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The End Game Entrepreneur

Author: Kassie O'Driscoll

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Welcome to The End Game Entrepreneur podcast, where we dive deep into the stories and experiences of entrepreneurs who are building businesses that align with their passions and long-term goals. Hosted by Kassie, each episode features candid conversations with business owners who share their "end game," the defining moments that led them to entrepreneurship, and the bold goals that keep them motivated.

Through relaxed, insightful discussions, we uncover the challenges, wins, and real-life experiences that shape their path to success. Whether you're a seasoned entrepreneur or just starting out, this podcast offers inspiration, advice, and relatable stories that remind us all: the end game is about more than just the hustle—it's about defining your purpose, creating a meaningful impact, and living the life you've always imagined.

Tune in for a mix of business tips, personal reflections, and thought-provoking talks that will help you navigate your own entrepreneurial journey. Let’s focus on the bigger picture and take actionable steps to achieve the goals that truly matter.
45 Episodes
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#44 My End Game

#44 My End Game

2025-03-1222:20

In this episode of The Endgame Entrepreneur, Kassie shares her personal endgame vision: building a life on 30 acres in North Carolina with space for family, events, and a deep connection to nature. She discusses how she and her husband, a military family nearing retirement, have intentionally planned for this dream, using tools like MindMeister to align daily actions with long-term goals. Kassie also talks with her eight-year-old daughter, Coco, about her own aspirations, ranging from becoming an architect to owning a Chick-fil-A or moving to a big city. The episode highlights the importance of setting clear goals, making intentional choices, and taking small but meaningful steps toward a dream life. Kassie encourages listeners to reflect on their own endgame, stay focused on their vision, and take consistent action to make it a reality.Visit My WebsiteJoin My NewsletterCreate your own MindMeister Mind Map
The Endgame Entrepreneur podcast, hosted by Kassie, explores the journeys of business owners and the strategies they use to achieve meaningful success. In this episode, Kassie interviews Kelsey Flannery, owner of KaeRae Marketing, who specializes in Google Ads and SEO. Kelsey explains the power of Google over social media for business growth, highlighting the importance of audience behavior, keyword strategy, and leveraging Google tools like Google Business Profile and Google Analytics. She also shares insights on AI in content creation, advising business owners to use it as a tool rather than a replacement for original content. Kelsey encourages listeners to explore her services, free resources, and YouTube channel for further education, while Kassie wraps up by inviting listeners to connect through her newsletter and continue working toward their entrepreneurial goals.LinksKaeRae MarketingKaeRae EducationJoin My NewsletterKassie Layne – Online Business Management Services
The Endgame Entrepreneur podcast, hosted by Kassie, has been rebranded from the Mastermind Mixer to focus more on long-term entrepreneurial goals, including retirement and legacy building. In this episode, Kassie speaks with Bridget and Lydia, co-founders of Visibility on Purpose, a PR and media training company helping small businesses gain exposure without massive budgets.They discuss common PR misconceptions, emphasizing that media coverage isn’t just about pitching products but aligning with a publication’s goals and audience interests. They highlight the importance of knowing one’s own business objectives before pursuing media placements, as PR is a long-term brand growth strategy rather than a quick advertising fix. The conversation concludes with insights on alternative visibility strategies, such as podcast tours, and the necessity of goal clarity in both PR and business operations.Check out this link for all of the links and show notes
#41 ESC 2025 is LIVE!!

#41 ESC 2025 is LIVE!!

