The People Behind the Platform

Leadership Forged on Wall Street.
Focused on Your Success.

With over 200 years of combined experience, our Founders are comprised of former Wall Street investment bankers and experts in accounting, audit, securities law, corporate law & governance, deal structuring, securities offering document production and regulatory compliance. Commonwealth Capital’s management is intimately familiar with the criteria employed by institutional sources of capital looking to fund “quality deal flow.”

Founders & Partners

Meet the Team

Timothy D. Hogan
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Timothy D. Hogan

Founder & Partner

Wall Street veteran since 1984. Founding Principal of seven entrepreneurial endeavors. Author of The Secrets of Wall Street courseware. Creator of the Corporate Engineering Conservatory™ and the Financial Architect System™.

Mr. Hogan’s securities industry experience started on Wall Street in 1984 with Merrill Lynch, E.F. Hutton, and Shearson Lehman Brothers (now Salomon/Smith Barney, a Member of Citigroup). He is a former Director of Compliance and Senior Trading Principal for North American Financial Group, Inc., and Chairman of the Investment Policy Committee for North American Capital Advisors, Inc., a SEC Registered Investment Advisory firm.

Mr. Hogan supervised eight internal departments in relation to compliance with federal and state securities laws and held seven NASD securities licenses and registrations, primarily of “Principal” status. He has been a Founding Principal of seven entrepreneurial endeavors, including an eighteen-hole championship golf course, a software development firm, and an investment banking company. He has held board and executive committee seats on various firms.

Mr. Hogan holds a double major (Marketing & Finance) Bachelor of Business Administration from Grand Valley State University’s Seidman College of Business. He is the author of The Secrets of Wall Street: Raising Capital for Start-Up and Early-Stage Companies, the creator of the Corporate Engineering Conservatory™ and the Financial Architect System™.

Russell C. Weigel III, Esq.
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Russell C. Weigel III, Esq.

Founder & Partner

Currently on Sabbatical, Serving as Commissioner, Florida Office of Financial Regulation

AV®-rated securities attorney. Former SEC enforcement attorney (1990-2001). Author of Capital for Keeps. Founder of Investment Attorneys, FL. Commonwealth Capital looks forward to his return from public service.

Mr. Weigel is currently on a sabbatical from our firm as he serves as Commissioner of the Florida Office of Financial Regulation. He contributed part of the compliance framework for the Company, and we believe the work he is doing in Florida to create a capital market and promote investor and entrepreneur education in that state are aligned with the Company’s educational goals. We look forward to his eventual return to the private sector.

Mr. Weigel joined Commonwealth Capital as its Chief Legal Counsel in April 2014. He is a Founding Principal of Commonwealth Capital’s Executive Board and was a senior management team member. Prior to becoming Commissioner, his responsibilities included general corporate and legal-compliance counseling services and serving as a Member of the Investment Policy Committee of Commonwealth Capital’s Income Funds, I & II.

Mr. Weigel is the author of Capital for Keeps, a book designed to help entrepreneurs plan a capital raise and minimize litigation risk. He is an AV®-rated securities attorney, the highest peer review rating from Martindale-Hubbell, requiring 10+ years of bar admission. He graduated from Vanderbilt University with a B.A. in Economics and from the University of Miami School of Law with a Juris Doctor.

Between 1990 and 2001, Mr. Weigel worked for the Securities and Exchange Commission as an enforcement attorney, supervising and conducting numerous investigations and litigating civil injunctive and administrative proceedings nationwide. Between 1989 and 1990, he served the state of Florida as a criminal prosecutor. He was also the former president of Investment Attorneys, a Florida-based law firm launched in 2005 and sold in February 2020.

Mai Luu, CPA, CMA, CFE
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Mai Luu, CPA, CMA, CFE

Founder & Partner

Chief Operating Officer and Executive Director of Educational Programs. Trilingual CPA with M.S. in Accounting, active on the IMA Small Business Committee. With Commonwealth Capital since 2018.

Ms. Mai Luu, CPA, CMA, CFE has been with Commonwealth Capital since 2018 as its Chief Operating Officer. She also serves as Executive Director, Educational Programs, responsible for developing and maintaining relationships with trade associations, trade regulators, and educational institutions including university incubators and accelerators.

