It's easy to get upset when your job or your company isn't doing well.  So much of our identity is tied to what we do for a living, yet it's so meaningless in the whole scheme of things.

If you're down about startup, worried about failing, watch this clip on Tony Robbins' show Breakthrough.  This former NBA player gets a stroke, gets kicked off his basketball team, and feels like he's lost a huge part of who he is.

"You are who you are as a man and your worth is not tied to what you do."

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I had a great interview at Stanford ETL with one of inDinero's angel investors, Steve Blank.  Giving that talk was among the more humbling experiences I've had as an entrepreneur, and it's amazing to see that it's been viewed over 15,000 times.

For a little back story, I've been watching ETL talks since I was 16 years old.  I remember going for the first time to watch Martin Eberhard talk about growing Tesla Motors, and I was blown away by how amazing the experience was.  "One day, I'd get invited to speak at ETL."  But that invitation came only a year and a half after starting inDinero, and I felt like it was premature.  The company was still in its infancy, we'd just gone through a bunch of unexpected problems, and there was no light at the end of the tunnel.  

Every past ETL speaker had accomplished something amazing -- with me being the exception.  Instead of pretending to meet that high standard, I thought it'd be more helpful to young entrepreneurs to be completely honest with my experiences, and to share how unforgiving the world of business might be.

Hope you can set aside the time to watch.  You can also download the mp3.  Big thanks to Steve Blank for giving me this opportunity.

-- jmah

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It's been a while since my last update.  Company is doing well right now, and I thought it'd be cool to share an interview I recently did with theDailyMuse:

http://www.thedailymuse.com/entrepreneurship/start-up-success-stories-jessica-mah-of-indinero/

More to come.

- jmah

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Over the past few months, I've picked up a fascination for politics and the history of our past Presidents.  It occurred to me that every single American President since my birth has been put under extraordinary criticism, and none has left with a pristine legacy.  Which means one of two things -- either that every President is the idiot that late night TV shows make them out to be, or that being President of the United States is an incredibly daunting and difficult task.  While it's more convenient to think the former, I've come to realize the contrary after reading through the memoirs of many of our past leaders.  

While in high school, I remember being among President George W. Bush greatest critics.  I'd gone so far as to purchase bumper stickers that read "Impeach Bush", and I would debate with my mom about how terrible of a leader he was.  I remember her responding, "if being President is so easy, why don't you try running the country yourself!"  Being the naive high school student I was, I actually believed I could.  My anger towards our then-President grew even more, and I read any liberal commentary and criticism I could get my hands on.  Fahrenheit 9/11 was a favorite, and I remember thinking that our President wanted to go to war only for selfish monetary reasons, and I didn't trust that he cared about saving lives.  But after spending 18 months on the job at inDinero, I've grown an appreciation for all well-intentioned leaders, regardless of what others might think of them.  And the person I now respect the most is ironically George W. Bush.

How could a left-leaning liberal go from being a Bush hater to being a compassionate supporter?  For all my life, I had been trapped in a political bubble, limited by the opinions of my peers who had listened to nothing but one opinion:  that of the super liberal democrat.  There was no chance that I'd hear the second perspective, because none of my classmates or teachers were willing to consider it.  But I grew to realize that it was actually the opposite perspective that mattered most.  I took it up as my personal responsibility to learn about every decision he made that I felt strongly against:  the invasion of Iraq, our use of torture on terrorist detainees, the Patriot Act, the "tax cuts for the rich", his policy on stem cell research, among other policies that I remain ambivalent about.  The point of my research was to seek the opposite perspective, and to be open to changing my political opinion should I find truth in this new perspective.  

I began by reading Dick Cheney's In My Time, followed by George Bush's recent released book called Decision Points.  After finishing both, I was blown away by the candidness of both of our former leaders.  I learned that both had considered the opinions of many of their advisors, and that they went through serious consideration before making any major decisions. I shocked myself by reversing my opinion on multiple policies he made that I felt strongly against.

To my own disbelief, I felt compassion for a former President who I had despised for over a decade. Through high school and college, I didn't know how to feel anything other than anger towards our then-President.  But from taking only a few evenings to read through the other side's perspective, all of that anger just magically vanished.  I came to understand that I didn't have to agree with Bush's opinions.  I didn't have to like his questionable leadership abilities, and I didn't have to like him as a person.  But as an educated citizen, I felt responsible to escape the liberal bubble that I had grown up in, and to always go out of my way to understand multiple perspectives before giving judgement.

