Success Leaves Clues with Robin Bailey and Al McDonald

A Starting with One Podcast
  • 5.0 (2)
  • 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. 14h ago

    Success Leaves Clues: Ep 301 - If Not Now, When? Reinventing Yourself in Midlife with Brenda Benard, COO at Benard + Associates

    What if the most meaningful chapter of your life hasn’t happened yet?  In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Brenda Benard, COO at Benard + Associates, to explore midlife reinvention, overcoming self-doubt, and finding the courage to create a life that reflects who you are becoming. Brenda never planned to become a business leader. After turning down an opportunity to study theatre, struggling with low confidence, and believing her happiness would come from other people, she spent years moving through life without a clear sense of what she wanted. But a quiet voice continued reminding her that she was capable of more. Brenda shares why walking into a room filled with CEOs changed how she saw her own value, what her professional-athlete daughter taught her about self-belief, and how perimenopause affected her confidence, identity, and mental health. She also explains why asking “What’s the worst that could happen?” can make intimidating decisions feel possible. Robin, Al, and Brenda discuss intentional aging, protecting your health, listening to the whispers that tell you something needs to change, and refusing to postpone meaningful experiences until someday. Whether you’re questioning your career, navigating midlife, rebuilding your confidence, or wondering whether it’s too late to make a change, this episode is a powerful reminder that today is the youngest you will ever be again. You’ll hear about: Why Brenda calls herself the “reluctant COO”How self-doubt shaped Brenda’s early life and career decisionsWhy she turned down her dream of studying theatreBecoming a police officer at 33 while raising two young daughtersHow to recognize the quiet signs that you are capable of moreThe question that changed Brenda’s outlook on time and opportunityWhy taking responsibility can be more empowering than assigning blameThe moment Brenda realized she deserved to have her success celebratedHow other people may see strengths you cannot yet recognize in yourselfOvercoming feelings of inferiority around senior leaders and executivesWhy even the most accomplished leaders are still figuring things outHow perimenopause can affect confidence, identity, and mental healthWhat Brenda’s daughter taught her about making her younger self proudHow evaluating the worst-case scenario can help you move through fearWhy health and longevity have become central to Brenda’s next chapterThe power of trading expectation for appreciation We talk about: 00:00 Introduction to Brenda Benard and rethinking success in midlife 03:43 Self-doubt, abandoned dreams, and expecting happiness from others 05:02 Listening to life’s whispers and becoming a police officer at 33 08:41 “If not now, then when?” and why someday may never arrive 11:31 The moment Brenda decided she deserved to have her success celebrated 13:53 How Brenda’s employees saw strengths she couldn’t recognize in herself 21:06 Walking into a room of CEOs and overcoming feelings of inferiority 26:00 Perimenopause, self-confidence, and navigating the dark years 27:52 What Brenda’s daughter taught her about honouring her younger self 29:42 Using the worst-case scenario to move through fear 31:02 Raising courageous daughters and refusing to waste more time 33:10 Intentional aging, protecting your health, and living while you can 38:57 Trading expectation for appreciation Connect with Brenda LinkedIn: https://www.linkedin.com/in/brenda-benard-4a259188Website: www.benardinc.com   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    Success Leaves Clues: Ep 301 - If Not Now, When? Reinventing Yourself in Midlife with Brenda Benard, COO at Benard + Associates

  2. 6d ago

    Success Leaves Clues: **Ep 300** - Why People Strategy Is a Growth Lever with special guest Joanna Kmiec, CPO at Loopio

    What if people strategy was treated as a driver of growth rather than an HR cost centre? For the milestone **300th** episode of Success Leaves Clues, Robin Bailey and Al McDonald welcome back Joanna Kmiec, Chief People Officer at Loopio and one of the people who helped shape the direction of the podcast. Joanna challenges the idea that a Chief People Officer’s job is simply to keep employees happy. The real mandate is to build an organization that can grow, perform, and endure, without losing the humans inside the org chart. That requires business fluency, empathy, accountability, systems thinking, and the courage to speak up when everyone else in the room agrees. She explains how a strong people strategy reduces organizational drag, improves time to productivity, strengthens manager effectiveness, and allows senior leaders to spend more time building instead of repairing. Joanna also shares which workforce metrics matter, how people leaders can connect their work to business performance, and why the story behind the data is often more valuable than the number itself. Whether you are a CEO, founder, people leader, HR professional, or executive scaling a growing company, this episode offers a candid look at what strategic people leadership requires and how it can become a genuine lever for organizational growth. You’ll hear about: What a Chief People Officer is actually responsible for Why people strategy should be treated as a growth lever How culture can accelerate or obstruct business strategy Why people outcomes belong to managers, not only HR How to be bold without sacrificing kindness Measuring time to productivity and manager effectiveness Identifying and reducing organizational drag Why responsibility without authority causes leadership burnout How HR leaders can protect themselves during periods of chaos The quieter strengths that define exceptional leadership Why great employees sometimes leave great companies How former employees can become lifelong brand ambassadors Why creating other leaders is one of leadership’s greatest successes Using persistence and setbacks to move closer to a breakthrough We talk about: 00:00 Celebrating 300 episodes of Success Leaves Clues  03:02 The real role of a Chief People Officer  06:16 How strategic HR leadership has evolved  09:47 Becoming comfortable with tension as a leader  14:33 Why people strategy is a growth lever  18:14 Measuring the impact of people initiatives  22:23 What causes burnout among HR leaders  28:00 Staying calm and healthy during organizational chaos  34:38 The quieter qualities of exceptional leaders  38:00 Why great employees leave great companies  42:02 Why real leaders create other leaders  44:33 The advice that shaped Joanna’s leadership Connect with Joanna LinkedIn: https://www.linkedin.com/in/joanna-kmiec-chrl/ Website: https://loopio.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    Success Leaves Clues: **Ep 300** - Why People Strategy Is a Growth Lever with special guest Joanna Kmiec, CPO at Loopio