Coming from an accounting background with experience in various privately held companies, Ms. Luu has been primarily responsible for all aspects of the accounting department’s operations, from financial statement preparation to internal controls, treasury, audit, and tax compliance.

Ms. Luu is a naturalized U.S. citizen who speaks three languages: English, Vietnamese, and French. She holds two B.A.s, one in French Language & Literature from Vietnam National University and one in Business Administration from the National Economics University of Vietnam, plus an M.S. in Accounting from Northeastern Illinois University. She is an IL-licensed CPA and holds both the CMA (Certified Management Accountant) and CFE (Certified Fraud Examiner) certifications.

She is a member of the Small Business Committee of the Institute of Management Accountants (IMA) and a board member of the IMA Chicago Chapter. An entrepreneur at heart, Ms. Luu has launched small businesses in both the U.S. and Vietnam. Ms. Luu resides in Chicago.

Barbara Matthews, Esq.
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Barbara Matthews, Esq.

Founder & Partner

Executive Director of Capital Markets. Former SVP & General Counsel of Hagerty Inc. (NYSE: HGTY). Co-led the SPAC merger that took Hagerty public. Deep expertise in M&A, IPOs, and corporate governance.

Mrs. Matthews serves as the firm’s Executive Director of Capital Markets. Before joining Commonwealth Capital, Barbara served as Senior Vice President, General Counsel, and Corporate Secretary of Hagerty Inc. (Stock Symbol: HGTY), where she was a co-leader of the team that took Hagerty public through a SPAC merger. In this position, she was instrumental in developing Hagerty’s corporate Board, recognized for its effective governance practices.

Barbara has deep strategic organizational experience in areas critical to bringing a company from privately held to publicly traded. Her mergers and acquisitions experience includes the acquisition of a $700 million equipment leasing business, a start-up “ride share” company, a digital motorsport business, as well as capital transactions including real estate sale-leasebacks, an initial public offering, and a growth capital transaction involving a $200 million investment. She has managed complex joint venture partnerships with banks and financial institutions around the globe and overseen de novo market entry across North America, Asia, Europe, and Latin America.

Barbara currently chairs the Board of the Elk Rapids Downtown Development Authority. She is Chairman Emeritus of Traverse CONNECT, oversaw its transformation into a regional economic development organization, and has served as a Trustee on the Board of Trustees of Munson Medical Center, which anchors the $1 billion Munson Healthcare System.

Blake Woods
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Blake Woods

Founder & Partner

Executive Director & Vice Chairman of the Investment Policy Committee. Co-founder of Jackim Woods & Co. 25+ years in investment banking, M&A, and capital markets. Licensed commercial pilot and real estate broker.

Prior to joining Commonwealth Capital as a Managing Director in 2017, Blake Woods was co-founder of Jackim Woods & Co., a leading middle-market investment banking and M&A firm located in Chicago. Mr. Woods has over 25 years of experience in investment banking, mergers & acquisitions, consultative sales, business operations, and C-Level client representation in B2B environments.

Mr. Woods has advised business owners on exit plans, acquisition strategies, and capital raises. He has worked with subsidiaries of Fortune 50 companies as well as privately held lower middle-market companies. Before co-founding Jackim Woods & Co., he spent three years at MidCap Advisors in Manhattan, nine years in high-end residential and commercial real estate, and served as Marketing Director at The Presidents Forum, a think tank for Presidents and CEOs of middle-market companies.

Mr. Woods earned his undergraduate degree, a master’s degree in Aeronautical Science, and an MBA from Embry-Riddle Aeronautical University. He is a licensed commercial pilot with instrument and multi-engine ratings and a licensed real estate broker in Illinois.

Scott C. Helmholz, Esq.
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Scott C. Helmholz, Esq.

Founder & Partner

Executive Director of Corporate Finance Legal. Former Assistant Director & General Counsel, Illinois Securities Department. 40+ years of securities, regulatory, and energy law experience across state and federal courts.

Mr. Helmholz served as Assistant Director and General Counsel of the Illinois Securities Department between 1983 and 1987. Drawing on his securities industry and regulatory experience, Scott represented broker/dealers and registered representatives in the defense of administrative actions and prepared private placement memoranda for various business ventures. He served as one of the first members of the NASD Board of Arbitrators, representing both claimants and respondents in NASD arbitrations.

