From Hustling to Scaling: How Betsy Pepine Built 6+ Businesses Without Burning Out

From Hustling to Scaling: How Betsy Pepine Built 6+ Businesses Without Burning Out

What if the key to scaling your business wasn’t working harder—but choosing what only you should be doing?

That’s exactly what Betsy Pepine, founder of Pepine Realty, shared on the Scale Smart, Grow Fast podcast. She didn’t just build a successful real estate brokerage—she launched multiple complementary businesses including title, mortgage, property management, a real estate school, and a nonprofit.

Her secret? Letting go of the how, and finding the right who.

Listen to the full conversation on your favorite platform: [Spotify] | [Apple Podcasts]

🎯 Key Takeaways:

1. Start Where You Know, Then Build Out

Betsy expanded into services that aligned with her core business—title, mortgage, property management—not random ventures. Each business solved a specific need for her existing clients and agents.

2. Embrace the ‘Who Not How’ Mindset

Instead of doing everything herself (as many entrepreneurs do), Betsy shifted her focus:

“There are people who love to do what I don’t like to do. That changed everything.”

She stopped trying to master every role and started hiring people who already thrived in those areas.

3. Hire Before You’re Desperate

Waiting until you’re overwhelmed to bring in help is a recipe for burnout. Betsy recommends proactively forecasting hiring needs each quarter—especially for roles like executive assistants or operators.

4. Culture Is Strategy

From personalized recognition to peer-to-peer shoutouts using tools like Motivocity, Betsy has built a workplace culture that retains top talent. Core values like growth mindset and family are deeply woven into daily operations.

5. Let Go to Grow

Stepping out of daily operations wasn’t easy—Betsy admits to emotional challenges and team turnover. But putting an operator in place gave her the space to focus on vision, strategy, and doing what she loves. Her advice?

“Do a time audit. Hand off what doesn’t bring you joy or align with your strengths.”

📚 Recommended Resources:

  • Who Not How – Dan Sullivan & Ben Hardy
  • 10x Is Easier Than 2x – Dan Sullivan & Ben Hardy
  • Traction – Gino Wickman
  • Scaling Up – Verne Harnish
  • Groups like EO and Vistage

🔹 Want to scale smarter?
You don’t have to build your business alone. Our AI-leveraged executive assistants at Workergenix help you delegate the busywork, streamline operations, and stay focused on what truly drives growth—your vision.

Schedule a free discovery call and take the first step toward building a high-performing team and a business that runs without burning you out.

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The Systems That Give You More Time and Freedom

The Systems That Give You More Time and Freedom

Most entrepreneurs start their businesses for freedom—freedom of time, financial independence, and the ability to work on what they love. But as your business grows, so does the workload. Instead of gaining time, many business owners find themselves buried in tasks, stuck managing operations instead of leading growth.

In a recent episode of the Scale Smart, Grow Fast Podcast, we sat down with Stephanie Cabral, a former attorney turned real estate entrepreneur, to discuss how she scaled her business efficiently without sacrificing quality or control.

Listen on the go! Catch the full episode on your favorite podcast platform:

🎧 Spotify
🍏 Apple Podcasts

The Mindset Shift: Treating Your Business Like a Business

One of the biggest mindset shifts Stephanie made was realizing that real estate investing—or any business—is not a side hustle, it’s a company. If you want to scale, you can’t run your operations manually forever.

She stopped managing everything herself and implemented automation and delegation.
She focused on systems that could scale, not just processes that worked in the moment.
She prioritized high-impact work instead of getting stuck in daily tasks.

How Systems and Delegation Transformed Her Business

Stephanie knew she couldn’t scale while handling every invoice, repair call, and tenant request. So she built a structured system for efficiency by:

🔹 Using automation tools to manage communication, invoicing, and workflows.
🔹 Hiring a dedicated assistant to take over administrative tasks, freeing her time for strategy.
🔹 Implementing SOPs (Standard Operating Procedures) to ensure consistency and eliminate micromanagement.

This shift allowed her to focus on growing her portfolio, securing better deals, and expanding her impact—all while working less.

How You Can Apply This to Your Business

No matter your industry, these principles apply. If you’re feeling stuck in daily operations, ask yourself these questions:

🔸 What tasks do I repeat every day that could be automated?
🔸 What low-value tasks am I holding onto that someone else could handle?
🔸 Where am I spending time that isn’t directly growing my revenue?

The key to scaling smart is removing yourself as the bottleneck. With the right systems and support, you can grow your business without working 24/7.

Want to Scale Faster Without Burnout?

If you’re ready to free up your time and focus on what truly moves the needle, it’s time to build a smarter, more efficient business. Watch the full podcast episode now and start implementing the strategies that will help you grow without the overwhelm.

Ready to streamline your business and reclaim your time? Schedule a discovery call today and see how the right systems and support can help you scale smarter and grow faster.

Like what you read? Get weekly insights on scaling, efficiency, and profitability—straight to your inbox. Click here to subscribe.

How Are Smart Investors Scaling Without Adding More Work?

How Are Smart Investors Scaling Without Adding More Work?

Growing a business—especially in real estate—often comes with an unexpected challenge: the more successful you become, the more work you have on your plate. Managing properties, handling bookkeeping, coordinating maintenance, and keeping investors engaged can quickly consume your time. But what if scaling didn’t have to mean working more hours?

In a recent episode of the Property Profits Real Estate Podcast, host Dave Dubeau sat down with real estate investor and digital nomad Harley Green to discuss how he built a thriving real estate portfolio while traveling the world. The secret? Leveraging remote teams and systems to run his business efficiently without being trapped in daily operations.

The Hidden Bottleneck That Slows Down Growth

Many real estate investors hit a wall when they try to scale. They assume that taking on more deals means handling more tasks themselves. Instead of focusing on revenue-generating activities—like acquiring properties or building investor relationships—they get stuck in:

Tenant & Guest Management – Handling bookings, maintenance, and guest communications.
Bookkeeping & Financial Tracking – Manually tracking expenses, invoices, and rental income.
Marketing & Investor Outreach – Posting listings, managing social media, and creating reports.

For Harley, this realization came early when he was juggling a full-time job, a growing portfolio, and family life. Instead of working 80-hour weeks, he built a remote team to take on the daily tasks, freeing him to focus on high-value decisions.

How Systems & Remote Support Changed Everything

By implementing a strategic approach to delegation, Harley now has a fully optimized real estate business that runs efficiently while he focuses on growth. Here’s how he did it:

🔹 Clear Role Assignments – Every task, from tenant inquiries to bookkeeping, is assigned to a team member with the right expertise.
🔹 Standard Operating Procedures (SOPs) – Documented processes ensure consistency and efficiency, even as the team grows.
🔹 Technology & Automation – Tools like Monday.com, Google Drive, and ChatGPT streamline workflows and eliminate unnecessary manual work.
🔹 A Strong Team Culture – Virtual team meetups and ongoing training ensure engagement and long-term retention.

What This Means for Business Owners & Investors

Harley’s approach isn’t just for real estate—it applies to any entrepreneur who wants to scale without burnout. Whether you run a real estate firm, a service-based business, or a consulting agency, delegating non-revenue-generating tasks allows you to focus on strategy and business growth.

More time for deal-making and client relationships
Improved efficiency with streamlined operations
Less stress and better work-life balance

If you’re ready to stop working in your business and start working on it, take a page from Harley’s playbook. Build the right systems, delegate effectively, and focus on growth—not the daily grind.

Like what you read? Get weekly insights on scaling, efficiency, and profitability—straight to your inbox. Click here to subscribe.