If this is your first time reading, I recommend you start with my 6-month challenge and table of contents of weekly posts for the past 16 weeks.
tl;dr This is a more introspective post than usual and me trying to take a step back to look at the forest, rather than the trees of a tunnel-vision startup. I discuss having shipped Cusoy, fear of failure and fear of success, revenue concerns, importance of cities and ambition, developing relationships in your 20’s and fear of missing out.
The way I write these blog posts is somewhat haphazard and loosely fleshed out from a quick outline that I conjure in my mind minutes before I start writing. I wish I had a regular blogging schedule but a lot of this is stream-of-consciousness, as my emotions run the rollercoaster gamut almost every single day.
II. Fear of failure and fear of success
III. Revenue concerns
IV. Cities and ambition
V. Relationships and FOMO
Running a startup is like walking on your hands: it’s possible, but it requires extraordinary effort. If an ordinary employee were asked to do the things a startup founder has to, he’d be very indignant. Imagine if you were hired at some big company, and in addition to writing software ten times faster than you’d ever had to before, they expected you to answer support calls, administer the servers, design the web site, cold-call customers, find the company office space, and go out and get everyone lunch.
And to do all this not in the calm, womb-like atmosphere of a big company, but against a backdrop of constant disasters. That’s the part that really demands determination. In a startup, there’s always some disaster happening. So if you’re the least bit inclined to find an excuse to quit, there’s always one right there.
But if you lack commitment, chances are it will have been hurting you long before you actually quit. Everyone who deals with startups knows how important commitment is, so if they sense you’re ambivalent, they won’t give you much attention. If you lack commitment, you’ll just find that for some mysterious reason good things happen to your competitors but not to you. If you lack commitment, it will seem to you that you’re unlucky.
Whereas if you’re determined to stick around, people will pay attention to you, because odds are they’ll have to deal with you later. You’re a local, not just a tourist, so everyone has to come to terms with you.
– Paul Graham, The Hardest Lessons for Startups to Learn
Well, it only took me 2-3 weeks longer than I expected to ship Cusoy! I had tried to squeeze in this milestone by the time I wrote my Monthly Review #3, but alas, it was not meant to be.
One of the things I learned about myself — actually, one of the things I already knew about myself but still continue to see it manifest daily — is that I work like a sprinter, whereas a startup is a marathon fit for a long-distance runner. So I work like crazy for a sprint and then get really burned out afterwards and have to have mental and emotional health days and relaxation to recuperate. It’s not right or wrong, but I wish I’m more like a tortoise than a hare; slow and steady wins the race and doesn’t end up burned out.
I shipped Cusoy last week and have been somewhat distracted by some things this week, and also with the impending headaches of everything that comes with a soft launch. I’ve been putting them off but am finally getting back into things tonight.
As I mentioned earlier, product launches simply signal the first inning of the game, but if you don’t pace yourself, it’s really easy to get overwhelmed and burned out:
Funding Announcements and New Product Launches.
What do these two things have in common?
With each the work really starts after you put the news out there.
When you announce funding that’s when expectations are really put into place. You need to live up to whatever valuation you are getting.
Same with new product launches. Now you finally see how people use your product or service and adjust/add/subtract accordingly.
That’s the funny thing about working at startups or on products. While outsiders may think the end game is getting that article about your new funding or product release, the truth of the matter is that it is only the first inning.
– Alex Taub, The First Inning
After shipping, I gave myself some days off as mental and emotional health days and to catch up with friends — I find socializing as a terrific way to recuperate from feeling burned out from working alone on Cusoy.
Fear of failure, fear of success, crisis of confidence
People seem impressed that I was able to even ship Cusoy to begin with, since I’m just some-crazy-irrational-unknown-lowly-young-early-20-something-budding-product-manager-with-no-technical-skills-no-engineering-background-no-MBA-living-off-my-own-savings-working-by-myself-founder (wow, this is getting to be a mouthful)… I just smile and nod but inwardly cringe and wince, because I’m just scared of how things will turn out into a spectacular crash of failure, an impending trainwreck that is coming any second.
