What I’ve learned in my first year as a college dropout

September 1, 2014

One year ago, I took a leave of absence from Pomona College, moved to the Bay Area, and started working full time on Clef.

At the time, Clef was just a product — no one was really using it. One year later, we power logins on over 4,500 sites, protect more than $1 billion dollars in assets, and help thousands of people all over the world stop worrying about their security and start spending time on the things they care about. We haven’t killed passwords yet, but we’re getting closer.

But, those are just the highlights of what’s otherwise been the most challenging year of my life. Along the way, I’ve messed up, and learned, more in a single year than I had in the previous nineteen (and a half). In this essay, I attempt to condense nine of those lessons— from least to most important—in the hope that they’ll be useful to someone else.


It’s easy to furnish a house for free


For the first summer out of school, my co-founders and I subleased a fully furnished apartment in San Francisco. Three months in, when we moved from SF to Oakland in 12 hours, furnishings were not at the top of our mind. We started the fall with a completely empty house, I slept in a sleeping bag for weeks.

After a few looks at Ikea.com, the Salvation Army, and various sections of Craiglist, we quickly realized that it would cost us thousands of dollars to buy the basic supplies for a three bedroom house. With little to no available, this was out of the question.


Beds, chairs, tables, couches, desks, dressers, napkins, cups, mugs, spoons, forks, knives, plates, bowls, pots, pans…it gets expensive.

After digging a little deeper, I realized that I didn’t have to buy all of those things — I could get them for free. One weekend of determined searching later and I’d furnished our whole house from the Craigslist free section.


$40,000 is enough for me to live very well


When I left school to go full time on Clef, I was privileged enough to enter the Real World with no debt or financial responsibility (and healthcare through my parents) — I needed to support myself and that was it. Still, I was concerned whether I would be able to do that using only my savings and a small salary from Clef.

A year later, with my routines well refined, I spend around $1,700 per month on all of my living costs. I cook most of my meals, don’t buy new things (technology, clothes), rarely go out in a way that costs money, and don’t save anything. While certainly a non-trivial amount of money, for living in the Bay Area, I’m relatively pleased with only needing $20,000 post-taxes to sustain myself.


As I’ve considered other things that I would like, I’ve realized that with $30,000 a year post-taxes (or an additional $800 per month), I could live a much improved version of my life. $800 extra per month is a lot.

As we grow the company, and I continue to have no financial responsibilities beyond myself, a $40,000 a year salary (coming out to ~$30,000 post-taxes) is what I’ll work towards — and I’ll keep working to make that amount of money seem lavish.


Writing online is really powerful.


The summer of 2012 was the first time I ever took writing online seriously. During my time as a hackNY fellow, I wrote a blog post every day — in 3 months, I wrote some 70+ posts chronicling my first ever exploits in the tech industry. Even though many of those thoughts were misguided (and poorly written), they gave me a taste of how powerful writing online could be — during the summer, more than fifty thousand people read something I wrote at one point or another.

In the last year, as I’ve started writing again on my blog and on Medium, I’ve been reminded of that power.

The amazing thing about writing and publishing online is the potential reach from a single piece of content. It takes time, thought, and energy to refine thoughts into writing, but when that content is well received, that effort can be multiplied and returned hundreds of times over by readers.


It feels unreal — that one can put a single thing into the universe and hundreds of thousands of people can react and respond to it.


Dropping out is not like finishing school


Living and working with two individuals who did finish college at Pomona, I’ve had the unique ability to compare my life as a dropout to their lives as graduates. When I left school, I imagined that it would feel exactly the same — that leaving early would be just like finishing on time. As my first year post-college comes to a close, I’m realizing that while externally things look similar, internally I feel very different.

I describe this feeling to my friends at school by telling them that I’ve discovered the key to never growing old: taking a leave of absence from college.

With the potential for two more years in my back pocket, it feels to me as though I’m on an indefinite break. This break starts with Clef, and could take me through countless other stages of life, but at any point I can decide to end it and get back on the track of “My Future” by finishing college.


I’m scared of buying furniture because I know it’ll never survive college. I won’t get a pet for the same reason. Relationships I make tend to feel temporary because I know I won’t live in one place for long. The idea of finding a long-term partner, settling into a home, or having kids is a fairytale for a future me.

I feel like I’m not living the Rest Of My Life just yet, a liberating and isolating, empowering and limiting outlook.


I can tell in 5 minutes if I will like someone


Growing up, and all through college, social structures were built into my everyday life. Between classes, dorms, sports, and clubs, I was constantly surrounded by peers that shared my interests and values.

In the Real World, I haven’t had the same experience — I need to work hard to meet new people, and when I do, I often spend time with people that I don’t exactly care for.

As I’ve done more of this sort of socializing, I’ve realized that in 5 minutes I can get a strong feeling for whether the person I’m talking to is someone I want to spend more time with. It’s a combination of a few things: where our initial conversation naturally flows, their body language, the way we interact, and just a feel.


While efficient, I’m not sure how I feel about this revelation. At first glance, it seems great, but as I’ve thought more about it, I’m worried that in this initial judgement I’m likely biased towards certain types of people.

This bias has the potential to create a filter bubble where I surround myself with a homogenous group of people because I likely have a large number of initial false negatives.

Finding a balance here is something I’m working on now.


