Going It Alone


The other day I watched a webinar with two managing directors about what it takes to join Techstars.  The first discussion point was about solo founders.  I’ve been wrestling with how to talk about my own status as a solo founder so I am going to try to create a narrative about not just why I think I can be successful, but also possibly help other entrepreneurs formulate their case.

The theory of a ‘team’ to start a new company is that you bring together people with complementary skills.  Typically at least one is technical and one product/business focused.  I think this strategy is really useful for young founders.  Their breadth of experience is just not broad enough to extrapolate how to handle new situations on the side where they have limited expertise.  I’ve noticed this more in the past few years as I get more face time with newly minted college grads in our office.  Note that we hire some very well qualified candidates from top schools, but they still lack skills (architecture, customer focus, basic understanding of business, politics).  But if you put a few younger people together, you usually cover enough ground to make them effective.  In which case, multiple co-founders make sense.

Between my finance degree, accounting stints, and years in consulting, I have a pretty solid background for understanding ‘business’.  I’ve spent a number of years recently as both project manager (making sure a team gets things done) and product manager (setting the vision for what the team is going to do).  No one would call me a ‘techy.’  However, I have fairly decent SQL and database design skills.

But what I really do well is something that many can’t.  I can work with a customer to craft a vision for the product, design a flexible solution for that problem and then communicate that concept to a development team.  Over the past 14 years of being at Fidelity, I have been coordinating these efforts with teams in North Carolina, Texas, Boston, Ireland, India, and China, all from our home base here in NH.  At the worst, my dev team was split among 4 of these sites simultaneously.

Sometimes I did well.  My most recent design challenge leveraged 20+ developers working on a solution in multiple sites on different components and technologies.  We came in on time and under budget.  Other projects were not so successful.  On one, our inability to convert large datasets accurately, led to missing our install window by a full quarter.  I have worked dozens of complex projects and learned from each one.

These experiences have proven to me one undeniable and consistent fact.  It is the strength of the design that was the most important factor in our success.  We worked most effectively when I was in sync with the team, communicating the concepts to the developers, letting them work through the details in the code.  Between shifting sites, pro-serve resources and changes with business partners, we are always cycling new associates in and out.  As long as I could brief them on the vision, their part in the whole picture and what was expected, things went well.  Unfortunately, perpetual change is a reality on any project, and subsequently managing that change is a critical skill to success in a project that is scaling.

Further, when I truly understand the problem and 100% own the solution design, I can work with any team.  Experience affords you the ability to talk to people and build a relationship because inevitably you have shared lessons that help bridge the gap of newness.  Team is more than proximity or friendships.  It is empathy, understanding, communication and setting clear goals.  It is also culture.  Books such as Extreme Ownership, and Team of Teams have taught me lessons that I use to build culture every day.

As I look to head out on my own and build TheMissionZone in earnest, I have decided that being a solo founder with a virtual team, is the optimal strategy for me.  (I also plan to write code, because it is a valuable skill.)  I believe that creating the infrastructure where I am able to grow an organization designed to scale right from the outset, is the best way to deal with challenges that will arise later.  Also, since I am not 100% sure what parts of the product are best to develop first, I can’t necessarily nail down the skills needed for a technical co-founder.  Flexibility now, is my most important HR asset.

There is also the ‘too many chiefs’ problem.  And I don’t believe this should be understated.  I keep hearing about startup founders that fight, disagreements on vision, market segment, etc.  Given all the input that is available through customers, colleagues, coaches, mentors and even through professional meet-up groups, a CEO really doesn’t lack objective opinions.   A co-founder has the potential to muddy the decision making process.  Right now, I don’t need that.  I need to move fast and break shit.

And then there is the whole ‘adult’ problem.  I am old.  There is no “living on ramen” for me.  I couldn’t convince my peers to quit their job to come join me.  Getting paid in equity for a 23 year old living at home is fine, but it doesn’t feed the kids.  My network are all adults, they have real lives and families.  Would they quit and take a pay cut for a paying job with equity and added flexibility without the political BS of the corporate world?  Probably.  At some point I will start making those calls.  I may be able to get myself into a comfortable position to quit my day job, but I can’t reasonably expect that of others.  Many of these friends continue to be advisers and I lean on them constantly.

