Image for post
Image for post

Back in early March, before the full extent of this pandemic set in, I kicked off our introduction to remote work at Digits as follows:

To be sure, working remotely is not for every business, and not for every individual.

Little did I know how soon so many businesses and individuals would be forced to make do, and how quickly fully-remote work would become mainstream.

It’s been an abrupt transition… and for many, it hasn’t been easy.

Over the course of the year, I’ve heard from countless startup founders, small business owners, and team leads looking for more advice on…


Image for post
Image for post

The Social Dilemma, a years-long passion project from Jeff Orlowski and the Exposure Labs team, just premiered on Netflix this past week, and to my amazement and delight it has quickly jumped onto the Top 10 list this weekend.

The film masterfully intermixes drama with sit-down interviews with myself and a dozen other former social media execs, in hopes of communicating the (often subconscious) consequences of the world’s growing dependence on social media for news and entertainment.

It’s fantastic that this message is beginning to resonate broadly.

For those within the tech industry, of course, questions abound. In just the…


Image for post
Image for post

Wayne and I founded Digits 2 years ago to create the next generation of delightful, powerful business finance software, and we had a choice: how should we structure the business? When we landed on building a fully-remote startup, even some of our closest supporters were skeptical.

Can a fully-distributed team be productive?

Won’t everyone just slack off all day?

How do you brainstorm and make product decisions?

But, but… whiteboarding??

We immediately faced these and countless other questions, but we were convinced that we could not build the scale of business we envisioned in San Francisco, and we had a…


Image for post
Image for post

As builders, there is nothing more gratifying than crafting a product that is used by millions. That saves them countless hours of effort. That turns something complex and frustrating into something accessible, intuitive, even delightful…

Excited to finally share what Wayne Chang and I have been working on. We’re off on our next adventure! Welcome to Digits.

Read the full post on the Digits Blog


Image for post
Image for post
January, 2013

I am a big believer in transparency in business.

Done right, transparency promotes open and collaborative work environments. It fosters team trust and communication. And it promotes cultures where intellectual honesty and data-driven decisions supersede politics and excuses.

All that said, I have experienced first-hand the repercussions of being overly transparent, and I have spoken with countless founders who aspire to be transparent with their teams, but still struggle with how much to share, at what point, and to whom.

When I recently wrote about the role of the founder, I focused on your responsibility to scale yourself and empower…


Image for post
Image for post

Most people have a certain image in their minds when they think of a founder/CEO.

They picture the boss in the corner office, standing behind her desk, gazing out over the city. They imagine someone calling all the shots, and everyone relying on their insight and wisdom — a visionary who is never wrong. They fear being grilled, berated, and guilted into working long hours — inevitable top-down command-and-control.

When startup founders take this approach today, they fail.

In my experience, this couldn’t be further from the true purpose of the role.

Yet, too many founders fall into the trap of trying to live out this image — and I’ve seen their startups underperform…

Jeff Seibert

Co-founder of Digits. Previously, The Social Dilemma & Chasing Coral (→ Netflix), Fabric (→ Google), Crashlytics (→ Twitter) and Increo (→ Box)

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store