Lessons Learned

The Bowdoin to Boston Tech Trek

I was reading in Xconomy yesterday the Taylor Yates description of his trek to Silicon Valley with his MIT Sloan classmates and I couldn’t resist sharing with the Boston community...

Tips from Boston Investors for Securing Early Round Funding and Achieving Startup Success

Last month, IDEA: Northeastern’s Venture Accelerator hosted Investor Insights, a biannual event featuring a panel of venture capitalists and angel investors. The forum provides...

Founder Dialogues IX featuring Dharmesh Shah of HubSpot [video]

Has there been any other company in the Boston area that has created more buzz than HubSpot over the past few years???  Dharmesh Shah was the latest guest for Eric Paley's...

HubSpot’s Dharmesh Shah Shares Ups and Downs of Startup Life

Last night, in the ninth installment of the Founder Dialogues series, Dharmesh Shah, co-founder and CTO of Cambridge-based SaaS company HubSpot, recounted his entrepreneurial journey...

Pricing is a Process and How We Validated Our Technology By Pricing Gold

One of the biggest lessons we’ve learned within the world of pricing is that even though your price remains the lever that has the highest impact on your revenue, the subject is one...

What Do You Suck At?

One of the truisms of entrepreneurial startups is the importance of focus. Starting a company to compete against huge, well-capitalized companies is daunting enough. So focus...

4 Startup CEO’s Motivational Moments For Any Occasion

As a typical startup founder I am often faced with difficult situations. Well, “often” is probably an understatement.  ”Always” is more like it.    As Steve Blank said in his Customer Development...

RxApps Uses Texting, Other Tech to Track Mental Health

Watching friends and family members undergo treatment for psychiatric conditions inspired John Moore to create RxApps, a health management platform...

Spend More Time on Your Mission - The Money Will Follow

Time – and how you use it – is the most important consideration for a Founder.  This is one of the most important lessons I’ve learned in my 20 years as an early...

Zero to Sixty in 6.1 Weeks

Now that we’ve wrapped up the inaugural session of the Boston Startup School and prepare for our next class, I thought I’d take a minute to reflect and share some...

Paper Money: Personal finance for entrepreneurs

In 1999, my internet start-up was valued at nearly $100M. I thought I had it made. Like many of my contemporaries at the time, I rented a nice apartment near the beach...

Post-Seed Funding Checklist for Founder/CEOs

You’ve just closed your seed round.  Other than starting to build, hire, and take over the world, there are a bunch of mundane things to do right away.  The following is a...

Scaling is Hard, Case Study: athenahealth

There are many companies that are competing to be the “operating system” for small businesses. The theory is that with the advent of the cloud in the digital age, small businesses...

Leaders: Ask Your Team This One Simple Question

Recently, on my way to work, I wrote our team at BuySellAds the following email: Tomorrow, I want each person to email me, privately, 1 thing that I can do to make their...

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...

Lessons from HubSpot: 10 Keys to Ensure Success for Growing Companies & for Sales People

I had to write this post right away, before I forgot some of the details or lost my train of thought...

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...

How I Discovered Entrepreneurship and, in turn, Myself

I'm not sure if many of you know this, but I stumbled into entrepreneurship completely by accident. As a young man, I was a few years out of the US Air Force and spent...

Entrepreneurial Advice is Not Always, One-Size-Fits-All

A prime component of being an entrepreneur is sharing your experiences and soliciting advice from those who have been successful.  Which sounds helpful all around...

Dailybreak CEO on Driving Users to Action

Online challenge and engagement marketing website CampusLIVE has come a long way since 2008...

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...

Series on Trust: The VC and His Investors

I’ve been writing a blog series about trust.  I started with a post on how VC is a “trust business” and I highlighted why trust between an entrepreneur and a VC is important...

Using Your Corporate Culture as a Weapon

Take a second and think about your fellow employees—those whom you manage, your peers and even your managers or mentors—do you know what their strengths...

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...

Series on Trust: When Entrepreneurs and VCs Break Up

We met with some of our large investors recently, and one of them mentioned: “VC is a trust business.”  He was saying that he trusted us.  I’ve been thinking...

Care.com’s Sheila Marcelo on Building a Successful Consumer Website

Boston isn’t known for its consumer-facing websites. However, Waltham-based Care.com offers a notable exception. Founded by a team of Upromise executives...

Social and eCommerce

In the wake of the Pinterest round valuing the company at $1.5B from the Japanese ecommerce giant Rakuten, it is hard not to notice that social and ecommerce have...

The Slog Continues…

Last week the National Venture Capital Association (where I am on the Executive Committee) and Thomson Reuters announced the 2Q12 fundraising data for venture firms...

The Rise & Fall of Great Venture Firms [Part 2]

Last week I wrote about some of the common factors that have led great VC firms to stumble or even fade from existence entirely.  I wanted to follow-up with some...