#1 Business Coach for $5M–$25M CEOs, Not Just a Coach - A Sidekick
We'll help you fix your specific problem blocking your growth — whether it's sales, marketing, finances, team management or your role as CEO — we'll execute with you every step of the way.
Ask the 600+ CEOs we’ve helped.
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The Results Sidekick Delivers
Increased EBITDA via pricing, team and vendor changes
Increased revenue in 18 months from $11 to $18M
Series B financing with mid market go to market strategy
Acquisition at 14X EBITDA multiple achieved
Every CEO needs a Sidekick — one place they turn to for strategy, guidance and execution.
We don’t consult — we deliver change across the 15 critical issues that make or break $5 to $25M companies. These are the issues we see in companies that are not achieving the success they deserve.
And we don’t just know the issues — we know how to solve them. This is not theory. It’s execution. It’s measurable outcomes.
“As CEO I was unprepared to juggle growth, sales, marketing and cash all at once. It wasn’t until I had a Sidekick that I finally got the support, clarity, and results I needed.” Sidekick Client, $12M Company
How Sidekick Works
Diagnose
Assess the state of your company: talent, capital, strategy, execution.
Establish Priorities
Identify the top areas that will drive the biggest impact.
Apply Sidekick Formula
Combine strategy and execution to deliver ROI.
Execute With You
Side-by-side with your team to deliver results.
Built By a CEO Who's Lived It
Michael Dermer didn’t just build a company—he created an industry.
Pioneered the health rewards industry.CEOs trust Sidekick because it’s built by someone who’s been in the seat and came out the other side.
Sidekick helps $5M–$25M CEOs execute across the 15 critical issues that make or break success.
Cash Flow
Financial Plan
Revenue Strategy
Sales Excellence
Performance
Raising Money
Setting Goals
Being a CEO
No More Solar System
Setting Priorities
Legal Strategy
Time Management

What Sidekick Clients Are Achieving
“I kept trying to fix one area at a time — sales, marketing, cash — but I was struggling. I didn’t know which levers to pull. Only when I had a Sidekick did I get the right levers to move the business forward.”
Sidekick Client, $18M Company
We now know what it takes to build good financials, a go to market strategy and the right outlook to bring our business forward in the right distribution channels. The coaching is on point and as helps us stay focused on the processes and priorities that get us there.
Clair Norman
Co-Founder | Solo Spouse
As we grew, we developed an organization that was not set up to serve our markets effectively. Our Sidekick set the operational structure we needed across management, sales, marketing and finance that has served us well as we grow. And it has taught me many of the skills I need as CEO of a $100M company.
Marco D.
Founder & CEO | Royalpark
TLE’s Sidekick is exactly what CEOs of growing companies need. Their guidance was essential to preparing us for the large fundraise we completed (100M) and set us up for the success we achieved from that point forward.
Jordan F.
CEO | Rightway Health
The business and legal guidance we got from TLE helped us accomplish some key objectives. We were able to change our mindsets as leaders, rework a complex partnership and evaluate the ROI of various business decisions. Their counsel has been invaluable in our journey.
Maya K.
Founder & CEO | Wholesome Yum
The journey to Shark Tank and landing a deal with Marc Cuban was a long one. And the team at TLE contributed to my growth as a leader and helped me understand what it takes to turn your passion into real economic success.
Ashley J.
Founder | Tones of Melanin
Working with TLE gave us a different perspective on what goals to set and how to achieve them, helping us to a 60% increase in sales in our first year. TLE has been instrumental in helping to create a new culture, expect higher standards, and streamline our processes for long-term success.
Dave F.
CEO | Fisher Shipping
The Lonely Entrepreneur provided invaluable guidance to the founder, the advisory board and various other advisors to align the financing plan to the go to market strategy. And along the way was teaching the founder to be a CEO.
Kim P.
CFO | Multiple Companies
I’d been struggling raising money. I was about to send out my investment materials when I learned of TLE. The difference between my approach and the approach TLE brought me was clearly the difference in the success of our fundraising efforts.
Angelo V.
Founder & CEO | Vuew
Kelly B.
Co-Founder | Kelly B.Co-Founder | Solospouse
I wanted to grow my social media. What I learned from The Learning Community and TLE led me to create a post for my golf tv show Saturday Foursome that got over 350K views.
Edgar Evans
Founder | Flawless Golf Shoes
Sidekick Pricing. Simple. Transparent.
No bloated retainers. A package of hours tailored to your priorities.
Weekly check-ins, deliverables, and execution with your Sidekick.
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