Discussing what I do is never easy


At home, at school, at social events, at dinner, at anywhere, the first question I’m always asked is “so, what do you do?” After a year of answering, I still haven’t found a response that pleases the asker and makes me feel good.

The first strategy I went with was the canned response (one explainer, three progress bullet points).

So, what do you do?

I work at a company called Clef in Oakland that’s building a replacement for passwords. With Clef, you just hold you phone up to your computer and you’re logged in — it’s easier and more secure.

How’s it going?

Awesome! We just crossed 4,500 sites using Clef, the New York Times called the technology “magical,” and we’re shipping [awesome new feature] in a week.

For quick conversations with strangers, this is tolerable (though boring), but when interacting with people that I care about (friends and family), it often feels disingenuous. With this quick response, I paint a rosy picture of success — leaving out all of the painful stuff that’s actually going on in the background.

The next strategy I’ve tried is the coy response.

So, what do you do?

I work in Oakland, what about you?

Oh that’s cool, so what do you do?

I’m an engineer.

Awesome! What kind of engineering do you do?

…on and on and on…

Occasionally, being coy allows me to quickly move on to other topics of conversation, but often it just leads to my conversation partner slowly pulling the original, canned response out of me. In the end, I’m often perceived as disinterested or unexcited about the company I run and left worn out by the questions.

With both canned and coy responses, I’m left feeling bad.


My relationship with this question embodies a constant struggle I have as the founder of a small startup: how do I handle the fact that every conversation I have about Clef has the potential to have a serious impact on its future.

Imagine we’re having a conversation about Clef.

In the span of 2 minutes, I tell you every good thing that has happened to us in the last 6 months. I drop easily memorable snippets: “we just crossed 4,500 sites” and “we were featured in the NYTimes.” I give off an air of extreme confidence and excitement. I bring you into my fantasy where Clef is a wild success and make you feel the highs that I really do feel. When you walk away from that conversation, you have a positive perception of the company I run. The next time your friend says, “have you heard of Clef,” you’ll remember, and share, my sound bytes and excitement.

Now, imagine our conversation goes a different way.

Because I had a hard day at work, rather than telling you about the recent successes we’ve had, I tell you about the horrible mistake I made or the deal we lost. I tell you how every day I feel like shit and I look for comfort from a friend who I trust. When we walk away from that conversation, yes I may feel comforted, but your perception of Clef becomes one of struggle. Yes, you support me, and no, you won’t go tell everyone about all the bad things, but the next time your friend asks “have you heard of Clef,” you’ll quietly say “oh yeah, my friend works there” and leave it at that.

Given how many seemingly arbitrary decisions I’ve seen made based entirely on perception and “feel,” it feels idiotic to do anything but constantly promote an image of positivity. But, from experiencing this positivity trap, I know that it’s emotionally taxing to keep the facade up when the reality of my day-to-day is nowhere near as pretty a picture.

What do you do?


Age is all context


When I moved to the Bay Area, the first people I really spent a considerable amount of time with were my older brother’s friends. Introduced to them as a little brother, I constantly felt younger, and slightly out of place. I love them (and I think they love me too), but for me, our friendship was always partially defined by my younger age.

As I branched out to new friends, I’ve realized that my age, and the way I feel age-wise relative to the people I’m spending time with, is entirely defined by our shared past context.


If a new friend knows me from high school, college, or through someone else, I often feel isolated by the fact that I’m younger than them. If we’re meeting for the first time through a shared interest or experience, age rarely comes up and I feel like part of the crowd.

A year after settling in, my closest friends, all from fresh contexts, are the same age, or older, than my first friends, but I rarely feel the difference.


Companionship is better than commiseration


Sad as it is, during the hardest times in the last year, I’ve often looked for someone to commiserate with. Someone to listen to me whine about the hard thing I’m going through. Someone to validate that the horribleness I’m feeling is normaland assure me that in one day or one week or one month things will be better.

As I’ve become more attuned to what makes me happy, I’ve realized that while commiseration can be effective, companionship serves me much better.

I first picked up on this after I’d taken a few breaks from work: the mountains, the beach, back to college.

In every place but Pomona, I found myself completely consumed by work; fretting about the things I needed to be doing (and the things that weren’t getting done). In contrast, on my trips to college, I was able to let go of everything (and return back to work with a clearer mind).

After observing this trend a few times, I started trying to pick apart why this was: the weather in Southern California? the academic atmosphere? Gradually, I realized that I was able to relax because I was surrounded by loving friends who were keeping me constantly engaged in other, less worrisome, things—the best kind of companions.

The worst part about being in a rut is that all I can think about is that rut. Every second of every day, I’m worrying about what I can be doing to get out of the rut. It consumes me. Thus far, finding companionship is the only thing I’ve found that can break me out of this. Having someone (or someones) who will do things with me, and take my mind off the badness, both temporarily eases the pain and allows me to return to work with a clearer mind.


In hard times, structure and relationships save my day


We’ve angered customers, lost deals, had funding fall through, made serious development errors, and messed up countless other times. So, despite all the companionship (and commiseration) I’ve found in the last year, there have been a handful of times where I’ve been close to quitting Clef, leaving Oakland, and returning home to curl up in a ball for a month.

During these times, I’ve found that two constants keep me in place until the inevitable rise out of the valley: structure and relationships.

