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Jun 4 2006

What Kind of Entrepreneur Do You Want to Be?

What Kind of Entrepreneur Do You Want to Be?

I had a great time at Princeton reunions this weekend, as always.  As I was talking to random people, some of whom I knew but hadn’t seen in a long time, and others of whom I was just meeting for the first time, the topic of starting a business naturally came up.  Two of the people asked me if I thought they should start a business, and what kind of person made for a good entrepreneur.

As I was thinking about the question, it reminded me of something Fred once told me — that he thought there were two kinds of entrepreneurs:  people who start businesses and people who run business. 

People who start businesses are more commonly known as serial entrepreneurs.  These people come up with ideas and love incubating them but may or may not try to run them longer term.  They:

– generate an idea a minute
– have a major case of ADD
– are easily distracted by shiny objects
– would rather generate 1 good and idea and 19 bad ones than just 1 good one
– are always thinking about the next thing
– are only excited by the possibility of what could be, not what is
– are more philosophical and theoretical
– probably shouldn’t run the companies they start for more than a few months, as they will frustrate everyone around them and get bored themselves
– are really fun at cocktail parties
– say things like “I thought of auctions online way before eBay!”

The second type of entrepreneur is the type who runs businesses (and may or may not come up with the original idea).  These people:

– care about success, not just having the idea
– love to make things work
– would rather generate 1 idea and execute it well than 2 ideas
– are problem solvers
– are great with people
– are maybe less fun at cocktail parties, but
– you’d definitely want them on your team in a game of paintball or laser tag

Neither one is better than the other, and sometimes you get both in the same person, but not all that often.  But understanding what type of entrepreneur you are (or would likely be) is probably a good first step in understanding whether or not you want to take the plunge, and if so, what role you’d like to play in the business.

Jun 13 2004

CEO, Party of Two

We spent the weekend in Hudson, New York, a charming, urban-renewing town about two hours north of the city. My cousins Michael & Marianne opened a wine store called Hudson Wine Merchants on the main drag in town, Warren Street (343 Warren St. to be exact, you should definitely check it out if you’re ever in Hudson).

The store opened for the first time Friday evening, and we had the first full day on Saturday. Mariquita and I, and some other friends of Michael & Marianne’s, helped do everything from stock the shelves, to clean the windows, to use the price tag gun (fun!), to work the register and the very fickle POS software, to watch my cousin’s daughter as she rode her tricycle through the store. It was fun but exhausting. It inspired a few different postings here, which I’ll work on in the coming days.

The first thought I had is that being CEO of a two-person company has a lot in common with being CEO of a 200-person company, or, I imagine, a 20,000-person company:

– You worry incessantly about keeping your customers happy and providing a great customer experience and the right product

– You have numbers running in the back of your head all the time. How much are you selling? At what margin? Are you making money?

– You work your ass off and frequently put business first in order to see it succeed

– You think about the little things, the big things, everything, 24 hours a day

Obviously, there are many differences between running a two-person company and running a much larger organization as well; of course, the biggest is managing, developing, and worrying about lots of employees’ welfare. But it struck me that there are more similarities than meet the eye.

Nov 6 2012

Startup CEO (OnlyOnce- the book!)

Startup CEO (OnlyOnce – the book!)

One of the things I’ve often thought over the years since starting Return Path in 1999 is that there’s no instruction manual anywhere for how to be a CEO.  While big company CEOs are usually groomed for the job for years, startup CEOs aren’t…and they’re often young and relatively inexperienced in business in general.  That became one of the driving forces behind the creation of my blog, OnlyOnce (because “you’re only a first time CEO once”) back in 2004.

Now, over 700 blog posts later, I’m excited to announce that I’m writing a book based on this blog called Startup CEO:  A Field Guide to Building and Running Your Company.  The book is going to be published by Wiley & Sons and is due out next summer.  The book won’t just be a compendium of blog posts, but it will build on a number of the themes and topics I’ve written about over the years and also fill in lots of other topics where I haven’t.

The catalyst for writing this book was Brad Feld.  Brad has been a friend, mentor, investor, and Board member for over a decade.  We’ve had many great times, meals, and conversations together over the years, not the least of which was staggering across the finish line together at the New York City Marathon in 2005.  Brad started writing books a few years ago, and I’ve been peripherally involved with them, first with Do More Faster:  TechStars Lessons to Accelerate Your Startup (I contributed one of the chapters) and then with Venture Deals:  Be Smarter Than Your Lawyer and Venture Capitalist (I wrote all the “Entrepreneur Perspective” sidebars).

