The Corporate Escapee: On a Mission to Help 100,000 GenXers Escape the 9-5!

Brett Trainor
  • 4.8 (33)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY
The Corporate Escapee: On a Mission to Help 100,000 GenXers Escape the 9-5!

The Corporate Escapee Podcast is a resource for GenX professionals ready to break free from the constraints of corporate life and design a more intentional, fulfilling lifestyle. Hosted by Brett Trainor- who’s been on the escapee journey for nearly five years—and who’s been helping others make the leap for just over a year—this podcast goes beyond just replacing replacement to focus on a life built around four core pillars: Happiness, Wellness, Freedom, and Financial Stability. Every episode features real stories, practical advice, and actionable insights from successful escapees, subject matter experts, and thought leaders. We dive into the realities of building financial stability outside corporate, creating a sustainable work-life balance, and rediscovering personal joy and wellness along the way. Our Mission:
To empower 100,000 GenXers to escape corporate, reclaim their lives, and build an intentional life that reflects what truly matters. We believe that finding your first customer is easier than finding your next job—and that you don’t have to do it alone. Community, connection, and a fresh approach to work-life design are key. Key Themes: * Income Replacement Strategies: Practical paths to replacing corporate income with work that aligns with your lifestyle goals * Freedom and Autonomy: Stories of crafting a life on your own terms, from solo consulting to fractional leadership * Wellness and Happiness: Insights on prioritizing physical and mental well-being, and making time for the things that truly matter * Financial Stability: Building a reliable income stream without corporate constraints Whether you’re exploring the escapee path, in the process of making the leap, or simply want more freedom and fulfillment, The Corporate Escapee Podcast offers the insights and support you need. Join us, and let’s redefine success together

  1. 5 DAYS AGO

    Testing Assumptions & Finding Freedom: Lessons from Joe Manganelli's Escape

    In this episode of the Corporate Escapee Podcast, Joe Manganelli shares his journey from a corporate finance role to becoming an entrepreneur and the founder of Calculate, a financial services company.  He discusses the challenges and triumphs of building a business, the importance of embracing discomfort, and the lessons learned along the way. Joe emphasizes the value of testing assumptions, the significance of enthusiasm in business, and the need for accountability in entrepreneurship.  He also reflects on his recent transition to a new role as Chief Revenue Officer at Amalgam, a software company for accounting firms, and offers advice for aspiring entrepreneurs. Links LinkedIn: https://www.linkedin.com/in/joemanganelli/ Takeaways Embrace the discomfort of entrepreneurship.Don't wait for the perfect idea; start with what you have.Testing assumptions with clients is crucial for success.The early days of a business are often the most exciting.Perfection can hinder progress; focus on being good enough.Networking in small business is collaborative and supportive.Scaling a business requires understanding what is scalable.Accountability in entrepreneurship can be invigorating.Transitioning from corporate to entrepreneurship can be a mindset shift.Always be open to new opportunities and networks. Sound Bites "I realized I had it right in my hands.""Don't be afraid to test those assumptions.""The worst thing that happens is you fail." Chapters 00:00 Introduction and Current Endeavors 04:21 The Journey from Corporate to Entrepreneurship 11:55 Building Calculate: The Early Days 18:04 Scaling and Diversifying Services 22:10 Transitioning and Selling the Business 24:59 Current Role and Future Aspirations Keywords entrepreneurship, corporate escape, startup journey, accounting software, business growth, scaling, revenue streams, personal development, risk-taking, networking

    39 min

  2. NOV 11

    The Smart Way to Structure Your Escapee Business: LLCs, S-Corps, & Big Tax Savings with Gabrielle Tenaglia

