Elite Credentials.
Decades of Big Law Experience.
A Personal Commitment to Results.
David Olsky has spent over two decades at the center of complex commercial litigation and high-stakes investigations. With a background shaped at elite national firms in New York, Washington, D.C., and Denver, he founded Olsky Law to bridge a critical gap in the legal market: the need for ‘Big Law’ intellectual rigor without the institutional bureaucracy.
David’s model ensures that the senior strategist you hire is the same person mastering the facts and arguing the case. Whether representing individual investors in obtaining a recovery, navigating disputes among startup owners, or defending financial executives against government inquiries, David’s approach is the same: total immersion. He doesn’t just manage cases; he masters them, ensuring that the partner you hire is the strategist who actually tries the case.
David Olsky is a seasoned litigator with more than 20 years of experience handling complex commercial litigation. He represents individuals and companies nationwide in high-stakes matters, including bet-the-company disputes. He has particular expertise in litigating complex commercial cases on a contingency basis, with clients reaping millions of dollars from his efforts.
David has litigated claims involving securities fraud, partnership disputes, employment, wage disputes, executive pay, corporate governance, breach of fiduciary duty, cryptocurrency and initial coin offerings, fraudulent transfer and fraudulent conveyance, real estate, commercial leases, judgment collection, bankruptcy claims, antitrust, unfair competition, breach of contract, tortious interference with contract, violation of trade secrets, equitable subordination, receivers and bankruptcy trustees, payment processing, financial institutions, attorney malpractice, CBD, marijuana, civil theft, construction, UCC sales of goods, hemp starts, asset-based lending, and insurance coverage.
In addition to his civil practice, David has substantial experience representing individuals and companies in responding to government investigations. He has represented clients before the Department of Justice Antitrust Division, the Securities and Exchange Commission (SEC), the Financial Industry Regulatory Authority (FINRA), and the Office of the Comptroller of the Currency (OCC). His experience also extends to state-level oversight, including matters involving the Colorado Department of Securities, and various State Attorneys General.
Prior to founding Olsky Law, David was a partner at Fortis Law Partners in Denver, senior counsel at Perkins Coie LLP in its Denver office, and a counsel at WilmerHale in its Washington, D.C. and New York offices.
David lives in Boulder with his husband and two children. Outside the office, he enjoys performing improv comedy, which helps him hone his poise, powers of persuasion, and ability to tackle any topic off the cuff—the same skills he relies on in fast-paced courtroom environments.
David graduated summa cum laude from the University of Pennsylvania. He received his Juris Doctor from Stanford Law School with distinction and served as the Managing Editor of the Stanford Law Review.
Following law school, David clerked for the Honorable Bruce M. Selya on the U.S. Court of Appeals for the First Circuit.
- Colorado
- Washington D.C.
- New York
- U.S. District Court, Colorado
- District of Columbia Court of Appeals
- U.S. Court of Appeals, Washington, D.C.
- U.S. District Court, Southern District of New York
- U.S. District Court, Eastern District of New York
- Colorado Judicial Institute board member
- FINRA arbitration panel
- Named to The Best Lawyers in America® list – 2025, 2026 – Commercial Litigation
- Named a Litigation Star by Benchmark Litigation – 2025, 2026
- Quoted, “Ex-Maxar CFO sues for $60M over compensation, board meeting comments” BusinessDen – May 2024
- Quoted, “Centennial movie theater ad firm files for Chapter 11 with 10-figure debt” Business Den – April 2023
- Author, “3 Ways to Protect a Cannabis Business Partnership from Litigation” MJBiz – Oct. 2022
- Author, “4 Questions to Ask Before Pursuing Business Litigation on Contingency” AllBusiness.com – July 2021
- Quoted, “Scott Pack Wanted to be the ‘The Scarface of the Marijuana World’” Westword – February 2020
- Represented CFO in employment litigation against his former employer and its Private Equity majority owner. The matter settled before trial.
- Represented partner ejected from oral partnership by two other partners. The matter settled before trial.
- Obtained arbitration award in favor of client against business partner in complex dispute involving multiple businesses across several states.
- Obtained jury verdict for client on his fraudulent inducement claims against his former business partner.
- Represented a Canadian public company and its American subsidiary seeking damages against its former management in an eight-day bench trial. Obtained a fraud and civil theft judgment awarding his clients over $35 million in damages.
- Obtained judgment in favor of contractor client against homeowners after homeowners failed to pay on work performed on house.
- Obtained arbitration award in favor of client investor against broker-dealer and registered representative that placed him in a Ponzi scheme investment.
- Litigated a 22-day, 14-month trial in Bankruptcy Court on behalf of the Official Committee of Unsecured Creditors of an alleged Ponzi scheme. Following the conclusion of trial and before an opinion was issued, the parties reached a settlement that provided the unsecured creditors with a substantial return of their investment in the fraud.
- Recovered a defrauded investor’s entire investment, with interest, from a Uruguayan corporation.
- Represented a venture capital fund in litigation against the Directors and Officers of a borrower that misrepresented its tax liability on loan documents. Obtained $6 million from the D&O insurer on a $5 million policy.
- Defended a prominent clearing broker in a two-week FINRA arbitration against claims of fraudulent transfer and aiding and abetting a Ponzi scheme. Obtained complete award for defense.
- Represented a payment processor in its claims against a former business partner for breach of contract, tortious interference with contract, and unfair competition, among others. Obtained a favorable settlement shortly before trial.
- Represented one of the world’s largest financial institutions in government investigations of its municipal derivatives and public finance units, including investigations by the DOJ Antitrust Division, US Attorney’s Office, SEC, OCC, and state attorneys general.