in Life Optimization

What I Wish I Knew When I Started My Job Hunt

After more than four months of the job hunt, I’m finally happily employed in a growth position at a small startup, just as I wished. It was a tumultuous ride, but a valuable one – it’s not often that you get to spend time sitting down with new smart people every week to get their help.  That said, when I started this journey I was going about it all wrong. Here’s what I wish I knew:

Online Applications are a Waste of Time

I started off checking all of the ‘cool tech’ job sites I knew – Linkedin postings, VC firm portfolios,, Hacker News jobs, Slack jobs, Product Hunt jobs, Growthhackers jobs,, and so forth. That introduced me to a whole lot of new companies and alerted me to job roles I wouldn’t have considered otherwise. I painstakingly tailored cover letters to the most appealing companies, sent off my applications, and – nothing happened.

Applying online is like adding your resume to the fat stack already on the hiring manager’s desk, except even worse, because they never even meet you and you’re a stranger from the internet. You’re essentially consigning yourself to obscurity by applying online.

Eventually I figured this out and used the posted jobs in order to prioritize my plan of attack. I’d target a company, browse Linkedin to find an introduction to someone at the company, and only after talking to someone in house would send in an application. That way, I’m either a referral who skips the resume pile entirely, or end up on the top with someone on the inside to vouch for me.

Networking is the Only Way to Go

If I did it all over again,  I’d start with my network rather than companies with openings. As the Bittorrent CMO told me, it should be more about which companies interest you within your network than which ones within your area have openings. I should have fleshed out my dream job first, and then aggressively networked in order to find connections with companies that matched that dream. Rather than trawling online postings, I’d meet with people in my network and ask them what companies they thought matched my wishlist and who they knew who could help.

It’s pretty easy in theory – just reach out to everyone you know in the industry and ask for a lunch or a quick phone call in order to get advice. I was consistently surprised with how responsive busy important people were to my young gun self. With few exceptions, a warm introduction will at least get you 15 minutes on the phone. Then it’s up to you to make the most of it.

Busy People Are Willing to Help

Once you know who you want to meet with, ask their contact in your network to connect you by email, not through Linkedin’s Introduction tool. I found that these invitations would often fall by the wayside, while the email inbox is just as easy and far more important. Tell your connection why you’d like to meet the person in question (“I’m interested in her job function and wanted to talk with her about how she got there” is simple enough), and let them do the rest. Usually they’ll acquiesce, you have a warm introduction, and now all have to do is find a time to meet. In person is best, but sometimes you’ll have to settle for a call.

Come prepared. Do research on the company and the person (Twitter is invaluable here) so that you can ask informed questions rather than easily Googlable ones. Treat them like a human, and show that they’re not just a means to an end. As my search wore on, I found myself asking more direct, specific questions here, rather than macro inquiries like where the market is going. How they ended up at this company and what they think you could do to do the same are more important.

Just make sure to end on an actionable note. Help them help you. Whether it’s another introduction, a referral, or feedback on how to approach the application, give them a next step. Then afterwards send them an email summarizing your notes and how you plan to execute their advice. This accomplishes a few things – it shows you paid attention, that you’re taking their advice, and as a reminder to do what you asked them to. Then connect on Linkedin and let sit. You’ve made an impression in person, tracked it in their inbox, and shouldn’t pester them any more until you have something new to say.

Cold Emails are Invaluable

Sometimes you don’t have any connections with the person, or your desired introducer doesn’t get back to you. At this point, don’t hesitate to pull out the cold email. This is another big thing I wish I had known – cold emails are far more powerful than any other job-related task you can do online. There were times when I had already been rejected online, but managed to get an interview anyways because I had emailed the CEO and he forwarded it to some lackey who then treated my application as an order from above. It shows daring, resourcefulness, and initiative. Done right, the cold email can do nothing but good for you.

To find their email, use This site was a godsend during my search and continues to be helpful. It tells you if a given email address is valid, which lets you guess email combinations until you find one that works. Oftentimes the big guys’ emails are nothing more that or (Sometimes Mailtester says that the domain does not accept verification, but most times I’ve found that my best guess works anyways, so don’t be dissuaded.)

As for the email itself, there are differing guides on this (Noah Kagan’s and Scott Britton’s are good starters) but for me, it’s got 3 parts: the hook introduction, your value proposition, and an action step. It should be as short as possible, with neat formatting.

I start cold emails with ‘You are’, which grabs anyone’s attention when personalized. You are an inspiration to me, I’ve enjoyed this blog post of yours, etc. Don’t lay it on too thick, but be sure to tie yourself to them in some way or another, be it through their work, a shared connection, or some other mutual hobby. If you’re bold, you can use the name of a mutual Linkedin connection without asking them for an intro first. (I’ll admit I did this when some contacts never got back to me, worked like a charm.)

Then explain why you’re emailing them. Why them in particular? What value do you bring to the table? The more specific your advice wanted is to them, the better. Most busy people get hundreds of ‘grab a coffee and pick your brain’ requests a day, so don’t be one of them. Ask for something specific, just like the actionable note from earlier. Your best case is an in person meeting, but an introduction or shunt to another lackey is also valuable.

With cold emails, it’s all about being a kindly brontosaurus: polite yet immovable. If they don’t respond within two weeks, send another email following up to make sure they got it. Gently push until you get a response – the worst that can happen is a ‘no’. Remember that these people don’t care about you – you’re a stranger from the internet. A cold email that shows why they should care coupled with gentle pressure remedies that, but only with persistence.

Track Progress Like It’s a Sales Funnel

Now you’re meeting with people regularly and slowly getting closer to a desired company, or a sense of one. Great! Now the trick is to keep track of it all. Much like a salesman, you are juggling many relationships relationships in different stages towards specific goals. You need a place to keep track of it all, and Salesforce isn’t going to be quite as helpful for you.

I kept track of all the company openings, warm connections, meetings, and weekly accomplishments in one big Google doc, but in retrospect I wish I had structured it more around people. Instead of a big list of company openings, it’d be better to have a short list of desired companies, with the people who could get you closer to them grouped underneath. Then you track where each person is in the cycle – emailed, met, or needs following up. Otherwise you might make moves towards a person only to have them fall through the cracks.

Ian Adams of the Senator Club was so dedicated that he built a special Excel file of his contacts, but whatever system works for you as long as nobody falls into the cracks. What’s important is that you don’t let people fall out of contact, even after you have already met with them. Nailing the follow up is as important as nailing the introduction. Let them know how things have moved forward since last you spoke, and how your advice was helpful. That way you’re nurturing an actual relationship, instead of a one-off meeting.

As it turns out, creating and nurturing real relationships are things I should be doing no matter how employed I am. There’s nothing about the end of the job hunt that means I should stop cold emailing people I admire to get their advice. Now I just need to come up with an ask more involved than ‘get me a job’…