I feel like an impostor. Almost all the time.
Even as I write this, I hesitate to write… because a part of me feels like I should man up and suck it up like everyone else. What are you doing? An “impostor”? What the hell? Stop complaining. Stop whining. Shut up and get back to work. You haven’t experienced anything yet — no bankruptcy, no cofounder leaving you at the last minute etc, no “real” problems — you phony fraud. If you can’t deal right now, how do you expect to succeed?
…It’s hard dealing with my mind sometimes. But I find that writing helps clear my mind and clarify my emotions, and for posterity’s sake, these posts are amazing to read and reflect back upon when I reread them later on.
It’s a somewhat chaotic and unexplainable mix of optimism and pessimism, if you will. I see myself as an underdog trying to overcome the huge odds stacked against me and am optimistic I can make a dent to some degree, but pessimistic when trying to see things long term in an effort to grasp at nonexistent sureties and certainties.
I’m always used to knowing what’s ahead of me, predicting the future and how to best prepare for it. Founding a startup (I hesitate to say “company” because I have not generated any revenue) is both exciting and scary as hell in the fact that I have absolutely no idea what’s going to happen. It’s an odd feeling, since I have been entrepreneurial in recent past years, but always because I knew my ideal results and how things could turn out, with Plans B, C, D lined up should anything go awry.
With Cusoy, it’s just a black hole of possibility — a glass half full or half empty kind of black hole of possibility.
II. FEAR OF FAILURE AND FEAR OF SUCCESS
One of the things I’ve noticed is that I have an intense fear of failure but also fear of success… which leads to a daily crisis of confidence at times.
Fear of failure
Fear of failure is easy to understand and can be easily “rationalized away” in such examples as:
- There’s no better time to do a startup — both in a macro trend sense and a personal sense
- I’m young and can afford to take risks
- I don’t have any prior obligations like a family/mortgage payments/college loan debt, etc
- I have 8+ months of runway due to watching my cash flow like a hawk
- I can always go back to work for a tech startup/company
- This whole journey is still relevant experience as a product manager
- Startup failure is almost looked upon as a badge of honor in Silicon Valley
… but most of all, when I look deeper into myself:
On a fundamental, basic personal principle… This is what I’ve always wanted to do. This is the “what” and “why” of everything I’ve done in my entire life, leading up to this moment. This is what I was born to do.
I embrace challenges, I don’t run away from them. This is what makes me happy, not some 9-5 desk job working for corporate America. I don’t want to live with regret when I’m 80 on my deathbed. (I honestly think I’m wired to be an entrepreneur, for better or for worse, if that makes any sense.)
With that said, it seems easy to “reason away” the fear of failure. And yet, I’m still scared as hell.
I’m not impressed at all by myself, to be honest. It’s more of, OK, you got to this milestone. Whatever. You have my permission to pat yourself on the back. But don’t you dare slack off yet. What’s next? Let’s see where you’ll be in six months. If your startup is dead by then, all of this is meaningless and you just completely wasted your time and life. A lot of fear and irrational thoughts.
And this is something I have to keep reminding myself, that you only see the highlights reels of others in how they’re doing, yet you always see the failures of yourself on a daily in-your-face basis. It’s like Facebook and a major reason why I loathe it — you always see your friends and acquaintances in the best possible light — smiling next to their significant other, laying on the beach in Bali, teaching abroad in beautiful France, partying in Vegas, directing a documentary in South Korea, skiing in Aspen, having the time of their lives… and think to yourself, wow, I wish I were them. And what am I doing with my life? I feel like a loser for doing this crazy startup.
But you have absolutely no idea what they’re going through, any problems they’re struggling with, etc. You just see their successes, and by relative comparison, your own personal failures.
Do you really think people will be trumpeting their problems with depression, alcoholism/drug problems, marital problems, relationship issues, health problems, workplace issues, (insert your own problem/issue) etc. on full display on Facebook?
