This is going to be an interesting process.

I want the record to be up tempo and have some rhythm and momentum.  But of course, without a drummer and a lot of my own percussive skills, the songs all end up coming out sounding like acoustic folks songs.  Part of it will be getting Paul and myself and the band to stretch the limits of our imagination around the possibilities of the music.  And the other part will be allowing the stated intention of the record to settle into whatever the actual result ends up being.

Matt and I were saying we should have a seeded tournament.  A “Song Off” where top seeds and sure picks go up against lesser opponents and maybe we get a few people involved in this song off and ultimately winnow down the list in a different fashion.

I know that a few songs that I really like might not make it on the record.  And a few that I had only just written might make it.  And that’s how these things go.  Certain songs kind of offer themselves up for imagination.  And other ones feel more momentuous when you have the germ of an idea but somehow can’t seem to coalesce into something that feels like a complete whole.

Nevertheless, it’s nice to have the well to draw from and it’s nice to know that there are options.  Songwriting is so interesting because, for me, it’s all about the quick jab.  The quick punch.  The fist.  The pound on the table.  Not a fugue.  Not a concerto.  But an expression or a gesture that feels, by necessity, incomplete.  The incompleteness of songs and song lyrics lend them their beauty and their mystery and the power of these phrases and these musical moments lies in their stated intention and their unstated mystery.

For the sessions with Matt, the running time for 13 songs is 40 minutes.  Average song length is right around 2:50.  That’s just how I do it.  I am terrified of repeating something too often and having it be boring.  I’d rather have it be short and pithy and leave you wistful and nostalgic for a moment that just ended.

The funny thing about people and about masters imparting lessons is that it’s all impossible and besides the point, of course.  It’s not because Eno practiced a certain way of doing things or had a specific strategy in mind.  It’s because he has impeccable taste and great judgement.  And those things are very hard to teach.  The problem with reading self-help books or self-help blogs or whatever is that ultimately it simply comes down to being right and who is right most of the time.  Eno is right most of the time.  Another guy that jumps to mind is David Geffen.  Also someone that is right most of the time.

But that’s neither hither nor yon, as my English teacher used to say.  The thing that I’ve been thinking about and that Eno points to and that Dubber linked to is the following snippet:

“I think records were just a little bubble through time and those who made a living from them for a while were lucky. There is no reason why anyone should have made so much money from selling records except that everything was right for this period of time. I always knew it would run out sooner or later. It couldn’t last, and now it’s running out. I don’t particularly care that it is and like the way things are going. The record age was just a blip. It was a bit like if you had a source of whale blubber in the 1840s and it could be used as fuel. Before gas came along, if you traded in whale blubber, you were the richest man on Earth. Then gas came along and you’d be stuck with your whale blubber. Sorry mate – history’s moving along. Recorded music equals whale blubber. Eventually, something else will replace it.”

It’s interesting to think of it that way.  Because even though we’re all in 2010 and even though so many people are talking about the death of the album as the default format for a collection of songs.  I still find myself working on a new “album”.  And maybe it’s sort of back to the points that I made yesterday — that is I need to produce things within certain conventions in order to register my work with the cognoscenti that have the power to provide enhanced distribution to it.

So maybe the album is totally arbitrary.  And it’s nice to be cold and dispassionate and say that.  And shrug your shoulders.  Listen, bros, the jig is up.  Time for the next thing.  Albums are  a function of the physical means of production and distribution.  It’s an arbitrary amount of time based on how much sound a vinyl record could hold.

Maybe.

But you know, things flow in the world.  And there are submerged and hidden relationships between things.  And it could be totally arbitrary or it could be part of a series of implicit rhythms in the universe.  Maybe vinyl was created the way it was because there is something special about 45 minutes of music.

I suppose my point is merely that I do find something interesting in a series of 8-10 songs.  I like 35 minutes of music, I think.  I don’t really like 70 minutes of music.  I can’t sit and listen to a 70 minute record all the way through.  Not even really a 45 or 48 minute record.  But 35 minutes seems like a good amount of time to me.  Even if it’s on the internet.  Even if I have the ability to mix and match songs and pluck things from different artists.  I like the format.

It’s hard, in those instances, to tell whether you’re being sentimental and a luddite or whether there’s some deeper truth to your opinion or whether that distinction matters at all.

Anyway, I’m working on a record.  And maybe I won’t in the future.  And maybe it’s just whale blubber.  I can dig that.  But my next record is going to be good nonetheless.

