Chad D. Cummings“There is always a better way.”

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“Be a yardstick of quality. Some people aren’t used to an environment where excellence is expected.“

Steve Jobs

“Let us perceive clearly our shortcomings.“

Gautama Buddha

“I was taught that the way of progress was neither swift nor easy.“

Marie Curie

“Tough times don’t last, but tough people do!“


An Introduction

I have served in operations and finance with the world’s largest accounting firm, airline, and bank. Most recently, I developed business intelligence and reporting on commercial banking clients at JPMorgan across a variety of industry verticals—with a special emphasis on FIG and CRE clients.

In 2019, I chose to pivot from my career in finance to pursue law as my next profession.

I completed my Juris Doctor on full tuition merit scholarship in May 2022 and was recognized with the St. Frances Xavier Cabrini award for contributions to the school’s clinical program.

While in law school, I served on the Law Review Editorial Board where my monograph—Transhumanism: Morality and Law at the Frontier of the Human Condition—was selected for publication. I am sitting for the July 2022 administration of the Florida Bar Examination.

After completing my Juris Doctor, I joined the post-graduate Real Property Development LL.M. program at the University of Miami School of Law.

I hold active CPA licensure in Florida and Texas and undergraduate and graduate degrees in accounting and taxation from Southern Methodist University in Dallas.

Previously, I supported capital investment decision-making and financial reporting for the commercial real estate and legal divisions at American Airlines.

Prior to that, I co-founded and developed Food on the Fly, a data mining and logistics startup leveraging mobile connectivity and transactional analytics to deliver premium meals in-terminal to transiting, time-constrained air passengers. My work on this venture is ongoing.

Before making the jump to the entrepreneurial realm, I started my career in the private equity and financial services tax compliance and consulting practice (“SALT-FS”) at PricewaterhouseCoopers where I engineered technical solutions to more effectively serve VC/PE clients including Texas Pacific Group, Goldman Sachs, First Reserve, HGGC, and others.

In 2018, I earned the Certified Management Accountant designation and am currently pursuing CFA chartership and admission to the Florida Bar.

In my spare time, I freelance as a journalist and researcher exploring the taxation and valuation of virtual assets and novel applications thereof.

I also serve as a mentor and coach for university-age small business creators. I live and work in sunny South Florida.

Occasionally, I publish articles covering the taxation of startups. I also address politics, economics, and world affairs as they relate to my interests in airlines, technology, and commercial real estate. My works are featured on Amazon, Entrepreneur Magazine, Virgin‘s blog, Daily Mail (UK), as well as on my personal LinkedIn blog.

Please review the important notices and disclaimers at the bottom of this page, especially prior to contacting me.

Getting in Touch

/Contacting Chad

You are welcome to contact me via LinkedIn, even if we have not previously met.

I am most interested in mentoring exceptionally talented, freethinking university-age small business creators. When appropriate, I am very happy to facilitate introductions to other founders, investors, accountants, attorneys, and industry leaders who I know and trust. I am also available for speaking engagements and interview requests pertaining to transhumanism (i.e., the intersection of biology and technology), the broader startup ecosystem, and intelligent tax planning for entrepreneurs.

Pitch decks may be submitted directly to me by email, although I am most receptive to prior introductions and am regrettably unable to offer detailed feedback on unsolicited materials.

Prior Experience

/Recent Projects

J.P. Morgan Chase & Co
Senior Associate

Data scientist supporting the commercial division of the largest US bank by leveraging sophisticated multivariate forecast modeling

American Airlines
Accounting and Finance
Sr. Financial Analyst

Lead FP&A analyst for real estate division’s capital and operating budget for the world’s largest airline managing long-term facilities planning across ten hubs and over two hundred spokes

Accounting and Finance

Phlexable connects business owners with top-tier CPAs, bookkeepers, and financial analysts to deliver engagements that are collaborative and cost-effective

Flight Attest
Data Mining
Senior Advisor

Consulting for a stealth mode aviation industry startup

Bonhomme Labs
Startup Consulting

Ad hoc consulting for small business startups, including business plan refinement, marketing strategy, financial modeling, capital considerations, and project management

Food on the Fly
Data Science

Conceived, built, and marketed the first-to-market mobile food delivery and transactional analytics platform behind airport security

Private Equity/Venture Capital Tax
Associate, SALT-FS

Engineered technical solutions to more effectively serve clients including Texas Pacific Group, Goldman Sachs, First Reserve, HGGC, and several other boutique investment firms


/Licensure & Education

Certified Public Accountant September 2015 to Present
Florida Division of Certified Public Accounting
Texas State Board of Public Accountancy

Certified Management Accountant July 2018 to Present
Institute of Management Accountants

LL.M., Real Property Development Anticipated Graduation May 2024
University of Miami School of Law

Juris Doctor, cum laude
ABA-accredited Law School

M.S., Taxation
Southern Methodist University, Cox School of Business

B.B.A., Accounting, with departmental honors
Southern Methodist University, Cox School of Business

Reading List

/Recommended Texts

Periodically, I am asked to suggest books which might be of interest to budding entrepreneurs. Below I have included a small selection of literature which I have found to be thought provoking, inspirational, and in some cases, controversial. These recommendations should not be construed as plain endorsements but rather as a starting point for the intellectually curious. As Aristotle would remind us, “It is the mark of an educated mind to be able to entertain a thought without accepting it.”

How to Win Friends and Influence People

by Dale Carnegie

Fear and Loathing in Las Vegas

by Hunter S. Thompson

Foundations of Interior Design

by Susan J. Slotkis

Anatomy of the State

by Muarry Rothbard

Ready Player One

by Ernest Cline


by Yevgeny Zamyatin

Zero to One

by Peter Thiel

The Informers

by Bret Easton Ellis

The Bell Curve

by Richard J. Herrnstein, Charles Murray

This Perfect Day

by Ira Levin

The Logic of Subchapter K

by Laura Cunningham, Noël B. Cunningham

Game Theory for Applied Economists

by Robert Gibbons

Important Notices and Disclaimers:

This website and the material provided here is for informational purposes only, and does not constitute tax, accounting, or legal advice. No person should rely on, or act, or refrain from acting on the basis of any matter or information contained in this website without seeking appropriate legal or other professional advice.

The transmission of information from this website is not intended to create, and its receipt does not establish, an accountant-client, attorney-client, or any other fiduciary relationship. Nor do any interactions or communications we may share via social media, email, or other media create such a relationship. Any materials transmitted to me using the contact information above should not be considered privileged or confidential, and I accept no responsibility for the security or privacy of information you transmit to me via social media, email, or some other mechanism.

This website does not constitute an offer to sell, a solicitation of an offer to buy, or a recommendation of any security. You are solely responsible for determining whether any investment, investment strategy, security, or related transaction is appropriate for you based on your personal investment objectives, financial circumstances, and risk tolerance. All investments involve risk, including the risk of loss of principal.

Reproduction, distribution, republication, and retransmission of material contained within this website or in any of my articles or publications hosted on other websites or fora is prohibited without my prior permission.