Best Alyson Caffrey Podcasts (2025)

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Entrepreneur Playbook for a Stress-Free Summer: Multipreneur Alyson Caffrey on Streamlining Operations 50:35

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23d ago50:35

50:35

Alyson Caffrey is an Operations Strategist, Bestselling Author of The Sabbatical Method, and founder of two businesses, Master Maternity Leave, and the consultancy Operations Agency. She’s best known for streamlining back-end operations of brands using her Operations Simplified™ framework to unleash the power of small teams. Alyson believes that if…

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Flexibility Is the Plan – Maternity Leave Roadmap #29 9:03

1d ago9:03

9:03

When you're building a plan for maternity leave, it’s easy to assume that once it’s in place, it’s set in stone. But the truth is, your needs, your baby’s rhythms, and your business might ask for something different. That’s not a sign you did it wrong. It’s a sign you’re paying attention. In this episode of the Maternity Leave Roadmap series, I’m t…

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Turn Objections into Opportunities: Entrepreneur Sales Guru Andee Hart on Selling with Integrity and Confidence 48:16

22h ago48:16

48:16

Andee Hart is an entrepreneur, sales strategist, mentor, and host of the podcast, She Sells Differently. While working as a sales executive for a Fortune 500 company, Andee started a passion project, Hart Design Co., of candle making in her own kitchen. What started out as a side hustle with her candles in a handful of local boutiques quickly bloss…

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Protect Your Energy While Prepping for Leave – Maternity Leave Roadmap #28 9:37

3d ago9:37

9:37

What if growth didn’t have to be loud, measurable, or tied to a to-do list? In this reflective episode of the Maternity Leave Roadmap series, I’m sharing what early postpartum really felt like and how disorienting it was to go from clear, daily business progress to the invisible work of motherhood. If you’ve ever felt like you’re falling behind jus…

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Choose Your Anchor Activity – Maternity Leave Roadmap #27 8:37

6d ago8:37

8:37

When your whole life is shifting, you need something that keeps you grounded. That’s what an anchor activity is for. In this episode of the Maternity Leave Roadmap series, I’m introducing one of the very first things we build inside The Bond coaching program: the anchor activity. Whether it’s journaling, stretching, walking, or simply breathing, th…

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Working on Maternity Leave – Maternity Leave Roadmap #26 7:51

8d ago7:51

7:51

Some people want to fully unplug during maternity leave. Others feel pulled to work, and that doesn’t have to be a bad thing. In this episode of the Maternity Leave Roadmap series, we’re talking about how to think through working during your leave. Whether it’s out of desire or necessity, this episode walks you through how to assess your time, your…

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Communicate with Courage: Entrepreneur Michelle Gladieux on Building Team Trust and Tackling Subconscious Obstacles 54:52

9d ago54:52

54:52

Michelle Gladieux is known as a human potential whisperer. She's written the award- winning book Communicate with Courage and she's President of Gladieux Consulting, a team of 7 teaching communication and leadership topics, offering executive coaching and strategic planning around the U.S. Michelle has 18 years collegiate teaching experience at thr…

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Train People How to Treat You – Maternity Leave Roadmap #25 8:29

10d ago8:29

8:29

Boundaries aren't just about protecting your time. They are about teaching others what to expect from you. In this episode of the Maternity Leave Roadmap series, I’m sharing what it really looks like to create boundaries that stick. I walk through how to set expectations with yourself, your team, and your clients, especially during maternity leave.…

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5 Boundaries to Set Before Baby Comes – Maternity Leave Roadmap #24 16:30

13d ago16:30

16:30

The closer you get to maternity leave, the more valuable your time and energy become. And the only way to protect both is with boundaries. In this episode of the Maternity Leave Roadmap series, I’m walking you through five boundaries that have helped me save my sanity during pregnancy, maternity leave, and early motherhood. These aren’t just “nice …

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The Power of Community and Intuition – Maternity Leave Roadmap #23 11:03

15d ago11:03

11:03

It’s easy to feel like you should have a village around you during motherhood and business. But what happens when that village doesn’t show up? In this episode of the Maternity Leave Roadmap series, I’m talking about the two forms of support that matter most in this season: community and intuition. I share personal stories of navigating early mothe…

