Justin Mares

Think about the last time you were at a restaurant. Great meal, enjoyable conversation, a few drinks and a fun night out. You’re enjoying the company, the time away from work, the background noise and the conversation.

Then the check comes. Confusion ensues.

Even though we can print organs, fly to space, create self-driving cars and eradicate smallpox, for some reason splitting a check among 3 or more people still remains nearly impossible.

Plenty of times I’ve wondered why this is. Splitting a check should be relatively straightforward – each person takes what they ordered, adds a 20-25% tip and pays that.

The act of splitting a check is so complex because it involves other people. When emotions get involved in otherwise rational decisions, they quickly make a simple situation more complex. They force new decisions on you. Do I want to be a nice guy and pick up the check? Can I get away with having the bill split evenly, even though I ordered the most expensive item on the menu? Can I under-tip and hope nobody notices?

These internal questions add layers of emotional complexity to what is otherwise a basic equation. Your answers to these questions can depend on how you’re feeling at the time, whether or not you recently got paid, how your relationship with your girlfriend is, and so on.

Emotional complexity is everywhere: hiring, firing, working with others… The ability to successfully navigate this complexity can literally make or break your career. Rationally, you hire someone to do a certain job. You set goals, benchmarks and metrics to help judge whether or not someone is meeting expectations and doing a good job. Again, rationally, if they aren’t hitting the goals you’ve established, you should part ways. No hard feelings.

We all know this isn’t how it actually works. I’ve been fired, seen others fired, and recently been the one actually doing the firing. For those that haven’t done it yet: it sucks.

I’ve been laid off once and fired twice. Once because the company was going through some hard times, another time because I took off 18 days in a row (sorry LA Fitness), and another because I underestimated how much work 20 hours a week was when you’re trying to get a company off the ground.

Being fired was not fun, to say the least. As the one being fired, I didn’t think rationally about how I was late on a few projects, or how my last project wasn’t exactly my best work. My immediate thought was that it was personal – they didn’t like me, I had somehow offended the wrong person, I would never be successful in a career, etc. My emotions got involved and made the firing more painful and personal than it should have been. It removed the possibility of treating it as a learning experience, and instead made the event a blow to my self-confidence.

As hard as they can be, such situations can also be an advantage. In the case of getting fired, I was able to get some clarity (once I got over the emotional aspect) about what I wanted to learn and what I wanted to do with my life.

This can apply to other situations, like finding a job. Rationally, a hiring manager *should* go with the most qualified candidate, but will often hire someone they know and like. What this means for the “unqualified” candidate – someone without the perfect resume or the right connections – is that you can get a job by introducing emotion to what would otherwise be a purely rational choice. Take them to coffee, do informational interviews, keep in touch via email, etc. Build a relationship instead of a resume to turn a rational decision into one based largely on emotion.

There’s nothing incredibly insightful here that others far smarter haven’t talked about. I guess my main point is that I’m constantly surprised at how many decisions in the world are driven by emotions and relationships instead of the intelligent, rational adult mind that I thought dictated most things. Envy, greed, fear of missing out, kindness and reciprocity are all very human emotions that have a real impact on how the world works. And I didn’t realize that until I started thinking about how to split a check.

I was sitting there at lunch, sweating, staring at the stranger across from me. I had no idea what to say, no interesting topics to bring up. The lone thought racing through my mind, other than wishing this would end, was the disappointment I felt in my inability to make simple conversation for even 10 minutes.

That was the first day of my social workout.

Two years ago, I made a conscious effort to work on improving my social skills. Around the time I started Roommatefit (while still in college), I realized my mediocre interpersonal skills weren’t going to help me succeed. I needed to get a lot of help from others smarter than me, and talking to people via email and Twitter wasn’t going to cut it.

Beginning my junior year, I made it a habit to grab coffee with at least 1 new person each week. The summer I was in San Francisco, I got coffee or lunch with a new person 3x per week, and went to a startup event once a week with the goal to initiate at least 5 conversations. At the beginning it was horrible. I would jump from awkward conversation to awkward conversation, have one good one, and follow it with a painfully strained exchange of sentences that some would characterize as talking. But I practiced, and I improved.

I know since I consciously started working on this I’ve been a lot happier. Today, for example. I went to a lunch with a friend, an acquaintance and a few other people I didn’t know. Two years ago, such a situation would have made me nervous – I would have been unsure of myself, forced conversation and had a horrible time. Now, it’s not a big deal. I had a great time, met some cool people and am grabbing coffee with one of them later this week.

