Seven Surprises About Convertible Notes That Founders Should Know

Over the past two years, there has been an explosion of the use of convertible notes for seed rounds. It used to be these debt instruments that convert to equity later at a discount to the price of the next round were only for small initial financings of, say, $250,000 for a company to get … Continue reading “Seven Surprises About Convertible Notes That Founders Should Know”

Five Ways To Avoid Losing Money as An Angel Investor

I have an angel investor friend—let’s call this friend “Alex.” Alex has great deal flow and works hard to pick the best opportunities for investment. Alex has been frustrated over the past several years, however, because she doesn’t seem to be making any money. This is despite solid operational performance by several of the companies … Continue reading “Five Ways To Avoid Losing Money as An Angel Investor”

Reinventing the Board Part III: The Agenda

CEOs, investors, and board members frequently complain about ineffective board meetings. Steve Blank, Jeff Bussgang, Brad Feld, and Fred Wilson each have suggested board meetings could be improved by changing the format, process, or content. Having good meetings starts by having the right people in the room (as discussed in the first installment of this … Continue reading “Reinventing the Board Part III: The Agenda”

Reinventing the Board Part II: The Role of the Chair in Increasing Board Effectiveness

Technology companies’ boards of directors need better leadership. I made a case last month about reinventing the board of directors by treating the board as a team and doing annual assessments against company needs. Boards that are structurally more aligned with their company’s operations are better able to help them achieve success-or at least reduce … Continue reading “Reinventing the Board Part II: The Role of the Chair in Increasing Board Effectiveness”

Reinventing the Board

Imagine a world where technology companies are more successful and grow faster because of the strategic help and guidance from their boards of directors. Or, at least imagine a world where they don’t suffer from unhelpful, or worse, problematic boards that consume management’s precious time. Some commentators like Steve Blank, Jeff Bussgang, Brad Feld, and … Continue reading “Reinventing the Board”

New York City and Boston: The Entrepreneurial Dream Team

Far too much has been written about Boston versus New York City. Sports rivalries and cultural differences have a way of coloring our world view to include startup companies and venture capital. However, the past few years tell about a much closer relationship. The real story is Boston and New York City, particularly versus Silicon … Continue reading “New York City and Boston: The Entrepreneurial Dream Team”

Dodd Bill Update: Listening to the Market

Like an entrepreneur listening to market feedback while designing a product, Senator Christopher Dodd (D-Conn) has made some improvements to features of his pending legislation that we described last month. Originally designed to fight the “too big to fail” problem in the financial markets, many constituents—including the Angel Capital Association and the National Venture Capital … Continue reading “Dodd Bill Update: Listening to the Market”

Dodd Bill Could Render Startups Too Small to Succeed

Senator Christopher Dodd (D-Conn) recently introduced sweeping legislation that aims to rein in the excesses that led large financial institutions to become “too big to fail.” Somewhat ironically, it also has the potential, as one commentator put it, to make startups “too small to succeed.” In the rush to prevent future problems, we risk taking … Continue reading “Dodd Bill Could Render Startups Too Small to Succeed”

It’s Time to Start Networking for Real

While Scott Kirsner and my fellow Xconomist Tim Rowe both recently have commented on the benefits of mixing and mingling in Kendall Square, we have a more basic problem that won’t be solved by just rubbing shoulders. Chalk it up to Yankee stoicism; our long, dark winter; or our independent sectors of software, communications, medical … Continue reading “It’s Time to Start Networking for Real”

“Thank You For Supporting Capitalism” and Other Investor Tales of Two Cities

Two weeks ago, I was in Atlanta for the annual Angel Capital Association (ACA) conference and, this past week, here in Boston for the annual National Venture Capital Association conference. Depending on whom you asked at both conferences, it was the best of times or the worst of times, most likely depending on whether or … Continue reading ““Thank You For Supporting Capitalism” and Other Investor Tales of Two Cities”

Three Ways (Times Three) for Entrepreneurs to Blow It

Nobody likes to fail. No entrepreneur or venture capitalist thinks a particular venture is going to be the one to fail. As veteran venture capitalist Bob Crowley at the Massachusetts Technology Development Corporation says, “we’ve never made a bad investment; just investments that have gone bad.” If we as investors or entrepreneurs thought the odds … Continue reading “Three Ways (Times Three) for Entrepreneurs to Blow It”

The Economic Shock to Venture Investing—Lessons Every Entrepreneur Should Know

Over the past several years, and especially since this summer when CommonAngels (where I serve as managing director) became the first angel group to join the National Venture Capital Association (NVCA), I’ve frequently been asked in varying tones of voice from the curious to the cynical, “Is CommonAngels an angel group or a venture capital … Continue reading “The Economic Shock to Venture Investing—Lessons Every Entrepreneur Should Know”