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What drives folks like Sanjeev?


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Let us admit it - Sanjeev is a self-made multi-millionaire that owns multiple businesses. He can easily retire smoking cigars in Florida but continues to work hard. He is a bachelor but is very driven to succeed - not unlike a fella from India called Modi.

 

What drives folks like him or what drives you that are financially independent? I think folks like UccmAl and Ericopoly are also in this budget.

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I have a way to get a good answer.  Hey Sanjeev, what drives you?  :)

 

I think both RB and Mephistopheles answers are good and true of me.  I'll also give my own answer.

 

For some people, doing one thing really well and making it as big as possible is fun.  So, I'd put people like Watsa, Buffett, Ellison etc in this camp.  They do what they do because it's fun, and what else would they do?

 

I'm more of a generalist though.  I've started multiple tech businesses and become a multimillionaire, but I'm not so wealthy that I don't need to think about what I buy. I still budget.  However, instead of continuing to become ever wealthier, I've decided to do what I want instead.  Essentially, the decision is, "would I be happier trying to get twice as much money or doing other stuff?"

 

Since I'm a generalist, my answer is "other stuff".  I have a bunch of ideas that I want to explore--new businesses, math problems, blogging, investing stuff, and programming challenges.  Now that I'm financially independent, I'm exploring those ideas.

 

Mostly recently, I've been writing novels.  Writing is a terrible way to make money. I'd never have it as my primary focus if I weren't financial independent. But for some people it's fun, and I'm one of those people.  So I'm publishing novels--my first one was The Battlefield Abductions.  Eventually, I'll move on to something else.

 

As an aside, one thing that the question seems to imply is that retirement is more fun than other things.  But, I don't think that's actually the case.  Really, doing nothing is boring. Seeking nothing but entertainment (video games, movies, beaches, theme parks, drugs) is equally boring. Creating and exploring interesting things is far more fun. 

 

So, I think the answer is usually that people will do whatever they enjoy. So, people who enjoy creating massive businesses will do that.  Other people, like me, will explore ideas.

 

For some of my other thoughts on financial independence, I did an AMA on reddit about the topic.

 

 

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As an aside, one thing that the question seems to imply is that retirement is more fun than other things.  But, I don't think that's actually the case.  Really, doing nothing is boring. Seeking nothing but entertainment (video games, movies, beaches, theme parks, drugs) is equally boring. Creating and exploring interesting things is far more fun.

 

This.

 

There are lots of people who have to work to put food on the table.  But if you're beyond that stage, take 4 weeks off this summer, sit on a beach, and do nothing.  I find that it takes about 2 weeks for my friends with regular jobs to actually relax fully.  But most of them will start to go squirrely by week 4 with boredom.  It takes me about 2 weeks to reach this stage. 

 

Those who are able should find something they like and do, and do it, after getting their "FU" money.  Bonus points if it also earns money, makes the world a better place, etc.

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Let us admit it - Sanjeev is a self-made multi-millionaire that owns multiple businesses. He can easily retire smoking cigars in Florida but continues to work hard. He is a bachelor but is very driven to succeed - not unlike a fella from India called Modi.

 

What drives folks like him or what drives you that are financially independent? I think folks like UccmAl and Ericopoly are also in this budget.

 

Not a multi-millionaire like Uccmal or Ericopoly, but I am a millionaire...had to spend a good chunk of my money in the early years to survive, so that I could finally build CMC, MPIC and PDH...although if you include my house then I am.

 

I don't know what drives me.  It was like the first sunny Saturday and Sunday in Vancouver in four months and I was/am sitting in the office both days.  No one is here in the entire building other than me!  I'm finishing off the PDH annual letter, and I have to finish off the MPIC annual letters in the next day or two. 

 

All i know is that I have a lot fun coming to work.  Most people don't like going to work, but do so because they need the money or the money is really good.  I don't spend alot of money and if I could afford to do what I do for free, I would do it.

 

Funny thing is, the more you are in this world working at what you love, the more you attract like-minded people who are doing the same...be it as a value-hedge fund manager or some other venture/occupation. 

 

I just love business.  I love how business works...how it affects our daily lives...how people feel about their business.  I like owning or building something that people like or can use.  The treasure hunt aspect of being a value fund manager is all well and good, but you aren't building anything...you're shuffling money from one idea to another.  But when you also operate a business or at least help guide its direction, and then how that fits into the world and people's lives...it's very intriguing!

