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When you are CEO of a $5M to $25M company, you don't have one job - you have 15.
You can’t fix marketing without fixing messaging.
You can’t scale without process.
You can’t grow if everything runs through you.
Sidekick isn’t a coach. It’s your one place for strategy and execution — across your business.
You don't need another business coach. You need a Sidekick.
Don’t ask us. Ask the CEOs we’ve helped.
The New Model of Business Coaching
Learn how $5–25M companies scale. Get your free strategy consult.
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.
Our customers say, “I wish I found you a year earlier.”
Built By a CEO Who's Lived It
Michael Dermer didn’t just build a company—he created an industry.
Founder of the first company to reward healthy behavior—called it a crazy idea at the time.Grew to 800 employees before nearly losing everything in the 2008 financial crisis.
Saved it, rebuilt it and sold the company—recognized as the pioneer of the health rewards industry.
Now brings battle-tested strategy and execution to CEOs through Sidekick.
Thousands of CEOs trust Sidekick to solve the 15 issues that stall growth—because it’s built by someone who’s been in the seat, made the tough calls, and come out the other side.
This isn’t theory. It’s the truth from someone who scaled, led, fell, rebuilt, and exited. Watch Michael’s Story
What Sidekick Clients Are Achieving
Revenue gained. Capital raised. Chaos conquered.
+45% EBITDA
Revenue & Cost ReductionsRestructured pricing, optimized team cost, and removed vendor waste
Raised $100M
Series B FinancingSet foundation for mid market GTM that appealed to investors in crowded market
$26 Million Deal
Realized 14X EBITDA MultipleCreated positioning, competitive bidding process and drove internal training for leadership team
+$4M Revenue
$12M → $16M in 18 MonthsRebuilt GTM, repositioned offering, and drove current customer expansion and growth of customer base
+$6M Revenue
$11M → $17M in 24 MonthsChanged core messaging, reworked sales targeting and differentiators versus growing competition
+$5M Revenue
$6M → $11M in 24 MonthsReplaced core sales and marketing leadership team, implemented performance management and drove client engagement model
Collect $900K
Reduced ReceivablesReworked billing process, changed pricing model and leveraged accounting systems and teams
$1M LOC
Introduced and Closed FinancingEnhanced financial presentation, trained leadership for presentation and negotiated terms
Save $3M Debt
Negotiated with LandlordSecured agreement to release, drove core team to secure alternative location
Saved $1.2M
Changed Product DevelopmentReworked development plan, changed IT vendors and accelerated go to market launch date
$125K Saved
Legal Dispute ReducedResolved internal conflict with former employee, leveraged lower cost legal options and reduced overall expenses
Save $40K/Mth
Marketing Cost ReductionConsolidated vendors, aligned spend to ROI and hired in house marketing resource
What CEOs of $5M to $25M Companies Say
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