The most difficult part through all of this has been talking with friends and former classmates about this.  "Why would you care to read what that idiot Bush thinks?"  I've since had to come to the rescue for Obama, who's now undergoing scrutiny for his inability to magically fix our economy.  Scrutinizing others is easy, but finding the courage to compliment them is far more difficult.  When people criticize our former leaders, I try to pass on the saying my mom left me with many years ago.  

If being President is so easy, why don't you try running the country yourself?

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Our friends at GiftRocket put together a very cool infographic on Paul Graham's "Startup Ideas We'd Like to Fund".  Back in 2008, he put together 30 problem spaces he thought startups should tackle.  

inDinero specifically attacks idea #21:

21. Finance software for individuals and small businesses. Intuit seems ripe for picking off. The difficulty is that they've got data connections with all the banks. That's hard for a small startup to match. But if you can start in a neighboring area and gradually expand into their territory, you could displace them.

I remember looking at this list in the winter of 2009, long before Andy and I had even considered applying to Y Combinator.  We already knew we were excited about this problem space, but seeing our idea on PG's list gave us extra validation that we were going after a problem that few had solved well.  But it is so vague and unspecific that it forces you to still think through the specifics of your idea, and which specific problems you care to solve.  

I remember putting together a bunch of finance-related ideas:  helping people get out of debt, helping people with their investments, replacing QuickBooks, and we came up with a list of reasons for why each idea was terrible.  And eventually settled on creating a financial dashboard for businesses.  

If you're looking for a business idea to work on, I'd start with a high-level problem space that you're passionate about, then narrow it down from there.

Created by GiftRocket gift cards

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I recently had a great chat with William Channer over at Dorm Room Tycoon, and we talked about everything from product development to improving funnel metrics.  He has also interviewed inDinero angel investors Steve Blank and Jude Gomila.

Here's the interview:  http://www.dormroomtycoon.com/jessica-mah-indinero-interview-steps-to-great-product-strategy-startup-interview/

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Over the past few weeks, I've come to notice that companies known for raising absurds amount of money are often founded by entrepreneurs who've succeeded multiple times before.  Off the top of my head, there's Color ($42M), Flipboard ($10M A-round, $50M follow-on), Adkeeper ($8M A, $35M follow-on 4 months later), and plenty others that raised $5M-$10M before even launching.  

At first I thought this was crazy, but I think I finally understand.  Building a good software firm is far more expensive than people may think -- yes, you could have 5 guys sitting in a living room coding, and that costs virtually nothing.  This is how inDinero was just a year ago, and we figured that everyone raising more than $1M pre-launch was crazy.  Boy were we wrong...  

Ends up that it costs a lot of money to build a real business.  You have office expenses, server costs, and employees who would rather not live off ramen-level salaries.  Building features takes 3X longer when you're no longer incubating, because you care about testing and reliablity, you're dividing your time between building features and assisting existing customers, and you now care about writing maintanable code.  All your fundraising budgets were based around time to develop functionality, and now they're completely wrong.  Before you know it, you're raising 2X-3X the original amount you sought to raise.

When I first went out to raise inDinero's angel round, we were looking to raise between $250k-$500k.  But since we were getting a lot of competition for our deal, we thought we'd raise more.  Before we knew it, we were up to $1M in commitments, and thought we had more cash than we ever knew what to do with.  12 months later, we've realized that this was the best thing to happen to us.  As one of our angel investors put it to us, "given favorable terms, raise as much money as possible."  His rationality was two-fold:  1) the bubble won't last forever, and 2) startups cost more money and require more time than the entrepreneur ever predicts.  

First-time entrepreneurs frequently ask "how much should I raise?", to which most investors respond "enough to get you to the next inflection point, which should be 12-18 months."  From a practical perspective, you should raise money in small chunks only on an as-needed basis.  But this is flawed thinking.  In order to do a successful fundraise, the entrepreneur has to drop everything they're doing, create competition and hype for their investment round, hope that the market doesn't dry up in the middle of their raise, and hope that the amount they raise lasts them until their "next inflection point".  The concept of raising money in small batches no longer seems as feasible anymore.

