George Dimov isn’t your average tax guy. He’s the one people call after their DIY filing goes horribly wrong. In this episode, George breaks down why even high earners and finance pros are missing massive savings, and how early planning and the right structure can mean the difference between overpaying and winning the long game.

Key Discussion Points:

• The most common tax mistakes professionals and founders make
• Why tax apps and quick DIY filing often lead to surprise bills
• How equity comp, crypto, and stock sales create hidden tax traps
• The right (and wrong) way to structure your business
• Why February is too late to start thinking about tax strategy
• The secret to reducing your alternative minimum tax
• Why George’s firm is always on call—weekends and all
• What upcoming tax law changes could mean for busy professionals

Takeaways:

• Most tax savings are lost due to lack of early planning—not lack of tools
• Choosing the wrong business structure can cost you tens of thousands
• Your CPA should be a partner, not a paper pusher
• The earlier you plan, the more you keep—and the fewer surprises come April

Closing Thoughts:

George Dimov believes tax season should be a celebration, not a scramble. His mission is simple: empower clients with clarity, strategy, and hands-on support—so they can build wealth without worrying what’s around the corner.

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Shekar Natarajan shares his remarkable journey—fueled by miracles, mission, and a promise to his son. In this episode, he unveils how Orchestro.AI is building the foundational rails for the next generation of supply chains—without ripping up what already exists.

Key Discussion Points:

• Growing up with 8 people in a one-room home—and the father who gave away his last rupee
• The promise Shekar made to his newborn son that became the mission of Orchestro.AI
• Why today’s supply chain system is broken and inaccessible for small businesses
• The $1.3 trillion problem hiding inside global logistics
• How Orchestro.AI is creating an open, AI-powered infrastructure to unite fragmented systems
• Why he believes this is like the early days of the internet
• The mindset Shekar looks for when hiring—and why resumes come second
• What big companies get wrong about innovation—and how grassroots systems can win

Takeaways:

• Fixing complex systems doesn’t always mean tearing them down—sometimes it means connecting them
• AI’s greatest promise isn’t automation—it’s amplification of human effort
• Miracles, when honored, can fuel missions that outlast a lifetime
• Founders with purpose build companies that people want to believe in

Closing Thoughts:

Shekar Natarajan isn’t just building a company—he’s building the future backbone of global commerce. With humility, purpose, and visionary grit, he’s proving that the most powerful innovations are born not from disruption, but connection.

Hosted on Acast. See acast.com/privacy for more information.

Jake Claver went from M&A consultant to one of the fastest-growing figures in digital asset wealth management—turning his early crypto success into a $300M+ registered advisory firm in just seven months. In this episode, he shares how he identified the massive trust gap in digital asset services, built a solution for high-net-worth and ultra-high-net-worth clients, and now helps family offices avoid catastrophic mistakes—including one client who lost $30M in a single transaction.

Key Discussion Points:

• Why legacy wealth advisors were unprepared for the rise of digital assets
• How Jake turned a personal need into a market-leading advisory firm
• What family offices need to do now to protect generational wealth
• The surprising reason most crypto millionaires lose it all by Gen 2 or Gen 3
• Building “family compasses” and ethics docs to future-proof legacy
• Why DeFi’s chaos demands TradFi’s structure
• How his firm mitigates risk, custody, and compliance—without giving up upside
• The $30M mistake that changed everything

Takeaways:

• Success in digital assets means nothing without structure
• The future of wealth management lies at the intersection of crypto and compliance
• Most people don’t need more options—they need more trust
• Legacy is built by planning for the next 100 years, not just the next cycle

Closing Thoughts:

Jake Claver is quietly setting a new standard for digital wealth management—fusing the flexibility of crypto with the rigor of legacy finance. In a world full of volatility and misinformation, his firm offers what people actually need: clarity, structure, and the security to build generational wealth that lasts.

Hosted on Acast. See acast.com/privacy for more information.