Being a pretty awkward guy has also helped me relate to others who may not have spent as much time practicing their social skills. I understand how others are feeling when meeting someone for the first time, and it’s easier for me to lead conversations to a place where both parties are comfortable. Even a slight improvement in my social skills meant a big leap in my ability to connect with people, which has led to new and better relationships.

Now, although my social fears are (mostly) gone, I’m still working on them. Telling better stories, using more pauses, and adding verbal inflection (I’m a pretty monotone speaker), are all things I need to work on. I’ve learned that your social skills are like a muscle – you can let them wither, or you can work on making them stronger. Improving them followed the same pattern as lifting: you suck, you suck, you see some improvements, you suck more.You don’t have to be that quiet guy forever. After working on this for 2 years I have met more than 300 new people, many who have become friends.

The point of this isn’t that I’m some amazing socialite. I’m not. The point is that I’m better socially than I was, and happier for it. Working on my social skills have had a larger impact on my life than anything else I’ve tried to improve.

Thanks to Nate Speller and Dan Shipper for reading drafts of this. And to all my lunch and coffee partners for their patience over the past two years.

For two years now I’ve been drawn to starting companies. From my perspective it looks like there are few better ways you can have an impact on the world. Success (seemingly) requires hard work and smarts, less so connections and political savvy (though they help). Media, politics, large corporations all have billions of dollars of entrenched interests to keep the top dogs where they are. Startups less so.

Though there are good reasons to do do them, I’ve come to appreciate just how difficult the mental side of startups is. The experience of starting a company is the hardest thing I’ve done so far. There’s not much that can compare with the ups and downs, the emotional attachment you have to doing something that hasn’t been done before. And I’m not even tackling a problem like sending rockets into space, or changing payments on the web.

After meeting a lot of people in the space, I think that it is almost more important from a career standpoint than anything else. You can’t do well if you’re constantly focusing on negatives, if you have difficulty finding happiness in your day-to-day, and if you’re not in a good place emotionally. This stuff is hard, and being miserable throughout the process is a sure way to get out of startups altogether. I know too many talented, ambitious people who don’t have the mental makeup to stay involved in the game.

Gabe talks about this a bit with his Startup Career Path post, but I hear a lot of people talking about startups as if they are a one-shot deal. As if their current thing doesn’t work, they leave the game. Even if you don’t get out altogether, being miserable while being in startups is hard. It sucks, and it makes people less effective and productive, to posts like this.

The more people who can be happy and start companies, the better. If humanity is going to advance more quickly, we want more smart people starting companies to solve real problems. This means we need more people who can mentally cope with the ups and downs of striking out on their own. This is valuable even for those that fail, as starting a company leads to drastically accelerated learning.

There’s still a lot for me to figure out, but I’m starting to believe that personal development and growth should be a focus before (and during) the process of starting a company. Getting your head right should be as important as anything else. After all, if you succeed at the cost of being a happy, healthy, real human, I’m not sure that’s a positive. This is why I’m working hard to do things like the Daily Practice. To focus on the good things in life and try to take a long-term view of things.

There are so many things I want to improve: my writing, strategic thinking, productivity, health… things most people struggle with. What I don’t want to deal with is a life of work that makes me miserable and unhappy. And too many times I worry that’s where I’m headed.

Thanks to Nate Speller for reading drafts of this. I’d love to hear what you think of this type of post vs more marketing-related posts. Thoughts?

To start the new year, I’ve been thinking a lot about playing for the long term. About applying strategic thinking to both my life, projects and my blog for the first time ever.

I’ve learned a lot over the past year. One of the biggest lessons I’ve learned (that I touched on in Reification) is just how much stuff is fluff, and is guided by poor, short-term thinking. I’m talking about media’s reaction to startup launches, “new” SEO/marketing tactics that read like the newest flavor of the month, anyone calling themselves an entrepreneur, and the hundreds of people starting a blog working towards passive income.

I finished the book Mastery last week. In the book, Robert Greene examines the lives of some of the greatest individuals in human history: thinkers and doers like Ben Franklin, Charles Darwin and Leonardo DaVinci. One of the biggest takeaways from the book was realizing just how long their accomplishments took, and how much work it took for them to achieve any level of success. For example, Paul Graham was bouncing around, painting and doing consulting until he was 30, and didn’t start YC until he was 41! That means for 10+ after college years he was hacking, painting and developing his creative skills. Then, for 11 more years he was applying that creativity towards his own startup and thinking about them in general. Only after all of this did he have his breakthrough idea about how startups worked and started YC – a full 7 years after he sold Viaweb. 20 years after he graduated college.

