Work. Life. Love. Balance. Stories From Startup Folk

Startup LoveI saw this article posted by a friend on FB by Scott Weiss a VC at Andreessan Horowitz called Success at work, Failure at home

To me pulling back the curtains behind a life, relationship or personality allows us to see the truth: that there is no such thing as the “perfect life” to aspire to. Instead we are all simply working hard on the goal of being the best people, friends and mates we can be. So don’t be so hard on yourself, learn a little, and share a lot.

With that in mind his post inspired me to post this learning from my own life as a serial startup/”entrepreneur guy” in a relationship.


Why You Can’t Optimize for Intimacy

The style of conversation that helps drive interaction, trust, and motivation within a business and its employees doesn’t translate completely with a person you have an intimate, loving, sensual, and sentimental obligation to.

Some things do translate well. For instance, the patience and even keeled temperament required to maintain a level of respect and openness is important to both work and home lives. On the other hand the levels of distance and tone you employ can have a stark difference between the two environments.

As an example, working on an emotional issue with a significant other doesn’t work well with checkins, progress updates, and check lists (which can be cold to a person you sleep next to every night.) While on the other hand focusing deeply on emotions doesn’t work well when communicating clear objectives and goals with peers and employees (that you hopefully don’t sleep next to – ever.) Again, there is some overlap, but the differences are monumental.

For me, being a startup guy in a relationship is a constant lesson in understanding those differences; not focusing on “optimizing” for your relationship but simply nurturing it together.

So in short as the title says: do not optimize for intimacy. And I know if you are a startup person you are thinking right now “I disagree, of course I can if I just…” Stop right there. I know you “can” – but don’t. — I know you think you can – but don’t! The other person may be feeling more focused and diligent (yay!) for now, but probably feeling less connected, heard, loved, or nurtured over all. Even worst they may be feeling like they are at work – and not in a “intimate relationship.” (boo!) :-p



Why You Can’t Just Show Up to Innovation Day

1B5778763-1301229_trophy_hmed_1228p.blocks_desktop_smallI often get the “Hey, how can we innovate as a company?” question with little attention to each individual employee’s drive to innovate in their daily work lives being a major factor in one’s mind. That is the equivalent of asking “Hey, how can I win the super bowl?” without having a team composed of NFL football players.

Innovation is a sport to be practiced not something you can just show up on game day and expect to win. How many NFL football players don’t practice being great football players everyday and expect to win games every weekend?

Like any professional sport: if you don’t innovate in your daily life you won’t innovate anywhere else.  The funny thing is if you tell someone who wants to be the greatest football player in the world to practice everyday and to push themselves to be a better player every time they practice you will get nods of support from just about anyone listening. (After all running the same drill with the same times will keep you playing JV your whole life.) Conversely, if you ask someone within a business that wants to innovate to constantly be thinking and implementing ways to change their best practices, improve their tools set, update their processes, or try new ways to be more efficient at the office you will often get a majority of employees supporting a resistance and responding with rolled eyes followed by something to the effect of “it’s fine just the way it is – and it has been for years. Why change it now?”

How can you expect to innovate a few times a year with a company filled with workers that don’t believe in practicing innovating with the tools they use, the environment they are use to, and the way they interact with one another on a daily basis? How would a superbowl NFL coach react to an athlete that would rather just run his usual drills when asked to try something new? You can’t expect a company of employees resistant to change or improve HOW they work to then all of a sudden change how a company or the world around them works, can you? It all relates – like the seeds in a root of a blossoming flower. (Sorry, probably too dainty an analogy for a football heavy post, huh?)

Furthermore, just like with football it won’t work with one star player or one small group embracing this ideal. Use the best tools, challenge the old ideas, and try out new processes when you get the opportunity. The more the WHOLE company pushes and adopts an ever changing, improving, and growing daily work life the more that company will get a shot at the innovation ring.

Happy Super Bowl Weekend to all those out there wanting to be their best every chance they get!

Life is a plurality

Life – what more can I say that hasn’t already been said. It starts. It ends. It can do so hundreds of times a day for a single person, or only once – as it is realized before one dies.

It begins with a new breath, a new smile, a new love. It can end with a tear, a passing, a sadness – a separation. In all cases, it is a continuous thread of beginnings and ends. It is the realization of a new perspective, one that can re-invigorate us to feel in ways we didn’t think possible. Life can rush through our lungs with a skip of the heart.

Life is so intricately deep and sometimes so shockingly simple; always beautiful. A lesson learned can open up new doorways – or –  it can tie off fears we’ve been holding on to our entire lives for safety. For comfort.