Given what I have laid out above, I know I would function well as a solo founder.  But how does this fit into a general set of personal characteristics and approach that might help determine if you might also be well suited as a solo founder?  I will try to spell out those desireable characteristics below…

  • Have a rock solid design.  Create a design based on components so you can leverage a disparate team
  • Design for interoperability of the plug in components
  • Know your culture before you start, it can always evolve, but there has to be a foundation and understanding for those that join.  People want to know what they are walking into
  • Have a plan of how you will scale the team both temp resources and full-time
  • Be sure you define roles well.  Have experience motivating and inspiring teams, coaching underperformers where necessary
  • Have a broad network and feel comfortable tapping it
  • Know your MVP before you build it.  You should already know the first test case and tackle it.  Pivot later
  • Have damn good project management skills and understand how to work in a matrixed environment with multiple priorities
  • Be awesome at communication.  Know how to write clearly and coherently.  Know how to draw pictures to communicate with those for whom English is not their first language
  • Be humble and work with your customer to define a true requirement and how to solve problems most effectively.  Don’t just survey, understand the answers to questions
  • Have some sort of technical skills.  Understand how code has a logical progression and data tables can impact code.  Know how to communicate in boxes and lines.
  • Be able to visualize how rules based code will enable you to scale and not create hard-coded technical debt.  Recognize each of those tradeoffs
  • See the big picture of product and customer and revenue and partners
  • You must have basic accounting/finance skills.  Know time value of money, budgeting, spreadsheet modeling with variables, and product costing

This is not a complete list by any stretch.  I will continue to evolve this post over time.  Please give me feedback in any form!

There is no belayer or grigri when you are a solo founder.  So climb when ready…  Climbing!

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We Don’t Work on Powder Days

People always complain about how bad their employer is. They don’t care about me. They don’t support me. They don’t give me flexibility. I believe there is a way for a company to both instill loyalty from employees and in exchange, structure work so that employees are happier than they would be under a traditional work arrangement. I want my company to be genuine in its care for employees.

It starts with a recognition that no skier wants to work on a powder day. For those unfamiliar with the lingo, a powder day is a day on the mountain just after or during a huge storm that dumps a lot of snow, creating epic ski conditions. A powder day is foreseeable.  Usually a day or two before the storm, the weather guys will predict a storm, blizzard or massive nor’easter.  Timing for the day is critical. You want to be there as soon as you can to enjoy the snow before it gets all cut up. Powder days are rare. In the northeast you get maybe 4-5 per season. That makes them special. The enjoyment of a powder day, can make the whole season. They are the memories you cherish most. 

A powder day is a metaphor for times when you don’t want to be at work. It’s when something awesome and unplanned happens on a weekday.  Your Powder Day could be a school graduation, prom pictures, award ceremony, kid soccer game, World Cup in town, or sunny beach day. It’s whatever you hold most dear that is predictable, important, timely, and when you don’t want to be at work. 

My philosophy about a powder day is that I would gladly work more on the day before, the day after and maybe even check email periodically on the day, to take a guilt-free day off to head to the mountains the night before to enjoy fresh tracks on a blue-bird day. It’s not a vacation day. It’s a choice. Hell, I would gladly work both weekend days in exchange for actually getting first chair on a powder day. Yeah it means that much. 

The lesson is this, I want people working for me that know what they want in life. I admire people that have something that drives them. Something that makes work worth doing just to support your addiction. These people are your keepers. More importantly, if I give them the ability to experience the thing they love, even when they normally would be expected to be working, that drive extends onto the company that gave them that ability. 

If you want employees to care about the success of your company, then your company better care about the personal success and happiness of its people. The way I will do that is by employing a simple philosophy: People know they can get work done and they will gladly get it done when it makes the most sense for them, given competing priorities in life. Priorities include more than just personal/family sickness and emergencies. It includes the stuff that makes you happy.  We would gladly make trade offs for powder days. 

I am always happy when I am ripping down a mountain, snow kicking up in my face, cutting fresh tracks through 2 feet of fresh pow.  No company that I love, would make me miss that. I don’t work on powder days, neither should you. 