It’s not necessarily a bad thing, I suppose, because poverty is perhaps slightly the wrong descriptor.

What the industry wants is what any industry wants: for the people searching for success in a specific field to be absolutely committed to it.  And that commitment means that you have to be willing to get on the road and tour and play to empty coffee houses and relentlessly promote yourself and scrounge and look for any opportunity to flog your wares and your persona.  And the practical implication of requiring that dedication is that the industry and the music press are encouraging a reckless and impractical notion of artistry that would impair any reasonable person’s ability to save for their future, to develop other types of skills they might sell into a growing market (as opposed to the music industry which is shrinking), and to put themselves in some kind of position where, if things don’t work out, they have something against which to fall back upon.

George Clooney has a great line where, when his father encouraged him to develop a fall-back skill, he said, “Pop, if I have something to fall back on, I’ll fall back.”

And, of course, this is written from someone that’s coming at it from the other perspective.  That is, I have a fall-back career.  And I like it.  And I am not interested in throwing everything away for music.  Or for art.  Whether that makes me a less perfect artist, or whether that means the art I create is not “great” or whether I haven’t met another person’s definition, or whether it’s all a manifestation of my own insecurity, who can say.

And I understand that for a management company or a booking agency or for any kind of capital to be invested, you want to know that your investment is fully focused on achieving the goals that are set forth.  So having a starving artist that absolutely must make it or they can’t pay their rent.  That’s probably the right motivation and the right incentive for someone making an investment.

But, based on personal experience, I find that I don’t do so well with desperation.  And that kind of tension and anxiety isn’t the most productive or motivating emotion against which I found energy relative to the dozens of other motivating energies and emotions that comprise my psyche.

At any rate, it’s something I think about on occasion.  Touring is not profitable.  I don’t care who says that it is.  It’s not.  For 90% of bands, it’s simply not profitable.  Also, please, please, please.  Please.  Please.  Please do not give me any bullshit or try to sell me a line that, (delivered in some kind of smug, sophisticated, I-read-this-in-an-article-recently tone of voice) “selling merch is where people make all their money on the road.”  Because they don’t.  Big and medium bands make money selling merch when people know who they are.  Small bands end up selling nothing night after night.

But the best way to get people to know who you are is not to tour but to use the Internet and your website and social media to build a fanbase.  But you have a much greater chance of getting good press and getting even bigger exposure if you tour.  Not for the act of touring.  And not for the people that you meet on the road.  But because the music press and the establishment will see your road-dog nature as evidence that you’re committed to your craft and that you’re willing to make sacrifices and that will make them more amenable to giving you a break in some other way.  Which again, basically, means that you have to show you’re willing to be poor and desperate in order to get a break.

And the problem is that the industry has become smaller, and there’s even less money floating around than there used to be, and, as a result, that desperation is even more desperate, more reckless and more full of fear and angst.

Me and Chris Cassidy did a photo shoot this weekend in Brooklyn.  We did one a year ago for the Pain record and someone said I looked like a European DJ in them.  These ones felt a distance better to me.  A bit more playful and relaxed.  This shot might be the cover of Singer/Songwriter, the new thing I’m working on with Nancy Hess.

First we started off in Cass’s building on Billyburg which has a number of great angles, shots, and pieces of architecture.  It’s a historic building that houses a lot of artists and filmmakers.

Then we walked over to this Hasidic supermarket where I strolled the aisles and caught the ire and attention of a few of the shoppers.

Then on to a deli because I wanted a shot of me sipping a soda in front of a classic New York bodega.  Then on to lunch at Diner next to Marlow and Sons.  We had a good time and were rapping most of the time and then sneaking pics every once in awhile.  Good stuff.

So Matt and I have been getting together in Matt’s apartment and studio in Williamsburg over the last month.  It’s been one of the best musical experiences of my life.

I am not a patient man.  I like the bold and decisive action.  And the ability to move quickly and to capture small little moments of musical magic and not get bored with something but simply clap your hands and say, “Next!” very loudly.  That is a wonderful thing.

Each night we spend about 3 hours and, up to this week, we’d been knocking out about 3 songs each night or a song an hour.  This week we only got to two but they both sound great.  One song called “When You Want To” and another song called “Arkansas” although I honestly don’t think I’ve ever been to Arkansas.

Matt has a baby grand piano in his apartment and a full Pro-Tools recording setup with some very nice mics.  He also has a great keyboard and he also has his natural musical ability.  He’s such a natural musical talent and so melodic that he can hear something once and then add something beautiful and insightful to the moment that elevates the song.

