Success Leaves Clues with Robin Bailey and Al McDonald

A Starting with One Podcast
  • 5.0 (15)
  • Entrepreneurship
  • Updated Weekly

"If your actions inspire others to dream more, learn more, do more and become more ... you are a leader." ~ John Quincy Adams. We love sending our listeners on a journey of discovery as they learn about the inspiring lives of industry thought leaders, business owners, & entrepreneurs from all walks of life, who share one thing in common – SUCCESS! And it all starts with one—one idea; one conversation; one dream. Brought to you by Aria Benefits and Life & Legacy Advisory Group

  1. Success Leaves Clues: Ep 296 How Healthcare Innovation Improves Patient Access with John Leombruno, CEO at OkRx

    5 hrs ago

    Success Leaves Clues: Ep 296 How Healthcare Innovation Improves Patient Access with John Leombruno, CEO at OkRx

    What happens when life-saving medications exist, but patients still can't access them? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with John Leombruno, CEO of OkRx, healthcare entrepreneur, pharmacist, and former founder of Patient Direct Pharmacy and GMD Distribution, to explore one of healthcare's biggest hidden challenges: helping patients get the medications they need without being buried in paperwork, outdated systems, and administrative delays. John shares how witnessing breakthrough treatments transform children's lives at SickKids Hospital shaped his career and inspired him to focus on improving patient access rather than simply developing new therapies. That experience became the foundation for building businesses that simplify specialty medication access for patients, physicians, insurers, and pharmaceutical companies. The conversation explores why healthcare still relies heavily on manual processes, how digitizing prior authorization can dramatically reduce administrative burden, and why trust, relationships, and patient-first thinking remain essential when introducing innovation into one of the world's most complex industries. John also discusses entrepreneurship in healthcare, balancing innovation with patient safety, the realities of building trust across healthcare systems, and why lasting business success begins with solving meaningful problems. You’ll hear about: How a life-changing experience at SickKids Hospital shaped John's entrepreneurial journey Why patient access remains one of healthcare's biggest challenges The hidden barriers preventing patients from receiving specialty medications Why healthcare still relies on outdated administrative systems How digital prior authorization can transform patient care The importance of building trust before driving innovation Why patient-first thinking leads to better business decisions Balancing innovation with patient safety The role technology plays in reducing healthcare administration Building successful healthcare companies by solving real problems Lessons from multiple healthcare exits and entrepreneurial ventures Why relationships matter more than speed in healthcare innovation How healthcare technology can improve outcomes for patients and providers Creating meaningful impact through purpose-driven entrepreneurship We talk about: 00:00 Introduction to John Leombruno and OkRx 02:10 The experience at SickKids that changed John's career forever 05:15 Why breakthrough medications still don't guarantee patient access 07:00 What a truly patient-centered healthcare system should look like 10:20 Why specialty medications are becoming mainstream healthcare 11:00 Building OkRx to simplify specialty medication access 14:20 Balancing scientific thinking with entrepreneurial leadership 16:10 Why trust is healthcare's most valuable currency 18:00 How innovation succeeds one relationship at a time 21:00 Planting seeds that improve healthcare for future generations Connect with John: LinkedIn: https://www.linkedin.com/in/john-leombruno-4bb1777/ Website: https://www.okrx.ca/   Connect with Us: LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    22 min
  2. Success Leaves Clues: Ep295 - Building a Legacy Beyond the Exit with Nicholas Reichenbach, founder of Flow Water

    Jun 11

    Success Leaves Clues: Ep295 - Building a Legacy Beyond the Exit with Nicholas Reichenbach, founder of Flow Water

