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.

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.

  • 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.

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 sketcky 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?

Boston, I need your help!

As I prepare to take the giant leap from Boston to San Francisco (in case you missed it read more here), I have a number of things that would be tremendously helpful.  If you can help with any of the following, I’d be most appreciative.

1) Looking for a roommate in SF.

- I’ve heard it’s a nightmare to try to find a place in San Francisco so if you have anyone in your network that lives out there that you could ping and see if they’re looking for a roommate or have a room they need to fill, I’d love to hear from them.

- To give you an idea of what I’m looking for, since KISSmetrics is in SoMA, I’m looking for a place within 20-30 minutes of SoMA via public transportation. Pet free (allergies).

2) Looking to talk to KISSmetrics users

- Does your company use KISSmetrics? Did you try and give up on it? Either way, I’d love to talk to you before I leave March 10th!

- This is your chance to have in person customer development done by the product manager of KISSmetrics. I’ll always be happy to talk to Boston companies, but nothing beats a good in person customer development interview.

3) Looking to Sublet my Somerville Apt

- I have an awesome roommate that loves scotch, pool (I have a table in my apt) and electronics. He’s a great, loyal guy and I need someone to tak over my room in our apartment. It’s near Porter Square. If interested, contact me for details and to come check it out.

4) Anyone I *must* meet in SF?

- A few of you have told me you know some people I need to meet when I get out west. I have a pretty small network out there now so I appreciate any insights on who to meet when I get out there.

5) Advice for Living in SF?

- I know there are a number of you who at one time lived in San Francisco. A number of you have already dropped a lot of knowledge on me for making the most of SF, but if anyone else has advice let me know!

How to get in touch:

Feel free to leave a comment if it’s just some quick SF advice, or to set up a KISSmetrics meeting or connect me to anyone in SF (to meet or talk about roommates), use my gmail: evanish dot j at gmail dot com.

Thanks!

Dear Boston…

Dear Boston,

The past 8 years have been the most invigorating and exciting of my life. You were my first city after escaping the suburbs of central Pennsylvania to attend Northeastern. We were together for the wild rides of the Red Sox playoff runs in 2003, 2004 and 2007 and all the other championships that have made this the city of champions that such a rabid sports town deserves.  Many of my favorite memories with friends involve Boston sports playoff games. You’ve also been a big part of my life’s ups and downs.  Nothing calms my mind better than a walk down Boylston Street on a busy day or a quiet night of reflection by the Christian Science Center reflecting pool.

When I walked onto Northeastern’s campus for the first time, I knew it was where I’d spend the next 5 years. After graduation, I still felt a strong connection as I excitedly got my start at E Ink.  Later, your startup community welcomed me thanks to the amazing DartBoston community and helped shape me into the person I am today: better, faster, smarter, stronger.

All of this is what makes what I’m about to say so hard.

From almost the beginning of my time here, I’ve known I wanted to be an entrepreneur more than anything else in the world; it was a presentation by one of your leaders, Russ Wilcox, when I was a freshman that convinced me of this path. It was later other entrepreneurs that helped me get my start and make me who I am today: from Tim Rowe and Scott Kirsner helping encourage me to start Greenhorn Connect to John Prendergast giving me my first job in the ecosystem as a customer development intern to Laura Fitton being the one person willing to give me a shot at a full time job. Countless others have helped along the way as I’ve needed advice, friendship and a helping hand.

I left oneforty in April 2011 to finally build the great company I’ve always dreamed of.  I wanted to take all the lessons I’ve learned and build the next great anchor company here. Unfortunately, despite trying many different ways to get a company started, nothing has worked.

While I struggled to find the cofounder for my dream company for a multitude of reasons, I was equally failing at finding the right startup idea. Many have told me it’s a spiritual quest; the right idea will grab you and you’ll just “know.”  I know they’re right. That’s how Greenhorn Connect happened, but it doesn’t make the pursuit any easier.

As I continued my quest, I felt I had to start expanding my efforts. That’s why in December, I took a trip to visit your brother out west, San Francisco.  I needed to spend some time away from you to gain perspective and see if the next step could actually be anywhere but here.

I thought I’d never take another job after oneforty. I’m an entrepreneur at heart and felt like my time was now. But after getting perspective out West and having the right person say, “why don’t you come work for me?” I realized I had the perfect opportunity I couldn’t pass up.

There are certain people in the startup world I’ve grown to admire greatly. They’re all on their way to, or already have built great companies. They’re thoughtful leaders with big visions. They understand the pay it forward mentality. And when one of them not only offers you the opportunity to join their team, but in an ideal role, where you get to work directly with them and the company is still at a small enough stage to your liking, you have a too-good-to-pass-on opportunity.