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Saturday night, Sara and I took the girls to the Kenny Chesney country-fest at Gillette.  We took the bus with some friends and of course had a great time tailgating.

Kenny Chesney show


I have to say that overall the show was ok, not great but not awful.  Thomas Rhett was one of the opening acts.  He was actually really good.  We didn’t get to see Old Dominion.  Honestly, I thought Rhett was better than Chesney.  Kenny Chesney is kind of like the George Thorogood of country music.  You can see the influence of Jimmy Buffett too.  He sings a lot of feel good drinking songs that generally have an awesome sense of nostalgia.  I’m not saying there is anything wrong with that, it’s just really superficial.  When you see his stage show, that superficiality comes through.  At one point he asked us to celebrate with him that it is 2017 and this is his 17th show at Gillette.  The crowd roared.  Come on, really?  What does that even mean? He does a lot of running around and skipping in his ‘dancing’ and he seems to be only able to hold the mic in his right hand and slap his thigh or make a lot of hip-hop hand gestures, and that’s the extent of the show.  The band is pretty talented though, that is for sure.  He rarely plays guitar, but the other guys are solid.

I say all this because it made me think back on an unfinished blog post about the BEST show I have ever seen.  Now granted, small venues are much easier to rock than 60k in a stadium.  But overall I have more respect for the music, the lack of lecturing BS and the creativity in a production.

Back in April, Sara and I saw Squirrel Nut Zippers and Ozomatli at the Capitol Center in Concord.  I am a huge fan of Ozomatli, these guys bring a great blend of what I might guess is the soul of LA and I dig it.  SNZ I have been following for at least 20 years back to when they released Hell in 1996.  I am just in awe of how they fuse styles and produce modern hat-tips to the classics, most especially, Cab Calloway.  I have crappy iPhone footage, but watching the Ghost of Stephen Foster play live, while the video runs on the in-house screens, was just awesome.  If you ever want to know how music can ‘feel’ in a way to balance an image, watch this video.

But what I really loved was how they ended the show, and it was an experience I will never forget.  SNZ and Ozomatli collaborated on a song called “Alley Cat“. Which they played together on stage.  Full disclosure, I like multi-threaded melodies and when you put that many instruments and talented musicians on stage, you get to experience so much complexity that it is over-stimulating in a way that let’s one lose themselves in listening to the music.  That happens for me.

At the end of the song, they pivoted to some drum laced rhythm and all the guys picked up portable instruments and started marching through the audience.  As it was happening, we just figured they would march back on stage like all bands do.  Nope.  They disappeared out the back.  We could still hear them playing but in a distance.  So we headed out.  I would describe the following ‘experience’ as nothing short of spectacular.  These guys all started jamming in the lobby of the Capital Center to a heavily modified montage of Tequila and other classics, literally surrounded by the audience.  It was so much fun.  Blew my mind how they pulled it off.

Maybe it’s impossible for a big time act to have this kind of intimacy with the audience.  But I have no interest to be lectured by some self-absorbed pop star and their thought du jour (read: Tim McGraw, Taylor Swift, Bono, etc).  I prefer authentic experiences that make me rethink how things can be done, and that includes the simple things, like going to a music show.  So I will continue to buy the music of the big pop acts, but I highly doubt I will do much more to shell out big cash for these shows that always seem to underwhelm.  The smaller acts work so much harder and are genuine.  I like that more.  Those are the shows that amaze me.


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The Lights Are Out


There are a lot of problems in this country, both in business and politics.  I think leadership is at the forefront of these problems.  As I see the success and failure of various leaders, I am starting to see a paradox that should concern us all.  Many senior leaders are promoted to their positions based on their confidence which often presents as blatant arrogance when you look at it a little deeper.  But that same arrogance limits their ability to lead in a way that breaks new ground and disrupts the relevant domain.  As Bezos says, “it is always Day 1”.  Which means, you have to always be thinking creatively about disrupting every single thing you do and observe.

