RadEO

Entrepreneurs Organization South Africa

Hello and welcome to RadEO a podcast by Entrepreneurs for Entrepreneurs. It is hosted by Ross Drakes. In this podcast, we share the stories of EO entrepreneurs, their personal stories, some insight into their entrepreneurial journey and the lessons from how they think about their business today.

  1. #67 Stephen Shortt | Why family business succession breaks people (and how to survive it)

    5D AGO

    #67 Stephen Shortt | Why family business succession breaks people (and how to survive it)

    We often fall into the lazy thinking that family businesses are easy to hand down. Stephen Shortt lived the messy reality. He grew up in two family businesses and nearly walked away from it all just to save his relationship with his parents. In this episode, we talk about escaping that trap and surviving succession without burning down the family home. We unpack the "five Ps of successful succession," why the ancient Celtic concept of "fosterage" beats nepotism, and how to build "inside hustles" to innovate safely. But we also explore what happens past the Give a Shit line. Building a multi-generational business is not just about keeping the lights on; it is about keeping relationships intact. Stephen and I dig into navigating imposter syndrome, jumping the innovation S-curve before you resent your own company, and making it matter for the next generation. Key Takeaways: The Five Ps: Use Purpose, Pick, Prepare, Promote, and Patience to navigate succession smoothly. Change the room: Move hard conversations out of the boardroom to neutralise power dynamics and build a partnership. Fosterage over nepotism: Send the next generation out to learn from other businesses before bringing them into yours. Inside hustles: Build new projects within the safety of your current business to test new ideas without risking the family home. Jump the S-curve: Recognise your wiring and have the courage to jump to the next innovation curve when the work becomes too focused on optimisation. More about Stephen Shortt:  Stephen Shortt is a career and talent strategist, family business facilitator, and the founding member of EO Ireland. He helps multi-generational businesses navigate succession and builds tools to help people find fulfilling, rewarding careers.

    36 min
  2. #66 Jason Rhoades | How AI gives us the space to actually be more human

    APR 28

    #66 Jason Rhoades | How AI gives us the space to actually be more human

    We are standing at the edge of the biggest technological shift of our lifetimes, and most businesses are reacting with lazy thinking. They adopt shiny new tools without a strategy, leading to a chaotic web of shadow AI and disconnected agents.  In this episode, I sit down with Jason Rhoades, founder of Meaningful AI, to cut through the noise. We unpack why building mediocre software is a necessary step in innovation and how to transition your team through the three gears of AI adoption, from individual productivity hacks to proactive, multi-agent orchestration. But this conversation is not just about technology; it is about what technology enables. Jason and I explore how offloading the mind-numbing drudgery of keyboard work gives us the space to be more human. By eradicating the b******t in our operations, we can finally obsess over every nook and cranny of the customer experience.  If you want to know how to use AI to cross the ‘Give a shit line’ and build authentic connections that actually make it matter, you need to hear this. Key Takeaways: Focus on value: Building software instantly with AI is useless if it does not solve a real pain point; you must make it matter for the customer rather than just adding to the noise. Shift through the three gears: True AI adoption moves from solving individual productivity issues, to team-level workflows, and finally reaches proactive, multi-agent orchestration. Establish a lighthouse strategy: Without central guidance, teams will adopt disconnected tools, creating a chaotic web of shadow AI and agentic sprawl. Eradicate the BS: AI will eliminate the lazy thinking of moving data between spreadsheets, allowing you to finally obsess over every nook and cranny of the customer experience. Make space to be more human: Offloading keyboard drudgery allows you to double down on creativity, curiosity, and empathy, ensuring your ideas actually cross the ‘give a shit line.’ More about Jason Rhoades Jason Rhoades is the founder and Chief Innovation Officer at Meaningful AI, a consultancy helping companies navigate the change management and implementation of artificial intelligence. An EO Atlanta member, Jason previously founded and successfully exited the UX/UI consultancy Toolbox No. 9, where he led digital experiences for brands such as Amazon, Cartoon Network, and Mercedes-Benz.

    46 min
  3. #65 - Mike Bodkin | The unexpected ROI of checking your entrepreneurial energy

    APR 13

    #65 - Mike Bodkin | The unexpected ROI of checking your entrepreneurial energy

    We often get trapped in the lazy thinking that offering more services equals scaling. Mike Bodkin lived this. He grew his digital marketing agency, Giant Propeller, by saying yes to everything from email to media buying until the business hit a hard plateau. In this episode, we talk about escaping the generalist trap, navigating the inevitable tension between co-founders, and finding a lucrative exit through pure serendipity and peer networks. But we also explore what happens past the Give a Shit line—that final 20% where true human connection lives. Building a business is not just about structural mechanics; it is about how you show up and make it matter. Mike and I dig into the "Ryan Reynolds effect" and why actively protecting your sleep, checking your energy, and displaying genuine excitement for your work are the sharpest tools you have for inspiring clients and attracting top talent. Key takeaways The "say yes" trap: Saying yes to every new service offering dilutes your focus and accelerates a revenue plateau. The Ryan Reynolds effect: Founder energy is infectious; true excitement for your business attracts clients and top talent. Serendipity requires proximity: Selling your business often requires being in the right networks rather than actively pitching to buyers. Roles over resemblances: Clearly defined co-founder roles prevent tension and streamline business operations. Subscribe on iTunes or Spotify More about Mike Bodkin Mike Bodkin is the co-founder and CEO of TalentScout, a niche recruiting agency placing senior marketing and creative talent from Latin America into US businesses. Before TalentScout, Mike spent 15 years in filmmaking and post-production, then co-founded and successfully exited the full-service digital marketing agency, Giant Propeller.

