January 22, 2018

How Not to Sabotage Yourself as a Young Non-Conformist

Last Updated: January 22, 2018

We will update this document with new tips and links to Ask 1517 posts giving detailed examples and insight on social behavior in Silicon Valley and startups in general.

This culture guide outlines some habits and behaviors that will help you handle various social interactions. We realize that not everyone you meet will abide by this guide. There will always be jerks and exceptions. However, we think these tips will by and large keep you from making an ass of yourself.

With any social interaction, there are second- and third-order reputational consequences that you should remain conscious of until you have internalized a set of manners that will help you get what you want in the long run.

“To flee as much as possible affectation; and, perhaps to coin a word, to make use in all things of a certain sprezzatura, which conceals art and presents everything said and done as something brought about without any effort and almost without giving it any thought.” — Castiglione, Book of the Courtier 1524

It’s important to emphasize that this is not about socially irrelevant information, or even irrational conventions, but about helping you get what you want. As you will be spending a lot of time in conversations with strangers, trust on both sides will take time to establish. But trust is integral to anything you want to accomplish. Hence manners and mores.

A hundred years ago banks built heavy august buildings with high ceilings full of grandeur and majesty to signal that they wouldn’t run off with your money. Being the founder of a startup, you should tend to act the same since people are entrusting you with their money and careers.

As a member of the startup community we expect you to act with leadership and integrity, but this is also part of being an adult and having your shit together. For anyone, these traits are important. However, for our community — younger people that we expect to become leaders of consequence — these traits are critical.

What to wear to meetings & conferences:

  • Everyone loves eccentricity and a rock star veneer (we took a meeting recently with someone in a Jurassic Park t-shirt who is working on biotech — love it, it’s quirky, fun, and on point), but do spend a modicum of thought considering whether your apparel might insult someone you’re meeting. T-shirts with slang or offensive propaganda might put people off, and since you might be younger than twenty-one, shirts advertising alcohol and drugs will call attention to yourself.
  • A few style tips for more formal business meetings: if you wear dark pants and dark shoes, don’t wear white socks. Your belt should match your shoes. Don’t know what to wear? Smart Casual is a safe bet. You can ditch the jacket if you get somewhere and it’s too dressy. Good posture and a smile go well with everything.

What is the best way to handle arriving late to a meeting or event?

  • It’s important to be respectful and responsible about being late. Time is a scarce non-renewable resource, so do your best to arrive early, if not on time, to meetings and events. Years ago, people in Silicon Valley coined the term “big timing” to describe others who chronically show up late. “Where’s Dennis?” “Oh, he’s big timing us.” You do not want to become known as someone who big times others, especially when you’re small time.

If you are running late, we recommend the following:

  • Informing the person who is waiting for you as soon as you know that you will be late is best. This gives them time to plan accordingly. Send a text, send an email, use the phone. Do something — and don’t wait 2 minutes before the start time.
  • Once you have arrived, an apology or words of gratitude are appreciated.
  • The best types of apologies take responsibility for your actions. For example, instead of blaming the external world — “I hit traffic” — it comes off much better to accept responsibility yourself. Say something like, “Thanks for waiting. I didn’t plan my time well this morning to anticipate for traffic.”

If I have accepted an invitation but then decided I’m not interested in going, what should I do?

  • Pretty much the same as above. If you know you won’t be attending an event that you have promised to go to, let the host know as soon as possible. Especially for smaller community events, if we anticipate a group of people to arrive, we’ll often postpone our event and wait for your arrival. But if we know that you’re not coming on time we can start without you.
  • If you don’t attend and do not let the host know that day, you should send a note as soon as possible admitting your faults and expressing responsibility. Again, think in terms of apologies and gratitude. They work wonders in maintaining relationships and showing that you can be responsible even when you’re announced intentions didn’t line up with your actions.

Do not stand out for the wrong reasons:

  • You will become “that guy.” (Or woman). A VC or an angel investor or even possible employees are constantly sizing you up. With good reason. They are taking a risk in joining you. They deal with other startups and employers and they have options. Do not give them a reason to reject you based on superficial stupidity or arrogance. Think about it. It is difficult to measure value. Because uncertainty clouds our initial judgment, we often rely on aspects of things that are known as a rough proxy for measuring the deeper quality that is unknown. Venture capitalists, employers, peers and others will scrutinize the way you present yourself because these surface qualities will act as a proxy for measuring the value of your project. No one wants to admit they judge a book by its cover, but the fact is they do.

