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.

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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.

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Patrick Hearn and Eric Dresdale discussed how their company, Entrokey Labs, is redefining cybersecurity for governments, banks, healthcare systems, artists, and more—without requiring a single change to existing infrastructure.

From cosmic radiation to AI-trained entropy, they explain how this lightweight technology delivers seamless, scalable protection—and why now is the moment to take digital security seriously.

Key Discussion Points:

• How quantum and AI threats are quietly destabilizing global systems
• What makes entropy the backbone of encryption—and how to protect it
• Why most organizations are vulnerable without even knowing it
• The breakthrough that led to a 150MB quantum-proof software package
• Why they reject the myth that upgrading to quantum-resistant systems must be expensive
• How AI is now being used to exploit weak keys—and how Entrokey flips the script
• The importance of trustless security in data centers, healthcare, finance, and even live events
• Why modern cybersecurity must evolve at the speed of threat

Takeaways:

• Security is no longer just technical—it’s existential
• AI will find weak keys if you don’t build systems to prevent it
• Quantum resistance is not a luxury—it’s a necessity
• Scalable cybersecurity doesn’t have to be costly or complex
• Protecting identity means protecting lives, not just data

Closing Thoughts:

Patrick Hearn and Eric Dresdale are on a mission to secure the future—one random number at a time. By building a lightweight, software-only shield against the world’s most powerful threats, Entrokey Labs is proving that true cybersecurity isn’t about fear—it’s about preparation, innovation, and scale.

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Jake Claver, after starting with nothing and betting big on digital assets during COVID, turned his financial instincts and crypto foresight into a booming $300M+ advisory firm in under a year. Now one of the fastest-growing RIAs in the world, Jake is bridging the gap between traditional finance and decentralized innovation, giving ultra-high-net-worth families a roadmap to preserve—and protect—their wealth for generations.

Jake Claver shares how he built his business from a personal need for trustworthy digital asset guidance, what he learned from watching a client lose $30 million, and why legacy planning, ethics documents, and mission-driven governance are the new cornerstones of modern wealth.

Key Discussion Points:

• How Jake turned a post-COVID market play into a multi-million dollar crypto portfolio
• Why most traditional wealth managers don’t understand digital assets—and what that means for investors
• The biggest red flags in digital asset management and how to avoid them
• What every Gen 1, Gen 2, and Gen 3 family office needs to future-proof their wealth
• The Rockefeller playbook: legacy planning that lasts beyond three generations
• Why high-net-worth individuals are moving from real estate into crypto
• How to merge TradFi safety with DeFi upside
• The most common (and devastating) mistakes people make in crypto today

Takeaways:

• If you're not thinking about legacy, you're building on sand
• Crypto wealth requires more than returns—it demands protection
• Family charters and ethical frameworks are just as critical as tax structures
• The future of wealth is hybrid: institutional-grade custody meets decentralized flexibility
• Professional guidance in digital assets isn’t optional—it’s survival

Closing Thoughts:

Jake Claver isn’t just managing portfolios—he’s redefining how we think about wealth, legacy, and security in the digital age. In a world of volatility and misinformation, his approach proves that with the right structure, strategy, and values, crypto wealth can be built to last.

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Jordan Sallander, After years working inside tech giants like Apple and Dell, saw a broken system—bloated, slow, and stuck in outdated ways of making IT decisions. Instead of writing reports, he built a company that delivers results. In this episode, Jordan unpacks how IT Select is transforming the consulting industry using speed, automation, and proprietary AI models to save time, money, and sanity.

Key Discussion Points:

• How working at Apple and Dell revealed the inefficiencies of traditional IT buying
• Why slow evaluation cycles are costing companies millions
• The difference between real consulting and binder-pushing
• How IT Select reduces 90-day evaluations down to 9 days
• Building a proprietary AI model to future-proof enterprise tech stacks
• Why speed is the new currency for decision-makers
• What makes IT Select different from every other consultancy
• The trap of “analysis paralysis” in corporate tech decisions

Takeaways:

• Efficiency beats complexity—especially when powered by data
• AI isn’t the future of consulting, it’s the present
• Fast, confident decisions are the edge every company needs
• Being lean, focused, and human-centric can outpace any legacy firm

Closing Thoughts:

Jordan Sallander is building more than a consultancy—he’s creating a new standard for how companies buy and implement technology. By ditching the fluff and embracing automation, he's giving decision-makers what they actually need: clarity, confidence, and speed in a world that moves too fast to wait.

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We sit down with Peter Ferrari, founder and CEO of Jaka Sugar, a wellness-driven startup on a mission to reinvent one of the most misunderstood ingredients in our food system: sugar. After a successful career in real estate development, Peter made a radical pivot into the highly competitive health food industry to introduce Americans to a rare sugar called allulose—an FDA-approved, zero-glycemic alternative that tastes and behaves like real sugar.

Peter opens up about the childhood trauma that sparked his obsession with health, the personal transformation that led to his wellness journey, and the surprising chain of events that introduced him to allulose. He explains why most sugar substitutes fail the taste test, how Japan quietly embraced this ingredient years ago, and what it takes to build a premium food brand from scratch—backed by VaynerMedia and fueled by purpose.

We cover:

• Why Peter left real estate to start a sugar company
• The science behind allulose—and why it matters for your health
• How taste, branding, and trust make or break wellness products
• What the “Pepsi Challenge” taught him about market perception
• Lessons from launching a DTC brand with world-class assets
• Why the current food movement is the biggest opportunity for wellness brands

If you're a health-conscious consumer, founder, or investor curious about the future of food and functional wellness, this is a conversation you won’t want to miss.

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