  3. Jul 21

    Success Leaves Clues: Ep 299 What Gets Recognized Gets Repeated | Kristian Gaetano, COO at Achievers

    What if one of the most effective ways to improve employee engagement, workplace culture, and business performance costs nothing more than a thoughtful thank you? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Kristian Gaetano, Chief Operating Officer at Achievers, to explore why employee recognition is far more powerful than an annual award or expensive incentive. Since joining Achievers nearly 15 years ago, Kristian has progressed from customer success into the C-suite by volunteering to solve the complex problems others avoided. He shares how leaning into his strengths, embracing challenges before he felt fully qualified, and becoming known as a dependable problem-solver shaped his leadership journey. The conversation also explores how leaders can balance data with instinct, why information requires human context, and how Kristian uses a “worry list” and trusted truth tellers to manage high-stakes decisions. As AI reshapes the workplace, he offers an important reminder that technology remains a tool. Critical thinking, community, empathy, and human connection are still what move organizations forward. Whether you are a CEO, founder, people leader, customer success professional, or executive navigating the future of work, this episode offers a human-centred approach to building stronger teams, customer relationships, and organizations. You’ll hear about: How Kristian grew from customer success into the COO role Why tackling difficult problems can accelerate leadership growth How customer success has become a strategic partnership Balancing data, instinct, empathy, and human context Why senior leaders need trusted truth tellers How to stop late-night worries from controlling your thinking The biggest misconception about employee recognition Why everyday recognition can influence workplace behaviour The connection between employee engagement and customer experience Why AI must support people, not replace critical thinking How organizations can remain human during workplace transformation Helping other people recognize and reach their potential We talk about: 00:00 Welcome and introduction to Kristian Gaetano  03:02 Growing from customer success into the COO role  04:00 Solving the problems nobody else wants  06:13 Leaning into your strengths as a leader  12:00 Why the customer is not always right, but is never wrong  13:19 Using empathy and constructive tension with customers  15:17 Balancing data with instinct and experience  18:09 The weight of making high-stakes leadership decisions  19:19 Kristian’s late-night “worry list” strategy  20:14 Why leaders need trusted truth tellers  22:15 Adding human context to data and AI  25:53 The biggest misconceptions about employee recognition  27:20 Recognizing everyday behaviours, not only major achievements  29:00 How employee engagement affects business performance  30:53 When AI transformation makes employees feel disposable  32:52 Attracting, engaging, and retaining talent in the future  34:20 Why the future of work requires community and humanity  36:24 Planting trees by helping people reach their potential Connect with Kristian LinkedIn: https://www.linkedin.com/in/kristiangaetano/ Website: https://www.achievers.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    Success Leaves Clues: Ep 299 What Gets Recognized Gets Repeated | Kristian Gaetano, COO at Achievers

  4. Jul 16

    Success Leaves Clues: Ep 298 - How Great Leaders Build Workplace Belonging in Remote Teams with Stephanie Crombie, Employee Experience Manager at HeyOrca

