25 Things I wish I knew before moving to San Francisco

I moved to San Francisco 9 months ago from the East Coast bastion of Boston. Despite having experience living in a major US city, I found quite a few surprises coming here.  Some have been great, while others not so much.

If you’re planning the move here, I hope this will help you know better what to expect. And if you already live in SF, this should give you a laugh or two and hopefully inspire you to leave a comment with anything I missed. Consider this the guide I wish someone had given me when I moved here.

It gets cold at 4pm.

On the east coast I got used to it staying warm on a nice day til 10pm. If it was 70 degrees in the morning, you could rest assured that the temperature would be about 70 when you left work that night.  That is not the case here.

Working in SoMa, I’ve found that somewhere around 4pm the temperature starts dropping and so by 5 or 5:30pm it’s 10 degrees cooler outside. A lot of this is due to the fog that seems to roll in around then.

Pro Tip: Be prepared to always have layers with you. A light jacket is your best friend in San Francisco.

Neighborhoods define you.

People take the neighborhood you live in pretty seriously. It’s often a quick way to figure out a lot of what a person values most as SF is a city with something for everyone. Each neighborhood has a unique set of offerings, and pros and cons.  Like any stereotype, it’s not always true, but you will find that yes, there are a lot hipsters in the Mission, bros in the Marina and families in Noe Valley.

Pro Tip: If you’re moving here, spend some time in different neighborhoods before you get locked into living somewhere. (See one man’s opinion here and *update* this is another set of stereotypes for the trendy neighborhoods

If you’ve ever lived in SF, you’ll totally get this, and if not, it’s a pretty good idea of the stereotypes & diversity of neighborhoods:

Bikes of SF by Tor Weeks

Rent is insane.

The first thing you’ll notice when you get here is the sticker shock on rent. This is the most expensive city to live in now and only Manhattan is in the race with them. A studio is now over $2,000 a month in most parts of the city and even with roommates you’ll end up paying $1,000-$1,500 a month for a place pretty much anywhere in town. I just looked up the building I moved into April 1, 2012 and as of January, 2013 the rent is up $700 a month for a 2 bedroom apartment. If you’re wondering why that is, this PandoDaily article does a good job explaining why.

Pro Tip: Finding an apartment is a full contact sport. There’s a lot of important advice on finding an apartment in San Francisco here and a guide for finding roommates in San Francisco here.

Lovely, an apartment listing site, did a great infographic on SF rent prices:

Rental rate rises by Lovely

Update: Here’s a Mid-2013 Look at Pricing of Apartments per Priceonomics.

Cost of living overall is sky high.

Of course these high rental prices are just part of the challenge of living here economically. The cost of goods in my experience have been as high or higher as anywhere else in the country. I’ve solved much of this by moving to buying more online, which is a shame because that means not supporting local businesses.  The most crushing aspect I saved for last though. Taxes here are significantly higher than I’ve experienced anywhere. This means you’re squeezed both on your take home pay and your expenses.

To put it all in perspective, I used to take home about 75% of my pay in Boston and here it’s only 65%. Meanwhile, my monthly expenses have risen almost a third from $2,500 a month in Boston to $3,300 here. This combines to mean despite a significant pay raise when I moved here, I live less comfortably here. I have no idea how anyone who isn’t working in a high tech role that pays an above average salary can live here.

Pro Tip: If you’re moving here for a job, take into account the added costs so you’re sure you get paid a salary that won’t dramatically hurt your standard of living.

There are crazy and cool things always going on.

One of my favorite things about coming to San Francisco has been this fact. It is truly amazing to me how often there are festivals, concerts, and just randomly awesome cultural events going on. From SantaCon to Fleet Week, Yerba Buena to the Academy of Science, there’s not just something for everyone; it’s impossible not to get drawn to something you didn’t expect.  I give huge credit to the city of San Francisco for how often they let streets get shut down, allow for impromptu performances and try to make it easy for people to participate by adjusting public transportation accordingly.

Pro Tip: There’s quite a few great sites out there to find things to do. The best I’ve found are Sosh (my goto site), UpandOutSF and Thrillist. Finding something exciting on one of those sites and asking people to go with you is the fastest way to make friends.

Costumes are a way of life.

“Is that a costume, or is that how you always dress?” is a legitimate question in San Francisco. I can’t tell you the number of times I’ve thought that question when I look at a fellow passenger on the bus or a group of people walking down the street.  San Francisco takes costumes so seriously, we even make up extra occasions for it as Bay to Breakers is essentially a second Halloween for SF.

Also, as a forewarning, some people choose the cheapest costume of all, their “Birthday Suit”, on some days.  As one friend told me, “You’re not a true San Franciscan until you see a naked guy walking down the street.”

Pro Tip: Don’t fight it. San Francisco is one of the most creative cities and it’s because of the self-expression that comes from events like this.

This is a drunken costume party, err, race, across the city:

Lots of homeless, beggars and crackheads.

This is definitely part of the uglier side of San Francisco. Unfortunately, the worst parts of the city for crime are the Tenderloin and Civic Center (as well as some areas of Western Addition and the Mission), which are right in the middle of the city. Market Street and Union Square, which are areas filled with startups and great shops, is unfortunately on the border of those areas. Due to this, going to work or going shopping you’re likely to have multiple people hit you up for money and probably meet a crackhead or two. Luckily, most are harmless, so you’ll find it humorous after while as evidenced by this Yelp thread on “Favorite Crackhead Moments.” 

Unfortunately, this means there are some unpleasant scents in those areas.  Walking down the street you may find yourself playing the game “dog or human?” (note: this is unfortunately referencing what kind of feces is on the ground…or in one case a high heel on the sidewalk in SoMa).

Pro Tip: Learn the streets that include the Tenderloin and don’t walk there at night and avoid any Muni buses that will take you through there on your trip. (See map below and learn about crime in San Francisco with this great site.)

Don't go inside the dotted lines

Don’t wander inside the dotted lines alone

PBR is pervasive, but microbrews rule.

No matter what bar you’re in or store that sells beer, you will always find a hearty supply of PBR, usually in cans. Even Whole Foods sells 30 racks of PBR while only selling 6 packs of everything else.  Of course, being SF, startups have gotten into the game as well with recruiting pitches including a “year’s supply of PBR”:

PBR Recruiting bounty

Now, if you’re not into PBR, never fear. There’s actually a vibrant homebrew community and a number of great beer bars including Toronado and the Monk’s Kettle. California is home to tons of microbreweries so there’s always new beers to try. I personally prefer the microbrews but still see PBR everywhere I go. And if you’re not into beer, the influence of Napa is felt strongly with plenty of great wine options.

Pro Tip: When you’ve spent all your money on rent, you can still afford a beer thanks to the many happy hours and cheap cans of PBR.

An extremely pro-dog city.

If you’re a dog lover or have a dog, this is an amazing city for you. Every neighborhood has one or two parks in it and every one I’ve seen has had sizeable dog-friendly areas. No matter the time of day, you will always find people out and about with their dogs and socializing with others with dogs.  A number of bars I’ve been to have even let owners bring their dogs in when it’s not too packed.

