Series on Trust: Partners and (or vs.) Non-Partners
This is the fifth and last blog post in a series on trust. I’ve written
in the past about trust between a VC and an entrepreneur (“When Entrepreneurs and VCs Break Up”), between...
Series on Trust: When VCs Divorce
This is the fourth post in a blog series on trust. I previously wrote
about how trust is critical in the VC-entrepreneur relationship (“When Entrepreneurs and...
Scaling is Hard, Case Study: TripAdvisor
TripAdvisor may be one of the most fascinating companies I know and so I
was excited to dig into their business model as part of my series on
scaling. This is a company that took $4 million...
Scaling is Hard, Case Study: Akamai
I have been thinking lately about how hard it is to scale start-ups.
The Lean Start-Up movement, as exemplified in Eric Ries' book The Lean
Start-Up, has appropriately focused a great deal...
Series on Trust: The LP and the VC
This is the second post in a blog series on trust. Last week, I wrote that VC is a “trust business” and I highlighted
why trust between an entrepreneur and a VC is important...
Customer References: Why Investors Need Them and How to Make Sharing Them Less Painful
So you’ve decided to raise capital and have figured out what your ideal partner would look like – great! If you’re still toying with theidea of raising or trying to figure out...
Founders: Are You Stuck Before You Start?
Between us, my long-time friend (and fellow blogger) Andy Palmer and
I have started a lot of companies. We also advise many other companies
and look at even more pitches from...
Can a Growing Company Grow Faster While Spending Less? (Part 2)
In Part 1 of this post,
I laid out a portfolio company case study that lays out the
considerations a CEO should take into account when deciding between
capital efficiency and revenue...
The Biggest Problem Facing Consumer Web Companies in Boston
A lot of ink has been spilled about the challenges of building large scale consumer internet companies in Boston. Here’s a recent example that is quite thoughtful although misses...
Can a Growing Company Grow Faster While Spending Less? (Part 1)
A lot of growing businesses face a common issue as they advance past the early stages of their development: How can they accelerate growth while concurrently improving
To Leave or Not to Leave as Your Startup Grows
A few weeks ago, a very good friend who works at a growing startup
emailed me with the following question (in which I’ve masked just a few
of the identifying details)...
To Start a Company, Start with a Good Idea
I hang out in a university where new ideas are everywhere. In fact, the
product of the CSAIL lab at M.I.T. is arguably new ideas. I am asked
routinely “What constitutes...
Why Innovation Needs Design Thinkers
Instagram created a better way for people to share photographs. Their innovation was worth $1B to Facebook (even without revenue). Why couldn’t Facebook...
Boards and Advisory Boards: Different Animals
New entrepreneurs show a lot of confusion on the subject of advisory
boards and corporate boards of directors. It’s justified; there is some
conceptual overlap. But they...
Why Churn is SO critical to success in SaaS
Summary: Illustrates graphically why churn is a huge problem a SaaS
company gets larger. It also looks at a very surprising factor that can
massively accelerate SaaS...
Why Product Management Should Be Its Own Department
In my 15+ years in technology I have had the privilege of working as a
product manager who reported to various department heads. In some cases I
reported to engineering...
Think Twice Before Starting a Company
I sent a tweet out last week that resulted in some healthy debate: “three years ago, I was telling everyone I met to start companies. These days, I’m telling everyone to think twice...
How Collaborative is Your Approach to Selling?
I read a fascinating article in the Harvard Business Review about teamwork. One of the sentences that caught my eye was this, “Team members are more likely to want to...
Why One of Your Board Meeting Goals Should Be Addressing the Elephant in the Room
When you look up the phrase “the elephant in the room” in Wikipedia you get: “Elephant in the room” is an English metaphorical idiom for an obvious truth that is being...
The case for an early exit: Average price increases between rounds
I have long had a theory that (for companies with up rounds) the
greatest valuation increases occurs between the A and B rounds. So, I
recently had opportunity to do some...
On Selling Your Company
The most important financial decision you will ever make as an
entrepreneur is when to sell your company. What amount of money to
raise at what price from whom pales in comparison...
I could build Instagram in a week
could build Instagram in a week. How many times have you heard someone
say "I could build [insert hot startup name here] in a week"? I hear it
all the time. But, I have yet...
Tools to Launch Your Startup on a Shoestring (Part 3)
This is the final part in a three part series about how to launch your
startup on a shoestring budget. In the first post, we looked at back
office and operational tools that enable...
Simple (yet important) tips to make a great first impression
Without dating myself or even just admitting I like classic rock and folk music, one of the best stories told through a song is “Cat’s in the Cradle” by Harry Chapin. For those of you...
7 Lessons Entrepreneurs Can Learn from Teachers & Students
students have a mutual goal: to learn. The best teachers constantly adapt their
plans - sometimes at a moment's notice - to ensure that they meet the needs...
Four Keys to Innovation and Growth
What can we learn about innovation and growth from the most successful growth companies? Global competition and a weak economy have made growth more challenging...
Startup Mentoring: a delicate balance of creative destruction
I have been involved in many environments in which
mentoring is a core part of the value proposition. Seedcamp or TechStars succeed almost
exclusively on the quality of their...
5 Things You Need to Forget When You Join a Startup
A couple of months ago Mark Stephens wrote a guest post on
OnStartups about the benefits of gaining experience at a large company.
Having worked at a large company, and having...
Mentor Like You Mean it
There’s something magical happening in Boston right now, and
it’s going to make history. Like many
Startup scenes, Boston’s is truly exploding, vibrant with...
Things Entrepreneurs Never Confess To Their VCs
Note: This is intended be a light-hearted piece that hits just close enough on some counts to (hopefully) be funny. Please don't take it too seriously. (Oh, and for the record, I've actually...