Those are great books, and they’ve been incredibly well received by the global entrepreneurial community.  But then Brad got the bug, and now he’s in the middle of writing FOUR new books with Wiley that will all come out over the next year.  They are:

These four books, plus the two earlier ones, plus Startup CEO, are all part of the Startup Revolution series.  While I’ll continue to do most of my blogging and posting here on OnlyOnce, I’d also encourage you to check out the Startup Revolution site and sign up to be a member of that community.  I’ll be doing some things on that site as well in connection with Startup CEO, and it’s a more concentrated place to post and comment on all things Startup.  In addition, we’ll be putting a bunch of add-ons to the book on that site closer to publication time.

I hope Startup CEO becomes a standard for all new CEOs.  I don’t think I have all the answers, but at least others can benefit by learning from my 13 years of successes and mistakes!  Now all I have to do is go write the darned thing.

Mar 18 2009

Book Short: Be Less Clever

Book Short:  Be Less Clever

In Search of the Obvious: The Antidote for Today’s Marketing Mess, by Jack Trout, is probably deserving of a read by most CEOs.  Trout at this point is a bit old school and curmudgeonly, the book has some sections which are a bit repetitive of other books he and his former partner Al Reis have written over the years, he does go off on some irrelevant rants, and his examples are a bit too focused on TV advertising, BUT his premise is great, and it’s universally applicable.  So much so that my colleagues Leah, Anita, and I had “book club” about it one night last week and had a very productive debate about our own positioning and marketing statements and how obvious they were (they need work!).

The premise in short is that, in advertising:

Logical, direct, obvious = relevant, and

Entertaining, emotional = irrelevant

And he’s got data to back it up, including a great case study from TiVo on which ads are skipped and not skipped – the ones that aren’t skipped are from companies like Bowflex, Hooters, and the Dominican Republic, where the presentation of the ad is very direct, explanatory of the product, and clear.  His reasons why advertising have drifted away from the obvious are probably right, ranging from the egos of marketing people, to CEOs being to disconnected from marketing, to the rise in importance of advertising awards, and his solution, of course is to refocus on your core positioning/competitive positioning.

It is true that when the only tool in your box is a hammer, everything starts to look a bit like a nail, but Trout is probably right in this case.  He does remind us in this book that “Marketing is not a battle of products. It is a battle of perceptions”– words to live by.

And some of his examples of great obvious advertising statements, either real or ones he thinks should have been used, are very revealing:

  • Kerry should have turned charges that he was a flip-flopper in 2004 around on Bush with the simple line that Bush was “strong but wrong”
  • New Zealand: “the world’s most beautiful two islands”
  • The brilliance of the VW Beetle in a big-car era and “thinking small”
  • Johnny Cochrane’s winning (over)simplification of the OJ case — “If the glove doesn’t fit, you must acquit”
  • BMW is still, 30 years later, The Ultimate Driving Machine
  • “Every day, the Kremlin gets 12 copies of the Wall Street Journal. Maybe they know something you don’t know.”

If you are looking for a good marketing book to read as a refresher this year, this one could be it.  And if you’re not a very market-focused CEO, this kind of thinking is a must.

And for the record, the library of books by Trout and/or Reis (sometimes including Reis’ daughter Laura as well) that I’ve read, all of which are quite good, is:

Jul 5 2004

American Entrepreneurs

Fred beat me to it. I wasn’t at a computer to post this yesterday on the actual 4th of July, so today will have to do. I’ve read lots of books on the American revolution and the founding fathers over the years. It’s absolutely my favorite historical period, probably because it appeals to the entrepreneur in me. Think about what our founding fathers accomplished:

Articulated a compelling vision for a better future with home democratic rule and capitalist principles. Life, liberty, and the pursuit of happiness is really the ultimate tag line when you think about it.

Raised strategic debt financing from, and built critical strategic alliances with France, the Netherlands, and Spain.

Assembled a team of A players to lead the effort in Washington, Adams, Jefferson, Franklin, Hamilton, and numerous others who haven’t been afforded the same level of historical stature.