If you want to learn more about the benefits of your dog living in SF, this article captures it better than I ever could:

“Living here has been a revelation when it comes to my dog.

I’m not just talking about the fact that there are hundreds of acres scattered in and around the city where he can romp undeterred by a leash. I’m talking about the fact that the people of San Francisco love their dogs. Where else in the country is there an active dog owner Political Action Committee?”

Pro Tip: Not all landlords allow pets, so if you’re bringing a dog with you, be sure to look into it when searching for an apartment.

Divisadero is the fog line.

San Francisco is known for many things, and one of the most notable is the fog.  It’s a big contributing factor to the temperature drop I mentioned before. The Divisadero is a street running North-South across the city effectively cutting it in half. If you live West of the Divisadero, you’ll see the sun a lot less than your East of the Divisadero counterparts.

Now, this isn’t to say that the whole city doesn’t get blanketed in fog, but if you’re on the West side, right around the time the sun has burned off the fog in the morning, the evening fog is rolling in.

How the Fog rolls in SF

How the Fog rolls in San Francisco

Pro Tip: Don’t let the fog discourage you from checking out the West side of the city. The Golden Gate Bridge, Ocean Beach and Golden Gate Park are all awesome places on the West side.

Palo Alto and Mountain View are farther away than you think.

When I first moved to San Francisco, I was excited to know I had a number of friends who lived in Palo Alto and Mountain View. I figured I’d definitely make trips down regularly for work and pleasure.  I also figured they would come up to the city regularly. In the 9 months I’ve been here, I can count the number of visits on 2 hands. Meanwhile, I do see them in the city on rare occasion mainly because the center of the Silicon Valley universe has shifted back up towards San Francisco.

The Caltrain actually is pretty reliable, and most things in Palo Alto and Mountain View are within a reasonable distance of the stations, but when you look at your phone and realize it’s a 90 minute to 2 hour trip each way, it suddenly feels a lot less appealing.

Pro Tip: If you love living in an urban environment, don’t even consider living in Palo Alto or Mountain View. There’s a reason Google, Facebook and other Valley powerhouses have shuttles for their employees living in SF.

The 3 things you need to know about MUNI.

The MUNI is the bus system in San Francisco that most San Franciscans have a Love-Hate relationship with.  Learn these 3 tips and you’ll avoid some of the biggest pains.

1) Google Maps is never right about what time the bus will come.

- If you need to figure out the best bus(es) to take to get to your destination, Google Maps is great, just not for telling you when the next bus will arrive. Use Rover or NextMUNI for time of the next bus arriving.

2) Half of the buses require you to step down into the steps to get the back door to open. 

- Failing to do this will get the whole bus yelling at you. Avoid the rookie mistake.

3) Chinatown is a bottleneck on any route going through it

- If your bus passes through Chinatown you can be sure that the bus will stop numerous times while passing through, usually delayed by a horde of people either cramming on or fighting to get off. If passing through Chinatown, add time to your trip.

Pro Tip: There are tons of great alternatives for any budget to MUNI & BART: walking, biking, cabs, SideCar, Lyft and Uber.

There are tons of amazing views.

Sometimes the best thing you can do is walk to your destination. This is because there are so many amazing views in San Francisco. I’ve lost count of the number of times I’ve looked around while walking the city and seen a truly breathtaking view.

You can learn where there are particularly great views in this awesome video (Corona Heights and Buena Vista are my favorites):

Of course, the views aren’t limited to the city sky line. There’s incredible nature all in and around the city from the waves crashing on the rocks on Ocean Beach to the sunsets on the Embarcadero to the Presidio view of the Golden Gate Bridge.  It’s definitely one of the best things about this city.

Pro Tip: Alcatraz is not just a cool destination in and of itself, it has some incredible views of the city. Bring your camera and hope for a clear day.

Startup Central is in SoMa.

If you’re interested in startups, the center of all the activity is SoMa, which stands for South of Market St.  With all the public transportation (MUNI, BART and CalTrain) criss-crossing Market Street and SoMA, it makes it super convenient to get to from most areas of the city.

Someone told me that there are over 1,000 startups in the area, and from what I’ve seen, it would not surprise me. Everywhere you look, there’s a sign for companies big and small. It’s not uncommon to find out an entrepreneur you’re going to meet with is in the same building as you.

For those that don’t have offices, many of the coffee shops in the area are notorious for great startup chatter and founders hacking on their laptops at EpiCenter and the Creamery or investors and partnership meetings at SightGlass and Blue Bottle.

Pro Tip: San Franciscans are a heavily caffeinated group that takes their coffee seriously, so try them all and choose your coffee meetings wisely.

SF is a super fit city.

One of the first things I noticed when I visited San Francisco a year ago was how fit everyone was. It literally seems like the population as a whole weighs 10-15 pounds less than their Northeast counterparts. There are a number of reasons for this.

First, the weather is virtually always nice enough to be active and go outside. While the Northeast is freezing and cooped up in their homes buried in snow, it’s sunny and in the 50s here. This makes it easy to stay active year round and helps avoid the dreaded “winter weight” many fight off every spring in colder climates.

Access to healthy food here is also pretty amazing. There are great farmers markets all over the city and with so much agriculture in California, the produce in grocery stores is also super fresh. Restaurant menus are also generally tailored to healthy eating as well. What surprised me most though was that even the Walgreens has produce, so you’re always within reach of something better than a candy bar.

Finally, with all the great weather, everyone seems to find some way to be active whether it be rock climbing, surfing, running, sports, yoga or the gym. Just Google your favorite activity and you’re sure to find a group for it.

Pro Tip: Joining a league or taking a fitness class is a great way to make friends. I made quite a few quick friends from the soccer team I joined and the ultimate frisbee league I play in.

If you’re a foodie, welcome to heaven.

A friend told me San Francisco has so many restaurants the entire city could eat out at the same time and be seated.  From what I’ve seen, I’d believe it.

Seriously check Yelp. It’s truly stunning the wide variety of food available. With so many options, there’s little reason to eat at the same place too many times.

A few of the tasty things you’ll find in SF (via Let’s Eat SF)

Pro Tip: Great places to eat and drink are a great conversation topic for any San Franciscan. If you want to move beyond Yelp and Foursquare Explore, just ask a local for a recommendation.

The 3 hour time zone difference is a big deal.

Having lived on the East Coast my whole life, I got very used to how much life revolves around the EST time zone. Sporting events, major news (like the State of the Union) and most television is optimized for EST. Being 3 hours behind can be difficult.

Being a big sports fan, this was a big adjustment. The first time I realized a Celtics playoff game was starting at 4pm was a sad day as there was no way I could watch the game until at least half time because of work. Meanwhile, NFL Sundays will never be the same as 10am kickoffs is something I don’t think I’ll ever get used to. For those of you playing Fantasy Football, you may find yourself setting an alarm to make sure you’re awake in time to check injuries and set your lineup before the 1pm EST games.

