Great career advice from @Jason

The below is some spot on advice from @Jason. Enjoy.


1/The most important piece of advice I can give folks starting out: BE GREAT AT AN IMPORTANT SKILL.

The important skills in the world right now include:

a. sales
b. coding
c. product design
d. growth
e. design
f. corporate storyteller


If you’re a product designer, stop binge-watching TV & read every book on UX. Learn to use every tool you find on the internet.

Many folks will tell you that the world is not a zero sum game, with one person not having to lose at the expense of another winning. This is simply not true, as in most startups there is a very limited number of seats and they go to the people who work the hardest and who have the most skill.

In your career you will find that life is a zero sum game: the winners get the prime positions and the person who comes in second place for that position is the first loser — not the second winner.


Don’t worry about your salary, just get enough money to live in a closet close to work. Focus on providing your CEO 10x the value of your contemporaries. Your CEO will notice you, eventually, and she will love you.

CEOs love people who work hard and who refine their skills faster than everyone else (see #2) because those people remind them of themselves. How the f@#4k do you think she got the CEO slot, by waiting in line? By random luck? No, she f@#$king took that slot.

If you’re taking your slot by working harder than everyone else and by refining your skills faster than everyone else she will notice it.


Great CEOs obsess over their high performers. They like to talk to them, they like to mentor them and they like to challenge them. Once you prove yourself, it’s time to reap the benefit of being a hard worker with massive skills and the ability to learn new ones.

Never leave work before she does, respond to her emails quickly and without excuses. Here are things to say to her when she gives you amazing responsibilities that will make her love and trust you more.

When your boss asks you to set up the sales department for your startup you say:

“I have never set up a sales department before, but I’m going to find three people who have and suck their brain dry after work. If you know anyone smart I can leverage let me know — if not, I’m off to the races.”

When your boss asks you to set up a blog and podcast for your startup you say:

“I’m on it.” Then you come back to her 24 hours later with a Google Doc and say:

“Here are links to the five best corporate sites I could find, ranked in order of how well I think they’re executed. On each one I listed the three best editorial devices they used. I also put together a list of the platforms they’re using and how often they have each published in the last 60 days. Based on all of this I’d suggest we use Squarespace or WordPress, SoundCloud or this podcast plug-in. We should publish a blog twice a week and spend 2x as much time promoting it as we did writing it. By my estimate this will cost us 20 hours a week of editorial time and 50 hours of setup time. At $25 an hour fully baked it’s a $30,000 year one expense, so if we land three clients for our average enterprise software subscription we break even — at a 20-month LTV, of course.”

Here’s how most folks answer that:

“I’ve never set up a blog.”


“Can you just tell me what to do?”


“I wasn’t hired to do this.”

I can go for hours on how most folks answer these challenges and then never follow up, forcing their boss to chase them: “How’s that blog and podcast project going?”

There are two types of people in this world: killers and the killed.

You can move yourself from the killed bucket to the killers bucket by ‘doing the work,’ but in my experience only 10% of the people in the world ever make it from deer to tiger.

Counter arguments to working hard include burnout and missing out on life. The truth is, many startups do run on 80-hour weeks. 50 hours a week is probably the norm, and paying your dues early is the quickest way to acquire the skills necessary to become a founder yourself — and accumulate enough wealth never to work again.

Hustle early and often is the best life strategy.


There is always more knowledge to acquire, new skills to be mastered, yet most folks hoard their talents. This is a mistake. Give away everything you’ve learned, and take credit for doing so with your CEO with language like: “I’ve fully briefed our new hire Joe on how the blog and podcast work, and he understands the best practices we’ve established. I’ve asked him to update the best practice document if he learns anything new and to send us those learning points by email as well. What’s next?”

If you level people up you have a new job title: CEO!

Counter arguments to teach everything you know are many, not the least of which is “What will I do if someone does the job better than me?” Simple. You either learn from them or you move on to your next skill.

I’ve had executive assistants take over operations, operations managers take over sales, and sales executives take over marketing. Having multiple, overlapping skills is what defines the best senior executives often: “She started in sales, but now she’s CFO” and “He was a designer but now he runs product” are commonly heard.


The people who are killed, the deer, tend to huddle around the kitchen or go on cigarette breaks and bitch and complain about everyone and everything at the company. The tigers are too busy killing it to be bothered with such things.

If you see people crying and pouting walk away. Go back to work. Here’s the language:

Deer: “Bitch bitch, moan moan, blame blame, cry cry.”

Tiger: “Hmmm…that’s an interesting take on things. I gotta get shit done, good luck with that.”

You can always focus on the product, and how much it delights, helps, and inspires your customers instead of complaining.

Note: debating how to make your products better is healthy and your observations can be about the negative aspects of your product. However, you shouldn’t be negative on the team and company, you should see problems as opportunities.


If you’ve done 1-6 in the list above, it’s totally warranted to ask for more money or equity. I suggest asking for equity first and letting your boss bring up cash — she will, because she values the equity more (that’s a protip right there).

After five years of crushing it for your CEO, ask her to invest in, and be an advisor to your company…

….and then email me, because I’m the most helpful angel investor in the world. 🙂


In a startup things can often be vague and confusing, because things are just… starting… up. There is no HR manual or sales process, the org chart has never been memorialized and what you’re supposed to do next is confusing.

Oh yeah, things change constantly! Your job is to take what is unclear and make it clear. To take what is a vague concept and make it into a process. To take a system without metrics, strategy, and discipline, and install all of those things simultaneously.

