Why I Hack on Hack Day

At Visible Measures, every quarter, our amazing engineering team organizes “Hack Day”, a 24 hour hackathon during which our folks work on ideas, cutting edge research, and experiments.  After usually working late into the night and early the next morning, there are demonstrations of all the Hacks for the entire company to see and then vote on.  I encourage people across the organization to participate as it’s great fun.  The winner of each Hack Day gets to hold the proverbial “pimp chalice” (see image below) until the next Hack Day.  

I also try to do a Hack for each Hack Day, even though my coding skills are as stale as a 10 year old bagel. Why do I bother?

I hack on Hack Day because:

  1. I want to show support and solidarity with the most dedicated, passionate, innovative, and selfless engineering team I have ever known
  2. it reminds me of how brilliant our guys really are. The sheer scale and diversity of what they deal with is unreal. My little baby attempt at a Hack Day app is just no comparison, but my struggles with building it keep our guys’ skills in perspective for me
  3. I think that CEOs of companies should have some idea how the sausage is made and I think that is why many early stage tech founders should be able to code. Even if their code, er my code, is the software equivalent of a “learn your ABC’s” book

The bigger question here is, if you are an entrepreneur, shouldn’t you know how the various parts of your business work, at least at a high level?  OK, gotta get back to it. My app still doesn’t work right.


Make It Great

A friend was recounting to me a story of a huge project he had to do for his very famous billionaire boss.  I am leaving out names to protect the well-known innocent.

My friend had a whole team of people working on this project, and given its relatively open scope, the team was a little unsure of just how broad and deep a view to take on the work.

After 2 weeks of very hard work, my friend requested a check-in with his boss, the billionaire who had requested the project in the first place.  My friend’s thinking was to be able to get some feedback from his boss to see if his team was on the right track. But ultimately, my friend was looking for some sort guidance in the way of “limiting parameters” for this project. He was trying to contain scope.

At the check-in meeting, my friend gives a brief update and then asks for some feedback from his billionaire boss. His boss looks at him for a moment. He pauses.

Then he says, “Make it great.” 

That’s it. That’s all he said. My friend was caught aback, but after thinking about it, he laughed. He had been selfishly looking for a way to minimize the work that he and his team would have to do, but instead, he was given a mandate to do an incredible job.

His team ended up over-preparing probably by a factor of 3, but in the end, the work was GREAT. And he learned a lesson that he said he would never forget.  When he told me this story, I was wow’d by it. What a great answer. 

Really, isn’t that the answer to any question of how to approach a project or anything that you are spending time on?  Make it great.


The Worst Reason to be an Entrepreneur

Years ago, a former colleague told me that he wanted to start a company so that he wouldn’t have a boss anymore.  His comment immediately gave me pause, but only now after years of building Visible Measures do I understand why his statement was so wrong.

To be an entrepreneur, you have to have optimism, conviction, and passion.  Why?  Because there will often be downs (and ups) that you will have to find a way to get over or push through.  To be an enterpreneur, you should be driven to make a dent in the universe, solve a problem, build something from nothing.  Not having a boss?  That has to be the worst reason to be an enterpreneur. Not only because it hints at having a bad attitude, but because it is patently false.

When you are an entrepreneur, you are starting a company.  There are very few instances where you can start a company without partners, backers, investors, colleagues, or clients.  If you have any of these, they effectively are your “boss”.  Your clients want you to do something?  You should at least listen to them.  Your investors think that you should go in a certain direction?  Hopefully, you are not just giving them the 1 finger salute.  

Practicing “subservient leadership” may not be for everyone, but in truth, most venture-backed startup founders / CEOs have many “bosses”.  I personally believe that I exist to serve the needs of my teammates, investors, clients, etc.  It can be a very lonely role, and you often have to make decisions that are painful in order to maximize results for as many as possible.  I may have the title of CEO, but that just means that when things go wrong, the buck stops with me, and when things go well, the team should get the credit 🙂

Oh and did I mention that a board of directors can essentially replace a CEO at any time?  That is one of the key responsibilities of a board.  So you are thinking of starting a company to not have a boss?  You should think again.

What entrepreneurs can learn from Peyton Manning


Peyton Manning’s career with the Colts ended today – and though I’ve never been a fan of the Colts, I always admired Manning’s professionalism and positive attitude.

As an example, when Manning was a rookie, a reporter asked him what he was going to do with all the money he was just awarded in his contract, to which Manning said, “Earn it”.  <– bad ass

As for his perspective on playing football: Manning said that he tried to remember that we are not promised tomorrow, that it can all be taken away at any time.  He said that he tried never to take anything for granted and to appreciate each day.