Most importantly though, is the adjustment with family if they live in another time zone. I used to call my parents at least once or twice a week, especially to talk to my father if I needed business or life advice in a pinch. Unfortunately that’s a lot harder when you realize that if you wake up at 7am, it’s already mid-morning for them. Meanwhile, after work, if it’s 7pm here, it’s already 10pm and my parents are getting ready for bed. Bummer.

Pro Tip: Build a routine around connecting with anyone you want to keep in touch with on the East Coast. It will help fill in for all those moments you’re about to call someone and you realize the timing won’t work.

Watching sports matters a lot less.

With such great weather, so much to always do and the time zones throwing off game start times anyways, it’s little surprise that sports aren’t the center of conversation like they are in much of the Northeast.  In Boston, even women that hate sports have to pretend and wear pink Boston gear and watch the games. That definitely doesn’t happen here.

The good news is, if you have a team you love, there’s a “team bar” for just about any team in any sport. As a Steeler fan this has been great as I know there’s a place to go clad with the black and gold and the game on.

Pro Tip: If you’re used to bumming around inside on Sundays watching football, expect for that routine to change to brunch (a SF favorite activity) or any number of outdoor activities.

Everything is taken to the extreme.

San Francisco is a city with something for everyone. The interesting thing I found is how that is taken to the extreme. Whether you’re a hipster who will ride your fixie with your year-round (not just Movember) mustache or a bro in the Marina hulking on creatine, it seems everyone in a group tries to take it to the furthest point. In the most extreme case…look up the Folsom Street Fair (NSFW warning: graphic / sex-related).

In my daily life this has led to me noticing polarity like:

  • In fashion, either you’re super dressed up or you try very hard to look like you’re not trying at all in your skinny jeans, sandals and a t-shirt you wear every day.
  • Either you wear a jersey of your favorite team and go to the team bar to watch and talk about the game, or it doesn’t matter.
  • If you have a startup, your pitch probably includes how you’re going to not just build a cool business, but change the world in a massive way.

Pro Tip: Use this to your advantage and take one of your interests to a deeper level when you get there. You’ll likely meet others with the same interest who can teach you new things and be a friend. 

You’ll turn into an early adopter even if you weren’t one before.

As a city, San Francisco is at the forefront of a lot of innovation. Even our trash program is progressive as it tries to set us on a path for zero waste by 2020.  More specifically in your day to day though is all the new products gaining new adoption and hype every day here.

A common topic of conversation whether at work, at a bar or just out and about is always the latest the apps people are using. You’ll try them out and have an opinion or be left in the dust. All this adoption has an added benefit of meaning that San Franciscans often gets the first look at apps other cities can’t even use yet (exp: Sosh, Lyft, SideCar, etc).

Your iPhone screen may start looking like this after a few months:

Pro Tip: Try a couple new apps every week and if you’re looking to spark conversation, ask someone if they’ve tried any great apps lately.   

All the best tech startups are at their best here.

With all this great early adoption, it’s not that surprising that most of these startups are at their best here.

The most impressive to me is definitely Yelp.  It’s amazing in SF. I always use it and hear tips constantly after never using it in Boston. It seems like every store and restaurant has hundreds of reviews and there are a crazy number of Yelp Elites.

Pro Tip: If you tried apps like Foursquare and Yelp in other places and weren’t impressed, they’re worth another shot here.

Working in tech is the norm, not the exception.

Coming from Boston, startups feel almost like a secret society that flies under the radar; most of the city has no idea the hundreds of early stage startups there nor realize giants like Constant Contact, Kayak, and VistaPrint are all Boston companies. Meanwhile, here, no matter what you’re doing, those you meet will almost always be in finance or startups.

Like in Hollywood a few hours South, if you’re trying to “make it” (in our case, in startups, not writing/acting/directing), this is the place to be. There’s a 98% chance the person next to you in the coffee shop with the laptop open is working on their own startup or someone else’s.

Pro Tip: If you listen carefully to the conversations around you at the coffee shops here, you’ll hear tech gossip without even having to read TechCrunch.

A common sight at San Francisco coffee shops

People love novelty and new experiences.

This was actually one of the most surprising adjustments I had to make in common to San Francisco. In Boston, people are all about routine; you go to your favorite bar or restaurant with a certain group of friends like clockwork. If you find something you like, it quickly becomes the old standby and everyone is excited to recreate that experience.

In SF, it’s all about trying new things. Just because the last place you went was awesome doesn’t mean you’d like to go back. Instead,everyone looks for unique things to do and the fastest way to make friends is to suggest something unique & awesome to check out.

Pro Tip: With great weather pretty much year round, you can safely assume every weekend you’ll be able to get out of your apartment and experience something new. Cabin fever is a foreign concept in San Francisco.

Tons of awesome lies just beyond SF’s borders.

It’s easy to get lost in exploring San Francisco, but what really makes the city great is what lies just beyond. No matter what you love doing or your favorite climate, there’s great places to visit within a few hours drive of San Francisco.  You can snowboard or gamble in Tahoe, taste wines in Napa, rock climb or hike in national parks, mountain bike in Marin, or sail the bay.

Pro Tip: Oakland gets a bad rap, but there’s tons of great concerts and other events there worth checking out.

Come with an explorer’s attitude.

San Francisco is a city for new adventures and boundless opportunities. There’s great websites, apps and friendly locals who can help you take advantage of all there is to offer. With all the personality of the city and each individual neighborhood, there’s new things to discover and appreciate every where you go.

 

San Francisco native? What advice do you have for newcomers?

Update: Jacob, a native San Franciscan wrote a great post from a veteran’s perspective that’s well worth the read: http://sfloveaffair.wordpress.com/2013/01/19/34-on-things-you-should-know-about-san-francisco/

Update 2: With rent skyrocketing, if you want to save money, finding an open room is a must! Unfortunately, it’s super competitive with hundreds emailing for one room. You can learn to stand out from the crowd with this great guide on finding roommates in SF.

Special thanks to Zach Cole for help with this blog post. If you’re interested in startups and hiking, check out his site here: http://startuphike.com/

Lessons in Innovation from the Biographer of Jobs, Einstein & Franklin

Walter Isaacson has written the biographies for some of the greatest inventors of the last 300 years in Ben Franklin, Steve Jobs and Albert Einstein. He spoke at the National Book Festival in Washington DC and I serendipitously stumbled upon his speech on CSPAN2. It was so amazing, I wanted to share it all with you as I found it is on Youtube here:

I highly encourage you to watch the whole thing, but I wanted to highlight two things that stood out to me.

Simplicity is a spiritual quest.

Especially in the tech scene and product world, we talk about simplicity like a Holy Grail of sorts and with good reason; a truly simple product has many advantages in the market and a strong likelihood of success. I think Isaacson captured this very well in his talk when he said,

Walter Isaacson on Simplicity

Often I find myself getting caught up in building something that is infinitely flexible and covers a million use cases and it makes me forget the essence of what I’m trying to build.

