Mental health is one of the most overlooked areas of productivity optimization for entrepreneurs.

A lot’s been said about the mechanics of building a startup (MVPs, fundraising, customer acquisition, etc) but the driving force making it all happen, a founder’s brain, gets relatively little attention.

Small investments in this area can have outsized results in terms of energy, problem-solving, ideation, stamina, and communication.

As I recently wrote:

I believe the single most important ingredient for long-term success is how you feel psychologically.

For that reason, I aim to return to the subject regularly.

Today, I’m looping in Silja Litvin, CEO…

Last year revered founder, investor, operator, and incredible human being, Tony Hsieh died totally unexpectedly at 46.

He is probably best known as the former CEO of Zappos, the online shoe retailer acquired by Amazon in a deal worth $1.2 billion way back in 2009.

His untimely demise was met with great sadness by the tech community — particularly those who knew him — including a ton of high-profile founders, former colleagues, and VCs.

I wasn’t lucky enough to count myself in that group, so in an effort to learn more about his life and journey as an entrepreneur, I…

I know firsthand how frustrating it is to be a victim of commercial cybercrime.

Both emotionally from watching your livelihood attacked, and, financially from losing a ton of money as a result of business disruption.

Cybercrime has affected me since the first company I founded with friends, just over ten years ago.

We built a website that became highly trafficked, reaching the top 1,000 most visited sites globally within 1.5 years of going live.

One day, a few months after launch — which happened to be the exact day I quit my 9–5 banking job to focus on growing the…

You often hear about how perseverance played a huge role in the success of an entrepreneur’s journey.

Stories about how ‘XYZ founder didn’t give up’, ‘just kept at it’, and ‘defied the odds’ despite continual setbacks, marketplace resistance, and scepticism are characteristic startup origin scenarios that persist throughout a company’s lifecycle until maturity.

In fact, this was a core theme in one of the first founder biographies I read at the beginning of my entrepreneurial career — Walt Disney: An American Original by Bob Thomas.

It’s forgiving to assume Walt Disney had an ‘easy time’ building his entertainment company because…

Cold emailing has been one of the most popular topics I’ve written about through Founders’ Hustle so far.

The idea that you can connect with someone extremely knowledgable, well-connected, or wealthy — from anywhere in the world, right now, for free — is incredibly compelling.

It’s such a powerful mechanism, partly because the returns can be so massively asymmetrical.

The act of sending a cold email is a small investment, but, if structured well, can deliver life-changing results.

Things like landing investment, your first client, a key hire, or incredible advice.

I’m not just saying this. It’s been a critical…

If you have an iPhone app in the marketplace or are planning on releasing one, you’re likely astutely aware of the ‘bombshell’ update Apple is about to drop on iOS 14.5 as part of its App Tracking Transparency framework — IDFA deprecation.

To those uninitiated, Identifier for Advertisers (IDFA) is a random device identifier assigned by Apple to a user’s device.

Advertisers, and indeed the entire mobile adtech ecosystem, use it to track the performance of ad campaigns down to the user level.

IDFA gives total visibility over how consumers engage with ads and behave in apps after downloading them…

“People often talk about how Silicon Valley’s “Move Fast & Break Stuff” ethos is one of its secret weapons.

This idea can be implemented in a huge variety of ways, from the wildly unethical, to the ill-considered, to just using the phrase to handwave away chaos and poor leadership.

But at its core, there is a secret weapon in that phrase.

If you can do it right, the ability to move fast, and the willingness to break (the right) stuff can result in learning massively faster and more effectively than your competition.

But there’s a huge challenge in implementing a…

OthersideAI was launched in the latter half of 2020 by three college-aged founders — Matt Shumer, Miles Feldstein, and Jason Kuperberg.

The company’s origin story is incredible.

It’s pretty much a text-book idealistic ‘launch’ framework for founders who want to build a venture-scale business.

Here’s a basic overview of key events.

In July 2020 the team spent a couple of hours making a product demo and posted it to Twitter.

Without many followers, they didn’t expect much to come of it.

Instead, it went viral, receiving around 1,000,000 views and reactions from prominent figures in the venture capital and technology…