Seven

Anniversaries and birthdays are nothing more than a chance to reflect and collect one’s thoughts. This past week the little experiment called GigaOm turned seven years old. It has been seven years of lessons learned, embracing failure and challenging preconceived notions. The past seven years have allowed me to figure out that in life if we are … Continue reading Seven

The Cycle of Second Guessing 

It was a lovely spring day in San Francisco, which is why it made sense for me to meet up with Dennis Crowley, co-founder of Foursquare to catch up on some sun and talk about the 6.0 version of his software. We sat in an atrium, watched the world go by and talked about the new release.

Crowley, who like all founders is running a million miles a minute, took a moment to bask in the glow of positive reviews for the new version of the software. Obviously, not everyone likes it, but as a long-time member of Foursquare, I like the simpler interface that marries discovery, search and check-ins for a glance-able and quick interaction.

There are doubters — actually, there are many who are convinced about the inevitable failure of Foursquare. I am not one of them. I actually like using the service. I am a believer, and I’m not afraid to say it. Because it is indeed the way of the future. Sure, Dennis gets spanked publicly for not doing a good job, but that doesn’t mean he is wrong about the marriage of digital and physical.

While some people may have been surprised by this new Foursquare, Crowley and his cohorts have been fairly consistent about their vision of the world and what Foursquare has to do. He and I talked about this three years ago, and it has taken them a long time to get there. There is a ways to go before Dennis can get to his “Harry Potter’s Map” dream.

The positive reviews and the buzz of the new release are going to last a few days, and then it will be back to the grind for him. The grind that consumes all founders completely. The grind that means managing a big company. The grind that means parting ways with your co-founder. The grind that means dealing with constant naysaying, haters and giants who exist to copy your ideas, poach your people and generally make you miserable.

Those of you who have started a company know what I am talking about — the constant, daily upheaval of emotions. There are days when you don’t want to get out of bed, when you whimper without tears and then shake it all off because deep down you know you would rather be doing this than something else. Founders live to capture lightning in the bottle: sometimes it works, sometimes it doesn’t, but we still keep trying. And that is the part the non-builders don’t get.

Building things that are different, inventing the future and creating a real business is a long and often very lonely slog. But you don’t hear about that. Instead what you get is a lot of babble about startups from so-called mentors, advisors and startup gurus. Peel away their sharkskin and you find they have never started a company, and they continue to live in the reflective glory of the company that once employed them. Others are the creation of social media, having struck a pose. And some are born consultants. They find willing listeners among a growing army of entrepreneurs who like enterprenuership as a lifestyle. Sorry guys, entrepreneurship isn’t a lifestyle, it is life.

This spectacle of technology has attracted fake messiahs, and every day I see this mockery of entreprenuership. I overhear it in coffee shops. I am forced to confront it on social media. And I have to remind myself of Pandora founder Tim Westergren, who sacrificed it all to see his bet finally pay off after more than a decade of struggle. I like to think of Aaron Levie, who returns my email at 3:52 a.m. — a minute after I’ve pinged him. And I think of my friend Paul Evans, who has gambled it all on his company, Shareband.

Ask Dennis what it is all about, and he will tell you: seeing someone check into a location, finding a tip and then acting on it.

That moment is what gets you ready for tomorrow — when all hell breaks loose and the second guessing starts all over again.

Who says startups are easy

A blog post by Fred Wilson, undoubtedly the king of early stage consumer web investing (Twitter, Tumblr, Etsy, Foursqaure, Zynga and Kickstarter), has many folks wringing their hands about consumer Internet investments and extolling the virtues of enterprise or more business focused companies. (It is only a matter of time, before it becomes a fad too, but let’s leave it for another day.)

I am just a little surprised that it has taken people this long to realize that doing a startup in this day and age is a massive problem. It is not just about the money — it is the increased attention diffusion which is a problem. I have been talking about this for a long time. Last year, I wrote about the lack of second chances on the modern, post-mobile Internet. Continue reading “Who says startups are easy”

Founders & importance of friends

Yesterday, True Ventures (a firm that has backed my company and where I spend time as a venture partner) hosted its fourth annual founder’s camp. It was a gathering of those who can simply be described as “the crazy ones.” There were over 125 founders in attendance – talking to each other, teaching each other, and learning from each other.

For a fraction of a second I was a little jealous – there was no such support group when I set out on my entrepreneurial journey. There were so few of us that you could count us on one hand, and still have a finger left to pick your nose with. The first year of being a founder was like climbing a glass wall with nothing but nails for hands.

Continue reading “Founders & importance of friends”