2024-10-2843:10

In this special Monday episode, Kassie and Ali discuss the ESC Conference 2025, detailing its mix of education, networking, and unique experiences tailored for entrepreneurs in the “messy middle.” Attendees will benefit from masterclasses, roundtables, and an open Q&A session, all offering practical guidance on topics like marketing, systems, and finance.Alongside learning, social events include live music, themed gatherings, and a Louisville-themed field trip, fostering community and creativity.The event venue, The Bungalow in Louisville, supports the collaborative spirit with its quirky charm and communal atmosphere.Tickets cover all activities, meals, and accommodations, with a VIP option adding exclusive coaching opportunities.Join us Mondays from 1-2PM EST for Productivity Power HourFind us on IGJoin our FREE NewsletterESC Impact Weekly - SubscriptionESC Conference 2025
**Update: Ali and I decided not to host the webinar because...life. Much like the rest of our community, we are in the messy middle, figuring it all out. While we do still plan on hosting one in the future, we will not be hosting any during this launch. Thank you for understanding!**Teaming up under ESC Events, Kassie and Ali are excited to discuss the new offer they developed after their recent ESC Conference, which exceeded their expectations by fostering numerous business connections. In addition to the ESC Retreat, they want to continue supporting their community throughout the year.Inspired by Ashlyn Carter's newsletter approach, they are launching the ESC Impact Weekly Subscription. This newsletter will provide practical, themed content on operations, community, marketing, and lifestyle, designed to support solopreneurs and small business owners.The subscription will be available starting from August 7th to August 13th, offering a free month for early subscribers. After the open cart period, the ESC Impact Weekly Subscription will be available for $12 per month, with a 30-day free trial to showcase its practical, actionable content.They are also hosting two webinars on August 7th and August 12th, titled "8 Steps to ESC the Grind: Actionable Strategies for Female Entrepreneurs" offering a preview of the subscription's benefits. Kassie and Ali emphasize that the subscription will provide immediate, useful strategies without any fluff!Sign up now! | ESC Impact Weekly Newsletter SubscriptionAugust 12th WebinarAugust 7th Webinar
Marisa Lonic is on today's episode! She's the founder of Mama Work It, an organization supporting working moms in balancing their various roles. Marisa shares her personal journey of feeling overwhelmed while managing a demanding corporate job and family life, leading her to create resources for working mothers. She emphasizes the importance of time management, practical hacks, and the internal work required to manage guilt and maintain a sense of balance. Marisa discusses her transition from corporate work to full-time entrepreneurship and highlights the varying needs of her coaching clients, ranging from corporate professionals to aspiring entrepreneurs.The conversation highlights the importance of writing down tasks to clear mental clutter and the value of having accountability partners. Marisa also explains the different ways clients can work with her, emphasizing the importance of finding the right coach-client fit and incorporating both practical strategies and mindset work into her coaching.Throughout the episode, Marisa advocates for the integration of mindset work and practical strategies, including manifestation and intuition, to achieve both personal and professional goals.Morning Manifesting MeditationMarisa on LinkedInLet Mama Work It on FBFind Marisa on IGMarisa Lonic WebsiteSlay the Day I Mama Work It
This episode features a conversation with Allison Hardy, an email marketing strategist. Allison specializes in helping coaches and experts automate their marketing processes, allowing them to focus more on client work rather than constant promotion. She emphasizes the importance of choosing a reliable email platform with good deliverability and automation features, recommending ConvertKit, which she has used for years. Allison also shares her journey into email marketing, which began after being laid off while pregnant and pivoting from personal training to business mentoring. She highlights the importance of not overwhelming clients with information during onboarding, suggesting a gradual approach over two weeks.Allison discusses her approach to webinars, noting that she hosted them bi-weekly to keep her skills sharp and maintain consistent lead generation. She also underscores the value of transparency, using personal success stories and client testimonials to build trust. Allison advises listeners to be their own best clients by implementing the strategies they recommend to others, thereby demonstrating credibility and effectiveness.The episode concludes with Allison promoting her $80,000 email template and encouraging listeners to connect with her on Instagram.Find Allison on IG!The $80,000 Email TemplateAllison's Website