Mr. Helmholz opened the Springfield office of Bailey & Glasser LLP in 2009, where he focused on mineral law litigation, representing electric utilities, coal producers, resource owners, and developers. He has argued cases before the Third, Fourth, and Fifth District Illinois Appellate Courts and the Seventh Circuit United States Court of Appeals.

Bar admissions include Michigan (2018), Missouri (1978), Illinois (1983), U.S. District Court (Central and Southern Districts of Illinois), U.S. Court of Appeals 7th Circuit (1989), U.S. Supreme Court (1994), and U.S. Court of Federal Claims (1990). Prior experience includes roles as Special Assistant U.S. Attorney, Special Assistant Attorney General for Illinois, and Law Clerk to the Missouri Court of Appeals. He and his wife reside in Harbor Springs, Michigan.

Robby Crabtree, Esq.
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Robby Crabtree, Esq.

Chief Strategy Officer

Chief Strategy Officer since 2023. Former Dallas trial lawyer with 102 jury trials in his first seven years. Founder of Competitive Storytelling, coaching founders who have raised over $575 million from a16z, Redpoint, Y Combinator and others.

Prior to joining Commonwealth Capital as Chief Strategy Officer in 2023, Mr. Crabtree served many entrepreneurial endeavors, based on his skillsets as a highly-experienced trial lawyer in Dallas, TX. There, he tried 102 jury trials within the first seven years of his legal career. His selling skill at “making the case” to juries successfully, has evolved into an extraordinary ability on coaching entrepreneurs on how to sell professional investors on investing in their start-up or early-stage companies. This fits beautifully with our business model.

As a prosecutor, Mr. Crabtree specialized in violent felonies like robberies and murders before moving into the special crimes unit focused on child abuse cases. During his 16 months in that unit he tried cases of child sexual abuse, child physical abuse, and child death cases. For four years during that time he also coached the national mock trial team at SMU Law School while also teaching Trial Advocacy.

After 7 years as a trial lawyer, Robbie decided to take on a new challenge. He first founded an “edtech” start-up around public speaking for tech company executives and leadership, which was eventually acquired by On Deck at the end of 2020.

Since that acquisition, Robbie founded Competitive Storytelling and turned it into the premier storytelling practice for founders, CEOs, and other leaders inside of the world of technology and venture capital. Since 2021, Robbie has trained thousands of these leaders from start-ups all the way to large public companies to help them become world-class storytellers.

Founders and CEOs, that Mr. Crabtree has privately coached, have raised over $575 million dollars as of June 2023. These efforts have been backed by the biggest venture capital funds in the world, such as; a16z, Redpoint, Y-Combinator, and others. He is partnered with venture firms like Seven Seven Six and is also a venture partner at Antler.

Mr. Crabtree’s approach to storytelling and fundraising comes directly from his experience as a trial lawyer, which is why he’s regularly asked to speak across the world on the subject. He has spoken at Stanford University multiple times where he has addressed the funding gap for minority and female founders while providing a roadmap for how capital allocators and founders can change that dynamic.

Mr. Crabtree grew up in Houston, TX before going to Haverford College in Philadelphia. At Haverford, Robbie played on the baseball team and majored in history, where he wrote his senior thesis on the rise of the religious right: tracing the shift from Jimmy Carter to Ronald Reagan. He was also a Nike sponsored CrossFit Athlete for two years before he turned his full attention to his professional career. He went on to law school at SMU where he graduated in 2014.

Mr. Crabtree is the author of the upcoming book titled Competitive Storytelling.

Mr. Crabtree joined Commonwealth Capital as Chief Strategy Officer to bridge the gap between the legal profession and pre-IPO companies. His skillsets demonstrate how attorneys can further monetize their knowledge and business community contacts to the next level. With his leadership, attorneys can now easily learn how to effectively engage in the more formal corporate / founder experience, within the areas of corporate finance, as opposed to simply practicing law on an hourly basis. In so doing, attorneys not only incubate well capitalized clients, more importantly they hear the world of corporate finance from the perspective of securities within the U.S. private capital markets. Most experienced attorneys simply elevate their knowledge and experience to acquiring board seats on pre-IPO companies, as an alternative avenue to simply practicing law, on an hourly or contingency basis.

Robbie, with his partner Anya (a former litigator turned climate tech founder), lives in the greater Miami area, and can easily maintain a presence in West Palm Beach, FL for company purposes.