If I had to do it over again, here's how I'd think about the "how much to raise" question:

1 - Create a budget for 18 months of runway.  Factor in $5k/month for rent, internet, electricity.  Throw in $100k/year for servers, marketing experiments, conferences, travel, etc... Budget at least $80k/employee in payroll, benefits, insurance, and misc costs.  (you'll have to budget more if you plan on hiring more experienced talent)  edit:  we've been able to pay less than market rate purely because we offer more in equity.  But there have been potential hires who have higher financial requirements who we haven't been able to consider because of our budget restraints.

2 - Multiply this number by 2 because it'll take twice as long to execute on product roadmap.

3 - Increase the total runway by another 12 months in case the financing markets dry up. (**I believe this is likely to happen)

4 - Assume that I'll be talking to investors when I have 6-8 months of runway remaining, which means this so called "inflection point" actually needs to happen way sooner than you think.  

---

The amount you'll raise will obviously depend on how expensive your engineers are and how much revenue you're generating.  But if you run this exercise against your original prediction of how much you "need" to raise, you'll find that your intuition is probably off.  inDinero's original plan to raise $250k-$500k ended up being $1M, and though I couldn't understand why we needed that much, it ended up being the right thing to do.  

My only regret is not raising even more.

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About a year ago, I wrote about how I spent my day as a startup founder/ceo.  It's pretty interesting to reflect on it, because my role is pretty different now.  I no longer write code, I no longer do design work, and I spend most of my day reviewing progress and figuring out ways to make the company move better and faster.  Instead of building the product, I feel like I'm instead oiling and tweaking the machine that is building the product.  

I start my day around 10AM, and often have a phone call chat or early coffee meeting with a potential recruit, investor, or customer.  We hold a daily standup at the office at 11:10AM, when everyone on the product team talks about progress on their current projects.  I'll go through code reviews and designs that were submitted the day before to make sure everything is on track, and I'll spend half my afternoon working through product questions that anyone on the team has.  (remember how your professors held office hours for students?)

By 3PM, I've taken care of all immediate product needs and can finally work on new projects.  It could be designing a new feature, spec'ing out the engineering requirements of a new project, or brainstorming ways to improve the product in a certain way.  I'm often sifting through our massive list of user requests, emailing/calling/visiting customers to hear from them directly, or getting usability feedback on the design of a feature we're working on.  The team then breaks for dinner around 6PM, and I'll spend the next few hours either critiqueing design work or code that our engineers have written.  

I'll take a break around 930PM, shower up, then sync up with our remote team by 11PM.  We have about 5 people working in a different timezone, so it's the perfect time to chat with them without having any distractions from our local team.  I'll read and relax from midnight until 2, then head to sleep.  

* * * 

A few things you might notice:  

1 - I spend very little time in meetings (I'll choose two or three days a month where I'll pack my entire day with only meetings and no product work)

2 - I don't write any code and I don't design anything anymore (but I'm still very familiar with the codebase)

3 - I don't spend any time on user acquisition activities.  Since our product is still young, I decided that it'd be smartest to focus on improving product and improving word of mouth before doing anything brash with marketing.

4 - I don't spend any of my time doing operational tasks.  We have a wonderful manager (Andrea) who is handling our accounting, legal needs, HR/payroll, and other managerial work.  I also have an assistant who helps me with random chores and scheduling appointments/meetings.  

* * * 

This is probably completely different from how my life will be in a year from now.  If I had to predict, I'll probably continue to do design reviews and set product strategy, but I'll probably have all engineering-related work delegated off to my co-founder.  It's inevitable that I'll be spending more and more time doing "CEO work", which means raising more money, talking to investors, hiring and recruiting, among other things.  But in the meanwhile, I couldn't be happier leaving that to Andrea. 

If I had one point of feedback to give to the founder of a growing startup, it'd be to find your own version of Andrea.  She's a fast learner, a great generalist, and takes care of everything that isn't directly related to the product.  But even when she isn't doing operational work, she's talking to customers, helping me design new features, among other product-related tasks.  

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I've come to notice that too much of my time and energy is spent worrying about small problems in business:  among them being an intern not working hard enough, a small feature taking too long to build, a job candidate not working out, and other similar topics that don't have any meaningful impact on the future of inDinero.  Yet they seem to consume a disproportionate amount of my mind space, because these small issues stack up.

On the flip side, there are big problems that I should be spending 100% of my time thinking about:  Improving customer satisfaction, polishing product, hiring/retaining key hires, and making sure there's enough cash in the bank.  Most other topics are probably small, relatively meaningless, and should be ignored as quickly as possible.  

