Career/Role Fit – a key aspect of being a great leader

This post won’t be very long as I feel strange even commenting on what great leadership looks like, but from my past experience, some of the best bosses I’ve had understand the idea of career/role fit.

For decades, leaders inside an organization would hire people exclusively based on their ability to perform a routine task over and over. People would take their place as a replaceable cog along an assembly line, complete the task over and over, and then leave at the end of the day. If the employee didn’t perform the task well enough, they would be fired and replaced with someone who could complete it in a more efficient manner.

It worked well at the time. But times have changed.

Knowledge work

As more and more work has shifted towards using your brain vs. using your hands, I’ve seen and experienced how leaders still base decisions solely on if an employee has the ability to perform the task or not. There’s very little thought put into asking “does this person actually want to do this? Is it meaningful to them?” As a leader, it’s your job to figure out what motivates each of your employees. If you don’t know it, how can you put them in a role that they pursue with passion and energy?

p.s. – I’m building something to help with this.

From my observations, the best leaders understand that when you assign roles and responsibilities based on the ability to perform a task (without considering motivations), you’re going to take a hit on productivity and happiness. Even for organizations who don’t care that much about employee ‘happiness’ – don’t you want each person to be hitting full productivity?

In competitive hiring markets, the industrial-age approach is a recipe for disaster, as people will leave to find a role that aligns better with their aspirations and motivations.

Long story short, if you’re a leader, take some time to learn what each employee is capable of, but also who they aspire to be at work (and in their career). If you don’t, it’s like running one of your machines at 50% efficiency.

What motivates me

I took this great assessment a while back, and here are the top two things that motivate me. Hopefully this helps paint a picture around motivations/career aspirations.



Read More

My Outlook on Investing

I’ve had this conversation a few times in the past month, so I figured I’d write a quick post on my thoughts on investing. I’m using the term investing loosely, but I’m specifically referring to exerting energy or financial resources with the hope of achieving some type of positive return later in life. This post will mostly be a brain-dump of thoughts.

Number #1 Rule

Invest in yourself. Any investment I make is primarily a result of my desire to learn something. There must be a learning objective. Here’s a few examples to illustrate:

  1. Buying a condo – learn how real estate investing works. Learn how to renovate and/or fix things. Test theories around what areas may appreciate in value.
  2. Lending Club – Learn how peer to peer lending works.
  3. Stocks   Learn how to value a company. Test theories around growth industries/companies.
    1. A few stocks I’ve picked (TSLA, FB, BOX, TEAM)

Number #2 Rule

The further you abstract yourself away from making decisions about your investments, the less you learn, and the more risky it is. I get that a financial advisor is smarter than I am regarding finances, however, what happens if they lose a ton of your hard-earned money? You blame them.

Would you rather lose $5,000 as a result of your own decision, or someone else’s? If I lose it, I can only blame myself, and I learn from my mistakes. If someone else loses my money, I learn very little.

Here’s another example. Let’s say I have $50k to invest. I could either invest it in the stock/bond market, or I could buy a piece of real estate. If I invest in the market, I’m constrained to a few major decisions 1.) what firm invests the money 2.) what’s the portfolio composition?

Now compare that to real estate. I can 1.) choose the location to invest 2.) pick the building to invest in 3.) choose where I get a mortgage, 4) choose how much to invest in improvements, etc. With each decision there’s an opportunity to learn. If you abstract yourself away from most of the decisions, you save time, but learn very little. 

Side note: it seems crazy to me that a “good” investment strategy revolves around handing someone else your money, and regardless of how well they perform, they still make the same amount (referring to management fees).

No Brainer Investing

If I see a book and I think it looks remotely interesting, I buy it. If I spend $10 for a book and learn one thing, it pays itself off. Books are compressed knowledge/life experiences. Why learn from my own mistakes when I can learn from someone else’s?


I’m plan on working until the day I die. I highly doubt social security will exist in forty years (as it’s on the road to insolvency in the next ten years or so). I see work as a way to exercise my brain. Therefore, I do not plan on saving for retirement in a traditional sense.

When I say traditional, I mean maxing out 401ks, etc. Essentially stashing a percentage of your earnings away for decades, with the goal of no longer working, and supporting yourself off the savings accumulated.