20 years. That’s a timeframe I can’t begin to comprehend right now. 10 years ago I didn’t even know what a startup was, much less how one worked. Unfortunately, I think a lot of startup thinking is focused on the short-term. People forgo their health, friendships, relationships and happiness chasing a short-term financial payoff. I’ve felt myself falling into this before. It’s easy to do: every time you see a story about a 26 year-old worth $x million, it’s easy to think “that guy has it all”. This type of thinking seems too common in the Hacker News/TechCrunch driven startup culture of funding, disruption potential and acquisitions. This type of news can even make it seem smart to play for the short-term: raise a big round, hire celebrities, etc.

What Robert talks about in Mastery is different. His big point is that to succeed, you must subsume your ego to strategy. Let your goals dictate your actions, rather than the latest emotion you’re reacting to. This is the difference between copying a competitor’s latest feature, dropping other priorities in the process, and focusing solely on executing your company strategy. This is playing for the long term.

I’ve thought about it in the context of this blog lately. I could probably focus on writing better headlines, blogging more often and covering prominent topics to boost readership. I’ve decided I don’t want to go that route. I figure no matter what happens, if I keep writing 20-30 posts a year for the next 10 years of my life, my audience will grow no matter what I do. I’ll become a better writer and hopefully have things to say that others will respond to.

This approach brings with it a sense of calm. I don’t have to worry about traffic stats, subscribers or tweets. It allows me to let go and focus on the hard work of improvement, less on the shallow results. I can let go of the short-term, the daily worries about success, the ups-and-downs of vanity metrics, and focus on the long-term hard work. At the very least, I can try.

My recent post, Entrepreneurship and Envy, has gotten more attention than anything I’ve ever written. In the process of reflecting on it, I started thinking about what causes envy in the first place. Why do I care so much about the success of others? Why is it something that bothers me and I have to work to overcome it?

I think a lot of it comes down to how you define yourself. It’s easy to make small amounts of progress towards starting a company and call yourself an entrepreneur. The title comes easily, the work less so.

I’m starting to realize all the posturing, the self-titling, is harmful. It isn’t real and has no impact on a reality. Roommatefit will not succeed or fail based on whether or not I call myself an entrepreneur. Startup success occurs in the sphere of reality, not in the fluctuating world of Twitter bios, business cards and LinkedIn profiles.

For me, this is so easy to do. Thinking about selling a company and what that would bring – money, success, happiness – none of those thoughts are real. The fake titles, the hollow accomplishments (1000 Twitter followers) – this is how envy begins. You build yourself up as someone and expect reality to conform. When it doesn’t, when the titles and expectations and things you’ve built up in your mind don’t happen, it impacts your actual wellbeing. Reification. Things that have never happened, impacting how you feel about yourself on a daily basis. And that sucks.

Doing this can also be strategically limiting. Define yourself as an entrepreneur and it makes you reluctant to take a job – even if that job may be the best move for you at the time.

How am I trying to deal with it? By going back to philosophy, by being present. By focusing on putting in the work and trusting that results will come at some point. By punching the clock at the end of the day, knowing I’ve done all I could to move forward in the 24 hours I’ve been given.

True happiness is.. to enjoy the present, without anxious dependence upon the future – Seneca

From an emotional standpoint, startups are really, really hard. Every day I’ve faced emotions and challenges that are completely new to me – hiring, setting company strategy, motivating a team and making product decisions.

On top of the emotional challenges, part of your “job” in a startup is to stay current with the latest technologies, startup advice, Paul Graham’s essays and things happening in startup land. As part of this, you will hear about people far more successful than you are. Far, far more successful. And sometimes, it kind of sucks.

It can be easy to occasionally feel envious or jealous of other’s success. Not a constant, obsessive feeling or anything like that – just enough of a problem where I recognize that this is something I have to deal with. Where I’ll read something on TechCrunch and think “wow look at how successful company x is.” I haven’t seen much written about this, but suspect (due to conversations I’ve had with other founders) I’m not alone in thinking/feeling this way.

After dealing with this for about a year, I’m doing far better. I rarely now experience feelings of envy for other’s successes, though some weeks are harder than others. There are a few things that have helped me tremendously to deal with jealousy and envy.

