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Most entrepreneurs get stuck at $5M because they're trapped in a job. They are working IN the business more than ON the business. Here's the systematic approach that changes everything: Turning that “job” into a true asset. Have your expertise do the work. And systemize, systemize, systemize. Let’s start.

You've built a successful business. You're generating $2-5 million in annual revenue, and from the outside, everything looks great. But on the inside? You're drowning.

You're working 70-hour weeks, constantly putting out fires, and feeling like the bottleneck in your own company. Every vacation turns into a disaster, and you've realized that your business has become a prison instead of the freedom machine you originally envisioned.

Sound familiar? You're experiencing what I call the "$5M Ceiling Crisis" – and you're not alone. 89% of businesses struggle to systematically scale beyond this point.

The counterintuitive truth? The lean operational approach that got you to $5M is the exact thing preventing you from reaching $10M. But the solution isn't to abandon your preference for efficiency – it's to hire strategically.

The Founder's Dilemma: Helpers vs. Leaders

Here's where most entrepreneurs make their fatal mistake. When growth stalls, they think, "I need help," so they hire more assistants, more task-doers, more people who need constant direction.

This creates what I call the "Helper Trap" – suddenly you're managing 15 people instead of doing the work, but you're still the decision-maker for everything. You've traded being a productive genius for being a frazzled middle manager.

The breakthrough insight: You don't need more helpers. You need leaders who can own specific outcomes without your constant oversight.

The difference is profound:

  • Helpers say, "What should I do next?"

  • Leaders say, "Here's what I'm going to do next."

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The Strategic Five: Your Path from $5M to $10M

After analyzing hundreds of businesses that successfully broke through the $5M ceiling, a clear pattern emerges. They systematically hired five specific leadership roles in a particular order. Not all at once (that would destroy your lean culture), but strategically, one bottleneck at a time.

Role #1: Executive Assistant/Chief of Staff

Why this comes first: Before you can effectively lead other leaders, you need to reclaim your most valuable asset – your time and mental bandwidth. This is the foundation that makes all other strategic hires possible.

Key Responsibilities:

  • Manages your calendar and priorities strategically

  • Acts as a gatekeeper for your attention

  • Coordinates between department heads

  • Handles high-level administrative functions

  • Protects your focus for CEO-level work

Key Metrics:

  • Hours per week you spend on high-level strategy vs. operations

  • Number of unnecessary meetings eliminated

  • Response time on critical decisions

  • Time freed up for strategic thinking

The Common Mistake: Hiring a virtual assistant or someone who needs constant direction. You need a professional who can manage your executive function better than you can – think Chief of Staff in training, not administrative helper.

Role #2: Head of Marketing

Why this comes second: With your time protected by your EA, you can now focus on building the engine of your business. Everything flows from lead generation – if you don't have a predictable system for generating attention and leads, you don't have a scalable business.

Key Responsibilities:

  • Owns overall brand awareness and positioning

  • Manages the entire lead generation funnel

  • Responsible for traffic growth and lead quality

  • Develops content strategy and messaging

Key Metrics:

  • Website visitors and traffic sources

  • Leads generated monthly

  • Customer Acquisition Cost (CAC)

  • Return on Ad Spend (ROAS)

The Common Mistake: Thinking you can outsource this entirely to an agency. While agencies execute tactics, you need someone internally who owns the strategy and understands your business deeply enough to make real-time adjustments.

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Role #3: Head of Sales

Why this comes third: If marketing fills the funnel, sales pulls the money out. With your time protected and lead generation systematized, you can now focus on converting those leads into predictable revenue.

Key Responsibilities:

  • Owns the entire sales pipeline and process

  • Manages proposal creation, pricing strategy, and follow-up systems

  • Builds scalable sales systems that work without you

  • Trains and develops sales team members

Key Metrics:

  • Close rate and conversion percentages

  • Average Order Value (AOV)

  • Sales cycle length

  • Revenue per salesperson

The Common Mistake: Promoting your best salesperson to sales manager. Great players rarely make great coaches. You need someone who can build systems, not just close deals.

Role #4: Head of Product/Fulfillment

Why this comes fourth: With leads flowing and sales converting, you now need someone to ensure you can deliver on all those promises. This person keeps the commitments that marketing and sales make to your customers.

Key Responsibilities:

  • Ensures consistent, high-quality delivery

  • Manages client fulfillment and experience

  • Builds scalable systems for service delivery

  • Maintains quality standards as volume increases

Key Metrics:

  • Net Promoter Score (NPS)

  • Client retention rate

  • Delivery margin and profitability

  • Time to deliver

The Common Mistake: Promoting your most experienced technician. Technical expertise doesn't equal leadership ability. You need someone who can systematize delivery without losing the human touch.

Role #5: Head of Finance & Operations

Why this comes last: With your core business functions running smoothly, you need sophisticated financial leadership to optimize profitability and prepare for your next growth phase.

Key Responsibilities:

  • Financial planning, budgeting, and forecasting

  • Cash flow management and runway analysis

  • Operational efficiency and cost optimization

  • Strategic financial insights and reporting

Key Metrics:

  • Net profit margin

  • Cash on hand and runway

  • Budget variance

  • Operational efficiency ratios

The Common Mistake: Thinking your bookkeeper or tax CPA can fill this role. You need a strategic financial leader who can analyze trends and provide actionable insights, not just record transactions.