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AI for Empathy and Inclusion: Entrepreneur Serena Huang on Data-Driven Initiatives for Building Diverse Teams and Measuring What Matters 48:16

16d ago48:16

48:16

Dr. Serena Huang is revolutionizing how organizations approach talent, well-being, and DEI through data and AI. The CEO and Founder of Data with Serena, she is also the author of the bestselling book The Inclusion Equation: Leveraging Data & AI For Organizational Diversity and Well-being. Serena is a sought-after international speaker and as an AI …

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The Identity Shift of Motherhood and Business – Maternity Leave Roadmap #22 10:43

17d ago10:43

10:43

The biggest shift in your maternity leave plan isn’t logistical. It’s personal. In this episode of the Maternity Leave Roadmap series, I’m sharing what that identity shift looked like for me, how it caught me off guard, and why it ultimately made me a stronger, more focused business owner. Whether you’re about to become a mom for the first time or …

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The Frontload Fallacy – Maternity Leave Roadmap #21 9:30

20d ago9:30

9:30

You’ve probably heard it before: just get everything done before baby comes. But what if trying to frontload your entire business is actually setting you up to fail? In this episode of the Maternity Leave Roadmap series, I’m breaking down what I call the “frontload fallacy” and why I believe one of the most important parts of preparing for maternit…

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Block a Day to Implement – Maternity Leave Roadmap #20 9:38

22d ago9:38

9:38

You’ve done the planning. Now it’s time to actually start building. In this episode of the Maternity Leave Roadmap series, we’re entering the implementation phase. I’m sharing one of the most effective tools I’ve used (and that we use inside The Bond) to help you get momentum when it’s time to put your plan into action: blocking a full day. You’ll …

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The Only 3 Problems in Your Business – Maternity Leave Roadmap #19 8:52

24d ago8:52

8:52

By now, you’ve probably uncovered a few areas in your business that need support. But what if diagnosing the real problem was simpler than you think? In this episode of the Maternity Leave Roadmap series, I’m sharing what I’ve learned from a decade of operations consulting: almost every issue in your business falls into just three categories. I’ll …

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Audit Your Finances Before Leave – Maternity Leave Roadmap #18 10:19

27d ago10:19

10:19

You don’t need to sell more to afford your leave. You need to start with the money you already have. In this episode of the Maternity Leave Roadmap series, I’m walking you through a step-by-step financial audit that helped me return from maternity leave with a more profitable and sustainable business. You’ll learn how to review your expenses, ident…

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Should I Get Insurance? – Maternity Leave Roadmap #17 7:55

29d ago7:55

7:55

Most business owners wait until something goes wrong before they think about insurance. But when you’re planning maternity leave, thinking ahead is a gift to your future self. In this episode of the Maternity Leave Roadmap series, I’m breaking down my own business insurance setup and explaining how I use a mix of state programs, private policies, a…

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Unleashing You: Entrepreneur and Executive Coach Amanda Riffee on Authentic Success Without Burnout or Sacrifice 39:40

30d ago39:40

39:40

Amanda Riffee is an internationally certified executive coach helping women overcome mindset blocks, know their value and create a career (and life) they love without burnout. A thought leader and event speaker with 17 years of corporate experience, she also hosts the podcast Unleashing You with Amanda Riffee and last month released her first book,…

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What Does My State Offer? – Maternity Leave Roadmap #16 5:57

1M ago5:57

5:57

One of the biggest questions I get from self-employed moms planning their maternity leave is: Does my state offer anything to help? In this episode of the Maternity Leave Roadmap series, we’re breaking down the truth about state programs, federal protections, and private options for financial support during your leave. I’ll walk you through how the…

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Schedule a Beat for Yourself – Maternity Leave Roadmap #15 8:38

1M ago8:38

8:38

There’s so much talk about prepping your business for leave, but what about you? In this episode of the Maternity Leave Roadmap series, I’m inviting you to schedule something we rarely give ourselves: space to feel. Whether it’s journaling, therapy, or just taking a quiet walk alone, this episode is your reminder that postpartum recovery isn’t just…

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Create Your One-Page Leave Plan – Maternity Leave Roadmap #14 7:41