That is called leadership, and leaders at their best define reality.


Don’t bust your ass and sharpen your skills for your boss alone, do it for yourself and your boss. Taking on all the problems at a startup is not being taken advantage of — it’s taking advantage of.

Slurp up all those problems and knowledge, and leave nothing for anyone else to do. Tackle the hardest problems, because those are the ones that make you strong, especially when you fail at solving them.

Have a great weekend … solving the problems your peers are too stupid and cynical to own.

best @jason


What I’m Reading (7/2/15)

Energy – Sam Altman
Free Templates for Great Startup Board Decks, Direct from VCs – NextView Ventures
They’re All P2P Employment Agencies – Techcrunch
Why The Church Should Neither Cave Nor Panic About the Decision on Gay Marriage – Dr Russell Moore
Startup Funding – Paul Graham
How to Raise Seed Capital – Nextview Ventures


Georgetown “Summer Ignition Series”

As I wrote last week, I’ll try to recap all of my classes at Georgetown with an essay here. Credit for the good material goes to Georgetown and their faculty. Mistakes or omissions are mine.

The McDonough School of Business (MSB) has my classmates and I off to an early start. Before I’ve even moved to Washington (some are already there posting enviable photos of social events online), we’re completing a week-long webinar series to prepare us for the upcoming tidal wave that is business school. Recruiting and interviews begin quickly and there will be infinite opportunities to network with various industry and company representatives. Before that beings, it’s time to take a step back to think deeply on the metanarrative of my career. To do so, the steps of the series are:

•Reflect: understand where you’ve been, are and are going

•Unpack: understand your accomplishments and how they relate to your career

•Clarify: focus in on where you want to go post-MBA

These goals were broken into four “deliverables” that I submitted to the career office.


Deliverable One: The Accomplishments Record

This was basically a résumé outside the typical résumé format. The assignment was to take your last three employers (or last three titles if you’ve worked at one company) and write out the five most important things you accomplished in each role. Here’s how it looked.


I spent a lot of time fine-tuning my résumé when I was applying to business school and this would have been really helpful. I like that it gets all the information first and asks for the resume bullet point last. It’s much easier to write an effective résumé point when you’ve written out all the information in pieces.

This took the longest but was very helpful.


Deliverable Two: Career Inventory

In short, this was a comparison of where you are and where you want to be, with a detour to ensure your understanding of where you want to be is accurate. This examination is somewhat parallel to the scientific method:

  1. Ask question
  2. Do background research
  3. Construct hypothesis
  4. Test with an experiment
  5. Analyze results and draw conclusion
  6. Hypothesis is: True (continue to step 7), or False or partly true (go back to step three)
  7. Report results

To do this, we completed a questionnaire to evaluate our fit for certain industries. Similar to personality tests, I answered 1-5 on a number of questions and totaled my score to determine different fits. You can recruit and interview with whomever you want, this was only for self-reflection.

Based on your scores in each function and industry you could get a sense of how your job search would be.



Deliverable Three: 355+ Value Strategy

We’ve narrowed down to the industries and functions (and maybe even companies) that are interesting. Now we can ask, “Why me?”, and even, “Why not me?”

The 355+ document will be useful in preparing for interviews and though we aren’t at that stage yet, I think Georgetown is wise to prepare us. It’s a useful analysis to complete for anyone interviewing.

  • 3 reasons you’re interested in the company
  • 5 most important things the employer needs
  • 5 best values that match with their needs
  • + why wouldn’t they hire you?


Deliverable Four: MSB Format Resume

This one was easy, just a lot of copying and pasting. I’m sure this is so they can put together résumé packets for recruiters to review. We took the bullet points from the accomplishments record and added them here.



Overall, this was a pretty useful experience. I want to go a less traditional route and join a startup so maybe my résumé perfection isn’t as important, but I’ll certainly use these frameworks in the recruiting process.

One more thing… I think the biggest value in these exercises is to get out of day-to-day “survival mode” that is easy to fall into and take time to think on who you are, where you’ve been, and where you’re going.


What I’m Reading (6/19/15)

What Do the Founding Teams of Billion Dollar Companies Look Like? – Requests for Startups
Firing Dick Costolo from Twitter would be a huge mistake – Jason Calacanis
Book: The Startup Game – William H. Draper III


Why I’m writing essays on my classes at Georgetown

Last year, I read Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel and Blake Masters. Blake was a graduate student at Stanford where Peter taught CS183 and his notes from the class provided the foundation for the book. (In the fall of 2014, CS183B was taught by Sam Altman, one of the founders of Y Combinator. It’s a great class titled How to Start a Startup.)

While at Georgetown I plan to write my class notes in a similar way. It’s well known that having to rephrase and teach information helps it be learned more deeply and that’s the intent behind writing these essays. If a best-selling book deal comes my way as it did for Peter and Blake, well that’s just a bonus.

My first essay recapping the summer ignition series at Georgetown will be posted in the next few days.


What I’m Reading (6/12/15)

How to Start a Startup – Sam Altman (Stanford University)
Apple is launching search engine to destroy Google — and you’re already using it – Jason Calacanis
Learn to Code: The Full Beginner’s Guide –  Lifehacker


What I’m Reading (6/5/15)

Book: The Hard Thing About Hard Things – Ben Horowitz
What’s one thing you’ve learned at Harvard Business School that blew your mind? – Ellen Chisa
How to Outsmart the Machines – Umair Haque
Washington’s Systemic Streets – Matt Johnson