She's That Founder: Stop Being The Bottleneck and Lead Smarter with AI

Do you feel like you're stuck in a cycle of transaction after transaction, struggling to build lasting connections in your business? Or maybe you're unsure how to identify the right opportunities to grow your company into something more aligned with your vision?

In today’s episode of My Good Woman, I sit down with Jessy Grossman, founder of Women in Influencer Marketing (WIM), who built a thriving agency from scratch by spotting untapped market opportunities. Jessy shares her journey of shifting from a transactional business model to creating a powerful, community-first organization, and the lessons she learned about listening to her audience, aligning with the right partners, and trusting her gut.

If you’re ready to stop chasing quick wins and start building a sustainable, fulfilling business that’s driven by authentic connections and smart strategies, this episode is packed with actionable insights that will help you get there.

Stay tuned as we explore the mindset shifts, strategies, and big wins that will empower you to take your business to the next level!

In this episode, you’ll learn …

• How to build a community-driven business that fuels long-term growth.
• How to trust your instincts to create a business aligned with your vision.
• How to build resilience and adapt when facing unexpected business challenges.

This episode at a glance:

[2:45] – Jessy’s journey from commercial talent representation to influencer marketing

[12:10] – The birth of Women in Influencer Marketing (WIIM) and why community matters in business

[20:15] – The differences between an influencer talent agency and a networking organization

[55:33] – Jessy’s advice to female founders: Trust your gut and expand beyond your comfort zone

Resources and Links mentioned in this episode

• Jessy Grossman 
• Women in Influencer Marketing (WIIM)
• Free Range Thinking
• Tools Mentioned: Zapier, Common Room
• Join Female Founder Society

You might also like

• The Power of Community In Tough Times 
• THE BOOST AI Strategy Framework
• 8 Strategies for Niche-Bound Businesses

More about the “My Good Woman” podcast

My Good Woman is a podcast for new and future female leaders, hosted by me, Dawn Andrews.

Grab a seat at the table with me each week for candid conversations with culture-shifting, glass ceiling-busting, trailblazing women, who are leading enterprises that are making a change in the world. 

We discuss what makes them tick and how they get it all done. And we share actionable strategies to help you and your team get organized - so you can focus on your company’s growth, profit, and impact. 

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Big News Alert, Fabulous Leaders! 

Dawn Andrews here, and today I’m bringing you something bittersweet but oh-so-exciting. After 63 amazing episodes of "My Good Woman," we’re stepping into a brand-new era together. 

Yep, it’s official: we’re rebranding!

Say hello to She’s That Founder—the next evolution of the podcast you’ve come to love. But don’t worry, we’re keeping all the juicy bits you adore: practical tips, real-talk advice, and incredible founder stories. 

What’s changing? We’re getting laser-focused on helping you step into your power as a founder, CEO, and game-changer. 

What to Expect:

• More stories of female entrepreneurs shaking up their industries and owning their space.
• Tactical tips to help you transform your biz from good to legacy-level great.
• Real talk on leadership, visibility, and creating lasting impact.
• This isn’t just a name change—it’s a movement. We’re diving deeper, growing bolder, and aiming higher. This space is for the founder who wants more than just success—it’s for the woman who’s here to change the world. 

Here’s to stepping fully into our power and owning our space as that founder. Let’s do this together.

PS: Get all the details on our Insta, YouTube, and email list so you don’t miss a thing. Because if you’re a founder with a bold vision, this is your space. Let’s GO!

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Are your hiring decisions costing you time and money? 

The truth is, building a high-performing hybrid team is the key to saving resources and boosting productivity. When you bring the right people on board, you’ll not only prevent costly communication breakdowns but also create a cohesive team that collaborates effortlessly—even across time zones.

In this episode, I’m breaking down 6 strategies to hire smarter, foster a culture of collaboration, and boost your team’s efficiency. You’ll learn how to prevent turnover, improve client relationships, and unlock your team’s hidden potential using my secret weapon: the People Reading Guide. 

If you're ready to stop micromanaging and start growing your business, this episode is your game-changer.

In this episode, you’ll learn

• How to hire the right people for your hybrid team without wasting time or money. 
• The six step strategy for building a high performing remote team. 
• Leveraging the People Reading Guide to increase team productivity.

