You Gotta Pay to Play . . . Or Not

Last week, I wrote a post about the right of an investor to maintain their percentage ownership in a company through the pro rata rights provision often found in investment agreements. In that post, I referenced another provision that often crops up, pay-to-play. In its most basic form, the pay-to-play term causes an investor [...]

No Pro Rata Investment Rights?

I passed on an investment this week because the terms of the deal didn’t include the right for investors in the current round to maintain their percentage ownership in the company, through additional investment, in future rounds. This is usually outlined in the term sheet, in legalese, as “Preemptive Rights,” “Right of First Refusal” [...]

Starting Up on a Shoestring

A few weeks ago, I ran across a box full of photos I had taken a while back. Actually, they were color slides, which should give you some idea of how old they are. Many of them were of people, events and even documents (photos of documents? Don’t even ask, I can’t remember why) [...]

Does the Loudest Person You Hear Give the Best Advice?

I’m fortunate that I get to work with many startups, both independently and with TechStars where I’m a mentor.  There is no better way to learn than through teaching (learning is the most fun you can have, at least for a sustained period) and there are few better students than entrepreneurs.  Good entrepreneurs always [...]

TechStars Comes to Boston

Over the last few years, it has become increasingly difficult for Boston-based fledgling startups to get a leg up; to get, well . . . started.  It’s mind boggling, really.  There is so much talent and there are so many good ideas, it’s just been shocking to witness teams and ideas die on the [...]

Gun-Shy Venture Capital

Shawn Broderick over at Myriad Missives has a great post titled The Loser’s Curse that’s definitely worth a read for anyone pitching their deal to VCs.  Shawn refers to Fred Wilson’s post of the same name.

In his post, Shawn reflects on his failure to get venture capital for his last startup, Voxx.  Voxx [...]

Prepare and Be Prepared

Brad Feld has a great post this week titled, Don’t Be Casual, in which he talks about a company in his portfolio that did a “casual” presentation to a VC firm, only to realize that the company’s idea of casual didn’t match the VC firm’s.  In the end, “the meeting was a disaster.”  Brad [...]

Getting Chastised by an Investor

Several years ago, I was part of a team that did a slightly leveraged management buyout of a division of a larger company.  The deal was a relatively straightforward acquisition of all the assets, licenses, rights and so forth of the division for about $55M.  Roughly $35M came from a single VC fund.  Another [...]

Valuation Tipping Points

As a somewhat active angel investor, I’ve come to the conclusion that too many startups are looking for money too early in their development these days.  Perhaps this has always been the case, but it’s become more obvious to me in the last 6-12 months.  In the last month, alone, I have seen three [...]

Venture Capital Insights

Dharmesh Shah over on OnStartups has a terrific post titled 9 Pithy Insights on Venture Capital.  The post covers many of the key points that should be in the new entrepreneur’s handbook on getting venture capital.  I found myself nodding my head as I read each one. 

I’d add to the list (in [...]