1M ago7:41

7:41

There’s a moment in your leave planning process where things shift from ideas to action. This is that moment. In this episode of the Maternity Leave Roadmap series, I’m walking you through the exact structure of your one-page maternity leave plan. You’ll learn what to include, how to keep it simple, and why this document becomes the anchor for both…

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Newsroom to Boardroom: Emmy Award Winning Journalist Michelle Rupp on Helping Businesses Drive Valuable Earned Media 43:42

1M ago43:42

43:42

Michelle Rupp, an Emmy Award winning broadcast journalist, is the Founder and CEO of Memorable Results Media, a boutique agency dedicated to helping small and medium-sized businesses gain earned media coverage on local and regional television. With a background in news production and a passion for empowering business owners, Michelle uses her 25 ye…

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How to Tell Your Clients You're Pregnant – Maternity Leave Roadmap #13 8:33

1M ago8:33

8:33

If just the thought of telling your clients you're pregnant makes your stomach drop, you're not imagining it. This is one of the trickiest parts of maternity leave planning. In this episode of the Maternity Leave Roadmap series, I’m walking you through the exact three-part framework I use (and teach inside the Bond program) to help business owners …

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Give Your Team the Baton – Maternity Leave Roadmap #12 7:59

1M ago7:59

7:59

Delegation isn’t just about handing off a task. It’s about trusting someone to run with it, even if they do it differently than you would. In this episode of the Maternity Leave Roadmap series, we’re shifting from theory to practice. I’m walking you through how to set up the actual conversations and systems that make delegation stick, including how…

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Find Your Leading Indicators – Maternity Leave Roadmap #11 8:57

1M ago8:57

8:57

When something in your business feels “off,” the answer is usually upstream. In this episode of the Maternity Leave Roadmap series, we’re talking about leading indicators aka the activities that directly impact your results. Whether you’re trying to grow revenue, stabilize your systems, or step back without everything falling apart, knowing what to…

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Experiential Marketing: Entrepreneur Lacey Bridges on Elevating Brand Stories Through Human Connection 45:13

1M ago45:13

45:13

Lacey Bridges is the founder of Black Flamingo Agency, an experiential marketing firm in Los Angeles. As a visionary leader and innovative creative marketer, Lacey excels at crafting immersive experiences that drive brand success. Her entrepreneurial spirit and passion for the experiential side of marketing solutions have positioned Black Flamingo …

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Track Your Business Like a Coach – Maternity Leave Roadmap #10 7:14

2M ago7:14

7:14

You can’t manage what you don’t measure, and when you’re preparing to step away from your business, your data becomes one of your most powerful tools. In this episode of the Maternity Leave Roadmap series, I’m sharing how to get your data picture in place so you can make smart, confident decisions before, during, and after your leave. I’ll walk you…

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Design Your Perfect Week – Maternity Leave Roadmap #9 8:21

2M ago8:21

8:21

If you’re ending your weeks exhausted and wondering, Why did that feel so hard?—this is your sign to pause and reassess. In this episode of the Maternity Leave Roadmap series, I’m walking you through one of the most helpful tools I’ve used in business and motherhood: the perfect week. You’ll learn how to audit your calendar, align your time with wh…

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Block and Tackle Like a CEO – Maternity Leave Roadmap #8 7:22

2M ago7:22

7:22

You soon won’t have the bandwidth you used to. That’s not a weakness—it’s a turning point. In this episode of the Maternity Leave Roadmap series, we’re talking about how to protect your time by learning to block and tackle. I’ll walk you through how to decide what stays on your plate, how to communicate what you’re letting go of, and why this shift…

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Escape to Panama: Real Estate Maven Melissa Darnay on Why It Makes A Perfect New Home for Entrepreneurs 39:13

2M ago39:13

39:13

Melissa Darnay has been living her dream life in Panama since 2012 as the CEO of Choose Panama, a luxury real estate and rental agency based in Panama City. Melissa specializes in helping clients find the perfect investment properties that align with their personal dreams and financial goals. Her unique approach sets her apart from other real estat…

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The 4 Core Systems Every Business Needs – Maternity Leave Roadmap #7 7:27

2M ago7:27

7:27

Most founders are stuck in the weeds not because they’re doing something wrong—but because their business is missing a system. In this episode of the Maternity Leave Roadmap series, I’m sharing the four core systems every business needs to operate without you. Whether you’re solo or have a small team, these categories will give you a framework to a…