Follow Up:

  • If you’ve met someone, follow up with an email saying how it was nice to have met them and how you look forward to seeing/working with them in the future.
  • Hand-written thank you notes are thoughtful and recipients are more likely to remember them. Since they take time and postage, save these for special thanks. At 1517, we love these so much that we put them on our wall as decor — -and we’ve got lots of them!

Meeting High Net Worth Individuals or Silicon Valley Greats:

  • Steve Jobs said there are those who ask and those who don’t. When he was a teenager, Jobs wanted to learn about frequency counters so he looked up Bob Hewlett (of Hewlett and Packard) in the phone book and called him. It worked. Most people can be found even today — either by email or at conferences — and they probably will respond. But know who your audience is and prepare for the meeting. Unfortunately you will always have to be on. This isn’t an opportunity to give your guru a behind the scenes glimpse of your efforts and troubles. Instead, it’s best to always think of it as a bona fide pitch meeting. If you come across as incompetent or disorganized, even if a rabid fan, then that impression may always stay with you.

Email: “My inbox is a game of Tetris I’m about to lose and I don’t know what to do!”

  • Some may recommend ignoring emails to concentrate on an important task or outright declaring email bankruptcy — we generally don’t recommend this tactic, especially this early in your careers. Once you’re big time it may be okay.
  • If you know that you’re on a tight deadline and can’t get back to emails, make an autoresponse to let people know this. If another medium, such as a phone call, is better for you during these crunch times, consider leaving your phone number in the autoresponse for those who urgently want to reach you.
  • Again, using gratitude works wonders here as well “Thank you for contacting me, however I’m currently working on X and am not checking email regularly. If your request is urgent, please call me at _____.”
  • If you don’t use an auto-response and respond to someone very late on a request — thank them.

“In a discussion, what if I know someone is wrong on the facts?”

  • No one likes a know-it-all even if they’re right. Show some epistemic humility and agree to disagree. State your case once, maybe twice, and leave it there.
  • Understand that the purpose of argument in most social settings is not to discover the truth, but to assert higher status and build coalitions. Arguments are best when all the participants have a stake in the outcome. This is rare at parties or at lunch.
  • Keep in mind there’s a difference between discussion and argument. In a discussion you’re more interested in understanding where the other person is coming from rather than presenting an argument so powerful that your opponent’s head will explode if they do not accept its truth. In a friendly discussion you might find yourself inquiring into the person’s thought-process as much as possible: more questions and less outright opinion. Listen more, talk less. Argument is conflict.
  • If a person keeps repeating the same argument it likely means their emotions are driving their reasoning, so you might try to say something like, “So what I think you’re saying is….” to ensure that you’re both on the same page. Different opinions are great, we all shouldn’t think alike, just know that it’s all about how you communicate. You may have a mind-blowing, world changing insight into the nature of things, but if people walk away from the conversation feeling like you’re a blowhard you might as well toss your thought down the memory hole and blame your reptilian hindbrain.

“Someone is driving me nuts. Is it ok to be a public hater? Can I gossip or talk badly about them? Can I post about it on social media?”

  • If someone is being a jerk, ignore and avoid them. The key virtue here is breezy indifference.
  • Gossip may win you a few laughs in the short run, but since this is coming at someone else’s expense, be prepared to own the dirt you’ve unearthed.
  • Know that this disrespect and slander may reflect poorly on the speaker since it is negative and degrading of others. It may also leave your listener wondering if you talk like that about them. If you do need to talk about a person and a problem you’re having, take it to the appropriate parties instead of spreading rumors. Conflict is emotionally difficult, but informative.
  • Learn the art of discretion.
  • Social media? Hell no.

“I have a complaint about a company, a community, or somewhere I’m an employee, what’s the best way to handle it?”

  • The best way to handle a complaint is to go directly to the source. Once you have employees this will become very, very important. Do not let rumors coalesce into bad morale. By talking directly with the parties involved, we can find a way to resolve it or clear up any miscommunication. Blowing off steam to others may be great for venting but it’s not great for getting what you want.
  • You should have no fears about expressing dissatisfaction to any one. The best organizations appreciate the feedback and hope to improve your experience in light of it.
  • Never be afraid of immediately making a scene if behavior is boorish.

“Who pays for coffee/tea/hot beverage at a meeting?”

