Ask Great Cold Questions - Deepstash
Think Outside The Box

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Think Outside The Box

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Ask Great Cold Questions

Ask Great Cold Questions

When you meet new people, find ways to stand out. Asking great questions is a clear way.

A few to get you started:

What are you most excited about that you're working on right now?

What is your favourite book that you’ve read recently?

I know almost nothing about your field of expertise. Can you tell me more about that?

It gets the other person talking—plus they’ll remember you for future opportunities.


854 reads


Embrace the Unexpected

Embrace the Unexpected

You should spend your 20s saying yes to almost everything.

Saying yes puts you into uncomfortable situations that lead to new relationships, opportunities, and growth.

These unexpected moments are luck-rich. Embracing them is how you capitalize.


1.35K reads

Put Skin in the Game

Put Skin in the Game

It pays to bet some hard cash on new ideas that you have heard from smart people around you. 

The skin in the game forces you to dive deeper. Sometimes you learn more and fold; more often you learn more and double down. These are small bets with outsized returns.


1.01K reads

Send More Cold DMs

Send More Cold DMs

Twitter is an insanely valuable resource if you use it well.

You can literally reach almost anyone in the world from your couch. You can connect with many amazing people through sending them a cold DM—even if you don't have any followers.

Use my simple guide to hack the process. Shoot...


895 reads

Shallow men believe in luck. Strong men believe in cause and effect.



3.24K reads

Send More Cold Emails

Send More Cold Emails

Cold emails are responsible for some of the biggest breaks in my life—new mentors, relationships, and career opportunities.

Cold emails are a force multiplier for your efforts.

Follow the principles in my Cold Email Guide to enhance your odds of success.

Always remember:...


1.7K reads

Schedule Free Time

Schedule Free Time

The idea that free time is bad is one of the greatest lies you’ve been told.

In investing, it’s often said that cash is a call option on future interesting investments. Well, in life, I believe that free time is a call option on future interesting opportunities. When you have free time, you...


1.33K reads

Trust the Weekend Test

Trust the Weekend Test

Observe the weekend projects of the smartest people in your circles. These passion projects are disproportionately likely to be a looking glass into the future.

Make asymmetric bets on these areas.


1.34K reads

Create Value Without Expectations

Create Value Without Expectations

The best things in life come to those who create value with no expectation of a return.

When you put out good energy, it tends to come back to you—often multiplied.

Be genuine. Create value. Good things will happen.


1.18K reads

Get Out & Engage

Get Out & Engage

It’s hard to get lucky watching Netflix at home on the couch.

It’s (relatively) easy to get lucky when you’re engaging with people, interacting, and learning—in physical or digital worlds.

Spend more time engaging and you'll find yourself in more positions to get lucky.


959 reads

Spend Time in Digital Communities

Spend Time in Digital Communities

The world has changed—you no longer need to live in a big city or have a fancy degree to connect and build valuable relationships.

The rise of digital communities is real. Consider the fact that one of the co-founders of the largest play-to-earn game in the world started out as a member of ...


723 reads

Follow Your Curiosity

Follow Your Curiosity

Humans are born with astonishing curiosity. But somewhere along the way, we're told to stop asking questions.

Push back.

Learn to follow your curiosity—trust it. Curiosity drives you to knock down doors and enter new rooms.

Fortune favours the curious.


1.05K reads

Hustle Hard

Hustle Hard

When you have a bias for motion, good things happen. You create more random collisions in your ecosystems—it’s like chaos theory.

A bit of hustle goes a long way.


1.33K reads

Creative Boredom

Creative Boredom

We really need to normalize boredom. Some of your most creative moments come during periods of boredom.

On a walk, in the shower, at a dinner by yourself. You’re bored, your mind wanders, your thoughts mingle. Bam! Insight strikes.

Boredom creates luck. Go for more walks (sans technol...


875 reads

Ruthlessly Eliminate Negativity

Ruthlessly Eliminate Negativity

Everyone has a few negative people in their circle. They tell you to be realistic. They laugh at your ambition. They argue.

Eliminate this negativity from your life. It's a boat anchor—a major black hole—cut the damn line and run away from it as fast as you can.

Negative peopl...


