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Day in the Life as CEO

I thought it'd be interesting to document how my role as founder/CEO changes over the time, and that it'd be a great way to educate future inDinero team members how I contribute to the team. Back when we were just getting started, my job was simple: design features in photoshop, program them in ruby on rails. Show them to customers, gather feedback, rinse and repeat. But since raising money, I've been doing more "business-y" tasks to take inDinero to the next level. I'm sure my role will change over time, so I'll do this again when I feel that my role as CEO has drastically morphed once again.

10AM - Scan inbox for important messages, archive anything that isn't directly relevant to work. Schedule calls with potential hires, references for potential hires, and customers.

11AM - photographer from New York Times comes to visit us at the office. Takes a bunch of photos over the next hour. Noon - Eat Lunch, chat with customers over olark chat. Nice influx of requests today because of the mentions we got in American Express' Open Forum and Mashable.com over the weekend.

1PM - Call references for several potential engineering hires.

2PM - Talk to potential engineering recruit by phone, sell him on the idea of joining inDinero.

230PM - Chat with reporter from Reuters. Interview was scheduled only 18 hours ago! 315PM - Talk to lawyer about everything from employee compensation to other more confidential things :)

4PM - Another reference call for a potential engineering hire. Yes, we do a lot of reference checking!

430PM - Getting my new assistant up to speed on how to help me with my inbox, scheduling meetings to make my life easier, etc...

5PM - Review designer portfolios, work on improving candidate-flow for potential lead product designers.

630PM - break for dinner with the team.

715PM - talk to engineering recruit who we're about to extend a fulltime offer to. Answer his questions on why inDinero is the best startup in Silicon Valley, convince him to join us.

9PM - focus on only product, design new functionality based on the customer feedback I got earlier in the morning from people I chatted with through the inDinero website.

1AM - shower, read a book (this week, it's "Titan: The Life of John D. Rockefeller")

2AM - off to sleep, rinse and repeat process the next morning.

The Problem of Press

When you or your company receive press, something too good to be true happens: you feel a sudden inflow of success and accomplishment, people compliment you for the writeup you received, and everything feels great. Problem is, you start to get lazy. You settle into this comfortable feeling of accomplishment, when in reality, not a single thing has changed before and after the press you received.

A few days ago, TechCrunch broke the news that inDinero raised $1M from angel investors. I thought it'd be cool to share, but it never struck me as a big deal. Raising money is possibly the most boring part of working on a startup, so if anything, I wanted to be done with it. What happened next was interesting: dozens of my friends and acquaintances sent me congratulatory emails and facebook wall posts, and the moment felt like I was being congratulated for giving birth or doing something actually monumental. Raising money, in my opinion, is the least monumental thing that can happen to ones company. But it sure is press-worthy! While friends give me pats on the back, Paul Graham from Y Combinator tells me "Now you just have to not screw it up!" It's like what a good asian parent would say; just because you got As in school doesn't mean you'll actually succeed in life. I sense that a lot of first-time entrepreneurs get too much pre-mature press (because it's so easy to get), only to have it prevent them from doing what's best for their newfound businesses.

To prevent having this problem myself, I've conditioned myself to get more antsy after getting any congratulatory letter. I translate "congratulations" into "don't f*ck it up", and it puts me in this ideal place in mind where I feel good about having accomplished a very limited milestone, but understand that it doesn't actually mean anything as far the big picture is concerned. I highly recommend other first-time entrepreneurs do the same. Press is great, but in reality, nothing has changed since your writeup. Now back to building product.

