Lessons Learned

Raise More Debt Before You Raise More Venture Capital

Did you have to re-read that headline a few times? I admit, it might seem a bit confusing coming from a venture capitalist.  But here’s the truth: there are plenty of expansion stage...

Raising VC money: how to handle the 1st VC meeting?

This is the third post in a Friday series on “raising VC money”.  For the list of topics we are covering, click here.  In this post, we’ll focus on “how to handle the 1st VC...

Tools to Launch Your Startup on a Shoestring (Part 1)

During a Sunday afternoon last year, I came across an article about how to quickly and cheaply launch a business. I had been wanting to start a side project to get more familiar with...

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...

The 7 Business Slides for Startups

You’re an early stage entrepreneur building a Web-based subscription business. You have your board meeting coming up soon, or you’re sitting down with your close...

Scaling for Growth? How to Hire Superstars

The idea is working… you have great investors, you have hired exceptional people, your core product is built, your customers are happy and they want to know what is coming...

7 Lessons Entrepreneurs Can Learn from Teachers & Students

Teachers and 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...

Tech IPOs Are Back – So Now What?

In the fall of 2010 I laid out reasons why all the tech “bubble” chatter was really more the hallmark of a reasonably sustained boom, and then revisited the topic almost one year ago to the...

Be Quick But Don't Hurry

One of many famous credos of the late, great Coach John Wooden.  Everybody talks about moving at web speed.  As it applies to making decisions about All Things People...

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...

KNOW and BELIEVE Your Elevator Pitch, Don't Just Memorize It

Every entrepreneur has heard of the importance of his/her "elevator pitch"... the succinct description of your business you're supposed to have at the ready when a VC says "so, what's your...

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...

What Happens After The VC Associate Cold Call?

An entrepreneur I really admire asked me for advice on how to handle associate cold calls from VC firms.  I thought the best way to answer that question is to share what happens...

If You Can’t Recruit a Tech Co-Founder, Learn to Market, Not to Code

I’ve noticed a growing amount of advice for business entrepreneurs on how to find a technical co-founder.  The advice seems to be “don’t delay if you can’t find one; learn to code.” It’s really...

Tips on building out your early stage marketing team

I’ve been getting this question often: “What positions do you fill first when building early stage marketing teams?”  Well. Here’s the deal. I’ve been fortunate enough to work at several...

Taking a Leap of Faith...the Enpocket Story

"There are moments in a company's life where you have to jump..." - Mike Baker.  Towards the end of last year, Silicon Valley Bank...

Existence Proof to Scale–From Point to Line to Curve

How do you grow a software business? What does growth look like? This is what growth looks like. It starts slow, almost linear, from zero, and then (we hope) accelerates. The horizontal...

Octane: Boris Revsin - CEO, CampusLIVE

Welcome to the latest installment of Octane!  Today, we are featuring the CEO & Co-Founder of CampusLIVE in Boston... Boris Revsin!!!  CampusLIVE is a high growth startup...

Founder Dialogues VII featuring Russ Wilcox of E Ink

You see the future... you have the technology... however, the market and mass consumer...

The #1 VC in the World: Customers

Need capital to start or build your business?  Ever try to figure out who the best fit VC is for you?  In my view, the absolute best way for you to get the capital to build your business...

Demoing Product

Most product demos are disastrous. I’ve gone through more trainwrecks than I would care to have, and thought I’d share some of my scars and random learnings on the topic...

WANTED: Engineer to Build My Product

As many fellow non-technical folks know, it’s not easy selling an engineer on building a product that’s not their own. To remedy this situation, many people (including myself) have...

How to Get Started on Social Media: Take It One Network at a Time

I recently had coffee with a friend and former colleague whom I met working at Google. We’ll call him Jake. Jake now works in education, at a premier music and arts school outside...

How Smarterer Grew by More Than 1250% in One Week

We’ve been developing Smarterer for the better part of a year now, quietly building a platform that uses crowd-sourced questions to validate peoples’ social and professional skills.  Like many...

Octane: Joe Cronin - President & Founder, Edvisors

Welcome to the latest installment of Octane, our Q&A series with local entrepreneurs.  Today, we have Joe Cronin, the President & Founder...

Thirtysomething Entrepreneurship

As I recently hit the second half of my 30s, I must admit that my views towards entrepreneurship have changed since I launched my first company at 22. Entrepreneurs like myself are...

Five lessons after five years of Punchbowl

Five years ago this week, I was part of a small team (me, Sean, Devin and Gerard) that launched MyPunchbowl.com (now Punchbowl.com). The site...

The Truth About Your Next Hire

Checking references is a normal part of the hiring process.  Although they are meaningful, it is unlikely that a candidate is going to give you a set of references that don’t speak...

Knowing your strengths and weaknesses: actually the most important interview question

One of the most clichéd interview questions is “what are your strengths and weaknesses.”  Most of us have heard it so many times that we’ve prepared for it extensively.  Often we...