I was listening to a talk by Scott Berkun who argues that “All ideas are made from other ideas.”  Nothing is ever really new.  That which seems new just involves leveraging other ideas, combining them in unique ways, and turning the result into something new.  In order to do this you have to listen and learn and ingest the ideas around you.  That fails when you are arrogant.  People that think they need to prove that they know a little about everything always feel the need to talk, when instead they should be listening for the bits of detail that they DON’T already know.  There is no need to continue talking about what you know while listening to someone who clearly knows something different.  You might actually learn something.  I have been dealing with this arrogance for years and I am so sick of it.

The other day I met with a VP of Architecture to discuss how I can get my hands on some data.  Our team is charged with finding staff efficiency.  It is a well documented fact that a significant part of an office worker’s day is spent in email.  Fido is no exception.  And so in wanting to get stats on emails from certain groups that we suspect of driving excessive work, this guy starts lecturing me that I really don’t need this data.  Email is not a problem.  Who cares about email.  I don’t spend any time there.  I reply that we have to be thinking about email because it occupies so much time and that we should be considering tools like Slack that get around the inefficient 1980’s mentality of asynchronous communication.

He continues.  Email is never going away.  It is a communication tool.  I use it to communicate with my team and peers and my leadership.  You can just use filters.  I filter out all other email and I deal with it whenever I get time.  Slack is a collaboration tool, it will never replace email.  Email is never going anywhere, it is a communication tool.

[Full Disclosure – I have played with Slack, but it is not supported at work, so I have never used it in a professional context]

I started to argue with this guy and wanted to point out all the inconsistencies in his logic and as a leader of technical architecture, isn’t it specifically his job to look for new technology to find ways to let us be more successful and productive?  But I needed him to help me get a meeting with someone else, so I kept my mouth shut (believe me, it was just as hard to do that as it is for you to believe that I actually DID it!).

Here is where arrogance kills his ability to lead.

  1. If a coworker is telling you there is an issue for a constituency you support, how can you possibly argue that it is not an issue because it isn’t one for you?  That’s like “Poverty isn’t an issue for people because I am not poor, why don’t they just do what I do?”
  2. One of the marks of a great leader is strong communication, yet this knucklehead specifically filters out communication channels on the one tool that he labeled as his communication vehicle.
  3. Subordinates, peers and leaders are EXACTLY the people you should be collaborating with!  Why would you not want a tool to help with that?  Further, the people that you would communicate with (a lower intensity than ‘collaboration’) you filter out of the tool you use for communication?  The arrogance of this nonsense is spectacularly irresponsible.
  4. This yahoo interviewed me for a data architect role on his team a few years ago but instead gave the job to someone almost as arrogant.  But he had no idea who I was and started lecturing me on file layouts and my ability to analyze the data I specifically asked for, so I could analyze it.

When arrogance occupies thought leadership roles, it kills any innovation from beneath because that arrogance assumes that it knows more than anyone under them.  It also kills that company’s ability to innovate from that level because these people are incapable of accepting new ideas from anywhere else.  Some people actually do know enough to innovate on their own.  But they get to that point by being sponges to knowledgeable people around them.  Clearly they don’t become arrogant and just decide that they have reached the end of all information and they are done listening to people.  That doesn’t make sense.  Please don’t talk about Steve Jobs.  A logical argument based on an exception, is not conclusive.

You can have the most inspirational visionaries leading a company, but if you pad the levels under them with arrogant people incapable of growing, that organization will die.  And if you seed the very senior-most levels with arrogance, then no matter what talent you have beneath, it never sees the light of day.  Think about the leaders in our country, business, organizations, your friends.  Imagine times when you have seen good ideas around them or from you and what they did.  When you feel they are too preoccupied with what they already know, does that make you feel good about the future?

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Let Me Recover You

It’s my birthday.  We have a few traditions but one I almost never miss is to get in a workout.  I had a really good run today.  I put together a pretty cool playlist and went out strong.  I should start every run with John Butler Trio’s Funky Tonight because I was flying.  I decided that I was going to really push myself.  My goal is always 8 miles in 1 hour.  I’ve only done it once, but I got close today.

Last year at 20X, we were pushed to the breaking point.  Just when it looked like one of us was about to quit, the coaches would get in your ear and quietly push you to meet the challenge of the evolution.  They’d say, “Come on, you can do this.” or “Don’t give up now.”  The incentive was, “Let Me Recover You.”  The idea is that they give you the end point, they are telling you that they want you to get to the end so they can let you recover and catch your breath.  They are saying, let me give you a break, all you need to do is push a little harder a little longer and you will be there.  It’s a subtle motivation that can help you push yourself to limits you didn’t think were possible.

