The Confident Entrepreneur

Naples, FL

Contact for rates

Travels up to 200 miles

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From Expert to Author Podcast with Jennifer Ann Johnson

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The Art of Onboarding for Success

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The Entrepreneurial Edge

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Heartfelt Leadership

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Overview

Transform your event with proven entrepreneurial wisdom that drives real results.
Jennifer Ann Johnson brings 25+ years of success, including building a $50M+ empire. Amazon bestselling author and podcast host she's been featured on CNN, TIME, Real Simple, CNBC, Martha Steward among others. She delivers powerful presentations on authenticity, resilience, and women empowerment.
Why Choose Jennifer: Proven track record, media credibility, and authentic storytelling that transforms adversity into actionable strategies. Audiences leave inspired with concrete tools for meaningful change.


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Booking information

Price range: Contact for rates

Languages: English

Gig length: 30 - 120 minutes

What to expect

When you book Jennifer Ann Johnson for your event, you're securing a dynamic speaker who delivers transformational content rooted in 25+ years of authentic entrepreneurial experience. Your audience won't just hear theories, they'll learn from someone who has built multiple successful businesses while making a meaningful impact in her community.

Jennifer captivates audiences through compelling storytelling, and interactive elements that keep attendees engaged from start to finish. Her presentations are carefully crafted to balance inspiration with practical application, ensuring your audience leaves both motivated and equipped with actionable strategies.

As the founder of True Fashionistas (Florida's largest lifestyle resale store) and The Confident Entrepreneur brand, Jennifer shares genuine insights from building businesses from the ground up. Your audience will hear about real challenges, failures, pivots, and breakthroughs.

Every presentation includes proven frameworks and tools that attendees can implement right away. Jennifer focuses on practical solutions for common entrepreneurial challenges like overwhelm, decision paralysis, scaling struggles, and maintaining authenticity while growing a business.

Speaking as both a successful entrepreneur and mother of twins, Jennifer connects with audiences on the challenges of balancing ambitious business goals with personal values and community involvement. Her approach resonates particularly well with women entrepreneurs and small business owners seeking sustainable success.

1) Values to Operations: Build a Brand that Makes Every Decision Easier
Problem this course solves
• Marketing and hiring feel scattered; you attract misaligned customers; decisions are made “by the seat of your pants” with no clear roadmap.
Who it’s for
• Early-stage founders defining their brand, and established retailers who need to unify team behavior, customer experience, and marketing under clear values.
Key takeaways
• Define & rank core values using focused prompts (e.g., “What do you enjoy celebrating? What frustrates you?”) and turn them into a mission that guides real behavior.
• Operationalize values with “guideposts & guardrails” to drive consistent decisions, customer experience, and team engagement.
• Create a values report card + policies and a content plan to communicate values consistently across channels.

2) Customer Service & Culture: Turn Values into “Wow” Moments
Problem this course solves
• Inconsistent service and fuzzy culture standards lead to uneven customer experiences and team morale.
Who it’s for
• Store owners and teams who want a repeatable service ethos rooted in values, so every associate knows what “great” looks like.
Key takeaways
• Define service behaviors explicitly (e.g., “Customer service: sprinting the extra mile with enthusiasm and endurance”) and bake them into SOPs.
• Systematize service to reduce errors and speed response times; learn how standardized interactions boost satisfaction.
• Culture rhythms: communicate, display, and reinforce values so the brand shows up consistently for customers and staff.

3) Build a Business that Runs Without You (Time, Delegation, Systems, Automation)
Problem this course solves
• Owners are stuck in $10–$100 tasks, overwhelmed and unable to focus on $1,000-impact work (strategy, growth, sales).
Who it’s for
• Founders from startup to scale who want to reclaim time, delegate confidently, and implement systems that make the store run smoothly without constant owner input.
Key takeaways
• 14-day Time & Energy Audit to map where time goes, color-code energy drain, and categorize tasks (high-value, low-value, draining).
• Delegation playbook: ROI calculator, job descriptions, onboarding, and accountability (no micromanaging).
• Systems & automation: document repeatable steps; standardize customer service, sales, and ops; implement an “automation blueprint” for the next 30/60/90 days.