Fear of success
Fear of success is another beast. A lot of people, once they overcome a seemingly insurmountable barrier, shrug it off as pure dumb luck and chance as a veneer for deeper fears of success — for example, when I received my internship and job offers, both in finance and tech, I experienced acute episodes of fear of success that were self-sabotaging. This also goes hand in hand with impostor syndrome. I often felt that I didn’t deserve it and was scared that I wouldn’t be able to fulfill my new responsibilities and was inadequate, insecure and a fraud.
Again, a lot of fear and irrational thoughts coming at you from both directions of failure and success.
In this case, I have fear of success with Cusoy because I know I don’t have all the answers to all the questions and so forth.
III. REVENUE CONCERNS
I won’t go too much into it here, but just refer back to my previous blog posts during Week #14 and Week #16 where I go into a stream-of-consciousness rant in how this past month in particular, I became especially jaded on B2C startups not being profitable.
I’ve always known the business model to be very important (obviously), but didn’t feel it this acutely until this month, when it seemed like a lot of B2C startups were shutting down left and right seemingly from product-market fit / profitability / runway / revenue issues, while Snapchat and Pinterest were receiving bubble-like valuations while not making money at all or not profitable (and congrats Twitter on a successful IPO with shares up 73% the first day despite not being profitable).
IV. CITIES AND AMBITION
One of my favorite essays from Paul Graham is titled Cities and Ambition.
I’m quoting select excerpts below in chronological order of my greatest takeaways and favorite nuggets (without diving specifically into different cities and their personalities):
Great cities attract ambitious people. You can sense it when you walk around one. In a hundred subtle ways, the city sends you a message: you could do more; you should try harder.
I’ve always either considered living in San Francisco and New York for these reasons alone.
How much does it matter what message a city sends? Empirically, the answer seems to be: a lot. You might think that if you had enough strength of mind to do great things, you’d be able to transcend your environment. Where you live should make at most a couple percent difference. But if you look at the historical evidence, it seems to matter more than that. Most people who did great things were clumped together in a few places where that sort of thing was done at the time.
You can see how powerful cities are from something I wrote about earlier: the case of the Milanese Leonardo. Practically every fifteenth century Italian painter you’ve heard of was from Florence, even though Milan was just as big. People in Florence weren’t genetically different, so you have to assume there was someone born in Milan with as much natural ability as Leonardo. What happened to him?
If even someone with the same natural ability as Leonardo couldn’t beat the force of environment, do you suppose you can?
I don’t. I’m fairly stubborn, but I wouldn’t try to fight this force. I’d rather use it. So I’ve thought a lot about where to live.
Living in the San Francisco Bay Area is the best place to be if you want to be in tech startups. Bar none. Sure, you can found your own startup elsewhere and it’s not impossible to succeed, but hands down there is no better place in the world to be than here. There are other great thriving tech scenes in New York, LA, Austin, etc. but they are of varying degrees and at the end of the day, still are not the same as Silicon Valley.
Before there is a massive uproar about this — I’d like to point out this is true for any “nexus” of a sort. For example, New York is finance. LA is entertainment/movies. Houston is oil/gas. DC is nonprofits/law/government. This is not new.
If you’re an up-and-coming actress, it’s going to be a helluva lot harder to break into a major motion picture if you’re in St. Louis than if you’re in LA, for instance.
In tech’s case, everyone knows Silicon Valley is the premier place to be.
No matter how determined you are, it’s hard not to be influenced by the people around you. It’s not so much that you do whatever a city expects of you, but that you get discouraged when no one around you cares about the same things you do.
There’s an imbalance between encouragement and discouragement like that between gaining and losing money. Most people overvalue negative amounts of money: they’ll work much harder to avoid losing a dollar than to gain one. Similarly, though there are plenty of people strong enough to resist doing something just because that’s what one is supposed to do where they happen to be, there are few strong enough to keep working on something no one around them cares about.