This episode at a glance:

[2:15] - Reflecting on how the pandemic changed the workplace permanently

[8:45] - Six reasons hiring right is the foundation for team success

[12:12] - How to ensure effective communication in a remote work environment

[20:05] - An example of how the "People Reading Guide" helped a consultancy improve team dynamics

Resources and Links mentioned in this episode

• Free Range Thinking
• Dawn Andrews
• People Reading Guide
• Join the Female Founder Society
• Visit our website

You might also like:

• 8 Strategies for Niche-Bound Businesses
• Crafting Your Business Identity and Personal Branding
• 3 Ways To Set Focused Goals For Intentional, Sustainable Business Growth

More about the “My Good Woman” podcast

My Good Woman is a podcast for new and future female leaders, hosted by me, Dawn Andrews, founder of Free Range Thinking, "My Good Woman" is for new and aspiring female leaders. Join me each week for candid chats with trailblazing women breaking barriers and leading impactful businesses. We dive into what drives them and share practical tips to help you streamline

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

What happens when a successful entrepreneur, fierce advocate for women’s health, and accidental CEO takes the helm of a game-changing business? 

In this episode, Dr. Catherine Birndorf, founder of The Motherhood Center, shares the challenges of scaling a business in the healthcare industry while staying true to her mission.

If you think running a business is tough, wait until you hear how she’s reshaping the maternal mental health landscape, one bold decision at a time. From navigating the complex realities of entrepreneurship to creating a sanctuary for women struggling with perinatal mental health, her story is full of insights for business owners who are ready to step up as visionary leaders.

This episode is a must-listen for any woman ready to own her mission, tackle challenges head-on, and scale her business while making a lasting impact.

In this episode, you’ll …

• Learn how to stay focused and resilient during the toughest phases of business growth.
• Discover how to scale your business while staying true to your core mission.
• Get actionable advice on balancing the demands of leadership with personal well-being
• Learn how building a strong support network—both professionally and personally—can accelerate your business success .

This episode at a glance:

[3:30] - Dr. Birndorf introduces her journey into reproductive psychiatry and founding The Motherhood Center.

[32:25] - How female founders can build resilience and mental health support while managing the stress of building a business.

[45:55] - The transition from being a practicing psychiatrist to stepping fully into the CEO role, and the lessons Dr. Birndorf learned along the way.

[1:10:30] - Dr. Birndorf shares her personal self-care strategies, including therapy, meditation, and family time, to maintain balance.

Resources and Links mentioned in this episode

• The Motherhood Center
• Dr. Catherine Birndorf
• Free Range Thinking
• Join Female Founder Society

You might also like

• It’s Time To Start Your Own Business 
• The Power of Community In Tough Times 
• How to Stop Burnout as a Female Founder

More about the “My Good Woman” podcast

My Good Woman is a podcast for new and future female leaders, hosted by me, Dawn Andrews, founder of Free Range Thinking, "My Good Woman" is for new and aspiring female leaders. Join me each week for candid chats with trailblazing women breaking barriers and leading impactful businesses. We dive into what drives them and share practical tips to help you streamline

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Are you tired of sales feeling like a never-ending game of cat and mouse? 

In this episode, I’m spilling the beans on how to close deals faster by understanding your client’s unique buying type. I’m talking about transforming those ho-hum pitches into irresistible offers that cut your sales cycle in half and pump up your profits. 

You’ll also get the inside scoop on the psychological triggers that turn casual interest into a firm "Yes!"—and why ignoring them is like leaving money on the table.

But wait, there’s more! I’m pulling back the curtain on the DISC sales assessment, a secret weapon that lets you tailor your approach to connect with your clients on a deeper level. I’m sharing real-world stories of how understanding my style and my client’s style boosted my close rate by 30%—and made selling feel less like pulling teeth and more like second nature. 

Tune in, and get ready to turn those leads into loyal client who can’t wait to say, "Yes, please!"

In this episode, you’ll learn

• How to close deals faster and the secret to shortening your sales cycle by tailoring your pitch to match your client’s buying type.
• The key psychological triggers that turn potential leads into loyal clients and how to leverage them effectively.
• How to use the DISC framework to customize your sales approach and connect with your clients on a deeper, more personal level.