I do what I hate

A few months ago, I wrote an article on how to come up with business ideas. I basically said to look at the world with a critical eye, and to keep track of everything that seems to suck. I still maintain that philosophy, and I recently discovered something about my "passions" in life: Everything I aspire to do is directly related to something that I dislike. I hate education, and I always have. School has never been a fun place for me. In elementary school, I was bored out of my mind. My 5th grade teacher discouraged me from my entrepreneurial pursuits. High school was more about dealing with girl drama than it was about learning meaningful things. By having spent more than 80% of my life suffering through these traumatic experiences, I've become interested in something that I've forever dreaded. While I'm yet to do anything super innovative to help the world of education, my past project internshipIN.com was a start in that direction. I realized that most of my learning came from working at a company, and so I spent my limited free time on helping students find real world internships. More recently, I decided that I hated accounting, I hated finance, and I hated money (although I enjoy the idea of having it). Managing finances is the one thing I despise most in building a company, and nothing stresses me out more than thinking about money. It's the root of all evil, it causes people to kill, it leads to people going to jail (think Madoff), and yet it's the biggest driving force behind every person's life aspirations. So I built a startup, Indinero.com, around the idea of making money suck less for businesses. It's something I plan on dedicating my career to. One of my friends in the investment world recently asked me why I'm building Indinero. After all, why would any young college student want to work on a finance startup? I think about my life as doing two primary things: Minimizing my risk, and minimizing my dissatisfaction with the world. This is an odd way to think about things, because most people think about their life in the opposite way. But I've come to realize that minus the shitty things that happen in life, I'm an optimally happy person. If I can remove the things that crush my soul, I'd be a happier person, and the world would theoretically be a better place. What would you rather do: Make the world a better place, or prevent it from sucking as bad as it does? I'd pick the latter, because it embraces the fact that the world is far from its optimal state. As my friend Manu told me, "make sure you're creating a painkiller instead of a vitamin." As I write this article, I'm suffering from the worst cold I've had in years. I'd pay anything to make this go away, and no cold medication has worked. So thinking about life from my current unhappy perspective, I see the world as a crappy place to live, and I'd be 10X happier if I simply wasn't unhappy. What a seemingly simple idea! Because think about it: during the happiest moments of your life, you probably didn't have anything special or unique that made you happy. But in each and every one of these happiest moments, you lacked the things that would otherwise drive you mad. This past summer was the happiest time of my life. I lived on ramen (literally), I shared a tiny Berkeley home with my team members at Indinero, and I was at the peak of my happiness despite my having zero material assets and close to zero fulfillment in my career. But I didn't have the two things that stress me out most: 1) school and 2) money issues. Between being on summer break and having $35k in the bank (and a startup that creates software that helped cure my finance concerns), I couldn't be happier. Or in more meaningful terms, I couldn't be happier with my life. I'm going to suggest the inverse of what Tony Hsieh from Zappos.com preaches. He's big on figuring out what makes you happy, and it was inspiring for me to see. But being honest with myself, I felt that it wasn't very satisfying because it just seemed too idealistic for even my liking. If you gave someone a week to think about what makes them happy, they still won't be able to give you the correct answer. People are generally bad at thinking of what makes them happy, so instead of focusing on happiness, I think it's much more practical to focus on unhappiness because it's much easier for us to identify and eliminate. Identifying sources of unhappiness is the easy part. Eliminating them is the difficult part. but it's what makes life seem more interesting. I think entrepreneurs are so fascinating because they first eliminate that point of dissatisfaction in their own life, then dedicate their remaining time to helping others eliminate it too. My mom is a prime example: growing up in a poor family, she had no choice but to wear her older brother's hand-me-downs. There's nothing more depressing than a teenage girl wearing her older brother's ugly clothing. So as a 13 year old, my mom designed and sewed her own clothing. Soon later, she started doing this for others. Fast forward a few decades, and it's the driving force behind her career and the jobs of hundreds of people. As pessimistic as it sounds, I think that identifying your sources of unhappiness is the most effective and honest way for you to live a better life. (and find ideas for your next company) What do you hate? How can you turn it into helping yourself and ultimately helping others? And that's the key to happiness.

If you have to interview a business person, talk politics with them.