The way it works is that I bring in the song.  We do not play to a click.  No clicks allowed.  We’re not going to spend 30 minutes debating 142 vs 146 BPM.  I just play the tune on the acoustic and sing along and improvise most of the lyrics.  So some of the lyrics are trite and cliche and then some gems pop up every once in awhile.  Then Matt puts down a bass line on his keyboard.  Then does a piano track or two.

Then, for every song, we tend to tinker with a few select components.  For one song, maybe it’s a weird delay on a finger-picked guitar.  For another, a series of backing vocals with some odd harmonies.  For another, a weird syncopated handclap.  For another, a beautiful little riff on the glockenspiel in time with my vocal melody.  Little bits and pieces of beauty that are scattered throughout these songs.

We don’t spend a lot of time debating an idea.  I have some specific fragments that I’ve heard in my head for awhile.  And I get those down.  And then Matt has ideas and he adds those as well.  And then we tweak a few things and on to the next.

And because he’s a great engineer, he’s kind of mastering as he goes.  So at the end of any three or four hour session, I take home a disc that has all the tunes we’ve done and I can play it on my boombox in my tiny little apartment and smile to myself, maybe as I fall asleep or maybe as I wake up and before I shower and put on my clothes and head off to work.

So far we’ve done 8 songs.  It’s really so very fun.  It’s not labored.  It’s not studied.  There are flaws.  It’s so terribly human and inspired and there’s no pressure and these songs have these little things in them that I find myself waiting for and then wishing they’d go on forever.  Matt did this harpsichord thing that sounds a little like Bach in the outro of this song I’m calling “Purple Places” and it swells up with the strings and becomes this transcendent little moment that makes me think of Van the Man.

I hate waiting around.  I hate having to weight days and months and years before the thing that’s been on my mind is finally ready to be delivered to the world.  And knowing that there’s a way to make music, even if they’re “demos”, a way to make music that can feel as thrilling as a live performance but has at least some of the wizardry and care of a recorded work.  Knowing that and participating in that act of creation.  That is why we do what we do.  For that moment.  That little thrill you feel when the harpsichord comes in.  And how did he think to do that?  Because that sounds fucking great.

Perhaps the hardest part, especially for more senior people that are used to being in charge of something, is figuring out how to take what looks like a nice plan and make it something real.  Something real typically means finding someone willing to pay for something and presenting whatever it is that you do in such a way that they exchange money for it.  That’s actually really really hard.  Even for smart people.

And the question that I wonder aloud sometimes is whether that process should feel harder or easier as you go along.  If you’re growing and doing better, how should your day-to-day feel?  Because there are always challenges and always new things to do.

I suppose that, if you’re successful, replicating the same thing, making that same sale over time, should feel easier.  Hopefully, you’re getting better at it and you’re understanding what people want and are willing to pay for and how what you’re selling is different from what other people are selling.  And as you learn and adjust that core process becomes easier.

But then other people see that it’s easy and they start crowding into your market and then you have to stay on your toes and continue to innovate and continue to tinker with whatever it is that you’re selling so that it evolves and becomes different.  And that makes it hard or challenging again.

So, as I think about it or write about it, it seems maybe it’s the wrong question.  Since anything that works is bound to get harder as you’re forced to innovate.  And maybe the question is whether the work is interesting and challenging and whether it feels hard or easy depending on how engaged you are in the process and how good the team is with whom you’re working on the problem.

Still, in the back of my mind, I guess my intuition is that things should feel easier as you get better at them.  And that if they’re feeling harder.  If the core stuff that you’re doing feels like more of a drag, feels more taxing, spiritually or intellectually, that should be something to think about and to consider and upon which you perhaps should give some pause.

It’s a 7 minute aggressive dance song.  It’s about escapism and fantasy and about romanticizing delinquincy and all these fables we tell ourselves about running away from our problems and how everything will be good if we can just and, of course, as Gus McCrae says in Lonesome Dove, “life in San Francisco is still just life”.

So this is a somewhat new stylistic direction from the last officially recorded and released thing we did which was the debut record produced by Paul Brill and in a genre that I call “landscape pop” which is in the vein of folk-rock.  This is pretty much straight-ahead electronic dance music with the points of emphasis and differentiation being my voice and my singing and a little bit of acoustic guitar.  But the whole thing is pretty aggressive and dark and messed up.