Spirituality comes into play because this requires faith; I have to believe that by sticking to the core of what I’m doing and ignoring some attractive features, I’m building the right product. It also reminds me of the effort required to get there; the first few iterations are unlikely to get to perfection. Instead, it is the dogged pursuit of simplicity that helps find the essence of what I’m really trying to create.

Tying these concepts together, and sharing how Einstein and Franklin thought about simplicity in addition to Jobs is a fascinating insight only the biographer of all 3 could do.

You have to be YOU.

After a question from the audience at the very end of the video, Isaacson covers the most important lesson I think we all need to remember as we read all the tech blogs and study successful people:

“Don’t try to just copy any one of them. Biography is understanding our world, our values and how you might apply them in your life.”

No matter who I’m studying or learning from, I try to see what I should learn from them to build on who I am, not try to be them. I will never pull off the design instincts and asshole of Steve Jobs nor the curiosity and mathematical brilliance of Einstein, but I know I can learn skills and approaches from them that will make the best version of me.

The secret weapon to bringing change to your life: Simple Triggers & Routines

Many of us want to change and improve ourselves in little and big ways.  Maybe we want to lose 10 pounds, drink less alcohol, spend more time with family, or just get more out of every day productively. With New Years Resolutions set to be attempted in the next few days, it’s a great time to think about how you’ll bring about the change and not just the results you hope for.

The key to to bringing about any change in your life is developing new routines and simple triggers for those routines. 

To understand why, we need to take a step back and understand will power and motivation via the Elephant and the Rider.

The Elephant and the Rider

In the Happiness Hypothesis, the author uses an analogy of our psyche being a combination of an elephant and a rider. The elephant is impulsive, emotional and can often outmuscle the rider, which is our more thoughtful, logical selves.  The key to this analogy is that a rider can only steer the elephant in a direction it doesn’t want to go for a short period of time. Then the rider becomes exhausted.  This is what happens when after a day of choosing healthy foods, you find yourself attacking the desserts late at night.

So how does anyone bring real change to their life?

If the elephant can eventually exhaust the strength of the rider from trying to steer them in a new, positive direction, then how does anyone successfully create change? The key is routines with simple triggers. The elephant loves routines.

The beauty of this analogy is how neatly it works with actual elephants in the circus. When elephants are young, they’re feisty and are often tied to giant posts to hold them in place. The elephants always fight hard to break free, but never do. Eventually, they give up and get used to it.  When they’re older, the rope that previously tied them to a post can now be simply left on the ground. The older, stronger elephant will not move due to becoming accustomed to the routine.

Your elephant responds to patterns.

If you want to bring about a change in your life, like going to the gym, create a routine around the act of going to the gym. Set out your gym clothes the night before you plan to go to the gym and schedule it like any other meeting on your calendar.  Hide the cookies you struggle to resist and put healthy snacks you like within closer reach.  Think about what the triggers are for habits you want to break and try to replace them with new, positive things you want to do.

A trigger and routine that worked for me

When I was in college, I took a course called “US History 1820-1877″ which included the requirement to read a massive, tiny-font 375 page book on the US Senate between 1840 and 1865.  Like any college freshman would do,  I procrastinated so that 2 weeks before my final paper was due on the book, I hadn’t read more than the first 10 pages. This meant I needed to read about 35 pages a night to have time to finish the book and write the paper.

To accomplish this, I set a routine with some simple triggers: each night, after my roommates went to bed, I sat down on the couch in our living room, put on headphones and started listening to the first two Linkin Park albums (please don’t judge). This routine worked perfectly and got me through the book and my paper.

Throughout college, even after I moved on from music like Linkin Park, I still found myself using the album to trigger focus and getting work done. To this day, I still feel heightened focus when listening to the albums and use it from time to time when I have something I really need to get done.

But what if I hate always doing the same thing?

I’ve been eating peanut butter and jelly sandwiches every weekday since I was in high school. Not everyone wants to have that boring a routine. Fear not.

The key is setting up patterns for good behavior even if you vary it. Maybe you decide you’d like to take a fitness class and do cardio on an elliptical on different days. You can use the same trigger of setting out your clothes the night before for both.  If you want some variety in your new healthy diet, you can always mix up the fruit and nuts you get to replace the unhealthy snacks you had before.  Most importantly don’t let fear and excuses get in the way of positive change.

Final tip: Start small

Besides not recognizing the power of routines, the biggest mistake people make is trying to do too much at once. You can’t overhaul your diet, start working out 6 days a week, get up an hour earlier and start making extra time for family all at once.  Not only will your rider get exhausted from all the change he’s trying to coax the elephant to try out, but it will be too much change for the elephant to handle emotionally.

Because the elephant likes routines so much, breaking them can be hard; you can shock your elephant if you change too many things at once. However, if you slowly make changes like perhaps starting with a few modifications to your diet and starting a class at the gym a couple times a week, you’re much more likely to succeed in making those changes. Once you’ve achieved those, you might even have extra energy to motivate you to additional goals which you can then tackle building routines for.

As you set out to bring about change, New Year’s Resolutions or not, remember to focus on creating new routines and triggers to give yourself the best chance at succeeding.

Further Reading

If these subjects are interesting to you and you’d like to learn more, I encourage you to check these books out:

The Happiness Hypothesis will teach you in depth about the Elephant and the Rider concept and the psychology and motivations of humans.

The Power of Full Engagement will teach you how to raise your productivity and have a happier life at work and at home from authors who have trained Fortune 100 CEOs and championship caliber professional athletes.

My Philosophy on Reading Books

I read a lot of books. For the past 3 years, I’ve averaged finishing a book every 2-3 weeks (thanks to this post inspiring me). Through all this reading, I’ve learned a tremendous amount thanks to a specific philosophy I’ve had on what I choose to read.  Since I just published the organized list of all the books I’ve read and recommend, I wanted to explain how I arrived at this list. These are my strategies when choosing how and what I read:

  1. Only read for purpose – I read books on subjects I want to learn about (i.e.: non-fiction only), so reading is about education not relaxation or escape for me.
  2. Stick to highly recommended books – I ask trusted friends, mentors and observe leaders in tech for books to read. I hate wasting time on a bad book, so I work hard to ensure anything I read isn’t a waste. This is why I include a section in my books list on books not to read.
  3. Read to solve current problems or satisfy current interests – This helps me quickly apply whatever I read to challenges I’m facing in my work and/or personal life.
  4. Write in the margins – If I don’t write down the ideas sparked in reading, I won’t remember nor apply them. It also makes it easier to revisit concepts I found interesting in any book I’ve read.
  5. Read in small bites – I read when I’m on public transportation, which generally means 15-30 minute bursts. This ensures I have plenty of time to think about each concept I read about and absorb as much as I can. Credit to Leo of Buffer for expanding on this subject here.
  6. Share - When I learn interesting concepts or a great book, I share it. The subsequent discussion with others leads to even more learning.

How do you decide what books to read? What motivates you to read?

Why you should take your 20s seriously

“Don’t take life too seriously, you’ll never get out alive.” – Van Wilder

It seems like the prevailing advice today for anyone in their twenties is to live their lives free of any commitments and as independent and undirected as possible.  As a workaholic entrepreneur since I finished school, it never really resonated with me, but even I have found myself prioritizing based on the fact that my 20s are unique time I can do things I wouldn’t be able to any other time in my life.