Focus on my friends and relationships. I’ve been incredibly lucky to have a great group of friends that are supportive, fun and smart. Even if I was to have a huge startup exit, these are people I’d still love to spend time with every day. I don’t know that everyone can say the same. Even if they can, I’m still incredibly lucky to enjoy the company of such awesome people every day.

Time freedom. Being able to wake up whenever I want, work out in the middle of the day, play basketball in the evenings and take lunches with friends is really enjoyable, and something most people don’t have the freedom to do. I can take midday walks, work whatever hours I want and still be productive. That is a real gift. Regularly interacting with people outside of tech/startups has also helped me realize how lucky I am to have such freedom with my time.

Career freedom. This might be a heavy bit of rationalization, but in a way not having a massive success is freeing. Success, while awesome (I’m sure), also locks you into things. If you have a successful exit, pressure is greater for your next company. If you’re the founder of a hot startup, the pressure is to improve upon that success. Think how the founders of Twitter feel – millions and millions of users, one of the most popular products in the world, and the startup community is hating on them for lacking a business model. With no success under my belt, I have complete freedom. If Roommatefit doesn’t work out within the next year, I can take time to travel, work with anyone I want, start something new, take on new projects, or work a job and relax for a while. Such freedom of choice shouldn’t be taken for granted.

Focus on the positives. There are so many good things about my life, it’s sometimes hard to appreciate just how good I have it. I’ve found it helpful to focus on things I’m doing well with, and be grateful for what I do have. Am I meeting interesting people who I enjoy spending time with? Am I healthy? Having fun? Learning new things? Taking risks? Building good habits? Asking myself these questions helps put things in perspective and realize I’m on a good path, even if it doesn’t lead to an immediate $1b valuation.

Get mentors. This is critical to dealing with the inevitable feelings of self-doubt, questioning and uncertainty that come with trying to start a company. My personal mentors have helped put things in perspective and keep me sane, while also giving great business advice. This is probably the most helpful thing I’ve found to deal with feelings of envy and doubt.

Focus on the work and not the results. Steven Pressfield uses a great quote in the War of Art: “we have a right to our labor, but not to the fruits of our labor”. This is really, really hard to do. However, I’ve been working to trust the fact that if I work hard and stay on task, good things will happen (this is especially true when writing a book). My focus right now is on building skills and discipline with the projects I’m involved with, and not as much on making tons of money. Or, at least, that’s what I’m shooting for.

Realistically determine what my goals are. Goals are incredibly important. Am I working to craft a life that makes me extremely happy, or working towards doing something massive that has the potential to change the world? At some point, something will have to give. Changing the world isn’t easy, and requires tons of personal sacrifice. This is one of the main things I took away from Steve Job’s biography, just how large a sacrifice he made to do what he did. If I’m working to optimize my happiness, why should I be jealous of someone who’s out to change the world by solving an incredibly difficult problem? They are on a different path that requires a different level of sacrifice and work.

Make a conscious effort to realize other’s successes exist independently of me. This is a hard one, and something I’ve taken from the Last Psychiatrist. As stupid as it sounds to write it out, it can be easy to see other’s successes as a reflection of your failures. Other’s successes exist independently of me. If someone I know sells a company, raises a ton of money or does really well, I had nothing to do with it. That action occurs completely outside of me, and has nothing to do with what I’m doing or working on. It’s the height of narcissism to think otherwise.

Don’t worry about potential or what others think. It can be easy to worry about what others think of you – how things are going, how well you’re doing, etc. I’ve been trying to focus on improving myself and becoming a better human. As one of my mentors put it, what matters more – being seen as high potential, or being a genuine human being people like and want to be with? In the end, even the rich and powerful want the same things: to be liked, have friends and be happy with yourself. Each of those things is accessible, regardless of how successful I am.

Don’t read tech news. Mark Suster has a good post on this. If it doesn’t help you or make you happier, why bother reading it?

Work with people in different situations. I’ve started volunteering as a 6th grade mentor at a low-income school nearby. It’s weird: outside of a startup context, you realize that other people are happy, even though they may not be changing the world or making gobs of money. Even outside of this reality check, it’s good to work on something that concretely helps another person and isn’t focused on making money. It’s helped me realize it’s a privilege to worry, even for a second, that I’m not running a company with the potential to make $100m in revenue. Most people have much larger problems.