To me, this situation with Manning offers a lot for entrepreneurs to learn from:

1) How to handle yourself in a tough situation with grace and class (see Peyton Manning’s goodbye speech where he thanks Colts owner Jim Irsay despite all the awkwardness of the final months of his Colts career)

2) How to appreciate all the positive in a situation: recognize the incredible opportunities you’ve had to follow your dreams, even if things don’t necessarily all work exactly as you had planned

3) Recognize that you are not guaranteed anything as a startup founder, early employee, or CEO.  You have to earn it every day, and guard your integrity and reputation fiercely even after you are gone. Manning didn’t want to burn any bridges on the way out. He went out with his head held up high and he thanked everyone in such a gracious fashion

4) Appreciate and celebrate past accomplishments, but realize that the reality of the business world is that the models of the future do not necessariy fit in the containers of the past (via @rishad)

Reaction to Manning getting released was swift and wide ranging: One comment that I found interesting was from the Detroit Lions’ Chris Harris on Twitter: “Peyton’s release puts things in perspective…….if Peyton can get released, WE ALL CAN GET RELEASED!!!!!” 

I try to constantly remind myself that I as CEO can be fired at any time by a company’s board. Anyone can be fired – that’s what we sign up for.  I try to keep this in mind because really, it’s about not letting yourself get complacent about your place in the world.  If we are not moving forward, then we’re not really moving. Manning is moving on – I wish him well as he moves forward.

Making the Turn – Leveraging a Pivot into Growth

I read a post today from Bijan (Spark Capital) that talks about how the progression of a startup is “hardly ever goes straight up and to the right”.  There are also statistics out there that the business models of approximately 80% of very successful startup companies have had some sort of pivot in their lifecycle. 

Couldn’t agree more. Why a pivot? And how can companies leverage a pivot in their model to accelerate growth?  


Why so many pivots?

Startups exist to solve problems in a new way. The “new” part of this means that more often than not, you are trying something that hasn’t been done before, with the goal of building something from nothing. You are often attempting to solve a problem that either is a new one (eg. a changing media landscape creates new challenges) or one that can be address in an innovative manner because of a changing environment (eg. new technol

ogies enable advances where they were not possible before – such as broadband internet penetration and or smartphone adoption enables an array of new solutions to existing problems).

Because of the “newness” of creating a startup, there are many questions for which you will not have answers. You have to be able to make assumptions based on as much data, advice, and instinct as you can muster from your team, advisors, investors etc. And you do your best to execute like hell from there.

But along the way, as you are in the guts of building your solution to the problem that you are trying to solve, you learn a TON about the market in which you are now deeply and personally involved in.  Even if you have prior experience in that market, you will learn more and from a different perspective than you have had before.  You may recognize new opportunities or issues with assumptions that you had going into your venture.

An example: Fab.com

One example of a company that went through a pivot is Fab.com. Fab started out as Fabulis, a social network built on top of Facebook geared toward the homosexual community.  Founder Jason Goldberg is a serial entrepreneur and a very product-oriented person.  He led the company to build, iterate, and innovate quickly.  But at some point along the way, he and his team recognized an opportunity to build something different that might address an even larger market opportunity: a design-oriented commerce company.

Once Jason and his team made the strategic decision to pivot, they worked like mad to build an entirely new property quickly.  They relaunched as Fab.com – and grew extremely quickly.  They recently raised a large round of funding at a high valuation, a testament to the traction they are building.

Key need: Self-awareness

One of the biggest lessons to take from the Fab story is that they had the guts and self-awareness to identify issues, recognize a larger opportunity, and deploy resources aggressively to pursue the new opportunity. Having the self-awareness to make change is, in my opinion, the most difficult part of this process. Not everyone and not every company is self-aware enough to recognize ones strengths AND weakness, successes AND failings.  When you are in the trenches, it is extremely hard to be able to pull your head up long enough to look around and see what is really happening out there.  You can get so internally focused that you can often miss what the market is telling you.  The fact that some 9 out of 10 startups fail to achieve success is an indicator of a lack of self-awareness sometimes in startups.

Guidepost: Core Values

One thing that can help guide a company through a pivot is your set of Core Values. A company is often founded on a core belief or core philosophy. A belief that something is really needed, that a certain trend will emerge and prevail. In Fab’s case, a focus on design and on creating a great consumer product experience applied both pre-pivot and post-pivot. Despite the upheaval of a changing your model or business, core values can hopefully act as a guidepost through to the other side.

