The time I met Jeff Bezos, or why you might want to quit your job and vlog

I’ve told this story a bit, but with Jeff Bezos in the news today, it seems as good a time as any to blog it. Back in 2008, at SXSW, I met Bezos briefly, and got a bit of insight into how he stays open to new ideas and opportunities.

(Jeff Bezos at SXSW, as captured by iJustine

That year, I’d put together a panel called “Quit Your Job and Vlog.” It was a pretty sensational title, considering it had only been a couple years since Jason Kottke had been the first to make the leap to blogging full-time, and no one had heard much yet of videoblogging.

I pulled together four of the most inspiring (and only) people I knew who were making a living creating videos on the Internet. There was Lisa Donovan, better known then as Lisa Nova, one of the first YouTube stars, who’d just come off a season on MADtv; Bre Pettis, who’d quit his job as a schoolteacher and was creating MAKE Magazine’s videoblog; Lindsay Campbell, signed to CBS after hosting and co-writing the early web breakout Wallstrip, which CBS acquired; and Zadi Diaz, creator and host of the seminal Epic Fu, one of Next New Networks’ first hits. Yes, that Lisa Donovan, that Bre Pettis, that Lindsay Campbell, and that Zadi Diaz. I confess that I largely put together the panel to hang out all weekend with four people I really admired, a strategy that’s served me well over the years (see also, “It’s not TV, it’s social TV.”)


(photo by bre)

The title and panelists did the trick, as we found ourselves in one of the larger rooms at the conference, packed front to back with people. The discussion went well, but I was distracted by a familiar-looking man in the front row. He was avidly following along and taking notes, and made eye contact in a way that made me think I must have known him from somewhere – maybe someone I’d worked with from The Washington Post, or Sprint, or any one of a dozen companies. We all found ourselves talking to people for a good twenty minutes or more after it ended, and I noticed after a while that the same man was waiting patiently to introduce himself. His demeanor and dress didn’t scream billionaire genius – if anything, he came across more like Gus Fring (I mean that as a compliment, I love Giancarlo) in El Pollo Loco mode: reserved, composed, and amiable.

Finally he stepped up and put out his hand, and started by saying, “I really enjoyed your panel. It’s been the highlight of my SXSW trip so far.” Flattered, I shook his hand and said, “Wow, thank you very much,” then, as I looked down to his name tag and back up to his face, “…Mr. Bezos.”

For the next several minutes, I stifled my astonishment as he asked a few rounds of questions about distribution for web video content, how people were making money, and what my relatively new company was doing in the space. They were as insightful a set of questions as I’d heard from any investor during our fundraising (and more so than many), as he honed in on the key challenges and opportunities, and drew parallels to Amazon efforts like CreateSpace and S3 (which we used for much of our hosting, on a CMS built by none other than David Karp and Marco Arment) which also were enabling artists and creators to reach audiences directly. He ended the conversation by asking if we were raising money, and if I would send him an email with more details about Next New.

"Of course," I said. “Is your email really…"

He replied with something like, “That’s the one.”

The story doesn’t go much beyond there. I did write him, he did reply, and we did speak with Amazon’s investment group, though we ended up being too far along in our fundraising to be a good fit. First, of course, I let my co-founders and investors know about the meeting, and spent a good part of that night drafting my email to him, trying to figure out the best way to open it so that whoever might screen that address could tell that I really did meet Jeff Bezos at SXSW and he was expecting my email. I still have the exchange – here’s how it opened:


Thanks so much for coming by our “Quit Your Job and Vlog” panel at SXSW yesterday, and for the encouraging words you had to say afterwards about the new online TV space we’re in. I really appreciated your compliments and insight – it meant a lot to us that we could put together a panel that could be as interesting for you as for some of the just-beginning content creators who also spoke to us afterwards.

I included some information about Next New and our current round, and even invited him and his team to the huge Rock Band party we were throwing with Tumblr that night. His reply came almost right away, and made my day:

Tim, thanks for the follow-up — I’ll get you introduced to the team. Thanks for the party invite too. Unfortunately, I have to head home today.

Your panel was the highlight of my visit!

There you go – a perfect gentleman. And a perfect example that, no matter how much you know, there’s always something new to learn, and people to meet that could open up a new perspective. It’s in part why I meet with anyone who wants to, anytime I can, and why I drop into panels on topics I know nothing about and sit up front, and it’s a quality I’ve seen in lots of successful people over the years.

I’ve got a soft spot for The Washington Post – they were one of the first and longest-running clients of my first company, and I wouldn’t have a career without them – and while I have a lot of respect for the Grahams, it’s really intriguing to think of the Post with someone as intellectually curious as Bezos at the helm.

As for my fellow panelists? Quitting their day jobs worked out just fine for all of them, including the founding of two industry-leading companies with the name “Maker” – and of course, many thousands have followed. I still recommend it.

And per Bre’s advice, I’d still recommend taking care of your teeth.