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, 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.

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.

Key Takeaways:

The Myth vs. Reality of Partnership: Why making partner isn't all golf courses and schmoozing—it’s running a high-stakes corporate business.

Navigating the "Golden Handcuffs": How massive starting salaries ($200k+) create lifestyle inflation, trapping young attorneys and making career pivots financially difficult.

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.

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".

The "Fudge" Factor: A lighthearted look at family dynamics, professional identities, and why you shouldn't take yourself too seriously, even in Big Law.

00:00:00 – Introduction & Guest Welcome  

00:01:58 – Current Role in Structured Finance at Winston & Strawn  

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

Join the Power Forward Group Financial Advisory Team for a dynamic conversation with Joe Kattan, an ex-Bain & Company employee who transitioned from elite consulting to business ownership. In this episode, hosts Michael Dayan and Ruvin Levavi explore the intersection of formal corporate training and the "Blank Slate" reality of running a startup in 2026.

Episode Breakdown

The Safety Net Strategy: Joe Kattan discusses his deliberate path from the University of Maryland to Bain & Company, explaining how he used elite consulting as a "formal training ground" to build a professional floor and a credentialed resume before taking the leap into entrepreneurship.

The IQ vs. EQ Debate: The team explores the essential skills for modern business, with Michael and Joe concluding that while high IQ gets you in the door, EQ (Emotional Intelligence) and the ability to communicate, build teams, and ask the right questions are the true drivers of long-term success.

Modernizing an "Old Line" Business: Joe shares his "thesis" for acquiring AppraiseItNow, a third-party valuation company. He details how he implemented "no-code" workflow automation and integrated AI to improve lead conversion, quality control, and data hygiene in a traditional service industry.

The Reality of Entrepreneurship: The discussion touches on the fears of non-recurring revenue, the importance of a consistent sales funnel, and critical business planning tools like Buy-Sell Agreements—legal arrangements funded by life insurance to ensure equitable partner exits.

Whether you are a young professional contemplating a career shift or a business owner looking to modernize your operations, this episode provides a masterclass on betting on yourself while maintaining a strategic safety net.

Join Ruvin Levavi and his "younger mentor," Michael Ken , Managing Partner of 1847 Financial in New York , as they dissect the most thought-provoking moments and overarching themes from their annual trip to the New York Times Dealbook Summit. This year's event featured a different lineup than previous years but delivered a wealth of insights from business leaders and politicians alike.

What's Inside this Episode:

1. The Optimism of CEOs vs. The Partisanship of Politicians: The hosts discuss the stark contrast between the optimistic, future-focused visions of company CEOs—who are primarily focused on their next venture, creating a great product, and making the world a better place —versus the disgruntled, and partisan dialogue of American politicians who focus on the next election cycle or what's going wrong. 
2. The Rapid Pace of Technology: A core theme was the incredible speed of change- exemplified by YouTuber Mr. Beast's explosive growth and keen understanding of demographics. They also dive into the world of AI, covering the CEO of Anthropic asking for government regulation to protect society from rapid changes and the efficiency gains AI is introducing into the workforce.
3. Conviction in a Changing World: The hosts highlight the strong convictions of key speakers like Blackrock CEO Larry Fink, who demonstrated the ability to evolve his thinking on crypto and tokenization , and Alex Karp, the energetic CEO of Palantir, who emphasized national security and borders as subservient issues, and proudly stated he is "CEO of the most important, technology company in the world". They also touch on the contentious nature of the interview with Scott Bessent regarding tariffs.

Listen in to gain perspective on the currents driving global finance and technology, and hear personal takeaways from a day of face-to-face connections and challenging discussions that will "always be so important".

Want to invest but don't know where to start? Tune in to this episode of the Power Forward Pod, hosted by the Power Forward Group Financial Advisory Team, as they tackle the foundational principles of investing for long-term success.

This week, Bobby Kaslander and Joe Shalom offer a clear, elementary explanation of the stock market, breaking down complex terms and emphasizing the importance of starting early, especially in a world filled with "fake financial advice".

• The ABCs of Investing: Bobby and Joe define what stocks (equities) and bonds are, explaining that a stock represents a small piece of company ownership, while a bond is essentially a loan to the company. They also clarify that stock market fluctuations are driven by supply and demand, macroeconomic factors (like interest rates and geopolitical risks), and company earnings reports.
• The Power of Diversification and ETFs: Learn why investing in a single stock carries a lot of risk and how Exchange Traded Funds (ETFs) and broad-based market ETFs offer a low-cost, diversified way for new investors to enter the market by owning micro-shares of many different companies, such as all 500 in the S&P 500.
• Why Time-In is Everything: Discover the crucial importance of starting your investment journey "yesterday," as Joe illustrates the shocking power of compounding interest: starting early with less money can yield a significantly higher return over the long run compared to starting later with a higher principal. They also provide practical steps for starting to invest, like opening a brokerage account and prioritizing an emergency fund and clearing credit card debt.

In this episode of The Power Forward Pod, the team welcomes an incredible guest — a venture capitalist, private equity leader, mentor to athletes and entrepreneurs, and now a Shark on Shark Tank. From humble beginnings on the South Side of Chicago to launching a groundbreaking sports investment fund with Mark Cuban, his journey is all about resilience, reinvention, and redefining success.

In this episode, you’ll hear:

How early struggles with money and opportunity fueled a mission to teach financial literacy and create generational wealth.

What really happens behind the scenes of Shark Tank — and how integrity drives every investment decision.