Read More

Why I moved away from a booming tech ecosystem (Boston) to Portland, ME

In early September, after a few years living/working in Boston, my wife and I made the decision to move to Portland, Maine. For us, we both grew up in Maine, so it was a chance to get back to the “motherland.” For the most part, we enjoyed our time down in Boston, found great opportunities, and met awesome people. But it was time to go home.

I’ve found myself explaining my decision to numerous people, so I decided it was probably worth a blog post with a further explanation.

Keeping the Job

The biggest detractor for moving to another location is almost always the career-choices that need to be made to accommodate the situation. Especially moving away from a city like Boston, you tend to make career sacrifices. Not this time.

Enter working from home. As someone who grew up homeschooled, I was bred to do things from home, so it’s not a huge shock. Ali continues to work for, and I work for Crystal. Nothing changed.

Most jobs I’ve worked have the option to work remotely. I expect this trend to continue, especially if you’re known to produce quality work. My decision to move to Portland is also a bet that my career can continue to progress outside a tech epicenter. We’ll see what happens.

There’s a certain level of excitement when you live in a tech epicenter like Boston. It’s great because you’re around people who continue to strive to create value. It’s an up-leveling process.

Avoiding the nonsense

On the other hand, the level of utter nonsense in the tech community is astounding. The hype train is in full cycle, and instead of being heads-down building something valuable, many people in tech are more concerned about how they (or their startup) looks.

This environment rewards wasteful activities. It’s like a big house of cards waiting to fall.

Very few people in tech have seen success, but everyone wants to pretend like they are one of the chosen few. It doesn’t matter if your company was bought in a fire-sale, all the matters is that you were “acquired”. I want no part of this.

Portland has been humbling. Lawyers/Doctors are the upper echelon of the community, and no one has heard of Crystal. Many people don’t try the latest technology or check Product Hunt everyday. They use tech if it’s valuable. They aren’t constantly testing apps for fun.

If someone saw me working at a coffee shop, they may think I was homeless (probably my fault). I’m definitely not working in their eyes. I love that for some reason. If they expect the worst, you can only impress them.

This environment brings a lot of clarity. How do I explain Crystal to a normal person? Are they interested in what we’re building? Is it something they would use in the future?

It’s very easy to see what technology is valuable to the mass market up here. Case and point: An 80-year-old lady at the condo association meeting called Nextdoor, “a local blog”.

I find Portland to be a counterbalance to what most of people in tech spend most of their time thinking about. This diversity of thought has been refreshing.

Quality of Life

Portland is pretty cool

I’ve grown to really like Portland. It’s a cool city, known for a ton of restaurants & epic beer. There’s no shortage of things to do, and I can get out in the middle of nowhere in 15 minutes and hike/canoe/etc. It’s the best of both worlds (city/country), and I’m not missing anything.

There’s plenty of coffee shops to work from, so that’s always good. And this is a couple miles away.



My mortgage on a 2 bedroom condo on the ocean is $200/mo cheaper than what I was paying for a 1 bedroom in Somerville. If I wanted to purchase a similar condo in Somerville, it would have been 3x the price. This monthly savings (amongst other things) allows us to pursue other opportunities.

Nascent Tech Community

Maine has never been a leader in tech. Lobsters, yes. Big tech companies? Not really.

With that being said, there’s some activity up here. Enough to give me hope that things will change in the future. So I want to help it grow. As someone who grew up here, if I can’t come home, what makes me think that someone else will move here?

I remember what it was like to be a 16 year-old kid desperately trying to learn web design, and meet other people who could help. It was tough to find people. I was constantly shut down when working on projects in high school. I don’t want that to happen to other young people here trying to build stuff. I want to help.

Easy Access

Just because I moved doesn’t mean I won’t go to Boston and meet up with friends. Within 2 hours, I can take a bus/train and be downtown with ease.

Crystal is based in Nashville, so I’ll fly down about 1x/quarter. The flight might be an extra 30 minutes compared to Boston.


Ali and I spent a ton of time driving back and forth from Boston <-> Portland (where her family lives) and Bangor (where my parents live). In short, every few weeks, we’d dedicate insane amounts of time on the road. We’d do it again if we had to, but we are now 15 minutes from Ali’s family, and 2 hours from my parents. Plus they can visit us too :)


The biggest downside to living here has been the lack of youth. Portland is probably the youngest city in Maine, but Maine is an old-people state.  I’m fine with that, but I’d certainly like to quickly grab coffee with another younger person. Hopefully this changes with time.