4) From Invisible to Influential: PR That Drives Real Opportunities
Problem this course solves
• Great businesses aren’t getting press because their digital storefront isn’t PR-ready, their story/targets are unclear, and outreach lacks structure.
Who it’s for
• Small businesses and retailers ready to professionalize their online presence and earn coverage that translates to traffic, trust, and sales.
Key takeaways
• Polish your digital presence: social media audit + website review to become “press-ready.”
• Craft your PR strategy: define SMART goals, your unique angle, and build a targeted media list.
• Make the first move: write winning pitches and press releases; master timing and follow-up.
• Amplify wins: add coverage to your site, social, and email; track impact with a simple toolkit.

What Event Planners Can Count On

Professional Excellence
With extensive media experience as host of "The Confident Entrepreneur" podcast and regular speaking engagements, Jennifer delivers polished, professional presentations every time. She arrives prepared, on time, and ready to exceed expectations.

Customized Content
Jennifer works closely with event planners to understand their audience, objectives, and desired outcomes. She tailors her presentations to address specific industry challenges, company cultures, or event themes while maintaining her authentic voice and proven frameworks.

Flexible Presentation Formats
Whether you need a 20-minute keynote, 60-minute breakout session, half-day workshop, or multi-session program, Jennifer adapts her content and delivery style to fit your event needs. She's equally comfortable with intimate groups of 20 or audiences of 2,000+.

Strong Audience Engagement
Jennifer's interactive presentation style ensures high audience participation and engagement. She incorporates Q&A sessions, small group discussions, and practical exercises that help attendees internalize and apply the content immediately.

Lasting Impact
Attendees consistently report that Jennifer's presentations provide clarity and actionable insights they continue using months after the event. Her practical frameworks and authentic approach create lasting behavioral change, not just temporary inspiration.

Comprehensive Event Support
Jennifer provides pre-event consultation to understand your goals, customized promotional materials for marketing, and post-event follow-up resources to help attendees implement what they've learned. She's committed to your event's success from planning through follow-up.

Ideal For These Audiences

- Entrepreneurial organizations and small business associations
- Women's business groups and leadership conferences
- Corporate teams focused on innovation and authentic leadership
- Industry associations seeking practical business growth strategies
- Educational institutions with entrepreneurship programs
- Chambers of Commerce and economic development organizations

The Jennifer Ann Johnson Difference

Unlike speakers who rely solely on motivational content or academic theory, Jennifer combines inspiration with implementation. Her unique background as a successful multi-business owner, podcast host, and community leader gives her credibility that resonates with diverse audiences.

Her authentic, no-nonsense approach helps attendees see past the glossy exterior of entrepreneurship to understand what really drives sustainable success: clarity of purpose, authentic relationships, strategic thinking, and the courage to stay true to your values while pursuing ambitious goals.

When you hire Jennifer Ann Johnson, you're not just booking a speaker, you're providing your audience with a mentor, strategist, and inspiration source who has walked the path they're traveling and can guide them toward their own version of authentic success.

About

Jennifer Johnson, founder of True Fashionistas, the largest lifestyle resale store in Florida is a renowned small business coach who empowers small businesses to achieve their goals without sacrificing their well-being. She has been an entrepreneur for over 25-years.

Once a national model and actress, she pivoted to build a $50 million+ resale empire with True Fashionistas, Florida's largest lifestyle resale store. Jennifer knows the struggle of juggling business growth, personal branding, and a life you love. That's why she built a roadmap for success, The Confident Entrepreneur. Now, Jennifer is a renowned coach, author of the Amazon bestseller "Grace & Grit: Becoming a Confident Entrepreneur", and host of the award-winning The Confident Entrepreneur podcast which was just name one of the top 100 female hosted podcasts in the country. She is a Gulfshore Life Businesswoman of the Year honoree, Small Business Association Emerging Leader, Distinguished Entrepreneur Nominee and Leadership Florida graduate.

Jennifer's expertise has landed her features on Inside Edition, Home Delivery, and countless national TV and radio shows. Jennifer has also spoken on countless national stages. Jennifer has been published in TIME Magazine, US News and World Report, The Associated Press, Newsweek, Vogue, CNBC, Martha Stewart and Real Simple, among others.

Additional booking notes

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