Sunday, September 30, 2007

Career Advice for High Achievers

Just before graduating from school with your freshly minted Computer Science degree, you need to find an answer to an intimidating question: What should you do with your life?

Before graduating from grad school, I was thinking about starting a startup with two classmates – but that never materialized. Later, I joined Google, and after half a year, quit, relocated to San Francisco, and joined Xobni.

While I am not the ultimate expert on career advice, I have thought through the options many times. I have flip-flopped on my decisions enough to have achieved wisdom through pain. Here’s what I learned.

As a high achiever, there are four things you might want to optimize for:
  • financial rewards
  • public credit for your achievements
  • work-life balance
  • leaving a lasting positive influence on the world

(If you don’t agree with at least two of these goals, this article is not for you.)

This article tries to answer the question: Should I
  1. join an established company,
  2. start my own company, or
  3. join an existing startup?

I deliberately excluded the option of joining a mediocre large company. At a landlocked company, you’ll learn about upholding the status quo. If you join a company that isn’t number 1 or 2 in its field, and you’re in a junior position, you’ll see mediocrity, not strength. Mediocrity won’t let you to achieve the goals I outlined above.

Let’s go through your options, in the order given above.

1. Joining an Established Company

[+] Getting your resume stamped
[+] Best work-life balance
[+] Higher initial compensation
[-] Harder to get public credit for your achievements
[-] Politics, established organizational structure
[-] Lower long-term financial upside

This is by far the safest choice. Joining BigCo is an society’s template. Your grandma will be proud of you. Your friends will congratulate you when hearing about the job offer. But is it a good deal?

Working for BigCo has great advantages: The company is already set up for success. All the infrastructure is in place. You can start working quickly, training and documentation are available. If you’re working on BigCo’s distributed file system project, you will learn about building distributed file systems (valuable experience), instead of spending time installing Linux on your startup’s server (less valuable experience). If you get in trouble, there will be smart people working there to ask questions. At the startup, you’ll be on your own.

You will have time off, and will enough time and money to burn to go to Barcelona for the weekend. You’ll lead a more balanced life.

But there are downsides to BigCo. While you will receive some equity and bonus in your compensation package, you won’t be rewarded as much for exceptional achievements as if you owned the place yourself. You’ll deal with office politics: People might be incentivized to make themselves bottlenecks, not to help you achieve ambitious goals. The public face of the company will be the founders, the CEO, and exceptional people with good relationships to the PR department, not you.

Here are two tips for people who decide to go this route:

First, make it clear to your manager that you have high goals. Set specific, measurable, ambitious goals. This will drive you to work harder, set you apart from peers, while at the same time allowing for rapid advancement.

More importantly, find a good mentor. Find someone whose incentives are aligned with the company’s, not your manager’s. Don’t choose a fellow engineer who’s just been at the company longer. Find someone several levels up. Higher-ups have a broader view. They’ll be happy to mentor you if you appeal to their sense of ego. Don’t be shy about emailing that Engineering Director.

2. Starting a Startup

[+] Massive financial upside if it goes well
[+] Best if you’re an entrepreneurial type
[+] Best for getting public credit
[+] Best for positive world impact
[-] Hard to find co-founder
[-] Highest risk, potential public failure
[-] Need to build infrastructure that already exists elsewhere
[-] By far the most work

Paul Graham wrote the book on this topic. I’ll just give you my diffs.

If all goes well, starting your own thing will propel you into the stratosphere. You’ll be rich and famous. You might even have changed the world for the better.

There are risks and difficulties: If you fail (and you probably will), you risk public humiliation. This is especially true in European and Asian cultures, where you’ll have a lot of ‘splainin to do.

Out of all the options, this one takes the most work, and will lead to the most grey hair: Founders need to be emotionally stable.

At the onset, finding the right cofounder is success factor number one. You don’t want someone who’s a clone of yourself. If you’re an engineer, get an engineer with business talent. You’ll need technically proficient people, but also the guy who can negotiate good deals with investors and business partners.

Any place likes big companies. But for a high-tech startup, you need to be in a place that is accepting of you. A place where you can surround yourself with people of similar aspirations. Zurich is not that place, and Wichita, Kansas isn’t either. If you’re in Europe, move to London. If you’re in the US, move to the Valley.