    What separates entrepreneurs who build companies from those who build legacies? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Nicholas Reichenbach, serial entrepreneur, private equity investor, conscious capitalist, and founder of Flow Water. Nicholas shares lessons from more than three decades of building and scaling businesses across technology, gaming, wellness, consumer products, and private equity. From creating Flow Water to launching Formosa Springs, a 155-year-old Canadian mineral water brand rooted in his family history, Nicholas explores what it means to build with purpose, patience, and long-term impact. Nicholas also challenges the traditional startup mindset, encouraging entrepreneurs to think beyond fast exits and focus instead on creating lasting prosperity for employees, communities, shareholders, and future generations. If you’re interested in entrepreneurship, conscious capitalism, sustainability, and building a lasting legacy, this episode offers powerful lessons from a founder who has spent decades turning vision into reality. You’ll hear about:  The entrepreneurial formula Nicholas uses to identify winning opportunities  Why conscious capitalism is becoming the future of business  How consumer behavior reveals untapped market opportunities  The environmental moment that inspired the creation of Flow Water  Building one of North America's most sustainable beverage brands  Why timing matters in entrepreneurship and innovation  How ESG principles can drive both impact and profitability  The importance of product obsession and consumer insight  Why legacy matters more than exits  The story behind Formosa Springs and its 155-year history  How family values influence long-term business decisions  Building brands designed to last for generations  The shift from hustle culture to sustainable leadership  Why purpose-driven companies outperform transactional businesses  Creating prosperity for employees, communities, and future generations  We talk about:  00:00 Introduction to Nicholas Reichenbach and his entrepreneurial journey 03:30 Building businesses across entertainment, technology, wellness, and consumer products 06:00 Why brand building is the common thread across every venture 07:30 The family history behind Formosa Springs and a lifelong connection to water 12:00 Growing up around one of Canada's historic mineral water sources 16:00 The first attempts to commercialize the family spring 18:00 Building technology companies and finding success in mobile entertainment 19:30 The Burning Man experience that inspired Flow Water 22:00 Creating a sustainable alternative to plastic bottled water 24:00 Acquiring and relaunching Formosa Springs 27:00 Understanding consumer intent and identifying market white space 30:00 The innovation behind Flow Water's packaging and product strategy 33:00 Why timing is critical for entrepreneurial success 35:00 Sustainability, ESG leadership, and conscious capitalism 39:00 Building businesses that create long-term positive impact 41:00 Legacy, leadership, and the future of entrepreneurship 44:00 Why founders should focus less on exits and more on longevity 46:00 Creating generational prosperity through purpose-driven business  Connect with Nicholas  LinkedIn: https://www.linkedin.com/in/nicholasreichenbach/  Website: https://formosasprings.com/    Connect with Us  LinkedIn: Robin Bailey and Al McDonald   Website: Aria Benefits and Life & Legacy Advisory Group

    42 min
  3. Success Leaves Clues: Ep 294 - The Mindset Behind Breakthrough Leadership with guest Hugh Chow, CEO at ventureLAB

    May 28

    Success Leaves Clues: Ep 294 - The Mindset Behind Breakthrough Leadership with guest Hugh Chow, CEO at ventureLAB

    What actually creates innovation? Is it technology, intelligence, funding… or something much deeper?  In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Hugh Chow, CEO at ventureLAB, inventor, entrepreneur, investor, and global innovation leader, to explore the mindset behind breakthrough leadership, meaningful innovation, and building companies that create lasting impact. With more than 30 years of experience across semiconductors, startups, venture capital, sustainability, and global technology, Hugh shares the deeply personal journey that shaped his perspective on leadership, opportunity, and resilience. From immigrating to North America to helping scale technology companies with hundreds of patents and hundreds of millions in revenue, Hugh unpacks what it really takes to build something meaningful in a rapidly changing world. This conversation explores the future of Canadian innovation, why founders need to think globally from day one, and how true innovation comes from challenging the status quo rather than accepting it. Hugh also shares why he believes leadership is about creating opportunities for others, lifting people up, and planting seeds for future generations to grow. Throughout the episode, Hugh offers powerful insights on entrepreneurship, commercialization, AI, hardtech, startup ecosystems, mentorship, and the lessons he learned from his parents that continue to guide his leadership today. If you’ve ever wondered what separates visionary leaders from everyone else, or how innovation can become a force for long-term impact, this episode delivers a masterclass in leadership, humility, and purpose-driven growth. You’ll hear about: Why innovation starts with challenging the status quo The leadership philosophy behind building win-win relationships How one phone call changed the trajectory of Hugh’s career Why great leaders recognize talent before people see it in themselves The difference between taking risks and creating opportunity Why Canadian founders need to think globally from the beginning The commercialization gap holding Canadian innovation back What makes Canada one of the strongest innovation ecosystems in the world The future of AI, hardtech, and medical technology startups Why learning matters more than avoiding failure The importance of sustainability and lifting others up How Hugh’s parents shaped his approach to leadership and resilience We talk about: 00:00 Introduction to Hugh Chow and ventureLAB02:00 Seeing potential in people before they see it themselves05:00 Why leadership is about creating win-win opportunities08:30 The career moments that shaped Hugh’s innovation mindset10:00 Moving to North America and starting in semiconductors13:00 Building a global technology company from Canada15:00 What innovation actually means in today’s world17:00 Why innovation requires challenging the status quo19:00 Leadership, sustainability, and creating long-term impact21:00 Canada’s strengths in innovation and AI23:00 Why Canadian companies must think globally25:00 Commercialization challenges in Canada28:00 The future of hardtech, AI, and medical technology31:00 What founders often misunderstand about success34:00 Supporting startups through uncertainty and change36:00 The question every leader should ask themselves38:00 Hugh’s parents, resilience, and the lessons that shaped his life42:00 Why opportunity should be passed on to future generations Connect with Hugh LinkedIn: https://www.linkedin.com/in/hugh-chow-445b332/ Website: https://www.venturelab.ca/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    38 min
  4. Success Leaves Clues: Ep 293 - The Leadership Behaviours that Shape Culture with Jessica Lewis of PointsBet