1.24K reads

Luck Is Programmable

Much of what we come to call "luck" is actually the macro result of 1,000s of micro-actions. Your daily habits put you in a position where “luck” is more likely to strike.

In order to get lucky, you have to remove the “black holes” (anti-luck) from your existence. You ...


3.7K reads

Become an Expert

Become an Expert

If you are exceptional at one specific thing, luck tends to find you.

Your expertise becomes a magnet for new and interesting opportunities you never knew existed.

Public awareness of your expertise is a plus. Share your work to widen the reach of your magnet.


924 reads


Diligence is the mother of good luck.



3.09K reads

Be the Dumbest in the Room

Be the Dumbest in the Room

If you have a choice between entering two rooms, choose the room where you are more likely to be the dumbest one in the room.

Once you’re in the room, talk less and listen more. It’s bad for your ego, but it’s great for luck.

Good things tend to happen in these rooms.


2.9K reads

Hang Out With Optimists

Hang Out With Optimists

Pessimists sound smart, optimists get rich.

When choosing who to spend time with, prioritize spending time with optimists. Pessimists see the doors that are closed. Optimists see the doors that are open—and probably kick down the closed doors.

Pessimists are “black holes” in your life...


2.33K reads

Get in the Arena

Get in the Arena

There's no luck on the sidelines—the arena is where it strikes.

It's lonely and vulnerable, but it's the only path that bears real fruit. When faced with two paths, choose the path that puts you in the arena—where collisions happen, where luck can strike.

Furthermore, surround yoursel...


1.96K reads

Write in Public

Write in Public

When you write and publish your ideas and insights, you are casting a web of magnets out into the world.

Those ideas and insights will attract some people to you—and perhaps repel others.

As your web grows, the connections—and luck—compound accordingly.


1.94K reads

Talk to Strangers

Talk to Strangers

"Don't talk to strangers" is a classic we are told as children—the residue of which carries into adulthood for far too many people.

New relationships spark new ideas, insights, and opportunities—these compound just as well as any financial investment.

Broad Network = Broad Luc...


1.77K reads


There’s luck through persistence, hard work, hustle, and motion. This is when you’re running around creating opportunities. You’re generating a lot of energy, you’re doing a lot to stir things up. It’s almost like mixing a petri dish or mixing a bunch of reagents and seeing what combines. You...



1.23K reads




I put the "pro" in procrastination. And I wisht I didn't.

Get your Luck from this stash.

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7. Ask Questions

The key, however, is to ask open-ended questions . That is, ask questions that don’t have a simple “yes or no” answer.

It’s the difference between Do you like living here? and What do you think about living here? Or the difference between Where did you...

Ask specific questions

At the end of a job interview, you should have the opportunity to ask questions.

Ask questions about culture qualities you've identified as important to you. Remote-specific questions about company culture include:

  • How does your team maintain strong bonds?

Questions to ask a mentor

To save the time of both of you, consider asking your mentor these questions:

  • Thinking back to when you were just getting started, what parts of your skill were the most frustrating to learn?
  • Which of those do you use on a daily/weekly basis, and which have you forgotten?


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Sean Green

Great interesting short snippets of informative articles. Highly recommended to anyone who loves information and lacks patience.


Don’t look further if you love learning new things. A refreshing concept that provides quick ideas for busy thought leaders.

Shankul Varada

Best app ever! You heard it right. This app has helped me get back on my quest to get things done while equipping myself with knowledge everyday.

Ashley Anthony

This app is LOADED with RELEVANT, HELPFUL, AND EDUCATIONAL material. It is creatively intellectual, yet minimal enough to not overstimulate and create a learning block. I am exceptionally impressed with this app!

Laetitia Berton

I have only been using it for a few days now, but I have found answers to questions I had never consciously formulated, or to problems I face everyday at work or at home. I wish I had found this earlier, highly recommended!

Giovanna Scalzone

Brilliant. It feels fresh and encouraging. So many interesting pieces of information that are just enough to absorb and apply. So happy I found this.

Jamyson Haug

Great for quick bits of information and interesting ideas around whatever topics you are interested in. Visually, it looks great as well.

Ghazala Begum

Even five minutes a day will improve your thinking. I've come across new ideas and learnt to improve existing ways to become more motivated, confident and happier.

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