How the new “Sports 2.0” model is changing professional sports ownership and opening doors for innovative investors.

In this episode of The Power Forward Pod, Ruvin Levavi and Bobby Kaslander  dive into Morgan Housel’s newest book, The Art of Spending Money — exploring how our relationship with money shapes not just our financial health, but our happiness, purpose, and peace of mind.

Through honest conversation and real-life examples, the hosts unpack what it really means to spend with intention — and why money itself is only valuable when it supports what truly matters most.

In this episode, you’ll hear:

• How to align your spending with your personal values and purpose — not just status or comparison.
• Why “the art” of money isn’t about formulas, but about understanding what makes you feel fulfilled.
• How to redefine financial success by focusing on family, freedom, and experiences that last.

Tune in now for a thoughtful, down-to-earth discussion that will help you rethink the role of money in your life — and inspire you to pursue financial decisions driven by meaning, not materialism.

Host Ruvin Levavi is joined by team members Michael Danes and David Chabot to discuss the major financial decisions faced by younger clients. The team uses their varying ages and experiences to provide different perspectives on key life events and the financial choices that accompany them.

Topics discussed in this episode include:

• The Cost of Kids: The conversation begins with a discussion on having children and the financial implications. While some, like Michael, are more financially minded about the number of kids they want, others, like David and Ruvin, found the decision was more emotionally driven, with the finances following later.

• Renting vs. Buying: The team dives into the age-old debate of buying versus renting a home. They explore the financial and emotional aspects of the decision, noting that while renting may make more financial sense in the short term, owning a home can provide a sense of stability and ownership that renting can't.

• Financial Planning is Not Linear: The team stresses that while financial plans are often modeled linearly, life is not. Things change, and a good financial plan must be flexible and adaptive to life events, from starting a family to changing careers.

• Investing in Your Future: The episode concludes by emphasizing that while financial planning can be done with a computer program, the decisions are based on life goals and values, not just numbers. The role of an advisor is to help people be more intentional about how they save and invest, helping them to create their own environment and financial future.

Host Ruvin Levavi and original PFG member Chris DeVito discuss the "dangerous income" of a big law salary. They explore how a high income can create a false sense of security and lead to a single-goal-oriented focus on your career, rather than on your overall financial picture.

Key discussion points include:

• The Big Law Dilemma: While a quarter-million-dollar starting salary seems like a lot, expenses and bills can quickly add up, making the income feel "dangerous".
• Lifestyle Creep: As attorneys advance in their careers and their income increases, their savings rate often stays the same, while their lifestyle and expenses grow. This makes it harder to save later on and to make up for lost time.
• The Inversion of Financial Goals: The first financial benefit people often get from a corporate job is a retirement account like a 401(k), but a 22-year-old is more likely to be thinking about paying off student loans or buying a house than they are about retirement.
• Being Intentional: The solution to dangerous income is to be intentional with your finances. By automating savings and periodically checking in on your financial plan, you can avoid the "get to it tomorrow" trap. Carving out a little time for yourself, about an hour and 45 minutes a year, to work with an advisor on a financial plan can help you become a buyer of your own time and lifestyle, rather than a renter

Get ready for an exclusive behind-the-scenes look at the New York Times DealBook Summit! In this episode of The Power Forward Pod, we’re joined by returning guest Michael Kane to unpack the big takeaways, unforgettable moments, and lessons from this one-of-a-kind event. The DealBook Summit gathers some of the world’s most influential leaders, thinkers, and innovators, offering an intimate glimpse into the ideas shaping our future.

What’s Inside This Episode:

• What Makes the DealBook Summit Unique: A look at the event’s unmatched atmosphere, from its intimate setting to its star-studded attendee list.
• Highlights from Top Speakers:
• Sam Altman on the future of AI—insights into OpenAI's path, the rise of ChatGPT, and the optimism driving technological advancements.
• Jeff Bezos on leadership and vision—key takeaways from his standout appearance and what sets him apart.
• Reflections on Bill Clinton's emotional moments and Jerome Powell's surprising personal anecdotes.
• The Power of Live Connection: Why experiencing these discussions in person creates a deeper impact than media soundbites.
• Themes of Optimism and Authenticity:How the human side of these leaders—beyond money and fame—emerged throughout the event.

This episode is packed with practical insights on leadership, innovation, and staying ahead in a constantly changing world. Whether you're leading a team, exploring new ideas, or just curious about what drives today’s movers and shakers, you’ll walk away with fresh perspectives.

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Welcome to the Power Forward Pod, where meaningful dialogues spark transformation! In this episode, our host sits down with Hunter Gimbel, CEO and Managing Partner of The Gaber Group, for a deep dive into the art of financial advisory, leadership, and navigating change in a competitive industry.

Discover the power of collaboration, the importance of legacy, and why both Hunter and Ruvin believe in building firms that transcend their founders.

Key Highlights:

• Leadership Lessons: Hear Hunter's journey of stepping into big shoes and leading with humility while maintaining the company’s legacy.
• Estate Planning Simplified: Learn how financial advisors can approach estate planning with a personal, client-focused lens.
• Scaling While Serving: Explore the balance of wearing two hats—business leadership and client advisory.
• The Future of Financial Advisory: Dive into industry challenges like advisor shortages, AI integration, and fostering trust with clients in a shifting landscape.
• Crafting the Perfect Elevator Pitch: Tips for presenting your value in every interaction, from boardrooms to casual meet-ups.

Take away actionable insights on how to stay client-focused, innovate in your practice, and build a legacy that lasts. 7479903DH_JAN27