Tag Archives: Taxes

Portfolio Churn — Enemy of Investment Returns

Churn destroys investment return.  Strangely, traditional private equity builds itself to churn.  Churn reduces investment returns for several reasons such as transaction costs, business disruption, and the difference in tax rates between ordinary income and capital gains.  This last difference is the easiest to quantify as… Continue reading

Asset Sale Versus Stock Sale (Purchase & Sale Agreements – a series)

Asset Sale = LLC and S Corporation If you are a business owner considering the sale of your business, please put yourself in a position for an asset sale rather than a stock sale by holding your business in a Limited Liability Company (LLC) or… Continue reading

Business Purchase and Sale Agreements (a series)

This post begins a series of posts on business Purchase and Sale Agreements.  Even though I have executed a number of  Business Purchase and Sale Agreements in my investing career, this series falls in the category of “teaching what you want to learn” as I… Continue reading

Enlightenment about Investor Alignment

Obtaining alignment among the various parts of a company, particularly between company founders and investors, is a never-ending topic.  Two items have caught my eye this month that relate to this issue and may help spread some enlightened thinking about investor alignment. First, Fred Wilson, a… Continue reading

Construct a Perfect Business, Financially Speaking

Designing the financial model (in a real-world sense, not a spreadsheet sense) of your business is worth every minute that you can dedicate to it. We should craft the financial model of our business with as much care as a fine architect and craftsman would… Continue reading

To Sell Your Business or Not To Sell Your Business — That is the Question (a series)

Should you sell your business? This is one of the most difficult questions and there is no one right answer. I have been asked this question so many times and it is the most difficult to answer. To provide some assistance on the question, however,… Continue reading

C Corporation Business Owners are at Risk of Losing Millions

I lost huge money early in my career in not electing to switch my company from a Corporation to an S Corporation.  I don’t want you to make the same mistake.  Each year, the owners of C Corporations have an opportunity to switch their tax… Continue reading

Tax-Free Entities Supported by Greybull Stewardship

Are you still paying two-levels of tax on the income from your business? If your company is a profitable, cash-generating business, it is a large advantage to be organized as a flow-through entity for tax purposes (S Corporation or Limited Liability Company). As most of… Continue reading