The Long Game

Blake McKibben, estate-planning attorney who helps advisors and clients with trusts and probate avoidance. He digs into why many trusts fail to work, what retitling assets really means, and the pitfalls of relying on pour-over wills. Short practical digests on deeds, insurance, vehicles, business shares, and beneficiary coordination.

Clear signs of financial health include having a real plan and knowing your cash flow. The conversation covers savings rate, layered liquidity, and avoiding high-interest debt. It highlights proper insurance, estate planning, and a steady investment approach. Emotional cues like portfolio obsession and money anxiety are also explored.

A step-by-step walkthrough of an annual financial review, from checking net worth to analyzing cash flow and spending. Learn how to set and map this year’s goals, project take-home pay, and build a cashflow plan. Tips on automating allocations, handling irregular income, rebalancing investments, and reviewing insurance and estate essentials.

Brent Sullivan, a tax and investment strategist focused on capital gains and ETF/deferred-tax techniques. He explains 351 exchanges as a little-known tax-deferral tool for concentrated stock positions. Short talks cover using ETFs to convert holdings in kind, sponsor rules and diversification tests, operational mechanics and IRS scrutiny, and alternative tools like collars and prepaid forwards.

Ben Lake, CFA® and CFP®, a wealth and estate planner, explains Irrevocable Life Insurance Trusts (ILITs) for high-net-worth families. He covers why liquidity matters for estate taxes. He outlines how ILITs keep death benefits out of taxable estates. He compares policy types, funding methods, and who most benefits from ILITs.

David Barnett, an experienced business buyer, seller, and advisor, shares hard-earned lessons from dozens of small-company deals. He contrasts buying versus building, warns about overpaying and bad deal structure, and explains what makes acquisitions work: the right industry fit, realistic financing, and systematizable operations. Practical cautions about licenses, seller behaviors, and partner dynamics keep things grounded.

Ben Lake, CFA, CFP, a financial professional experienced in private equity, real estate, and credit. He walks through what private equity, private real estate, and private credit are. He explains timelines, liquidity and lockups. He outlines who might qualify and why vetting and tax, liquidity, and planning matter.

Brent Sullivan, a tax and wealth planning pro for high-net-worth clients and organizer of Basis Northwest, breaks down long-short direct indexing. He explains how it differs from long-only strategies. The conversation covers tax-loss harvesting stories, financing and margin mechanics, who benefits most, and the operational and jurisdictional risks to watch.

Ben Lake, a financial professional who advises high-net-worth households on liquidity and tax-efficient borrowing. He walks through sudden cash needs, when to sell taxable assets or RSUs, HELOCs versus cash-out refinancing, margin loans and pledged-asset lines, and the rising use of box spread loans for tax-savvy borrowing.

Tax expert Ryan Dolan shares essential tips for smooth tax prep! He emphasizes the importance of hiring a consistent tax team for accuracy and continuity. Ryan advises starting document organization early and using a dashboard to keep track of finances. He explains the common pitfalls like confusing balance payments with estimated payments. Plus, the benefits of extensions are discussed, especially for those awaiting certain documents. Get ready to take charge of your taxes and avoid last-minute stress!