Handling a “No”

I’ve spent a considerable amount of time playing angel investor over the years which has given me the chance to meet many great entrepreneurs. In general, when an entrepreneur contacts me, he/she is looking for money, advice or both. Generally speaking, I make a quick determination if the people are some that I might [...]

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” [...]

Who Should I Hire?

I’ll take a great team over a great idea in business any day of the week (of course, having both is even better). Why is that? Because ideas are often fleeting – markets change, technology evolves, competition is a moving target and customers are, sometimes, fickle. Great teams can adapt and continually innovate. Great [...]

How Much Should I Look for in My Seed Round?

I often run across early stage companies in a real quandary about how much money to take in their first round of funding. That is, the round just beyond the Ramen noodle eating, avoid starvation round that is usually funded out of your own pocket. The round that really gets things going once you’ve [...]

Angel Investing

After yesterday’s phenomenal Angel Boot Camp in Cambridge (MA), I’ve been thinking about a long overdue post on the topic. I did my first angel investment in 1994 and I’m now in the process of wrapping up my 31st (individually, that is, not as part of a fund) – it’s also my third in [...]

Every Company Needs a Board of Directors – Startups Too

OK, maybe not every company. Raw startups – two people in a garage kinda thing – shouldn’t waste their time with anything formal. But young companies – those that are established and on their way, regardless of their size or level of funding should, as should any company more established than that. It seems [...]

Build Platforms on Platforms

Being a software guy myself, I often find that I dig a little deeper into the successes and failures of the software-oriented startups that I work with than I do with the non-software oriented ones.  When I do, I suppose that I shouldn’t be surprised, although I routinely am, at how often I come [...]

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 [...]

No. Don’t Do It. The Co-CEO Thing Won’t Work

I’ve been getting involved with more raw startups lately and I’m being reminded daily about the difficulty many teams have in establishing any form of decision-making hierarchy.  “We’re equal partners in this enterprise.”  “We started it together, we’re going to run it together.”  “We both [all] provide equal value so should have equal input.”  [...]