Part of the experiment is that I am trying to resist the temptation to send the songs around to a bunch of people before it’s done.  That’s what I usually do.  I start floating rough mixes to people and it’s really just insecurity.  It’s me needing/wanting to hear back “Wow this is great!”.  For this thing, I don’t want anyone to hear the songs until they’re completely finished.  Until they’re ready to start hitting the blogs and getting pushed by Team Clermont (assuming they want to work on the project) and until the thing is completely done.  Until then, I don’t want people to hear a lick.

Why? I guess because I’d like to see what happens if me and Nancy just completely trust our own judgement and intuition and proceed apace and continue to work and tinker on it until the two of us feel it’s finally and completely done.

But the flipside of that is that insecurity inside of me begins speaking with a somewhat louder and more persistent voice.  The outside voice.  It says, “What if this thing is terrible?” and, “What if nobody likes it?” and “What if people just think it’s bad dance music and not anything particularly interesting?”  Those are some loud voices.  But part of this whole endeavor is to see if I can shut out those voices and just relax and think and use my own judgement and Nancy’s and if we can build something beautiful that we love without needing feedback or reassurance from anyone else.

Again, the drawback is that there is a potential that we could put in so much time into this thing and so much effort and then release it out into the world and hear nothing back or hear negative things back or feel like we failed in some way.  And, you know, you can feel the same way about anything, I suppose.  But, again, this is slightly and subtly different.

Should be interesting.

But, given Hamilton’s wide-ranging views and interests, and given the necessity of developing things like customs offices and the importance of tariffs and taxes to government revenue and thus to the overall functioning of the government, Hamilton’s reach extended well beyond what you might define as simple the stated responsibilities of Treasury.

Although many people viewed Washington as Hamilton’s tool, the truth was that the General exercised a calming and moderating influence on Hamilton and further exercised independent judgement when and where it counted.  The net result was that together Hamilton and Washington were an incredibly effective team.  Washington’s executive air and his wisdom quelled the more aggressive Hamiltonian tendencies that were to manifest themselves later.

Without Washington’s influence, both practically, because Washington retired to Mount Vernon, and explicitly, because Washington had left government and later passed away, Hamilton no longer had the check on his sometimes reckless behavior and his lapses in judgement.  It was without consulting Washington that he decided to publish his pamphlet providing lurid details on his affair with Maria Reynolds, a decision that undid Hamilton, showed incredibly poor judgement and undermined his influence in the government.  Other examples included various decisions to back candidates that ultimately didn’t prevail and to attempt to undermine Adams in his bid for the Presidency, a decision that ultimately further sank Hamilton’s influence over the years.

That’s a lot of prologue for a simple lesson.  A powerful partnership is an incredible thing. So often people are so much more effective and influential when they’re paired with some kind of balancing influence, someone that takes their baser tendencies and channels them in the right direction.  And you see the power of that partnership and the power of that union most notably in its absence.  When one member of the partnership is removed, you start to notice all the tendencies that had previously been clouded.

I remember this lesson from when I was reading “Disney War”.  When Frank Wells unexpectedly passed away, Eisner, as CEO of Disney, became much less effective.  Another lesson (this is how my mind works) and a famous one.  After the South’s greatest victory at Chancellorsville, Stonewall Jackson was killed by a Confederate sentry, by accident.  Without Jackson, Lee became much less effective.  Jackson had an intuition and a sympathy with Lee and could take what might be passive direction and actualize it with vigor and enthusiasm.

One last example near and dear to my heart and probably controversial from a music perspective.  I’d posit that the Bennett/Tweedy partnership from the last part of AM through Yankee Hotel Foxtrot would be yet another example.  People may disagree, but I think the quality, consistency and imagination of Wilco’s output has declined pretty measurably since Jay’s departure and his sad and untimely death.  Things seemed tighter, more melodic, more inspired with his contributions.  Even though those contributions seemed to create a tension within the band.

Successful enterprises need two things it seems.  They need either a supernatural executive with a singular vision (maybe someone like Steve Jobs or Jeff Bezos) or they need a powerful union.  Note that I’m not specifically saying they need a powerful team.  I believe in teams, under the guise of structured collaboration (that is to say with a boss) but I think a powerful partnership may, in fact, presuppose the necessity for a great team.

And you notice the import of that partnership, again, when one member of the partnership disappears or goes away.  Then, all of the tendencies of the remaining person are accentuated and highlighted.

