Scrappy but Successful: Ep. 1 The Lesson That Changed How She Runs Her Business with Cassandra D'Alessio

I pull up a chair with Cassandra D’Alessio, founder and Chief Content Strategist at Next Page Brand Strategies, for a conversation that proves most successful consulting businesses don’t start polished, they start scrappy.

Cassandra shares how growing up constantly moving, working early retail jobs, navigating teaching, corporate life, and eventually launching her own business all built the adaptability she relies on today. The conversation moves from early career missteps and confidence-building moments to lessons learned from tough clients, contracts, and figuring out how to grow a business without losing your sanity in the process.

Along the way, we trade stories, laugh through rapid-fire personality questions, and unpack how storytelling and data work together to help businesses make smarter decisions. It’s honest, funny, and packed with relatable moments for anyone who’s ever wondered if everyone else is secretly figuring it out as they go too.

What Comes Up When Consultants Talk Shop

• Cassandra’s unconventional path from teaching to entrepreneurship

• How constant relocation as a child built scrappiness and adaptability

• Early career jobs that shaped her work ethic (including floral and liquor store retail)

• Lessons learned from difficult client relationships and enforcing contracts

• Why onboarding meetings still matter in person

• Inbox management and personal productivity habits

• How marketing storytelling and analytics work together

• Cassandra’s approach to content strategy for service businesses

• A rapid-fire look at consultant personalities and working styles

The Stories Behind the Success

One of the defining influences in Cassandra’s story was growing up in a family that moved every few years due to her father’s career. Being “the new kid” repeatedly forced her to adapt socially and emotionally, skills that later translated directly into entrepreneurship, where constant change is the norm.

Another standout moment comes from Cassandra’s early business struggles, especially learning to set boundaries with clients. She shares a rare experience where she had to enforce contract terms with a difficult client who wanted to leave early. It was uncomfortable but ultimately reinforced the importance of protecting both her business and her team.

And perhaps the most relatable story: Cassandra admitting she’s still figuring things out (payroll, operations, and leadership included) even after years in business. A reminder that success rarely feels polished from the inside.

Scrappy Moves You Can Steal

Put Boundaries in Writing Early

Scrappiness helps you win early clients, but long-term success comes from clear agreements. Make sure your contracts spell out scope changes and payment terms so you’re not stuck doing unpaid work later.

Know Your Audience Before You Market

Whether you’re teaching a classroom or marketing a business, results come from understanding what your audience actually cares about. Stop guessing. Ask questions, watch behavior, and tailor your message to what they need.

Use Systems to Protect Your Time

Simple systems like calendar scheduling tools, inbox organization, and follow-up processes keep your business from running you. Structure reduces stress and frees you up to focus on higher-value work.

Confidence Comes From Doing, Not Waiting

Most successful consultants didn’t feel ready when they started. Action builds confidence. Start before you feel fully prepared and let experience close the gap.

Let’s Look At The Data 

A key insight in this episode is Cassandra’s view that data tells a story about people. From early experiences watching Google Analytics evolve to today’s AI-driven search behavior, she highlights how data reveals what customers actually want, sometimes contradicting instinct.

For Cassandra, successful marketing blends narrative and numbers: storytelling builds connection, while analytics show what’s actually working. The real power comes when businesses use both together to guide decisions.

About Cassandra

Cassandra D'Alessio is the founder and Chief Content Strategist of Next Page Brand Strategies, a Charlotte-based agency supporting small businesses since 2017. With a B.A. in Creative Writing from Miami University of Ohio and M.A. in English Literature from the University of Louisville, she has studied the power of words for over two decades. 

Before launching her agency, Cassandra taught at multiple colleges including UNC-Charlotte as a Visiting Lecturer (2010-2016) and served as Director of Marketing for a Charlotte nonprofit. She is the author of This Won't Be Pretty: First Year Lessons for the Female Entrepreneur (2020).

Cassandra believes that in our content-saturated digital world, consumers support brands that seek to make genuine connections. Through strategic storytelling and meaningful content, she helps small businesses build authentic relationships with their audiences. 

When not working, she enjoys time with her husband, young daughter, and their energetic dog.

Learn more about Cassandra and connect at https://www.turnthenextpage.com/