Start With A Win

Latest Episodes:

Quick Win - Leadership Starts With Your Attitude Sep 25, 2026

Show notes

Unlock the essence of leadership with a single guiding force: Attitude! 🌟 The journey of leadership commences with the energy you bring to the table. Whether it's a conversation, a statement, or an action, your attitude sets the tone.
Start with the right attitude, and watch the magic unfold! ✨ A positive, can-do approach filled with optimism and good spirit not only influences your perspective but also inspires those you lead. It's a ripple effect that shapes the dynamics of the entire team.
Leadership is, at its core, an attitude game. Begin with the intention of fostering a great attitude within yourself, and that positivity will resonate with your team. 🚀 Your quick win for today: embrace the power of attitude in leadership. Reflect on your approach, infuse it with positivity, and witness the transformation in your leadership journey.
Share your thoughts on how attitude plays a role in your leadership style! 💬 #LeadershipAttitude #PositiveLeadership #AttitudeMatters
⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱? ➡︎ https://adamcontos.com/myleadership
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Subscribe and Listen to the Start With a Win Podcast HERE:📱
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YT ➡︎ https://www.youtube.com/@AdamContosCEO
Apple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347
Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT
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Connect with Adam:
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Website ➡︎ https://adamcontos.com/
Facebook ➡︎ https://facebook.com/AdamContosCEO
Twitter ➡︎ https://twitter.com/AdamContosCEO
Instagram ➡︎ https://instagram.com/adamcontosceo/
#adamcontos #startwithawin #leadershipfactory

Quick Win - Mastering the Art of First Impressions Sep 18, 2026

Show notes

Mastering first impressions isn't just about the handshake and smile—it's about genuine interest and leaving a lasting positive impact. Start with warmth and curiosity, ask great questions, and end with gratitude and a smile. These steps build relationships that last.
#FirstImpressions #RelationshipBuilding #PositiveImpact
⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱? ➡︎ https://adamcontos.com/myleadership
===========================
Subscribe and Listen to the Start With a Win Podcast HERE:📱
===========================
YT ➡︎ https://www.youtube.com/@AdamContosCEO
Apple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347
Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT
===========================
Connect with Adam:
===========================
Website ➡︎ https://adamcontos.com/
Facebook ➡︎ https://facebook.com/AdamContosCEO
Twitter ➡︎ https://twitter.com/AdamContosCEO
Instagram ➡︎ https://instagram.com/adamcontosceo/
#adamcontos #startwithawin #leadershipfactory

Jill Reilly: Your AI Strategy Isn’t Enough Sep 16, 2026

Show notes

In this Start With a Win episode, you'll meet Jill Riley, a global change strategist who's spent decades helping people break free from outdated systems. Discover the power of the '10 Permissions' and learn how to navigate profound change in your life and business. Join host, Adam Contos for a conversation that challenges you to unlearn the old rules and give yourself permission to write new ones. Get ready to step into transformation and reinvention with Jill's insights from post-apartheid South Africa to AI-era classrooms.
Jillian Reilly - author, global change strategist, and creator of The Ten Permissions. She works at the intersection of personal development, social disruption, and future readiness - helping people rethink what it means to live, work, and thrive in a world that’s rewriting its rules in real time.
For 30 years she worked on the frontlines of change - from post-apartheid South Africa to AI-era classrooms. Jillian helped people across generations break out of outdated systems and write new scripts for their lives. Now bringing that expertise to leaders, students, educators, and parents navigating an unpredictable future.
00:00 Intro
02:27 Thinking it was a six-month trip!
04:10 Unlearn to give yourself permission to learn the new
06:30 If you don’t embrace this way, you will miss out!
09:47 No, leaders are not ready…they need to own this!
14:28 Thought on AI and how to build into culture
18:35 Four great questions to frame the conversations…
23:58 It is as simple as this…
Website: https://tenpermissions.com/
LinkedIn: https://www.linkedin.com/in/jillianreilly/
===========================
Subscribe and Listen to the Start With a Win Podcast HERE:📱
===========================
YT ➡︎ https://www.youtube.com/@AdamContosCEO
Apple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347
Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT
===========================
Connect with Adam:
===========================
Website ➡︎ https://adamcontos.com/
Facebook ➡︎ https://facebook.com/AdamContosCEO
Twitter ➡︎ https://twitter.com/AdamContosCEO
Instagram ➡︎ https://instagram.com/adamcontosceo/
#adamcontos #startwithawin #leadershipfactory

Cindy Waddle: 2025 Start With a Win Holiday Special Dec 17, 2025

Show notes

In this holiday edition of Start With a Win, Adam Contos sits down with entrepreneur and former HR executive Cindy Waddle for a powerful conversation on trust-based leadership, human connection, and building cultures where people truly commit - not just comply. From compassion and accountability to purpose-driven business and heart-led influence, this episode explores what it really means to lead people in today’s world. Blending leadership wisdom, personal journey, and a touch of holiday fun, this episode will challenge how you think about empathy, motivation, and the lasting impact leaders can have - inside and outside the workplace.

