finance
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Resolving a Surprise Tax Bill After Underpaying Quarterly Estimated Payments
The great news is that you are not the only person who has gone through this! When I discovered how…
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Debt Financing vs. Equity Financing for Scaling Businesses: A Risk-Adjusted Decision Framework
In 2014, I was sitting in a small office space at my startup, looking at a term sheet that would…
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Structuring Key Person Insurance and Buy-Sell Agreements to Secure Partnership Continuity
I’ve been in meetings before where two partners were discovering together that they essentially don’t have a written partnership agreement!…
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Tax-Loss Harvesting Beyond Equities: Applying Strategies to Crypto, Bonds, and Real Estate Crowdfunding
I will never forget the moment when I sat down in my office in 2018, looking down at my portfolio,…
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Solo 401(k) vs. SEP IRA: Choosing the Optimal Retirement Plan for a High-Income Solo Entrepreneur
Five years ago, I was still standing in my office. Everything was great; I had just finished my best year…
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Offshore Banking and Multi-Currency Cash Management for Global Entrepreneurs: A Compliance-First Framework
It was an “ah-ha” moment I had while working in a cramped little office in Singapore over a spreadsheet that…
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Analyzing the Federal Reserve’s May 2026 Decision: The March Inflation Slip and the Rate Cut Timeline
Problem: Currently, due to the Federal Reserve pivoting and the March 2026 unexpected inflation, many small business owners and investors…
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The June 1, 2026, US Debt Ceiling Deadline: What the Treasury’s Latest Extraordinary Measures Mean
The Treasury must continue meeting its obligations for an indeterminate period before its cash balance runs out (referred to as…
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Decoding the Bipartisan Tax Framework’s Revival and the Fate of the 2017 Individual Tax Cuts
Going back to 2017, I sat in a large conference room with everyone popping champagne after the Tax Cuts and…
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The Commercial Real Estate Refinance Wall: Analysis of the 2026 Office Sector Maturity Schedule
I recall sitting in a boardroom back in 2010, and a portfolio manager being very nervous about an approaching maturity…
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