Category: Business Financing & Funding

Announcing Increased Investment in Appointment Plus — leading appointment scheduling software

Greybull Stewardship, my investment fund, is excited to announce that we have invested more capital into Appointment Plus, the leading business automation software specializing in appointment scheduling. By doing so, Greybull Stewardship has increased its ownership percentage in a growing company that plays an important… Continue reading

“VC Bargain”: Capital in Exchange for the ‘Duty to Sell Company’

A post this summer from Jason Mendelson of the Foundry Group really caught my eye.  It is about the explicit “VC Bargain” that an entrepreneur makes when taking an investment from a venture capital firm.  Basically, the VC fund will need the founders to commit… Continue reading

Phantom Stock, Shadow Stock, or Virtual Stock — Employee Ownership (a series)

An employee who “thinks like an owner” is the Holy Grail — having employees for owners — as we have discussed in other posts.  Therefore, I have been writing a series of posts about tools that owners can use to assist employees to think like… Continue reading

Joys of Ice Cream, Apple Pie, and Recurring Revenue

Charlie Munger, Vice Chairman of Berkshire Hathaway, once told a friend of mine that if Charlie were a young man, he would be “trying to find online recurring revenue businesses” — like many that are being built and growing today. The combination of recurring revenue… Continue reading

Business Buyers According to Warren Buffett: Competitors, Flippers, or Berkshire Hathaway!

Whether to sell a business or accept outside equity capital is a high stakes decision for business owners.  Trade-offs are natural and necessary — we instinctively know that we cannot achieve every objective in every decision.  It is pretty easy to categorize the business buyers… Continue reading

New Twist on Venture Capital with Better Risk-Adjusted Investment Returns

A higher return investment can have a broad distribution of potential outcomes, as conveyed by this graph from Howard Marks of Oaktree Capital Management (the graph is from his book The Most Important Things Illuminated). This graph is a more helpful way to understand risk… Continue reading

Built to Last or Built to Flip?

Is your business built to last or built to flip?  No question influences your business strategy more than this one.  There is no right answer — either strategy is fine.  However, making sure that you have alignment throughout your organization on this question is very… Continue reading

Real Estate Institute Acquired by Greybull Stewardship

Greybull Stewardship, my long-term oriented partnership of business owners investing in exceptional small businesses, announces the acquisition of Real Estate Institute and its sister company, Bookmark Education.  Both companies are headquartered in Niles, IL, which neighbors Chicago. Since 1992, Real Estate Institute has been a… Continue reading

Unique Businesses Are A Force For Good

The best businesses are not just about making money.  It is necessary to make money to stay in business, but it is not sufficient for the business to be worth your time.  That is why the strongest businesses, in my opinion, are the ones that… Continue reading

Investment Strategy & Structure Is the #1 Thing Founders and CEO’s Should Watch In Raising Capital

To be better, one must first be different.  Thus, good strategy focuses on understanding differences and creating differences.  This also applies to investment firms — differences in structure often drives the strategy.  Any entrepreneur or business owner considering raising capital needs to understand the structure… Continue reading