A friend recently recommended I read The Definining Decade: Why your twenties matter – and how to make the most of them now. After reading it, I realized the importance of my twenties to a degree I never had and it has changed how I plan to approach the last few years of my 20s.

Written by a clinical psychologist, the book hits on all the key aspects of your life: Work, Love and your Body. There are many great takeaways, but the 3 biggest that have stuck with me are:

1) Your 20s lay the groundwork for success in the rest of your career.

Whether you’ve spent too much time as a bartender or waitress or in tech living in your parent’s basement as you “work on your startup”, you could be preventing your life from moving forward in a way that will make you successful and happy in the future.

Maybe Starbucks is enough to be happy now, but can you raise a child with that pay? More importantly, do you want to be doing exactly what you’re doing now in 10 years? If not, does your current job get your foot in the door?  If you aren’t Mark Zuckerberg, maybe you should think about how to build a career in a startup as opposed to being a young, fledgling founder forever.

No one starts at the top. It starts with a dues-paying low level job where you excel and get more and more opportunities. I had a master’s degree and still had to start with a part time internship to get my foot in the door in tech. That internship led to the person I interned for getting me a full time job at a startup they were on the board of. The founder of that company then introduced me to Hiten Shah as a mentor and now I run product for his company, KISSmetrics. This is how most successful people I know have built their careers, and it always starts small.

Lesson: Don’t put off starting to build a career. The sooner you start out in an industry and role you like, the sooner you can grow into a satisfying career.

2) Statistically, women need to have all their children by 35.

According to the author, a woman’s ability to get pregnant plummets starting in her mid-thirties. To make matters worse, the odds of a miscarriage for a woman over 35 is one in four.  This is a scary statistic that brings images to my mind of a couple struggling to get pregnant only to lose their child during pregnancy. No one wants that.

The thought of a family has been far from my mind all through my 20s. I’ve put my career goals ahead of everything else.  At the same time, I’ve known I do eventually want to have a family. Realizing these statistics has led me to better understand the choices I make and the time I’m working against. It now makes a lot more sense why there’s so many founders in their early 30s that have started families.

Lesson: If having a family is part of your life’s goals, you probably have less time than you think. If you’re a guy that wants to marry a woman relatively the same age as you, the clock is ticking on you just as much as it is for her.

3) Your brain finishes forming in your 20s.

I always thought your mind was formed as a child and that by the end of your teens your brain was probably what it was going to be until the decline began in your 30s or 40s. As it turns out, your frontal cortex goes through great change in your 20s before it is set more permanently in your 30s (imagine wet concrete hardening). Per Wikipedia,

The executive functions of the frontal lobes involve the ability to recognize future consequences resulting from current actions, to choose between good and bad actions (or better and best), override and suppress unacceptable social responses, and determine similarities and differences between things or events.

As a person whose goal is build a massive company, I realize I need to develop as many of the skills I need to lead such a company now, because in a few years it may be difficult or almost impossible to grow in the ways necessary to handle the role. As I hear about founders that can’t (or don’t want to) run a company once it reaches a certain size, I think about the challenges of scaling yourself and the development required.

Lesson: Whatever your career and life goals, realize that the skills you develop and the personality you forge in your 20s will determine many of your abilities the rest of your life.

Few books I’ve read have led to as much personal introspection as reading this one. If these concepts interest you, I highly recommend you check out: The Definining Decade:

The Fallacy of Chasing Startup Ideas

Over the past week, I’ve caught up with a few friends that are in the process of searching for their next startup idea. One is an EIR, another a founder looking for a new idea for their startup. Less than a year ago, I was on a similar quest.  As much as the passion to build a company is a noble cause and one I deeply relate to, I don’t think you can find it by broadly searching for the right idea.

I believe there are only 2 ways to find a great startup idea: Experience and Passion

1) Experience

You’ve worked in an industry for years. You know all the inefficiencies in the market and how terrible the existing solutions are. You are the target customer or you know them because of regular interactions.  Because of your experience you have the connections to land your first customers with relative ease and likely already know what the Minimum Viable Product would be.

2) Passion

You may not know the industry well, but you’re so fired up about the idea you can’t sleep at night. You want this solution to exist, you know the world is not complete without it and you’ll run through walls to make it happen. This fire also is likely to give you a level of understanding of the end user that will translate to a great product you want to use.

So which is more important?

If you’re starting a B2B startup, Experience is more important as it will help with those key early sales. For consumer startups, Passion is more important, since often new tactics are needed that industry experience would not help as they’d be outdated.  Ideally, you’ll have both as it will help get your venture off on the right foot and have the wherewithal to survive the trough of sorrow.

The problem I found in searching for a startup idea for 9 months and what I think my friends will struggle with is that without Passion for an industry nor Experience within it, you’ll be unlikely to magically come up with an idea on your own. If you’re really determined to start a company despite this, then your best bet is to find a founder to co-found with who has Passion or Experience (the best startups have both) or join a company you can learn a lot from in a high impact position(what I did by joining KISSmetrics to run product).

Should founders care about their employees’s personal lives?

{Note: this is part of an experimental series of short posts. My goal is to spark more discussion and post things that aren’t fully thought out 1,500 word mega-entries I usually post.}

This tweet got me thinking today:

There are assholes and then there are people who have moments when they act like one. In a startup there is no room for the former, but we all have moments where we may be the latter.

I’ve found myself in the latter bucket a number of times since I got to SF because of the stresses I’m experience in adjusting to a new environment and starting over socially. Try as I might, I haven’t always been able to leave issues at home and just be my usual working self.  Fortunately, Hiten and others have been understanding of me. Team dynamics are hard to get right and when someone is being an asshole, it’s poison to the environment. That’s why I posit it is important for founders to care about their employees personal lives.

Of course, none of this is limited to just assholes; employees underperform for a multitude of reasons in a variety of ways.  If you have a connection with your employees beyond their job description, you’re likely to find out what may be the cause of an issue. And you wouldn’t have to be their therapist to be helpful and understanding.  At the least, you can help patch up some relations around the company by telling others on the team to cut that person some slack (without necessarily going into specifics) and making some recommendations of what the employee can do to help themselves.

What do you think?

Should founders care about their employees’s personal lives?

SF Startup Survival Guide: How to Find an Apartment in San Francisco

Congratulations! You’ve taken the plunge and decided to move to San Francisco for your own startup or to join one of the hundreds (thousands?) here. Making the decision to move may have been difficult, but nothing compared to all the hassles and headaches of moving to this city.

Having just gone through this and spent a significant amount of time asking friends for advice on making the move, I’d like to share the best advice I received and what I learned myself.  For reference, most people take months to find a place to live and move in. With the tips below, I found an apartment and moved in within 2 weeks of landing in SF. (Update: If you want to save a ton on rent and find an open room instead of renting a new place, check out this guide to standing out when emailing about roommates and open rooms)

How to Find an Apartment in San Francisco

1) Move Yesterday.