This episode at a glance:

[2:15] - Introduction to psychological triggers in sales: Why understanding what makes your clients tick is essential.

[8:30] - DISC Sales Assessment explained: Dominance, Influence, Steadiness, and Conscientiousness types decoded.

[15:45] - Real-world example: Tailoring a sales pitch to a conscientious client and the impact on closing the deal.

[22:00] - Benefits of aligning your sales style with your client's personality: Reducing miscommunication and increasing sales success.

Resources and Links mentioned in this episode

• Dawn Andrews
• People Reading Guide
• How to Use DiSC Behavioral Styles
• Check our BLOGS 

You might also like:

• 8 Strategies for Niche-Bound Businesses
• How to Not Fail in Your First Year in Business
• Business Goals Workbook

More about the “My Good Woman” podcast

My Good Woman is a podcast for new and future female leaders, hosted by me, Dawn Andrews, founder of Free Range Thinking, "My Good Woman" is for new and aspiring female leaders. Join me each week for candid chats with trailblazing women breaking barriers and leading impactful businesses. We dive into what drives them and share practical tips to help you streamline operations, grow your company, and boost profits. Don’t forget to follow and leave a review! 

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Ever wondered what it really takes to build a business from scratch?

In this episode, you'll get a peek behind the curtain as I coach Rebecca, a budding entrepreneur, through the gritty, real-life challenges of starting her personal training and wellness business. 

During the session, we're using a personal branding document alongside ChatGPT to help Rebecca create her bio and ideal client avatar. We're in step two of my Founder Success System business building process.

You'll hear us answer specific questions and take occasional pauses as we work through the intricacies of defining a brand that aligns with Rebecca's mission and audience. We'll unpack the importance of being clear over clever in branding and how the right bio can transform your engagement with your ideal client. Plus, you'll hear actionable strategies to create authentic content that speaks directly to the heart of your audience using prompts with ChatGPT. 

Tune in and get inspired to push your business to extraordinary heights!

In this episode, you’ll learn

• How to craft a business identity that aligns with your values and lifestyle to connect more deeply with your audience.
• How to season AI tools like ChatGPT to create compelling bios, client avatars, and authentic content that speaks directly to your target market.
• How a well-defined bio can significantly enhance your engagement with ideal clients.
• How to define your unique value proposition, create your bio, and outline your ideal client avatar, 

This episode at a glance:

[3:45] Discussing the importance of a company name and brand's unique value proposition.

[10:50] Using a personal branding document and ChatGPT to create a bio and ideal client avatar.

[15:25] The significance of being clear over clever in branding.

[20:00] Actionable strategies for creating authentic content that resonates.

Resources and Links mentioned in this episode

• Dawn Andrews
• Free Range Thinking
• TOOLS: Chat GPT
• Book a consultation with us!

You might also like:

• Power Up Your Mid-Year Review With Your Secret Sauce
• 3 Essential Strategies for Expanding Your Business
• Business Goals Workbook

More about the “My Good Woman” podcast

Grab a seat at the table with me each week for candid conversations with culture-shifting, glass ceiling-busting, trailblazing women, who are leading enterprises that are making a change in the world. 

We discuss what makes them tick and how they get it all done. And we share actionable strategies to help you and your team get organized - so you can focus on your company’s growth, profit, and impact. 

If you liked what you heard, don’t forget to follow along, so you never miss an episode. And before you go, leave us a review - it would mean a lot to us!

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Picture this: a teenage passion turning into a global empire, complete with the rollercoaster of entrepreneurial highs and lows. 

In this episode, Octavia Gilmore, founder of Creative Juice, dishes on everything from bouncing back after a soul-crushing review to harnessing the power of AI to skyrocket her business. She spills the tea on the magic of a multicultural team, the real-deal challenges of scaling up, and how empathy and compassion are the secret sauce to leadership. 

Whether you're a startup dreamer or a seasoned CEO, Octavia's journey is packed with gold nuggets you won't want to miss.