To leave lasting imprints on hearts when they’re needed most, rising through the ranks to GS-14 without a college degree during her 38-year federal career, former HR Director of the U.S. Mint at Denver, Cindy Waddle turned her life’s challenges into that purpose. After surviving near-death experiences and proving that grit and determination can outshine any credential, she followed her passion to uplift others by founding Dezire to Inspire (D2I). What began as a heartfelt act - writing 365 inspirational cards for a grieving family while volunteering in hospice - grew into a mission-driven company creating inspirational cards, flip books, and programs that promote healing, resilience, and connection. Featured as the Cover Star of Female Entrepreneurs Magazine (July 2025), Cindy’s story embodies perseverance, purpose, and the transformative power of words to change lives.

00:00 Intro
02:35 What could happen if you got to know someone…
05:20 These really do have power!
09:19 Can leaders connect with heart?
11:24 Could this be what real leadership is about!
13:25 What would the leadership theme be?
16:40 Will you remember or believe if you got this…
18:52 Holiday trivia time…with great leadership advice!
24:25 It is before I even get out of bed…

https://www.deziretoinspire.com/

===========================
Subscribe and Listen to the Start With a Win Podcast HERE:📱
===========================
YT ➡︎ https://www.youtube.com/@AdamContosCEO
Apple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347
Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT

===========================
Connect with Adam:
===========================
Website ➡︎ https://adamcontos.com/
Facebook ➡︎ https://facebook.com/AdamContosCEO
Twitter ➡︎ https://twitter.com/AdamContosCEO
Instagram ➡︎ https://instagram.com/adamcontosceo/

#adamcontos #startwithawin #leadershipfactory

Jon Marashi: How He Built a $1 Billion Company Dec 03, 2025

Show notes

⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱? ➡︎ https://adamcontos.com/myleadership
Want weekly leadership content? Go here ➡︎ https://adamcontos.com

In this inspiring episode of Start With a Win, host Adam Contos sits down with Dr. Jon Marashi - the renowned cosmetic dentist trusted by Hollywood’s elite - to uncover how he transformed raw ambition into a thriving, world-class practice. From humble beginnings and bold cross-country leaps of faith to mastering a craft most said was impossible, Dr. Marashi shares the mindset and relentless drive behind his journey to the top of one of the most competitive industries. Packed with insights on risk, resilience, mentorship, and the real meaning of success, this conversation challenges you to rethink perfection, passion, and the courage to simply begin.

Dr. Jon Marashi is a renowned leader and innovator in the field of aesthetic dentistry, known for his highly personalized approach to smile restoration. Using microscope-level precision, he hand-sculpts each smile to create natural, artistic results that have earned him widespread recognition and a devoted patient base. A graduate of the prestigious Honors Aesthetic Dentistry program at NYU, he went on to teach in its Aesthetic Advantage program and later served as Clinical Program Director at the California Center for Advanced Dental Studies. He has also consulted for a major dental manufacturer, contributing to the development of new products and materials. Outside the clinic, Dr. Marashi is famously known as the “skateboarding dentist” in Los Angeles, where he finds balance cruising the streets on his board. He also serves as a founding board member of Learning Lab Ventures, a nonprofit focused on breaking the cycle of generational poverty through intensive after-school education.

00:00 Intro
02:34 In junior high I had deep love and appreciation!
05:59 Classmates laughed however look where it can take you…
08:10 This is the unfortunate part of human nature…
11:08 How do you know which five are the right ones?
16:20 Look for someone retiring?
19:40 This and this is not a bad thing!
21:10 More levels of success in life, it is a morally and ethically responsibility to do this!
23:45 Most proud moment in business…
26:05 I have this mantra and I repeat it…

The Skatepark Project
https://drmarashi.com/
https://www.instagram.com/drjonmarashi/#
https://www.linkedin.com/in/dr-jon-marashi-14a0a0167/

#adamcontos #startwithawin #leadershipfactory

Steve Cadigan: Interview With LinkedIn's Very First Chief HR Officer Nov 19, 2025

Show notes

What if everything we thought we knew about loyalty, leadership, and the future of work is about to be rewritten? In this episode of Start With a Win, Adam Contos sits down with Steve Cadigan - LinkedIn’s first-ever Chief Human Resources Officer and one of the most respected minds in global talent strategy - to explore the shifting realities of today’s workforce. From the rise of a restless generation to the untapped power of learning and mobility inside organizations, this conversation challenges leaders to think beyond old models of retention and success. It’s a provocative look at how businesses can thrive amid constant change - and why the key to keeping your best people might be the very thing that sets them free.