When I started looking at rental prices, I was shocked. Prices for real estate in San Francisco are insane. Seriously. Studios in non-prime locations go for anywhere from $1,400-$2,000 per month, while two bedrooms are all in the $2,500-$3,200 range and rising.

I moved into a 2 bedroom in a 20 unit building in Pacific Heights and met a neighbor who moved in just 2 weeks after me and he is paying over $100 a month more than I am. This will only get worse after the Facebook IPO and as major growth companies like Twitter stay in San Francisco as they scale while others add shuttles to take you to and from the city for work. So if you’re going to come, come now or pay later (literally).

  • Pro Tip: A coworker of mine at KISSmetrics spoke with a realtor that says we’re on the same track for real estate prices as the last dot com bubble. When that happened, studios started going for over $3,000 per month. It’s going to get worse before it gets better.

2) Find a roommate.

Realizing the crazy apartment prices made finding a roommate a necessity, I immediately emailed everyone I knew that lived in the Bay area asking if they knew anyone with a spare room or was looking for a roommate. I also blogged, tweeted and posted on Facebook.

While I only got a few responses, they proved invaluable; I got a ton of advice about the city as well as some good leads. Not only did their intros lead to my current roommate, but I was able to find a replacement for myself back in Boston.

It can be extremely competitive in the open market, so use your network. Look up any of your long lost Facebook acquaintances, sorority sisters, old coworkers, etc and let them know you’re looking.  You’ll get a low response rate, but if you stick with it awhile you’ll get some leads.

You can also try looking on Craigslist although you’ll find that you’ll be interviewing for any spots posted against 50-100 other people. If you want to beat that crowd, then my this guide to emailing open rooms and prospective roommates is a must.

  • Pro Tip: Don’t just ask friends who live in the Bay Area. Look for people in your town that know others out there. It was a friend of a friend that helped me find my current roommate.

3) Learn the neighborhoods and narrow your search.

Once my friends started offering to help me look for roommates, their first question was, “where do you want to live?” I really didn’t know, but since San Francisco is a 7 mile by 7 mile city I really had to narrow it down for them to be able to help me.

I soon learned there’s a massive difference between living on the eastern side or western side of the city (it’s foggy and less sunny west of Divisadero St). There’s also huge differences from neighborhood to neighborhood as you are unlikely to find someone interested in the Mission, Marina and Sunset for a variety of reasons from lifestyle to commute to cost.

To narrow it down, I first eliminated everything that wouldn’t be easy to commute to work to; I use public transportation, so I limited my locations to places I could get to work in SoMA (aka- South of Market) in under 30 minutes by Muni or BART (the public transportation lines in SF). Next, I asked everyone who had any knowledge of SF to tell me what neighborhoods were like. In particular Zach Cole deserves a big shout out for giving me a breakdown of virtually every neighborhood.

4) Secure a short term living arrangement.

I knew there was no way I could find an apartment without being there to see it and get a feel for the neighborhood so that meant moving to SF without a place to live.  One of my friends I reached out to about moving out west happened to have a spare bedroom in her & her fiancee’s apartment, and they were kind enough to offer me a stay while I searched.

It was pivotal for me because I knew I didn’t have to worry about the safety of my things when I got to SF and I had two welcoming, friendly faces waiting for me when I landed. The latter cannot be overrated as I had just left all my friends in Boston behind.

If you can’t find any friends or coworkers to crash with, your next best bet is AirBNB. There are quite a few tech people that list their couches and spare rooms on there. You can generally find a couch for about $50/night or a bed for $100-$150 a night.  You can also look for short term Craigslist options, but it’s tough to find something that lines up perfect with your start date.

  • Pro tip: Move mid-month so that you can look for places starting the first of the next month; I moved out on March 14th and moved into an apartment then starting April 1st.

5) Pack your things.

Everything I’ve listed thus far were things I did before moving to San Francisco. With these things in order it was time to figure out how to move my clothes, bedroom and other personal belongings.

To save money, time and keep the peace with my roommate who wasn’t thrilled I was moving, I left virtually everything in my Boston apartment except for some cooking items and items from my bedroom.

You really only have 4 options when moving across the country under these circumstances (ranked in order of most to least expensive):

  1. Moving company – Pay a professional moving company to load up your things and take them out west for you.
  2. Relocation cube – There’s Pods, Door2Door and UPack as options. All will drop a container at your old apartment, then move it across the country and hold it in storage until you tell them when and where to deliver it.
  3. Uhaul – Drive across the country with a truck load of your personal belongings. Don’t forget the cost of gas and lodging for the drive!
  4. Throw away everything – I know a few people that took only what fit in suit cases and bought new stuff when they got to SF (Hello Ikea!).

I ended up going with the ABF UPack and couldn’t have been happier with them. They have great customer service, a sturdy, safe container and are about half the price of a Pod. Door2Door is an awkward wooden box that you have to wonder if it will fall apart or leak in the rain.

  • Pro Tip: If you go for option 1) or 2), get quotes from multiple sources then play them against each other.  I talked the UPack sales person down an additional $200 at the last minute with a Yelp discount and the offer to “Close right now and not call anyone else.” 

6) Scout the neighborhoods.

After getting to San Francisco, I met with my potential roommate, Chris in person. Once we realized we could get along, we agreed to scout the neighborhoods we were both interested in. We met up on a Sunday afternoon and drove around all the neighborhoods on our list and talked about what we liked or disliked.

We found that seeing the neighborhoods brought insight our friends alone couldn’t provide. After the driving, we were able to easily cut our list down from 6 neighborhoods to 3 in one specific section of the city.

  • Pro Tip: Every neighborhood in San Francisco has slightly different architecture, so it’s surprisingly easy to note what neighborhood you are in based on architecture and knowing a few key streets in the city.

7) Get your blood sample ready.

When I was getting ready to move, I noticed the list of paperwork to provide your landlord was pretty absurd compared to what I was used to in Boston. It doesn’t actually include a blood sample, but you do need just about everything else:

  1. Reference from a past Landlord
  2. List of past landlords with contact info for the past 2-3 years
  3. Copy of your full credit report (I used freecredit.com)
  4. Pay stub or offer letter to prove you can afford the apartment
  5. Check in hand to pay for first month, last month and security deposit

Yes, this is a lot, but if you have it in hand, you’ll impress the landlord and avoid getting passed over; there’s apparently a law in San Francisco that says a landlord has to take the first qualified applicant for their place. By having all this paperwork, you’ll be qualified.

  • Pro Tip: My roommate and I put our paperwork in a Dropbox folder we shared. This made it handy if we ever needed to print emergency copies and it allowed both of us to look at the other person’s report and see that both of us pay bills on time and have good jobs.

8) Search like a Pro.

On Sunday Chris and I drove around SF to pick what neighborhoods to focus on in our apartment search. That night, we started looking.  Craigslist is weak compared to the real tools you can use: Padmapper and Lovely. I love Padmapper more because of some of their added search map features, but they’re both great.

