with his clients’ goals. Outside the office, he is passionate about music and actively involved with NorCal Public Media. Don is veteran of the United States Navy’s Submarine Service.
Don Winkle, 707-524-1900 dwinkle@smlaw.com, smlaw.com
The Face of Real Property Law
Mark Miller brings nearly four decades of legal experience across real property, business and estate matters. His thoughtful, measured approach emphasizes truly understanding his clients and their needs. “It’s rewarding when I act as a counselor, helping clients identify options so they are empowered to make informed decisions.” Mark combines legal knowledge with practical insight to guide clients forward with confidence. Outside the office, he supports organizations dedicated to youth services and education.
Mark Miller, 707-524-1900 mmiller@smlaw.com, smlaw.com
The Face of Connected Estate Planning
Ashlee Hellman brings a highly relational and educational approach to her work in trusts and estates. She values the opportunity to connect with clients on a personal level, taking time to understand their stories and priorities. “It’s deeply fulfilling for me to sit down and really listen to people and their stories,” she says. Ashlee helps clients understand their options and make informed decisions that reflect their values. Her work emphasizes clarity, connection and long-term peace of mind. Outside the office, her strong ties to family and community shape the way she approaches both her practice and her relationships.
Ashlee Hellman, 707-524-1900 ahellman@smlaw.com, smlaw.com