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Build Your Central Source of Truth – Maternity Leave Roadmap #6 6:04

2M ago6:04

6:04

Most team breakdowns don’t happen because of bad intentions—they happen because no one knows where to find what they need. In this episode of the Maternity Leave Roadmap series, I’m walking you through one of the most powerful tools you can put in place before your leave: a central source of truth. This simple system brings clarity, consistency, an…

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How to Delegate with Clarity – Maternity Leave Roadmap #5 7:33

2M ago7:33

7:33

Want to delegate with confidence before baby comes? It starts with one simple habit. In this episode #5 of the Maternity Leave Roadmap series, we’re building on your outsource list from last time and getting tactical. I’m walking you through the exact method I use to train team members, set clear expectations, and standardize tasks—without adding e…

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Focus On Feedback: Serial Entrepreneur Penny Zenker AKA “The Focusologist” on Achieving More With Less 49:21

2M ago49:21

49:21

Penny Zenker is a serial founder, sought-after speaker, bestselling author, and former C-Suite executive of a global top five market research company who now helps entrepreneurs and executives at firms large and small, including Deloitte, Pfizer, SAP and Samsung solve complex problems and find alignment to accelerate business growth. Over the past …

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What Can You Afford to Outsource? – Maternity Leave Roadmap #4 7:41

2M ago7:41

7:41

When it comes to maternity leave planning, one of the biggest mindset blocks I see is this: “I don’t know if I can afford to get help.” In episode #4 of the Maternity Leave Roadmap series, we’re talking about time, money, and the numbers behind your capacity. I’ll walk you through a simple, eye-opening exercise to help you calculate your hourly rat…

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Practice Taking Time Off – Maternity Leave Roadmap #3 7:24

2M ago7:24

7:24

We don’t build confidence by hoping things will go well—we build it through practice. In this episode #3 of the Maternity Leave Roadmap series, we’re shifting from intention-setting and time-blocking into real-life action. One of the most powerful ways to prepare for maternity leave is to start practicing what it feels like to step away—before you …

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How to Make Time to Plan Your Leave – Maternity Leave Roadmap #2 7:45

2M ago7:45

7:45

Making time to plan your maternity leave doesn’t require a big life overhaul. You just need one focused habit. Welcome back to the Maternity Leave Roadmap series. If you’ve been wondering how you’re going to squeeze in planning between client work, toddler chaos, and everything else life throws at you—this episode is exactly what you need. Today, I…

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Inside the Crucible: Entrepreneur Lindsay Guzowski on Transforming Venture and Private Equity with Unbiased Executive Assessments 57:04

2M ago57:04

57:04

Lindsay Guzowski is the CEO and founder of The Crucible, a company transforming how private equity and venture firms assess and develop leadership at their portfolio companies using scientifically validated, bias-tested tools. A visionary entrepreneur, she co-founded a plumbing company that grew from a $40,000 investment into a multi-million-dollar…

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Welcome to The Maternity Leave Roadmap Series 7:41

2M ago7:41

7:41

Welcome to the start of the Maternity Leave Roadmap series. This is the beginning of something big. If you're a self-employed mom who’s thinking about growing your family—or you're already pregnant or postpartum—you’re in the right place. Over the next 30 episodes, I’m walking you through how to plan a self-employed maternity leave that supports bo…

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Charles Gaudet • Predictable Profits 37:33

2M ago37:33

37:33

Charles Gaudet, CEO and cofounder of Predictable Profits brings unrivaled experience as a leader and coach to successful businesses scaling beyond seven figures. When founders want to become bigger and better, they choose his program. Charles and the team at Predictable Profits have rewritten the playbook to success, and this episode gives you a gl…

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When Grace Becomes an Excuse + Big Changes Coming to the Podcast 15:31

2M ago15:31

15:31

“Give yourself grace.” It’s a phrase we hear all the time—especially in motherhood and entrepreneurship. But what happens when that grace quietly turns into an excuse? In this special 100th episode of Growing Pains, I’m reflecting on the evolution of the show, my own journey as a business owner and mom, and the hard lesson I’ve learned about using …