  • If you are the one who set up the meeting it is in your best interest to offer paying for the coffee/meal. People are quite generous with younger people, though don’t assume that someone else is paying for you. Consider going on a walking meeting — they’re great if it’s for an intro and everyone gets the bonus of some fresh air and exercise.

Use of electronic devices at meetings:

  • Generally it is best not to check phone/texts/email while meeting with someone — especially one-on-one. You want the other person to be the center of your attention — and for them to know it (which means also keeping your phone away and not on the table)! The golden rule is good here: do unto others as you would have them do unto you.

How to excuse yourself from a non-productive meeting or networking event:

  • Have a reason on hand for why you’re leaving. It’s best to announce upfront if you know you have a time constraint. It doesn’t have to be all that important, only real: “I’m sorry I have to go. I have a lot of work to get to today.”
  • If you’re meeting with someone and you realize that they’re not a good fit for you — like a bad first date — you can end a conversation by saying, “So what’s next for you today?” This starts to close out the conversation because you can easily segue into what you need to leave for. If you’re confronted with this at a networking event it’s usually easy to slip away once someone else in the group picks up the conversation.

How to politely decline invitations:

  • Express gratitude for the offer and the reason why you can’t come. Silence is not a professional way to decline an invite.


  • Showers are good. Baths are okay. Take one or the other at least every other day. Offices are not hackathons! Walgreens sells affordable soaps and fragrances (But for the love of all that is holy, please go sparingly on these things too — you want a hint of fragrance not a dump truck of wafting scent). Putting a comb or hand through your hair and washing your face works wonders to prepare you for the land of the living. Wash your clothes from time to time, too.

How to best schedule a meeting:

  • Pony up and suggest a specific time to meet. Maybe three or four alternatives, tops. Don’t play the passive ping pong game of trying to be nice by not asking for a specific place or time. Too much email ping pong involves each side saying, “What’s good for you?” and “I don’t know, what’s good for you?” Make firm requests in the first email. “Hey Susan, I’d love to meet about X if you have time and are interested. If you are available, would Tuesday at 6pm at Galvanize work for you?” This makes scheduling easy and efficient.
  • Don’t be pushy about getting a meeting. It’s unbecoming and you’ll come off like a jerk — and tone deaf to boot. Sometimes meeting (much like dating) isn’t a fit, don’t take it personally.
  • When you request a meeting of someone, you’re asking for their time. If they are particularly busy and offer you something that they have, but isn’t optimal for you, just take the damn meeting! We’ve actually heard, “Can we meet later? I sleep in” when we try to make it work (who say they’d like to meet urgently) and are booked otherwise. That’s like asking someone for a favor and then getting nitpicky about it. If you can’t wake up through a normal alarm, get one of these — Michael slept in a bed at a hacker house once (thanks Shift in Michigan!!) and he thought that an earthquake was waking him up.

Dating your co-workers/co-founders:

  • Not recommended, fraught with peril. Inevitably you break up and it’s an emotional minefield in your workplace. Not to mention that this could bias your decision making and corrupt you by playing favorites. Sexual harassment is always on the horizon as well. Headlines attest to the stupidity in the workplace. Best to avoid these problems altogether. There are plenty of fish in the other seas.

Should I cofound a company with my girlfriend/boyfriend/family member/or friends?

  • This can be a tough dilemma. Perhaps you came up with the idea together. Maybe the moral support would be good. Since you get along so well in your relationship, you think you’d work well together too. It’s important to remember that startups are extremely demanding on your time and will power. Roles are fluid and develop in a chaotic environment. Problems invariably arise and elephants in the room tend to accumulate when we think we will ruin our social relationships by having uncomfortable business discussions with family members or loved ones. Instead of dealing with problems early, our kindness causes problems to fester or blow up.
  • If you co-found with a family member or loved one, you have to have a pre-nup. Think about public ways to resolve disputes in advance. You may even want a failsafe plan that stipulates what happens in the event of an epic business conflagration.
  • Then again, there’s always Paul Graham and Jessica Livingston.

The number one rule to conventions is that there are always exceptions and context matters. After hearing the pitch to invest in Apple from Jobs and Wozniak, Mike Markkula — their angel investor — said, “They were bearded and they dressed funny and they didn’t smell too good.” Don Valentine of Sequoia followed up, “Why did you send me this renegade from the human race?”