Should a Startup Have a COO?
It’s rare I can dust off a 6-year old article, find it still relevant and repost it without any changes. But that’s what happened this morning, I felt provoked by this VentureBeat title: Even start-ups need a COO – wanted to respond, than I had that “I’ve already said this” feeling and realized I would [...]
The Art of Riding the Bubble
People are increasingly asking whether there is a Bubble underway in the tech business. The answer is that by the time you know there is a Bubble it’s probably too late to do anything about it. But if all you’re doing is asking whether there is a Bubble, the Bubble is probably not here, yet. [...]
Silicon Valley > Boston (The Data)
I love Boston. I lived there for five of the best years of my life, when I was working at D. E. Shaw & Co., and then when I attended Harvard Business School. If anyone asks, I always tell them, “if Boston had the same weather and career opportunities for me as Silicon Valley, I’d [...]
8 Questions to Help Decide if You Should be Raising Money Now
A year ago I blogged about one of my most common mantras that applies to sales, biz dev & fund raising alike: “Time is the Enemy of all Deals.” When times are really good for fund raising many teams delay to maximize their valuation. Sometimes this pays off, other times it doesn’t. So how should [...]
The Top 30 Most Respected Venture Capitalists (infographic)
A guide for Entrepreneurs There is a lot of content created by the Venture Capital community that has helped countless entrepreneurs. In fact, one of my favorites is How Andreessen Horowitz Evaluates CEOs. I recently stumbled upon the article again and it reminded me of an article I’ve been meaning to write for my entrepreneurial [...]
Why Did I Invest in Pose?
What a sweet feeling it was last week to see the launch of the photo sharing site Pose, whose application targets shoppers of apparel. If you don’t know it and own an iPhone (soon Android) please check it out. What I’d like to do is tell you the story of how the investment came to [...]
Going to Raise VC? Here’s a Primer on Process, People, Deck
If you want a very quick primer on all the stuff nobody ever tells you about raising venture capital check out this video where Mark Jeffrey & I break it down on This Week in VC. A summary of what we discussed is below: Not 100% in order of the video, but close. All of [...]
Why it’s Critical That you Reference Check Your VC
I was recently speaking with some founders about their fund raising process. They had received a term sheet from a VC and were wondering whether to work with this firm. I personally had three separate data points from entrepreneurs who took money from the firm that said “never again.” I really try to stay out [...]
Invest in Lines, not Dots
Everyone seems to be in such a rush to get shacked up these days. In normal times investors will look for “traction” before investing. We want to make sure we’re in love. This sometimes frustrates entrepreneurs who just want to “get back to running the business.” But if you understand it you’ll see that it [...]
An Entrepreneur’s Growth Equity Conundrum: Should I sell stock or sell growth?
Two times in the past year, I’ve been close to making an investment in two separate micro-cap growth equity opportunities only to have the opportunity go sideways deep into the process. The two businesses share a lot in common; they are similar in size, profitability, and growth prospects. Both are capital-intensive; the first being asset [...]
The Four Main Things that Investors Look for in a Startup
I obviously don’t speak for all investors. But in my experience as an entrepreneur and now spending my time amongst investors I can generalize that almost all VC investments in early stage technology & Internet investments come down to just four key factors. And they’re easy to remember because they all begin with an M: [...]
Outbound VC Dialing Programs – Total Disrespect for Entrepreneurs
I recently got an email from a friend who had been approached by a well known VC. He sent me an email asking whether the approach was real and whether he should take it seriously. Here is the email he received (reprinted without names with his permission). “Hi [entrepreneur], I hope all is well. I’m an [...]
Is Convertible Debt Preferable to Equity?
Seth Levine of Foundry Group addresses this important topic this morning on his blog with a post, “Has Convertible Debt Won?”Seth was basing this on a Tweet by Paul Graham that said” “Convertible notes have won. Every investment so far in this YC batch (and there have been a lot) has been done on a [...]
Slide's Slide Down to Google
Not much to add. It’s all in the pic. Well, perhaps this quote from Will Price, a smart VC-turned Startup CEO: It may well be that Slide raising $55m from mutual fund companies at $500m+ pre-money will be the “what were we thinking” moment of the current cycle. Slide is believed to have raised $78M in [...]
Atlassian: Fully Funded. By Customer Revenue. Oh, and the $60M T-shirt
It was 2006, the first Office 2.0 Conference in San Francisco and I just met Jeffrey Walker, President of Atlassian. I had followed the company for a while (OK, I admit, had been a fan), met Mike, but this was the first time with Jeffrey, so we took our box lunch to a cozy little [...]
