Crypto taxes are getting more complicated fast — especially for investors, accountants, and financial advisors trying to keep up with new IRS reporting rules.

Perry Woodin is the CEO and co-founder of Node40, a digital asset accounting and analytics platform focused on crypto tax reporting, compliance, and financial reconciliation. In this episode, Perry breaks down the growing challenges around crypto taxes, 1099-DA reporting, digital asset compliance, and how financial advisors can better manage crypto within client portfolios.

He also explains how crypto investors create taxable events without realizing it, why many broker-issued crypto tax forms may be inaccurate, and how advisors and accountants can stay ahead as digital assets become more mainstream.

Key Takeaways:

● Crypto tax reporting is evolving quickly: New 1099-DA rules are creating confusion for investors, accountants, and advisors navigating digital asset compliance.

● Many crypto tax forms may be incomplete: Investors using multiple wallets or exchanges often receive inaccurate cost-basis reporting.

● Financial advisors need crypto visibility: Advisors increasingly need insight into digital asset holdings to manage full portfolio strategy and tax planning.

● Blockchain creates massive data complexity: Crypto transactions, staking rewards, liquidity pools, and yield strategies generate difficult-to-track tax events.

● Education remains the biggest hurdle: Many investors and professionals still underestimate the importance of understanding crypto tax obligations.

Estate planning isn’t just legal—it’s strategic, personal, and often misunderstood.

Natalie Smith, attorney at Sussman Shank LLP, specializes in advanced estate, trust, and tax planning for families, business owners, and advisors. With an LLM and deep experience at the intersection of tax law and real-world decision-making, she helps clients align wealth, values, and long-term intent.

In this episode, Natalie breaks down what “advanced” estate planning actually means, where high net worth families and business owners make costly mistakes, and how early coordination with advisors can dramatically improve outcomes. The conversation highlights practical strategies around trusts, gifting, tax mitigation, and family dynamics—while emphasizing that clarity, communication, and timing are what truly drive effective planning.

Key Takeaways:

● Know your assets: A complete, organized asset list is critical to ensure your estate plan actually works as intended.

● Titling matters: Even the best trust structure fails if assets aren’t properly aligned and funded.

● Plan before liquidity events: Early coordination helps avoid major tax consequences during sales or exits.

● Family dynamics drive strategy: Effective planning must account for relationships, roles, and communication.

● Start earlier than you think: Estate planning is most effective when treated as an ongoing, proactive process.

Connect with Natalie:

Website: https://www.sussmanshank.com/people/natalie-e-smith-ll-m/

LinkedIn: https://www.linkedin.com/in/natalieelizabethsmith/

With Your Guest Host Seth Krussman:

Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.

Connect with Seth:

Website: https://www.brayshawfinancial.com/

Podcast: https://www.brayshawfinancial.com/money-on-tap

Facebook: https://www.facebook.com/3Dinvesting/

X: https://x.com/BFG_LLC/

Helping seniors navigate one of life’s biggest transitions requires trust, empathy, and a true relationship-first approach.

Leroy Nashke, real estate agent with Silver Shores Realty and a Senior Real Estate Specialist, shares how he helps 55+ clients downsize, transition, and make confident decisions. He discusses building trust, coordinating services, avoiding costly mistakes, and why personal service and integrity separate advisors from transactional agents.

Key Takeaways:

● Relationship-first real estate: Building trust and personal connections leads to better outcomes and stronger referral-driven growth.

● Serving the 55+ market: Senior transitions require empathy, coordination, and guidance beyond a typical real estate transaction.

● Acting as a trusted advisor: Providing honest advice, even when it slows a deal, builds long-term credibility and client confidence.

● Negotiation and teamwork matter: Collaborating with agents and managing expectations helps deals stay together.

● Specialization creates differentiation: Focusing on senior downsizing and transitions helps stand out in a crowded real estate market.

Connect with Leroy:

Website: https://www.silvershoresrealty.com

Connect with Mike Agol:

Website: https://www.ridgecapitalmanagement.com/