Niche Passion: How to Find Work You Love

October 25, 2010

My weekly post on Seattle 2.0.

Most of us are not lucky enough to know what we want to do with our lives.  Everyone knows someone fortunate enough to have discovered work they enjoy (the few who don’t complain about their job). More often than not, these satisfied workers have careers like doctors and engineers. They find their passion because it is highly discoverable and socially acceptable.

The rest of us are left to find our niche passion. If we don’t encounter what we want to do, how will we ever do it? Imagine someone whose destiny is to play the violin, but never takes a lesson. Many are forced to choose their career before they are ready (the second year of college). And so it’s no surprise that so many people give up on finding what they love for a career that pays well, and then drink and watch television to pass the time.

What many people fail to realize is while we don’t know what we want to do, we do know what we don’t want to do. We know when something feels wrong. Unfortunately, we usually ignore this instinct. If you don’t like your job, society tells you to toughen up and get used to it. In actuality, this desire for change is your one and only guide to happiness.

I worked at Microsoft for 4.5 years. I knew it wasn’t what I wanted to do with the rest of my life, and I knew that one day I wanted to pursue an internet startup. I thought Microsoft would be a perfect place to explore various roles and areas. And so I joined the ranks of Microsoft, and waited for my passion to present itself. After the excitement wore off, I ignored my dissatisfaction with my job, and I completely lost sight of what I really wanted to do.

When I was young, I wrote “don’t forget you’re alive” all over the front of my journals. I thought a lot about how teenagers were so passionate, and adults were so boring. I wanted to figure out the moment where passionate teenagers became adult drones. If I could remain conscious, it wouldn’t happen to me. And then I started working, put my journals in a box, and stopped listening to the voice inside me that wanted more.  When I started at Microsoft, it was a great experience for me and I learned and grew. But years later I found myself a business analyst, far from the creator of an innovative product that I wanted to be. Leaving was the most difficult decision I’ve ever made, but I haven’t had a moment of regret and now it seems completely rational.

I’m not saying everyone should quit their jobs and start a company. What I’m saying is that everyone should pay very close attention to the feeling that something is not right in your life. If you’re ever going to find work you love, it’s this voice that will be your guide.

My favorite blog post from Chris Dixon is titled Climbing the Wrong Hill. In it, he asks “How can smart, ambitious people stay working in an area where they have no long term ambitions?” He provides an analogy using a computer science problem where you are placed in hilly terrain, and need to climb to the top of the highest hill. The solution is not to simply go upward, because that would just take you to the top of the hill you’re on, which isn’t necessarily the tallest. Yet even those who know they’re on the wrong hill often feel the need the keep climbing upward. His conclusion: “People early in their career should learn from computer science:  meander some in your walk (especially early on), randomly drop yourself into new parts of the terrain, and when you find the highest hill, don’t waste any more time on the current hill no matter how much better the next step up might appear.”

There are two points here. First, if you haven’t found your thing, you should keep trying new things. It’s never too late to learn something new and make a change. Second, if you know that what you’re doing is not right, stop doing it. You don’t have to know what you want to do – you just need to do something different. Rinse, and repeat.

Looking back on my life, what makes me happy is seeing that I grew and progressed. My life has continuously improved over time, and when it didn’t I made a correction. Each day gets better. My problem at Microsoft was that I didn’t make a change when I stopped growing. Even after you succeed, you should continue to grow and take on new challenges. Anyone just focused on “success” or “winning” will not know what to do with the rest of their life if they achieve it. So focus on climbing your own hill, not anyone else’s, and keep checking your altitude – especially when you think you’ve reached the top.


Overcoming Money Fears

October 21, 2010

When I left Microsoft, I estimated I could live for 12 months on my savings.  I considered LazyMeter a 1-year experiment, and if things weren’t looking good by October/November, I figured I would reluctantly start job hunting.  It’s now mid-October, 10 months after I started, and something surprising has happened: I still have enough savings to last 10 more months.  In fact, after 10 months my savings has decreased by less than $10,000.

Money was of course the biggest thing holding me back from Microsoft.  What I didn’t consider was how much that I couldn’t plan or imagine would happen in a whole year.  Now I know that with a few months buffer, you can always make change.  I remember when I lived in New York City I met a high-paid woman in finance who had just quit her job because she realized she was not happy.  Likewise, I had a friend who relocated to Seattle to work for a large corporation.  She quit after about 2 weeks because she didn’t like it, despite having to pay back the relocation costs.  I thought they were both crazy and irrational for putting happiness first, but I was completely wrong.  We should be seeking happiness, and the money part always seems to work out – you can always find something to get by, like consulting or temping.

I also expected my quality of life to deteriorate during my one-year experiment.  If I hadn’t succeeded by the end of the year, I didn’t think I’d want to continue.  Yet over the last year, my quality of life has actually increased.  I am finally in control of my own life, choosing when to work and what to work on, and when to travel.  Of course I’ve had to make a few sacrifices – the biggest one giving up being a foodie – but a small price to pay for freedom.  And it’s gotten better over time, as I’ve learned to stop worrying about money and just do what I know is right (as I typed this sentence I realized it’s the same advice my grandfather gave me before he passed away).

