The most important piece of advice for folks starting their careers

[ From a tweet storm last week ]

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

2/Refine your skill faster than your peers.

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.

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3/Take your skills to a startup. Period. Full Stop.

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.

4/Once you’re noticed by the CEO: take on every project she offers.

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.

5/Teach everyone around you everything you’ve learned.

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.

6/Never get involved in politics & never be negative.

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.

7/Get as much equity as you can, don’t be afraid to ask for more!

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. 🙂

8/Bring order to the chaos, define reality

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.

In conclusion

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

PS – If you’re a founder or considering being one, apply for a scholarship to my SCALE event on Oct 13th & 14th here in San Francisco. At the event 50 speakers will explain how to grow your company. If you’re not a founder, please buy an affordable ticket ($500, cheap — $10 a talk, and you’ll get all of them on videos that will not be released to the public).

PPS  – If you’re a VC, angel, or press and want to come to our DEMO / Bastille Day party on July 14th email If you’re anyone else you can follow my Twitter handle @jason — we’re giving 10 people per day a free ticket!