Wesley “Wes” Reid
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Wesley “Wes” Reid

Founder & Partner

Co-founder and CTO of Product Lab, LLC (NYC). Builder of platforms for NYSE, American Express, Comcast, Spotify, and Motorola. Digital architect with 20+ years across media and finance.

Mr. Wesley Reid is a co-founder and CTO at Product Lab, LLC in New York City, a digital agency created to partner with entrepreneurs and start-up companies to rapidly accelerate their visions into reality. Since 2001, Wes has designed and built some of the most recognized and utilized platforms across a diverse array of experiences in media and finance.

Wes spent the early years of his career building custom business intelligence applications for commodities trading in Houston, Texas. In the mid-2000s, he relocated to NYC and joined boutique digital agency i33, which was acquired in 2008 by 360i/Dentsu. He subsequently led the next-generation front-end experience for Comcast’s XfinityTV platform, served as Director of Technology for Publicis’ Razorfish in NYC, and served as Chief Architect on landmark projects including Spotify’s first “Year In Music” (2014) and the global launch of Motorola’s MotoX phone.

In the financial sector, Wes led the upgrade of NYSE’s ILM (Issuer Lifecycle Management) platform and subsequently led a global re-platform of American Express’s online customer acquisition process spanning 21 credit card products. He is also a trained jazz musician who attended the New School for Jazz and Performing Arts in NYC.

He resides in New Jersey with his wife and three children.

Jason Bennick
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Jason Bennick

Partner

President of Digital Innovation Group Holdings LLC, a GA Telesis™ company. Co-founder of Product Lab, LLC. Grew AutoLoop from seed to 200+ employees and $65mm ARR. 25+ years building startups, FinTech and technology platforms.

Mr. Jason Bennick is currently President of Digital Innovation Group Holdings LLC, a GA Telesis™ company. There he leads the overall strategy, planning and implementation of innovative business solutions using emerging technologies. His primary responsibilities include building enterprise grade FinTech and data solutions that leverage decentralized networks and technologies to transform old financial products, insecure transactional methodologies and inefficient systems into intelligent, trustless, and transparent protocols that can operate without the high cost and intervention of conventional intermediaries. Areas of management responsibility include business solution architecture, product development & emerging technology planning, resource procurement, go-to-market, profit, and loss volume as well as profitability, sales, business development, capital markets, strategic partnerships, and internationalization. His over decade-long tenure building startups and technology, finance and industry relationships are instrumental in executing on new strategy and converting business opportunities into success for the company and its shareholders.

Prior to joining DIG at GA Telesis, Jason had a history dating back to 1990 in building technology solutions, platforms and SaaS and PaaS solutions. He most recently became a co-founder of a digital product agency, Product Lab, LLC, which is now servicing clients across the U.S. As Co-Founder and Senior Managing Partner for Product Lab LLC, his primary focus has been to develop strategic business solution architecture for enterprise customers in North America, while managing overall P & L, resource development and key client relations for all emerging technology software development.

Before Product Lab, Mr. Bennick spent the prior 12 years building multiple startups, including AutoLoop, which he grew in 2008 from seed phase and less than 6 employees to 200+ doing over 65mm ARR with 100mm market value in 6 years.

Jason began his technology career in the documentary film and broadcast industry in California, where he oversaw the planning, development and production of dozens of studios and facilities while managing and growing global film, video, and broadcast production, eventually responsible for the production and distribution of over 500 videos and films in over 15 languages worldwide.

Jason received his Bachelor’s in Business Administration from American Intercontinental University in Georgia, graduating summa cum laude with a major in International Business, and is a Northwestern California University School of Law candidate (2 years incomplete). He holds professional certificates from MIT Sloan School of Business, MITxPRO, HarvardX and Insead Business School in Entrepreneurship, Blockchain, Contract law and Blue Ocean Strategy respectively. His seasoned leadership and management skills across startups, operational growth and technology transformation for over 25 years emphasize his knowledge and ability to navigate challenging and complicated strategies to successfully launch and expand business opportunities.

Mr. Bennick chairs the Board of Directors for Quube Exchange, a blockchain enabled cryptocurrency marketplace, is Chairman of the Board of Neos Equity Group, a private equity M&A, and is Chairman of World for Human Rights, a non-profit human rights advocacy.

Jason resides in the Greater Tampa Bay, FL, area with his wife and daughter.

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