    May 21

    Success Leaves Clues: Ep 293 - The Leadership Behaviours that Shape Culture with Jessica Lewis of PointsBet

    What actually creates a great company culture? Is it the values written on the wall… or the behaviors happening behind closed doors? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Jessica Lewis from PointsBet to explore what it really takes to build high-performing teams, strong workplace cultures, and leadership environments where people genuinely thrive. Jessica shares her journey from executive assistant to senior people leader, unpacking the lessons she’s learned while scaling teams in fast-paced, high-growth organizations. From mentorship and strategic hiring to difficult feedback conversations and leadership accountability, this conversation reveals why culture is never owned by one person. It’s built collectively, reinforced daily, and tested most during difficult moments. This episode dives into the realities of modern leadership, including the growing role of AI in HR, the importance of trust and transparency, and why the best leaders understand that people strategy is business strategy. Jessica also shares her passion for creating more opportunities for women in leadership and building workplaces where more voices are welcomed to the table. If you’ve ever wondered why some organizations create loyalty, growth, and energy while others quietly lose their best people, this conversation offers a powerful look at what separates healthy cultures from performative ones. You’ll hear about: Why company culture is built through everyday behavior, not mission statementsWhat leaders reveal about culture behind closed doorsThe hiring mistake that quietly damages organizations over timeWhy technical skill alone is never enough for leadership successHow mentorship changes careers and builds long-term confidenceThe importance of giving feedback early and with kindnessWhy trust and transparency are critical for strong workplace culturesHow AI is reshaping HR and the employee experienceThe role frontline managers play in reinforcing company valuesWhy creating more women leaders matters for the future of business We talk about: 00:00 Introduction to Jessica Lewis and PointsBet02:00 From executive assistant to people leadership04:30 Why HR became Jessica’s purpose and passion06:30 Staying ahead in leadership through mentorship and community08:30 The connection between leadership and company culture10:00 What actually causes workplace culture to break down11:30 Why culture is revealed behind closed doors13:00 Hiring for values, not just technical competence15:30 How fast-growing companies redefine leadership needs17:00 Giving feedback early and building accountability19:00 Technical skill vs cultural alignment, which matters more?21:30 The leadership lessons mentorship creates23:30 Building confidence as a woman in leadership25:00 Why representation and equity in leadership matter26:30 The future of workplace culture and leadership Connect with Jessica LinkedIn: https://www.linkedin.com/in/jessica-lewis-86744352/ Website: https://on.pointsbet.ca/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    28 min
  5. Success Leaves Clues: Ep 292 - The Power of Bold Decisions and Relentless Persistence with Dan Turner, CEO at Xperigo

    May 14

    Success Leaves Clues: Ep 292 - The Power of Bold Decisions and Relentless Persistence with Dan Turner, CEO at Xperigo

    What if the only thing standing between where you are… and where you want to be… is one bold decision you haven’t made yet? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Dan Turner, CEO at Xperigo, to unpack a career built not on perfect timing or traditional paths, but on courage, persistence, and the willingness to step through doors before they fully open. Dan’s journey starts far from the boardroom, as an 18-year-old tow truck driver with no clear direction. But one moment, one story, one decision to believe something bigger was possible, set him on a path that would eventually lead him to the CEO seat. This conversation dives deep into what it really takes to grow into leadership, how calculated risks can redefine your career, and why the leaders who win today are the ones who lead with trust, vulnerability, and genuine care. From spotting opportunity before it’s obvious, to building a culture that fuels performance, to redefining what great leadership actually looks like, this episode is a powerful reminder that success is not a straight line, it’s a series of brave choices made consistently over time. If you’ve ever questioned whether you’re capable of more, or felt the pull toward something bigger but hesitated to act, this conversation will challenge you to rethink what’s possible. You’ll hear about: Why one moment of belief can completely change the trajectory of your lifeHow Dan Turner turned a bold hunch into a multi-million dollar opportunityThe real reason most people stay stuck in their comfort zoneWhy risk is required if you want to reach your full potentialHow confidence is built through action, not certaintyThe mindset shift that turns “failure” into growthWhy opportunity rarely announces itself, and how to spot it earlyHow proactive thinking separates top performers from everyone elseThe role persistence plays in long-term successWhy stepping outside your comfort zone is non-negotiable for growth We talk about: 00:00 Introduction to Dan Turner and Xperigo02:30 From tow truck driver to CEO, the origin story05:00 The moment that sparked a bold, long-term vision08:00 Why big goals feel overwhelming, and how to start anyway11:00 Comfort zones vs. growth, why staying safe keeps you stuck14:00 The Apple iPhone story, spotting opportunity before the world sees it17:30 Turning a bold idea into a multi-million dollar deal20:00 Risk, doubt, and why the upside is always worth it23:00 The mindset that separates leaders from followers25:30 Culture vs performance, why they fuel each other28:00 Building trust, transparency, and high-performing teams31:00 Leadership today, why vulnerability is a strength, not a weakness34:00 The future of leadership and building a legacy that lasts Connect with Dan LinkedIn: https://www.linkedin.com/in/turnerdan/ Website: https://www.xperigo.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    38 min
  6. Success Leaves Clues: Ep 291 - Stop Hiring for Resume. Start Hiring for Impact with Alison Kaizer, Partner at Golden Ventures