Read More

The impending downfall of Maine newspapers

(Above photo: one of the funniest news blunders of all time)

I grew up with my face buried in a newspaper. I would visit my grandparent’s house and read the paper with my grandfather (yes, the comics mostly, but that still counts right?) For some bizarre reason, I have a fascination with the newspaper industry, and in particular, the disruption happening right now.

Being a Maine resident for most of my life, I’m watching the Maine newspaper scene with interest. I’ve convinced myself that there’s going to be some MAJOR shakeups happening soon, and I figured I’d explain why.

I should preface this by saying that I am not a fan of any Maine newspaper at the by all means take what I’m going to say with a grain of salt. To be honest, the reason why I’m writing this is to put my theories to the’s almost like fantasy football, but for business.

Maine newspapers haven’t been hit hard yet

This sounds insane, but Maine hasn’t received the brunt of the newspaper decline yet. My reasoning is simple:

Maine has the oldest population in the country, and it’s the older demographic that still generally still purchases the newspaper on a consistent basis. This has given Maine newspapers a little bit more time to prepare for the impact. Unfortunately, it doesn’t look like they’ve taken advantage of that (the Press Herald is starting to wake up.)

Side note: my 70+ year-old grandfather just cancelled his BDN subscription after 30 years..his reasoning? “The paper is too thin, and all they do is talk about how bad Governor LePage is.”

Too much headcount

Put simply, Maine newspapers are too bloated. There’s too much headcount. A quick survey of LinkedIn shows the the Press Herald has 150 employees and the Bangor Daily News has 155. That’s simply unsustainable, especially when you’re losing 10-15% of readership in a single year. I would assume the BDN drop has to do with their genius idea to request information about gun owners.

Business Model Experimentation

The Press Herald recently implemented metered usage, offering 10 articles/month to people who don’t know how to use an incognito window and bypass it. They also have been pushing long-form content, which is a step in the right direction.

On the other hand, the Bangor Daily News doesn’t have metered usage, and instead has annoying Google surveys and its army of unpaid bloggers. I tried this out for a while, and the traffic was good due to the domain authority of the Bangor Daily News. Here’s the terms of service for this arrangement (I’m sure they’ve been updated, I received this in late 2011)

BDN Blogger Terms of Service

The Content is a Commodity

I’m skeptical of the Press Herald change to metered usage because I believe it will only drive traffic to the BDN. It’s playing into the BDN’s strength, and that’s the pageviews game.

The truth is that I can read the same article the Press Herald publishes on the BDN, with the exception of a few articles like “Unsettled” or a Bill Nemitz article. 95% of the articles published are a commodity.

Disruption at a National Level

We’re also seeing major disruption on a national level; new entrants like Buzzfeed, Upworthy, and Vox are scaring traditional news organizations like the New York Times. They have different organization structure, different revenue streams, and don’t have the baggage that traditional news organizations have.

Long story short, I believe there’s implications at a local level.

Prediction #1

In the next 5 years, the BDN or the Press Herald will cease to exist. Only one organization will survive. The only edge case that could change this is outside funding. There’s no way billionaire Donald Sussman will let the Press Herald die in his wife’s backyard. The same rule applies if a conservative billionaire purchases the BDN.

Prediction #2

Someone will smarten up and realize that there’s opportunity knocking. A new entrant will emerge, and hopefully will do the following:

  1. Fewer staff – less bloat.
  2. Digital-only – once again, fewer expenses. It’s pretty cheap to start a website nowadays.
  3. Real journalism – high-quality articles that aren’t a commodity
  4. Nimble – the new entrant will be much more flexible than the BDN or Press Herald.
  5. Master of Selling – the new entrant will persuade long-time journalists to join (could be equity, cash, or more freedom as a journalist)

I think the Maine Media Collective is onto the right idea. They’re creating high-quality content that’s memorable, and it’s also timeless (and also targeting people outside Maine.) The majority of news on the PPH/BDN is read, and 6 months later is irrelevant. A few examples of content I’d like to see instead:

  1. The East-West highway debate
  2. What’s going on in Millinocket? (a video series or something similar)
  3. An in-depth look at the industries that used to shape Maine (I always love hearing “old-timer” stories from my grandfather and grandfather-in-law.)
  4. The offshore wind effort (I’d love for someone to explain how they generated power in calm seas…hint, they fed power back from the grid )
  5. The Peter Vigue story
  6. The incestuous relationship between the University of Maine System and it’s “child” universities (specifically the shuffle of administration from one school to another)
  7. Brain drain


Anways, this is just a collection of my thoughts. I’d love to see someone come in and shake things up.

