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Two Must-Join Networking Groups for New or Aspiring Boston Entrepreneurs
About a year ago I left Terrafugia and launched myself solo into Boston’s entrepreneurship scene. The advice given to me by a distant mentor was “find some local entrepreneurship resources and get involved.” I started by Googling. I was amazed by how much exists in Boston. Two groups in particular have earned a lot of […]
Landlords Pay No Taxes?
I’ve been writing a bit about technology startups lately. Let me flip back to the other end of the business spectrum — landlording — to share an interesting conversation I overheard recently: Landlord One: How many landlords pay taxes on their rental income? It’s like no one. Everyone runs at a loss. Landlord Two: Oh, […]
Why I Wouldn’t Bet the Farm
How many times have you heard an entrepreneurial success story where the founder took huge risks and won big? It usually goes like this: they took out a home equity loan, maxed out their credit cards, and pitched violently forward into the ditch of debt only to be saved at the last minute by a […]
The Surprising Math Behind Startup Dilution
This recently blew my mind, so I thought I’d share some simple math with you. Imagine an investor wants to invest in your startup. He says it’s worth $1 million and he wants to invest $500,000. He’s going to take half your company, right? Wrong. He’s going to take one third. At least, that’s the […]
How to Count in Sklansky Dollars
Here’s a neat concept that everyone can use, from professional poker players to Warren Buffett. In Alice Schroeder’s biography, The Snowball, she describes how in his youth, Warren was good at assigning odds to each horse in a race. This is called “handicapping.” Schroeder uses this as an analogy to explain how Buffett calculates investment probabilities. It’s […]
How NOT to treat your employees
A company I’ve done some work for in the past recently lost a major bid. The super-boss called the entire team into a conference room and said, “You lost the bid, you’re all fired.” Some of the team had been with the company for over thirty years. The carnage hit multiple rungs of the ladder, […]
How much is my startup worth?
This is the question for any startup looking to measure their personal wealth creation, take on additional capital, or sell their business. Unfortunately, the answer is usually, “Somewhere between nothing and a whole lot.” You can do better. Working Backwards: Step One Think about what your business is going to look like when it’s big […]
Financial Figuring for Landlords: Working Capital
What will you do if that old roof floods your top floor apartment, or if a cast iron drain pipe cracks just as you’re paying for bedbug extermination? What if the jobs cost $10,000? Do you call up your regular contractor and cut a check without batting an eyelash, or is this is a crisis […]
Miracle on 1st Street SE
Imagine that you are the proud manager of the only company that provides food to the people who live in a large area around your plant. Your CFO comes to you for the quarterly update and for the first time in a long time it’s good news. He shows you the graph below: “We haven’t […]