These two services let you pick your neighborhoods and most importantly, get alerts when any property is posted to quite a few different rental sites including Craigslist.  This gives you a fighting chance of being one of the first people to see a place (basically the only way to get an apartment). You can also check out walking scores, crime rates and some other cool factors that can help you in your decision making process.

  • Pro Tip: Take your email to the landlords about available apartments seriously. This is a sales pitch you want to nail. Optimize for making you and your roommate sound like attractive tenants without lying. If you’re looking to impress someone with an open room, this can help.

9) He who hesitates, is lost.

Chris and I had alerts set for Nob Hill, Russian Hill and Pacific Heights. We saw a couple of options that night and emailed to set up showings.  We set the first up for a 10:00am showing Monday morning.

As I was waiting for Chris to meet me that morning, I was accosted 3 different times by crackheads. Not a good start. Once we got in the apartment, we were further unimpressed. Amateur hour on the renovations showed poorly laid carpet and a cabinet where they messed up their dimensions and had cut a giant hole in the back of a cabinet. The landlord also didn’t speak very good English. This was not going to be the place.

As fate would have it, I found a padmapper alert in my inbox while Chris and I were talking about the poor apartment we had just looked at.  The new listing, in a nicer area, had a phone number to call for a showing. We called saying we were 15 minutes away and would love to see it right away. The landlord agreed to meet us and 40 minutes later we were signing the paperwork on our new apartment (while her phone was ringing off the hook with more people interested).

  • Pro Tip: NEVER go to an open house for an apartment. You will be competing against as many as 100 other people.  Some sketchy landlords will even try to get everyone to pay an “application fee” so they can squeeze money out of all the people coming in addition to the rental fee that will invariably be bid up with all the frenzied lookers.

10) Tough Market != Impossible Market.

The important thing to keep in mind is that everyone I know eventually found a place. Many of my friends that have moved here learned hard lessons about avoiding open houses and the need to have all that paper work ready in advance, but now that you have this post, you can avoid those pitfalls. In the end most of my friends are now in places they really like. With a city this size there’s something for everyone and always places coming on the market.

Realize that apartment searching here is a “full contact sport” as one of my friends described it and commit to putting in the effort to find your ideal place. If your employer gets annoyed about missed time looking at apartments, just remind that how much more productive you’ll be when you stop worrying about this and sleep in your own bed at night.

  • Final Pro Tip: Choose a place you could see yourself living in for a few years; with the current tech boom, prices are only going up for the forseeable future. If you’re like me, you can barely afford the rent now, so you won’t be able to afford to move when your lease is up in a year.

What advice do you have for people moving to San Francisco?

The Secret to Getting Any Job You Want: Focus

Whether on the subway, at home with family for the holidays or talking with friends, I often hear the same thing:

     “It’s so hard to find a job right now…”

     “I applied to 100 jobs on Monster.com and heard nothing!”

     “I applied to every job I could find and I couldn’t even get a phone interview!”

In the last 4 years, during a recession that crushed our generation in the employment market (over 17% unemployment for Gen Y) I have landed three different, awesome jobs. What makes it particularly interesting are the following facts:

  1. Each job I applied for was a reach based on my existing skills.
  2. Each job was the only job I applied for at the time.
  3. Each company ended up giving me a different job than I initially applied for, but that was an even better fit than what I started out going after.
No matter how hard you focus on getting a job, there are still only 24 hours a day. I have the same constraints as you. The problem is, when you apply for 100 jobs, you’re spreading your energy across 100 companies, while when I apply for one job, I’m focusing all of my energy on one company. That concentrated energy gets you noticed and gets you the job. How is this possible? In simplest terms, it’s all about focus.

Let’s look closer. I’m sharing all my secrets for getting the perfect job:

Step 1: Choosing the right company.

There are thousands of companies out there and especially as our economy finally recovers, many of them are hiring. For those of you who applied to 100 jobs, you know this is true.  What really matters though is picking one company that you really want to work for.

It’s up to you to decide what matters most to you. Is it location? Company size? The market they work in? You want to choose the two or three most important things and use that to filter the companies you see that are hiring. Then you should dig into the company closer and see who gets you excited. Every company has an “About” page full of information about who they are. Keep searching until one of them stands out for you. If you’re going to put a ton of effort into pursuing one job, then you should make sure it’s a job you really want.

Step 2: Plan your attack.

Applying for a job is a lot more than writing a cover letter and submitting a resume. If you are going all in on one job, you need to do some serious prep.

Start by tearing apart their website. Then Google them. Learn everything you can about them. Pretend you have to give a major presentation for a class about them. Next, research the people you may be working with; if you’re a designer, look up other designers at the company, if you’re in HR or marketing, look at those departments specifically.

Step 3: Fire the first shot.

As you do your research on the company, see if you know anyone who works there or if you have a close friend/mentor/family member who knows someone there. If they do, ask for their help in getting an introduction into the company. Ideally, you want it to be someone in the department you’re applying to (if the company is big enough to have departments), but work with whatever you have.

Completing this step means getting an intro to someone in the right department. The real trick to succeeding in an interview is getting past the mess of general applications.  An intro directly to the person hiring is how the pros get it done; they end up at the top of the proverbial resume stack…unlike the “spray and pray” kids from Monster.com that never get past the inbox.

Step 4: Follow up with value.

Now that you’ve submitted a great resume and cover letter tailored to the company and target job along with that intro to someone in your target department, it’s time to take your game to another level.  You’re now going to create content to add value to your (hopefully) future employer.

The goal with the content you create is to show competence in the job you hope to do for them and also show an understanding of their company and their present challenges. If you’re a designer, perhaps it’s feedback on the design of some of their site or a proposed new design for something they have. If you’re a developer, you could make a small app with their API and include feedback on how they could make the API better.

If you’re on the business side, try submitting feedback on their product from a user perspective or even gather some insights from their market that would be valuable to your target supervisor.

Another great trick I’ve used is to literally tell them what I’d do if I had the job.  I once submitted a 7 page document full of ideas of how a startup could engage its community and build buzz. It made for great conversation fodder in the interview and made me stand out against candidates who had more impressive work experience than I did. Startups love do-ers and this showed I was someone who got things done and had my own initiative.

Step 5: Double down and be persistent.

The great thing about submitting all this content to your target employer is that when you’re following up to find out where you are in the interview process, you’re not just bugging them, you’re sending them something of value. Each time you follow up in the process, try to have something of value to give them along with the ping. It will keep you on their radar and impress them with your persistence.

Do you have time to follow up with potential employers when you submit 100 resumes? Obviously not, which is why your new tactic of following up and adding value will stand out so much.

Step 6: Crush the interview and close.

With all the goodwill you’ve built up by getting a good introduction to someone on the team you want to join and submitting valuable content to them, you’re extremely likely to get brought in for a full interview.  When you do, your goal is to show you’re as good in person as you are in all the electronic interactions you’ve now had.

