Inside the Big Law Mindset with Reuben Levavi
Where You Can Listen
![]() | ![]() | ![]() | ![]() |
Description
What happens when you graduate from a top-tier law school right into the teeth of the 2008 financial crisis? In this kickoff episode of our new season focusing on Big Law attorneys, we sit down with Reuben Levavi, Of Counsel at Winston Taylor, to unpack his incredible journey through the legal landscape.
From starting his career at a mega-firm that suffered the largest bankruptcy in legal history, to navigating the high-stakes world of corporate salaries, Reuben shares raw insights into what the practice of law actually looks like behind the curtain. We dive into his transitions between Big Law and in-house roles, the shifting dynamics of modern work-life balance, and the irony of building a thriving practice around the very financial instruments that triggered his rocky career start.
What's Inside this Episode
1. The Myth vs. Reality of Partnership: Why making Partner isn't all golf courses and schmoozing, it’s running a high-stakes corporate business.
2. Navigating the "Golden Handcuffs": How massive starting salaries ($200k+) create lifestyle inflation, trapping young attorneys and making career pivots financially difficult.
3. Big Law vs. In-House: The truth about work-life balance and why moving in-house isn't always the automatic safety valve people think it is.
4. Full-Circle Resilience: How Reuben built a successful career in Residential Mortgage-Backed Securities (RMBS) after the 2008 crash originally left his career goals in a "ghost town".
5. The "Fudge" Factor: A lighthearted look at family dynamics, professional identities, and why you shouldn't take yourself too seriously, even in Big Law.
About Our Guest
Reuben focuses his practice on structured finance transactions involving residential and commercial mortgages and other asset classes.
Reuben represents clients with respect to purchases and sales of residential mortgage loans, unsecured consumer loans, solar loans and other asset classes; repurchase and other warehouse financing facilities collateralized by various assets including residential mortgage loans and other related matters.
Reuben also represents investment banks, financial institutions and other market participants in their roles as issuers, underwriters, servicers and sellers in both public and private offerings of asset-backed securitization transactions, including those involving residential mortgage loans, consumer loans, auto loans and leases, equipment loans, device payment plans and commercial mortgage loans.
Prior to joining the firm, Reuben served as associate general counsel for a technology-driven registered investment advisor, where he managed an active 144A securitization shelf, negotiated several term loan and revolving warehouse facilities, and supported the firm’s capital markets, financial operations, partnerships and investor relations teams. Prior to that, Reuben was a capital markets and structured finance attorney at other top-tier international law firms.
Time Stamps
00:00:00 – Introduction & Guest Welcome 00:01:58 – Current Role in Structured Finance at Winston Taylor
00:02:18 – Graduating NYU Law (2008) & The "Ghost Town" at Dewey & LeBoeuf
00:04:47 – Why Law School? First Amendment Aspirations vs. Reality
00:08:25 – The Law School Experience & Learning How to Think
00:11:00 – "Golden Handcuffs" & The Myth of Law Firm Partnership
00:15:10 – Why Transactional Law is Like Solving Puzzles
00:17:28 – Furloughs, Tax LLM, and the Largest Bankruptcy in Law Firm History
00:21:11 – Big Law vs. In-House Practice: Culture and Work-Life Reality
00:27:18 – The Future of Big Law: AI & Generational Shifts
00:30:01 – Full Circle: Rebuilding a Career in Mortgage-Backed Securities
00:33:18 – Family Inside Jokes & Episode Wrap-Up
Whether you are a financial advisor looking to better understand the mindset, compensation traps, and career pressures of your attorney clients, or you just appreciate a masterclass in professional resilience, this episode is a must-listen.
Disclosure
For education use only- not to be relied upon as financial advice. The information provided is for educational purposes only and is not intended as investment advise or a solicitation for the purchase or sale of any product or security. Investing includes risk, as well as the potential loss of the money you invest. Insurance and other financial products and services could be subject to certain terms, eligibility requirements, conditions and costs, and may not be right for everyone. Past performance is not a reliable indicator of future results. Referenced indices are unmanaged and do not reflect sales charges; it is not possible to invest directly in an index. Securities and investment advisory services offered through Hornor, Townsend & Kent, LLC (HTK), Registered Investment Adviser, Member FINRA/SIPC, 800-873-7637, www.htk.com. Power Forward Group is unaffiliated with HTK.9024687DH_JULY28