Read More
AB Testing - Getting Started

A/B testing: a comprehensive guide to getting started

Over the past few years there’s been quite a bit of hype regarding A/B testing. From Obama’s election campaign, to Veggie Tales increasing revenue by 38%, I believe the hype is well-warranted and something that should be in every marketer’s toolkit.

I’ve had the opportunity to setup, instrument, and analyze numerous A/B tests for companies in different industries. I’ve made plenty of mistakes, and found some winners along the way. It’s been an eye opening experience, and the purpose of this guide (yes, it’s going to be a long one ~ 4000 words) will be to give you the most comprehensive A/B testing resource online (well, at least that’s the goal). I’ll start from the very basics, including organizational structure, to best practices (and things you should avoid).

Read More

Why User Testing Services are Useless

Building software that people enjoy using isn’t  an easy task, and it takes a ton of effort.

It’s critical that you get consistent, honest feedback to help you create a better experience for the end user. In an effort to create this feedback loop, user testing sites have real people record themselves visiting and interacting with the site.

While I want to love what they are doing (I certainly agree with their mission), I find myself despising these services and finding them to be completely useless.

Why? Let me explain…

Read More

The Growth Team: The most impactful team the Enterprise doesn’t have…..yet

It’s been about a month since I started working at Safari Books Online, and I’ve told a few of my close friends that I doubt I will ever work at a startup again…unless it’s my own (which I have no plans to do at the moment.)

This might sound strange coming from someone who enjoyed working at early stage tech companies, but there’s a gold rush in the enterprise, and very few people are talking about it.

In my opinion, the role of a numbers-driven marketer has never had more of an impact. More and more businesses are being built online, yet decision-making is the same its always been. The enterprise makes decisions based on the highest-paid person’s opinion (Hippos), and while a savvy executive is a major asset, there’s a new kid (or team) on the block that will shake things up.

Read More

More Accurate Acquisition Funnels with Mixpanel

I’m a big fan of Mixpanel for analytics. I’ve written about how I do A/B tests in Mixpanel, but over the past week I learned some really important things that I’d like to pass on.

Imagine a typical registration process from a homepage. The person visits your homepage, decides that they are interested, and creates an account. Clearly this signup flow can easily be tracked in Mixpanel. It might look something like this.


What’s the conversion rate on this funnel above? Here’s where things get interesting….

Read More

Growth/Marketing Interview Tips: My Learnings

Over the last few weeks I finished up my time at YesGraph, and have been exploring other opportunities and doing some contract work in my free time.

I’ve had the opportunity to connect with several companies here in Boston and SF, and the demand for marketers who work on driving growth is very high. This should serve as a no-brainer (as every startup is looking for exponential growth), but I was surprised and happy that companies are placing a high priority on this skill-set/mindset.

I’m compiling this post because there’s many articles about specific growth “hacks”, but very little information about what it’s like to get hired as one of these growth/marketing people. I’ll try to explain my learnings along the way and provide practical insight on how to navigate this process.

Read More

The Startup Marketer’s Experimentation Process

Over the past month, I’ve really tried to take a hard look at how I personally do marketing online. Specifically, I’ve been trying to create processes that I can use at any company as I progress through my marketing career. I wrote about how I onboard myself at a new company, but my goal with this post is to dive a bit deeper.

Before I jump into specifics, I believe that establishing a process around marketing experiments is one of the biggest competitive advantages you can have. So many marketers try tactics, and never document results (I’m guilty of this.) Even worse, there’s no “formula” to how you learn. This is bad, and I’ve been trying to change this, so I figured I’d share my process around experimentation. It’s still a work in progress, so any feedback is appreciated.

Startup Marketer's experimentation process

Read More
1 2 3 10