When you look all at the iconic companies, there’s 1 undeniable shared trait:

A willingness to take risk.

In contrast, dying companies lack this trait.

So… how to do build an team that’s ok with risk?

It’s not so simple. Let’s dive in 👇👇👇
1/ Set a Threshold for Wrong

At Bolt, one of our favorite operating values is Chase 10X, Be 20% Wrong. (credit: Reid Hoffman)

The 20% figure really matters.

It puts a real number behind our willingness to make mistakes.

It gives the team something tangible to measure against.
2/ Praise Smart Failures

Failure is the lifeblood of a risk taking culture.

The mindset: Failure is progress. It means you learned critical information to inform your next step.

When giving feedback to your team, if they drove a smart strategy that led to a failure, praise it.
At Bolt we also grade people on risk taking in their performance reviews.

Taking risk is not just OK, it’s expected!

Take too little risk and you’re not moving fast enough. It might negatively impact your performance review!

Perfectionism has no place in a startup.
3/ Default to Experimenting

There is nothing worse than spending cycles theorizing for the perfect solution.

If something can be easily tested, test it.

If someone has a strong hunch, follow it.

Out with the theorizing. In with the action.
As with everything in business, there are pitfalls of overshooting.

There are RISKS with a risk taking culture!

Here’s what to avoid:
4/ Don’t be Shy To Admit Failure

A risk taking culture necessitates iterating quickly.

Failures are fine if you learn quickly, pivot, and keep moving.

It is devastating if you can’t admit failure.

Admit failure quickly to yourself, your team, and your partners.
5/ Watch Out for 1-Way Doors

Amazon has a great concept of 1 vs 2 Way Doors.

2 Way Doors you should act quickly and take risk all day. You can always turn around.

1 Way Doors you can’t get wrong. You’re stuck.

For the ones you can’t get wrong… don’t get wrong.
6/ Don’t Accept Sloppiness

Smart risks are great. Dumb risks are not.

Calculated mistakes are great. Careless mistakes are not.

A mistake once is great. The same mistake twice is not.
7/ Balance the Risk Taking

Risk taking should be balanced with with scaling your core business.

Invest too much in risk taking and your core breaks.

Invest too much in your core and you’re not innovating.

Pick a number. Eg 60% core 40% risk. Align your team accordingly.
8/ Don’t Break Prod

Our engineers love trying new features.

But companies rely on us for their critical path software.

We recognize this, and breaking for our customers is not covered by being 20% wrong!

We don’t mess with our production systems.
And there we have it!

Risk taking culture defined in 8 steps.

There is nothing more important than creating a culture that embraces risk.

Do it right, and you will unlock the X Factor in your organization.
Oh yeah, and risk taking is so friggin exciting.

Don’t forget the secret ingredient: keeping it fun.
If you enjoyed this and want to see tweets more like it, give me a follow @ryantakesoff.

I’m really excited to share my learnings building multiple billion dollar companies with you all.

Let’s take off together! 🚀

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More from @ryantakesoff

7 Oct
Fundraising

I have helped 100+ founders collectively raise $5B.

The biggest insight: fundraising is a game.

If you know how to play, you can do well.

Here are the 10 most common mistakes founders make 👇👇👇
Mistake 1: Complicated Pitch

The average VC spends 3 minutes on a pitch deck.

Crazy right?

Attention spans are shorter than ever, but consideration spans are still long.

People lean in if they're hooked.

So how do you hook them?

Keep the pitch simple.
Mistake 2: Building Relationships Late

It's hard to build a relationship with someone AND ask them for money at the same time.

Instead, develop relationships early.

Meet VCs, discuss your startup, share your progress.

When you need to fundraise, hit the ground running.
Read 13 tweets
4 Oct
In all of my spiritual work,

I’ve found no concept more important than Samsara.

They say that if you stare at the Wheel of Samsara long enough,

You become enlightened.

I will now explain it in plain english:
Samsara is a Buddhist concept that describes the suffering humans face over the course of one or many lifetimes.

We run on the wheel, like hamsters, until one day we finally see the wheel for what it is and step off.

There are 6 Realms that we all occupy at any give time.
Understand these Realms and you will understand humanity.

Ok, here we go…
Read 14 tweets
2 Oct
Leadership.

I never understood how important it was.

Until one day I realized our organization needed it.

That’s when I started my homework.

I started with a simple question: “What makes a great leader?”

Here’s what I learned…
Of everything I discovered,

Erica Ariel Fox has the best framework.

She describes The Big Four leadership traits.

Great leaders have one of these traits. The best leaders have multiple.

Here are the traits:
1/ Dreamer

This is your Visionary leader who can’t help but live in the future.

They value creativity and a bold long term perspective.

They spew innovation.

Usually, the CEO is a Dreamer.
Read 11 tweets
1 Oct
At Bolt we’ve experimented with 1000s of interview questions.

It’s been trial by fire, but the result is we’ve now hired 300+ amazing people.

For 5+ years, I interviewed every single candidate.

Here are my 15 highest impact questions to include in your hiring process 👇
Question 1: I’ve read your bio, but how about we start sharing each other's stories?

This sounds fluffy. It's not.

It’s crucial to learn who the candidate is.

The best teams are a combination of skills + incentives + personalities.

Most hiring stops at the skills part.
Question 2: Give me an example of adversity you’ve had to overcome and how you pushed through?

This question shows you a lot about someone’s character.

We face all sorts of adversity at startups (major and minor).

It's important to construct a team of creative problem solvers.
Read 19 tweets
28 Sep
At Bolt we grew from $400M to $4B in the last 10 months.

That's a 10x in 10 months.

This wasn’t an accident, but it also wasn’t a given.

The shift? We started making EVERY day count.

What exactly does that mean?

Let's break it down 👇👇👇
First, a step back:

We decided as a team that any tactic we took to “make the day account” had to come from one of 5 principles:

1. Accountability
2. Simplification
3. Curiosity
4. Empathy
5. Balance

Now let's talk tactics...
Tactic 1: Remove All Blockers

- “But X didn’t put a meeting on the calendar”
- “The other team hasn’t gotten back to me yet”
- “I didn’t hear from Y”

No. No. and No

Getting blocked is not tolerated.

Our team became relentless about problem solving vs. problem identifying
Read 14 tweets
25 Sep
In the last 90 days, we’ve closed more deals than ever before in Bolt’s history.

These deals alone have added billions to our valuation

This wasn't an accident.

We completely changed how we negotiate deals.

Here are 10 tactics we use today to negotiate Bolt’s best deals:
First, an important philosophical point.

People think that to win a negotiation, the other party has to lose.

That’s not congruent with our culture at Bolt.

Candidly, it’s also not effective.

The best deals expand the pie and both parties feel good about it.
Tactic 1: Tell the other party what makes them valuable to you.

It's disarming and changes the framing.

It makes them trust that you are truly valuing them.

Too many people are afraid to do this.

Don’t be. Do it early and often.
Read 14 tweets

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