If I could pick any one interview question for hiring a business person, I would ask them to talk about the conflict in the Middle East. What's their perspective? Do they take a stance? Do they try to argue something that they have no education on? What do they think of the supposed "enemy? And the most important part of this question: Do they even consider the other side's perspective?

You'd be surprised, because many people don't. Especially here at Berkeley. The debates between two sides of an issue aren't because our students are open-minded, but rather because there's diversity. With so many college-aged students on a single campus, it just so happens that there are multiple sides of the debate. But it doesn't make any of them open-minded, educated, or enlightened in any way. You're also probably thinking, "Isn't a political discussion a good way to end a friendship?" My answer is absolutely, and that's why I think it would make for an excellent interview question. Even if the candidate was a Zionist Jew, I would argue the Palestinian perspective just to put their pride in check.

I first thought about this when I was in a model United Nations session. I was watching my colleagues representing other nations debate among each other, argue about issues without a goal and without a premise. Had they never learned the tactics from "How to Win Friends and Influence People"? I saw from a first-hand perspective why the UN doesn't seem to get anything done. People leave just as ignorant or educated as they were coming into the assembly. People argue their stances, boost their egos, claim victory, and do very little to actually help the situation. And it's ironic too, because everyone coming into the model UN wonders why nothing useful ever gets done.

Which makes me think that it's not so much an issue about policies and actions... it's about the method by which we negotiate and resolve conflict with each other. The most important part of this being, "does the other side even attempt to listen to and understand my perspective?" Have you ever been in a situation where two people were in a political debate, and you could tell that the person who wasn't talking was only thinking about what they would say next in rebuttal? It's good entertainment, but no conflict resolution. This directly applies to the business world - if you're negotiating something, even as simple as an employee's salary, can you think about the other person's feelings, needs, and concerns?

I'm not saying that talking politics is the best way to see if a candidate is any good, but I do think that it's a great way to screen out people who aren't open to learning and listening. I've started to run this test on friends too, because it tells me how good of a listener they are, and how much they care to understand alternative perspectives. Business gets very personal very fast, so put your people to the test before you bring them on your ship.

Competition makes me happy

Most entrepreneurs hate their competition. Many of my friends would come up with a brilliant business idea, only to decide not to pursue it because someone else has already begun doing it. But if anything, they should be happy, because competition means two things: validation of a business idea, and pressure to innovate. If someone else is in your market, at least you know it's something worth solving. And if someone else is in your market, it means you have to create something truly useful. But investors don't always see this perspective... if anything, the first question I get asked is "how are you going to deal with Intuit as competition?" It's a reasonable question that I've put a lot of thought into.

The first thing to keep in mind is that for most internet companies, competition is irrelevant. As our friends at Zoho.com say, "... if there's anything I've learned from my years in the tech world is that companies don't get killed by competition, they usually find creative ways to commit suicide." Zoho is right, and we remind ourselves of that everyday here at Indinero. Chances are that your web startup will run out of funding, a co-founder will leave, or your inability to create a useful product will lead to the destruction of your own enterprise. And if you're able to get past those first barriers to entry, then I'll allow you to think a little about your competitors.

Now lets say that your company has an infinite cash runway, your company is capable of building a product, and you know that it won't commit suicide anytime soon. Even then, competition shouldn't be your primary concern. If you created a list of all of your competitors, 90% of them could probably be crossed off your list of concern because of their inability to innovate quickly. And of the remaining 10%, plot them on two axes: who is innovating, and who are you losing potential business to. You'll find that more often than not, no competitor is on the top right of the graph. It's often a big company (in our case, Intuit) that we're losing business to, and we know that they're not innovating at the pace that we are. More nimble startups, on the other hand, often make for good inspiration! Their mere existence, even if they have a better product than you do, does not mean that they'll be the reason for your failure. Keep in mind that your company will probably commit suicide in a creative way, and you'll never have the opportunity to evade the startup competitors you fear.