Because ambitions are to some extent incompatible and admiration is a zero-sum game, each city tends to focus on one type of ambition. The reason Cambridge is the intellectual capital is not just that there’s a concentration of smart people there, but that there’s nothing else people there care about more. Professors in New York and the Bay area are second class citizens—till they start hedge funds or startups respectively.
“It’s not so much that you do whatever a city expects of you, but that you get discouraged when no one around you cares about the same things you do.”
Quality and caliber of people who care about the same things I care about has always been the #1 factor for me in terms of where I’ve decided to live. Costs of living, taxes, weather, etc. are secondary in my book.
This is also why I don’t want to move back home in DC to live in my parents’ basement to save expenses, because the environment and things people care about in DC are just so incredibly different on so many levels versus here in Silicon Valley.
Does anyone who wants to do great work have to live in a great city? No; all great cities inspire some sort of ambition, but they aren’t the only places that do. For some kinds of work, all you need is a handful of talented colleagues.
What cities provide is an audience, and a funnel for peers. These aren’t so critical in something like math or physics, where no audience matters except your peers, and judging ability is sufficiently straightforward that hiring and admissions committees can do it reliably. In a field like math or physics all you need is a department with the right colleagues in it. It could be anywhere—in Los Alamos, New Mexico, for example.
It’s in fields like the arts or writing or technology that the larger environment matters. In these the best practitioners aren’t conveniently collected in a few top university departments and research labs—partly because talent is harder to judge, and partly because people pay for these things, so one doesn’t need to rely on teaching or research funding to support oneself. It’s in these more chaotic fields that it helps most to be in a great city: you need the encouragement of feeling that people around you care about the kind of work you do, and since you have to find peers for yourself, you need the much larger intake mechanism of a great city.
You don’t have to live in a great city your whole life to benefit from it. The critical years seem to be the early and middle ones of your career. Clearly you don’t have to grow up in a great city. Nor does it seem to matter if you go to college in one. To most college students a world of a few thousand people seems big enough. Plus in college you don’t yet have to face the hardest kind of work—discovering new problems to solve.
It’s when you move on to the next and much harder step that it helps most to be in a place where you can find peers and encouragement. You seem to be able to leave, if you want, once you’ve found both. The Impressionists show the typical pattern: they were born all over France (Pissarro was born in the Carribbean) and died all over France, but what defined them were the years they spent together in Paris.
My point in having a section devoted to cities and ambition… is not to denigrate anyone living elsewhere, but a word on why I moved here and how I still am not in the exact physical place I want to be.
I am extremely grateful and thankful that I am in the heart of tech in the entire world, in Silicon Valley. I am minutes away from some of the world’s top companies — Facebook, Google, Apple, etc. I am surrounded by like-minded, incredibly talented and intelligent individuals working on amazing products and teams. Not to mention I absolutely love northern California and its weather and various getaways — Tahoe, Santa Cruz, Monterey, Vegas, Napa Valley, Yosemite, etc.
At the same time, I often lament the fact that I’m actually not in San Francisco, but in the Peninsula (Bay Area) since it was closer to work (Evernote in Redwood City) and cheaper in the sense that I’m uncomfortable with the requirement of dedicating 60% or so of my paycheck to paying rent in the city. It’s cheaper for me to bootstrap here in the Peninsula but it often gets lonely as most of the activity and peers my age either are in San Francisco or Palo Alto (I find Palo Alto very similar to my hometown and rather boring); I have a feeling in the back of my mind that I am missing prime chances to develop relationships in these critical times of my life when trying to bootstrap my startup.
One of my goals next year is to move to San Francisco… once I can afford it, for at least 6 months anyways. At my current runway and burn rate, things would immediately be halved and look a lot more dire if I moved to the city. Ha.
Developing relationships and fear of missing out (FOMO) are other reasons why I wanted to mention the importance of cities and their ambitions. They’re also extremely important, as even if you move to a prime location (San Francisco, NYC, LA, Chicago, etc) — if you don’t have strong relationships or proactively meet new people, the mere relocation won’t have much added benefit to your life.
V. RELATIONSHIPS AND FOMO
You’ve probably heard this before: You are the average of your 5 closest friends.
