Stewart Ervin
Founder, Bracket Management • Business Turnaround & Growth Strategist
In Episode 141, Drewbie sits down with Stewart Ervin, founder of Bracket Management, to unpack what really separates struggling businesses from scalable, profitable companies.
Stewart specializes in business turnarounds, and this episode pulls back the curtain on how he helps owners diagnose problems, align teams, and create sustainable growth through numbers, playbooks, and leadership clarity.
From Stewart's early "sell-yourself-out-of-your-own-job" sales story, to deep dives on financial metrics, pricing strategy, cash flow, and operational alignment, this conversation is packed with real-world wisdom for business owners who feel stuck, overwhelmed, or capped by a growth ceiling.
If you've ever felt like your company is running you instead of the other way around—or you know your business should be more profitable than it is—this episode will give you the frameworks and mindset shifts you need to start turning the ship.
Stewart's wild early sales story that launched his turnaround career
Why numbers tell the truth when everything else lies
The first place Stewart looks when diagnosing a struggling business
Identifying misalignment between sales, operations, and finance
The most important financial metrics every business must track
Why cash flow—not revenue—is what kills growing companies
The real difference between branding, marketing, and sales
Why not every dollar is a good dollar
Breaking business segments down by margin, not just revenue
"Revenue is for vanity, profit is for sanity"
How pricing increases and cost reductions impact the bottom line
Why chasing revenue without margin leads to burnout
The danger of scarcity mindset decision-making
What business playbooks actually are (and why most companies don't have them)
Stewart's 6 core playbooks for building a scalable business
Why small, consistent improvements beat big "home run" changes
When founders hit growth ceilings—and why it happens
The hard truth about outgrowing early team members
Why every company must clearly define its "why"
How purpose beyond profit drives alignment and growth
Communication – Mission, vision, values, and clarity internally & externally
Forward Planning – Annual planning instead of reactive hindsight
Sales Funnel – Maintaining a 2–3x pipeline to avoid feast-or-famine cycles
Monthly Review – Aligning sales, operations, and forecasts in real time
People & Accountability – Roles, KPIs, incentives, and expectations
Value Creation – Pricing strategy, cost control, and new business growth
1. Numbers don't lie.
If something is broken in your business, it will show up in the financials.
2. Not every dollar is a good dollar.
High-revenue, low-margin work can quietly destroy your company.
3. Cash flow is king.
Growing too fast without cash planning is one of the fastest ways to fail.
4. Alignment beats hustle.
Sales, operations, and finance must move together—or everything breaks.
5. Playbooks create freedom.
Clear processes turn chaos into predictability and scale.
6. Small improvements compound fast.
A few percentage points across pricing, cost, and growth add up quickly.
7. Growth requires hard conversations.
What got you here won't get you there—especially with people.
8. Leadership ceilings are real.
Most founders hit them before they realize it.
9. Purpose fuels performance.
A "why" beyond profit rallies teams through tough seasons.
10. Systems build businesses—heroics burn them down.
🔗 LinkedIn: https://www.linkedin.com/in/stewartervin/
🌐 Website: https://bracketmgmt.com
📩 Newsletter: Available via LinkedIn
Stewart shares practical, no-fluff insights designed to help business owners stabilize, scale, and increase enterprise value.
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