One valuable lesson I learned back in my middle school days was that having lots of competition was a good thing: I was in the web hosting space, which was and still is notorious for having terrible service providers. The rules I listed above applied to web hosting 5 years ago in that 90% of the competition was irrelevant, and many of the big players weren't doing anything particularly creative. There was an obvious pressure to do more than just provide diskspace and bandwidth to clients, which means that companies that couldn't keep up were able to fail earlier in the process. If anything, these failed companies should thank the competition for having saved them time!

So the next time you think of a business idea, embrace your competition and build your offering around unique things that your "big rival" isn't doing, and will likely never do. And if a friend or investor asks about your competition, you'll know precisely how to respond.

Why Indinero isn't "Freemium"

Over the past few days, a lot of people have asked: "Why doesn't Indinero.com follow the freemium model?" I wrote about my understanding of freemium a few months ago here on my blog, but ultimately chose not to go that route for several reasons:

1) When users pay, they're more serious about using your product. Instead of just going in to take a look, they'll take a more proactive stance on applying your product to everyday life. As a paying customer, they're also more likely to offer you valuable feedback that will change the way they use your product.

2) The cost per user is high - it costs us money to download data from bank accounts and credit cards. Charging our users immediately addresses this problem.

3) When you charge money upfront, people are more likely to convert and pay for your service. We talked to a few companies that switched from "no credit card upfront" to requiring that you enter your credit card from day 1. They recommend that we charge upfront to increase our conversion rate.

4) We're not sure if freemium is the right way to go. By charging money now, we can always implement a free plan later. If we started off as being a free service, it would turn people off if we ultimately changed our minds and went back to the premium-only model.

5) When raising angel/VC money, it helps to say that our company is earning money. Not having a freemium model got us closer to being able to make that claim. :)

But to be clear, these are just our preliminary thoughts. We may eventually have a freemium offering, but we'll be focused on building our paying user base for the time being. Many businesses prosper on the freemium model, and we're just not convinced that it's fit for what Indinero wants to achieve.

My company is post-revenue.

It's almost sad that I'm proud of this, but my internet company Indinero.com is finally post-revenue. In other words, people are using the product, people are paying to use it, and this marks the beginning of a long and beautiful relationship between me and the company I helped start. I've been rather discreet about my entrepreneurial progress, but I'll bring you up to date with my progress:

For a little background, I founded Indinero back in March with co-founder Andy Su. In a nutshell, it's software that helps entrepreneurs manage their finances easily. (Indinero is the Mint.com for Businesses) Our original mission was to make it easy for entrepreneurs to not only keep tabs on their expenses, but also to help them intuitively understand their finances. We got our first big break in April, when Lightspeed Venture Partners wrote us our first check. Getting the money wasn't as "lucky" as I enjoy making it seem... it was a planned process, and we spent many hours trying to convince Lightspeed Venture Partners that we were worth funding for the summer. This included building a product, sending them our first screenshots, and having my connections reach out to lightspeed partners to give recommendations. I'll repeat the most important thing again - they gave us money because we had built a functional prototype.

Fast forward a few months. In July, Indinero was chugging along with many alpha testers and promising feedback. Building a product for small businesses isn't easy, and we knew that raising more money would help us grow. With the goal of more funding in mind, we decided that the smartest thing we could do to convince people of our worth was to sign up of our first paying users, with the goal of relaunching a paid product on August 1st. We missed the deadline by a few days (programming's a bitch), but today we finally signed up several paying customers.

Having paid customers does way more than just prove investors that you're onto something: It forces you to think about building a product that people will actually pay for. As a programmer, you're forced to leave the confines of your comfy office to talk to prospective customers. You figure out what they want, what their pain points are, and you make it work. Something else changed, too: When we told people that we were planning on charging for our service (and that "free" wasn't on the menu), we were taken more seriously. People treated us like a legitimate business, and it further pushed us to make something useful.