Final note.  In the midst of the partnership, your optics may be off, or you may fall into some kind of hero trap, and you may even assume that one member of the partnership isn’t fully contributing, isn’t actually up-to-snuff, can’t get the job done, is the other’s tool or pawn, etc.  The partnership may not always appear fully functional.  Or equal.

But having a sane conservative voice check the passions of a reckless genius is still an example of a powerful and functioning partnership.  Washington may not have developed the same level of ideas that Hamilton undertook in his brief time on this planet, but his judgement and wisdom indisputably made Hamilton a more powerful figure.  And, in retrospect, it seems that Hamilton functioned better as the genius #2 then when he was adrift in his own world as the captain of his own ship.

And that gets back to the point of the three spheres, it’s important to know, or try to know, what role you play in that partnership.  To know, for example, if you’re meant to be a CEO or a COO and then be cool with that distinction.  Because, like you see in all these bands that break up, maybe you actually need that tension or that counterforce to be effective.  Maybe you’re not a Beck or a James Murphy.  Maybe you’re a George Harrison or a Jay Bennett.

So those three spheres are

1. Your interests
2. Your skills or talents and
3. The market

All three of those need to be in harmony to achieve true professional success.  And the point that was made was that too many people focused on only the first two and ignored the third.  I’ve written previously that perhaps the most fundamentally strategic choice to make is your market.  And that the rest is largely tactics.   So I think there’s a lot of merit to the notion that optimizing not just for what you like and what you’re good at but, to put it crassly, what pays, is a good idea.

Many people have great little artisan ideas about one thing or the other.  Maybe it’s making candles or something.  But the point is that even if you’re smart and good at doing stuff and you’re really interested in candle making, that doesn’t necessarily mean that the candle making industry is something that will lend itself to high levels of Return on Investment.

Maybe you can see where I’m going with this.  Much of the music industry is shrinking (from a revenue perspective).  If the market is shrinking.  If less money is being spent.  That’s important.  That’s a decisive consideration in things like if you want to start a new tech-focused music company.

Not saying it’s impossible.  Just saying that shrinking markets lend themselves to consolidation and to one or two dominant players.  If an ad-supported freemium subscription model is the format through which people will consume music in the future it’s perhaps unlikely that there are going to be more than one or two companies that survive.

And the real question is whether the money that’s added up is more than or equal to all the money that used to be added up for people paying for CDs and albums and going to concerts.  My guess is that it’s not nearly as much (but I could be wrong).  So if that’s the case, again, even if you’re really smart and talented and even if you’re really interested in the music industry, it’s worth a moment of pause if you’re thinking about working in it.

I used to write columns for the Cavalier Daily in college and I remember reading Shelby Foote’s The Civil War and wanting to write about the Battle of Chancellorsville.  My editors were opposed to it mainly because they felt it was jumping the shark a little bit and because there wasn’t really an opinion behind the column besides the fact that Hooker lost his nerve and it was really an incredible upset on Jackson’s part.  Writing about Alexander Hamilton now has that same feeling.  What’s the point?  I don’t know.  But I find the guy fascinating.  I had a vaguely negative impression of him based on my recollection of high school and the way he came across in the John Adams mini-series on HBO.  Clearly, I’m not an academic on the Founding Fathers.

At any rate, I just finished Ron Chernow’s wonderful biography on this incredible figure in American history and I feel compelled to jot down some things that I found interesting, as is my wont and my luxury.  There are a bunch of historical ideas that hadn’t formed in my mind and then two or three broader life/business/professional themes that I took from his life as well.

If you’re not familiar with Hamilton, I encourage you to read this book.  It presents a fascinating portrait of a complicated man and, importantly for me, it presents a radically different portrait of some figures that I’d only viewed positively in the past, namely Thomas Jefferson, who I know view as an important but necessary evil in our history.  That’s only as of right now but still.  Based on Chernow’s portrayal, he is not the man that has been canonized at my alma mater, The University of Virginia.

Some specific observations about Mr. Jefferson below:

Where I come from, Mr. Jefferson is a saint.  I’d always thought of him as the man that wrote the Declaration of Independence.  I admired his deism, given my own distrust of organized religion.  I loved the affectations he had around his university where the campus is The Grounds, underclassmen are referred to by year rather than by titles of seniority, etc.

But, the picture that emerges of him when viewed from both Hamilton’s point-of-view and from the facts of history render a wholly different portrait.

