A Smart Bear

Startup founders undervalue their time.

RICE and other confidence-based frameworks are mostly noise.

Worrying makes things worse.

If you don't hire people better than you, the organization gets bigger, not better.

In the quest for optimization, A/B tests, metrics, and funnels, we're in danger of losing the fun and value of creative work.

Real strategy means choosing between two good options and accepting all the consequences--even the painful ones you don't like.

A compass tells you which way is north, not whether you should be heading north.

Do less, to create the space to be great.

Delegation doesn't scale your business.

Mission, vision, purpose, BHAG.

Expertise hinders learning.

How to define your actual target market, which probably isn't traditional demographics and firmographics.

Have a great idea?

Your company will stop growing sooner than you think.

Want to write better?

Because time is zero-sum, prioritization is mandatory.

Bootstrapped and unsure about CPC?

You must select between three pricing strategies, and fully commit to their implications.

Nothing clarifies things quite like a hyperactive, all-knowing, all-seeing, real asshole of a devil's advocate beating the living crap out of you.

Little, unknown companies with silly names can sell to enterprises who have already spent millions.

Having skipped to the last page of other people's books, we forget the rest of the journey.

When even "free" is too expensive.

Customers love you when you're honest, even about your foibles.

How can a business that is "spending to grow" determine whether it's truly profitable underneath all that "revenue acceleration?"

What can't be solved with money, are the most valuable things.

The difference between "low prices" as a race to the bottom or as a success story (like Amazon, Costco, IKEA, Vanguard) is in leveraging intentional weaknesses.

Simplify complex decisions by separating upsides from downsides, investing in upsides, vetoing with downsides, and using an appropriate decision framework.

Identifying useful frameworks for companies, strategy, markets, and organizations, instead of those that just look pretty in PowerPoint.

Freemium means high costs, low conversion, and customer feedback dominated by the non-ideal customer.

Comparing yourself to other startups?

This isn't the humble-brag you think it is; The most common origin story is also common to startups that fail.

Competing against big firms?

When you're brand new, how do you select your first marketing channel?

Being "undefeated" or "number 1" might be more luck than you know.

Why do smart, driven founders fail, despite having great ideas and execution?

You redesign your entire website, customers and employees say it's better, but none of the metrics change… Does design even matter?

Oh you secretive devil!

This is the reason that startups succeed despite their many weaknesses.

The two main business modalities are more different than you expect.

It is true that small changes can have enormous effects?

How to find potential customers to interview before you have a product, a website, or even a name.

Low on cash but need marketing results?

Brittleness is when the company fails because just one component breaks.

Our emotional baggage and experience make us unique, but also serve as blinders.

Erica Douglass sold her company for $1M, yet still struggles with self-worth; why driven people can't escape Impostor Syndrome.

Half of your "successful" A/B tests are false-positives.

Applying Pascal's Wager: Humility wins, arrogance loses.

Is it LTV?

Tech support isn't just troubleshooting; it's the face of your company.

A contrarian look at logical "fallacies" that maybe aren't so illogical after all.