Working towards building an internet service with revenue is like an endless spiral of goodness: it makes you build a good product, which makes you money, which makes people treat you more seriously, which makes you want to work harder, which makes you build a better product. I highly recommend that more people try it.

In my selfish ploy to get your feedback on Indinero, I'm giving out 50% discounts to the first 100 entrepreneurs who are willing to be guinea pigs for new ideas and features. More info here.

Lessons from Israel

We hear about Israel all the time -- mainly in regards to the the conflicts they have with the Hezbollah and the Palestinians. And with the stories that the press and our un-informed citizens tell, Israel looks like nothing more than a war-hungry country. But there's a lot that we can learn about from Israel, and it's interesting to see that they're theoretically a startup that's been bootstrapped from the ground up.

I recently returned from a Taglit-Birthright trip to Israel, which is a free trip that brings young Jews ages 18-27 to Israel on a 10 day journey to observe history, culture, and current-day industry. It was the most exciting 10 days of my life, and I want to draw some parallels between Israel and software startups. Israelis have incredible passion, resourcefulness, and persistence, and personality traits that resemble a startup that's doing everything it can to stay afloat.

Let's start with passion. Israelis have an incredible love for their country -- something that I've never seen in America in the 19 years that I've lived here. And I think it comes down to one thing: Israelis understand and care about the cause they're fighting for, and that's merely the right to exist. And to take this a step further, all Israelis are drafted into the army. No "normal" person in the states would want to join the army. From my uninformed perspective, it seems like the U.S. Army recruits primarily from poorer neighborhoods, and that most of our country's leadership didn't have the opportunity to serve. In Israel, every political leader has served as a solder, so there's this incredible unity that immediately reminds me of a tech startup. The founding CEO did everything from marketing outreach to coding the core product, and it's understood that the CEO isn't just "making orders." Compare this to a big company, where the CEO may or may not have any technical experience, and makes strategic and product decisions that the programmers don't understand. Reminds me of America...

Next, Israelis are resourceful like no other. Paul Graham from Y-Combinator says being a good startup founder comes down to being "relentlessly resourceful", and Israel was just that. When I visited Tel Aviv, they were celebrating their 100th year of existence. Just 100 years ago, Tel Aviv was nothing more than sand dunes, but the immigrant Jews built it up to being the second most populated city in Israel (after Jerusalem), and is now dubbed "Silicon Wadi" because of its incredible hi-tech scene.

Another great example of relentless resourcefulness comes from the 6 day war: Israel was being attacked by 5 1/2 armies on all sides, and in a fight for their survival, the government raised over $30M from Jewish Americans. In fact, if it wasn't for Israel's relentless resourcefulness, the nation wouldn't be around today. And the same thing applies to web startups: as an entrepreneur, you need to leverage your network in ways you haven't before.

I'll finish this off with persistence. For thousands of years, Jews have been persecuted merely for being Jewish. And at last, they have a country that they could go home to. I compare this to entrepreneurs getting up from failed businesses. Even if things don't work out, you keep on going until you build something that's truly great. Ignore the naysayers, and do what's needed to ensure the success (and survival) of your enterprise. And that's precisely what the Jews did with Israel over the past century.

Your business idea sucks, and it's your job to figure out why.

"Jessica, honey, baby, you're a smart girl, but your business idea is total shit, and none of your friends are going to be honest like your mommy is."

Hearing that hurt more than having teeth pulled, but it was for the good of humanity. It made me realize that most people refrain themselves from giving you negative feedback because they want to support you. If you have any relationship with the person you're asking feedback from, they'll find good things to say about your business idea, even if it's a lard of crap. As an entrepreneur, it's your job to get them out of this comfort zone, telling you the brutal truth.

Not only are people too nice when it comes to getting feedback on our business ideas, but many of us sub-consciously seek out "constructive advice" from people who we know are going to give us positive feedback. When someone compliments our idea, it's tempting to move onto getting more "constructive feedback" from other friends who we know will pat us on the back.