(If you haven’t, I’d advise you to take it deeply to heart, because it is so true.)
Who are your 5 closest friends?
We can take it out even more, in no particular order:
- Your salary is the average of your 5 closest friends.
- Your positivity is the average of your 5 closest friends.
- Your personal growth is the average of your 5 closest friends.
- Your professional growth is the average of your 5 closest friends.
- Your worldview is the average of your 5 closest friends.
- Your ambition is the average of your 5 closest friends.
- Your _____ is the average of your 5 closest friends.
Moreover, it’s been said over and over and over —
- If you are associating with people who are closer to who you want to be, you will accelerate your growth.
- If you hang out with people who bring you down, you will fail.
You’ve also probably heard this before: If you’re the smartest person in the room, you’re in the wrong room.
It’s something I think about a lot. Who are my friends and am I mostly learning from them or teaching them? It’s kind of a harsh, cold way to look at relationships, seemingly almost transactional to a degree, since I believe everyone has worthwhile things to offer — but you have to be selective and reflective for your own sake.
This is a generic example, but if you have childhood friends who are in dead-end jobs, have drug problems, live with their parents… versus someone who is successful in X, Y, Z (again, this is very subjective and depends on your own definition of success), etc — who is going to help you become a better person and reach your goals?
A lot of people are impressed by prestigious degrees from Harvard, Yale, Princeton etc — and I used to be one of those people — but now I am profoundly impressed by someone who has founded or cofounded a successful company, traveled the world, is living life on his or her own terms, works for him or herself, etc.
Your definition of being “impressed” by someone may be something else.
It doesn’t matter what your definition of success is… but the key thing here is to have your own definition of success, whatever it is, to work towards.
I gravitate towards people who I feel I can learn from, people who challenge me, people who are successful in founding their own startups into a successful business or exit (my ultimate goal). I admire people like Ramit Sethi and Tim Ferriss and self-made entrepreneurs who run successful businesses built on recurring revenues and can live comfortably while helping others.
I also tend to gravitate towards people who love music, enjoy design, actively work out and care about health/fitness (eat well, not junk food), are passionate about education and spend their money more on experiences (especially travel) and amazing memories rather than materialistic possessions. These are just a few topics and areas that I would love to be enriched by my friends.
This is why I want to move to San Francisco and out of the Peninsula. I want to spontaneously and serendipitously meet others who are similar to me in my ambitions and goals — so that we can help each other accomplish our goals.
A part of me regrets not working for a big company like Google, Facebook or LinkedIn — simply because I would meet so many others my age and make new friendships with likeminded peers on a much easier basis.
…I wrote a book review on The Defining Decade last year and one of my biggest takeaways is that your 20’s are incredibly formative and you should seize every opportunity to create new memories and form your relationships now — before you become established, settled down with a family, in your 30’s and so forth where you might not come across as many interactions. Your 20’s are when we have our most self-defining experiences and memories.
I’ve often thought about this and am scared I am missing out — this might be irrational, as I have made plenty of contacts when I made trips to SF twice last year and during my tenure at Evernote; for those who I reconnected with, it just simply took an email or two to set up a coffee, but it’s a lot harder for spontaneous interactions if you don’t live in very close proximity. At the same time, I suppose where I live now is a blessing and a curse, since I’m actually located halfway between San Francisco and Palo Alto (I hardly ever venture in East Bay or South Bay past Mountain View).
Aside from developing and strengthening relationships by moving to San Francisco, I also have a strong fear of missing out. Some of my friends are jet-setting off to London and Ireland for Thanksgiving, have season passes to Tahoe and are golfing every weekend. Sigh.
This FOMO isn’t so much the actual experiences (though that’s a big part of it too), but that I miss out on spending quality time with friends due to founding a startup.
That is my main fear… and it’s somewhat contradictory a la “the grass is always greener on the other side” mentality, since if I was in Tahoe, I’d probably be wishing I was working on my startup like others my age doing their own startups.
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