    41 min
  4. #61 Ami Kassar | From the kitchen table to global networks

    09/16/2025

    #61 Ami Kassar | From the kitchen table to global networks

    In this episode, Ross Drakes speaks to Ami Kassar, founder and CEO of Multifunding and creator of EO’s Grit Group. Ami shares how childhood memories of immigrant families around his kitchen table shaped his philosophy of generosity and peer learning. They explore the realities of starting again after corporate collapse, the discipline of saying no, and why business owners should focus on fundamentals before chasing shiny frameworks. This conversation shows how clarity, truth, and community can unlock resilience and growth. Key Takeaways: - Peer learning provides practical solutions faster than top-down advice. - Get the basics right before adding new systems or frameworks. - Access to flexible capital helps businesses handle uncertainty. - Turning down the wrong client creates better long-term outcomes. - Community and generosity are essential for sustainable growth. Subscribe on iTunes, Spotify, or Overcast. This episode is a reminder that entrepreneurship is sustained by generosity, honesty, and learning together around the ‘big kitchen table.’ More About Ami Kassar Ami Kassar is the founder and CEO of Multifunding, a national advisory firm that has helped thousands of entrepreneurs navigate the complex world of growth financing. He is also the creator of EO’s Grit Group, a member-led community that started as a WhatsApp group and now connects about 1,500 entrepreneurs for real-time support. He has advised countless entrepreneurs on financing strategies that align with their vision and values. He is the author of “The Growth Dilemma,” which shares insights on using debt and equity to unlock growth without losing control. Ami has dedicated his career to assisting business owners in making courageous, informed financial decisions that foster sustainable success and long-term freedom.

    35 min
  5. #60 Carrie Schochet | From Forced Entrepreneurship to Purple Squirrel Hunter: Building Success Through Community

    08/19/2025

    #60 Carrie Schochet | From Forced Entrepreneurship to Purple Squirrel Hunter: Building Success Through Community

    In this episode, Ross Drakes sits down with Carrie Schochet, founder of Purple Squirrel Advisors, who got "forced" into entrepreneurship when circumstances changed after maternity leave. From starting as a single recruiter competing against global firms to building a thriving business by hunting "purple squirrels" (the impossible-to-find perfect candidates), Carrie shares her strategic approach to finding opportunities in the spaces others avoid. The conversation covers her journey from pre-med to accidentally discovering recruiting, the power of community building, surviving a devastating ski accident that changed her relationship with her business, and why your identity as an entrepreneur shouldn't be tied to a single company. This is a story about resilience, strategic thinking, and the unexpected gifts that come from being forced out of your comfort zone. Key Takeaways: Find opportunities where others won't goCommunity is your competitive advantage Sometimes you need to be forced into your destinyYour identity should be an entrepreneur, not just your business The right team permits you to lead differently Subscribe on ⁠iTunes⁠, ⁠Spotify⁠ or ⁠Overcast⁠   More About Carrie Schochet Carrie is the Founder and CEO of Purple Squirrel Advisors, a boutique executive search firm based in Troy. Passionate about helping companies grow by creating exceptional leadership teams, she has spent the past 16 years connecting C-level and senior executives with leadership positions in finance, accounting, human resources, operations, sales, and marketing. After graduating from the University of Notre Dame in 2001, she spent over a decade advancing her career at one of the nation's leading recruitment and staffing firms in Chicago. In 2012, she moved back to the Detroit area to be closer to her family. On January 1, 2015, she founded Purple Squirrel Advisors with the mission of designing a consultative, white-glove recruitment process customised to each client. Carrie is also the founder of CFO Next, a group she launched in early 2013 after discovering a lack of resources and networking opportunities for transitioning or unemployed senior financial executives. She also uses her network and resources as Co-Chair of the Career Services Committee for Financial Executives International (FEI), a non-profit organisation with the mission to support senior finance executives through professional development and networking. She is the Learning Chair for the Entrepreneurs Organisation Detroit Chapter and sits on the ACG Detroit Board as Women's Forum Chair. Carrie is a passionate philanthropist who has raised money for 100 Women Who Care - Greater Rochester Area, and in 2016, co-founded 100 Businesses Who Care to connect executives who want to make a philanthropic impact on the Metro-Detroit community.

    45 min

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About

Hello and welcome to RadEO a podcast by Entrepreneurs for Entrepreneurs. It is hosted by Ross Drakes. In this podcast, we share the stories of EO entrepreneurs, their personal stories, some insight into their entrepreneurial journey and the lessons from how they think about their business today.