Arranged marriages in the startup world

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

My wife and I have picked out the perfect spouse for my son.  They have developed a wonderful relationship together over the years, with great chemistry and warmth.  She comes from a family that has identical values and priorities to ours and would make wonderful in-laws.

They are both 9 years old.

This … Continue Reading

Launching a start-up? Do it without titles.

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

There has been a recent dialog around a theme I’ll call “hacking the corporation” – creating novel approaches to building young companies, particularly when they are in their formative start-up stage and pre-product market fit.  One of them, reinventing board meetings (or, “Why Board Meetings Suck”), has gotten some attention from leading thinkers … Continue Reading

5 lessons entrepreneurs can learn from the Navy SEALs

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

There has been a surge in interest with the world of the Navy SEALs since the Osama bin Laden action (this piece in the WSJ was a particularly good profile) and I confess to being caught up in it myself.  One of my portfolio company CEOs, Will Tumulty of Ready Financial, is a … Continue Reading

Hire a recruiter. Now.

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

The unemployment rate in America is hovering around 9 percent. But if you are a competent engineer, sales executive, online marketer or general manager in Silicon Valley, NYC, Boston or other start-up hotspots, the unemployment rate is 0 percent.

The talent market has gotten as competitive and aggressive as I have ever seen … Continue Reading

What if it’s 1996, not 1999?

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

In May 1996, Open Market completed a successful IPO and more than doubled on the first day of trading, ending with a $1.2 billion market capitalization.  We had recorded $1.8 million in revenue the year before.

If investors observing this extraordinary phenomenon in 1996 were to have concluded that the technology market was … Continue Reading

Depressing thoughts on Groupon’s model

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

You probably read a lot last year about Groupon’s rejection of a supposed $6 billion offer from Google.  Most of the reports breathlessly described the explosive revenue and customer growth the company has achieved in two short years and what a breakthrough the model.

With over 40 million email subscribers, Groupon’s success is … Continue Reading

My, what a big balance sheet you have!

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

In undiluted tellings of the tale, the Big Bad Wolf devours Little Red Riding Hood before running off into the woods. That’s something worth remembering when considering the prospects for a wave of technology M&A that’s about to materialize.

Over the last few months, investment bankers have been eagerly reaching out to corporate … Continue Reading

The ABCs of pitching investors– Always Be Credible

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

In his best-selling book “Blink,” Malcolm Gladwell made famous the natural human reaction of quickly judging other people.  This behavior is especially true of VCs and angel investors. The first few minutes of an interaction are crucial.

The way an entrepreneur starts an investor pitch meeting can actually determine their success in that … Continue Reading

Why entrepreneurs seem to be growing fangs

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

One of my favorite business school professors, Andre Perold, used to like to say that in every transaction in the financial markets, there are only two types of actors:  wolves and sheep.  As you might expect, the wolves have the edge in the encounter, due to superior market information or negotiating position.  If … Continue Reading

Sometimes, conflict between VCs and entrepreneurs is a good thing

Sometimes, conflict between VCs and entrepreneurs is a good thing

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

You hear the word ‘alignment’ thrown out a lot in business conversations.  And while it’s a wonderful thing to aspire to, it’s hard to achieve – particularly in entrepreneurial settings between the venture capitalist and the entrepreneur. It’s there, after all, that the … Continue Reading

Is the sky falling or are we entering a golden age?

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

The news headlines are grim.  Oil spills, sovereign defaults, choppy stock markets, tepid employment.  It’s no wonder that the global capital markets seem spooked.

Yet, here’s the strange thing, many of us in the technology sector of the venture capital world have never been more bullish about what lies ahead.

It’s like a … Continue Reading

Stock vesting: Why is four the magic number?

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

There’s a historical anomaly in start-up compensation that I’m struggling with.  Although I know this risks being an unpopular post with entrepreneurs, I confess that I no longer get why we have four year vesting schedules for stock option grants at start-ups.

Let me explain.

Vesting is known as the time period during … Continue Reading

Sometimes, mother-in-laws top hard statistics

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

I’ll never forget my first marketing class at business school.  Our professor peered at us with an intense glare as he pushed back on our standard, “chip shot” comments.  At one point in the class he asked the guy next to me to opine on the case we were discussing, which involved launching … Continue Reading

The lost generation of entrepreneurs

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

I’ve been worrying lately that we are suffering from a lost generation of entrepreneurs.

That was my first reaction when I read what Sequoia’s Doug Leone said a few weeks ago about innovation and age at a recent talk with MIT Sloan students visiting Silicon Valley. In a nutshell, Leone claimed that only … Continue Reading

Why do VCs blog (and Tweet)?

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

For decades, the venture capital industry was like a Yale Secret Society – very clubby, discrete and opaque.  VCs had all the power in the VC-entrepreneur equation – and entrepreneurs had to work hard to decode the mysterious VC process to obtain funding.

My, how the world has changed in a few short … Continue Reading

Three ways to prevent executive fraud

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

A lot has been written in the last few weeks about the scandal at Canopy Financial, a venture-backed, high-flying start-up that attracted over $100 million in capital at increasingly higher prices from top-tier firms, only to come crashing down in a dust of rubble and fraud.  The VC community suffered a very similar … Continue Reading

What rehab taught me about making bad investments

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

For as long as I can remember, I have been an enthusiastic participant in sports.  To be clear, I’m not a great athlete (in fact, I’m the only one of the five Flybridge General Partners that wasn’t a varsity athlete in college). I’m just good enough to participate passionately and aggressively like the … Continue Reading

The VC gender gap – Are VCs sexist?

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

I find the preponderance of males in VC an annoying and stubborn phenomenon.  When I first entered the start-up game as an entrepreneur in the mid 1990s, I didn’t think much of the “VC gender gap” as there were plenty of women executives around.  In fact, between one-third and one-half of … Continue Reading

Negotiating VC funding? Look beyond ‘the pre’

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

VCs have an unfair advantage when it comes to financings.  They simply have more experience doing deals.

A typical start-up company will do 2-4 venture capital financings before a successful exit (or, conversely, an ignominious ending).  A typical serial entrepreneur may lead 2-3 companies in their career before calling it quits (or checking … Continue Reading

The idea's great, but the leadership team stinks…

(Editor’s note: Jeff Bussgang is a General Partner at Flybridge Capital Partners. This column originally appeared on his blog Seeing Both Sides.)

One of the things I continue to struggle with as a VC is the unfortunate fact that I am in the business of saying “no” all the time.

Saying “no” in the context of how you invest your time is one thing – fellow VC blogger Brad Feld did a good … Continue Reading