What I'm doing as an Entrepreneur-in-Residence

I promised a few weeks ago in my post about leaving AOL that I'd have another one up soon detailing my new role at betaworks. I'm not sure where the past few weeks have gone, but jumping into a new job at the same time as moving from New York to San Francisco pretty much destroyed all of my free time and so I'm only getting to this now.

"Entrepreneur-in-residence" can be sort of a murky job title; it certainly has come to mean different things for different people at different places. (Side note: does anyone know the first time it was used?) For me being an EIR means working with betaworks' investing team to find early stage startups to invest in, as well as advising and supporting portfolio companies based here in the Bay Area. I knew I wanted to move into investing after I left AOL and this was the perfect way to learn the ropes from some amazing people while figuring out what comes next.

The funny thing is that I even though began my career in technology as a journalist writing about venture capital and startups for Red Herring, it never occurred to me at the time that I would  become an investor myself. I was never much interested in finance and it really wasn't until I started my own company and went through the fundraising process that it began to see early stage investing as something that I might want to do. 

What I found is that early stage investing is  different from other kinds of investing. It's more subjective, for starters. Products and companies are so young that you rarely have much hard data upon which to base a decision, and because of that the process is driven more by intuition and relationships than financial models and analytics. You're essentially making a guess about the quality of a company's product (and its potential to grow), the future size of the market it's going after, and the drive and capabilities of its founders. It's about looking out over the horizon and making a bet on how technology is going to change the world.

In one way or another, pretty much my entire career has been focused on finding that next exciting thing in tech. Editing Gizmodo and Engadget was exhausting -- and something I never want to do again -- but it was exhausting because I was fixated on chronicling every single exciting new product or development in the world of personal technology. I don't blog much anymore, but I still love playing with new gadgets and apps and I'm just as obsessed as ever with trying to figure out what the next wave of innovation is going to be. If you're passionate about new technology and love being around the people working on it there are probably few jobs as well-suited to fueling that passion as being an early stage investor, which is why it seemed like a natural next step for me after being an entrepreneur.

I know that I have a lot of work to do if I want to be any good at this. One of the biggest challenges is going to be finding new opportunities early, so if you are working on something I might be interested in checking out or even just want feedback on what you're building, please get in touch. I'm especially interested in chatting with anyone who has had a hard time getting in front of investors because they don't have the right connections. I know how difficult it can be to get investors' attention, so I highly recommend taking advantage of the fact that I'm new to this! 

Leaving AOL (again)

Yesterday was my last day at AOL. Today I'm joining betaworks as an entrepreneur-in-residence, focusing on seed stage investing, as well as working with portfolio companies here in SF and just generally serving as their ambassador to the West Coast. It's a big change for me and I'll write more about it in a later post.

The last time I left AOL I never made an announcement or posted anything to my blog. I've always felt uncomfortable saying goodbye -- I have a bad habit of trying to sneak out of parties -- but looking back I really regret disappearing like I did. I was already working on a couple of new projects (RCRD LBL which went nowhere, and gdgt, which brought me back to AOL in 2013) and at the time I only wanted to focus on what was ahead of me, not behind me. Of course, I realize now that I left without thanking a lot of people at AOL or acknowledging the hard work of the team that I was leaving and I won't make that mistake this time.

First, I have to say thank you to my team at AOL Alpha, who are without a doubt the most talented and capable people at the entire company and who I've been very lucky to have had the opportunity to work with. They've all done amazing work and I look forward to seeing what comes next out of Alpha. I especially want to thank Evan Fribourg, Michael Cosentino, and Drew Lesicko, who ran Alpha alongside Ryan and me. Their dedication to Alpha has been inspiring and I am going to miss working closely with each of them.

I owe a debt of gratitude Jay Kirsch, who helped spearhead gdgt's acquisition by AOL. Anyone who has ever sold their startup knows that you need someone who believes in you championing your deal internally if you're ever going to get something done and we were lucky to have Jay be that person for us (plus he was awesome to work for after the deal closed).

I also want to thank Susan Lyne, who made me her VP of Strategy after she took over the Brand Group a couple of years ago. I learned a tremendous amount from her, and I suspect that everyone who has ever had the chance to work for Susan feels as I fortunate as I do to have had someone as thoughtful and considerate as their boss.

During my first few months back at AOL I pestered Susan (and anyone else who'd listen to me) about the need to shake up the way the company did product development. It was Luke Beatty who actually stuck his neck out to make this happen. He worked to bring Alpha, our experimental product group, to life, and then gave us the organizational cover to do our thing with a minimal amount of corporate interference. Luke is the real deal and I appreciate everything he's done both me for me and for Alpha. 

Leaving AOL also means that for the first time in many years I won't be working alongside Ryan Block, my long-time collaborator, gdgt co-founder, and Alpha co-director. Ryan was instrumental in Engadget's success, and helping to build first that site, and then later gdgt, was a real privilege. I'm honored to call him my best friend and I'm going to miss building new things with him. The good news is that we are going to continue doing MVP, our podcast, so we will be able to continue our collaboration in one small way. And now that I'm in San Francisco we'll be able to record that in person. 

AOL has been good to me. There were a lot of insanely frustrating moments, I'm not going to lie, but it says a lot that they actually gave Ryan and me the resources to go build stuff and then pretty much left us alone. I met a ton of great people over these past few years and I'll say that the AOL I rejoined in 2013 felt like a completely different -- and better -- place than the AOL I left in 2008. Altogether I've spent a good chunk of my career here and it's hard to be anything but grateful.