Whenever you're down about something, just ask yourself:  small problem or big problem?

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Back when I was in the fourth grade, I was trying to build a web application that would allow gamers to share FAQs and cheat codes.  There were dozens of similar sites out there already, but I thought I could build a stronger community than any other out there.

To start, I bought a copy of Dreamweaver 4.  It was known to be one of the best WYSIWYG (what-you-see-is-what-you-get) website editors of the time, and I had this misguided belief that learning how to use the software would be recipe for all my project's success.  What I didn't know was real web-application programming, or how to do that via Dreamweaver.  The software had real web GUI elements, and that led me to believe that I could just build a full-fledged web application without needing any real programming skill.  This was also the biggest mistake of my first endeavor to build something resembling a company.  

To make matters worse, I had recruited an army of classmates to help me with the website.  Some were assigned to help me populate the database with complete FAQs, others were assigned to find ways to drive user acquisition.  Over a dozen classmates.  I was the only one assigned to building product, and all of their time essentially went down the drain as I made a fake attempt to build this company off Dreamweaver.

My fellow fourth grade "business partners" began to lose confidence in the company after 4 months had gone by and I was unable to provide a substantive prototype.  The furthest I got was creating manual HTML pages for each and every game FAQ produced by my classmates, but this didn't seem scalable at all.  I didn't know what I didn't know, and wondered how sites like gamefaqs.com managed to get hundreds of listings without having an army of moderators.  I just assumed they had dozens of data-entry people full-time, and this ended up being one of those unfortunate forehead-slapping moments, now that I know how trivial my misunderstanding was.

The best lessons of humility are learned early in life.  Don't hire people you don't need too early, and surround yourself with others who can help you with all the things you don't know you don't know.  

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I've always thought that bureaucracy is a natural misfortune that only happens at big corporations and eductional institutions, but it seems to be pervasive among even tech startups and small businesses.  

The shocking part is that it usually comes from smart people with good intentions, who probably hate politicking equally as much as you do.  You might be dealing with bureaucracy at your own startup and not even realize it. 

My first experience with bureaucracy was from within my own company.  A few months ago, I was trying to let go of a hire who didn't work out.  Problem was, he was friends with everyone in the company, and all my partners felt I was making a fatal mistake.  I was determined to pull the trigger and have it over with by the morning after I made the decision, but it took me another two weeks to ultimately make the fire.  I begrudgingly issued a warning about his performance, and took the time to talk it over with each person on my team.  Why should it be this difficult for the founder and CEO to let go of someone she hired?  

Reason was because everyone cared.  Nobody intended to create unnecessary politics.  But since hiring and firing is the most important shared responsibility among everyone in a startup, I had to rationalize my decision better than any other I've had to make.  We discussed ways to prevent this "politicking" from ever having to happen again:  take more time weeding out hires with a bad culture fit upfront, and issue warnings so that every hire has at least a chance to change.  My partners wanted to know that they wouldn't be spontaneously fired "without cause", and I empathize with that.  

-----

My second experience with bureaucracy was actually caused by me.  A few months ago, my co-founder Andy was on the hunt to hire summer engineering interns.  He started recruiting friends from high school and math camp and wanted to get them offers as quickly as possible.  As we all know, the best candidates receive offers quickly, and hate having their future sit in limbo-land.  But there was a lot of rage from both me and my other partners because we felt that Andy was trying to make intern hires without our consent.  From our perspective, Andy was trying to bypass a "process" of interviewing that we had agreed to.  We wanted to interview every candidate to make sure we weren't making weak hires.  From Andy's perspective, the rest of us were being bureaucratic and taking too much time to give his candidates final hiring decisions.

The ultimate solution ended up being quite simple.  For contract and intern hires, we committed to a 72-hour turnaround timeframe.  This means that intern candidates would given a definitive yes/no decision within 72 hours of the first interview, whether or not everyone had the time to interview the person.  This way, everyone on the team had the ability to approve/veto an intern hire, and Andy didn't feel like he had to deal with bureaucracy from his own company.  Crisis avoided!

-----

I've come to realize that bureaucracy in and of itself isn't necessarily a bad thing.  Process exists for a reason, and politicking usually does stem from stakeholders who have good intentions for the organization.  Bureaucracy is only a problem when there's no perceived end in sight.  For example, my co-founder originally complained that he had no idea if he'd ever be able to give his future interns a definitive yes/no answer -- and that's just bad form.  With busy engineers with constant fires to put out, they'd never get to intervieiwng his future interns unless we created the 72-hour approval policy.  