I’ve added a second part-time job to my daily routine to keep me grounded and in place, structured my days so I’m forced out of bed every morning, added a weekly high note every Wednesday with Clef cooks (a community dinner we run in Oakland) and scheduled nightly emotional check-ins with my co-founders. These constant structures keep me going even when my world feels like it’s falling apart.

The two most important people in my life right now are Brennen and Mark, my co-founders, roommates, and best friends. In the dark times where I’ve considered giving up, my relationships with them have kept me going. The thought of harming them by backing out of the thing we’ve poured our recent lives into is too painful to consider. We support each other through our individual hard times because we each know that the other’s better day is coming soon.

Looking back on the last 5 years, one of the strongest constants has been the feeling that I am continually learning new things; that I am on an upward climb towards some sort of enlightenment. Unfortunately, while this feeling is exciting, it also guarantees that I’m inevitably wrong (or know nothing) about a slew of things at any given moment. In other words, I’m likely wrong about a thing or two in this essay. If you made it this far, you likely know a thing or two about a thing or two, so I ask that you enlighten me and help me return with a better understanding next year.

Jesse Pollak is still learning things. Follow him on Twitter here or subscribe below to get email updates.

Acqui-hires save our face but kill our dreams

August 27, 2014


8:00am, Monday August 11th

Today is one of the hardest days of my two year journey at Clef.

Already tormented by the ups and downs of fundraising, a big deal fell through on Sunday and we start our week feeling down. Standing at my desk, I struggle with the worst feeling I’ve come to know as a founder: aimlessness.

The success of our company feels like it is on the line, but I click between tabs and write pointless emails, waiting for something, anything, to happen.

4:03pm, Monday

me & a well connected friend and mentor on gchat

Them: hey, you there?

Me: yeah what’s up

Them: I have a crazy idea

Me: what is it? Love crazy ideas.

Them: Open to an acquisition?

At the lowest low, it’s amazing how wonderful a lifeline can look. Today’s lifeline comes in the form of an acqui-hire (a talent acquisition).

I stop struggling with what to do next and start imagining what it’d be like to be free from the struggle in the first place.

I stop thinking through the next deal and start wondering how I’d deal with the acquisition money.

I stop worrying about our company and start wondering about the company I’ll keep.

A significant amount of money in my pocket; a “successful exit” under my belt; the constant weight of perpetual uncertainty and fear lifted from my shoulders.

4:11pm, Monday

Me: doubtful, but not a hard no. Who’s looking?

Them: I can’t say but a very reputable place. I just need to know if your team is open to it. If “no” then it’s easy to disregard.

Me: I think it’s likely to be a distraction, but if you think it’s someone who would be interesting to us and would be serious about this than we’re open to a conversation. that’s coming from me and my two co-founders.

Them: Can you email me a profile or 1-pg PDF of the team’s background and technical experience? Trust me that it’s reputable. I wouldn’t waste your time.

Me: give me a little bit and i’ll get back to you. got to talk this through a little more.

The hardest part about running a company is believing. Believing in an idea. Believing in a group of people. Believing in the exception to the rule, the 1 in 100 victory. Believing through the best and worst times.

Believing in success against everyone and everything forcing failure.

Acqui-hires let us stop believing without admitting we were wrong to believe the whole time. We walk away with money in our pocket, a success on our resume, and members of an exclusive club, but the thing we believed in for years — that we poured our lives into for years — dies.

Acqui-hires save our face but kill our dreams.

5:43pm, Monday

From: Jesse Pollak <[email protected]>
To: A well-connected friend and mentor <[email protected]>
Date: Mon, 11 Aug 2014

hey, thanks for reaching out.

we had a longer conversation and we’re going to pass. in thinking through the potential deal, we decided that we’re not at a point where we can accomplish any of our personal goals through an acquisition. it’d likely mean killing the product we love and believe in and having high lock-in for modest reward at an unknown company.

all that, plus the inevitable distraction and morale-effect of having a “second choice” makes it bad timing.

I really appreciate you thinking of me and hope you understand.

Jesse Pollak is a one of the founders of Clef. He gets to build a product he loves every day of the week. Follow him on Twitter here.

The paradox of success

May 2, 2014

For the longest time, I imagined success as a compounding asset: as you became more successful, each future positive achievement became easier. I looked at large companies and famous founders and wondered how they could possibly fail.

A single experience has reversed my opinion on the subject: the perpetual struggle to see high month over month growth as a startup [1].

When companies are small, it’s easy to grow fast. We add 100, or 1,000, or 10,000 users and our graphs go up and to the right. It’s beautiful and exhilarating, but things get hard quickly. Every user we add this month makes the one we add next month less valuable. Every success we have this month makes achieving a success next month that much harder. Our past successes start to inhibit future ones [2].

As we meet goals and milestones, expectations are raised. Yes, for the investors who have a material stake in a company, but also for the friends, family, and peers who follow our progress.

The emotional and financial pressure to keep succeeding becomes overwhelming. The thought of publicly discussing the failures we have, or not succeeding in a bigger way next month, becomes terrifying.

It’s easy to become paralyzed in a constant uphill battle by the paradox of success.

Jesse Pollak may not always exceed expectations. Follow him on Twitter here.

[1] If you’re not familiar with this concept, it’s the go-to growth metric for measuring the success of a startup. Essentially, every month you want to convince more people to start using your product than you did the month before.