 

Lastly, I always hated working for others where they disrespect you or left you feeling undervalued or unappreciated.  I didn't want to ever work for anyone else again, and I wanted to do what I wanted exactly when I wanted.  I don't get in the office until 10-10:30am, but I don't leave until 7:30-8pm.  I rarely leave my desk for lunch, and generally work for the entire time I'm in the office.

 

Today I get to do exactly that!  I've met Warren Buffett a few times...I've met Wayne Gretzky a couple of times...I'm friends with the exact hedge fund managers that I looked up to and wanted to copy 12 years ago...Prem Watsa is the biggest investor in my fund...I run a public company and get to acquire and start businesses...I work when I want, I sleep when I want, I eat when I want and both me and my family are very comfortable.  You would think I would work less in that case, but I actually work more...it's just so much fun to me!  Cheers!

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I have a way to get a good answer.  Hey Sanjeev, what drives you?  :)

 

I think both RB and Mephistopheles answers are good and true of me.  I'll also give my own answer.

 

For some people, doing one thing really well and making it as big as possible is fun.  So, I'd put people like Watsa, Buffett, Ellison etc in this camp.  They do what they do because it's fun, and what else would they do?

 

I'm more of a generalist though.  I've started multiple tech businesses and become a multimillionaire, but I'm not so wealthy that I don't need to think about what I buy. I still budget.  However, instead of continuing to become ever wealthier, I've decided to do what I want instead.  Essentially, the decision is, "would I be happier trying to get twice as much money or doing other stuff?"

 

Since I'm a generalist, my answer is "other stuff".  I have a bunch of ideas that I want to explore--new businesses, math problems, blogging, investing stuff, and programming challenges.  Now that I'm financially independent, I'm exploring those ideas.

 

Mostly recently, I've been writing novels.  Writing is a terrible way to make money. I'd never have it as my primary focus if I weren't financial independent. But for some people it's fun, and I'm one of those people.  So I'm publishing novels--my first one was The Battlefield Abductions.  Eventually, I'll move on to something else.

 

As an aside, one thing that the question seems to imply is that retirement is more fun than other things.  But, I don't think that's actually the case.  Really, doing nothing is boring. Seeking nothing but entertainment (video games, movies, beaches, theme parks, drugs) is equally boring. Creating and exploring interesting things is far more fun. 

 

So, I think the answer is usually that people will do whatever they enjoy. So, people who enjoy creating massive businesses will do that.  Other people, like me, will explore ideas.

 

For some of my other thoughts on financial independence, I did an AMA on reddit about the topic.

 

Pretty cool stuff and great reddit discussion. Always find this kind of stuff fascinating. How one attains their freedom. The pursuit of money is often falsely associated with people who are driven. Personally I think the freedom from hard work is the primary driver and accumulating wealth is generally just the bi-product. David Siegel from time to time has had somewhat interesting commentary on the ease with which hard work alone can propel one to great heights simply because this type of work ethic itself has become a scarce commodity. Especially when you are young. Wouldn't necessarily call him a role model but I always find it neat how you hear the same type of things. "In my mid twenties I was at my office working on Friday at 10 pm while my friends were out getting drunk and chasing tail at the bars" was one of his better lines. It is quite true. The earlier you can stand compounding the better. Not only can you compound wealth but experience too. Both become immensely valuable over time.

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I have a way to get a good answer.  Hey Sanjeev, what drives you?  :)

 

I think both RB and Mephistopheles answers are good and true of me.  I'll also give my own answer.

 

For some people, doing one thing really well and making it as big as possible is fun.  So, I'd put people like Watsa, Buffett, Ellison etc in this camp.  They do what they do because it's fun, and what else would they do?

 

I'm more of a generalist though.  I've started multiple tech businesses and become a multimillionaire, but I'm not so wealthy that I don't need to think about what I buy. I still budget.  However, instead of continuing to become ever wealthier, I've decided to do what I want instead.  Essentially, the decision is, "would I be happier trying to get twice as much money or doing other stuff?"

 

Since I'm a generalist, my answer is "other stuff".  I have a bunch of ideas that I want to explore--new businesses, math problems, blogging, investing stuff, and programming challenges.  Now that I'm financially independent, I'm exploring those ideas.

