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Ryan Deiss
Ryan DeissI help burnt-out bootstrapped business owners scale their companies...without sacrificing their souls.
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A Simple System for Replacing Outdated Annual Planning With a 90-Day Plan Rhythm That Actually Works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
The Five-Figure Free-Up
Profit & Cash Flow

The Five-Figure Free-Up

A Simple System for Freeing Up (At Least) $10K/Month in Wasted Expenses...While Training Your Team to Guard Cash Like an Owner

Ryan Deiss
Ryan Deiss
Sep 7, 2025
Impact-First Delegation
Ops & Productivity

Impact-First Delegation

A Simple System for Buying Back 8 Hours a Week by Deleting, Delegating, and Documenting the Right Tasks...Without Hiring a “Unicorn” COO

Ryan Deiss
Ryan Deiss
Aug 31, 2025
The YouTube Binge Loop
Sales & Growth

The YouTube Binge Loop

A Simple System for Lowering Lead Costs and Shortening Sales Cycles By Turning Your YouTube Channel Into a Content Binge-Factory

Ryan Deiss
Ryan Deiss
Aug 24, 2025
The Clarity Compass
Team & Leadership

The Clarity Compass

A Simple Framework That Enables Your Team To Make High-Stakes Decisions as Good (or Even Better) Than You...and Ends “Got a Minute?” Interruptions Once and for All

Ryan Deiss
Ryan Deiss
Aug 17, 2025
The Daily CEO Checklist
Ops & Productivity

The Daily CEO Checklist

A Simple System for Transforming Daily Chaos Into High-Leverage CEO Decision (and Actions)...in Under 10 Minutes

Ryan Deiss
Ryan Deiss
Aug 10, 2025
Four Little-Known “Impact Metrics” That Will Make (or Break) Your Business This Year
Team & Leadership

Four Little-Known “Impact Metrics” That Will Make (or Break) Your Business This Year

A Simple System for Identifying the Metrics that Matter vs. the “Vanity Metrics” that Merely Make Noise

Ryan Deiss
Ryan Deiss
Aug 3, 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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