[2] The obvious counter-point here is that the ‘virality’ of your product achieving ‘product-market fit,’ means that much of this growth comes naturally. This may be true for some startups, but from my conversations with hundreds of other founders, especially those of SaaS products, there’s some of this, but most early growth is earned with a shit-ton of hard work and sales (and it does get harder to grow faster every month).

My low paying, early morning, exertion requiring job

April 4, 2014

Five months ago, I picked up a new job: every morning, I wake up at 6am, hop on my bike, and transport 50 bagels from Beauty’s Bagels to Awaken Cafe. After a quick cup of coffee, I bike on to my next job, my real job, running a tech company.

I earn $35 a week and get free coffee whenever I want it.

When I describe this daily routine to new friends, most look at me like I’m an idiot.

“You spend all of your time working on Clef and as a hobby you’ve picked up an extremely low paying job that pulls you out of bed at 6am and requires physical exertion. Uh, what?”  

When my hands are freezing on dark mornings, I often ask the same question. From a financial perspective, it’s pretty clear that this is not smart. Running a startup, time and energy are the two most important things I have — trading them for a tiny sum of money, and a free cup of coffee, is illogical.

But time and money aren’t everything: from a holistic perspective, I’m convinced the benefits of taking this second job are worth it.


Since I left college and started working for myself, finding structure in my day to day life has become very important. The biggest change I’ve made has been adjusting my schedule: in the middle of last summer, I switched to an early morning wake up (between 5:30 and 7am, optimizing for 6 hours of sleep). Unfortunately, despite the promises of proponents of this approach, my body has not adapted well to the shift: every day, getting out of bed is one of the hardest things I do [1].

Having an early morning job provides a concrete task that I need to get up and do, making the mental battle of escaping my blankets much easier.


As the founder of a startup, I spend nearly all of my time with employees of other technology companies. While this community is wonderful, spending too much time in any homogenous environment can feel numbing.

As part of my delivery job, I get access to two new (and very different) communities. Even if my interactions with them are limited, the exposure and human interaction just Feels Good.

I’m not the king of the world

For 90% of the day, I am my own boss. I set my own schedule, judge whether I’m being effective, and tell other people what to do. Combined with the constant glorification of engineers and founders in the tech industry, it’s easy to feel self important

When I’m delivering bagels, it’s the complete opposite. I’m just another employee. No one knows (or cares) that I’m an engineer or that I’m starting a company and only my bosses decide whether I’m effectively doing my job. Each morning, my bike ride transports me outside of the startup bubble and reminds me that most of the world isn’t so absurd.

Working hard outside of tech

I like to think I work hard. Every night, when I crawl into bed, I’m exhausted by all I’ve done that day.

Working hard outside of tech, however, is…different. After a few weeks of deliveries, I realized that my hours and exertion pale in comparison to the founders of the two small businesses I work for. The founders of Beauty’s Bagels are in every morning at 5am, on their feet all day making bagels in front of a huge oven, and only take Monday off.

Getting perspective on real-world hard work helps me calibrate my own expectations for myself.

Really, when I consider my second job, the earned petty-cash and free coffee is just the cherry on top.

Jesse Pollak delivers bagels and is working to save the internet from passwords. Follow him on Twitter here.

[1] Not sure why this is, but once I’m out of bed, I rarely feel tired for the day.

The constantly drafting mentality

February 25, 2014

The first blog I ever kept was updated every day. Each night, every night, I’d return home, pull out my computer, and stare at my screen until words materialized on the page. The strategy produced a lot of mediocre, mundane content and an occasional flash of something better. My mom loved it.

The second blog I’ve ever kept (you’re on it right now) is not updated every day. The posts are few and far between. At best I publish something new once a week, but more often than not it’s twice as long. Part of this is that I spend less time writing — I don’t sit down and force myself to write every night—but there’s another contributing factor: the constantly drafting mentality.

When I think about the internet writers I admire, I always imagine them having a huge collection of drafts. When they want to publish something new, these writers open up their collection, choose a piece that’s finely-aged, refine it to perfection, then publish it to wide acclaim. In their free moments, they funnel new ideas into this breeding ground and gradually massage old ideas into well-thought-out essays. The process is iterative, seamless, and easy.

Following in these writer’s footsteps, in my latest writing, I’ve adopted the constantly drafting mentality:

Every time I have an idea for something to write, I add it to my list. When I have time to write, I do things: (1) I go through my idea list and turn thoughts into a drafts; (2) I go through my drafts and refine them towards a “completed” product. When a draft is ready to publish, I publish it.

Unfortunately, with this strategy, the vast majority of things that I write never see the light of day. My draft list is not the oak cask that ages essays to perfection, it’s the early retirement home where they go to die. Yes, you guessed it, this hyper-effective strategy is an idolization-based figment of my imagination.

Drafting is an extremely effective writing strategy. Rarely is my first piece of writing the best incarnation of an idea I’m trying to convey. In fact, more often than not, it takes me more than one draft to figure out what the idea actually is. Just like building a company, constantly seeking and addressing feedback on writing can turn a wayward idea into a well thought out end product.

Constantly drafting has not proved to be an effective writing strategy. Just like a product, nothing I write is even close to finished — and it never will be. Creating a workflow around drafting  has pushed me towards an unreachable goal of perfection and stifled my output.

Draft carefully and consciously.

