Episode 55

The Moment She Chose Risk Over a Real Job

Simple Social Marketing Agency w/ Arianne Hutcherson

What does it look like to build a marketing agency not just for freedom or profit, but to strengthen your community and provide for other families? In this heartfelt and honest episode of An Agency Story, host Russel Dubree sits down with Arianne Hutcherson, co-founder and president of Simple Social, to explore how she and her husband built their agency from scratch in Fort Myers, Florida…driven by mission, resilience, and a healthy dose of authenticity. From humble SEO beginnings to running a full-service marketing team, Arianne’s story is one of intentional growth, personal transformation, and letting go to truly lead.

The Moment She Chose Risk Over a Real Job

Episode Summary

In this episode, Arianne Hutcherson shares her path from freelancer to agency owner, and how Simple Social came to life during a make-or-break moment with her husband. The agency, built with a vision to support families and the local community, now serves businesses, nonprofits, and personal brands with services ranging from social media to video production. Arianne opens up about the emotional and logistical realities of growing a team, balancing marriage and business, and how Enneagram insights have helped her become a better leader.

Episode Highlights:

    • How freelancing as a blog writer turned into the foundation for a full-service agency
    • The “come to Jesus” moment that led to founding Simple Social with her husband
    • What it really means to let go and trust your team…down to handing over your phone for vacation
    • The Enneagram’s surprising role in her leadership style and team dynamics

Agency Info

Sometimes us even completely removing ourself from the picture is the best opportunity for our team to rise to the occasion.

Arianne Hutcherson

Key Takeaways

Authenticity is your best sales tool

Arianne shares how radical transparency, especially in early sales conversations, built trust and helped land their biggest client. Rather than pretending to be more established than they were, Arianne leaned into honesty. Her advice? “People can sense realness. Be truthful, and the right people will take a chance on you.”

Marriage and business: Define your lanes

Running an agency with her husband isn’t without its challenges, but Arianne and her partner have found success by staying in their own roles. With her creative and marketing experience and his strategic and sales strengths, they complement one another, avoiding conflict by not stepping on each other’s toes.

Delegation takes practice and personality awareness

As an Enneagram 2 (The Helper), Arianne struggled to let go of tasks and embrace the idea that others could do just as well, if not better, without her. By using tools like Asana and frameworks for training, she’s learned how to empower her team instead of over-functioning. “Sometimes the best way to help your team grow is to completely remove yourself from the process.”

Creating jobs can be your core purpose

For Arianne, success is not defined by scale or status, but by impact. Simple Social’s mission is to create sustainable income opportunities for their community and freelance network. “When we help businesses and nonprofits grow, we’re helping strengthen our community.”

Know when to truly unplug

Arianne’s boldest leadership move? Leaving her phone, with all client and work communication, with her team while on vacation. It’s not a stunt. It’s her way of modeling trust, balance, and boundaries.

Show Notes

Resources & Tools Mentioned:

  • Proposify: Proposal software used by Simple Social to streamline client presentations
  • Asana: Project management tool that supports task delegation and accountability
  • Enneagram Institute: Learn more about Enneagram personality types

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