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finance
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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finance
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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Uncategorized
Identifying and Eliminating Wasted Ad Spend on Social Media Platforms
When I was an advertising manager for a $50,000/month client in 2019, I thought it was all good. Until I…
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Business
LLC vs. S Corporation Taxation for Digital Entrepreneurs: Which Minimizes Self-Employment Tax Legally
Two years ago while working from home, I received a tax bill I couldn’t believe! I was so excited about…
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Business
Investing Business Cash Reserves: Index Funds vs. Active Management for Short-Term Liquidity Needs
I remember sitting in my office back in 2016, staring at a bank statement that showed $200,000 in idle cash…
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finance
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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finance
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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Business
Using an ESOP as a Tax-Advantaged Succession Strategy for Closely-Held Businesses
I will never forget the time I sat down with a founder who had built his manufacturing business over thirty…
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finance
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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Business
A Practical Guide to Performing Your First SEO Audit on a Business Website
I recall when I was conducting an SEO audit for a customer for the very first time, I spent three…
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