When starting a new company, you have the entire entrepreneurial community on your side. "Your idea is fantastic, and you should ignore all of the naysayers!" But I'm going to suggest something different: Instead of ignoring them, talk to as many of them as possible, and figure out why your business could potentially fail. By doing so, you'll be able to anticipate pitfalls that you can then account for. Not to mention, you'll be better able to sway the minds of people who would otherwise be skeptical of you and your idea.

People are too nice. Friends and colleagues will praise you for your entrepreneurial ambition, even if they sub-consiously think your idea sucks. I speak from experience -- when a good friend of mine pitches a business idea to me, I'm tempted to think only about the positives. It's my friend, so I want to uplift his or her sprits! But upon greater thought, I realize how flawed the business is, and I wish my entrepreneur friend knew what I thought.

I've been working on a stupid business idea for the past few weeks, and I've been so pumped about it after getting positive feedback from most of the people I talk to. But just this week, I pitched the idea to my mom. As a successful entrepreneur, I thought she'd be able to give good constructive feedback. And "constructive feedback" she gave. Within 10 seconds, she was able to give me a dozen reasons for why my business idea is flawed, and for why I lack needed experience to see it through.

I thought three things: 1) "Wow, my idea sucks", 2) "Wow, I'm a failure for an entrepreneur", and 3) "Wow, my mom's doing a fricken good job at convincing me not to drop out of college". I cried my brains out from thoughts of being a failure, then recovered with newfound knowledge on how to actually improve on my business. And of course, with renewed motivation to prove naysayers (like my mom) wrong.

Nobody wants to hear how much their idea sucks, and that's because most naysayers are shitty at providing constructive criticism. The last time my mom criticized my entrepreneurial abilities, we were driving to the airport. I remember wanting to jump out of the car rather than to hear her tear apart my dreams. I told my mom, "Why do you hate me so much?!" As an entrepreneur, you probably understand that having someone tell you that your idea sucks is analogous to being made fun of in middle school. You feel like you're hot shit, and then moments later, you realize that you're a loser who didn't know any better.

So suck it up. The best criticism acts like a slap in the face, and you realize that you're dreaming stupidity by thinking that you and your business is great. Maybe I'm a masochist, but I like it when my friends (and mom) tell me the fundamental flaws behind my business. As a smart entrepreneur, drag your friends to their feet and have them offer legitimate reasons for why your business could fail. With a sense of humor in all of this, you'll ultimately be a better entrepreneur, with answers for everyone who questions the purpose of your company's existence.

"If only I had a good idea for a business... then I'd be rich!"

Just a few weeks ago, I wrote about why 99% of entrepreneurs fail. But before you have the potential to be a failed entrepreneur, you need an idea. And many aspiring entrepreneurs don't know where to start.

Why are good ideas so hard to come by? Because most people try to think of them in either the wrong venue, or from the wrong-perspective. You need to stop thinking of yourself as an entrepreneur when you're thinking of an idea. You need to experience life as the world's victim, experiencing the flaws of the human life, and figuring out ways to improve on it.


How can I be the person with billions of great business ideas?

1) You're born with the ability to see the world in an abstract way, and can immediately come up with ideas on how to rid the world of its problems. You look at the world around you, and ideas are popping out as fast as babies from teenage girls. In other words, you're lucky.

2) And then there's everyone else who can't think of any good ideas. For the other 99% of the entrepreneurs in the world, including me, you struggle in the pursuit for ideas. You either need to retrain to be an idea person, or steal an idea from someone else. Or do both. So how did I do it? How did I go from having no ideas for a business/nonprofit to having more ideas than I could possibly work on? I followed the following "idea life-cycle":

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It isn't simple, but I'm going to suggest that you change your perspective on the world in one select way: It's as retarded as it gets, but be a picky bitch who can identify everything wrong in the world, and not be scared to share it with others. Everyday, you experience minor inconveniences in your life that are waiting to get solved. But after learning to become "mature adults," you've conditioned yourself to be happy with what you have, leaving the flaws in life untouched.

