Robert “Bobby” S. Strauss

Principal

P 312.855.4628

Bobby Strauss brings equal measures of dollars-and-cents analytics, meticulous attention to detail and creative and entrepreneurial big-picture thinking to his work on a wide range of corporate, real estate finance, healthcare and banking matters.

Overview

A natural-born dealmaker, Bobby Strauss brings equal measures of dollars-and-cents analytics, meticulous attention to detail and creative and entrepreneurial big-picture thinking to his work on a wide range of transactional, real estate finance, banking, healthcare and corporate matters. Whether serving in an outside general counsel role, shepherding a consequential merger, acquisition or loan to closing or delivering advice on the business of medicine to those who so practice, Bobby is relentless in his efforts to seize opportunities and control risks for those he represents.

Over the course of countless transactions and engagements, Bobby has yet to find a roadblock he could not overcome to get a deal across the finish line in a way that achieves his clients’ goals and advances their interests. The rare attorney with a mathematical and scientific background, he is able to digest and process information with lightning-fast speed, allowing him to expeditiously and efficiently understand the nuances, potential concerns and long-term implications of a matter. Bobby’s counsel is frank, pragmatic and thoughtful. He seamlessly integrates legal, financial and operational considerations to provide his clients with a holistic, comprehensive understanding of what is on the table and what may lay ahead.

While Bobby’s vast experience extends across multiple industries, he is particularly well-versed in the representation of healthcare providers and practices, including physicians, dentists and related oral health specialists and veterinarians. Bobby understands the priorities and pressures providers face, as well as the multidimensional legal and regulatory issues implicated in their operations and business transactions. He has spearheaded healthcare transactions of all nature and size, allowing his clients to focus on their patients while he focuses on facilitating their sustained growth and success. Bobby also shares his business knowledge with aspiring practitioners, lecturing students at Chicago area dental schools on the legal, business and financial issues they will face in their careers.

In addition, Bobby’s number-crunching inclinations have been a cornerstone of his work as a seasoned commercial finance practitioner. He represents national, regional and community banks and private lenders in lending transactions. He also regularly serves as outside general counsel to family-held businesses and entrepreneurs, including for a multi-family real estate developer as well as a payment facilitator.

Credentials

Education
Chicago-Kent College of Law, Juris Doctor with Honors, 2000
The Chicago Medical School, 1995
The University of Illinois Urbana/Champaign, Biology/Pre-Medicine Double Major

Bar Admissions
Illinois, 2000

Court Admissions
United States District Court for the Northern District of Illinios, 2000

Memberships & Associations
  • PayMaple LLC, Chicago, IL, Co-Founder, Board Member, and General Counsel, October 2017 to Present
  • CityPads LLC, Chicago, IL and Los Angeles, CA, General Counsel, April 2019 to Present
  • The Re-Write It Project, a not for profit, Chicago, IL, Board Member and Vice-President, July 2021 to March 2024 and Board Member and President, April 2024 to Present
  • Chicago Dental Consortium, Chicago, IL, Co-Founder and Member, November 2015 through April 2019, and March 2025 to present