I quit my Wall Street job because I wanted to work at a tech startup — here's how I pulled it off

Coffee chats and tech events can be very helpful in your job search. (Author not pictured.) NEXTConf/Flickr

TL;DR — I was dissatisfied with my job on Wall Street, so I quit without another opportunity lined up. I wanted to work for an early-stage technology company, and spent the next few months immersing myself in the NYC startup scene.

Using the tips below, I was fortunate to land a role with a startup accelerator (Techstars). This led me to become the first employee at a startup in which they’d invested. I often get asked how I navigated this process, so I hope this post can serve as a tactical guide.

When beginning my job search, I set four goals for myself:

Regain and maintain physical and mental health Learn a new industry (technology startups) Learn about companies and find job opportunities Develop relationships and expand my network

Below, I’ll break down each of these goals in detail. Additionally, I made a Google Sheet of resources I found helpful. I’d love to hear any feedback on this post. You can find me on Twitter: @CantHardyWait.

1. Regain and maintain physical and mental health

When I was working on Wall Street, I severely neglected my mental and physical health. I rarely exercised, my diet was poor, and my stress levels were astronomical.

During my job search, I’d wake up and go to the gym first thing in the morning. I also began to dabble in morning meditation. I’m a creature of habit and found it energizing to develop a routine where I accomplished something as soon as I woke up. In doing these activities first thing in the morning, I was far less likely to make excuses and skip them. Restoring my mental and physical health laid a great foundation for pursuing the job search.

This post is not meant to be super “self-help”-y, but I firmly believe there is power in both (a) building habits and (b) making those habits unrelated to your search in order to preserve your sanity. It can be exercise, meditation, writing, reading, etc. Basically, find your happy place:

Note: None of the activities portrayed in this video are good ideas to do first thing in the morning…

2. Learn a new industry: technology startups

A large part of my startup job search was becoming conversant in tech. I had little tech industry knowledge, other than using apps on my iPhone.

Within the context of any job interview, you’ll be expected to have knowledge of the relevant tech vertical, if not the startup world generally. For someone starting with no knowledge, spending about an hour per day getting up to speed is a good target. I’d break up reading into News and Analysis.

News

Every day, I read StrictlyVC. It’s a TechCrunch newsletter by Connie Loizos, with an overview of funding, startup news, and great interviews.

My Google Sheet has other good news sources

Cool hack: Download Nuzzel, follow the Twitter accounts I recommend, see what they’re sharing.

Analysis

It’s important to know what’s happening, but even more important to know what it all ‘means’ in context. I highly recommend Stratechery by Ben Thompson  —  his analysis is unparalleled. He also has an excellent companion podcast, Exponent.

Other good resources for tech analysis.

3. Learn about companies & find job opportunities

Stay organized

Tracking your opportunities will make your search more manageable. You should make a simple ‘target companies’ list. I kept a Google Sheet that tracked the following:

People will forget what you said, people will forget what you did, but people will never forget how you made them feel. - Maya Angelou

This advice holds true in all walks of life, but is a particularly powerful thing to keep in mind during a job search. Building relationships and cultivating a network are major keys that can supercharge your job search.

Fortunately for you, people in tech tend to generously volunteer their time and insight to engage with folks interested in breaking in to the industry.

I broke down relationship development into the following:

TwitterEmail outreachIn-person meetingsTech Events

Twitter: your secret weapon

Twitter is really really important. If used correctly, it can 10x your chances of landing a great job in tech.

I was initially a huge Twitter skeptic. I thought it was a platform to post useless life updates and navel-gaze. Or another superficial channel to follow celebrities.

In reality, some of the best analysis I’ve read, deepest conversations I’ve had, and tightest relationships I’ve formed have happened on Twitter.

In the context of the job search, it’s an amazing tool to stay in the “flow” of tech news and analysis. More importantly, it’s a way to interact with operators, investors, and journalists . Many of these folks would never respond to your email, phone call, or stop to chat with you on the street — However (inexplicably) they’ll respond to tweets.

Twitter for novices: Start by using Twitter passively to consume content. Follow relevant tech people and absorb what’s going on. I’d start by following the accounts I mention here. Massive thanks to Adam Besvinickfor forwarding me a list of his favorite twitter follows. You can gain a ton of value by simply following relevant accounts. The next step is actually tweeting and interacting. The Google Sheet has a good guide for doing so.

Email outreach

You should assume that if you just email a “cold” job application, it will not get lifted off the resume pile. Given the current desirability of working in tech, companies have all of the hiring leverage. It sounds cliché, but you must stand out.

One such way to stand out is being referred to an opportunity or person you’re interested in connecting with via a “warm introduction.” This is where someone you know, writes an email vouching for you to someone you don’t know (but want to be connected with). It is a deep-seated tradition in tech.

I used email to connect with a broad group of people who I thought would be additive to my job search.

