Tag Archives: Greybull Stewardship

Raising Capital: About Fit and Timing

I was in New York last week speaking with existing and prospective investors in my investment fund, Greybull Stewardship.  The match-making activity between capital seeking returns and opportunities seeking capital is truly amazing in the United States.  Nothing brings this home like New York City… Continue reading

Company Culture Like Fine Wine or Great Coffee

Company culture gets crafted over time by thousands of small decisions, and a few large ones. Yes, the big decisions about the vineyard or varietal takes spectacular time. But I was struck by how many small decisions like the shape of wood barrel, the wood… Continue reading

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

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

BCG Growth Share Matrix of Cash Cows, Dogs, and Stars

Older ideas, seen anew, can be helpful to business owners.  In that spirit, I have highlighted Economies of Scale and Michael Porter’s Five Forces previously.  Today, I highlight another older idea in the Boston Consulting Group (BCG) Growth Share Matrix that was developed by the global consulting… 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