3. Joining a Startup

[+] More financial upside than BigCo
[+] Lower financial risk than starting your own company
[+] Stable income, especially when venture backed
[-] Less public credit than if you are a founder
[-] Less financial upside than starting startup

Doing your own startup is the adventuresome path to follow, but there’s a less risky middle way: Joining an existing one.

This is a hybrid model of 1 and 2: If the company does well, money will rain, not pour (early employees receive significant amounts of equity). You’ll have credit for being one of the people who made a future BigCo a success, but the cover of BusinessWeek will show the CEO, not you. If you join after significant funding, you’ll have a stable income to live from.

Before you decide about joining, make sure the startup is set up for success. Meet with the key people, and ask them all the hard questions about what product they will build, how it will make money, what the equity structure is like, who controls the company, what the relationship between the founders is like, and what their plans are if things go awry. Do the due diligence. Join if you’re convinced.

After a startup, you can always go back to BigCo (but with more battlefield experience), or start your own. That’s what makes this option a good launching pad.


Want to backtrack my agonizing about career options? Read these entries:

Update: Another take on this topic, but from a macro perspective: Marc Andreesen’s Pmarca guide to Career Planning.

Saturday, September 22, 2007

Photo Story: The Days Before the Xobni Launch

This post tells the story of the weeks at Xobni before the launch of our first product, Xobni Insight.

Just after we decided we were going to launch at TechCrunch 40, I drove down to Palo Alto to chat with Paul Buchheit and his experience with launching Gmail. One of the most striking things he said was that he didn’t remember much of what happened before April 1, 2004 (Gmail’s launch date), because in retrospect, everything was just a blur. That’s why I decided to snap some pictures and write this post.

The decision to launch did not come easy and we actually flip-flopped on it: We decided to do TechCrunch 40 after deciding against it. There was strong interest from the organizers, and Josh Kopelman, one of our investors, said that it was good to have a deadline. And what a deadline it was! While we didn’t get all our ideas into the product, or refine it to the level of perfection we wanted to achieve, I think we did a great job.

A lot of things had to come together before the launch: Two months ago, our UI looked amateurish, our features were far from complete, and our website was decidedly non-flashy.

Mountains of Work

The engineering team – Greg, Adam, and myself – moved mountains. Greg is in charge of much of the heavy lifting, core code, ranging from NLP, to concurrency, and data flow code; Adam’s specialty is Outlook integration (and he still is the original author of 60-70% of our codebase), and my job is to make our UI fast and delicious. Here are Greg and I joking about some data flow code.

Here’s Adam testing our software on a VM. He’s probably the Windows user with the highest number of concurrently open windows.

Bryan Kennedy, Xobni’s latest addition, revamped our website, and did a lot of our server-side setup. I think it rocks.

Two weeks before launch, we sent the first release candidate into QA (thanks to Jorge and Arlene!). About a week before that, we were working day and night. By that time, my professional pose at work had started degrading.

At some point, Adam and I had a fist fight one night to decrease stress. I wish I had photos. Obviously, I won.

On Short Notice

We already had contracted out some UI refresher work (thanks to Dave and Jeff from Vestal!) when we realized that we wouldn’t have the capacity to get everything quite done. For example, we didn’t have a “Learn More” video until really late. When we decided we needed one, we asked around for someone who could produce broadcast-quality video on a short notice.

Timo Hetzel to the rescue! Timo is a friend of mine from Munich, Germany. He agreed to board a plane to SFO within 72h of my initial email. We even bought some Macs so he could do all the editing work we needed (Timo is also the biggest Mac fanboy on the planet). It’s safe to say that everyone loved the videos.

Another short-term arrival was Jey Kottalam, who whipped our web servers into shape after flying in from San Diego on a 4-hour notice. (Thanks, Jey, for your hard work!)

Tim came in on short notice to handle support requests and did a great job handling the stream of incoming messages and bug reports. Here are Jey and Tim munching on some Pizza Hut in our swanky conference room:

Shipping the First Beta

Eventually, the time arrived to send our beta to people who had signed up for the beta on our website. This was pretty much the first time our software was shipped to users we didn’t know. It’s safe to say that I was excited and afraid of this development.

Greg, on the other hand, stayed pretty calm.