 

Mostly recently, I've been writing novels.  Writing is a terrible way to make money. I'd never have it as my primary focus if I weren't financial independent. But for some people it's fun, and I'm one of those people.  So I'm publishing novels--my first one was The Battlefield Abductions.  Eventually, I'll move on to something else.

 

As an aside, one thing that the question seems to imply is that retirement is more fun than other things.  But, I don't think that's actually the case.  Really, doing nothing is boring. Seeking nothing but entertainment (video games, movies, beaches, theme parks, drugs) is equally boring. Creating and exploring interesting things is far more fun. 

 

So, I think the answer is usually that people will do whatever they enjoy. So, people who enjoy creating massive businesses will do that.  Other people, like me, will explore ideas.

 

For some of my other thoughts on financial independence, I did an AMA on reddit about the topic.

 

Pretty cool stuff and great reddit discussion. Always find this kind of stuff fascinating. How one attains their freedom. The pursuit of money is often falsely associated with people who are driven. Personally I think the freedom from hard work is the primary driver and accumulating wealth is generally just the bi-product. David Siegel from time to time has had somewhat interesting commentary on the ease with which hard work alone can propel one to great heights simply because this type of work ethic itself has become a scarce commodity. Especially when you are young. Wouldn't necessarily call him a role model but I always find it neat how you hear the same type of things. "In my mid twenties I was at my office working on Friday at 10 pm while my friends were out getting drunk and chasing tail at the bars" was one of his better lines. It is quite true. The earlier you can stand compounding the better. Not only can you compound wealth but experience too. Both become immensely valuable over time.

 

+1

 

Hard work does not mean working 10 -12 hours; Even 2-3 hours of work you don't enjoy is much much harder than "working" long hours on what you enjoy.  If it results in $$ that's even better. For most of this community, the hard (not) work is reading!

 

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uccmal: Not a multimillionaire.  minimillionaire is more like it. 

 

I like the challenge.  Right now it sucks though.  There are limited (No) good values.  To me this indicates a market top.  Its now a patience game waiting for the next major crash.  It was like this in 2007/2008.  I had less experience then and was going down the quality curve.  Not this time.  I'm judiciously raising cash.  I am sitting on overvalued real estate. 

 

Sooner or later things are going to blow up. 

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As an aside, one thing that the question seems to imply is that retirement is more fun than other things.  But, I don't think that's actually the case.  Really, doing nothing is boring. Seeking nothing but entertainment (video games, movies, beaches, theme parks, drugs) is equally boring. Creating and exploring interesting things is far more fun.

 

This.

 

There are lots of people who have to work to put food on the table.  But if you're beyond that stage, take 4 weeks off this summer, sit on a beach, and do nothing.  I find that it takes about 2 weeks for my friends with regular jobs to actually relax fully.  But most of them will start to go squirrely by week 4 with boredom.  It takes me about 2 weeks to reach this stage. 

 

Those who are able should find something they like and do, and do it, after getting their "FU" money.  Bonus points if it also earns money, makes the world a better place, etc.

 

When I have gone south to all inclusive resorts, I am pretty much ready to come home by day 5.  I get bored.  I get tired of asking for coffee all day, and being served hand and foot.  Its nice not to have to cook and clean up after the kids, but wears thin after a few days. 

 

My favourite vacations involve backpacking, or "in motion" trips where we stay for a few days in one place, explore, move on, explore etc.  The notion of a caribbean cruise makes me nauseous..and not from seasickness. 

 

One thing I would really like to do when/if real estate finally crashes is to buy a fixer upper, and fix 'er up. 

 

I practice my guitar at least an hour per day, and play in a non-pro band that practices once per week.  I will probably pursue this more as time goes, but dont expect to ever make a cent off of it. 

 

Oh, and course there are the kids.  I do far more with them, and for them, than my Dad, or his Dad, ever did.  My birth family was very typical for the 70s with Dad bringing home the bacon, Mom raising us. My own family is not like that at all.  Our one concession to luxury is a great lady who cleans the house throughly every two weeks, saving us from a divorce.  Otherwise, we buy used cars, and drive them into the ground. I do nearly all home repairs myself with assistance from you tube. 

 

I read alot on a multitude of topics.  Very much a generalist.  Some of it may have relevance to investing, most not. 

 

Having FU money changes things in weird and subtle ways.  You hear a radio station contest with a $1000 prize and think why bother.  The local hospital has a lottery with a 50,000 dollar prize - big deal for some but doesn't really move the needle anymore... not that I would turn it away.  :-).  And I buy anything I want when I want to.  Given my wants are not much I am unlikely to blow the budget. 