The Strategic Hiring Sequence

The order matters more than you think. Here's the systematic approach that actually works:

Step 1: Hire Your Executive Assistant First This seems counterintuitive, but it's the most crucial hire. You can't effectively lead other leaders when you're drowning in operational tasks. Your EA creates the space you need to think strategically and manage a leadership team.

Step 2: Identify Your Revenue Bottleneck With your time protected, now ask: Is your business demand-constrained or supply-constrained?

  • Demand-constrained? You need more leads and customers. Hire Head of Marketing next.

  • Supply-constrained? You have more leads than you can handle. Skip to Head of Product/Fulfillment.

Step 3: Complete Your Revenue Engine If you hired marketing, follow with sales. If you hired fulfillment first, now add marketing and sales in sequence. The goal is to have a complete lead-generation-to-delivery system.

Step 4: Scale Your Operations With revenue flowing predictably, hire your Head of Product/Fulfillment (if you haven't already) to ensure quality delivery at scale.

Step 5: Add Financial Sophistication Finally, bring in financial leadership to optimize profitability and prepare for advanced growth strategies.

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The Focus Card: Your Implementation Tool

Here's where most strategic frameworks fail: they give you the theory but leave you hanging on execution. That's why every business that successfully scales using this approach implements it through a proven tool called the Focus Card.

The Focus Card is the operational backbone that transforms strategic hiring from a concept into a measurable system. It's a simple but powerful one-page tool that ensures every new leader you hire is aligned with your priorities and accountable for specific outcomes.

How the Focus Card works:

Every Monday: Your entire leadership team looks at the Focus Card and reports their top priorities for the week. Each department head (Marketing, Sales, Product, Finance) commits to specific, measurable outcomes that directly support your path to $10M.

Every Friday: The same team reconvenes to review the Focus Card, examining this week's results and extracting insights. What worked? What didn't? What do we need to adjust for next week?

This simple Monday-Friday rhythm creates what we call "intelligent iteration" – your leadership team gets smarter every single week, and course corrections happen in days instead of quarters.

The beauty of the Focus Card is that it solves the biggest challenge of strategic hiring: ensuring your new leaders are actually leading instead of just occupying expensive positions.

You can download the Focus Card for free at strategysprints.com and start implementing this system immediately, even before you make your first strategic hire.

The $10M Transformation

Here's what happens when you execute this framework correctly with the Focus Card system:

Months 1-3: Initial adjustment as you learn to work with your EA and delegate effectively. You'll be tempted to micromanage, but resist. The Focus Card keeps everyone aligned during this crucial transition period.

Months 3-6: Systems start to stabilize. You begin to see the first glimpses of what it feels like to work ON your business instead of IN it. The weekly Focus Card rhythm becomes natural, and your leaders start anticipating problems instead of just reacting to them.

Months 6-12: Exponential improvement. With leaders owning specific outcomes and the Focus Card providing weekly accountability, you can focus on strategy, partnerships, and the activities that actually move the revenue needle.

Year 2 and beyond: Your business becomes a true asset instead of a job. You can take real vacations, pursue new opportunities, and watch your company grow without your constant presence. The Focus Card system runs itself, with your leadership team continuously optimizing performance.

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The Strategy Sprints Advantage

At Strategy Sprints, we've refined this process into a systematic methodology that allows you to implement these hires strategically without destroying your lean culture or cash flow.

Our clients typically see:

  • 32% average revenue growth in the first year

  • 14 hours per week freed up for strategic work

  • 50% reduction in founder-dependent processes

  • 98% report significant improvement in work-life integration

The key is having a proven framework that tells you exactly when to hire, what to look for, and how to integrate each leader without losing the entrepreneurial culture that got you this far – all supported by the Focus Card system that ensures execution happens consistently.

Your Next Step

Building a $10M business isn't about working harder or finding magical unicorn employees. It's about systematically transitioning from being the person who does everything to being the person who leads the people who do everything.

The question isn't whether you should hire these roles – it's whether you'll hire them strategically or continue to struggle with the helper trap until your competition passes you by.

Start today: Download the Focus Card at strategysprints.com and begin implementing the weekly rhythm that will support your strategic hiring process. Even if you haven't made your first leadership hire yet, this tool will help you think like a CEO and prepare for the transformation ahead.

If you're ready to break through your revenue ceiling and build the leadership team that will scale your business to $10M and beyond, that's exactly what we help entrepreneurs accomplish through our Strategy Sprints methodology.

Want to see how this applies to your specific situation? Let's talk about building your strategic hiring plan and creating the systems that will support your new leadership team.

About the Author: As the CEO of Strategy Sprints, I've helped create over $2B in additional sales for clients over 21 years. I've seen hundreds of entrepreneurs break through the $5M ceiling – and I know exactly what separates those who succeed from those who stay stuck.

Sprinters from LA to Dubai meet 24/7 to share what’s working right now in marketing and sales.

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