It can be a prison. One we create around ourselves and find convenience in naming it a fortress, an attitude, a conviction. And to be free, or taste freedom, or free oneself. I am free – for now. I see a world I didn’t see before but know it has always been there. Untouched, for better and worst.

I have yet another new life, but far from the last life to be lived. True – it is nothing more than a new story to describe my already present surroundings; it changes nothing, but changes everything so absolutely. No one and no thing has changed but me. My mind. My eyes. But I am still myself – that I am sure of.

Growth is the escape, the new beginning. Not to destroy the singular life that came before it but to continue the thread of lives born within it.

So what has changed? The prison in which I kept myself? Or more importantly what starts a change, a new beginning, a new life? The catalyst lies in the recognition that prisons do not need to be powerful, ugly, large or made of steel, but they can be gentle, subtle, comforting and safe. They can coddle us in answers to questions we’re searching for but may have never needed to. Those prisons are the hardest to escape.

To escape yourself and what makes you comfortable without losing “yourself” in the process, that is the question. Can you allow a life to end so that a new one can begin without a fear of the end or anxiousness for the beginning? That is the moat and bars that prevent escape.

But it is possible. It is progress. It is life, and life is a plurality.

OpenCO 2013 – Why we love SF, how we work, and our world of content in 2023

OpenCo is the city’s answer to the question: “What makes San Francisco – San Francisco?” Instead of trying to explain the nuances to the culture here the founders of OpenCo decided the best way to describe it is by opening the doors to as many offices as possible within and allow people to come in and see for themselves. At OpenCo attendees sign up for a free pass to any of the over 100 SF offices, from theater troops, to restaurants, to tech startups and more. During the event attendees tour around the city walking into offices to check out their space and take part in an interactive presentation about what that company is doing to try to make an impact on the world. It’s not a lecture, nor a sales pitch, nor is it focused on recruiting, but instead it is a presentation that takes a look into what a company is thinking and how they work. Now expanding into NY, London, and Detroit, the OpenCo movement will be an exciting one for those interested in peeking into to the companies that make a city tick.

This year ShareThis was proud to be invited to host the second annual OpenCo event and we were excited to open their doors to their San Francisco office. There Sean Shadmand talked about the difficulties companies in the industry of social/tech are faced with and how they plan on innovating in the years to come. Check out a video of the presentation and slide decks below.

Video on Vimeo

Slides recorded by Penxy

What a company manifesto means to me and what I would expect it to accomplish

A Manifesto reveals the strengths and values within a company, and does so in a way that decreases the number of complex decision making hurdles for its employees in the day-to-day.

The manifesto will be “the bible” (though only a page) of reasons that lead a team without a need for individual leaders to be present, and can help create the next generation of leaders to form in the same vein.

It relieves people from the stresses and distractions inherent to complex (or seemingly complex) decisions, in the middle of the workday, while fighting in the trenches.Screen Shot 2013-05-14 at 12.22.05 PM

Picture this: A team of army rangers are falling back in the middle of an amazonian battlefield. They realize one of their platoon members went missing while under fire. What do they do? Unorganized soldiers may scatter under this pressure and lose their head. Should the next step be “Every man for themselves!”, or “Let’s hide it out until morning”? Luckily this group of rangers knows that there is one core value that prevails in situations like this: “never leave a soldier behind”. – Boom, decision made. They spend their time devising a plan to find him first and foremost  (no matter the hurdles – it will be resolved).

Values help form a strategy. Most importantly, when things go wrong, values help keep the bigger picture moving tactically. Especially when “fires” make decision making  difficult. Plans fail, but values do not.


More practically speaking, the battles on a tech company’s floor may be less tragic, but are battles nonetheless. Imagine there is a team developing a widget. It is done so with poor (if any) design, but  is backend-ready and functional. A discussion may come up around the pros and cons of deploying something that doesn’t look good but is ready to ship for testing. The debate could rage on, but, with a core manifesto that decision is already made: if the core value says design is key to our tests – then the decision is made to implement a design before deploying. If the core value says release when ready and iterate – again the decision is already made.


Those decisions shape a company and should not change week-to-week, problem-to-problem, or day-by-day from department to department. They shape outcomes and the character of a company through a decision tree that is easy to repeat. Consistent and efficient decision-making is more important than re-assessing the perfect decision for the situation each and every time it comes up. The written word is amazing at facilitating that.


Of course, we all have great thoughts and your company has awesome values already, but having them written down is the difference between an interesting legend shared by some and a religion followed by many.

Documentation, although necessary, does not substitute for a short list of values. Documentation is rarely re-read, and often forgotten; we remember “Go when green” not “Statute 32 Section 5: All those that use public road shall obey stop lights based on the following color …..”