Angelica Pompy of Pompy Portraits and Angelica Pompy Education shares her journey as a boudoir and maternity photographer in Jacksonville, Florida, and her transition to a business coach and marketing strategist for female entrepreneurs. She emphasizes the importance of creating a memorable client experience and how her peers encouraged her to start coaching. Angelica recently launched "Business Church," a social media and business marketing membership aimed at helping women master their marketing strategies, offering themed quarterly content, live workshops, and a supportive community.She discusses how she manages her time by dedicating specific days to her education business and photography, ensuring she maintains boundaries to protect her peace. She shares her experience of building a team during the pandemic to support her growing business, emphasizing the importance of having a visionary assistant.Angelica elaborates on her systematic approach to planning the year and implementing new systems and highlights her strong partnership with her husband, balancing work and personal life.She provides details about the upcoming topics in her Business Church membership for 2025 and invites listeners to join for a free month.Find Angelica on IG!Photography Business Coach + Education | Angelica PompyFREE MONTH of Business Church
2nd time guest, Lucy Kelly, a marketing strategist for creative entrepreneurs, shares her journey from being a speech pathologist to discovering her passion for jewelry-making during a summer of self-improvement. Her business evolved from making and selling upcycled vintage jewelry to becoming a marketing strategist and coach, where she now manages both product sales and coaching, constantly reorganizing and automating processes to handle her growing responsibilities. Despite having efficient workflows for her product business, Lucy faces challenges in managing software tools and launching webinars, and is considering hiring an Online Business Manager (OBM) to ensure everything runs smoothly.In the latest part of the discussion, Lucy elaborates on her difficulties with various software tools and systems. She mentions her struggle with webinar platforms like Demio and Zoom, where she faces issues with bandwidth and integrations.Kassie, who is an OBM herself, suggests that Lucy might benefit from having someone oversee these systems, as switching between different tools like Kajabi, ConvertKit, and Thrivecart creates complications. She explains how having an OBM can help Lucy streamline her processes and ensure her systems work efficiently without her constant oversight.As the conversation progresses, Lucy acknowledges the need for an OBM to help manage her growing responsibilities, especially with her personal commitments and the inefficiency of spending time on technical issues.They discuss the benefits of having an OBM to oversee these processes, allowing Lucy to focus on her core strengths and business growth. Lucy concludes by outlining her upcoming offers, including the Marketing School for Makers and coaching services for scaling successful handmade businesses, leveraging her expertise in Facebook ads and customer behavior.Join Lucy's FB GroupFind Lucy on YouTube!Find Lucy on Pinterest!Find Lucy on FB!Find Lucy on IG!Start and Grow a Handmade Business | Bloom by bel monili
Kassie is joined by Lydia, who shares her story of transitioning from a military spouse and school teacher to a custom cookie business owner. Lydia explains that her husband served in the Marine Corps for almost 11 years, after which she became a teacher until she became pregnant with her sixth child and found teaching overwhelming. Lydia then decided to quit her teaching job and focus on her side hustle of making custom cookies, aiming to replace her teaching salary with her new business.Despite the challenges, including a premature baby, Lydia successfully replaced her teaching salary with her cookie business within six months. Over time, she expanded her business to include cookie classes, raising her prices and optimizing her processes to work less while earning more. Currently in her third year, Lydia has further scaled her business by adding a booth in a storefront, teaching cookie classes, and securing significant corporate clients like a local casino.Lydia shares how her initial marketing strategy of featuring local shops on her cookies quickly gained popularity, but she had to stop due to becoming too busy. She discusses the automation of her business's backend processes, including inquiries, contracts, and invoices, to handle the increasing workload efficiently. Lydia uses her website to streamline orders and employs automated responses to manage customer expectations and communication, ensuring she maintains a balance between her work and personal life. The conversation then shifts to the importance of setting boundaries and implementing automation to sustain business growth.Kassie truly enjoyed her conversation with Lydia and looks forward to the next one!Find Off the Lyd Cookies & Co. Online!WebsiteFacebookInstagramEmail: offthelyd@gmail.com
SummaryAshley Ebert, owner of the Abundance Group, shares her journey from owning a wedding planning company to teaching small business owners how to develop their leadership skills and build a streamlined team. She emphasizes the importance of documenting processes and providing intentional training to build trust with team members. Ashley also discusses the transition from managing to owning a business and the mindset shift required to feel deserving of the dividends of hard work. She shares her love for Disney and craft beer, and invites listeners to connect with the Abundance Group through their website and Instagram.TakeawaysDocumenting processes and providing intentional training are key to building trust with team members.Transitioning from managing to owning a business requires a mindset shift and recognizing that the dividends are earned through hard work and risk-taking.Leadership skills can be learned and developed, and they are essential for managing and leading a team effectively.Building a community of business owners who are developing their leadership skills can provide support, knowledge sharing, and networking opportunities.Taking time for personal interests and hobbies, such as Disney and craft beer, can bring joy and balance to the entrepreneurial journey.Take The Abundance Group's leadership quiz Find us on Instagram