 

BTW: Interested to hear others stories: Richard. 

 

If I ever go back to a job it will be more like Sanjeev, and Norm's situations.  It would have to be a labour of love, not exclusively for the money. 

 

 

 

 

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BTW: Interested to hear others stories: Richard. 

 

Sure.  I can talk about one of my failed ideas almost fits the theme of this board, auto-trading.

 

As you probably know, Interactive Brokers has an Application Programmer's Interface (API).  For those who aren't geeks, this means that it's easy to write your own program that can access the functionality of Interactive Brokers' trading application.  Your program can, among other things, get real-time quotes and trade shares and options.

 

Of course, this presents an almost irresistible temptation to create my own trading program, so that's what I did.

 

I decided to focus on trading the leveraged and unleveraged volatility ETF & ETNs (TVIX, VXX etc.)  My reasoning for selecting these guys was essentially that I needed stupidly high volatility to be profitable.  I wasn't sure how real-time my real-time quotes actually were, but they were certainly far less real-time than the pros.  Plus, I was going to be losing on the spread and the commission with every trade.  So, I needed big moves to actually profit, and there was almost nothing in the market that was as volatile as the volatility ETFs.  What's more, this was 2009 and 2010, so the volatility of volatility was still pretty high coming off the 2008 crash.

 

So, I coded an application that initially would simply get real-time quotes and dump them into a database.  I can't remember how long I did this for--probably only about nine months, nowhere near long enough to be confident of anything, but enough to be dangerous.  :)

 

Then, I created a simple day-trading trend following application.  Essentially, it would enter a trade when the ETF had gone a certain amount in a particular direction (long if the trend was up, short if the trend was down).  Then, it would close the position when the trend stopped, or at market close.  It probably averaged two positions per day.  According to the data, this seemed like a profitable strategy because these volatility EFTs would move slowly, then spasm dramatically in either direction.  If you could get the beginning of that spasm, you could be profitable.

 

I allowed my program to paper trade that for a while (another nice feature of Interactive Brokers), and it still seemed profitable.  And then I tried it with real money.

 

It mostly worked, for about six months.  My position sizing was about $30K, and after about six months I was up $20K.  However, there were some problems.  Despite the computer turning around the "real-time quotes" almost instantly, my trades frequently didn't happen at the exact bid/ask that was quoted, particularly in cases where the spasm was really big and fast (think a 10% move in 30 seconds).  Missing a big chunk of these spasms really hurt my returns.

 

The profitability numbers were pretty interesting. Missing the start of these spasms cost me 50% of my theoretical returns.  What's more, my theoretical returns were less than half of what they could be if I didn't have to worry about the spread (i.e. if instead I bought and sold at the mid-point of the bid/ask spread).  And commission were taking another chunk, like 20% of my theoretical profits.  In other words, the market maker was certainly making far more from my trading than me, and my broker was doing pretty well too.

 

It's also worthwhile noting that trading in shares was more profitable than trading in the options, simply because the options effectively had bigger spreads and the moves to make options profitable needed to be larger.  Thus, trading shares led to higher number of low-value wins, while option trading led to a lower number of high-value wins.  Both strategies were profitable, but for my algorithm, share trading beat options trading.

 

Then, as time passed and the market got farther away from 2008, volatility decreased, which also decreased the volatility of volatility.  This was quite bad for me, since my program relied on the volatility ETFs being volatile to make money.  My profits started to evaporate.  Luckily, I had programmed pretty charts, so I knew what was going on, so I shut it down when I only had a profit of $10K.

 

The final numbers were pretty funny.  With my trades of about $30K each, I'd turned over something like $4-5 Million  in shares, paid thousands of dollars in commissions, and ended up with a profit of $10K.  From a mathematical perspective, it's hard to even know if my $10K profit on $4M in trades would be statistically significant.  I suspect not.

 

It was a fun game.  Sitting around while my computer makes money for me has psychological appeal for me, despite the (reasonable) paranoia of something going wrong (i.e. my program or Interactive Brokers crashing when I'm short VIX right before a flash crash.  My program never crashed, but it was a valid concern nevertheless.)

 

So that's one story.  I might share others later.  I also have some stuff on my blog, though the political posts are likely too left-wing for your taste.  My blog doesn't have a theme beyond things that interest me.