In this episode, you’ll …

• Uncover the 3 game-changing steps to transform from a solo freelancer to a powerhouse business owner.
• Unlock the secrets of entrepreneurial resilience and learn how to bounce back stronger after setbacks.
• Explore innovative AI tools to transform your business processes and efficiency.

This episode at a glance:

[2:12] - Octavia shares her early passion for graphic design and launching Creative Juice at 23.

[15:48] - Overcoming self-doubt and learning essential business concepts.

[45:18] - Resilience in entrepreneurship: Learning from setbacks and negative reviews.

[1:00:37] - Octavia’s goal to inspire young black and brown entrepreneurs.

[1:05:28] - Encouragement for female founders: Eliminating self-limiting beliefs and taking bold steps.

Resources and Links mentioned in this episode

• Octavia Warren
• Creative Juice
• Chroma Creators
• Free Range Thinking
• AI Tool Highlight: CHAT GPT
• Join Female Founder Society

You might also like

• Expand Your Reach: 8 Strategies for Niche-Bound Businesses
• The AI Blueprint Strategy for Female Entrepreneurs Ready
• Boost AI Strategy Framework

More about the “My Good Woman” podcast

My Good Woman is a podcast for new and future female leaders, hosted by me, Dawn Andrews.

I’m a happily married hockey mom, proud female leader, and founder and CEO of Free Range Thinking, where we turn founders into confident CEOs with strategic consulting and leadership training.

Grab a seat at the table with me each week for candid conversations with culture-shifting, glass ceiling-busting, trailblazing women, who are leading enterprises that are making a change in the world. 

We discuss what makes them tick and how they get it all done. And we share actionable strategies to help you and your team get organized - so you can focus on your company’s growth, profit, and impact. 

If you liked what you heard, don’t forget to follow along, so you never miss an episode. And before you go, leave us a review - it would mean a lot to us!

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Did you know that listening could be your superpower in business?

In this episode we’re celebrating World Listening Day by exploring the incredible impact of active listening on your business and personal life. 

Learn how this essential skill can boost your client connections, strengthen your team’s productivity and morale, and help you manage conflicts with empathy and effectiveness. I’ll give you practical tips to enhance your listening abilities and invite you to join a community of exceptional female leaders striving for excellence together.

Can you actively listen today? Tune in! 

In this episode, I discuss:

• How to use active listening to understand clients and provide tailored solutions.
• How to enhance team dynamics: to foster trust and collaboration for increased productivity and morale.
• How to navigate conflicts with empathy and effectiveness.
• Practical Tips: Improve your listening skills with mindfulness, nonverbal cues, and reflexive listening.

This episode at a glance:

[01:27] Did you know that mastering the art of listening can be the key to unlocking unprecedented growth in your business?

[04:08] We are  in some incredibly vitriolic and contentious times. And I feel like women are the way out. 

[04:46] Whether it's with your clients, your team, your family, your community; active listening can open doors you never thought possible. 

[05:51] Once I started doing this with my teenagers, my whole life changed. It was an eye opener. 

Resources and Links mentioned in this episode

• Free Range Thinking
• World Listening Project
• White Paper on Active Listening
• Join Female Founders Society
• Let’s connect on LinkedIn

You might also like

•  Is Hiring a Mentor a Game Changer or a Money Waster?
• The AI Blueprint Strategy for Female Entrepreneurs
• Expand Your Reach: 8 Strategies for Niche-Bound Businesses

More about the “My Good Woman” podcast

My Good Woman is a podcast for new and future female leaders, hosted by me, Dawn Andrews.

Grab a seat at the table with me each week for candid conversations with culture-shifting, glass ceiling-busting, trailblazing women, who are leading enterprises that are making a change in the world. 

We discuss what makes them tick and how they get it all done. And we share actionable strategies to help you and your team get organized - so you can focus on your company’s growth, profit, and impact. 

If you liked what you heard, don’t forget to follow along, so you never miss an episode. And before you go, leave us a review - it would mean a lot to us!

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Can technology really boost your business growth? 

Today, we are diving into the transformative role of technology in business growth, exploring game-changing tools and innovations that can help you scale your business efficiently. 

Whether you're feeling overwhelmed by the tech landscape, or eager to try new tools, this episode is packed with actionable tips, and is your guide to harnessing technology for ultimate business efficiency and growth.