Maybe none of this applies to your business.  But I've found that the more entrepreneurial and out-spoken your staff is, the more potential there is for bureaucracy in your company.  If you have a story about dealing with politics from within your small startup, I'd love to hear it.  

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What's neat about having an unusually young team behind inDinero is that when we make mistakes, we're quick to recover.  Instead of getting angry at myself (or at my fellow team members), we blame it on one thing:  real-world business school tuition.  The only differences are that our "tuition costs" come from lost revenues instead of from actual schooling, and that we're probably learning far more than our peers in college are.

I started thinking about how far can this go:  At what point do we have to blame ourselves instead of on inexperience when things go wrong?  But I realized that having a culture where it's ok to make mistakes is pretty awesome.  I feel like I could take risks and make bold moves, and that the worst thing that'll happen is a "shame cup" appearing on my desk.  I've also noticed that everytime someone introduces a bug to the codebase, there's very little blaming that goes on.  We immediately realize that those problems are likely to happen to us the following day, so we accept it and move on. 

Instead of regretting the mistakes you make, be appreciative of the fact that you're paying a very cheap price for important life lessons. You'll be less stressed, and be more able to focus on the things that matter.

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It's occured to me that everytime something "bad" happens to inDinero, it ends up not being as bad as I thought it'd be.  I've been trying to better understand which problems to care about, and which problems not to care so much about. 

Problems relating to servers going down or someone sending you a negative review pretty much ruin your day.

But there are more serious problems that we don't seem to think twice about:  such as your company's lack of revenue, or lack of product/market fit.  Why don't those stress you out 10X more of they're 10X more serious than the smaller fires you're putting out? 

If you plan on stressing out, worry about the things that are actually worth worrying about.

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Hope to see you there!

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"She's a perv, but Lady Gaga understands viral marketing better than anyone on the pop scene today." - Simon Dumenco.

See the full gallery on Posterous

I was reading up about the Grammys a few days ago and learned that Lady Gaga came as an egg and thought "what the hell is she thinking this time?!"  -- I felt a strong knee-jerk reaction in myself, and I couldn't help but wonder why she does such crazy stuff.

But I then realized that it's part of her brilliance.  Coming to the Grammys in the craziest of outfits (I don't think an egg can even be considered an outfit!) is credit to her creative and marketing genius.  My borderline viceral reaction turned into feelings of inspiration, and I've since watched almost every interview I could find of her on YouTube.

Gaga's background is pretty similar to that of many incredible entrepreneurs.  She started playing piano at age 4, writing music piano ballads at age 13, and she signed onto a record label at age 20.  But since she's in show business, we don't appreciate her upbringing in the way we do with Silicon Valley prodigies.  

What got me so excited about Gaga isn't her music and isn't her fashion sense, but rather, her ability to do everything:  she's an incredible artist, she knows how to sell, and she's mastered the art of fame.   She's the creative director, the artist, the fashion designer, the stage manager, the marketer, the PR expert, and the performer, all in one.  I personally sense that the best entrepreneurs do it all, and aren't just "business people" or engineers.  

"A part of my mastering of the art of fame… part of it is getting people to pay attention to things they want you to pay attention to, and not pay attention to things you don't want them to pay attention to." - Lady Gaga

In Gaga's 60 Minutes interview, she talks about her relationship with paparazzi.  She makes a great point:  if they're trying to profit off you, why not do the reverse too?  Everytime she walks in public with a crazy costume, she's creating more press for herself.  People can't profit off making fun of her fashion sense because she does it to herself every day.  It's as if she's comprehensively studied all the good and bad parts about being a celebrity, and she's circumvented all of the latter.  

Love her or hate her, Lady Gaga is one fine entrepreneur. I retroactively add her to my list of inspiration.

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It's difficult to find great customer service reps because you need someone who instinctively knows how to provide a great customer experience.  Why not recruit them from the places we know best, such as from restaurants and hotels?  

As we begin to ramp up on customer service these next 12 months, I'm trying to think of more ways to get the entire team to help out with recruiting.  Since everyone at inDinero seems to eat out way more often than they should, one idea would be to had out "casting call" cards to awesome waitresses, akin to what recruiters give to potential models.  