Are you one of my idols (or do you have super-human drafting ability and disagree with this concept)? Let me know on Twitter here.


Turning off the lights for fun and profit

January 31, 2014

When I was a kid, I was never particularly good at turning off the lights. My parents reminded me often, but I somehow always managed to forget. There was no malintent, I wasn’t trying to kill the planet or waste money, it kind of just…happened.

Since moving into my own home, I’ve been dealing with the opposite problem: an obsession with turning the lights off.

turning off the lights

Bathroom break? Better flick off the lights in the kitchen. Going to bed? Better leave the ground floor dark. Leaving the house? Better do a full-fucking-fledged sweep of the house to ensure nothing is on.

In the mornings, as I‘m heading from my bed to the front door, I have a rhythmic light-disabling routine: bedside lamp off, hall light on, room light off, stairwell light on, hall light off, living room light on, stairwell light off, open door, living room light off, out. It’s finely tuned to be efficient and effective and it consistently makes me feel like I’m putting way too much thought and energy into my light-killing strategy.

So what changed?

The obvious answer is that the financial burden is now on me, rather than my parents. I pay the electric bills, so there’s much more transparency into how turning off the lights effects my bottom line. Ultimately though, the savings from turning off the lights are minimal (tens of dollars, split three ways) and the transparency isn’t that increased: I’ve never consciously examined our electricity usage with an eye toward light savings and I don’t compare past bills to see how we’re doing.

I also doubt that it’s because I’ve matured into a more environmentally conscious human being. Though the science telling us that climate change is fuck-worthy-terrifying has only increased, I’d be lying if I didn’t say that over the last few years my involvement in the movement has waned. I can’t say I’m proud of this, but it’s the reality.

So, what turned me into an avid light manager? I think it may be about control and order.

The largest part of my life right now, Clef, more often that not feels out of my control. I can tirelessly improve, and distribute, our product, but at the end of the day, we’ll need more than our share of luck to ‘succeed.’

With the success of something I care so much about seemingly out of my hands, I think I’ve worked to find other areas of my life where I can be in control: I keep my room cleaner than ever before, I structure my days pretty strictly, I cook almost all my own meals, and I do a damn good job of turning off the lights.

Jesse Pollak is a light-turning-off aficionado who occasionally writes about things that won’t bore you to death. Follow him on Twitter here.

Turning off the internet at home

January 27, 2014

When Clef moved to Oakland, we decided that that we’d experiment with something new: no internet at home.

Today, five months later, we’re calling an end to the experiment and turning on our internet.

Over the last five months, I’ve learned a lot about how I use internet, how it impacts my relationships, and the power that comes with better understanding my addiction to constant connection.

This essay attempts to pick apart those learnings—the goods and the bads—and comes to no conclusion, just a better understanding.

Why we decided to turn off the internet

Working at a startup, the internet is the channel to our business. Wherever there’s internet, there’s the potential for work—we check our email, we respond to support issues, we fix bugs, we deploy code. With internet practically everywhere, this means that work creeps into every aspect of our lives.

Our old home in San Francisco still has the 3rd most production deploys of any location in Clef history (behind our two offices). I read and sent more emails in bed there than in all my years prior to starting a company. It wasn’t out of the ordinary for me to wake up in the middle of the night, see an email on my phone, and fix a bug before going back to sleep.

In many ways, this constant connectivity is wonderful. It allows us to do everything faster: faster email replies, faster bug fixes, faster recognition of potential issues. This speed is one of the things that’s enabled the current startup boom.

It’s also extremely draining: when all you care about is the success of a company, and you’re constantly in a position where it feels like you can work to make that success more likely, it’s easy to irrationally ignore the need to disconnect.

When we decided to turn off the internet at home, we did it to actively combat this uncontrollable urge. Newly disconnected, our goal was that conversation, relaxation, and social connection would become the default at home, rather than the subconscious pull back towards our inboxes and editors.

We’d still be able to work as much as we wanted, but our work-times would be distinct and discrete, rather than abstract and eternal. We’d be in control.

It was a thesis that we decided was worth testing for a week or two, so we delayed setting up internet in our new home. A week turned into a month and a month turned into five.

The good things

At the core, our thesis proved entirely correct. At home, even though I still had my internet connected phone, I was consistently more disconnected and relaxed. It felt really good in so many ways.

I got more sleep. With internet, it was easy to stay up late on my computer—over the summer, I went to bed between 12 and 1am every night. Without it, I went to bed between 10:30pm and 11:30pm. Those extra hours of sleep helped me switch to an earlier wake up and more productive mornings.

I watched less TV. With, I spent somewhere between 5 and 10 hours a week in front of a television at home [1]. Without, I trimmed that intake to zero and replaced it with more writing, thinking, and reading.

We traded screens for conversation. With, it was normal for the three of us to sit at our kitchen table for hours with our computers open. Without, long conversations on our couches about non-internet things are the nightly norm.

Not having internet at home taught me how addicted I am to continuous connection. As I started to understand and feel this addiction, and as I practiced moving from a connected to a disconnected space, I was able to translate the things I learned at home to my behavior in other, connected, places (i.e. everywhere). Over the last 6 months, I’ve significantly improved my ability to keep my device in my pocket and engage in a meaningful way with the people around me—no matter what’s going on online.

Really, I just felt more in control — like I could decide when I wanted to tune in or tune out. It felt empowering.