In this episode, I discuss:

• How to maximize your efficiency with automation tools.
• How automation can save you time and streamline your operations.
• How artificial intelligence can help improve your client interactions and boost satisfaction
• Leveraging data analytics to make strategic decisions in your business growth. 

This episode at a glance:

[02:39] Running a business means wearing a million hats, and there never seem to be enough hours in the day.

[04:32] Automation isn't just about saving time. It's about amplifying the impact of every minute you spend on your business.

[06:36] 40 percent of businesses say that customer or client experience is their top motivator for adopting AI.

[10:30] If it's just anecdotal information or your best guess, that opinion can be leading you down a road that is wasting your time, energy, and money.

Resources and Links mentioned in this episode

• Free Range Thinking
• Let’s connect on LinkedIn
• Follow me on Instagram
• Boost AI Strategy Framework
• Book a Consultation CALL with us!

You might also like

• The AI Blueprint Strategy for Female Entrepreneurs
• Expand Your Reach: 8 Strategies for Niche-Bound Businesses
• 4 Must Read Leadership Books

More about the “My Good Woman” podcast

My Good Woman is a podcast for new and future female leaders, hosted by me, Dawn Andrews.

I’m a happily married hockey mom, proud female leader, and founder and CEO of Free Range Thinking, where we turn founders into confident CEOs with strategic consulting and leadership training.

Grab a seat at the table with me each week for candid conversations with culture-shifting, glass ceiling-busting, trailblazing women, who are leading enterprises that are making a change in the world. 

We discuss what makes them tick and how they get it all done. And we share actionable strategies to help you and your team get organized - so you can focus on your company’s growth, profit, and impact. 

If you liked what you heard, don’t forget to follow along, so you never miss an episode. And before you go, leave us a review - it would mean a lot to us!

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Is hiring a paid mentor the secret to unlocking your business’s full potential with one key move—sounds dreamy, right?

From real-world success stories and hard-earned wisdom from those who’ve been there, and done that (like me) we're exploring the make-or-break decision of hiring a paid mentor.

But wait, there's a catch: we'll also dish on the financial risks and rewards, so you can make a smart, informed choice. Plus, we’ll cover how to balance external advice with your own badass instincts, and introduce you to our game-changing DISC-based mentorship approach that’s as unique as you are. 

Ready to turn your business dreams into reality? 

In this episode, I discuss:

• The pros and cons of hiring a paid mentor as a business owner.
•  How to make an informed decision to maximize your return on investment. 
•  How to balance expert guidance with your own instincts.
• The DISC-based mentorship approach, which tailors guidance to your unique personality type and business challenges, ensuring personalized support and growth.

This episode at a glance:

[01:50] A paid mentor is somebody who has walked the path that you want to walk. Somebody who does have subject matter expertise in that area. 

[06:10] My business needed to be in the right place, and I needed to be in the right place to receive the coaching offered.

[09:12] It's difficult to develop your clear vision and point of view when you are beholden to other people financially

[12:05] The goal is to create a harmonious blend of seeking mentorship and trusting your own judgment to be able to achieve success.

[13:44] The decision to hire a mentor is not a one-size-fits-all solution. It is a nuanced choice that depends on your unique business needs and your personal growth goals.

Resources and Links mentioned in this episode

• Free Range Thinking
• Dawn Andrews
• Book a Consultation CALL with us!
• Join Female Founders Society

You might also like

• Expand Your Reach: 8 Strategies for Niche-Bound Businesses
• Real-Time Coaching for Female Founders
• People Reading Guide

More about the “My Good Woman” podcast

My Good Woman is a podcast for new and future female leaders, hosted by me, Dawn Andrews.

Grab a seat at the table with me each week for candid conversations with culture-shifting, glass ceiling-busting, trailblazing women, who are leading enterprises that are making a change in the world. 

We discuss what makes them tick and how they get it all done. And we share actionable strategies to help you and your team get organized - so you can focus on your company’s growth, profit, and impact. 

If you liked what you heard, don’t forget to follow along, so you never miss an episode. And before you go, leave us a review - it would mean a lot to us!

Send us Fan Mail

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.