Selection Bias

Understanding selection bias is one of the most useful things I have learned as far as mental models goes. It’s one of those models that I’d consider a moderator in the sense that it helps prevent one from jumping to conclusions and addressing the wrong problem or a non-problem. Put simply, selection bias (in the […]

What Role Should Social Media Play in Your Career?

When it comes to amplifying your thoughts, few tools have ever been created as powerful as social media. People who were complete nobodies can, and often do, have more followers than the leaders of entire countries. Being a social media influencer is a dream job among young people today. You know the pitch. But if […]

False Negatives and False Positives

One of my favorite ways of thinking about the world is by asking, “what are false positives? What are false negatives?” This is particularly useful for thinking about opportunities with relation to my work.  False Negatives Some companies or trends are “false negatives,” meaning that an idea or product tried out at one time looks […]

Disguising Philosophy as Self-Help

Philosophy done well is self-help. Aristotle wrote about what it is like to live a good life. Aquinas asked what it takes to understand God and lead a life that honors the Divine. Nozick wrote on love and understanding the world around you. And self-help done well should be philosophical, at its core. That’s what […]

Some Ways to Think About Opportunities

One of the best sets of mental models you can build out is how to think about risk. Should you interview for a new job? Should you quit your job? Should you move across the country? Should you cash out your investments and go all in on your business. Without some tools for thinking about […]

How to Cold Email Venture Capitalists

I’m a venture capitalist in my day-to-day work. Specifically, I work for an early stage venture capital firm as a principal. This means I review a lot of deals and take the time to do phone calls with our inbound and referral opportunities. It also means I get a LOT of cold email. And I […]

Professional Phone Call Etiquette

A professional phone call is a meeting. It doesn’t carry as much seriousness as an in-person meeting (one of the reasons I suggest starting with it in Email Anybody and not just jumping right to a meeting). But you should still treat it with the seriousness of a meeting. Given that more people work remotely […]

Think of Your Career in Thirds; Or, The Carnegie Dictum

A friend recently emailed me this article by Mark Suster on when to learn in your career and when to earn in your career. This is an important question in general, but particularly important when thinking about joining a startup. Most startups fail and you should not assume that your startup equity will be a […]

Substance > Status

Substance carries a longer-term return than status when it comes to building your career and your resume. By that, I mean the substance of your work at a company matters more than the status of the company for your long-term career development. In other words, imagine you have the opportunity to take two jobs. The […]

Your Resume Should Be An Afterthought

Contrary to popular belief and what you’re taught in those mostly-bad career books written by the same box-checkers every year, your resume is a relatively minor part of the job-hunt process.  How many times have you seen this? Somebody decides they want to get a new job, so the first thing they do is rush […]

Always Double Opt-In Introductions

Always double opt-in your introductions. In other words, never introduce two people to each other without checking with both people first that they want to be introduced. Good introductions benefit everybody involved. The two parties who are introduced to each other gain by meeting each other (assuming they want to meet), you gain by being […]

19 Rules to Get Ahead in 2019

Professional development starts with personal development. These 19 rules focusing on health, wealth, and wisdom propel you forward in your career.

How to Make People FIGHT for the Chance to Work With You

In 2017, I got a job offer I never expected. A growing startup backed by some of my personal role models and rock stars in the Silicon Valley investing world wanted me to run business development and sales for them. Their company sold based on strong relationships and a good understanding of long-term needs and […]

Conversational Conversions: How to Use Your Email List to Create Value NOW

I’m a fan of email lists. Every business, nonprofit, and personal website should have a lead capture, a lead magnet, and a regularly-engaged email list. (I’ve written about this here.) That email list is a direct line to people interested in you, your skills, your business, your product, or your organization. It’s your way to […]

Remote Work: How to MAKE Your Boss Let You Work Remotely

Remote work is the gold standard for most people’s office jobs. Tim Ferriss has a whole section on it in The Four Hour Work Week. Dozens upon dozens upon dozens of blog posts have been written about doing it. And the Basecamp guys even wrote a whole book on why companies should be entirely remote. And […]

How to Find Great Career Coaches

I hate most people who call themselves “career coaches.” And I do some career coaching. I’ve spent thousands of hours of my career coaching people for interviews, job applications, networking, and how to change jobs. I work with private clients who want to change careers or get a promotion. I’ve seen the questions that people […]

How to Give Great Gifts

Being a good gift-giver is a high-leverage skill. It helps you make a positive impression on your professional contacts, strengthens your existing network, and makes special occasions with friends and family fun. And knowing how to give great gifts carries over from one job or career to the next. But honestly, I used to hate giving gifts. […]

GUEST POST: How to Send a Job Application Email and Actually Get Hired

I write about cold emailing to land new opportunities. A lot of the time. Taking the time to actually sit down and send a single, well-written email can be the difference between blasting out resumes and never hearing back and landing your dream job. Even when you see the best opportunity out there, you still […]

Always Take Job Interviews – Even When Working a Job You Like

I recently sat down with an old friend who told me about his situation at work. He feels guilty for wanting to take job interviews at other companies because he likes his current job. But he also thinks other jobs look interesting. He’s working a job he enjoys right now but he feels like the husband who […]