The not so good things

Unfortunately, like every decision, turning off the internet at home had it’s downsides.

Turning off the internet forced constant, hard, choices around when to work or not work. Not being able to just connect at home turned tasks that might have taken 3 minutes before (like fixing a bug) into a serious decision: is this issue important enough that I should leave my home, head to our office, and resolve or can it wait until tomorrow. This consciousness is exactly the reason we opt-ed to disconnect, but that doesn’t make it any easier to process. Constantly making these decisions is exhausting, especially when guilt can often accompany the non-work choice.

Coding at home (for fun or profit) is much harder without internet. When you’re experimenting with a new technology, the internet is your best friend —having to look up questions on my phone can be really frustrating [2].

Without internet, eating schedules for long work days are harder to navigate. Mark, Brennen, and I cook and eat 90% of our dinners together. When we had internet, this usually meant heading home around 7:30pm, cooking dinner, then returning to work or watching some TV. Without internet, when we left for home, we eliminated a huge number of post-dinner activities. This meant that we cooked nearly 100% of our meals at work. Our setup there is awesome [3], but it meant we spent nearly all of our waking hours in one place. No matter how many breaks we interspersed, spending that much time in any once location is exhausting.

Turning off the internet put a negative stigma around going home. The reasons above are part of it, but there was also just kind of an X-factor that is hard to describe—perhaps it’s just that we were there much less. It wasn’t serious, but in a high-stress environment, after 5 months, all three of us could feel that there was a bad vibe forming around being home. And, when we all felt that, we knew that we needed to make a change.

Reconnecting, for now

Spending nearly 24/7 with the same people is really hard. No matter how much we love each other (and I love Brennen and Mark very, very much), there are constantly interpersonal issues that we need to process [4]. Any external stresser that can complicate this equilibrium is something that needs to be identified and addressed.

The combination of problems with not having internet proved to be one of these stressers—so we decided to flip the switch (the other way).

Just like our decision to turn off the internet, though, we’re making this one with a provable thesis in mind (that it will relieve an unnecessary stresser). We don’t have a long term contract, and none of us are particularly attached to the actual idea of having internet, so if our thesis proves incorrect, we’ll just switch back. Essentially, we’re experimenting with our environment to see how we can optimize for peace and happiness.

Because the internet

Flipping the internet-on switch feels shitty. It feels like a failure. It feels like I set out on a cavalier adventure—a struggle to be different and act different—and came back with my tail between my legs. Like the internet is just sitting somewhere in some data center cackling.

But, especially after writing this, I’m starting to realize that the adventure isn’t even close to over. It continues with our newly created internet-enabled home, where I’ll be able to apply everything I’ve learned in the last five months to a new environment—hopefully making me a more conscious connector. But even that is just scene .02 of act .01.

The internet is going to consume literally every part of our lives. I’ll hate it and love it and tell it to go away in certain contexts, but then switch tunes and wrap my arms around it and hug it till it gets too big to hug.  I’ll try one thing, then try another and it’ll sneer its strawberry-sized internet face and call me a hypocrite (and I’ll happily whisper to my wireless router that, yes, I’m a hypocrite, but at least I’m not a shitty wireless router named ATT63200).

As the internet changes what it means to be me, I’ll try to change what the internet means to me.

Jesse Pollak is someone you’ve probably never heard of and maybe want to follow on Twitter

[1] Cutting television out of our lives hasn’t been all good. I’ve never been very into TV shows or movies, but Brennen (and Mark, though less so) is a huge pop culture buff (and movie lover). With internet, he was able to share this love with me and this was really valuable. Turning off the internet eliminated this shared experience, which sucked. I loved not having TV, but I hated losing a real way to connect with one of my best friends.

[2] That said, I’m fairly certain that coding without internet has made me a much better programmer. It forces me to spend a lot more time thinking through issues before turning to Google for help and it has helped improve my memory of language-specific syntax. Dash has proved invaluable for this.

[3] One of the nicest kitchens I’ve ever used—huge marble counter top, 6 burner set, dishwasher, big refrigerator, walk in pantry, and tons of kitchenware (and anything that isn’t there, they are more than happy to purchase for us). I can’t express how thankful I am to Michael and Joel (the owners) for creating such a wonderful environment—none of the last 6 months would have been possible without them.

[4] Over the last month, we’ve actually committed to taking a much more proactive approach to processing these sort of issues. This topic deserves (and will get) a full essay, but essentially, we’ve started doing daily check-ins on the state of our personal relationships. Every night, we sit down and talk about how we interacted and felt each day—what was good, what was bad, what was just really hard. It’s one of the most difficult things I’ve ever done, but it’s also proven to be more powerful and educating than I could ever imagine.

Am I killing the thing I love?

December 12, 2013

There’s no website I love more than Hype Machine — and I’m scared I’m killing it slowly.

What is Hype Machine and why is it so awesome?

If you’ve never heard of Hype Machine before, I highly recommend you check it out.

The Hype Machine keeps track of what music bloggers write about. We handpick a set of kickass music blogs and then present what they discuss [and stream] for easy analysis, consumption and discovery. This way, your odds of stumbling into awesome music or awesome blogs are high.

In other words, Hype Machine finds all the best new music in the world, curates it, and delivers it to your ears.