The Final Countdown

On Sunday night before conference started, the entire team retreated to Mel’s. Mel’s, for those of who don’t know it, is an American diner best known for staying open late (and not for good food). We were working late and after 9 pm, it’s the only place left open close to our offices. But even dinner time wasn’t downtime. Matt had brought his laptop and was editing our press release after ordering his burger.

All this effort really paid off: A great product, a great presentation, good press, and happy users. Here’s Matt on stage at the conference.

But, as always, there’s plenty of work left to do.

Wednesday, September 19, 2007

More Xobni Coverage

Om Malik: Is Email The Ultimate Social Environment?
A $350 million buyout of Zimbra by Yahoo (YHOO), Thunderbird being spun out as an independent entity by Mozilla, and the impressive launch of San Francisco-based Xobni: Email, the most socialist of all web apps, is back on the front burner.

Fred Wilson on Xobni:
"It's safe to say that we're blown away ... for those of us stuck in email hell in Outlook, Xobni is showing a way out.

Ed Kohler:
"TechCrunch had tons of impressive companies present, but the one that really jumped off the page for me was Xobni. They have created a new email platform that creates significant value without asking anything more from users. That's a killer combination.

Tuesday, September 18, 2007

Xobni Launch Pics on Flickr

Here are my pictures from today's TechCrunch 40 launch.

Xobni Launch: Initial Press Coverage

Some initial press coverage on our launch:

VentureBeat: "Email company Xobni launches, may steal Techcrunch prize":

"It’s extremely useful and we’ll make a bet now it will win the show here, after the two-day competition between 40 companies finishes (we’ve yet to see half the companies, but it blows away the competition so far). We’ve downloaded it, and are playing with it, and find it truly impressive."

ZDNet: Xobni and Orgoo - Weird Names, Useful Applications (Dan Farber)
"It makes you wonder what Microsoft has been doing with billions in R&D."

Brian Alvey: TechCrunch 40 at Xobni

"The first presenter this morning was probably better than any of yesterday's. It's called Xobni, which is inbox spelled backwards. It extracts some great contact and relationship information from your email stream."

Valleywag: I'm too sexy for my install script.

Drwn News: Xobni, Wow
"I just tried the beta release of Xobni on my machine and it is so great. It actually makes me regret switching away from Outlook for 60% of my mail (Thunderbird is my main business app). MSFT should buy these guys immediately and release the damn thing as an Outlook patch, like they did with Lookoutsoft's search."

TechCrunch 40 Panel: Esther Dyson on Xobni

Our session has just ended. Loved the Mint presentation, I'll probably be using that. Orgoo also seems very useful. On to the panel:

Some funny quotes from the panel:

  • Esther Dyson: "My favorite company from the session? I'd pick Xobni. These are exactly the problems I have."

  • Guy Kawasaki: "If you spent 25k on that name, and I were an investor, I would shoot you."
    Adam: "But - it's inbox backwards! At least you'll never forget the name."

TechCrunch 40 Presentation

We just arrived at TechCrunch 40.

As I'm writing this, Matt (Xobni's Steve Jobs) is on the stage delivering the presentation.

Going really well so far! The audience is a bit sleepy.

Monday, September 17, 2007

Xobni Launching at TechCrunch40

It's my pleasure to announce that Xobni will be launching its first product at TechCrunch 2000 40 tomorrow, Tuesday Sept 18th. This is a huge step for us.

We'll be launching in the session starting 9 am Pacific time. I fully expect y'all to be at home F5-ing your browsers.

Sunday, September 16, 2007

Wash and Fold

The last weeks have been extremely busy here at Xobni. A casual observer could easily reach the conclusion that we have gone insane.

My total of 7 hours of non-sleep free time in the last weeks have been spent on going to a girlie band concert (I had my reasons), and the gym. Being this crunched for time, I decided to do the make the deal: I went to the wash and fold.

Now I looove doing laundry. Not so much the washing, or the drying, but the fresh smell and the great feeling of being organized at the end. Turns out you get both at the wash and fold.

I love a solid service economy in which you can trade money for time. Big thanks to the guys at the Doo Wash! Those were $20 well spent.

Friday, September 07, 2007

More Press = Good Press

Our mystery investors revealed: Venture Beat Article.

"Xobni, the secretive email company, reveals big-name backers."

Also, read these comments on news.yc - good thoughts.