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Did you use Java, C++ or Python?

 

IB offers an API so that implies it is web requests.  So the JAVA, C++, Python question might be moot because the bottleneck will always be the network.  Figuring you were wondering about speed/efficiency?  Network latency will always be several magnitudes slower than running local machine latency.  That is why those High Frequency traders have their data centers as close to the exchange as possible. 

 

 

 

 

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Did you use Java, C++ or Python?

 

IB offers an API so that implies it is web requests.  So the JAVA, C++, Python question might be moot because the bottleneck will always be the network.  Figuring you were wondering about speed/efficiency?  Network latency will always be several magnitudes slower than running local machine latency.  That is why those High Frequency traders have their data centers as close to the exchange as possible.

 

This kinda misses the point.  I think DooDiligence was asking what language the program was coding in.  Last I checked IB offers support for all of those and a few other languages.

 

Yet, network latency matters, but processing time also matters.  There's a magnitude of difference in trying to run analytics on a dataset with Python vs C# or Java.  When the datasets get large enough an interpreted language might not be fast enough to make a determination of what to do in enough time.

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I'd say anything you try at home with TWS that fails because your Python implementation is too slow is either a) horribly implemented or b) a pointless idea because your data feeds and order routing are way, way too slow anyway to compete in the speed game. Ideas you can automate with TWS are those for which the speed requirements are such that you could do the trades manually if you could sit super focused behind the computer all day. Anything faster you'd get utterly crushed.

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Did you use Java, C++ or Python?

 

C#.  As Joe says, I was assuming that the network latency is far greater than any in-machine slowness.  It would surprise me if that weren't the case, but that's just a rule of thumb from my background in distributed computing rather than actually having any evidence.

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Thanks odd, writ & Richard.

 

The latency issues you guys brought up hadn't occurred to me.

 

I'm on a path to becoming a full stack web dev & have been discussing web vs enterprise with AugustaBound (his preference is for enterprise.)

 

-----

 

Interesting discussion on interpreted vs compiled

 

http://stackoverflow.com/questions/3265357/compiled-vs-interpreted-languages

 

-----

 

Hey, speaking of latency, I just got Sling TV & noticed that if I'm watching CNBC on the big screen & iPad at the same time, the iPad broadcast lags the TV by 3 to 6 seconds (is there an arbitrage here?!?)  ::)

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Hey, speaking of latency, I just got Sling TV & noticed that if I'm watching CNBC on the big screen & iPad at the same time, the iPad broadcast lags the TV by 3 to 6 seconds (is there an arbitrage here?!?)  ::)

 

Let's collaborate on a programming assignment to figure this out.  ;D

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Thanks odd, writ & Richard.

 

The latency issues you guys brought up hadn't occurred to me.

 

I'm on a path to becoming a full stack web dev & have been discussing web vs enterprise with AugustaBound (his preference is for enterprise.)

 

-----

 

Interesting discussion on interpreted vs compiled

 

http://stackoverflow.com/questions/3265357/compiled-vs-interpreted-languages

 

-----

 

Hey, speaking of latency, I just got Sling TV & noticed that if I'm watching CNBC on the big screen & iPad at the same time, the iPad broadcast lags the TV by 3 to 6 seconds (is there an arbitrage here?!?)  ::)

 

Enterprise or what?  I guess the question is "are you interested in making money or just playing?" If it's just playing then forget enterprise.  If you want to make money learn enterprise level stuff.  The money is in B2B.

 

People hesitate to spend $2 on the App Store.  But a business will drop $100k without thinking.

 

I've done the full gamut, from PHP/ASP to Java, to JavaScript to C#, I originally learned C then C++.  We've moved our business to C# with an Angular front-end.  It's high performing and scalable.  C# is the best compiled language I've ever worked in.  Our data was too large for interpreted languages.  We had jobs that would grind away for 45m that are done in less than 1m in C#.

 

We have a typical data warehouse, star schema and all.  So data comes in and is then processed.  Jobs run over it, aggregate it, create derivatives etc then stick it into the star scheme.  The data is never updated, never.  Any updates are a new row with an audit record.  This means the UI is only reading, never writing or needing to wait for any processing.  Obviously user interactions are read/write, but the underlying data is essentially read only.  Any computing happens before the user sees it.  This provides a fast user experience and also gives us the ability to have a point in time DB.  A point in time DB is extremely valuable.