When asking for a warm intro, certain etiquette is expected. This is a good overview of rules for requesting an introduction to someone you’d like to meet. Here are 11 other tips:

Proofread. All. Of. Your. Emails. Nothing will torpedo your credibility more quickly than email typos. Prospective Employer: “If you can’t compose an important five sentence email without spelling or grammatical errors, how can I trust you to market or sell my product, or run my company’s finances?” Many people believe this. Mistakes will hurt you. When asking a favor from someone, your goal is to make their life (and fulfillment of the favor) as easy as possible. So when you ask for an intro, make sure the email that YOU send to THEM is forwardable. It should be a clean email (not a reply to a previous thread). It should include a few sentences on who you are, what you’re asking, and why. Interesting as it may be, don’t include your entire life’s history. Your description of yourself should be three–four sentences at most. People are busy. Profusely thank people who make introductions for you. When your connection provides you a warm intro, you (the requestor) should respond promptly — within a couple hours. When you respond, have a specific ask. People are inundated with, and loathe the open-ended: “We should get coffee sometime” Better to say something like “As [introducer] mentioned, I’m in the process of figuring out my next opportunity. Given your move to [Company Y] after your time in [Industry Z], it would be great to learn more about how you decided to make the move” When you respond, offer three specific times of day to meet, at “whatever location is most convenient” for the person you’ve been intro’d to. Throw in: “if none of those times work, happy to propose more.” Scheduling sucks, and your goal is to make this as frictionless as possible. Proofread all of your emails. Don’t be offended when people don’t respond. You can gently nudge with a follow-up, but be careful. Wait at least a week, and don’t be annoying. Use common sense, but err on the side of being patient. Proofread all of your emails. A good proofreading trick I learned was to read the draft of your email backwards, i.e. starting at the end and reading upwards to the beginning.

Meet people in real life (IRL) 

I recently looked back through my calendar. Over the course of my four-month networking bonanza, I had initial coffee chats with over 6️0 different people.

Not only were many of these folks immensely helpful to me in the immediate-term (for which I am hugely grateful!) — but I run across many of them professionally, keep in touch with a decent amount, and ended up becoming good personal friends with a few.

Rules for meeting people IRL:

Don’t be late. Seriously. Be five minutes early. To some people, there are few greater sins than disrespecting their time. Do your basic research. Look up the person on LinkedIn, and Google a bit about their company Have a list of a few questions you want to ask. You can ask them the generic advice of “how they got to their current role”, but better to have specific questions about their background and company. Even if it it’s not a formal interview assume all of these professional interactions are interviews. You never get a second chance to get a first impression. Again, you want people to want to help you. The more that you can establish a genuine connection with someone, the more likely you both will be to help each other. Goes without saying, but you shouldn’t be distracted or checking your phone during one of these such meetings.  Keep these meetings to 30 minutes. After 30 minutes has elapsed, tell the person you’re meeting with that you want to be conscious of their time and confirm they can continue chatting. Don’t be shy about asking them if they can think of anyone who might be helpful in your search. When the meeting concludes, thank them profusely, and ask how you can help them  —  even if you’re unsure that you can.  Write a gracious thank-you email that includes any follow-up items.

Tech events and meetups

In NYC, we’re fortunate to have a never-ending selection of nightly tech events. I made an effort to find events at least two nights per week to attend.

Gary’s Guide is my go-to resource for sourcing tech events. For those based in NYC, it’s the most complete weekly overview of the NYC tech ecosystem, period. Don’t let the retro formatting fool you.

Other good resources for finding tech events.

How to get the most out of tech events

Some people think that tech Meetups and events are a waste of time. Indeed, some even turn out to be so. I viewed each of them as pure option value. That is, there was no downside to going, and if I could make even one relevant connection, it would be totally worth it. Here are some good general rules to follow:

Consider yourself in a business setting. Don’t get too drunk or behave in an otherwise inappropriate manner. Seriously, it’s important. The tech world is very, VERY small. As Warren Buffett said: Your reputation takes 20 years to build and five minutes to destroy. I suggest ‘focused’ industry MeetUps (FinTech, AI, VR, etc.) as opposed to generic tech or startup MeetUps. If you’re not comfortable talking to innumerable random strangers for hours (I’m not), go in with a manageable goal. Talk to two new people. A very easy ice breaker is “Have you been to XYZ event before?” or “How did you hear about XYZ event?” Yes, it feels ridiculously socially awkward at first, but such is life. Cool Hack: at some point during the MeetUp, go up to and thank the organizers. First off, it’s good manners. Secondly, they are generally active members in the Tech community (They went through the trouble and effort of organizing a MeetUp for goodness sakes). They can likely help you. These events generally have a panel of speakers. Often after the panel discussion concludes, the audience, in unison, makes a mad dash toward the speakers to ask them questions one on one. Then a hopelessly long line begins to form. I generally refused to stand around waiting in these lines waiting to schmooze with the speakers. Better to find them on LinkedIn or Twitter afterwards, and reference that you saw them speak but didn’t have a chance to connect. In any social interaction at these events, don’t monopolize someone’s time. Similarly, be courteous if your time is being monopolized and you’d like to exit the conversation. You can always say “It would be great to continue this conversation some other time.” Again  —  this will feel socially awkward. Get over it. Don’t interject or blatantly interrupt people who are mid-conversation. It is understood that you are allowed to “saddle up” to an in-progress conversation. Wait for a natural break if you’re going to make a comment. If possible, identify people ahead of time you’d like to talk to I didn’t make myself business cards, but found it effective to simply connect with people on LinkedIn soon after I’d met them.

Thank you for checking out my post! The above represents one person’s experience (mine) so please evaluate it accordingly. Here’s a Google Sheet that lists many of the resources I’ve used. Please let me know what you think of this post, and if I can be helpful in your search! Twitter: @CantHardyWait.

Finally, a HUGE thank you to Bez, Tommy, Nikhil, Max, and Khe for reading various drafts of this and providing massively helpful feedback!