Kassie, the host of the Mastermind Mixer podcast, introduces herself and her guest, Shalie, a business coach. Shalie shares her background, explaining how she started as an online business manager in 2021 before transitioning to business coaching. She focuses on helping online business owners, particularly coaches, course creators, and agency owners, to scale and grow through operations and delegation.Shalie also recounts her entrepreneurial upbringing and her brief stint in corporate life, highlighting her transition to freelancing and her ultimate shift to becoming a digital nomad and business coach.Kassie shares her experiences hosting a business conference and how it gave her clarity on her own business after feeling a lack of foundation, and a pivotal moment during a speed networking session where she received clarity on her role from a marketing firm owner.Kassie and Shalie discuss the challenges of finding appropriate clients and fair pay as a VA, and how they transitioned into OBM and Coaching, ultimately succeeding with high-level entrepreneurs. They emphasize the importance of diversifying marketing strategies and highlight the value of online networking events and mentorships.Paired Drink: Pina Colada
Kassie, the host of the Mastermind Mixer, introduces the show and welcomes Kelsey Flannery from KaeRae Marketing, who specializes in Google Ads and SEO. Kelsey explains her journey into mastering Google tools, becoming Google certified, and the importance of using both paid ads and organic SEO to grow businesses. She highlights the challenges businesses face in allocating budgets for Google Ads and the strategic approach needed to maximize ROI. Additionally, Kelsey offers audits, courses, and consultations to help businesses navigate Google’s marketing tools effectively, emphasizing her passion for educating others.She explains that her primary clients are home service businesses that benefit from Google searches. Kelsey also discusses the challenges businesses face with marketing budgets and the strategic use of Google tools. She highlights the role of human behavior in targeting audiences effectively and the impact of AI on content creation.Kelsey provides three essential tips for optimizing Google presence: setting up a Google Business profile, using Google Analytics, and focusing on SEO.The conversation also touches on Kelsey's personal interests, including her love for TV shows like "Severance" on Apple TV.KaeRae Marketing Website KaeRae Education Find Kelsey on Facebook Find Kelsey on InstagramFind Kelsey on YouTube
Kassie, the host of the Mastermind Mixer, introduces her guest, Kelly McCracken, who specializes in services for Wedding Professionals, including blogging, Pinterest, and Dubsado. Kelly explains how she transitioned from being a virtual assistant to focusing on Dubsado, choosing it for its comprehensive capabilities over other platforms like HoneyBook. Despite initial struggles learning the system, she became proficient and advocates for its long-term benefits.Kassie and Kelly discuss their shared experience with Dubsado and how it supports their business needs, emphasizing its evolving features and flexibility. Kelly also shares her background, including working for her parents' party rental business and transitioning to virtual assistance during the COVID-19 pandemic, ultimately seeking more flexibility and planning for a future with children.They continue their discussion, delving deeper into Kelly's journey and her work with wedding professionals. Kelly shares how her own wedding planning experience highlighted communication issues in the industry, which inspired her to offer administrative services to wedding vendors. She describes her first client, a wedding planner, who needed help with Dubsado, giving Kelly valuable hands-on experience. They also discuss Kelly's self-taught design skills, particularly in proposal creation, and her growing confidence. Additionally, Kelly outlines her structured approach to blogging and Pinterest services, emphasizing the importance of combining both for effective results and maintaining client reports to track performance.Kassie and Kelly continue their conversation, focusing on the challenges and strategies of providing effective client services. They discuss the importance of showing clients tangible results, particularly in saving time through automated systems like Dubsado. Kelly details her offboarding process, which includes personalized guidance and automated follow-up emails to ensure clients effectively use their new systems. They also touch on the difficulties of manual to automated transitions and the significance of maintaining client engagement and satisfaction. The conversation concludes with considerations on scaling services and potentially offering more comprehensive management support for clients as their businesses grow.Kelly's WebsiteFind Kelly on IGFreebie - Dubsado Step by Step Inquiry Workflow Guide + Canned Emails