Built early prototypes to prove the model of democratic home rule in the form of most of the 13 colonial assemblies, the Committees of Correspondence, and the Articles of Confederation.

Relentlessly executed their plans until they were successful, changing tactics several times over the years of 1774-1783 but never wavering from their commitment to the ultimate vision.

Followed through on their commitments by establishing a new nation along the principles to which they publicly committed early on, and taking it to the next level with the Constitution and our current form of government in 1789.

And let’s not forget, these guys accomplished all of this at a time when it took several days to get a letter from Virginia to Boston on horseback and six weeks to get a message across the Atlantic on a sailboat. Can you imagine what Washington would have been able to accomplish if he could have IMd with Adams in Paris?

So happy 4th to all, with a big thanks to this country’s founding fathers for pulling off the greatest spin-off of all time.

Jul 20 2006

Feedburner…They’re Real AND They’re Spectacular

Feedburner…They’re Real AND They’re Spectacular

Sometime in early 2004, I met Dick Costolo, the CEO of Feedburner.   We met about at the same time he also met Fred and Brad (I can’t remember who met who first), both of whom subsequently invested in the company.  We hit it off and had a number of informal and formal conversations over the past two and a half years about online media, the interplay of RSS and email and blogs, and entrepreneurship.  Feedburner and Return Path have developed a still-somewhat nascent partnership as well to bring ads in feeds and ads on blogs to Return Path’s Postmaster advertisers.

I was recently fortunate enough to be invited by Dick and his team to join Feedburner’s Board of Directors.  You can read the official note (as official as Feedburner gets!) on Feedburner’s blog here.  I am huge Feedburner fan and am jazzed to be part of their extended team.  The company is impressively leading its market of RSS publisher services and RSS advertising.  It’s all very reminiscent of the early days of email, and the early days of banner advertising before that.  More than that, though, I’ve been incredibly impressed with how the company operates.  They execute swiftly and flawlessly, they have a ton of fun doing it, and they have a very authentic voice and ethos for communicating with and handling their customers that I admire tremendously.  Very Cluetrain Manifesto.

In a much earlier posting, I wrote that entrepreneurs should join other boards as well to get more experience with how different organizations are run and how different board dynamics work, so I guess this means I’m following my own advice.  And so far, it’s all true — I’ve gotten a lot out of the first couple of meetings I’ve attended.  It’s a little weird for me to be the “old media” guy around the table (old meaning web and email, of course), so I’ll have to work hard to not be a Luddite and keep pace with all the new toys.

Jan 10 2006

New Media Deal, Part II – the We Media Deal

New Media Deal, Part II – the We Media Deal

My original New Medial Deal posting from August, 2004, is my favorite posting of all 220 or so that I’ve done to date. It has the most clicks of any posting I’ve done. People mention it to me all the time. I even used it as the foundation for the preface to our book at Return Path, Sign Me Up!

The general thesis (although the original posting is short and worth reading) is simple. Old Media was one-way communication – they produce it, you consume it, and Old Media had a deal with us: they give us free or cheap content, we tolerate their advertising. Think about your favorite radio station or an episode of The Office on TV. The New Media deal is an Internet derivative of that, that is founded on some degree of two-way communication: they give us free services and more targeted advertising in exchange for some of our personal data — just like the Old Media deal, we are willing make a small sacrifice, in this case, some pieces of our anonymity, in a heartbeat if the value exchange is there. This is true of everything from personalized stock quotes on My Yahoo! to the New York Times on the Web. The New Media Deal doesn’t replace the Old Media Deal, it just adapts it to the new environment.

But what about the new generation of services that have popped up on the web around peer production?  The ones that aren’t one-way communication or two-way communication, but community-oriented communciation.  (Note I am resisting hard calling them Web 2.0, but you know it’s there somewhere.)  Does the New Media Deal still apply, or are we on to something else?  I think the rules are morphing once again, and now there’s a new deal — let’s call it the We Media Deal — that builds on the “data as part of the value exchange” moniker of the New Media Deal. Like its predecessor deals, the We Media Deal doesn’t replace the New Media Deal or the Old Media Deal, it just adapts it for new types of services.

The We Media Deal has two components to it:  (1) the value of the service to you increases in lock-step as you contribute more data to it, and (2) the more transparent the value exchange, the more willing you are to share your data.