On any given day, I spend more than 10 hours a day listening to music they aggregate. Over the last 2 years, http://hypem.com is #1 in terms of browsing time on my computer. When friends ask me what I’ve been listening to, I just direct them to my favorites list.

There’s no listening experience I enjoy more, the user interface is wonderful, unique and intuitive, and the community is fun and filled with friends.

Hype Machine and money

Hype Machine is different from other music sites — all the music they stream is free and publicly available.

Musicians approve songs to be streamed on blogs for free, then Hype Machine (and its community) curates those blogs and streams the songs on their site. In return for the content, Hype Machine gives the artists and bloggers a ton of traffic and exposure.

I’m not well-versed in the details, but from what I do understand, this is a model that all parties are happy with (besides the occasional leaked song off an album that quickly gets pulled off the site).

At first glance, this seems like a huge plus for the company — free music means low margins and an easy path to profitablity. Unfortunately, a limiting factor on their profit-making ability quickly becomes apparent: in their quid pro quo agreement with artists and bloggers, Hype Machine can’t charge for music they are being given (rightly so).

Hype Machine is 100% free for users.

This leaves the site struggling to turn a profit through advertising on the site and affiliate revenue through song purchases.

Ads, ads, ads

Ads are a hard game. Services like Pandora and Spotify have been reasonably successful with inter-song audio advertising, but the bulk of their revenue comes through paid subscriptions.

For Hype Machine, I can imagine it’s even harder. Because of the whole “free music” thing, it seems like inter-song audio advertising is off the table. This leaves them with banner ads — an increasingly weak revenue opportunity (unless you have huge traffic that you can effectively target).

While the site has super high user engagement and time on page, little of that engagement is optimal for advertising. When I’m on hypem.com, it’s almost always in a background tab just streaming music — I almost never see aads.

Affiliate links

In the iTunes affiliate program, you can make up to 2% of a purchase. Even if each of the 400K unique visitors bought one song per month (I’ve never bought one), that’d still only be $8,000 in recurring revenue.

When you consider that most of the songs Hype Machine is streaming are freely available to download if you click through to the blog or do a Google search, the economics of the affiliate revenue aren’t great.

All this said, with hundreds of thousands of uniques per month, the site seems to be generating enough revenue through ads and affiliate programs to sustain itself — they’ve been around for 8 years and have never raised a round of funding.

Mobile  and native

In the last month, I’ve increased my listening time, but spent 0 hours on the Hype Machine website.

I’ve moved 100% of my Hype Machine experience to an Android app (free, created by 3rd party) and a Mac app (free, created by a 3rd party). I don’t think I’m the only one who’s making this switch.

Screenshot 2013-12-05 09.07.53

That’s not the kind of graph you want to see as a startup — especially when all of your revenue comes from display advertising and affiliate fees. Granted, there are some serious concerns about how accurate Quantcast data is, but anecdotal evidence (from myself and my friends who use Hype Machine) backs up this data. I also had an email conversation with Anthony, the amazing founder of Hype Machine, who confirmed the trend:

Your assessment that the web usage of Hype Machine has decreased is true, even if the overall Hype Machine usage across different platforms is not…our iPhone app usage has been growing well, even though it’s not free, which is what I am excited about.  

With low-cost listening apps (free on Android, $4 on iPhone), no inter-song advertising, and no affiliate links in apps (neither of mine have them and if they did, they would probably pay out to the app creator), there’s basically no revenue opportunity on users who do the bulk of their listening through non-web interfaces.

I’m terrified that by switching to better listening experiences, Hype Machine’s users are going to slowly kill the site.

What can we do?

We could stop using the platforms that have limited revenue opportunities, but choosing a short-term bad experience is not a recipe for long-term success.

We can tell everyone how awesome the platform is and how much it deserves to be successful (see what I’m doing here?). We can make a more conscious effort to purchase music through their affiliate links. We can buy the native apps they offer.

I’ll also say it right now — if there was a way for me to make a monthly “donation” to Hype Machine, I would do it. Would you?

Unfortunately, I’m unsure that doing those things is enough — I want to find a way to a new way to help, but don’t have a good answer to how. Any ideas?

Do you love Hype Machine and have thoughts on this issue? Let me know on Twitter or in the comments below!


Mashery/Intel acquires HackerLeague

December 3, 2013

A little less than 2 years ago, I sent this email to [email protected]:


My name is Jesse Pollak and I am a student at Pomona College. I am organizing a hackathon and would love to get the support of Hacker League. If there’s a time someone could talk to me this week via phone, I’d love to make it happen. My phone number is XXX-XXX-XXXX and I’m free almost all week.



Later that day, Abe got us set up on the Hacker League platform. A few weeks later, he connected us with Iron.io who would become the first ever sponsor for the 5C Hackathon. Six months later, I’d get accepted to hackNY and realize that the founders of HackerLeague, AbeIan, and Swift, were all hackNY alumni.

Today, I’ve helped throw 3 hackathons and each time HackerLeague has provided an awesome platform for organizing our attendees.

This morning, I was excited to wake up to the news that Mashery (now owned by Intel) has acquired Hacker League. In the words of the Mashery CEO,

“[Mashery] acquired the assets of Hacker League to take a product that makes hackathons great so that we could do more things to support developers,” he said. “It adds something that we can support the developer community with and eventually build parts into our core product over time.”

