Lessons Learned

Video: Hanging out with Jennifer Fremont-Smith of Smarterer

Smarterer is a consumer web startup funded by Google Ventures and local angel investors:  Dharmesh Shah, Joe Caruso, & Nicole Stata.  Smarterer's goal is to...

How to Kill Start-up Distractions

Start-ups are hard, but there are a few things that you can do to make your life simpler and give your start-up a better chance of success.  These are lessons I’ve picked up along the way...

SaaS CEOs: Measure Customer Engagement - Increase Conversions & Lower Churn

The goal of a SaaS CEO should be to increase the profit they make from each customer (LTV), and lower the costs in sales and marketing that it takes to acquire each customer (CAC). Measuring Customer Engagement is a key tool...

Business Model Analysis, Part 10: Getting Started
This post is part of a series on business model analysis for entrepreneurs. The first post in the series presents a comprehensive list (available as a downloadable PDF) of issues entrepreneurs should...
A New Generation of Opportunity @ MIT
Is MIT finally starting to catch up to its west coast counterparts in undergraduate entrepreneurship? After attending this weekend’s t=0 entrepreneurship festival, it definitely appears so. The t=0...
Business Model Analysis, Part 9: Outsourcing
This post is part of a series on business model analysis for entrepreneurs. The first post in the series presents a comprehensive list of issues (available as a downloadable PDF) entrepreneurs...
Business Model Analysis, Part 8: Crossing the Chasm
This post is part of a series on business model analysis for entrepreneurs. The first post in the series presents a comprehensive list of issues (available as a downloadable PDF) entrepreneurs...
“Strategic” customers are a myth.
Lots of small companies will do anything to sign up a big customer. Startups often make concessions of two varieties: We’ll give you more stuff (read: features / support). You give us...
So you want to be an entrepreneur, eh?
This blog post is for people recently admitted into a MBA program who want to start a company post graduation. While there are many great blogs out there to help entrepreneurs and early-stage...
BUILD Gathers Boston's Best to Mentor High School Entrepreneurs
BUILD Greater Boston is gathering a select group of entrepreneurs and professionals from many fields to mentor student business teams in some of Boston’s lowest performing high schools...
Business Model Analysis, Part 7: Bundling
This post is part of a series on business model analysis for entrepreneurs. The first post in the series presents a comprehensive list of issues (available as a downloadable PDF) entrepreneurs...
The Process is not the Point
There are two parts to every project…the Process and the Point. The Process, which gets most of the attention, is the series of steps we go through to do the work. We obsess over the process...
Engineers aren't from Mars
Recruiting is hard. Finding the best talent is never easy—especially when it comes to finding a rockstar engineer. But could it be that companies simply don’t understand what engineers want? As an...
Taking the Long View as the Value-add Investor
A few weeks back, Eric Ries issued a stark warning for the start-up community: Winter is coming, and it will be long and hard, and there will be a lot of casualties from the unsuspecting crop...
Five takeaways from folding a startup
A couple of months ago, after lots of introspection and sleepless nights, we decided to put Grinnit on a permanent hiatus. We thought the best way to seek closure would be to share our story...
Lessons from the Lean Startup Challenge
I started using lean before joining the Lean Startup Challenge so I wasn’t expecting to learn too much from the competition, but, even so, I learned more about my startup in the first...
Rules for an Effective Business Plan
The written business plan is often the first contact an entrepreneur has with the investment community. It presents the company on paper before the company can represent itself and...
How to Hire a Good Marketer (for Startups)
It’s the question I hear second-most often, right after “How do I hire a good developer?”. Marketing is one of those skills a startup can’t do without, and realistically, probably shouldn’t...
Business Model Analysis, Part 5: Virality
This post is part of a series on business model analysis for entrepreneurs. The first post in the series presents a comprehensive list of issues (available as a downloadable PDF) entrepreneurs...
How Boston Can Step Up Our Game (hint: we are so close!)
It wasn’t too long ago that the Boston startup scene seemed to be panicking a bit. Lots of discussions started to form around how to step up our game and get our groove back. There were talks...
What milestones are needed to raise a Series A?
For entrepreneurs seeking to build big companies on a rapid trajectory, raising larger scale venture capital rounds is likely a necessity at some point after the initial seed funding...
False Market Signals
How do you figure out if there’s a market for your product? This is one of the hardest questions to answer and arguably, the most important. When we started Handshake.com in 1999...
StyleFeeder - A "lean" success story
Philip Jacob wrote an interesting blog post recently called StyleFeeder: a retrospective. Philip was...
Recruiting as a Strategic Weapon
Many people talk about the importance of recruiting in building a startup. What most people mean by that is that attracting and retaining key talent is incredibly valuable. Here at RunKeeper...
Interview to Venture: Episode 2, Bit9

Last time on interview to venture, I sat down with Boris Revsin, co-founder & CEO of CampusLIVE. Boris is a first-time CEO in his 20′s and is building a consumer internet company that is...

All the bad things VCs want to do to you (video)
Richard Dale of Sigma Partners recently gave a talk to the MassChallenge participants called: All the bad things VCs want to do to you! Below is a video that captured a Q&A session from the event...
The blue pill or red pill: Start-up life or an MBA?
I’m a movie guy. In one of my favorite movies, The Matrix, there is a famous scene as many know where Keenu Reeves’ character Neo is offered a choice between a blue pill and a red pill by Laurence Fishburne’s...
Founder Dialogues featuring Andy Ory of Acme Packet (Video)
In the past, Boston has never been good at celebrating the many, many great success stories in our backyard. Maybe we're too humble? However, over the past couple of years, the tide has turned...
Leaving money on the table
I spend a lot of my time recruiting the best people I can find to join our portfolio companies. These days one subject comes up frequently - namely, “leaving money on the table." Some of the..
Five Tips for Non-Toxic Networking
People tell me I am a power networker. I don’t see myself that way at all. I secretly prefer a book to a conference, any day. However, when at a business event I make the most...