Ok – that sounds very academic – what do I mean in plain English? Let’s break it down.

1. The value to you increases in lock-step as you contribute more data.  This is something that probably wasn’t obvious with the original New Media Deal, since it wasn’t clear that if you gave My Yahoo! incrementally more data (one more stock quote, for example), you’d get more relevant ads or services.  It’s a pretty static value exchange.  But think about the new generation of web services around peer production.

– The more you use Delicious to bookmark web pages, the more relevant it becomes to you, and the more dependent you become on it as your own “Internet within an Internet.”

– The more you wite a blog or post photos to Flickr, the more engrained the act of blogging becomes in your daily existence — you start looking at the world, ever so slightly, through the lens of “that would make an interesting posting” (trust me).

– The more you use Wikipedia (or wikis in general), the more committed you become to Wikipedia as your first go-to source for information, and the more you get infected with the desire to contribute to it.

The bottom line with the first part of the We Media Deal is that the more you give to the system, the more you want and need out of the system.  A big part of peer production is that most people fundamentally, if quietly, want to belong to any bit of community they can find.  All these new web services of late have transformed the mass Internet from a read platform to a read/write platform, so now everyone can have a say in things.  The same reason eBay is cooler and bigger than the New York Times on the Web will drive this new generation of services, and new spins on old services, forward.

2. Next up — the more transparent the value exchange, the more willing you are to share your data.  Transparecy rules.  When you contribute to the web, you’re exposed, so why is trasparency a help and not a hindrance?  Let’s look at the same 3 examples.

– Delicious let’s you delete your account and all your personal data.  They’re blatant about it during the sign-up process.  The result?  It increases your trust in the network since you can easily exit at any time.

– Blogging and Flickr couldn’t be more transparent.  They’re personal printing presses.  If you’re good at it, you really have to think before you write. It’s you – you’re really hanging out there transparent for all the world to see – therefore you’re even more invested in what you write and derive even more value from the activity.

– Similarly, Wikipedia tracks who changes what, and if you make an error, the community will correct it in an astonishingly short time frame, keeping you honest.

The good news is that, while the We Media Deal is coming of age, our New Media Deal is alive and well and growing stronger as the web evolves as well.  Free services and more targeted advertising in exchange for some of your personal data makes a ton of sense when the right balance of service and data is there.  Transparency and control make the We Media Deal an even stronger stronger bond between company and individual, mostly because the bond is between company and community — the deal gets more solid the more we as individuals invest in it.

Aug 22 2004

New Media Deal

Americans have long operated under an unwritten deal with media companies (for our purposes here, let’s call this the Old Media Deal). The Old Media Deal is simple: we hate advertising, but we are willing to put up with an amazing amount of it in exchange for free or cheap content, and occasionally one of those ads slips through to the recesses of our brain and influences us in some way that old school marketers who trade in non-addressable media can only dream of. Think about it:

– 30 minutes of Friends has 8 minutes of commercials (10 in syndication!)
The New York Times devotes almost 75% of its total column inches to ads
– We get 6 songs in a row on the radio, then 5 minutes of commercials
– The copy of Vogue‘s fall fashion issue on my mom’s coffee table is about 90% full page ads

The bottom line is, advertising doesn’t bug us if it’s not too intrusive and if there’s something in it for us as consumers.

Since I started working in “New Media” in 1994, I’ve thought we had a significantly different New Media Deal in the works. The New Media deal is that we as American consumers are willing to share a certain amount of personal information in exchange for even better content, more personalized services, or even more targeted marketing — again, as long as those things aren’t too intrusive and provide adequate value. Think about how the New Media Deal works:

– We tell Yahoo that we like the Yankees and that we own MSFT stock in order to get a personalized home page
– We tell Drugstore.com what personal health products we buy so we can buy our Q-tips and Benadryl more quickly
– We tell The New York Times on the Web our annual income in order to get the entire newspaper online for free
– We let PayTrust know how much money we spend each month so that we can pay our bills more efficiently
– We let Google scan our emails to put ads in in them based on the content to get a free email account
– We give their email address out to receive marketing offers (even in this day and age of spam) by the millions every day

Anyway, after a few years of talking somewhat circuitously about this New Media Deal, my colleague Tami Forman showed me some research the other day that backs up my theory, so I thought it was time to share. In a study conducted by ChoiceStream in May 2004, 81% of Internet users expressed a desire for personalized content; 64% said they’d provide insight into their preferences in exchange for personalized product and content recommendations; 56 would provide demographic data for the same; and 40% said they’d even agree to more comprehensive clickstream and transaction monitoring for the same. All of these responses were stronger among younger users but healthy among all users. Sounds like a New Media Deal to me.