Without HackerLeague (and all the other support from Abe, Ian and Swift), I can honestly say that I wouldn’t be where I am today. I’m can’t wait to see the amazing things both HackerLeague and its founders go on to do in the future!


Advice on applying to hackNY

November 26, 2013


Over the last few weeks, I’ve gotten a few emails asking for advice on applying to hackNY. Each time, I’ve rewritten my thoughts on the application process — gradually refining the emails. Over the weekend, I decided to consolidate those emails into one, get feedback from the hackNY community, and publish it for anyone interested in applying to hackNY.

The following is the result of that process.

What does hackNY look for in applicants?

The #1 thing that we look for in applicants is a serious interest in building cool things. If you’ve built things that other people like, you’re in a great position to be a hackNY fellow. If you haven’t, but you want to build cool things, you’re still in a good position to be a hackNY fellow! The key to both of these situations is convincing the application readers that you’re a builder.

If you’ve already built a bunch of cool things, tell us about them! We want to see the projects you’ve created, hear why you created them, and learn about the problems you solved along the way. Let us know why you had fun and why you’re excited to build even more awesome things this summer!

If you don’t, we want to hear why you *will* build cool things. Tell us about a problem you have and how you’re going to solve it. Tell us about something small that you’ve started working on. Tell us about a class project that you got totally carried away with. Oh, and there’s no better time to start like the present, so start coding and tell us about that (when I applied, I sent an addendum to my application with a project I’d just started)!

Other than being a builder, we look for a few other things (listed below). You don’t need *all* of these things to get into hackNY (I didn’t have them!), but being strong in more than one area is important:

1. Strong coding and/or design ability. Chunks of code you write and/or things you’ve designed will be reviewed by people who are very good at what they do. If they think you’re good too, that’s a big plus.

2. Interest in the startup world. The majority of your summer will be spent working for an early stage startup. If that’s not something that you’re really excited about, hackNY probably isn’t for you. When we’re reviewing applications, we look for things that you’ve done in the past that convey this excitement. If you’ve founded your own company or worked at a startup already, talk about what you learned and why you want to do it again. If you haven’t, tell us about something you did something that felt like a startup and why you want to experience the real deal.

3. Good essays. An unbelievable number of applicants write unedited, seemingly thoughtless essays. If you write well-written, thoughtful, essays, you’ll get ++ by a bunch of the application readers (myself included). It shows that: (a) you can write, which is a great skill; (b) you care enough to put the time and energy into making your application great. Don’t bore us with 1000 word essays, but make sure that you put serious time and thought into them.

4. Online presence. I almost put this one in the next category, but decided to put it here for one reason: if we Google your name and nothing comes up, that’s almost always a negative for you. Make sure that we can find information about you with a simple search. For me, it’s one of the first things that I do. If you write a blog or have other cool stuff come up, that’s a big plus. If we see your Github profile and other accounts, that’s good. If there’s nothing, even when we Google “your name + your school” that’s not good. Obviously, if you have a super popular name then don’t worry about it.

There are some other things that we look at but are not that important (we don’t even ask about them specifically on the application):

1. Past internships.  I was one of two first-years in hackNY. Some other fellows hadn’t had previous internship experience. It’s a nice thing to have, but definitely not mandatory. If you’ve worked at cool companies, tell us what you learned in your experiences. If you haven’t, don’t worry about it!

2. School and grades. There’s a reason I put this one last, it’s really not important. If you have a 4.0 at a top CS or design school, it helps. If you have “bad grades” or went to a “bad school” though, we don’t care. Grades are a horrible marker of success in an environment like hackNY, but if you have it, that’s great. If you don’t, definitely don’t worry about it.


What did I do to stand out from other applicants?

To be honest, I was actually at the bottom of the selected applicants, so I almost didn’t make it. After talking to application readers that year, I learned that this primarily had to do with the fact that I was a first-year in college and had only started coding at the beginning of the year.

With those things stacked against me, I was told that I did a few things which led to my acceptance (all following the things above).

1. Even though I’d started coding months before I applied, I already had a few projects that I’d built and were publicly available. The first web application I ever built was one for my college and it already had a 1000+ users who actively used it when I applied. The second web app I built (the one I sent the addendum about) didn’t see the same success, but it was a much greater undertaking where I’d learned a lot (which I could talk about). The second one was also more startup-y, so I think that showed a demonstrated interest in the startup community.

2. I spent a lot of time on my essays (and I think they were good). A surprisingly large number of people put little to no effort into these essays. If you’re already a badass hacker with a bajillion cool projects, that might be OK. If you’re a relative beginner like me, the quality of these essays is going to be really important to your acceptance.

3.  I went to a small liberal arts school in California whereas most other students went to engineering schools on the East Coast. hackNY aims for diversity of every type in the program, so I’m fairly confident this helped me a tiny bit. If you go to a school like Pomona, definitely appy!

4. Luck! There’s always a little luck in getting into hackNY (or any other competitive program like this). There are *so* many qualified candidates, and we can’t let everyone in, so we end up saying no to a lot of good people.

If you’re thinking about applying to hackNY, you absolutely should. The summer I spent with hackNY (and BuzzFeed) was one of the best summers of my life. I learned an unbelievable amount about technology and startups, made friends that I’ll have forever, and had more fun than I could have imagined.

If you have any other questions about applying (or your specific application), don’t hesitate to tweet at me or email me