If you want to expose yourself to more ideas, you need to train yourself, and in every obscure way possible. Don't settle for anything that you're not content with. Experience the world for what it is, and be absolutely freaking honest with your feelings and frustrations in life, and come up with ways to fix them. Let's take one "simple" exercise that I remember doing in elementary school, and analyze it. Here was the thought process of my 6 year old mind:

I'd go to a restaurant with my Daddy. The wait is 15 minutes long and I hate waiting. Why can't I order my food NOW, and have it ready for me when a table is ready? Why do I have to wait on a line before I can even order? Why is it annoying to flip each page in the menu? What have my friends tried and liked? Why do waiters take so long to come take my order when I know what I want to order? Why is the portion so massive... couldn't they give me something I could finish? Why does it take so long to pay? ... And Daddy, why are you staring at the waitress?

I could go on and on with this story for pages, describing everything sucky about the way restaurants work. As you could probably assume, I was a very picky, impatient (and curious) child. I'd often share these thoughts with my parents, and they'd tell me to shut up and be appreciative with what I have. Fortunate for them, I've since become a jolly human being.

But unfortunately, I've lost this incredible ability! Think about the possibilities -- If you and I were able to experience the world like 6 year old Jessica Mah, then we'd have hundreds of potential business ideas each day. Sure, you'd probably be a life hater and that lonely kid on the playground who didn't have any friends. (which I was) - but at least you'd have lots of ideas, and perhaps even one fantastic idea for a company you could start.


Train yourself to be a child who sees more bad than good in the world.

If you fit into the second category of entrepreneurs that I listed above, (not being born an idea-person) then it's imperative that you train yourself to be the snobby 6 year old girl who has no problem complaining about the flaws in this world, then asking her daddy to fix them. For every flaw you see in this world, write it down in a journal. Be as general as possible. For example, based on my thought-process in a restaurant, I'd be able to come up with these ideas:

- Waiting on lines sucks - Waiting for servers sucks - Having people not know your preferences sucks - Comparing dozens of options with each other sucks - Life in general sucks

Now bring those general ideas back home with you, and get out of your 6 year old la-la land. Start thinking of ways the world sucks in all of those above ways, and ways to fix them. I hated waiting to get seated at a restaurant, so how can I improve that? Since the problem was so general, ("waiting on lines sucks") how could I apply this to waiting for anything in life? This simple example applies to waiting at theme parks, airports, traffic, waiting on new mail, and I'm sure dozens of other things that are totally not worth waiting on.

And for each of those ideas, we can break it down further into dozens of potential solutions. The airport example is being fixed in a lot of great ways that you can see: Online check-in and the Clear Pass, just to name a few. Commercial flight has been around for decades, yet nobody has thought of the above ideas until just a few years ago. This suggests that fantastic ideas are all around you, just waiting to get found.


So to recap on the lifecycle of finding ideas

As they say, the best ideas come from entrepreneurs who are fixing a problem that they saw in the world; not from any profit incentive or selfish motive. And there's no better way to do this than to see as many flaws in the world possible. Think of as many ways that life sucks. Every context you're in provides new opportunity to think of ways to improve on the world. Most of the ideas you come up with will suck, but many will hold great opportunity if you don't dismiss them so fast.
Then, apply these flaws to everything else in life. I'm serious -- keep a journal with all of the flaws in the world. Then in the bathtub, start brainstorming creative solutions to those problems. When you have a list of problems to solve, you have a framework from which you can think of brilliant business ideas.

With that said, go experience the world starting now, and be honest with your true feelings on why your life sucks. (even if it doesn't.) Then, transfer those ideas into entrepreneurial concepts. As a good idea-person, you're capable of finding every minuscule flaw in human life. Just try not to bring this to the business... and especially not to the bedroom.