I’m fortunate I haven’t run out of time.  I am now using the first working version of LazyMeter, and it has already changed my life.  I love how this story has unfolded so far, especially the resulting product.  Once the product came to life, all my fears subsided.  We’re getting very close to beta, the next chapter in our story.

Minimize Failure: What’s Your Worst Case Scenario?

October 18, 2010

My weekly post on Seattle 2.0.

The startup media is biased towards success. Understandably so: it’s the success stories that inspire new entrepreneurs to dream big. Every entrepreneur you speak to appears completely confident they will succeed, but so are their competitors. You know it’s true, but you rarely (if ever) hear anyone say it: if you are working on a startup, you’re probably going to fail.

I get worried when I hear stories of how truly successful entrepreneurs bet everything – how they cash out their 401k, they risk their home, and they max out their credit cards. It makes a great story when the company succeeds (see the Be A Cockroach talk by the founder of AirBnB at Saturday’s Y-Combinator’s Startup School), but what about the entrepreneur who bets everything and fails? They may be just a little upset that they were encouraged to do this. They may be even more upset when they realize they have to return to the corporate life they worked so hard to escape to pay off so much debt.

Do you have a failure plan? Probably not. You’ve been told to have an ‘all or nothing’ mentality when it comes to your startup. You’ve been told success is the only option. That anyone who won’t bet big doesn’t have what it takes. That anyone who won’t bet it all doesn’t believe in what they’re doing.

Dreams and security can coexist. Entrepreneurs can minimize failure by setting up a worst case scenario. If you go to Vegas, do you keep betting until you either win or go broke? No. The best strategy is to set a limit for losses before you arrive at the casino. A startup is a big gamble, and just like a trip to Vegas any entrepreneur should have a predefined limit on how much they’re willing to lose. Will you wager your savings? Your home? How about your marriage?

Those arguing for the all-or-nothing mentality may say “but having so much on the line motivates the entrepreneur to make it work”. I argue that if you know your preset limit, you’ll be just as motivated because you’ll know when you’re running out of time.  Parkinson’s Law says that ‘work expands so as to fill the time available for its completion’. A variation of this law is that spending expands so as to fill the available budget.  Know your budget.

Critics may also say “but investors want to see confidence”. AirBnB was accepted into the Y-Combinator program because Paul Graham was “looking for people that wouldn’t die” (he told the team they were like cockroaches).  If I was an investor, I’d want to see someone who will be realistic, plan long-term, consider all outcome and risks, and not bet the whole company.  Where are the stories of the founders who bet everything and lose?

In addition to setting a limit, an entrepreneur should also actively plan for the possibly their startup will fail. What will you do next?  Will you try again? Will you return to a corporate job? Will you work for someone else’s startup? Based on your backup plan, focus on developing skills and a network so that you’re ready for the next step.

A startup isn’t all-or-nothing. If your startup doesn’t succeed, it doesn’t need to be a failure. The most important thing is the journey and growth from beginning to end. You have control over how things end, both the best and worst case scenarios. With the proper planning you can end up in a better place than where you started, and that’s what matters more than anything.

What do you think? Should an entrepreneur bet everything?


Make It Happen: How to find a Programmer

October 11, 2010

My weekly post on Seattle 2.0.

The number one thing holding back new startups is funding. The number two thing is lack of a technical co-founder. If you attend networking events, you’ve probably met a lot of entrepreneurs with an idea who need a partner to build it. You may be in this situation yourself, or perhaps you’ve already given up. If you have an idea, but no programmer, there are several approaches you can take.

Partner with a Programmer

After they have their big idea, most non-technical founders set forth to find an engineer to form a partnership. If your idea is so great, they will line up to start a company with you, right? Wrong. When you attend an event to find a programmer, you are competing against many others in the same boat, and you are competing against companies offering very high salaries. You are also competing with the programmer doing a startup on their own.

To find a programmer who will simply share equity with you, you need two things. First, you need a very good pitch. It needs to be a vision, not just an idea, and it needs to be inspirational enough to get someone to consider leaving their job and working for free. Second, you need to bring something to the table other than the idea. Many fail at the pitch stage, but almost all fail at pitching themselves. Most entrepreneurs I meet seeking a partner do not include who they are and what they bring to the project in their pitch. They don’t realize that programmers may reject them because they also have their own ideas; it’s not always about money. Ask yourself: what do you bring to the table?

Be honest with yourself about what you can contribute. If you do find a programmer and don’t bring enough to the table, Eduardo in The Social Network is an example of how things can go wrong (ignore the fact that Mark Zuckerberg approached him). He simply did not fit into the company: he had little to add, he couldn’t contribute to the product, and he had a differing vision. At one point, he admits he doesn’t even know how to update his relationship status. It’s no surprise he was pushed out of the company.

Be realistic with the amount of work you’ll each be doing when you discuss equity. If you do find a programmer and do bring enough to the table, another common problem is the non-technical cofounder wanting a lot more equity because they had the original idea. The fact is the technical co-founder will be doing more work at the start.

