Sidekick Changes the Game for CEOs
We encourage you to speak to the CEOs we’ve helped.
Our customers say, “I wish I found you a year earlier.”
Book a Strategy Call To Discuss Your Business
+45% EBITDA
Revenue & Cost Reductions
Restructured pricing, optimized team cost, and removed vendor waste
Raised $100M
Series B Financing
Set foundation for mid market GTM that appealed to investors in crowded market
$26 Million Deal
Realized 14X EBITDA Multiple
Created positioning, created competitive bidding process and drove internal training for leadership team
+$4M Revenue
$12M → $16M in 18 Months
Rebuilt GTM, repositioned offering, and drove current customer expansion and growth of customer base
+$6M Revenue
$11M → $17M in 24 Months
Changed core messaging, reworked sales targeting and differentiators versus growing competition
+$5M Revenue
$6M → $11M in 24 Months
Replaced core sales and marketing leadership team, implemented performance management and drove client engagement model
Collect $900K Cash
Reduced Receivables with Core Customers
Reworked billing process, changed pricing model and leveraged accounting systems and teams
Secured $1M LOC
Introduced and Closed Financing
Enhanced financial presentation, trained leadership for presentation and negotiated terms
Reduce $3M Debt
Negotiated with Landlord
Secured agreement to release, drove core team to secure alternative location
Saved $1.2M
Changed Product Development Plan
Reworked development plan, changed IT vendors and accelerated go to market launch date
$125K Saved
Legal Dispute Reduced
Resolved internal conflict with former employee, leveraged lower cost legal options and managed lawyer expenses
Saved $40K/Month
Marketing Cost Reduction
Consolidated vendors, aligned spend to ROI and hired in house marketing resource
$2.5M Cash Flow
Via Pricing Overhaul
Shifted to value-based pricing, re-negotiated renewals and increased average client size by $100K
3x Client Size
$15K → $45K Avg Deal
Streamlined pricing, targeted different customer size and repositioned solution tiers
+$900K/Quarter
Client Revenue Growth
Launched strategic upsell playbook, optimized retention and added more strategic marketing function
$2M Debt Removal
Lease Release Negotiated
Structured landlord buyout and exit path with no payout on past liability
$375K Saved
Marketing Brought In-House
In-housed team, rebuilt assets, and eliminated legacy agency spending inefficiently on ad spend
4x Booking/Mth
$25K → $100K/Month
Fixed funnel leaks, added sales and marketing nurture, improved close rates
Buyout for <$10K
Founder Split Resolved
Managed conflict between 505 co-founders, structured amicable exit and executed founder buyout for under $10K
$4M Raised
Debt & Equity Capital
Guided investor outreach, financial storytelling and build investor models and materials
$1.2M Collected
Uncollected Funds Secured
Rebuilt A/R systems, chased down stale receivables and implemnented revised billing and collection processes

Sidekick Changes the Game for CEOs
We encourage you to speak to the CEOs we’ve helped. Our customers say, “I wish I found you a year earlier.”
Book a Strategy Call
+45% EBITDA
Revenue & Cost Reductions
?️ Restructured pricing, optimized team cost, and removed vendor waste
Raised $100M
Series B Financing
?️ Set foundation for mid market GTM that appealed to investors in crowded market
$26 Million Deal
Realized 14X EBITDA Multiple
?️ Created positioning, created competitive bidding process and drove internal training for leadership team
+$4M Revenue
$12M → $16M in 18 Months
?️ Rebuilt GTM, repositioned offering, and drove current customer expansion and growth of customer base
+$6M Revenue
$11M → $17M in 24 Months
?️ Changed core messaging, reworked sales targeting and differentiators versus growing competition
+$5M Revenue
$6M → $11M in 24 Months
?️ Replaced core sales and marketing leadership team, implemented performance management and drove client engagement model
Collect $900K Cash
Reduced Receivables with Core Customers
?️ Reworked billing process, changed pricing model and leveraged accounting systems and teams
Secured $1M LOC
Introduced and Closed Financing
?️ Enhanced financial presentation, trained leadership for presentation and negotiated terms
Reduce $3M Debt
Negotiated with Landlord
?️ Secured agreement to release, drove core team to secure alternative location
Saved $1.2M
Changed Product Development Plan
?️ Reworked development plan, changed IT vendors and accelerated go to market launch date
$125K Saved
Legal Dispute Reduced
?️ Resolved internal conflict with former employee, leveraged lower cost legal options and managed lawyer expenses
Saved $40K/Month
Marketing Cost Reduction
?️ Consolidated vendors, aligned spend to ROI and hired in house marketing resource
$2.5M Cash Flow
Via Pricing Overhaul
?️ Shifted to value-based pricing, re-negotiated renewals and increased average client size by $100K
3x Client Size
$15K → $45K Avg Deal
?️ Streamlined pricing, targeted different customer size and repositioned solution tiers
+$900K/Quarter
Client Revenue Growth
?️ Launched strategic upsell playbook, optimized retention and added more strategic marketing function
$2M Debt Removal
Lease Release Negotiated
?️ Structured landlord buyout and exit path with no payout on past liability
$375K Saved
Marketing Brought In-House
?️ In-housed team, rebuilt assets, and eliminated legacy agency spendign inefficiently on ad spend
4x Booking/Mth
$25K → $100K/Month
?️ Fixed funnel leaks, added sales and marketing nurture, improved close rates
Buyout for <$10K
Founder Split Resolved
?️ Managed conflict between 505 co-founders, structured amicable exit and executed founder buyout for under $10K
$4M Raised
Debt & Equity Capital
?️ Guided investor outreach, financial storytelling and build investor models and materials
$1.2M Collected
Uncollected Funds Secured
?️ Rebuilt A/R systems, chased down stale receivables and implemnented revised billing and collection processes
What CEOs of $5 to $25M Companies Say
We have helped hundreds of businesses just like yours raise money, grow revenue, differentiate, acquire customers, solve complex issues and scale.
What CEOs of $5 to $25M Companies Say
We have helped hundreds of businesses just like yours raise money, grow revenue, differentiate, acquire customers, solve complex issues and scale.

“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.”

“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.”

“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.”

“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.”

“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.”

“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.”

“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.”

“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.”

“The strategic decisions that TLE helped me make helped us beat the competition and saved us over $1 million in 12 to 18 months by guiding us to the right technology path.”

“My company has been growing and I needed to expand my role as CEO. What I learned from TLE is that those that have been there have insights I would have learned the hard way. It has resulted in more clients, more profitable clients and scalability.”