He was a hypocrite. There’s no two ways about it.  In so many different facets of his life, he advocated a certain set of positions and then did not live by that same code in his personal dealings.  He portrayed himself as a humble citizen, the South as a group of simple agrarians.  His Jeffersonian Republicans constantly felt that the Hamilton’s Federalist party were crass, merchant-oriented, imperialists intent on reestablishing a British monarchy while the innocent farmers of the South merely desired a freedom from tyranny and the oppression of a large central government.

Except for the fact that these simple citizen-farmers bought, sold and depended on their ownership of other human beings to drive their economy.  The fact of slavery is simply irreconcilable with the language of the Declaration of Independence and the further fact that Jeffersonians were able to so successfully portray Hamilton as money-hungry imperialists while they wielded the true scepter of despotism over so many is the basest irony and hypocrisy.

But it goes deeper than slavery.  It’s really about class.  Jefferson didn’t like the nouveau riche of the North and didn’t respect that Hamilton didn’t have the proper background.  Again, for all their protestations about simple agrarian living, it really seems an argument about a class and caste system strikingly similar to the English one they pretended to disavow.

And he was wrong about his notion of America.  Hamilton was right.  Hamilton embedded the seeds of our financial markets, from scratch, with more vision and foresight than anyone else possessed at the time and his view of America as a country of merchants and, essentially, entrepreneurs was ultimately the view that prevailed.  And for the best.  It lifted millions out of poverty, gave opportunities to small businesses, and laid the foundation for the economic powerhouse that America ultimately became.  He believed in a national army when many didn’t.  That same national army that saved the Western World almost 200 years later in Europe.  Jefferson, Adams, Madison: These people didn’t even believe in banks!  They didn’t understand the power that credit and liquidity brought to a financial system or how a diverse economy was set free by a strong system of central credit and, ultimately, trust.  They thought commerce was gauche and ungentlemanly.  Truly, their vision of our country was of a landed gentry, all under the auspices of simple citizens, that depended for their economic foundation and liberty on other human beings.  That they owned, bought and sold.

Hamilton was an abolitionist.

And then there’s the fact that, as Jefferson condemned what he thought where the Tory loyalists in New York, and while he supported the “citizen uprising” during the French Revolution, he lived in mansions, had legions of attendants including, of course, Sally Hemings, and accumulated vast stores of possessions.  When he became Secretary of State, under Washington, he had 26 crates of French furniture, china, porcelain and other assorted odds and ends shipped back to New York.

Just a simple citizen farmer, huh?

While the party system was not really developed (Jefferson and Hamilton represent the start of the two party system in the States actually), Jefferson was part of Washington’s cabinet and colleagues with Hamilton yet constantly worked to undermine both of them, going as far as funding anti-administration newspapers using federal monies (!).  All  while he was supposed to be serving President Washington.  He specifically provided different messages than the official White House position to the French government under both Washington and Adams.

Finally, he was rather callous and bloodthirsty yet showed no valor or bravery in battle.  As has been commonly quoted, he remarked that “the tree of liberty must be refreshed from time to time with the blood of patriots and tyrants.”   He was rather nonchalant about the French Revolution despite the agony, tyranny, violence and pointless bloodshed that characterized those years in France.  He sounded like George Bush talking about the early years of Iraq.  Meanwhile Hamilton warned that tyrants often hide under the guise of “the common man” until they’re able to seize power and reveal themselves as despots.  He accurately predicted Napoleon’s rise in France and, of course, years later, the likes of people like Stalin, Mao, Pol Pot and others.  Despite his more measured approach to the French Revolution, Hamilton had numerous instances of courage and bravery under fire.  Jefferson’s most famous moment on the fields of battle when he abandoned Richmond to the British and fled to the hills of Charlottesville.

Last point.  When Hamilton was killed by Aaron Burr, Jefferson remarked in a letter that he was “Colonel Hamilton” which is basically just him being an assh*le since Hamilton had been promoted to General when we raised an army under Adams at the possibility of war with France (the so called Quasi-War).

There are a lot of counters.  It was probably helpful to have the Republicans focus on smaller government and diminishing the power of the federal government and the executive as a counterweight to Hamilton’s notion of a strong executive.  And slavery was bigger than just Jefferson.  And this is all from one person’s POV, namely his arch-nemesis and his lifelong political rival.  But, nevertheless, the portrait that’s been painted to me of Jefferson via our educational institutions and culture had none of this nuance and none of this balance.  Jefferson and Adams got to write the history books because Hamilton died so early but there needs to be a more serious reevaluation of Jefferson as a man.