Objectively look at the career ladder. It helps to think about how I feel right now (envy, not like a success) and compare that to where I was last year. For me, if you told me two years ago that I’d be running my own company, be in Entrepreneur magazine, had the chance to work with Gabe Weinberg and Noah Kagan, and live in SF for 4 months, I would have told you I’d be ridiculously happy. That’s how I would have defined success two years ago. I am ridiculously happy – but in terms of my career, don’t feel at all different. Instead, I want to sell a company, become an “influencer” and take on even more ambitious projects. My (very) small successes have only opened up a new level of wanting in terms of career achievement.

Practice stoicism. I am constantly trying to remind myself that in the long run, none of this really matters. There are so, so few men who really stand the test of time. And for those that did, what good did it do them? I love this quote from Sebastian Marshall:

That leads me to the final point, which is you gotta remember this is all a circus. Life is really a circus. Are you such a big deal that you can’t be embarrassed, or make a mistake, or do something wrong? No, you’re not. You’re not a big deal. At least, I’m not a big deal. I’ll say some stupid shit at some point, and get embarrassed, and look bad. Oh well. If things break the right way, I’ll also found branches of science, inspire people, build amazing businesses, found charities that actually work, make art, fund art, fund science, build a virtuous international dynasty, and all sorts of other stuff. But if I try and fail? Well, whatever, I’m not such a big deal. I can be embarrassed. It’s okay if I get something wrong or say something stupid. Most of what we obsess over is going to turn to dust anyways.

I hope this is helpful to someone out there. It’s helped me to reflect on the above, and just realize that life is short. In that context, it seems silly to worry about the millions or billions of dollars you don’t have. I’m working on improving myself and putting in the work to do big things. Hopefully, one day, some measure of success will follow. If not, I’m working on being ok with that.

Thanks to Jordan Messina, Nate Speller, Josh Albrecht and Adam Paulisick for reading drafts of this post. Special thanks to Adam, who’s thoughts and advice have helped me think about this issue over the past year.

Hardest isn’t the right word. But one of the most difficult things is to understand that there will always, always be someone or something who is better than you are. And to accept it.

Lately, I’ve been struggling with this blog. I’ve been going back and forth thinking about why I’m even writing – what do I have to say that’s valuable? I’m not the smartest person I know (that would be Nick Pinkston), nor the best writer around my age (Dan Shipper), nor the most insightful (Venkatesh Rao of Ribbonfarm). What do I have to say that’s valuable?

Really, the answer is nothing. But that doesn’t mean I should stop writing.

Ultimately, I’m doing this as a learning process, and because I like to. I’m not competing. I don’t have to “win” at blogging. I’m doing it to improve. But not to win.

This sounds simple, but this was a massive mental shift for me when I came to terms with it. I’ve had some limited success so far in my life, and sometimes the expectation of succeeding flows into other areas. For example, I probably get too competitive in sports. I’ve been teaching myself programming, and gotten frustrated when I don’t immediately understand something. As I’ve come to expect success, I’ve also started to question and rationalize when it doesn’t come immediately.

Expecting success isn’t the worst thing, but it certainly isn’t a trait I want to encourage. Doing so would make me shy from difficult problems (starting a company, learning a language, etc.) and embrace easier ones. That’s not how I want to live.

What’s helped me get away from this personally competitive mental measuring stick is focusing on process. I know my writing has improved (see my first post), though maybe not as much as I’d hope. By paying attention to the act of writing, and trying to use writing as a way to expand and clarify my thinking, I know that I’ve grown. I’ve also realized that everyone experiences the world differently, and maybe it’s not a bad thing that I’m adding my perspective.

A lot of this comes back to philosophy. To stoicism. When you separate results from the process, and work on becoming unattached to outcomes, suddenly writing becomes a lot more enjoyable. As does just about everything else. I can write without worrying if I’m the best. I can start a company without being depressed that I’m not the most successful person I know. I can read without wondering if this book will help me get ahead. Success isn’t a bad thing, but I’m working on being less attached to it.

