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Posted on April 7, 2025 by Dan Pascone
Heart vs. Head: Should You Buy a Vacation Home or Investment Property in 2025?
TL;DR Answer Box A vacation home is primarily a lifestyle purchase (memories, convenience, identity), while an investment property is a business (cash flow, risk, management). The right choice comes down to (1) your goals (joy vs. return), (2) your financial foundation (emergency fund + retirement on track), and (3) whether the numbers work after all […]
Posted on April 4, 2025 by Dan Pascone
DIY vs. Financial Advisor: Which Wealth Strategy Works for You in 2025?
TL;DR Answer Box You don’t need to have all the answers—but you do need the right system. If your finances are simple and you’re motivated to learn, DIY can work well. If you have complexity (equity comp, multiple goals, taxes, business income, major life events), a good advisor can pay for themselves through behavior coaching, […]
Posted on March 31, 2025 by Dan Pascone
Why Hybrid Living Beats Full Retirement
TL;DR Answer Box Hybrid retirement is a modern retirement transition where you reduce mandatory work while keeping optional income (consulting, fractional roles, boards, passion projects). The goal isn’t a “magic number”—it’s financial clarity: know your burn rate, diversify income, and use lower-income years for tax wins (like Roth conversions). Test it with a mini-retirement before […]
Posted on March 27, 2025 by Dan Pascone
Crush the Rest of 2025: A Smarter, Sharper Portfolio Starts Now
TL;DR Answer Box If your portfolio has drifted onto autopilot, 2025 is the year to realign it. The highest-impact moves are simple: (1) assign every dollar a job, (2) optimize asset location for taxes, (3) stress-test risk before the market does it for you, (4) consolidate and cut fee/overlap drag, and (5) rebalance with a […]
Posted on March 24, 2025 by Dan Pascone
Start Smart, Stop Sabotage: The 2025 Wealth-Building Playbook
TL;DR Answer Box If you want to strengthen your finances in 2025, focus on four “start” moves—automate investing, diversify tax buckets, eliminate high-interest debt, and capture every dollar of your 401(k) match. Then cut four “stop” habits—excess cash drag, high-fee funds, trend chasing, and ignoring estate planning. Small changes here can produce outsized results over […]
Posted on March 21, 2025 by Dan Pascone
Smarter Prompts, Smarter Money: How ChatGPT and AI Can Assist Your Finances
TL;DR Answer Box ChatGPT can be a powerful personal finance “copilot” for budgeting, investment research, and brainstorming tax-saving ideas—if you give it clear context and treat its output as a starting point, not final advice. The biggest wins come from better prompts, structured checklists, and using AI to reduce friction (analysis, summaries, planning). The biggest […]
Posted on March 11, 2025 by Dan Pascone
Financial Planning for Go to Market Leaders and Sales Professionals
TL;DR Answer Box Equity can create life-changing wealth for GTM leaders—but it’s rarely a “quick win.” Taxes (especially on NSOs), vesting schedules, and option expiration deadlines can quietly destroy outcomes. The bigger threat? Behavioral traps like recency bias and social proof from negative stories that cause employees to undervalue or mishandle their equity. The solution […]
Posted on March 7, 2025 by Dan Pascone
Finding a Financial Planner Who Saves and Makes You More Than They Cost
TL;DR Answer Box The right financial planner acts like a personal CFO—aligning your equity comp, taxes, portfolio, and long-term goals into one cohesive system. Don’t hire based on credentials or marketing. Instead, get clear on what you need, then vet planners with questions they can’t dodge: real examples, specific processes, and measurable value beyond “market […]
Posted on March 4, 2025 by Dan Pascone
Life After the Big Payout: Wealth Preservation and Growth Strategies
TL;DR Answer Box A liquidity event can change your life—if you handle the first 90 days correctly. Before upgrading your lifestyle, stabilize cash, estimate taxes, eliminate toxic debt, and build a rules-based plan for diversification. Then invest across tax “buckets” (taxable, tax-deferred, tax-free) and use advanced tools like Roth conversion ladders, insurance-based strategies (LIRPs), and […]
Posted on October 28, 2024 by Dan Pascone
Play Defense, Build Legacy: Wealth Protection Strategies for High Earners
TL;DR Answer Box Building wealth is only half the battle. High earners face bigger and more complex risks: lawsuits, health surprises, market volatility, and changing tax laws. The defense is a two-part system: (1) risk management (insurance, liquidity, liability protection) to protect your lifestyle while you’re alive, and (2) estate planning (wills, beneficiary audits, trusts, […]