Finally, it is extremely important that your list of values are glossed over. One lazy move away from following your values can easily turn into a utter mess over the years. That does not mean you can’t change your values. If a situation comes up, and your values does not represent how you want to act two things MUST happen: 1) You re-examine your values and change them accordingly or 2) You adjust the situation to fit your values. Period.

As for my suggestions regarding the setting for how a document can be built  as a team here are some thoughts.


  1. Make sure people feel heard (i.e. right down every idea)
  2. Help filter outlaws that promote restrictions (which end up being things people feel reprimanded for doing)  and turn them into the concept that create direction and productivity to help people grow, expand, and focus. It is a document of supportiveness.
  3. Use it to help give people clarity in situations that need tie breakers, or rules of thumb. For example, “future value does not trump current value” has saved our team from missing out on what we have while over planning for something we do not.
  4. Be clear on what an item suggested means when it is written (often times one person’s perspective on what “awareness” can be, for instance, is different than another’s) Be descriptive.
  5. Find a/the person that matches the essence of what a manifesto item describes. They will most likely be the champion of that thought and help keep it alive and well. Find the passion in the people and you will also find the strength in the doc.

I believe once the fundamental concepts are solidified into the manifesto it becomes a spine for current, and as importantly, new employees that come in so they can quickly latch onto and adopt the companies process/thinking as it expands in size.
There will be the debate over the items presented, and debate is good. As such, it may also be a good idea to nail down some keywords that keep the conversation on track to what we believe the manifesto points should adhere to.

The words I propose are:

  • positive
  • smooth
  • friendly
  • helpful
  • productive

If an item does not instill many of these words, for instance, then the item may be off track.

Efficiently Inefficient: Processes that can improve quality and quantity of life

For our latest project at Socialize Isaac and I are going to increase the release cycle even further and go from a few releases per group per week, to a few releases per day. I find moving more efficiently and quickly over the years always takes a few non-intuitive jarring mental steps. (If they didn’t we would have been way more efficient as a society way earlier on in history).

Here are a couple things that always seem to be the foundation of inching your way up the efficiency hill.

1) Get to a point at which you truly trust your results, not just feel good or secure about them, but quantitative based results that have a quantitative “I trust this” number. This is what I call the “don’t look over your shoulder moment”, because if you’re looking over your shoulder to make sure nothing has gone wrong, you are not looking forward to make sure new things go right. This accomplished with unit/itests tests, or in our everyday lives marking your calendar or adding a reminder. Even at managing people in the office, time and time again setting up employees to be trusted and autonomous, with a simple audit system to make you aware only if something is wrong, has proven time and time again to produce happier, more creative, more productive employees in a company that can scale. Basically every one wins big when you make sure you create process that handles things that are set to let you know if you need to take action, and quite %100 otherwise.

2) Really reconsider what you’re are willing to bare in mistakes. This is usually a major brain switch moment. Sometimes people can work 100x more efficiently and productively if they just allow themselves to be wrong for a totally fixable 1 minute per year. Yes your server may go down once a year, but instead of working hard to make sure that never happens (which is impossible), work hard to make sure systems are in place to recover super quickly. The funny thing is when you accomplish #1 above, mixed with this #2 item, you start performing better than you could have imagined.

3) Remove process that is there to support the more intuitive faux “warm and fuzzy” feelings that keep 1 and 2 from happening.

4) Always push yourself, and those around you, to test process that offer efficiency gains even if you don’t feel comfortable at first. Comfort is often the foundation of slowness, and trying new things even against your “better judgement” are the only ways to break free.


For you nerds out there, here is the article from github Isaac passed on to me that sparked our latest evolution in product releases. Although this post and its sentiment are, in my book, universal throughout life and business and not code.

There is no better quote to reference then your own, made from the source:Not the facts, just the data

Here is another post in my series of “Not the facts, just the data”. This post came after an argument I had with someone I care about. Make no mistake that this is not a rebutle but just a perspective on data vs. facts, and arguments vs. politics.

The biggest argument I stand being, from my point of view, is this: Do not trust or love politics, love your people, peers, country, and family.

Politicians on either side of the coin will use data for their agenda. If you get wrapped up in it, and start believing what you are *told*, through sound bites and ads, you will be misinformed 100% of the time. More information isn’t tantamount to a depth of information.

