10 things I learned working for @Jason

Before founding dailydrip.com with [Josh](twitter.com/knewter), I worked for the legendary Jason Calacanis for three years as CTO of inside.com. I learned a lot from working with him, and wouldn’t trade that time to work with anyone else. Jason has higher standards than you can imagine, and the team around him works hard to exceed them. There is a huge amount of pressure to get things both right and fast. It is a high pressure environment where results matter, but he rewards the work with unsurpassed loyalty. There is no one more loyal to their team or founders than him.

I learned far more than will fit into a single post, but here are some of the more actionable things you can use:

1. TL;DR the TL;DR

People are busy. Keep your required communications short.

A great strategy is to write the full piece, then write a short summary, then summarize that a second time in a couple sentences. I’ll often take a short break between writing each summary, working on something else; that way each one is written with a fresh mind.

This pattern:

Write -> Break -> TL;DR -> Break -> TL;DR -> Send

ensures that your communication is short but complete. The breaks keep you from referencing information that isn’t included in the summary.

Just send the 2 sentence summary, not the full wall-of-text. If someone needs more details, trust that they will ask. You’ve already written up those details so you can respond quickly with just the requested information. Don’t make them sort extra info -- less is always more.

2. Extreme Visibility

Do not hide in the corner; do not sequester your work until it is perfect. Make sure you and your team’s work is open and transparent to everyone it can be in your company. For developers this can mean opening a pull request at the idea stage, not when the code is done. Maybe if you write for a living, you do it in the open in a shared document.

This isn’t an easy change, as it requires you to change how you work. You must constantly ask yourself: “Who might be interested in what I am working on, and how am I making it available to them?”

“Who might be interested in what I am working on, and how am I making it available to them?”

This transparency can be a lot of extra work, so your process has to support it. Build your process around transparency and your team will be much more efficient due to increased chances for communication. Your team can only help you if they know your status, and updating Trello or Tracker isn’t enough. Find ways to get exposure for your work early and often.

3. Make Deep Dives Available

This is a corollary to parts one and two. Find an accessible way to publish the long form, non-summarized things you learn about your company. Make them available to everyone possible. Everyone won’t read them, but it is there if they need to. Try writing notes at your daily stand-up, and put them into a special slack room. Or publish your weekly summaries to an internal wiki.

This will allow you estimate better, because you’ll find holes or inconsistencies in what you expected to happen vs what actually happened. This is also a powerful technique for testing marketing strategies: document everything, then judge their results vs your expectations.

4. Be Relentlessly Positive

Startups are difficult. People say that all the time, but it doesn’t really sink in until you’ve spent months building towards a big release, only to see it fizzle. You have to stay positive, for the benefit of your team and company. It doesn’t matter if you are the boss or the newest intern: It is your job to learn what you can, pick out the best performing parts, and rally your team around that. While this holds true for non-startups too, it is vital for early-stage ventures where you are iterating fast and experiencing a lot of failures.

Be the person that everyone feels excited about working with. Be the person that finds the successes hidden among the things that didn’t work, then double down on them!

5. Be Difficult -- Not Obstructive

It is important to question what you are doing, and why you are doing it. You should constantly be doing this as a team, and having healthy discussions about the direction you are taking the company as well as the specific execution of the steps in that direction.

That doesn’t mean those conversations should get in the way of actually getting stuff done. When you are considering a major investment of resources into a project, spend the time considering it to make sure it is a worthwhile project. Once that decision is made, it’s time to step back and support the team, regardless of how you feel about said decision.

You should also be tracking your initial thoughts and back-testing the results against those (see point three). Regular retrospectives are the place to discuss the results of those back-tests

6. Ask Better Questions

Jason is the king at this. Most people look at a situation and ask ‘What does this mean?’ or ‘How does this affect me?’ You have to go much deeper than this and really understand every aspect of a market or situation. The key to doing this is to build up a model of the situation in your head, and ask really hard questions about it. Find ways to break it. What happens in a black swan event? What is the effect if the market leader fails? What happens if the idea works?

...build up a model of the situation in your head, and ask really hard questions about it...

Figuring out how a system could break down will show you the holes in that system. Often finding these holes is how you exploit a given market. This doesn’t mean you are paranoid, just that you have a great situational awareness. It also means you are constantly thinking multiple moves out (think chess or go).

7. Impact Prioritization

This one is simple. Take everything that you need to get done and put it in a list. You can’t possibly get it all done, so order it by what has the most impact. Most often in startups this is what will generate the most growth or revenue.

Don’t mess with this! In startup land growth matters. In more established businesses growth matters, but so does retention, up-conversion, and a host of other things. You have to focus and make it happen.

8. Hocus Focus

Your focus should seem magical. Once you’ve picked something to spend your time on (it’s growth, right?) then nothing else matters until that is done. You can’t get distracted by social media, or Hacker News. You cannot let the overwhelming crush of your todo list freeze you with indecision.

Prioritize -> Focus -> Execute -> Repeat

Likewise, if you get interrupted, you can’t take out your frustration on the person interrupting you. You have to stay flexible enough to deal with changing requirements, then re-prioritize and re-focus.

9. Take a break

Your mind needs downtime. Those 70 hour weeks and months without a day off are not badges of honor. Instead they are a red flag identifying poor focus and poor prioritization. Schedule some time off, and be serious about it. Set reasonable working hours for yourself, and stick to them. Spend time with your family, and go work out.

70 hour weeks and months without a day off are not badges of honor

This goes for your entire team, too! At least once a year, make sure your entire team is in the same place (I prefer 2-3 times a year), and they do something fun together. With so many people working remotely now, it’s great to keep faces associated with the names in your slack channel. Taking breaks together will remind everyone they work with individuals, not robots.

10. Get Healthy

Remember how we said startups are hard? You’ll notice it’s a lot easier to tackle those challenges when you are pushing your body regularly. The links between exercise and cognative ability are very well researched. You need that exercise to be able to focus, so I’ll ask: When was the last time you worked out? If the answer wasn’t in the last 48 hours, then take a break (see point nine) and do it.

PS: @Jason is hiring for an EA position. I know from experience of working with his past amazing EAs like @BricePMilano and @AshleyRaeWG that this is not an entry level BS position. Both Ashley and Brice are amazing individuals that really care about startups, and have grown to be some of the most effective individuals I’ve ever worked with. They both have a bright future and I’m excited to see what they build. I’m sure this is partly due to Jason’s investment of his own time into their career and growth. If you want to get into startups, and really help new companies then you should apply.