In this perfect storm, the leader is Hiten Shah, the company is KISSmetrics, and my role is Product Manager with the responsibilities to make them a great customer-focused, lean startup with a product their customers love.  I’m both punching above my weight class and bringing all of my skills to the table for this role. I couldn’t be more excited about the opportunities and challenges ahead. At the same time, it hurts greatly to leave Boston to join this San Francisco-based company.

After all the memories, all the great friends inside and out of the startup community and all I’ve built here, I know it’s hard to believe I can pack my bags and leave, but I know this is the next step I must take.  It is far from easy, but a move that makes sense as I work to get closer to my dream of building an achor company.

Your first question is probably, “What happens to Greenhorn Connect?”  Do not worry. Greenhorn Connect is in *great* hands with Paul Hlatky and Pardees Safizadeh.  They are two of the best young people I’ve met in Boston and I’m honored they’ve accepted the ongoing challenge of keeping Greenhorn Connect serving the Boston startup community.  I’ve been working with Paul for months to prepare him to be my successor and I know that he is not only up to the task, but will take Greenhorn Connect to new heights.  He was the driving force behind the Boston Tech Talent Fair and the buses that brought students to #RubyRiot. This is just the beginning of what he can and will do.

While I’ll be handing the reigns to Paul and moving out West, know that Boston and my many friends, mentors and colleagues will not be forgotten. Technology is folding space and time which means that Twitter, Skype and the occasional flight will still keep us connected.  I care so much about our startup community and all the friendships I’ve made along the way, I can’t imagine just forgetting about it.  I’m still planning events in the community like RamenCamp in May and I wouldn’t miss the unConference for anything. I hope to be a bridge between my new home and those here in Boston.

This is the beginning of an exciting and scary new adventure for me and the Greenhorn Connect team. I hope I can count on your support as I set out on my new journey, and more importantly, that you’ll help Paul and Pardees succeed in having Greenhorn Connect continue to support the Boston startup ecosystem.

Thanks,
Jason

West Coast Differences – Non Startup Edition

I just took a trip to the Valley for the first time. I’ve had a lot to say about it from the perspective of an entrepreneur (see on Greenhorn Connect here and at OnStartups here). I also noticed quite a few things that have nothing to do with startups that I found culturally interesting.

1) Everyone is nice

Boston can be a cold place, and no I’m not talking about the weather. In general, you just don’t find people being friendly walking down the street, and you definitely don’t see it on the road.

One event really tipified this for me: I had just made it out of a parking garage before close. Because of this I didn’t have time to set my GPS before hitting the road. There was no where to park so I pulled off blocking a driveway. As I was engrossed in entering my destination address into my Garmin, an SUV started honking at me; they needed in the driveway. I of course complied.

What happened next shocked me. The woman parked her car, got out and walked over to where I had pulled off slightly up the street. When I put down my window, she apologized for honking her horn at me. 

2) Everyone weighs 15 pounds less

It’s hard to believe until you see it. Everyone is just in slightly better shape than I see them in Boston. It’s a visual average I noticed after a few days.

I think the cause of this is pretty simple. Nice weather = more time outdoors = more exercise. What kills us (even a gym rat like me) are these brutal winters. It’s really hard to get enough cardio in under those circumstances which means every winter you’re putting on a little weight. Add that up over a winter or two and you quickly get those 15 pounds.

3) The Valley has safer drivers

I’ll be totally honest: after not driving for 7.5 years, I’m a pretty terrible driver. Luckily, people in the Valley drive slower on the highways (around 65 instead of 80) and well, they aren’t MassHoles. They actually use things like turn signals and let people over when they do signal. It was refreshing and the only reason I got back to Boston in one piece.

4) Parking is a breeze outside SF

There’s easy parking in Mountain View and Palo Alto. Even downtown. And it’s free. I was terrified when I forgot to bring quarters with me on my trip and was pleasantly surprised to find that I didn’t need them.

5) Their public transportation is good, but flawed too

We all have our gripes with the MBTA but it gets you where you need to go….usually. The SF system is the same. Their buses are slightly unreliable, but have some drawbacks: the stops often smell of urine and the back part of every bus is covered in graffiti. Meanwhile, the CalTrain is incredible. Like a well oiled machine, the trains fly through the Valley right on schedule.

The best part of their system is they’ve tied it all together on one master card (their version of the Charlie Card). The Clipper Card, as they call it, was the only thing I needed and was easy to pick up at a station.

6) They have a serious homeless population

I found out while I was there that SF has the largest homeless population in the country and for some ridiculous reason they give each of them $400 a year (as if the year round good weather wasn’t attractive enough for the homeless).  I think this is a likely contributor to the bus stop urine smell.

These are just a few of the random differences I noticed in comparing the cities of Boston and SF and the Valley vs. New England.  Have you been both places? What have you noticed as a difference?