Don’t get me wrong — I still think there’s a time and a place for anonymity. It’s one of the great things about RSS for certain applications. And privacy advocates are always right to be vigilant about potential and actual abuses of data collection. But I think it’s becoming increasingly clear that we have a New Media Deal, which is that people are willing to sacrifice their anonymity in a heartbeat if the value exchange is there.

P.S. Quite frankly, I wish I could give spammers a little more personalized information sometime. They’re going to email me anyway — they may as well at least tell me to enlarge a part of my body that I actually have.

Sep 9 2011

9/11’s 10th

9/11’s 10th

I wasn’t yet writing this blog on 9/11 (no one was writing blogs yet), and if I had had one, I’m not sure what I would have written.  The neighborhood immediately surrounding the World Trade Center had been my home for more than seven years before the twin towers fell, and it continued to be my home for more than seven years after they fell.  That same neighborhood was Return Path‘s home for its first 18 months or so, across two different offices.  Like all Americans, the attack felt personal.  Like all New Yorkers, it was in our face.  But it hit home in a different way for those of us who lived and worked in Lower Manhattan.

For the seven years after the attacks, I stopped by Ground Zero on the morning of 9/11 to reflect and memorialize the event.  I won’t be doing that this year — between living outside the city, the kids, and the likely overwhelming crowds, it doesn’t make sense.  So this post will have to suffice as this year’s reflection on the 10th anniversary of that awful day.

My memories from that day and the weeks that followed are a little jumbled now, as memories often are.  The things I remember most vividly, both personal and professional, are:

  • The smell and the smoke.  Up until the New Year, over 3 months after the attacks, a plume of smoke was rising from Ground Zero, and the air had a putrid smell of burning everything — building materials, fuel, fragments of life
  • I had left the city that morning to drive to a meeting in Danbury, Connecticut at Pittney-Bowes with our then head of sales, Dave Paulus.  We both received calls on our cell phones at the same instant from Mariquita and Pam telling us to turn on the news, that a plane had crashed into the World Trade Center.  For a while, everyone assumed it was an accident.  We continued with our meeting, although it kept getting interrupted with more bad news coming in via our senior contact’s assistant, until she wheeled a TV into the conference room so we could watch for ourselves
  • I couldn’t get back into the city that night, so Dave and I crashed at my Grandma Hazel’s house in Westchester.  When I finally did get home, Mariquita and I met up and stayed with our friends Christine and Andrew on the upper west side and listened all night to the fighter planes cruising up and down the Hudson River, sentries on patrol
  • When we finally could go back to our apartment, we had to go on foot from Canal Street south, and we had to show proof of residence (in our case, a copy of our lease) to get past the military guards.  With no traffic allowed and no subways running in Lower Manhattan for a week or two, the streets had an eerie emptiness about them.  The prevalence of national guardsmen and NYPD patrols toting machine guns made it feel like a war zone
  • At work, where the Internet 1.0 meltdown was still in process, we were in the middle of negotiating a life-saving financing and acquisition of Veripost with Eric Kirby and George.  We hit the pause button on everything, but we picked back up and dusted ourselves off within a day and got those deals done within a few weeks and saved the company
  • We had one junior employee in our New York office who got into his car on the afternoon of 9/11, drove to New Hampshire, and never contacted us again.  Just completely blew a fuse and dropped out.  It wasn’t until we tracked down his parents a few days later that we even knew he was safe and sound
  • I was fortunate not to lose anyone close in the attacks, but my friend Morten lost over a dozen close friends who were all traders from his town in New Jersey.  He attended every single funeral.  How he got through that (and how others got through their many losses) remains beyond my comprehension, even today

The only thing I have really blogged about over the years related to 9/11 was my post Morning in Tribeca in 2004 when the skeleton of WTC7, the first rebuilt building, was going up.  Now that the Freedom Tower is rising, it finally feels like the Ground Zero site has great forward momentum and will in fact be fully renewed in a few years once the bulk of this construction is done and the tenants have moved in.  That will be a great day for New York, and for America.