    What makes people genuinely love where they work? In this episode of Success Leaves Clues, Robin Bailey is joined by special guest co-host Ashlea DesRoches for an inspiring conversation with Stephanie Crombie, Employee Experience Manager at HeyOrca, about the power of creating workplaces where people truly feel they belong. Drawing from a career that began in hospitality and took her around the world aboard cruise ships, Stephanie shares how memorable experiences, intentional leadership, and personalized employee journeys can transform workplace culture, especially in fully remote organizations. Rather than relying on generic perks or one-size-fits-all programs, Stephanie explains why today's most successful organizations create meaningful moments that help employees feel seen, valued, and connected from their very first day. From onboarding new hires to recognizing everyday contributions, she reveals practical strategies leaders can implement to improve engagement, retention, and long-term business success. Robin, Ashlea, and Stephanie also discuss remote culture, personalization, employee recognition, onboarding, belonging, leadership, workplace happiness, and why the way leaders make people feel will always matter more than any KPI. Whether you're a CEO, founder, HR leader, people manager, or someone passionate about building stronger workplace cultures, this episode offers actionable ideas for creating organizations where people thrive. You’ll hear about: Why employee experience extends far beyond perks and benefits Creating meaningful workplace moments that employees remember Building a culture of belonging in fully remote teams The connection between employee happiness and business success Why personalized recognition outperforms generic rewards How intentional onboarding increases engagement and retention Practical ways leaders can make employees feel seen and valued Recognizing effort throughout the journey, not just outcomes Voice and choice as the foundation of great employee experiences How small moments create lasting workplace cultures Why human connection remains leadership's greatest advantage We talk about: 00:00 Welcome and introduction to Stephanie Crombie 02:00 From hospitality to employee experience leadership 05:45 Why people remember how work made them feel 10:20 Building belonging in fully remote organizations 15:30 Spotting culture shifts before they become problems 17:30 Creating unforgettable onboarding experiences 22:20 Personalization versus automation in employee experience 27:00 Why generic perks no longer create engagement 28:15 The power of "Voice and Choice" 30:00 Happiness, belonging, and leadership culture 32:00 Planting trees for future employees 35:00 Final leadership lessons and closing thoughts Connect with Stephanie LinkedIn: https://www.linkedin.com/in/stephanie-crombie14/ Website: https://www.heyorca.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald Website: Aria Benefits and Life & Legacy Advisory Group

    Success Leaves Clues: Ep 298 - How Great Leaders Build Workplace Belonging in Remote Teams with Stephanie Crombie, Employee Experience Manager at HeyOrca

  5. Jul 9

    Success Leaves Clues: Ep 297 - Why Talent Strategy Is Your Biggest Competitive Advantage with Kristin Condon, Chief Talent Officer at Sales Talent Agency

    Has AI made hiring easier, or has it simply made recruiting more complicated? In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Kristin Condon, Chief Talent Officer at Sales Talent Agency, to explore how artificial intelligence is reshaping recruitment, leadership, and the future of work. With more than 25 years of experience advising founders, CEOs, CHROs, and executive teams across North America and the UK, Kristin has helped organizations make more than 4,000 successful hires. She explains why the companies winning today's talent market aren't relying on AI alone. They're building authentic leadership, investing in employer branding, and creating cultures where people want to stay. The conversation dives into the growing disconnect between AI-generated applications and the highly sought-after passive candidates companies actually want to hire. Kristin shares why attracting top performers now requires stronger leadership, greater transparency, and a talent strategy that's every bit as intentional as a company's revenue strategy. Robin, Al, and Kristin also discuss employer branding, succession planning, leadership development, candidate experience, and why curiosity, adaptability, and human connection are becoming even more valuable in an AI-driven world. Whether you're a CEO, founder, HR leader, hiring manager, or professional navigating today's evolving workplace, this episode offers practical insights into building organizations where both businesses and people thrive. You’ll hear about: How AI is transforming recruitment and hiring Why more applications don't necessarily mean better candidates The growing importance of employer branding Why passive candidates are today's most competitive talent How leaders can retain high performers in an evolving workplace The leadership qualities employees are looking for today Why authenticity and transparency build stronger teams Helping junior talent succeed in an AI-driven economy Why curiosity and adaptability matter more than ever Building succession plans for long-term business success The connection between talent strategy and business growth Why CEOs should treat talent strategy like revenue strategy Creating candidate experiences that attract top performers How human connection remains a competitive advantage We talk about: 00:00 Introduction to Kristin Condon and Sales Talent Agency 02:00 How AI is changing recruitment and talent acquisition 06:00 Why hiring has become more competitive, not easier 09:15 What employers should look for in future talent 13:45 Why employer branding matters more than ever 17:30 The founder's role in attracting top candidates 20:00 Leadership qualities that retain exceptional people 23:40 Why employees quietly disengage and leave 27:00 The power of vulnerability and transparency in leadership 31:00 Why talent strategy deserves the same focus as revenue strategy 33:00 Building a legacy through connection, contribution, and community Connect with Kristin LinkedIn: https://www.linkedin.com/in/kristincondon00/ Website: https://www.salestalentagency.com/   Connect with Us LinkedIn: Robin Bailey and Al McDonald  Website: Aria Benefits and Life & Legacy Advisory Group

    Success Leaves Clues: Ep 297 - Why Talent Strategy Is Your Biggest Competitive Advantage with Kristin Condon, Chief Talent Officer at Sales Talent Agency

  6. Jul 2

    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

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

  7. 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

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

  8. 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

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

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