When you are watching your pace on the watch, you get immediate feedback on how hard you are pushing the limit.  I am definitely out of peak shape.  Up 2 of the hills, I almost puked.  But I kept pushing, and a little voice from my subconscious was whispering in my ear, “Let me recover you.”  Get to the next mile, the next corner, the next house, the next plant.  Each milestone brings a catharsis that lets you keep going to the end of the run.  I coached myself, let me recover you.

IMG_3577 (2)

You can see I spiked my heart rate to 196, I am guessing that’s when I was at the edge.  It feels good to see the success of your effort.  I know that coaching myself, let me push to the edge.  And my recovery felt all the better.

I got a lot of things sorted out in the past month or two.  It’s been satisfying to have a plan and know where things are going.  I feel as if the past few years has been one big workout and I have been pushing myself hoping for a little break.  It is finally hitting.

While in the struggle, you don’t know if a recovery will come.  Hope is not a motivator.  But comparing my life to the run today, I am starting to think that I have the ability to recover myself simply by the act of pushing even harder through the toughest parts of life.  I’m pretty good at handling strife.  I can handle the stress, and I move through it pretty well.  But I can honestly say that when it gets hard, I don’t push myself PAST the breaking point to tackle the challenge.  I’m talking about pushing so hard that you make that experience even more painful, knowing that a recovery is coming.

I’ve never handled my personal life this way before.  But I almost always do when it comes to athletics and physical challenge.  That makes no sense, especially for a guy who hates hypocrisy and inconsistency.  The next 5 months are going to be an intense push toward the big Jan 2 singularity.  Things are going to be hard.  With each new challenge, I am going to push through it harder than I ever have before.  Pushing myself past the breaking point.

Let me recover me.

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Declaration Day


On the drive home from Maine the other day, the gas station TV had a clip from Robin Meade wishing well to all service members no matter where they are on this 4th of July.  It got me to thinking, is the 4th really a day for the Military?

Veterans day is for active duty and past service members, while Memorial day is for those that gave the supreme sacrifice in the defense of our country.   But the 4th, otherwise known as “Independence Day” celebrates the signing of the Declaration of Independence, a document that identifies the reasons for the founding philosophies of why this nation should exist separate from the English monarchy.  I really don’t think it has anything to do with war, defense, the military or anything combative.  While we celebrate with fireworks, and that is a nice touch probably commemorating the “rockets red glare” as sung in the National Anthem, that actually has nothing to do with the signing of the Declaration of Independence.

In fact, the Document was a specific product of a bunch of citizen diplomats who self-organized and formed an intellectual and philosophical argument for a political position.  It was SPECIFICALLY political: “…it becomes necessary for one people to dissolve the political bands which have…”  How amazing a time must it have been when politicians actually formed arguments to support a position and even wrote them out and published them?  I have seen “positions” on web sites, but they are all just a bunch of mom and apple-pie goals and no rationale on how to get there.  I miss logic.  I miss philosophy.  I miss reason.  I am sick of the political climate that just yells at each other with half-truths citing fake-news (the original term, not what that a-hole has stolen it for) stories shared from a FB or Twitter post.  Candidate Trump’s health care policy philosophy? “I won’t let people die in the streets.”   As if others actually advocated for death.  What does that even mean?  What is the argument for it?  What are the action steps?

I’ve given up on the idea of running for office.  My brand of formulating an idea and building an argument around it, just doesn’t play in the reality TV world of politics these days.  I don’t form alliances.  There is no drama.  I don’t hate the person because they argue for an opposing position.  I could care less about “winning” as a goal.  But what I love about Declaration Day, is the notion that this country was founded by people who felt strongly enough about an idea that they formulated a rationale for a new way of thinking and wanted to engage in discourse about all of their supporting points.  They didn’t spout off about a wall of naval mines around the east coast to prevent the British ships from landing.  For me, this day will celebrate those of us that use our hearts, emotions and spiritual connection to the world to influence thoughts in our mind that we cogently share with others in the hope that we influence others to think about things in new ways or new directions.  Maybe they agree with us, maybe we see validity in their counter-points.  Maybe we work together to find a common ground whose sum total is more than either argument in isolation.  My political hopes may be dead, but I will never give up on the notion of creating and sharing ideas.