    In this episode of the Corporate Escapee Podcast, Gabrielle shares her journey from a full-time marketing career to going solo, discussing the importance of understanding taxes and business structures like LLCs and S-Corps.  She emphasizes the advantages of S-Corps in reducing self-employment taxes and the necessity of managing payroll effectively.  The conversation also highlights the role of technology in simplifying financial management for escapees and the future of solo businesses in a rapidly changing workforce.  She provides practical advice on starting a business, including the necessity of separating personal and business finances, the significance of business insurance, and the considerations for forming an LLC or S-Corp.  Links: Lettuce Promotion: Lettuce landing page: https://hubs.ly/Q02SpnrJ0 Code is ESCAPEE500 Free Resources: https://lettuce.co/resources Gabrielle LinkedIn: https://www.linkedin.com/in/gabrielletenaglia/  Takeaways Freelancing offers flexibility and control over one's career.Understanding tax structures is crucial for freelancers.S-Corps can significantly reduce self-employment taxes.Time is a valuable resource that should not be wasted on bookkeeping.Automating financial management can alleviate stress for freelancers.Choosing the right business structure can lead to substantial tax savings.Freelancers need to pay themselves a reasonable salary to comply with IRS regulations.Technology can simplify the complexities of managing a freelance business.Networking is essential for finding opportunities and support.The future of work is shifting towards more freelancers and solo businesses. Finding experts that understand your business is crucial.Separate your personal and business finances from the start.Business insurance is essential for liability protection.An LLC is not always necessary unless concerned about liability.S-Corps can provide tax benefits for committed business owners.Fractional teams can offer specialized knowledge and skills.Sharing your ideas can attract clients to your business.Celebrate your achievements as a solopreneur.Understanding tax implications is vital for financial success.Lettuce provides tailored solutions for solo entrepreneurs. Sound Bites "My time is my most valuable resource.""You have to pay yourself a reasonable salary.""I didn't want to do any of it.""We are focused only on businesses like yours.""You need an LLC to have an S-Corp.""Get an S-Corp because every penny you make saves.""You are doing a great job.""Start with the idea before the product.""The government doesn't need any more from us." Chapters 00:00 The Journey to Freelancing 02:56 Understanding Taxes and Business Structures 06:05 The S-Corp Advantage 09:01 Navigating Payroll and Tax Responsibilities 11:49 The Role of Technology in Managing Finances 15:07 Finding the Right Tools for Freelancers 18:00 The Future of Freelancing and Business Management 25:10 Understanding Business Needs and Solutions 28:19 Best Practices for Starting a Business 31:36 Navigating LLCs and S-Corps 35:22 The Value of Fractional Teams 41:41...

    47 min

  3. OCT 31

    An Escapee’s Journey: From Corporate Exec to Solo Consultant, Firm Owner—and Surprisingly, Software Developer!

    Ray McKenzie, founder and managing director of Red Beach Advisors, shares his journey from corporate to entrepreneurship. He started his consulting firm in 2015, focusing on go-to-market strategy and operational efficiency for Fortune 1000 companies in cybersecurity and cloud computing. Later, he founded Starting Point, a workflow management and automation platform for professional services companies. Ray emphasizes the importance of building and maintaining relationships, leveraging your corporate network, and utilizing referrals to acquire clients. He also discusses the need for a centralized system to manage projects and communication, which led to the creation of Starting Point. Starting Point is a workflow management platform that allows teams, clients, and administrators to log in and see everything in one place. It offers features such as lead management, AI-powered proposal development, client onboarding, engagement management, file management, performance tracking, and invoicing. The platform was initially built for internal use by Red Beach Advisors but gained traction when shared with professionals in the consulting industry. The development of Starting Point was driven by the need to solve the challenge of scattered information and lack of visibility in managing projects and client relationships. Links LinkedIn: https://www.linkedin.com/in/raymondmckenzie/ Website: https://www.redbeachadvisors.com/ Website: www.startingpoint.ai Takeaways Building and maintaining relationships is crucial for business success.Leverage your corporate network and referrals to acquire clients.A centralized system for project management and communication is essential.Starting a business while still working full-time can be a viable option, depending on individual circumstances. Starting Point is a comprehensive workflow management platform designed for professional services and shared services organizations.The platform allows teams, clients, and administrators to have visibility and access to all relevant information in one place.Starting Point offers features such as lead management, AI-powered proposal development, client onboarding, engagement management, file management, performance tracking, and invoicing.The platform was initially built for internal use by Red Beach Advisors but gained popularity when shared with professionals in the consulting industry. Sound Bites "The people you're working with when you're 23, 25, 27, 29, fast forward 20 years, those are the people who are the VPs, the SVPs, the CEOs, the board directors of major companies.""These people are inherently receiving a community or a workforce bench of people and resources that they can use.""I just found myself not really having a great grasp as to everything that was going on.""It's a workflow management platform that allows your team to log in and see everything, your client able to log in and see everything.""I started showing it to people in professional services, consulting firms, people in my network. And as I started showing it to people in my network, they were like, hey, this is something we could use.""It's ideally meant to just be simple for people to be able to use." Chapters 00:00 Introduction and Catching Up 02:35 Transitioning from Corporate to Consulting 06:37 Managing Clients and Starting Red Beach Advisors 09:55 Starting a Business While Working Full-Time 16:16 The Inspiration Behind Starting Point 20:00 Introduction to Starting Point 29:02 Features and Benefits of Starting...