    Apr 30

    Success Leaves Clues: Ep 291 - Stop Hiring for Resume. Start Hiring for Impact with Alison Kaizer, Partner at Golden Ventures

    What if the reason your company isn’t scaling… has nothing to do with your product, and everything to do with who you hire? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Alison Kaizer, Partner of Talent at Golden Ventures, to break down the real mechanics behind building high-performing teams inside early-stage startups. Alison has helped scale companies from dozens to hundreds of employees, and now supports founders across an entire portfolio, shaping the people decisions that determine whether a company grows or stalls. This conversation pulls back the curtain on what actually makes a great hire, why most founders get it wrong, and how to build a hiring system that works before your company even knows what it needs. From ditching resume bias to hiring for aptitude, from building structured interview systems to creating transparency in compensation, this episode is a masterclass in hiring as a strategic advantage. If you’re building a team, scaling a company, or making critical early hires, this episode will completely shift how you think about talent. You’ll hear about: Why resume-driven hiring is one of the biggest mistakes founders make The difference between hiring for experience vs. hiring for aptitude How to identify high-impact talent before it’s obvious on paper Why past success doesn’t guarantee future performance The role of structured interviews in eliminating hiring bias How to build a repeatable hiring system that scales with your company The hidden cost of hiring “safe” candidates instead of adaptable ones Why early-stage companies should prioritize learning ability over playbooks How transparency in compensation builds trust and closes top candidates The real reason culture fit is often misunderstood and misused How to assess values in a short interview process without guesswork What founders need to understand about motivation, ambition, and timing We talk about: 00:00 Introduction to Alison Kaizer and Golden Ventures02:00 From consulting to recruiting, the unexpected career path05:30 Scaling talent functions inside high-growth startups08:30 The moment pattern recognition becomes a superpower11:00 The biggest hiring mistake founders make (resume bias)14:00 Why aptitude beats experience in early-stage companies17:30 How to build structured interviews that actually predict success20:30 The truth about “culture fit” and how to assess values properly23:30 Scaling hiring without lowering the bar26:00 Compensation transparency and building trust with candidates29:00 Hiring in startups vs. enterprise environments31:30 How AI is reshaping hiring and talent evaluation33:30 The future of work and why adaptability wins Connect with Alison LinkedIn: https://www.linkedin.com/in/alisonkaizer/ Website: https://www.golden.ventures/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    32 min
  7. Success Leaves Clues Ep. 290 - The Leadership Shift That Builds Companies That Last with Sarah O’Brien, Chief Operating Officer at SMS Security

    Apr 23

    Success Leaves Clues Ep. 290 - The Leadership Shift That Builds Companies That Last with Sarah O’Brien, Chief Operating Officer at SMS Security

