The Lonely Entrepreneur

We are all lonely entrepreneurs

But you are not alone

Wherever you are from $0 to $50 million, there’s a next right step—and a type of support built for what you need.

Explore the continuum

Trust is the first decision

Not sure who to trust?
You’re not alone.

You should never trust someone who has never been in your shoes—someone who has never stared at payroll and wondered how it would get made. TLE was built by an entrepreneur who has. Trust should be earned through experience, transparency and real results.

Why founders trust Michael →

500,000+Founders helped
600+CEOs helped by Sidekick
$4.9MAverage client revenue

Numbers matterBut the results are what earn your trust.See real client results

As featured inThe Wall Street JournalCNBCForbesBusiness InsiderFast CompanyEntrepreneur

Built by a founder who’s been through itMichael Dermer

Why founders trust TLE

Advice feels different when it comes from someone who lived it.

Michael Dermer built a company to 800 employees, watched it nearly disappear in ten days, then rebuilt, scaled and sold it. The Lonely Entrepreneur is everything he wished he had while fighting through it.

Ways we can help

No matter where you are,
we’re here to help.

From the first guide every founder should read to a trusted strategic partner, choose the kind of help you need now—at any revenue level.

Choose a solution

Select any option below to see what it includes, who it is for and the investment.

Survival Guide
$25
One-time
How to Survive in an AI World

Entrepreneur Survival Guide

McKinsey says 57% of what founders do every day can now be replaced by a machine. This is the playbook for how to survive — and thrive — in the world of AI. Not motivation. A system.

  • Finding Your Playground
  • Brand Chemistry
  • Operationalized Obsession
  • Resilience
  • Stretching Your Limits
  • AI as a Weapon

Complete Report
$39
Assessment free
Know Where You Stand

The Dermer Diagnosis

Will your business succeed? Answer a few questions and find out where you are strong, where you are exposed, and what is quietly holding you back. Free to take — unlock the Complete Report when you want the plan.

  • Business Success Score out of 100
  • Scores across five business areas
  • Your number-one exposure
  • Three ranked exposures explained
  • Three priorities and what to avoid
  • A focused 30-day action plan
Learn More →
Start Free →

Best For
Founders who want a diagnosis first

1-on-1 Session
$350
One-time · 60 min
Stuck or Unclear

Founder Clarity Hour

One hour with a senior consultant to cut through the fog. Walk in confused, walk out with a focused plan for what to do next.

  • 60-minute strategy session
  • Pre-call founder intake
  • Tactical action plan delivered
  • 3 Dos and 3 Don’ts
Learn More →
Buy Now →

Best For
Founders who need clarity now

Playground Report
$495
One-time
Find Your Playground

Playground Report

AI makes it easier to create, compete and copy. If customers can compare you to A or B, you have already lost. The Playground Report shows where you can define a market of your own.

  • Playground Verdict
  • Saturation + White Space
  • Opportunity Territories
  • Competitive Landscape
  • Market Economics
  • Risks + Evidence
Learn More →
Create My Report →

Best For
Founders who need to stand out

Annual Membership
$999
Per year
Under $1M in Revenue

The Learning Community

One place for answers you trust, support from people who’ve lived it, and a community where you’re never alone. Joined by 250,000+ founders worldwide.

  • 5,000+ learning modules
  • Entrepreneur Success Managers
  • Unlimited group coaching
  • Weekly Live with Michael Dermer
  • Tools, templates & vendor reviews
  • 400+ financing sources
Learn More →
Buy Now →

Best For
Founders under $1M

5-Week Program
$2,500
One-time
$1M–$5M Founders

Founder Blueprint

No one ever gave you the blueprint for how to run your business. Until now. A clear plan across the 5 key areas of your business, plus 5 one-on-one coaching hours to guide you.

  • Customers — repeatable demand
  • Team — right people
  • Money — cash, margins, capital
  • Being a CEO
  • AI — use it where it matters
  • 5 hours of 1:1 coaching included
Learn More →
Take Free Assessment →

Best For
Founders ready to scale

Ongoing Partner
$2,500
Per month · from
$5M–$50M CEOs

Sidekick Consulting

When you’re CEO of a $5M–$50M company, you don’t have one job — you have 15. Sidekick is your senior partner in the trenches: strategy, execution, and judgment from someone who’s sat in your seat.

  • Tackles the 15 critical CEO issues
  • Hours & deliverables tailored to you
  • Weekly check-ins with your Sidekick
  • 1 year of Learning Community
  • Packages range $7,500–$50,000
  • 600+ CEOs helped
Learn More →
Book a Free Strategy Call →

Best For
CEOs of $5M–$50M companies

Specialized Sidekicks

Two focused ways to go deeper

AI Sidekick

The AI Sidekick every CEO needs

The new 80/20 rule: 80% AI, 20% human. Put AI to work across your company so you don’t fall behind — with a partner who knows where it matters.

Exit Sidekick

Sidekick for the decisions you only make once

Selling your company may be the most important financial decision of your life. An independent advisor in your corner so you do the right deal — and protect what you built.

Not sure where to start?

Tell us two things. We’ll point you.

1 Where’s the business today?


2 What would help most right now?



We recommend
—

Learn more →

Results—not promises

Trust is earned.
Results prove it.

Founders have every reason to be cautious. See the businesses, the challenges and the measurable progress behind the numbers.

Two books. Two perspectives.

One is the true story of surviving the entrepreneurial impossible. The other is the guide founders reach for when the pressure is on.

The Lonely Entrepreneur — the book by Michael Dermer

The Lonely Entrepreneur
The true story of surviving the entrepreneurial impossible — and the mindset that got Michael through.

Get the book →

The Entrepreneur Survival Guide — the book by Michael Dermer

The Entrepreneur Survival Guide
How to survive in an AI world — the playbook founders reach for when the pressure is on.

Get the guide →

The Lonely Entrepreneur

We are all lonely entrepreneurs.

But you are not alone. One trusted ecosystem of support for the entire entrepreneurial journey.

Find your next right step