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Ryan Deiss
Ryan DeissI help burnt-out bootstrapped business owners scale their companies...without sacrificing their souls.
The Saturday Problem
Ops & Productivity

The Saturday Problem

A Simple System for Getting Your Most Important Work Done Before Friday...Without Adding More Hours to Your Week

Ryan Deiss
Ryan Deiss
Mar 15, 2026
How to Fix a Broken Team...Without Firing Anyone
Team & Leadership

How to Fix a Broken Team...Without Firing Anyone

A Simple System for Finding Out if Your Playbooks Are Broken...or if Your People Just Suck

Ryan Deiss
Ryan Deiss
Mar 8, 2026
This Simple Email Gets Us A-Players (And Cuts Our Interview Time In Half)
Team & Leadership

This Simple Email Gets Us A-Players (And Cuts Our Interview Time In Half)

How one pre-interview email filters out "bad-fit" employees, shortens the hiring process, and locks down your best applicants...before you ever meet with them.

Ryan Deiss
Ryan Deiss
Mar 1, 2026
I Read Every Business Book You're "Supposed" to Read...Here's What They Got Wrong
Ops & Productivity

I Read Every Business Book You're "Supposed" to Read...Here's What They Got Wrong

A founder’s guide to what your favorite business books got right, what they get dangerously wrong, and what actually works at scale.

Ryan Deiss
Ryan Deiss
Feb 22, 2026
I Just Rewrote My Job Description. Here's How (and Why) I Did It.
Team & Leadership

I Just Rewrote My Job Description. Here's How (and Why) I Did It.

A simple system for redesigning your role so you can banish burnout and fall in love with your business again

Ryan Deiss
Ryan Deiss
Feb 15, 2026
The Most Expensive Hiring Mistake I Ever Made (and What It Taught Me)
Team & Leadership

The Most Expensive Hiring Mistake I Ever Made (and What It Taught Me)

This one leadership mistake cost me a great employee, a friendship, and (conservatively) millions of dollars in growth that could have happened but didn't.

Ryan Deiss
Ryan Deiss
Feb 8, 2026
5 “Skills” I Had to Unlearn to Scale from $1M to $10M
Team & Leadership

5 “Skills” I Had to Unlearn to Scale from $1M to $10M

I thought scaling meant learning more. Turns out, it meant unlearning almost everything that made me successful early on.

Ryan Deiss
Ryan Deiss
Feb 1, 2026
I Owed the IRS $248,000. This One Thing Bailed Me Out.
Profit & Cash Flow

I Owed the IRS $248,000. This One Thing Bailed Me Out.

How an unexpected tax bill taught me one of the most important business lessons I’ve ever learned...and why your email list is more than just a marketing asset.

Ryan Deiss
Ryan Deiss
Jan 25, 2026
5 Big Lessons I’m Bringing Into 2026 (Based On My Biggest FAILURES In 2025)
Team & Leadership

5 Big Lessons I’m Bringing Into 2026 (Based On My Biggest FAILURES In 2025)

Five leadership lessons forged in layoffs, shutdowns, and impossible calls.

Ryan Deiss
Ryan Deiss
Jan 18, 2026
Don't Hire a COO. Do This Instead.
Team & Leadership

Don't Hire a COO. Do This Instead.

The Five Leadership Roles Every $2M+ Business Must Have

Ryan Deiss
Ryan Deiss
Jan 11, 2026
The Pre-Loaded Year
Ops & Productivity

The Pre-Loaded Year

A Simple System for Achieving Big Business Goals Without Sacrificing Family, Health, or Rest

Ryan Deiss
Ryan Deiss
Jan 4, 2026
The 2X in '26 Playbook
Profit & Cash Flow

The 2X in '26 Playbook

A Simple System for Doubling Revenue in 2026 Without Doubling Headcount, Marketing Spend, or Chaos