When you come to the interview, come ready for everything. Find out everyone you’re interviewing with and research all of them like you already did the company you want to work for. Have something interesting to talk to each person about that shows you did your homework on them. Refresh yourself on all the research you’ve already done and be prepared to talk about and build upon the ideas you submitted in the content you’ve produced.

The great thing about all this effort is that on top of impressing everyone at the company, you should have a very clear idea of what the company is like and be ready to contribute in a big way from day one.

Step 7: What if I don’t get the job?!?

So there is is always the chance that despite all your efforts, you won’t get the job, it’s rare, but it does happen. What’s great is that very often when someone puts in this kind of effort a person hiring will do one of two things:

1) Try to find another job for you so the company can still hire you.

2) Refer you to someone in their network that could hire you.

I have personally experienced scenario 1) twice in my career and have friends who have ended up very happy in roles that came from referrals in scenario 2).

If all else fails, brush your shoulders off and move on to the next job. This much hustle is guaranteed to pay off sooner rather than later.

How would you recommend standing out in the job applicant crowd? Have you found a job and have advice to offer? Tell us in the comments!

Connecting the Dots: How a Boston Connector Landed at an SF Startup

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”Steve Jobs, Stanford Commencement Speech, May 2005

One of the most common questions I’ve heard over the past few weeks from younger members of our community, especially students, is how to build a career in startups. Unlike climbing the corporate ladder, it’s not a straight forward, linear process. As I just made a major move in my career to join KISSmetrics, I’d like to share how I ended up going from Boston startup connector to SF Product Manager.  This will also help answer questions I know some of you have about how I landed this job.

Connecting the Dots – The unorthodox journey of one startuper

To really begin this story, you have to go back to my days at oneforty. When I joined oneforty, I was given the title of Customer Development Manager and asked to help make oneforty a Lean Startup. Since I had only spent a few months working part time with John Prendergast as his cust dev intern, I really had very little experience. Laura Fitton, oneforty’s founder, took a leap of faith I could learn it, but she also was wise enough to know I could not do it alone.  That’s why she set me up to have mentors from day 1.

Immediately upon starting at oneforty, Laura connected me with two Valley Lean experts she got to know while she was out west raising money for oneforty and Pivotal Labs worked to build V1.0 of the site.  These people were internet mentor legends, Dan Martell and Hiten Shah.  Once a month I seemed to find myself on the phone getting what I would happily call an “ass-kicking” from Dan helping me realize all the things I was doing wrong and most importantly, could do to improve my custdev methods.  Roughly every other month I would have a similar discussion with Hiten.

These discussions were priceless in my career development. I would take copious amounts of notes and seriously reflect upon what Hiten and Dan discussed with me each time. I would also share these notes with Laura to make sure I truly understood them and to force myself to teach someone what I learned (a great tool for deepening your understanding).

A Chance Meeting

Fast forward 12 months at oneforty and it is April 2011. I’ve learned a ton about customer development and lean startups, enough that Trevor Owens, founder of Lean Startup Machine (which was just getting off the ground at the time) invited me to be a mentor at the Lean Startup Machine event in New York City. As destiny/fate/karma would have it, Hiten Shah was also one of the mentors for the weekend.

Being a mentor traveling in from another city is very different from mentoring in your home city. When you’re in your city, you likely only stop by for a brief period of time that fits your schedule. But, when you go to another city, you find you spend the vast majority of your time there…which both Hiten and I did in New York City.

After Saturday’s activities wrapped up, all the mentors went out for drinks.  This turned into an audition and test for me.

With Hiten Shah to my right and Patrick Vlaskovits (co-author of the awesome Lean book at custdev.com) grilling me on all sorts of topics from lean startups, to lessons learned at my first real startup job to topics on psychology and body language.  At the time I was dead set on leaving oneforty to start my own company so all Hiten said was, “if you raise money for your idea, come out west and I’ll give you some intros.”  He also encouraged me to quit ASAP to start doing my own thing if that’s what I was passionate about. Coincidentally I did just that on Monday back in Boston.

Out on my own, but on the Radar

After leaving oneforty, I set out to start my company I’ve always dreamed of.  After spinning my tires for 6 months though, I found myself pretty empty handed and a bit discouraged. After a meeting with Sim Simeonov, I refocused my efforts on the lean startups movement.  After a month of interviews and discussions, I published the results, which caught Hiten’s eye when they were tweeted out.

Hiten DM’d me after my first post and we had a call to discuss my findings, which confirmed his suspicious: Lean as a concept is far ahead of actual solid execution of it in the startup world. At the end of the chat, I mentioned that I was planning a trip out to the Valley in early December and asked if we could meet while I was in town.  He agreed.

Meeting in SF and an Offer

When I met with Hiten in December during my Valley trip, we barely talked about KISSmetrics or my potentially working there. The vast majority of our one hour chat was about my strengths and weaknesses and where I was at in my startup career.

Hiten tried to sell me on the idea that coming to the Valley would solve many of my problems, but I presented a series of challenges that I felt prevented it from being the right decision for me.  He countered I could come work for him and it would resolve many of them. I noted the offer, and it did intrigue me, but it mostly sat just sat in the back of my mind.

By the end of the trip, I was much more interested, thinking it may be the next logical step in my career. On the flight back, I emailed Hiten expressing great interest in the role, especially as I discovered I could potentially be filling the shoes of the departed Cindy Alvarez (who just weeks before my visit had left KISSmetrics to join Yammer).

Getting Serious

With the holidays fast approaching, Hiten and I took things slowly, talking about the the potential first in loose terms then in much more specifics. After one phone call where Hiten lifted the proverbial kimono on everything I wanted to ask regarding KISSmetrics as a business, all that was left was an answer to the question, “When can you come meet more of my team for an interview?

With that, I booked tickets to take a quiet trip to SF for the interview in early February.

Sealing the Deal

With an interview scheduled and a focus on landing this job, I employed my proven job acquisition system that requires me to produce, insightful, valuable content for KISSmetrics.  I happened to be reading a psychology book at the time and so I produced a massive document on different ways KISSmetrics could improve their site based on the principles I found in the book.  I also aggregated all my lean learnings in one place so the rest of the team could see the credibility in Lean that Hiten knew I had.

I wasn’t sure what to expect in the interview. All I had were the names of the people I would be talking to and a vague idea that we’d talk about the KISSmetrics product.  Most of the interview turned out to be focused on implementation: how would you do this, what’s wrong with that, what would you do in this circumstance.

Despite not really preparing for such questions, I was able to crush the interview for one simple reason: the last startup idea I had worked on was a Lean Product Management tool.  While the idea didn’t pan out, it led to me talking to 40 people who run product at companies. Through this, I picked up on many best practices and common mistakes. I was armed with more than enough fodder for the interview and believe I’m really armed to take on my first full time product role.

Conclusion – You Never Know…

Whether it’s lessons learned in a failed startup idea’s customer development interviews or an event you’re randomly invited to in another city, you never know what will lead to the next great opportunity in your career.  Startups are all about embracing serendipity. Embrace the machine and you never know where you’ll end up.

Do you have an example of unrelated events that looking back were instrumental in a step or moment in your career?