"You an awesome waiter!  Why not apply your skills towards helping business owners manage their money?  Better hours, higher pay, room to learn and grow." -- a very obvious career upgrade!

While visiting Zappos last week, I asked many of the employees what they were doing before working at Zappos.  I heard everything from waitress to store clerk to call center operator:  easy places to pick off untapped talent.  I predict that this will be one of our primary methods for recruiting customer service reps, and I encourage you to give it a try.  Let me know if it works!

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During inDinero's retreat to Las Vegas, we took a tour of Zappos.com's Headquarters, and spent the afternoon at their all-hands meeting.  It's easy to tour their office and think "wow, what an awesome place!"  It's far more difficult to apply your learnings back to your company.  To those who haven't yet visited Zappos, it's a company that cares immensely about culture -- probably more than anything, including sales and profits.  I think it's a noble way of running a company, and the most likely reason for their success.  

In an effort not to give lip service to their amazing cultural traits, I came up with an "action-plan" of things I plan on implementing at inDinero, as well as a short-list of things that we'll one day do in the next 1-3 years.

See the full gallery on Posterous

What we immediately plan on doing:

- Staff can give a $50 gift, once a month, to anyone at Zappos for doing something nice.  An $600/employee/year additional cost is an incredibly affordable way to spread positive karma around the company.  

- Putting all newhires through an "incubation" phase, where they learn everything about the company, spend time chatting with customers and answering support calls, etc..  I might try to apply a twist to this, where we make non-engineers learn some basic programming (so that customer service reps know how difficult it is to promise new features), and where we make non-designers do user interface design.  The idea is that we want everyone to be a strong generalist (yet also be an expert specialist), and this is an easy way to promote that culture.

- Having more fun more often.  Zappos throws a bunch of parties, sponsors many weekend outings, and puts a lot of emphasis on having a fun time.  As a young startup that's in the midst of building an empire works hard, but shouldn't forget to play hard too.

1-3YR "Wish-list" of things to do:

- Offering courses for staff to take.  For example, I might do a public speaking intensive on a Sunday, or Borden might offer a "sysadmin for dummies" course on Monday nights.   If we spend so much time and money trying to recruit our employees, why not spend just a little more effort on further educating our existing staff?  Or on the flip side, what if our intern Han knows some crazy Mathematics concepts that our engineers want to learn about?  

- Personal assistants for everyone.  We're a bit too poor to afford this service, but it'd be awesome to one-day allow all of our staff to share assistant resources.  At some point, we might be able to justify it as a way for employees to spend more time focusing on their work and the things that actually matter in their life.

- 24/7 Phone Service.  Most of our inquiries are during business hours, but the idea of having 24/7 phone service is incredible.  It sends a clear message to your current and future customers:  "we're a company that cares deeply about service!"  Of course, that message is associated with very obvious costs that we can't yet afford as a company.

Things we've always planned on doing but are now more committed to than ever:

- Customer service that WOWS people.  You might have noticed that we've been getting more compliments on our support the past few weeks, and that's because we've got an awesome team manning the emails/chat/phone 7 days a week.  (team Andrea+Tyler, who you can soon read more about on the inDinero blog)

- Focus on hiring for culture fit.  The potential recruit might be incredible smart, but if it's not a good culture fit, you shouldn't bring them into your company.  Bad culture fit is the reason why 80% of the recruits in our pipeline don't receive an offer, and we remain committed to hiring nobody if need be.  inDinero's last hire was in September 2010, and I have no problem not hiring until September 2012 if that means being careful about screening for culture fit.

- Promoting from within.  Instead of hiring an outside VP of X person, we'll do our best to train our existing staff to grow as the company grows.  Tony Hsieh, CEO of Zappos, mentioned that hiring VP-level hires from the outside has a 50% failure rate -- meaning that you have a 50% chance of making a bad executive hire, even if you do extensive screening before-hand.  

To startup founders trying to build a strong company culture:  I think it's an awesome exercise to tour a bunch of different companies, and to see what ideas you want to apply over to yours.  Most tech startups in the Bay Area are culturally near identical to each other, so you'll have to be more creative in your search for companies that care about culture.

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I write this from a very cheap hotel in Las Vegas (< $40/night!) where a small group of inDinero staff decided to take a three-day trip.  It's our first trip as a company, and it's been an absolute blast.  As one friend of mine said, "don't gamble away all of your investment money!"  Rest assured, we remain as frugal as ever.  