I came across a fantastic speech by David Foster Wallace earlier this week where he touched on the above ideas that have been bouncing around in my head. He said it better than I ever could:

“Because here’s something else that’s true. In the day-to-day trenches of adult life, there is no such thing as atheism. There is no such thing as not worshipping. Everybody worships. The only choice we get is what to worship. And an outstanding reason for choosing some sort of god or spiritual-type thing to worship – be it JC or Allah, be it Yahweh or the Wiccan mother-goddess or the Four Noble Truths or some infrangible set of ethical principles – is that pretty much anything else you worship will eat you alive. If you worship money and things – if they are where you tap real meaning in life – then you will never have enough. Never feel you have enough. It’s the truth… Worship power – you will feel weak and afraid, and you will need ever more power over others to keep the fear at bay. Worship your intellect, being seen as smart – you will end up feeling stupid, a fraud, always on the verge of being found out.”

Working to separate myself from outcomes has been the only thing I’ve found that makes me happy. Anything else, and I get sucked into a world of comparisons and envy. I’m learning and growing, and I’m working to appreciate where I’m at.

***

Unrelated, but I found this and I really enjoyed it – Louis C.K. on Everything’s Amazing and Nobody’s Happy.

This past week I took the trip of a lifetime and drove across the country with a friend. We went from Pittsburgh to Los Angeles in just about 10 days, camping out in state and national parks the whole time. We stopped in Chicago, Omaha, the Badlands of South Dakota, Mount Rushmore and the Black Hills, Boulder, Denver (and the first ever Chipotle!), the Rockies,  Arches national park in Utah, and hiked the Grand Canyon on the last day. I’ve never appreciated this country as much as during this trip. I hadn’t realized before just how massive and how beautiful America is. As lame as it sounds, it also opened my eyes to parts of the country that I had no idea existed.

Random stops in places like Lusk, Wyoming – a town of less than 2000 people – were experiences I’d never had before. Seeing the massive tracts of farmland in the Midwest and small towns dotting the South Dakota and Iowa countryside were things I’d heard about but never experienced – experiencing it gave me a whole different appreciation for where I live and where I’ve grown up.

Being in these places also made me think about what I’m doing career-wise and the current state of startups in general. Outside of startup land, there are people who experience very real problems. Many of the people I met didn’t have tons of money, were overweight, and many didn’t seem happy (as subjective as that is). Not to say that people in cities or in startups don’t suffer from the same problems, but I definitely felt like I was outside of my standard well-educated, dynamic bubble of startup people.

Again, there’s nothing wrong with any of the people I met. Most of them were exceedingly nice and friendly, and happy to talk to someone who was driving through the country. This experience just got me thinking about the types of problems startups are trying to solve right now – sharing photos, mobile advertising, gaming, etc. These aren’t issues that normal people struggle with, and don’t have a powerful impact on the lives of individuals. And yet, this is where many startups are focusing these days.

There’s nothing wrong with trying to make money by doing a startup – in fact, it’s one of the main reasons I started Roommatefit. I have nothing against anyone trying to do one of these startups (unless you’re trying to do another deals site, then I get annoyed), but there are much more real problems that companies could address. If you think you have the power to make an impact, doing a meaningless startup is an opportunity cost and a chance wasted. Education is broken. Healthcare and nutrition are broken. The employment and job markets are broken. In a very real way, finance (and how people manage their money) is broken. People have addictions, are unhappy, struggle emotionally, and waste much of their time on unproductive activities. There are hundreds and thousands of potential companies that could address any of these real issues, and have a meaningful impact on the lives of millions of individuals. Google is a great example – in a way, they have been one of the main educators in my life. They have made massive amounts of information available to anyone online, for free. Amazon, PayPal and Apple have all had tremendous positive impacts on my life. I wish there were more companies aiming to do the same.

With all we know about human behavior and psychology, and with a device (the phone) that everyone has on them at all times, it surprises me that more companies aren’t aiming at improving the emotional part of one’s life. I think this is one of the great unexplored areas of the web. So far, the focus has been on improving certain small tasks (online calendar scheduling, social networking, online payments, etc.), but that’s starting to shift a bit. I think the next wave of startups will become a deeper part of people’s lives and work to improve their emotional lives. I think we’ll see companies that address addictions, health, parenting, personal development, etc. I hope to see more companies solving real problems, and am working to be one of those founders doing so.

One of the most significant moments of my life was buying a pair of shoes. Not just any shoes, but green Vibram toe shoes. I was the first one on my campus to have a pair. Why is this so significant? Because I’ve learned that success isn’t normal.

For the vast majority of people in the world, major success is not a normal thing. The average person in the US makes 43k, is obese, watches 3 hours of TV and works a 40 hour week. That is average. Nowhere is massive success a normal part of their lives (nor has it been a part of mine).