Steve Cadigan is a globally recognized talent advisor and founder of Cadigan Talent Ventures, a Silicon Valley firm that has worked with top organizations like Google, Intel, and the BBC. As LinkedIn’s first CHRO, he guided the company through its IPO and shaped its culture, which later became the foundation for a Stanford University course. With over 25 years of HR leadership, he has advised leading VC and consulting firms such as Andreessen Horowitz, McKinsey, and Deloitte. A sought-after speaker and media expert, he frequently appears on Bloomberg, CBS, and CNBC and teaches at major universities. His book, Workquake, debuted as a #1 Amazon Hot New Release in 2021. Recognized annually since 2021 as a top 100 thought leader in talent, he serves on multiple boards and advisory panels, helping leaders craft innovative talent strategies. Having lived and worked in Singapore, Canada, and the U.S., he brings a global perspective to the future of work. Based in California, he enjoys coaching basketball and playing tennis.

00:00 Intro
02:15 This is my moment…have you found yours?
03:40 This is the last thing companies think about!
05:05 Ways of winning without a team that has been together for a long time
08:25 The need for this has accelerated!
11:01 A person is loyal to this
13:30 CEOs need to do a better job in removing the silo thinking
18:30 Would you rather…?
20:50 Advice, listen up!
23:30 I do this for my twins

https://stevecadigan.com/
https://www.linkedin.com/in/cadigan/
steve@cadiganventures.com
https://www.tiktok.com/@stevecadigan?lang=en

#adamcontos #startwithawin #leadershipfactory

Adrian Koehler: This Is Why Most Business Coaching is Bullshit Nov 05, 2025

Show notes

Get ready to challenge everything you think you know about leadership and coaching. In this episode of Start With a Win, Adam Contos sits down with Adrian Koehler, a fearless executive coach who has worked with everyone from Navy SEALs to global innovators. Together, they dig into the raw, unfiltered realities of leadership - where broken commitments, uncomfortable truths, and radical authenticity collide. This conversation isn’t about clichés or motivational platitudes - it’s about the real work of transformation, the conversations most leaders avoid, and the hidden dynamics shaping success. Buckle up; this one will make you rethink how you lead, relate, and show up in every part of your life.

Adrian Koehler is a no-nonsense leadership expert and Senior Partner at Take New Ground, known for helping fast-moving leaders cut through the noise and drive real transformation. He coaches executives around the world - ranging from Fortune 500 giants to startups and healthcare innovators - fostering authentic leadership and courageous change. As co-host of Raising The Bar and The Naked Leadership Podcast, Adrian brings bold insights from his diverse background in philanthropy, ministry, activism, and medicine. Based in Hollywood with his kids, Scout and Charli, he’s on a mission to challenge leaders to live and lead with purpose.

00:00 Intro
02:03 The bowl is never empty…
05:44 No ice breakers here…
08:02 Locust of Control Conversation!
11:01 Hold up the mirror…
14:45 They double down on vision however need to double down on this!
19:30 Why do leaders sit on knowledge and not take action?
24:13 Not only is this a leadership gap, it a human gap!
33:10 Key tip to open the door…
36:48 A moment of pause…
https://adriankoehler.com/
https://www.instagram.com/adrian.k/
https://www.linkedin.com/in/adriankoehler/
https://takenewground.com/

#adamcontos #startwithawin #leadershipfactory

Jim Stevenson: How to Build Team Culture in 2025 Sep 17, 2025

Show notes

This episode of Start With a Win dives deep into the heart of leadership and culture with Jim Stevenson, founder and CEO of The Bletchley Group. From global brands to scrappy startups, Jim has been in the trenches helping businesses transform, scale, and thrive. Adam and Jim uncover why culture is the true engine of growth, how leaders unknowingly sabotage their teams, and what it really takes to build organizations that win. Packed with candid stories, hard-earned lessons, and bold insights, this episode challenges leaders to rethink how they hire, trust, and empower their people. If you’re ready to sharpen your leadership edge and uncover what truly drives sustainable success, you won’t want to miss this one.