Until now, I've always wondered:  why don't all startups take their entire company on outings like these?

"It costs too much money"

It'll end up costing the company $1500 total in airfare and hotel rooms for 8 people (inDinero is 6 people full-time, but we have a large army of contractors).  We'll probably do two of these big "sleep-away" trips per year, so doing the math, it's about $400/person/year.  $400 in extra costs to make startup-wage employees is an incredible benefit that everyone in the company appreciates.  People who think we're wasting precious money need not worry.

"It costs enormous time and productivity from employees"

We left for the airport on Wednesday evening, which meant that we lost two days of full-time work.  What was interesting though is that for the two weeks leading up to our Vegas retreat, people seemed to put in over-time and work harder to make up for the time they knew they'd lose this week.  If I had to guess, our overall productivity from the past two weeks will end up being marginally less than it would have been otherwise.  

On the flip side, our productivity as a team will probably increase upon our return.  Team building actually works when you spend a bunch of time with each other in vacation-mode.  We also had a business justification for our trip:  visiting the Zappos Headquarters.  We spent the morning touring their office, then the rest of the afternoon at the company's quarterly all-hands meeting.  We learned so much that we plan on bringing back to the company.  

inDinero's next retreat

I definitely plan on organizing another company-wide retreat in the next few months.  With enough bargain shopping, it's super affordable to do.  With a business justification (such as visiting Zappos for a day), there's a real purpose to traveling somewhere.  A few other ideas for retreats I had were to visit Disney's Imagineering team down in Southern California, to tour New York City's tech startup scene, or to attend Berkshire Hathaway's Annual Shareholder Meeting in Omaha.  What cool ideas for company retreats can you come up with?

Returning to my original question:  why don't all startups have these awesome retreats?  I honestly think that the idea just hasn't occured to most founders.  "Retreats" have the negative connotation of being forced team-building exercises for employees, when in reality it's just a fun way to learn outside of the office.  Remember the field-trips you had as an elementary school student?  You'd often learn more outside of the classroom than you would sitting at your desk!  I think the same idea applies in the adult world, and we're trying to replicate that as best as we can at inDinero.

You're probably busy building your company, but chat with your team about the idea of a company retreat.  I'm sure they'd appreciate the free trip!

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Every few months, I get obsessed with the idea of happiness and planning for the future.  What do I want to do when I grow up?  Throughout my entire life, I've seen school as simply a means to an end.  Graduate from 2nd grade, move onto 3rd grade.  I would be one year closer to becoming a real adult, and one year closer to making real money running a real company.  

Now that I'm doing just that, my idea of progress has been turned onto its side.  I no longer live my days as means to an end.  A few years ago, I thought that selling a company for millions of dollars would be the ultimate dream.  But I've since realized that finding liquidity probably wouldn't make me happier.

I was having dinner with my partner-in-business Andy this evening, and asked him how likely it was for us to be running inDinero 10+ years from now.  He suggested to me something among the lines of, "Most entrepreneurs go into business thinking they're going to build something huge.  You have to be naive to think that there isn't a chance that we'll end up selling."

My next thought to myself was "would I actually be happy being a serial entrepreneur?"  Investors continue to assume that I'll build numerous companies over the course my lifetime, and at one point, I did too.  But I'm sick and tired of thinking that everything I do has to lead to an ultimate outcome, and it's taken a toll on the way that I think about my own happiness.  Why does there have to be an end-goal when I find myself enjoying life day-by-day?

We continue to run inDinero as if there will be no ending.  Being conscious of this fact means that I can figure out a better, more fulfilling way to make myself happiness in the long-run.  In fact, my "ultimate" career goal is to build a lasting company that has no ending (and hopefully, that company happens to be inDinero).  Many organizations, companies, and empires have had extroadinary influence on the world, but very few have survived for more than a few hundred years.  Building a company that's built to last won't only satisfy my ego, but force me to find happiness in building a company where people look forward to coming to work everyday, without it riding on the hope of finding liquidity in its stock.  

My big takeaway is mainly directed to career-minded young adults:  while society wires us to work towards achieving that "next step" in our lives, take the time and make the effort to figure out what ultimate happiness actually means.  Will selling a company for a bunch of money drastically increase your happiness?  Unlikely.  How about the idea of knowing that you've helped thousands of people with a problem that no other company has been able to solve?  That type of fulfillment is priceless.

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