    42 min

  4. OCT 22

    Recalculating Life’s Path: Nina Sossamon-Pogue’s Blueprint for Building Your Next Chapter

    In this episode of the Corporate Escapee Podcast, Nina Sossamon-Pogue shares her multifaceted journey from being a U.S. gymnast to a successful journalist, and then transitioning into the tech industry. She discusses the challenges she faced, including injuries and career setbacks, and emphasizes the importance of resilience, storytelling, and mindset in navigating life's transitions. Nina provides valuable insights on identifying personal skills, the significance of positive language, and the necessity of building a supportive network. She also introduces her framework for resilience, TIPS, and encourages listeners to envision their ideal life and take proactive steps towards it. Takeaways Nina emphasizes the importance of resilience in navigating life's challenges.She encourages listeners to identify their skills and how they can transfer to new opportunities.Storytelling is a crucial skill in business and personal branding.It's essential to visualize what you want your life to look like.Transitioning from corporate to entrepreneurship requires a mindset shift.Understanding the phases of life can help in managing expectations and experiences.Creating a personal timeline can provide clarity on past experiences and future goals.Positive language can significantly impact your mindset and how others perceive you.Building a support network is vital for success and personal growth.Nina's TIPS framework offers a structured approach to overcoming challenges. Sound Bites "It's okay to not be okay, but not to stay that way.""Your words become your reality.""You're either giving energy or taking energy." Chapters 00:00 Introduction to Nina's Journey 03:08 Navigating Life's Challenges and Career Transitions 06:06 Finding Your Skills and Purpose 09:02 The Importance of Storytelling in Business 11:48 Identifying What You Want in Life 14:54 The Shift from Corporate to Entrepreneurship 18:14 Understanding Time and Life's Phases 20:56 Creating Your Own Life Timeline 23:45 The Power of Language and Mindset 27:04 Building a Support Network 29:59 Framework for Resilience: TIPS 33:00 Skill Stacking for Career Success 36:02 Mindset for Job Seekers 38:55 The Importance of Positive Language 41:56 Final Thoughts and Upcoming Projects