Kassie, Claire, and Ali discuss their final thoughts surrounding the ESC conference, walking through the last full day of the conference and everything that came along with it... this time, from the comfort of their cozy hotel after everyone had left.They share insights on handling logistical challenges, communication developments, and tips on planning a conference on your own.The episode reflects on things that went well (and what didn't), the dynamics of event planning, and strategies for future improvements.
During the first live episode of The Mastermind Mixer, Chelsea from My KY Bucket List shares all her tips, tricks, advice and insight into Influencer and UGC Marketing. With almost 100k organic followers, Chelsea is building a business around her family and finding creative ways to introduce Influencer Marketing to places using unique strategies. Join us as we pick Chelsea's brain live from the ESC Conference.
Kassie, Claire, and Ali discuss the first full day of the ESC conference, focusing on activities like 'Blind date with a book,' speed networking, overcoming a catering app failure, and the sequence of events from start to finish -- all at 1 in the morning!They share insights on handling logistical challenges, including a hailstorm and Wi-Fi outages, and the importance of teamwork, attendee engagement, and feedback.The episode reflects on late-night preparations, the dynamics of event planning, and strategies for future improvements. The summary highlights the team's efforts to create a supportive community and adapt to unexpected situations during the conference.
In this episode of 'The Mastermind Mixer,' Kassie, Claire, and Ali take us behind the scenes of the first night of the inaugural ESC Conference 2024. They share the excitement, challenges, and unexpected moments of hosting their very first ESC conference. From the logistics of organizing such an event to the joy of welcoming attendees, they offer a candid look at what it takes to put together a conference aimed at fostering a strong community of entrepreneurs.The episode kicks off with Kassie's passionate introduction, highlighting her journey as an entrepreneur and the mission behind 'The Mastermind Mixer.' It then transitions into the excitement surrounding the conference kick-off, where co-founders Kassie and Ali, along with their Hospitality Manager Claire, welcomed attendees with open arms and high expectations for the days ahead.As the night progresses, they delve into a detailed recap of night one, including sitting on the floor of their suite for an impromptu recording session, laughter, and delirious comments after a long day. The unexpected becomes a theme as they take you along as their props and decor are saved from rain by Claire and the genuine behind-the-scenes moments that attendees don't usually get to see.Further into the episode, they discuss the unexpected challenges they faced, from the catering mix-ups to the logistics of ensuring everything was perfect for their guests. However, it's the silver linings and learning moments that shine through, as they talk about how these experiences brought them closer as a team and taught them valuable lessons for future events.One of the episode's highlights is the discussion about the thoughtful attendee gifts and the effort to build a strong community amongst entrepreneurs at the conference. Kassie and Ali share anecdotes of the connections forming between attendees, the impact of welcoming people into the 'ESC family,' and the overwhelming feedback on the details that made the event special.To wrap up, they reflect on the success of the first night, despite the hiccups, and express excitement for what's to come. The blend of humor, honesty, and insights into event planning makes this a must-listen for anyone interested in entrepreneurship, community building, and the reality of organizing a successful conference.Stay tuned for more episodes as they continue to share their journey through the ESC Conference 2024.If you enjoyed this episode, please consider rating and reviewing the podcast. Don't forget to subscribe for more insights, laughter, and entrepreneurial advice. Until next time, keep embracing the unique journeys and connections that come your way.
In this episode of The Mastermind Mixer, we take a brief look into the powerful integration of the Enneagram and client experience with a quick mention of how Jason Fiefer's personal mission statement strategy directly relates to your Ennegram number. By understanding the nuances of each Enneagram type, you can foster deeper connections with their clients, tailoring their approach to meet individual needs effectively. Crafting a personal mission statement further enhances this process, providing a guiding compass aligned with one's core values and aspirations. Together, these tools empower clients to navigate challenges, make intentional decisions, and pursue meaningful goals with clarity and purpose, ultimately transforming their journey toward personal and professional growth. A refreshing and vibrant cocktail like a Gin and Tonic would pair well with this podcast. The crispness of the gin and the effervescence of the tonic water would provide a light and uplifting accompaniment to the thoughtful exploration of the Enneagram and personal mission statements.
Kassie gives you a real life example of how a small act of kindness can change the way people view you, your business, and change your life for the better. While navigating her first 3 month scan after being diagnosed with Low Grade Serous Carcinoma, she encountered her very own Lucky Penny -- a phlebotomist who led with kindness and love.
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