the cornice

It’s easy to adapt to challenges you face many times. It’s difficult to be good at the things you rarely confront. Knowing how to adapt to seldom seen circumstances is the key to driving a start-up forward.

This past January, we held our annual First Round Capital CEO Summit to bring together our portfolio company CEOs and founders for a day. Our goal is to keep the day focused on topics that the CEOs can use in the daily operations of their businesses. We’ve been luck enough to have some great speakers join us, but the meat of the day is in the breakout discussions. This year, I facilitated a discussion on “Knowing When to Pivot.” Pivoting is one of the most critical challenges a business can face. It’s also one of the most rare – not many folks have a great deal of practice in this arena – so I wanted to share some of the key takeaways from the discussion here.

So what is a pivot? It’s what you do when you’ve built everything according to plan and yet, the business and users aren’t materializing according to plan. For the record, I’m a huge believer in all aspects (engineering, customer & business) of agile development. No need to debate that here. Sometimes, however, it takes awhile to see that it just ain’t gonna work out. PayPal as we know it was built after a legendary pivot. And in our own portfolio, Like.com, took shape after originating as a very different business. Here’s what you need to know about pivots and why you shouldn’t be afraid of making them: Read the rest of this entry »

It’s always surprising when you see the lessons of the tech start-up world reveal themselves in unexpected places. This past weekend my I saw the movie, “The September Issue.” It is a documentary on the production of a single issue of the women’s fashion magazine Vogue and its editor Anna Wintour. The movie is true story behind “The Devil Wears Prada” and Ms. Wintour is said Devil. For any entrepreneur, it is “much watch” material.

Some background on the story. The September issue of any fashion magazine is the most critical issue of the year. It is the issue that sets off the fall and holiday buying season. September is to the fashion publishers what December is to retailers. Of course, in the world of fashion magazines there is no publication more important than Vogue and no person more important than the iconic Wintour. Wintour is known for scaring and scarring both designers and her team alike. In this regard, she does not disappoint. But “The September Issue” is also an opportunity to witness the best in their field prepare for their biggest moment.

Some of the start-up related lessons from witnessing the Devil herself:

• Delusion is Good. There is a revealing scene in which Anna Wintour discusses her siblings and what they do for a living. One is involved in non-profit work, another is an Editor for the UK’s Guardian newspaper. She then says, “I think my family is amused by what I do.” But she is not. The world of couture is not frivolous to her. Vogue is important to the world. It is easy to laugh at this notion, but for those outside the tech world  it’s also easy to laugh at the notion that creating better online ad platforms, communication systems, shopping experiences is important. If you are going to start a company, start by believing that what you are setting out to do is important.
• Love what you do. If you succeed in convincing yourself that your idea is important, chances are you will love creating it. There is a scene in “The September Issue” in which Grace Coddington, the Creative Director of Vogue, just having been dressed down by Wintour muses “Well, of course, I want the issue to be a success. My job depends on it.” Coddington will never have difficulty finding employment. She isn’t speaking about employment. She has long and storied career in the fashion industry and many would fight to hire her today. Vogue clearly is not a “job” to her. You can see the way in which she revels in her work (its struggles) and colleagues she is passionate about Vogue. It is her life.
• Refine, Release, Repeat. Here’s the plot of the film. They set out to produce an issue of magazine. They struggle with production. They fight. They refine what they want the issue to be. They reshoot. They find new inspiration at the latest possible date. And then they release their creation to the world… And then, just before the credits role work begins on the October issue. Sound familiar?

This post is a bit of a commercial and I have no intention of apologizing for it. In fact, I’m incredibly proud of it.

Many venture capital funds will tell prospective entrepreneurs, “If you take funding from us, you won’t just have one person working on your behalf, you’ll have our entire team pushing for you and opening doors for you every day.” As you might expect some firms are truer to this mantra than others. For founders choosing their funding partners, this is one of the most important areas on which to perform diligence. Ask other companies in a VC’s portfolio how often they interact with multiple members of a VC firm. The answer will reveal an enormous amount about the health and culture of the partnership. As a founder, you want a VC that acts as one team of many people, not many people acting as many individual teams.

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