    51 min

  5. SEP 30

    Newly Escaped: Adrienne Farrell's Escape from "Toxic" Corporate to Solo Freedom

    Hear from a recent corporate escapee and her journey so far. Adrienne Farrell is a corporate wellness consultant and the founder of the InnovateHerLab, a community for women exploring their career paths. She focuses on women's health and well-being in the workplace, recognizing the need to elevate this issue.  Adrienne's journey to becoming an escapee started when she experienced layoffs and a toxic work environment. She decided to take a leap of faith and prioritize her own voice and values.  She is passionate about advocating for women's health and believes that the corporate world needs to change to better support women.  Adrienne is currently balancing her corporate wellness consulting work with her side project, the InnovateHer Lab.  The conversation explores the opportunities and challenges of transitioning from corporate life to entrepreneurship. They discuss the benefits of being your authentic self, the rise of fractional work, and the importance of networking and finding a supportive community. They also touch on time management and prioritization as key factors in the success of solo entrepreneurs. The conversation ends with advice for those considering the entrepreneurial journey. Adrienne’s Links LinkedIn: https://www.linkedin.com/in/adriennel-farrell/ Website: adriennefarrell.com/  Takeaways Adrienne's transition from corporate to escapee was motivated by her desire for work-life balance, flexibility, and the ability to advocate for her own values.She is passionate about addressing the gap in women's health and well-being in the workplace and believes that organizations have a social responsibility to prioritize this issue.Adrienne's experience in setting up wellness programs in corporate roles has informed her current work as a corporate wellness consultant.She emphasizes the importance of having a support network and community when navigating the transition from corporate to escapee. Being your authentic self brings the most value and happiness.Fractional work offers flexibility and cost-effectiveness for companies.Building a supportive network and community is crucial for success.Time management and prioritization are key skills for solo entrepreneurs.Give yourself grace and embrace the learning process. Sound Bites "There's a real need to elevate women's health within the workplace.""Finding your community allows for authentic, transparent conversations without jeopardizing your current career.""Having the freedom of voice and advocating for what's important to me is incredibly rewarding and empowering.""The opportunity, I guess more than anything""There are opportunities to create the work that you want""The future of work is heading this way" Keywords corporate wellness, women's health, career exploration, escapee, toxic work environment, work-life balance, flexibility, support network, entrepreneurship, corporate life, authenticity, fractional work, networking, community, time management, prioritization, advice Chapters 00:00 Introduction and Overview 00:37 Adrienne's Work: Corporate Wellness and the Innovate Her Lab 05:07 Transitioning from Corporate to Escapee 08:29 Finding Your Voice and Advocating for What's Important 12:45 Addressing the Gap in Women's Health in the Workplace 15:30 Balancing Corporate Wellness Consulting and the Innovate Her Lab 20:00 Approaching Time and Focus as an Escapee 22:10 Transitioning from Corporate Life to Entrepreneurship 23:06 The Opportunity of...

    40 min

  6. SEP 23

    "I’d Rather Be Homeless": Laine Belcastro on the Ups and Downs of Escaping and Why She’ll Never Go Back

    In this episode, Laine Belcastro shares her journey from corporate marketing to becoming a solopreneur and email marketing consultant.  Laine discusses the importance of networking, finding your niche, and the challenges of pricing strategies. Laine emphasizes the significance of email marketing for business growth and introduces her new venture, Accountability Arcade, aimed at helping entrepreneurs set and achieve short-term goals.  The conversation highlights the balance of multiple revenue streams and the mindset shifts necessary for success in the solopreneur world. Laine’s Links LinkedIn: https://www.linkedin.com/in/lainemb/ Website: https://lmbdigimarketing.com/  Takeaways Laine has her own email marketing automation consulting business.Networking is crucial for solopreneurs to find opportunities.It's important to focus on a niche to avoid burnout.Pricing should reflect the value provided, not just time spent.Email marketing is a powerful tool for brand recognition.Consistency in email outreach is key to staying top of mind.Accountability can help entrepreneurs achieve their goals more effectively.Starting with a simple nurture program can keep contacts engaged.You don't need to have everything figured out to start your business.Taking action is more important than waiting for the perfect plan. Sound Bites "I'd rather be homeless than go back to corporate.""Networking is key for solopreneurs.""You don't need a website to get started." Chapters 00:00 Introduction and Background 02:02 Accountability Arcade Service 03:43 Leaving Corporate America and Starting a Business 07:57 The Power of Networking 10:01 Finding Your Niche and Specializing 13:19 Pricing Models for Solopreneurs 17:39 Flexible Pricing and Meeting Customer Needs 19:32 Effective Email Marketing Strategies 27:35 Creating an Accountability Group 31:25 Balancing Multiple Revenue Streams 34:16 Taking Action and Diving into Entrepreneurship

    39 min

  7. SEP 17

    From Both Sides: Jaidin McCann’s Insider Take on Fractional Work and Company Needs