Wearing Vibrams around campus wasn’t normal. More than buying shoes, the important fact was that for the first time in my life I was willing to do something very different than others in my environment. Just being willing to be different and not do exactly what everyone else was doing, especially in college, has lead to a lot of great things. It’s not normal to read a book a week, to try and teach myself programming, or to cut sugar out of my diet. It’s not normal to start a company in college and be talking regularly with 5-10 successful, smart people. This doesn’t mean that not being normal = success: I doubt if you started drinking your urine it would make you successful (but who knows). I just know that for me, being willing to take chances and do things out of the ordinary has been a series of small steps that have led to a lot of good things in my life. First, I bought the shoes. Then, started a company, gave a pitch to 1000+ people, lived in San Francisco for the summer and have had an incredible stretch of learning experiences ever since.

Most of what I write about on here comes from things I’ve learned from my mentors and others who are far smarter than me. One of them, one of the most successful guys I’ve ever met, has carried around an extra copy of his favorite book since he’s been in college. He does this so he can give it away to someone he meets that he likes. That’s not normal, but neither is being the youngest ever person to occupy the position he’s in.

The same can be said for startup success. Startups that follow normal paths often struggle to get traction (partially related to the law of shitty clickthroughs). Who would have thought that the best way to start an international social network was to first capture Ivy League college students? Do what your competitors are doing, and you are likely to fail. This can also be applied to startup ideas – if you are thinking of starting a company now, good luck doing it in the deal or photosharing spaces. A company like Instagram getting acquired is a sign that a wave has passed, not that a storm is gathering.

Again, I don’t think success is something that intrinsically means all that much. Whether it’s a good or bad thing can be debated (my takes are here are here), but the fact is that most people wish they were massively successful, or even moderately successful, in some way. And the best way I’ve seen successful achieve success is to be different.

This post is based on something one of my mentors told me about success and taking small risks. A lot of it is said really well in this video. Highly suggested viewing.

Like I mentioned a bit ago, I was a participant in Stanford’s EBootcamp program for a 4 day stretch. It was an amazing weekend with some great speakers, really smart student entrepreneurs, and overall just an exciting event to be a part of. For the first morning session on Friday, they had booked Vinod Khosla of Khosla Ventures to give a keynote and answer some questions from a moderator and the students who were at the event. It was a really cool opportunity to get in touch with him. Khosla is a brilliant guy and is well respected in the Valley – he’s definitely a good guy to know. Two days before the event was to occur, I found his email address and shot him a 3 sentence email about who I was, what I’m doing, and what I wanted. His assistant replied and said he’d be happy to meet up before or after the event for a few minutes.

After he was done talking, he was (predictably) swarmed by eager students who wanted 2 seconds of his time to get his thoughts on what they were doing or to try and connect with him on a meaningful level and get his contact information for later. Unfortunately, he had to get somewhere and couldn’t stick around afterwards. I approached him as he was leaving, introduced myself and mentioned that his assistant had set up a meeting for us. We walked to his car for a while and I got about 20 minutes of his time, as well as the offer to keep in touch and valuable feedback about a few things I’m thinking of. Doing something differently (emailing before instead of a post-talk cold approach) allowed me to stand apart from the rest of the group.

This doesn’t always work out. I also approached one of the speakers, Konstantin Guerecke (CMO of LinkedIn) and asked if I could get 20 minutes of his time in a few weeks to help out with a side project I’m working on. He flat out rejected me. That’s all part of the game – unless you’re willing to go through a few rejections of that type, you won’t get to experience massive success (not that I have, but it’s a simple risk-reward equation).

What matters in the end with all this stuff is the mindset you use to approach it, not the actual outcomes. Who knows, maybe the next email I sent Vinod he will ignore and we will never interact again. It’s quite possible, as it was a short interaction and he’s a busy guy. What matters is building these types of situations into your life. If you are constantly unafraid of approaching someone, of talking about a massive idea you have, or of doing things that others generally shy away from, at some point you will stand out. By definition, you can’t expect to stand out by following the crowd. Doing things like emailing people you are interested in, working on a side project, or trying to teach yourself a valuable new skill will eventually culminate in a remarkable life – or so I hope. All I know is that i don’t believe you can do the same thing as everyone else and expect disproportionate results. As Seth Godin said, don’t get picked. Choose yourself. And when you have applied this mentality to several years of your life/career, people will take note of your success and ignore the trail of false starts, failure and trials of confidence that marked the way.