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Tackling the 2% Problem for 10X Returns: Venture Investor Julie Castro Abrams on Building Her Woman-Only VC Fund 59:00

2M ago59:00

59:00

Julie Castro Abrams is a venture capitalist and gender and racial justice activist who has spent the majority of her career working to build great women-owned companies and economic access for women. She is the founder and CEO of How Women Lead, a network of 14,000-plus top executive women who come together to learn, break barriers to success, and …

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Writing Your Next Chapter: Entrepreneur Nina Sossamon-Pogue on Resilience and Overcoming Adversity 43:45

3M ago43:45

43:45

Nina Sossamon-Pogue is a sought-after speaker, two-time bestselling author, and entrepreneur whose journey through elite gymnastics, TV anchoring, and Corporate America from startup to IPO defies the ordinary. An Olympic hopeful on the USA Gymnastics team with Mary Lou Retton, an injury crushed her dreams before becoming a catalyst for a 20-year ca…

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Transforming Gardening with AI: Entrepreneur Donna Letier on Cultivating Wellness with Container Gardens 47:40

3M ago47:40

47:40

Donna Letier is the CEO and founder of Gardenuity, a fast-growing company merging gardening with the wellness sector through personalized container gardens and AI-powered gardening experiences. Donna has raised $8 million for her company so far, innovating Gardenuity Match, which uses AI and weather tech to custom-craft gardens around lifestyles, c…

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Tax Time: Entrepreneur Melissa Broughton on How to Be Proactive with Tax and Accounting 43:39

3M ago43:39

43:39

Melissa Broughton is a tax and accounting specialist and the founder of Busy Bee Advisors, helping business owners and entrepreneurs get savvy about complex, even frustrating, tax and bookkeeping situations. Her background in corporate accounting and auditing complements her desire to serve as a financial translator, of sorts, to sole proprietors a…

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Tactical Harmony, Unleashed: Entrepreneur Rebecca Fitzsimmons On Mastering Leadership, Mindset and What We Can Learn from Dogs. 33:40

3M ago33:40

33:40

Rebecca Fitzsimmons is the founder of Tactical Harmony, an online business dedicated to mentoring ambitious professionals and businesses on holistic leadership and mindset strategies. She is also the host of the Tactical Harmony podcast, in which she shares game-changing tactics supporting her community to gracefully navigate their career and homel…

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The Authenticity of You: Entrepreneur Lauren Bayne on Building a Differentiated Personal Brand to Grow Your Company 45:56

4M ago45:56

45:56

Lauren Bayne is a personal brand creative director, advising entrepreneurs and executive leaders in building personal brands filled with personality and creating intellectual property that makes her clients money. Coming from the advertising industry, Lauren brings creative expression and pizazz to personal branding that gives her clients confidenc…

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Data Dashboard Diva: Entrepreneur Kari Poppleton on Actionable Insights for Business Growth 40:21

4M ago40:21

40:21

Kari Poppleton is the CEO and founder of Kari Poppleton Consulting, specializing in digital marketing metrics, data, and custom interactive dashboards. A Certified Director of Operations and Certified Dashboard Designer, Kari helps online entrepreneurs, course creators, coaches, and anyone with memberships and subscriptions, leverage actionable dat…

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Own Your Own Journey: Entrepreneur Somia Sadiq on the Power of Failure and Overcoming Risk Adversity 38:32

4M ago38:32

38:32

Somia Sadiq is an award-winning entrepreneur and peacebuilder who has developed a pioneering practice in impact assessment and conflict transformation rooted in storytelling. Somia is the founder and CEO of Narratives, a planning firm that emphasizes human-centric, trauma-informed dialogue, lived experience, and celebrating ancestral identity. She’…

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Agentic AI: Serial Entrepreneur Susan Sly on Ethics, AI Transparency, Future of Work and How thePause.ai is Transforming Menopause Care 58:49

4M ago58:49

58:49

Susan Sly is an award-winning AI entrepreneur, author, keynote speaker, and the Founder and CEO of thePause.ai, an AI-driven platform revolutionizing menopause management with personalized, gamified solutions. In November, thePause.ai won first place in the HITLAB x Versalie™ Innovation Challenge. Susan also co-founded RadiusAI, a visual intelligen…