    What happens when you inherit a legacy… but need to evolve it to survive? In this episode of Success Leaves Clues, Robin and Al sit down with Sarah O’Brien, Chief Operating Officer at SMS Security, to explore the real leadership transformation required to grow a family business into a scalable, modern organization. Sarah shares what it actually feels like stepping into a second-generation leadership role, navigating expectations, earning trust, and redefining what leadership looks like in a company built on legacy relationships. From letting go of being the problem-solver, to building systems that don’t rely on one person, to leading in a 24/7 high-stakes industry, this conversation unpacks the mindset and operational shifts required to build a company that lasts. If you’re leading a team, scaling a business, or transitioning leadership in any capacity, this episode will challenge how you think about control, trust, and long-term success. You’ll hear about: What it really means to step into leadership in a family business Why second-generation leaders are natural disruptors The hidden challenge of earning trust inside your own company How to shift from reactive problem-solving to scalable systems Why leadership can feel lonely and how to build external support The difference between technical competence and true trust-building How listening, not solving, creates stronger teams and clients Why consistency and communication define leadership credibility How to lead in a 24/7, high-pressure industry without burning out your team The mindset shift from being needed… to building something that doesn’t need you We talk about:  00:00 Introduction to Sarah O’Brien and SMS Security02:00 Transitioning from corporate to a family business04:30 The reality of stepping into leadership and earning trust07:00 Navigating legacy, expectations, and comparison to previous leadership10:00 Resistance, accountability, and evolving company culture13:00 Building support systems as a leader and overcoming isolation16:00 Leading in a high-stakes, reactive industry19:00 Customer trust, vulnerability, and service under pressure22:00 The power of listening and creating space in leadership25:00 Developing people and leading in a 24/7 environment28:00 Preventing burnout while maintaining high performance30:00 The shift from problem-solver to system builder33:00 Building a company that scales beyond any one person Connect with Sarah LinkedIn: https://www.linkedin.com/in/sarah-o-brien/ Website: https://www.smssecurity.ca/    Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    29 min
  8. Success Leaves Clues Ep. 289 - The Employee Experience Strategy with Alisha Patel, VP People & Culture at CanadaHelps

    Apr 9

    Success Leaves Clues Ep. 289 - The Employee Experience Strategy with Alisha Patel, VP People & Culture at CanadaHelps

    What if your employee experience strategy is the reason your business is either scaling… or stalling?  In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Alisha Patel, VP People & Culture at CanadaHelps, to unpack what it really means to design a workplace where people, performance, and business outcomes actually align.  Alisha brings a rare combination of people leadership and financial expertise, offering a perspective most organizations are missing. She breaks down why employee experience is not an HR function, but a business strategy, and how leaders can finally connect culture, retention, and performance in a way that drives real results.  From listening tours and multi-generational workforce design to global cultural nuance and flexible benefits, this conversation challenges the “one-size-fits-all” approach most companies are still relying on.  If you’re leading a team, building culture, or trying to retain great people in a rapidly changing workforce, this episode will shift how you think about leadership, investment, and what actually creates sustainable growth.  You’ll hear about:  Why employee experience strategy is a business function, not an HR initiative  How combining finance and people strategy changes leadership decisions  The real reason “people are our greatest asset” often falls flat  What listening tours are and how they shape high-impact people programs  Why one-size-fits-all benefits and policies are failing modern teams  How to design for five generations in today’s workforce  The connection between flexibility, retention, and productivity  Why culture must evolve across global teams and local contexts  How to build trust through clarity, not just perks or programs  The leadership shift from process-driven HR to experience design  Why humility, curiosity, and listening are the most underrated leadership skills  How mentorship and inclusive leadership shape future organizations  We talk about:  00:00 Introduction to Alisha Patel and her leadership background 02:00 How finance + people strategy creates better business decisions 04:00 Why employee experience is tied to business outcomes 06:30 What “people are our greatest asset” actually means in practice 09:00 Why most HR functions are too transactional 11:00 What a “listening tour” is and how to run one effectively 14:00 Designing benefits and programs based on real employee needs 17:00 Global workforce insights across Canada, US, Europe, and beyond 20:00 Why culture cannot be one-size-fits-all 22:30 The biggest missed opportunity in how companies invest in people 24:00 Flexibility as a low-cost, high-impact benefit strategy 26:00 Measuring success beyond usage, focusing on engagement and retention 28:00 Leadership legacy, mentorship, and building inclusive systems 30:00 Why listening is the most important leadership skill moving forward  Connect with Alisha  LinkedIn: https://www.linkedin.com/in/alishapatel/  Website: https://www.canadahelps.org/    Connect with Us  LinkedIn: Robin Bailey and Al McDonald   Website: Aria Benefits and Life & Legacy Advisory Group

    28 min
See All (327)

Ratings & Reviews

5
out of 5
15 Ratings

About

"If your actions inspire others to dream more, learn more, do more and become more ... you are a leader." ~ John Quincy Adams. We love sending our listeners on a journey of discovery as they learn about the inspiring lives of industry thought leaders, business owners, & entrepreneurs from all walks of life, who share one thing in common – SUCCESS! And it all starts with one—one idea; one conversation; one dream. Brought to you by Aria Benefits and Life & Legacy Advisory Group

Information

You Might Also Like