Leveraging a Pivot

So let’s say you are a startup, you’ve built something, you’ve identified a larger opportunity, and now you are pivoting. How can you leverage a pivot and turn it into accelerated growth?


First, you hopefully used market feedback and data to tell you that there was “gold in them thar hills” when you identified the potential pivot. As an example, in the case of Justin.tv, they found that one of the most popular categories of live web cam video content being broadcasted and consumed by their community was video gameplay content.  They decided to leverage this finding to create an entirely new property called Twitch.TV – a gaming discovery and gameplay community. 

Why create a whole new site? In order to fully go after the new opportunity (eg. gameplay) Justin and the rest of the Justin.tv folks recognized that they had to build a new browsing, viewing, and community building experience focused on the audience that was going to be using it.  Rather than having more general purpose video recording, playing, and browing features, Twitch.TV is squarely focused on gamers and their needs. This level of focus also makes it easier to feature advertisers who want to reach this audience.

Making the Turn

Something that isn’t often discussed in terms of companies making a pivot is that it is often a gut-wrenching, soul-searching, painful experience in which many people inside the company can lose faith.  Some people are just not able to “make the turn” either mentally or in terms of the skills that may be needed for the new direction of the company versus the older direction. People resist change. People may feel burned out and exhausted, or they may feel disgruntled and disenfranchised. These are natural feelings. As they say, feelings are not right or wrong, they just are. 

But how someone responds to these feelings can be positive or negative. If a person bucks up and decides that they have the energy, drive, and passion to push forward (hopefully with as clear a mental slate as possible) then people can make the turn.

A company though, in order to survive if it has gone down this path, has little choice other than to Make the Turn, fizzle out, or plateau. In my opinion, in the life of a truly entrepreneurial technology startup, to grow is to survive. To plateau is to fizzle.  At Visible Measures, we made a pivot at the end of 2010, and it was a seriously long and arduous process to get to the other side (and by the way, we are still at the beginning of what we hope is a massively long journey). But we closed 2011 with almost 500% revenue growth over 2010 and about 3X the staff.  It has been amazing to see how the company now is so aligned around our new strategy. 

Making the Turn is hard, and few companies can pull it off. History is littered with the names of companies who could not do it.  Why is it so difficult?  Making the Turn requires a company to 1) rally as much of itself and its team together toward the new direction as it can 2) inject new talent, blood, energy, and skills where needed, and 3) go for it with total conviction.  Failing at any of these steps most likely means trouble.

Yes, it is extermely difficult to leverage a pivot into growth, but that is what Making the Turn is all about.



Your co-founder: Your family


In this blog post, Fred Wilson is dead-on about your family being the co-founder of an entrepreneur’s business.

Startup life can be brutal.  The people busting their butts to create something from nothing sacrifice a lot.  But the families of the people at a startup also suffer and sacrifice.

An entrepreneur’s spouse (or significant other) being understanding, supportive, and often times directly helpful to said entrepreneur can often be the difference in a startup’s success and (perhaps more importantly) a family’s happiness.

Valentine’s day = startup co-founder (Spouse+family) appreciation day 



Invention = Disruption – Jeff Bezos of Amazon on Amazon’s Culture of Invention


Jeff Bezos will go down as one of the top entrepreneurs of all time.  In this great article in Wired, Jeff Bezos talks about how Amazon views the Kindle as a gateway to the media services of Amazon, rather than as piece of hardware.  In discussing how the Kindle came to pass and how Amazon is not afraid to disrupt industries (eg. the publishing industry) where it may be strong, Bezos says:

“As a company, one of our greatest cultural strengths is accepting the fact that if you’re going to invent, you’re going to disrupt. A lot of entrenched interests are not going to like it. Some of them will be genuinely concerned about the new way, and some of them will have a vested self-interest in preserving the old way. But in both cases, they’re going to create a lot of noise, and it’s very easy for employees to be distracted by that. It could be criticism of something that we actually believe in. It could also be too much praise about something that we’re not doing as well as the outside world says we’re doing it. We’re going to stay heads-down and work on the business.”

At startups, you are constantly having to reinvent yourself as you grow…even if your business doesn’t change much, if you are successful, your company will expand rapidly and the type of company you are has to evolve with it.  To see such a large company rapidly innovate and create entirely new categories of services (eg. Amazon Web Services) is very inspiring.