 

In terms of trading etc.  I've never built a trading robot.  We did some real time strategies with our Bloomberg app for a while.  It used their C# library to get real time market data and build strategies out of it.  I had built about 25 different strategies that refreshed near instantaneously with their API.  I tried to replicate the same thing with an interpreted language outside of the Bloomberg app and it was too slow.  It only took about 15s to render, but to a user it seemed like an eternity sitting there waiting. 

 

I'm not sure of Bloomberg's API is accessible via Python.  I know they support C#, Java, and C++.

 

If you want to build market strategies I'd pay up and buy access to the direct exchange feed.  I know Bloomberg offers this, you get the direct feed.  My guess is IB delays it, or sells the feed.  Better to buy direct.

 

But the key as everyone has mentioned is latency.  But that only matters if you're trying to execute instant trades and arbitrage little opportunities.  We had some strategies that didn't require instant execution.  You could execute as a human if you wanted.

 

Let me take a short trip down distributed memory lane.  Years ago I worked on the application the military generals used to coordinate battlefield movements in Iraq, it's called CPOF (it's public now, you can Google it.)  The challenge was the app was a real time story board that was constantly being updated from multiple locations around the country.  The locations were linked via satellite, but could have a delay of up to a few minutes.  This was problematic because troops could have been moved to location A and a different command post might not see the update for minutes.  This meant that an airstrike could be called on A that would look clear, but in reality troops were moved there during this delay.  To compensate there was an extremely complicated underlying system that ensured everything was sync'ed to avoid friendly fire issues, but also provide up to date perspectives.

 

It was an awesome project to work on, I believe it's still being developed and in use.  What's interesting about it is the underlying architecture was built by MayaViz with the intent on being used for trading and exchanges.  The finance business never took off, but the military application did.  Eventually MayaViz was bought out by General Dynamics.

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Great post odd!

 

I see web dev as accessible for someone who only understands markup (I know it's not code) & believe that learning javascript & then PHP MySql would be easier than jumping straight into C++ and all that (true or false?)

 

I figure if it turns out I can't code for squat, I can fall back on front end web dev (which I enjoy...)

 

If I can learn to code then yes, it would make sense to go where the big dollars are...

 

(we kind of got off topic - this is supposed to be about Sanjeev's drive)

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I think ERP/Enterprise has various levels too, some more difficult stuff on the backend and how to handle data and the potential easier stuff in the front end, hopefully making the user experience better. I think the latter requires  someone who puts himself into the shoes of an actual user and it appears to me (as a user of these systems, I don't know squat about programming) that those are lacking too. either that or companies don't want to pay up for the level of customization that is actually desired from a user perspective. It's probably a combination of both.

 

I have some buddies from my research group at the university who went to work for SAP many moons ago and make a very good living doing so.

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Great post odd!

 

I see web dev as accessible for someone who only understands markup (I know it's not code) & believe that learning javascript & then PHP MySql would be easier than jumping straight into C++ and all that (true or false?)

 

I figure if it turns out I can't code for squat, I can fall back on front end web dev (which I enjoy...)

 

If I can learn to code then yes, it would make sense to go where the big dollars are...

 

(we kind of got off topic - this is supposed to be about Sanjeev's drive)

 

I really don't know what the advice is now.  I learned to code in the 90s before the web was popular.  I learned C and C++ out of the gate.  But this was also a time when we had 10 hours of dial-up free internet access per month from AT&T and never even used half of it.

 

If I needed to hire someone right now (and I don't, but maybe will in 6mo-1yr) I'd hire a junior web dev first.  Someone who knew Angular and could handle C#.  Someone who could fix bugs and build features on existing code, but isn't doing greenfield development.

 

The web stuff is unfathomable for me.  But I've moved on from the web dev role, I do some of our systems/data work, but mostly marketing and sales.  I understand tech, can sell tech, but when it gets into the weeds I rely on my partner who is the tech person.

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I think the latter requires someone who puts himself into the shoes of an actual user and it appears to me (as a user of these systems, I don't know squat about programming) that those are lacking too.

 

Programmers in general are not good in thinking in terms of user experience. Depending on area/product/company there may or may not be a dedicated team that does the user experience (that includes UI, but not just UI). The team may be good/mediocre/bad. It may be supported by the rest of the company or just tolerated. Success of the product(s) may depend on that team or not at all. For most enterprise software my guess is that the user experience is not thought out much. But I don't have non-anecdotal data.

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