Ryan Deiss
Ryan Deiss
Dec 14, 2025
The Founder-Type Framework
Team & Leadership

The Founder-Type Framework

A Simple System for Identifying Your Default Leadership Style...and the CEO Type Your Company Needs for the Year Ahead

Ryan Deiss
Ryan Deiss
Dec 7, 2025
The 3-5-1 Quarterly Sprint Planning Method
Team & Leadership

The 3-5-1 Quarterly Sprint Planning Method

A Simple System for Replacing Outdated Annual Planning With a 90-Day Plan Rhythm That Actually Works

Ryan Deiss
Ryan Deiss
Nov 30, 2025
10 Hard-Earned Lessons I Wish I'd Learned 20 Years Ago
Mindset and Personal Growth

10 Hard-Earned Lessons I Wish I'd Learned 20 Years Ago

A Simple Playbook for Scaling Without Burnout, Building Wealth Without Chaos, and Living a Life You Don’t Have to Escape From.

Ryan Deiss
Ryan Deiss
Nov 23, 2025
The 3 Skills Every $1M Founder Must Master To Become a $10M CEO
Team & Leadership

The 3 Skills Every $1M Founder Must Master To Become a $10M CEO

A Simple System for Upgrading Your Leadership, Your Team, and Your Cash Flow so You Can Scale Past $10M Without Working More or Burning Out

Ryan Deiss
Ryan Deiss
Nov 16, 2025
CEO Thinking Time Framework
Mindset and Personal Growth

CEO Thinking Time Framework

A Simple System for Getting Unstuck, Refocusing Your Priorities, and Making Better Decisions in Just 60 Minutes a Month

Ryan Deiss
Ryan Deiss
Nov 9, 2025
How To Double Your Prices (5 Steps)
Profit & Cash Flow

How To Double Your Prices (5 Steps)

A Simple System for Doubling Your Prices...Without Losing a Customer

Ryan Deiss
Ryan Deiss
Nov 2, 2025
The Leverage Ladder
Ops & Productivity

The Leverage Ladder

A Simple System for Compounding Results Without Compounding Effort

Ryan Deiss
Ryan Deiss
Oct 26, 2025
The Immutable Marketing Laws
Sales & Growth

The Immutable Marketing Laws

A Simple System for Building Marketing That Works in Any Economy and Any Platform...Even in the Age of AI

Ryan Deiss
Ryan Deiss
Oct 19, 2025
The Owner Pay Stack
Team & Leadership

The Owner Pay Stack

A Simple System for Knowing Exactly What to Pay Yourself as a Founder/CEO...Without Starving the Business or Getting Stuck on the Feast-or-Famine Rollercoaster

Ryan Deiss
Ryan Deiss
Oct 12, 2025
The Fair Firing Framework
Team & Leadership

The Fair Firing Framework

A Simple System for Knowing When to Let a “Good” Person Go...and How To Do It With Kindness and Dignity

Ryan Deiss
Ryan Deiss
Oct 5, 2025
The AI-Powered Org Chart
Team & Leadership

The AI-Powered Org Chart

A Simple System for "Hiring" and Training AI Employees that Amplify Your Existing Team and Fill Missing Roles...Without Adding To Your Payroll and Overhead

Ryan Deiss
Ryan Deiss
Sep 28, 2025
The 2 to 20 Playbook
Team & Leadership

The 2 to 20 Playbook

A Simple System for Crossing the $2M to $20M Chasm...Without Losing Your Family, Your Friends, Your Margins, or Your Mind in the Process

Ryan Deiss
Ryan Deiss
Sep 21, 2025
The CEO Dashboard Blueprint
Ops & Productivity

The CEO Dashboard Blueprint

7 Rules for Building a Company Scorecard That Spots Bottlenecks, Forces Accountability, and Keeps Your Company on Track

Ryan Deiss
Ryan Deiss
Sep 14, 2025
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Accidental MBA

Tactical Business Advice for Successful "Accidental Entrepreneurs" Who Want To Scale To $10 Million and Beyond

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