Be confident with the skills you do have. If you do bring a lot to the table, don’t worry about how you’ll be perceived approaching programmers. It’s good for founders to have complementary skills, and the average programmer you work with doesn’t want to deal with the business side of the startup. You need a programmer, and if you’re the right fit a programmer will also need you. In a post-mortem about the failure of devver, the founders wrote “Dan and I are both technical founders. Looking back, it would have been to our advantage to have a third founder who really loved the business aspect of running a startup.”

I was fortunate to meet a perfectly complementary technical co-founder for LazyMeter. Included in my pitch to him was what I bring to the table: five years of experience at Microsoft demonstrating skills in product management, customer service, sales, marketing, analysis and monetization. My co-founder wanted to be able to focus on the product, and my background allowed him to do so.

Hire a Programmer

There’s a reason funding is the number one thing holding back startups: if you have money, you can hire a programmer. But you still need to know who to hire, and even with significant funding you may struggle to find someone that wants to work with you. Your pitch is still critical, including why they should want to work with you. You need to make them confident enough to choose a lower salary and bet on equity over a much higher salary with a larger company.

If you’re fortunate enough to have money to hire a programmer, spend it wisely. You need to find someone to enter into a hopefully long-term relationship with. But more importantly, you need to find someone who is passionate about your project. Ideally, they’re like a partner and would even prefer it, but aren’t in a situation where they can work for equity only. I’ve seen many presentations and articles warning to never outsource a startup. I agree, but I think it’s just as bad to hire the wrong programmer locally. In fact, I’d rather outsource to someone I felt was passionate about the vision and not just working for the money.

Become a Programmer

What most entrepreneurs with ideas don’t consider is becoming a programmer themselves. It’s intimidating, but you can learn to build at least a prototype on your own. Even if you just develop some skills, you will gain a lot more respect from the programmers you eventually work with, and you may even be able to contribute to the product.

Brad Feld has wrote a series of articles on his blog about Nate Abbott and Natty Zola, founders ofEverlater and participants in TechStars, who decided to learn to program instead of hire a developer. One of my consulting clients made his first fortune 30+ years ago by investing his savings for a computer (very expensive at the time) and figured out the rest.

Anything is possible if you want it badly enough. When you’re looking for a programmer, don’t forget to pitch and interview yourself.  I have a background in computer science, but haven’t coded in years. I am starting a python course at UW in Python because I want to contribute to LazyMeter, and I want to be able to play with other ideas.

Make It Happen: Bring Whatever It Takes to the Table

In conclusion, the most important thing while searching for a technical co-founder is that you bring more to the table than an idea. If you don’t have enough skills to offer or just can’t find the right match, remember that you can always add to what you bring to the table. If you hit a dead-end in both finding a partner and financing, don’t forget you can learn to program and start the project yourself. Entrepreneurs explore all options to make their vision a reality. If you’re stuck, consider every possibility to move forward.


On Failure and Minimum Addictive Product

October 1, 2010

In the startup world, it’s easy to read the success stories.  I’ve been eager to learn more about the many failures.  And maybe there’s something in the air, because this week I have read three honest accounts of failures.

On Monday, XMarks announced they were shutting down.  On Wednesday, Alyssa Royse wrote about making the decision to pull the plug on JUST CAUSE.  And this morning, Marc Hedlund documented Why Wesabe Lost to Mint.

First of all, kudos to these entrepreneurs.  Their honesty shows real courage, and their openness will prove valuable to many others.  It’s not enough to only study the success stories – looking at those who don’t succeed broadens thinking and gives a more complete view from which to make decisions.

For example, I’ve been thinking a lot about the common advice to quickly release the minimum viable product and then quickly iterate.  Over the past few months, we have been pressured to release our product more quickly.  We have pushed back because our minimum viable product is not our minimum addictive product.  We won’t release a product that we won’t use ourselves, and we won’t release a product that’s like others already in existence.  We understand the feedback loop, but can get this from followers without releasing broadly.  Marc Hedlund provided the first evidence I’ve seen against the minimum viable product and being the first to market.

Wesabe launched about 10 months before Mint… There’s a lot to be said for not rushing to market, and learning from the mistakes the first entrants make. Shipping a “minimum viable product” immediately and learning from the market directly makes good sense to me, but engaging with and supporting users is anything but free. Observation can be cheaper. Mint (and some others) did well by seeing where we screwed up, and waiting to launch until they had a better approach.

The moral of the story: consider all advice, get the whole story, question everything, and follow your gut.  There’s a lot of advice in the startup world, but there isn’t a recipe for success.  I keep randomly returning to these lyrics from Wear Sunscreen by Baz Luhrmann:

Be careful whose advice you buy, but, be patient with those who supply it. Advice is a form of nostalgia, dispensing it is a way of fishing the past from the disposal, wiping it off, painting over the ugly parts and recycling it for more than it’s worth.

Update: See this great list of the 25 Best Startup Failure Post-Mortems of All Time.

Update: Andrew Chen talks about the Minimum Desirable Product.  A much more in-depth explanation of concerns with minimum viable product, and a need for what I called the minimum addictive product.