    Jaidin McCann, owner of Jasper Consultancy, shares her journey of starting her own executive search firm and offering fractional work. She emphasizes the importance of personal branding and networking in the fractional space. McCann advises individuals to specialize in a specific area and build a strong referral network. She also highlights the need for market research and understanding the buyer's market. McCann encourages individuals to take the leap into fractional work and enjoy the journey. Jaidin McCann Links LinkedIn: https://www.linkedin.com/in/jaidinmccann/Jasper Consultancy: https://www.jasperconsultancy.com/  Takeaways Specialize in a specific area and build a strong personal brand to differentiate yourself in the fractional space.Networking and building relationships with others in the industry is crucial for success in fractional work.Conduct market research to understand the needs and demands of the market and position yourself accordingly.Embrace the challenges and enjoy the journey of starting your own business in the fractional space. Sound Bites "It's more work than you think it is, but it's so worth it.""The world is so much smaller than we think.""You can eliminate the negative people and choose who you want to work with." Chapters 00:00 Introduction and Background 03:00 Starting a Fractional Business: Personal Branding and Networking 08:03 Building a Strong Referral Network in the Fractional Space 14:05 Understanding the Buyer's Market: Market Research in Fractional Work 21:23 Advice for Individuals Pursuing Fractional Work 29:29 Conclusion and Final Thoughts

    39 min

  8. SEP 12 · BONUS

    Escapee Collective Session: Fractional 101 with Jake Stahl

    This is an audio recording of a recent Happy Hour and Learn Session for members of the Escapee Collective community. Jake Stahl shares his advice, perspective and best practices for thriving as a fractional leader. Jake Stall discusses the concept of fractional work and shares his experience in the field. He emphasizes the importance of building relationships and networking in order to succeed as a fractional professional. Jake also provides insights on pricing strategies and how to ask for referrals. He promotes the upcoming Frac 2024 conference as a valuable opportunity for learning and networking in the fractional industry. Guest Links: Jake Stahl LinkedIn: https://www.linkedin.com/in/jakestahl/  Frak2024: https://fractionalconference.com/  Takeaways Fractional work involves providing a certain amount of time and expertise to a company in return for high-level guidance and leadership.Building strong relationships and networking are crucial for success in the fractional industry.Pricing strategies should focus on the value provided rather than competing on price.Asking for referrals is an effective way to generate new business in the fractional field.The Frac 2024 conference is a valuable opportunity for learning and networking in the fractional industry. Sound Bites "Networking is not about attending as many groups as possible, but about being involved in quality groups where you can build meaningful relationships.""The more interest you show in someone, the higher your chances of getting a contract with them.""The higher your price, the more people perceive value and are willing to pay for your services."

    31 min
See All (264)

4.8
out of 5
33 Ratings

About

The Corporate Escapee Podcast is a resource for GenX professionals ready to break free from the constraints of corporate life and design a more intentional, fulfilling lifestyle. Hosted by Brett Trainor- who’s been on the escapee journey for nearly five years—and who’s been helping others make the leap for just over a year—this podcast goes beyond just replacing replacement to focus on a life built around four core pillars: Happiness, Wellness, Freedom, and Financial Stability. Every episode features real stories, practical advice, and actionable insights from successful escapees, subject matter experts, and thought leaders. We dive into the realities of building financial stability outside corporate, creating a sustainable work-life balance, and rediscovering personal joy and wellness along the way. Our Mission:
To empower 100,000 GenXers to escape corporate, reclaim their lives, and build an intentional life that reflects what truly matters. We believe that finding your first customer is easier than finding your next job—and that you don’t have to do it alone. Community, connection, and a fresh approach to work-life design are key. Key Themes: * Income Replacement Strategies: Practical paths to replacing corporate income with work that aligns with your lifestyle goals * Freedom and Autonomy: Stories of crafting a life on your own terms, from solo consulting to fractional leadership * Wellness and Happiness: Insights on prioritizing physical and mental well-being, and making time for the things that truly matter * Financial Stability: Building a reliable income stream without corporate constraints Whether you’re exploring the escapee path, in the process of making the leap, or simply want more freedom and fulfillment, The Corporate Escapee Podcast offers the insights and support you need. Join us, and let’s redefine success together

Information

You Might Also Like

To listen to explicit episodes, sign in.

Stay up to date with this show

Sign in or sign up to follow shows, save episodes, and get the latest updates.
Select a country or region

Africa, Middle East, and India

Asia Pacific

Europe

Latin America and the Caribbean

The United States and Canada