This is why I have learned not to trust politics, they bet on people not reading the full story (as wel only have so much time in the day) and try to create anger and conflict to make people mad enough to vote how they want. It feels like THAT is what has gotten worst over the years, not so much what is happening in the world, just the way its agenda is given to us. China does it by cutting off information, the US does it by overloading its people with one sided information.
The good news is that with the advent of the Internet it is now so easy to get the data and documents from the source, and fight back as a citizen saying “don’t use me for your agenda”. No need to go to the library and send letters requesting data that may take days or weeks; it is available now if you are willing to read it.
As my methods to get to the data evolve, I try and follow some procedures to navigate past the political propaganda.
First, If I find a “fact” that I am researching on any news site, I look for the citation for the “fact” so I know where it came from, and then look that fact up from it source to read it myself. If there is not citation, I start over. A citation does not make it data, it just helps you get a path to the source. Secondly, if I find the source I read it, if I cannot find the source I look for the source directly. At this stage in the evolution of my process I have deemed .gov sites and non-profit census bureaus as a final source. In some situation you can never be sure unless you count the numbers yourself, but I have found the most consistency at that level. Yes I know that even the government stats, non profits, and census bureaus can lie but if I can find some consitancy at that level I am pleased.
Lastly, how to spot a fact with skeletons in its closet that should trigger an investigation like the one above before having the debate.
Well, the main thing that triggers a fact check to me are statistics, and references to bill being voted on. Why? Well, over the years I have found that stats have a high potential to be screwed. Or example, what constitutes “1 year” – Fiscal year or calendar year etc. Another example is is the stats extrapolated from previous data or data that has already happened. Another read flag is the use of tag lines,  sound bits and general words like “taxes”, and “everyone”, and “higher” — higher then when and what for whom? Also, the reference to bills, are tough to believe from something like “he voted to….” After living in DC and working on capitol hill with you realize that both sides of the fence will quote the same document at different parts and come up with completely different conclusion. It is impossible for both are either to be entirely right, but both sides would never realize that they both *think* they are 100% right. As my readers and friends know by now, one of my big rules of thumb is: If experts disagree it is time to make your own decisions. A bill is written by many people with many agendas for their state. They are stiuffed, written and re-written over and over to try to get as much as they each want to get in it, and keep out as much as they don’t. They do this hours and hours everyday to come to a final document that is then voted on by all parties. It is very important to remember that time line, for no document has one message, and if it passed their is a big chance that both parties voted yes on it (unless there was a big split with few deciding votes). Point being, much could have gone into a document and so much more history to that document then any sound bite could articulate.
So, one of the bills that was brought as a point of contention was based on a sound bites saying “Obama voted on late term abortion”, and it was said that the bill was made to let mothers have the right to kill a baby after it is born alive. Well, personal, I did not know about that bill first hand, and that I promised to look it up. Speaking from my own perspectives I don’t like the sound of it, but I want the source and document first before my personal conclusions on that vote are spoken.
This is one of the actual bills voted on for Illinois referenced. It only took a few minutes to bring up. It was indeed named “Partial-birth Abortion Ban Act”, so that is a true data point.  As it turns out was voted on 44-7 (almost everyone agreed in both parties, that decided to attend). Also there were 5 present votes. What does a present vote mean?
 The “present” vote is in effect a “no” vote, but it is a “no” vote that sends a message. The “present” vote is used by lawmakers in situations where they agree with a bill in
spirit, however the current version of the bill is not good enough to vote “yes;”
The bill, in my first hand summary, would be this:  A bill for late term abortion *if* it will kill the mother to have the baby, but still says it is illegal otherwise. But please, do not take my word for it! Read it here:
So it is important for me to see just how complex a bill can be, in addition to how complex it is to create, finalize,vote on and pass, on it.
Another topic was immigration. Stats are the hardest data to really find concrete numbers. There isn’t a list of people that are counted ever. It is def not as easy to get to the bottom of as a document being references. Old census bureus that have been around and referenced over time by both parties is, to me, a better place to start than from a news site, network, or politician.
So here is census data from the Pew Foundation on immigration stats, highest in 2007, and leveled off down by a million the following years.
It is important to note that data usually doesn’t come with a “should”, “good”, “bad”, or “won’t” list of words around it. Why did it go up? That is as complex as why did it go down? And as you will see that once why is added to statistics rarely does a group of experts agree. There are so many variables, and that is where debates and politics I suppose have a place. But I would implore you all out there to start the debate after the data is presented, and be sure not to find yourself repeating an ad or politicians claim that a statistic is “up” or “down” until you read it for yourself from the source.
I think my new strategy will be to make sure that before I argue on big issues like this, especially in DC where the ads and politics are so ripe with contention, I will just say show me the document we are arguing over before getting involved. If we do, maybe the citizens of this country can take back their right to be informed, and to make decisions without political agenda being the force that drives them.