While we were theoretically “independent” as of the 4th (or the 2nd, read the story), celebrating something that is theoretical seems to cheapen the day for me.  I prefer to celebrate the declaration, the sharing of ideas.  That was the monumental achievement of the day.  For those of you producing new content, new ideas, fact-based analysis, waxing philosophical without yelling, or generally just sharing your rational based thought with the world… this bud’s for you.  Throw some bags, grill some meat, drink beer, hit the pool/boat and envision the explosion of new ideas in each flash of color in the night sky heralding the birth of knowledge.

Happy Declaration Day!

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The Blame Game

I started following Jocko Willink on Twitter a year ago after I heard him interviewed on the Tim Ferris podcast.  He is pretty intense and inspirational.  He posts a lot of pictures of his watch at 4:30 am before his workout and then the results with sweat all over the floor under a barbell.  Hooyah.  I’ve had a few workouts like that, but not every day.  Yesterday I stumbled on a TED talk where he talked about the nobility of “Extreme Ownership” (which is also his book title), how it is affected by the fog of war, friendly fire and owning your mistakes.  It’s 13 minutes and a must watch for anyone in business.  I wish I could get the Fido senior leaders to watch it.

At work, I always take responsibility for my mistakes.  Several years ago we had a project come in pretty late and I got dinged for it.   But I owned up to the fact that my estimates for designing the solution were far understated and when things started going bad because of extraneous factors, I did not raise awareness.  One person got fired.  Others moved on.  I stayed and it hurt my career for sure.

Under heavy pressure, we took a risk.  If you take a risk and you get punished for admitting a mistake, then that is not a place you should work.  Jocko just made me realize how poignant that fact is.  I didn’t blame a lot of people who deserved blame.  We tried to hit an aggressive timeline and we missed.  No one died.  Yet in the most severe case, in a truly life AND death experience, in the military where people are always held accountable, he took ownership and was not penalized.  What does that say about where I work and the mentality of “stretch” goals, taking risks and working hard?  With only modest positive results for a successful risk (aka hitting your goals) why would I ever take a risk again?

As obvious as the work case, you have to take Extreme Ownership in your personal life too.  Last year in the midst of a rough time, I learned that I was not REALLY taking responsibility for all my actions.  I always felt that I owned up to things I did and said or often said incorrectly.  But what I noticed is that I very frequently used the expression “I’m sorry if…”  I want you to burn that expression into your consciousness.  Listen for it when polititcians apologize.  Or when you do.  Or colleagues.  What I learned is that no matter what you intended, you actually DID something.  There was a result of your action.  Cause and Effect.   The “if” becomes a copout and negates the apology.  It’s blaming something else, something intangible.  It puts the responsibility somewhere else.  You aren’t owning anything when you use “if”.  Often “if” is followed with “you”.  How often have you heard “I’m sorry if you were offended by…”  That puts the ownership squarely on the other party.  That is wrong.  There is no “if”.  As Jocko put it, taking Extreme Ownership should hurt.  It hurts your ego and your pride.  But if you are a person of character, you own it.

What punctuated this concept for me is that Jocko noted that when you do it correctly, Extreme Ownership has benefits up and down the chain of command and those around you.  His men took full responsibility for their individual actions.  Most importantly, what he enabled was them to do their job without the burden of being the leader and being responsible.  The ultimate responsibility was on him.  Up the chain too, his commanders recognize that he was actually doing his job, in the good and the bad.  He owns both.

For friends and family around you, when you take Extreme Ownership of your actions and their result, regardless of intent, I promise you, people will believe in you and trust you and care about you in ways they never have before.  Don’t spread blame.  Own it.  Check your ego at the door.  I constantly have to watch my words and the impetus to say “if” is strong.  The game I now play is in noticing it in others, and when I hear it, I see them as weak.  I see them as petty, looking for an out.  Be strong, play the game.  You will find that you win, when you take ownership of each loss.

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