If I had to pinpoint when content curation came on my radar, it was when Matt Drudge broke the Lewinsky story and I, like everyone, discovered The Drudge Report. A few years later I built my first company around curated content for specialized industries. At the time, I liked to think that I was channeling the spirit of Henry Luce, who started Newsweek and Life Magazine with curated content in the 1920’s and 30s.

By content curation, I mean the process of collecting, organizing and displaying information relevant to a particular topic or audience. Today, content curation is everywhere, even in places people don’t think of as “media.” And it’s accepted. It’s fun to see new approaches emerge and add value to people. Hacker News, anyone?

Like many media and startup folks, I’m convinced there are still tremendous opportunities involving content curation, but it’s tricky to...

You’ve raised seed funding, built a team, and launched your product. Maybe some revenue is trickling in.

From the TechCrunch view of the world, everything is rosy. But in your gut, you have a sinking feeling. Why? Because with $X in the bank, you only have Y months to raise a Series A round. And you’re way off track. Your DAUs, MRR, and other acronyms simply aren’t growing fast enough.

Some days you have the zeal of a missionary. Other days you feel like you’re running against the wind. Like hurricane winds. Tension is beginning to surface between you and your co-workers. You’re not sleeping your best. You put on a good face, but deep down you’re wondering, Are we going to be among the majority of startups that fail? In dark moments, this evolves to Am I a failure?

Welcome to the Crunch. Your money is running out, and you’re on a foggy island between success and failure. What do...

Among b2b media and marketing executives, LinkedIn is discussed today the same way Google was ten years ago — in hushed, ominous tones. It’s the new elephant in the room.

The question on everyone’s mind is: To what extent is LinkedIn a threat to my business?

In the course of providing guidance on this, I haven’t been able to find a map of all of LinkedIn’s product offerings. So, I took a shot at producing one:

As you can see, LinkedIn’s product offerings are oriented around its three main lines of revenue — Talent Solutions, Marketing Solutions, and Premium Subscriptions — and an emerging set of media features.

The two areas causing consternation among media and marketing execs are, obviously, Marketing Solutions and Media. Here’s what I tell these folks:

The Big Threat

The big threat posed by LinkedIn is its growing share of eyeballs and marketing dollars that historically have...

I recently completed the first leg of executive-coach training. I’m surprised by how much I liked it!

I signed up on a whim, literally the day before the course started. I booked a last-minute flight to Chicago, and then spent the next two and a half days immersed in a la-la-land of coaching at a hotel downtown. My friend and former coach Jeff Ward had recommended the training company, CTI. I took their Fundamentals Course, which is the first of a series of five to get certified.

Why on Earth would I do coach training, you might be wondering? Having sold my latest business in August, I’ve decided to spend a few months “sharpening my saw” before diving into the next venture. Coaching is something I’ve always wanted to explore. Having benefited from coaching as an entrepreneur, I recognize the value of it (though admittedly, it was a long time before I took it seriously). I’m also at...

I recently completed the first leg of executive-coach training, as reviewed in my last post. My aim was to develop new leadership skills before diving into my next business venture. As it turns out, the skill I needed to improve the most was empathy — or more precisely, my attitude towards empathy.

Here’s what happened: The instructors, sniffing out a weak spot, told me to practice being extra “warm & gooey” for the entire second day of the course. I winced at first. Then I stepped up my level of warmth and empathy as genuinely and as earnestly as I could. It was hard. By the end of the day, a funny thing had happened: My coaching sessions improved. My clients got better results. I bonded more with my classmates. I felt more connected.

The experience reminded me of the importance of empathy as a personal and professional skill. I mean, I’ve always understood this intellectually, but...

a sheep with a unique scarf

Today I watched a TED talk on the value of authenticity. It was delivered by a woman in her early 20s. She gave it barefoot wearing a 19th century-looking blouse. It was a moving speech, but I couldn’t help but ask myself: Does she realize how much of a product of the Internet era she is? Seriously, a speech on authenticity and “finding your voice” at a TEDx event?

I don’t mean to make fun of this young lady. I admire her courage and speaking ability. I do, however, want to point out a central irony of social media:

Social media is an incredible outlet for individualism, but it also ties us to powerful social forces that control us more than we realize.

The image of social media, as a cultural phenomenon, is one of radical individualism. We’re into personal branding. We design our own careers. We’re truth-seeking and networked, letting our unique voices...

One thing I love about B2B is the opportunity for idea arbitrage: See what’s working in consumer tech, and then implement it in the business world before everyone else does.

Right now, I see this kind of opportunity with Convenience Tech. By this, I mean the rise of on-demand services in the model of Uber.

Go to a website or app, and in minutes you can:

• Hitch a ride via Sidecar
• Line up a landscaper via Zaarly
• Schedule a house cleaning via Exec
• Order dinner via DoorDash
• Get your laundry and dry cleaning done via Washio done, or
• arrange someone to watch your dog while you’re away via DogVacay

There are dozens, maybe hundreds, of Convenience Tech startups emerging in this vein.

Where’s the B2B equivalent? I mean, have you tried finding a lawyer or accountant or bookkeeper lately? It’s true that TaskRabbit is beginning to target SMBs. If you look hard enough, there are a few...

This is a run-down of my advice to entrepreneurs on selling and exiting their businesses. No one talks about the personal dimension, so I try to cover both business and personal issues. The format is inspired by James Altucher’s recent TechCrunch FAQ sheet on starting a business. Feel free to disagree or add to this, and I can go deeper on specific topics in future posts. Here goes:

Wait… who are you to give advice, Jeff?

I’ve built & sold two businesses — one successfully, the other less so. I’ve helped friends sell their businesses and have participated in “forums” of recently exited entrepreneurs, both the sappy, what-to-do-now kind and the practical, how-do-I-manage-my-money-as-a-rich-guy kind.

I’m not an expert, just a guy who’s learned the hard way on a few of these items and did well on most others. Can we get on with this now?

Yes. Should I hire an investment bank to manage...

I did a negotiation simulation in college and came in last place. We’d paired off to negotiate a transaction involving an imaginary bean company. I sat across from my negotiation partner and thought about the ass-kicking I was about to do. I did terribly.

The people who did well, it turns out, approached the simulation as a problem-solving exercise rather than a competition. They started by understanding their partner’s needs and priorities vis a vis their own. Then they made trades that were mutually beneficial. Among those who did well, their “opponents” did well too. High scorers skewed female.

My shellacking was one of those forehead-slap learning moments you never forget. Today people view negotiation as one of my strengths, but I don’t really believe in “negotiating”. I believe in solving problems. I like sitting on the same side of the table. If we can’t find a solution that...