May 24 2007

Book Short: Blogging Alone?

Book Short:  Blogging Alone?

I usually only blog about business books, but since I read Bowling Alone: The Collapse and Revival of American Community, by Robert Putnam, because of its connection to the topic of Internet community and social media, I’ll record some thoughts about and from it here.

It’s an interesting read, although a little long.  Putnam’s basic thesis is that America’s social capital — the things that have brought us physically and emotionally together as a country throughout much of the 20th century such as church, voting, and participation in civic organizations like the PTA or the Elks Club — are all severely on the decline.  The reasons in Putnam’s view are television (you knew all those re-runs of The Brady Bunch would eventually catch up to you), suburban sprawl, two-career families, and “generational values,” which is Putnam’s way of saying things like people in their 60s all read newspapers more than people in their 50s, who all read newspapers more than people in their 40s, etc.  He believes the decline is leading to things like worse schools, less safe neighborhoods, and poorer health.

The book does a good job laying out the decline in social capital with some really interesting and somewhat stunning numbers, but the book’s biggest shortcoming is that Putnam doesn’t do the work to determine causation.  I buy that there’s a correlation between less voting and less safe neighborhoods, for example, but the book doesn’t convince me that A caused B as opposed to B causing A, or C causing both A and B.  What I really wanted at the end of the book was for Putnam to go mano-a-mano with the Freakonomics guy for a couple hours.  Preferably in those big fake sumo suits.

The book was published in 2000, so probably written from 1997-1999, and therefore its treatment of the Internet was a little dated — so I found myself wanting more on that topic since so much of the social media revolution on the Internet is post-2004.  His basic view of the Internet is that it is in fact a bright spot in the decline of community, but that it’s changing the nature of communities.  Now instead of chatting with whoever is bowling in the next lane over at the Tuesday night bowling league on Main Street, we are in an online discussion group with other people who own 1973 BMW 2002 series cars, preferably the turbo-charged ones.  So the micro-communities of the Internet circa 2000 are more egalitarian (“on the Internet, no one knows you’re a dog”), but more narrow as well around interests and values.

What has social media done to Putnam’s theories in the last seven or eight years?  How have things like blogging, MySpace, LinkedIn, YouTube, and Photobucket changed our concept of community in America or in the world at large?  I welcome your comments on this and will write more about it in the future.

May 3 2013

Firsts, Still

Firsts, Still

After more than 13 years in the job, I run into “firsts” less and less often these days.  But in the past week, I’ve had three of them. They’re incredibly different, and it’s awkward to write about them in the same post, but the “firsts” theme holds them together.

One was incredibly tragic — one of our colleagues at Return Path died suddenly and unexpectedly.  Even though we’ve lost two other employees in the last 18 months to cancer, there was something different about this one.  While there’s no good way to die, the suddenness of Joel’s passing was a real shock to me and to the organization, and of course more importantly, to his wife.

The second was that I came face to face with a judge in the state of Delaware for the first time around some litigation we’re in the middle of now.  While I can’t comment on this for obvious reasons, you never think when you decide to incorporate in Delaware that a trip to a courthouse in Wilmington is in your future.

The third, which can only be described as bittersweet, is that we had our first long-time employee retire!  Now THAT’S something you never think about when you run a startup.  But Sophie Miller Audette, one of our first 20 employees going back to 2000 and the sixth longest tenured person at the company today, has decided to retire and move on to other adventures in her already rich life.  A quick search on my blog reveals that I’ve blogged about Sophie three times since I started OnlyOnce 9 years ago (as of next week).  The first time was in 2004 when I quoted her memorable line, “In my next life, I want to come back as a client.”  The second and third times were in 2005 and were about the company’s commitment to helping to find a cure for Multiple Sclerosis, which Sophie was diagnosed with almost 10 years ago now.  Sophie has been an inspiration to many of us for a long time, and while we’ll miss her day-to-day, she’ll always be part of the Return Path family.  Picture of her, me, and Anita at her “retirement dinner” earlier this week below.

Sophie retirement dinner

I always say that one of the best parts about being in this job for this long is that there are always new challenges and new opportunities to learn and grow.  The last couple weeks, full of firsts, proved the point!