Jim Stevenson is the founder and CEO of Bletchley Group, a renowned International Growth Consultancy with 23 years of expertise in strategy, transformation, and growth. He established Bletchley Group with a fundamental belief that while technology is powerful, it should always serve a meaningful purpose. Jim's unique value stems from his diverse background, having worked in numerous roles across a wide array of companies. This experience has provided him with a valuable bird's-eye view of business operations, enabling him to identify common mistakes made by businesses.

00:00 Intro
02:38 What is first to focus on, if you get it right everything else becomes easy?
06:01 Customer this is the key point!
07:43 Great concept is…
10:02 Follow special forces on this…
14:30 Might need to check your HR process…
17:02 Your job as a leader is to do this!
23:30 Common problems from leaders and stop doing them.
26:02 I realized and I changed my routine…

w: www.bletchleygroup.com
l: http://uk.linkedin.com/in/jimstevenson
t: http://twitter.com/JimStevenson

#adamcontos #startwithawin #leadershipfactory

Dr. Alexa Chilcutt: How to Improve Your Executive Presence Instantly Sep 03, 2025

Show notes

In this powerful episode of Start With a Win, Adam Contos is joined by Dr. Alexa Chilcutt - executive presence expert and faculty lead at Johns Hopkins Carey Business School - for an eye-opening conversation about what it really takes to lead with confidence, credibility, and authenticity. From navigating imposter syndrome to mastering the unspoken signals that define how others perceive you, this episode uncovers the often-overlooked elements that can elevate -or quietly undermine - your leadership. If you've ever wondered why some leaders inspire trust and authority the instant they enter a room, this is the episode you can’t afford to miss.

Alexa Chilcutt, Ph.D. is a nationally recognized expert in executive presence, team communication, and professional public speaking. She is the Faculty Lead for the Business Communication Certificate at Johns Hopkins Carey Business School and co-leads the Academy for Women and Leadership. In addition to her work at Johns Hopkins, she designs custom corporate training programs and teaches executive education for Texas Christian University and The University of Alabama. A certified Executive Coach, Chilcutt specializes in leadership development for women and technical professionals. She is also the founder of Maestro CE LLC, delivering tailored communication coaching and programs for corporate clients. Previously, she directed The University of Alabama’s Public Speaking Program for over a decade and developed communication curricula for UAB’s Dental School and NSF-funded engineering research programs.

00:00 Intro
02:51 What is executive/leadership presence?
05:34 If you are not doing this that scares you then you are not taking this…
09:08 How to deliver this without being egotistically?
10:44 Professional vs Personal Values
13:35 One of the biggest questions on executive presence?
18:10 Action to take - What is your judgement of them as a leader?
22:50 How to own the space?
24:15 Difference between good and great leaders!
26:36 Key piece of wisdom!
29:12 Grounded?

Https://www.linkedin.com/in/alexa-chilcutt-phd/

#adamcontos #startwithawin #leadershipfactory

Vijay Pendakur: The #1 Leadership Mistake You're Making That RUINS TRUST Aug 06, 2025

Show notes

In this episode of Start With a Win, host Adam Contos is joined by leadership strategist and author Dr. Vijay Pendakur to explore what it really takes to lead through disruption. Drawing from his experience at top tech companies and Cornell University, Vijay unpacks the secret to building high-performing teams when the ground is constantly shifting beneath you. From the invisible forces of trust and belonging to the raw challenges of leading through crisis, this conversation offers a bold reframe of leadership - one that is both deeply human and urgently practical. If you've ever wondered how to turn volatility into opportunity, this episode is your blueprint.

Dr. Vijay Pendakur is the founder of Vijay Pendakur Consulting and a seasoned leader across tech and higher education, with senior roles at Zynga, VMware, Dropbox, and Salesforce. He previously served as Dean of Students and Presidential Advisor for Diversity and Equity at Cornell University. Vijay’s upcoming book, The Alchemy of Talent (Dec 2024), is a practical guide to building high-performing teams. He also authored Closing the Opportunity Gap (2016), a widely used resource on equity in student success. A faculty member at USC’s Race and Equity Center and recognized as a top DEI leader by Channel Futures and Untapped, he also advises Ezra Coaching and Enterprise Ireland. Vijay lives in Austin, Texas, with his wife, Katie, and their two daughters, Mira and Savi.

00:00 Leadership Is About Relationship
00:29 Welcome to Start With a Win
00:55 Introducing Dr. Vijay Pendakur
02:03 From Education to Corporate Disruption
04:02 Growth Happens Through Pain
06:28 Why “The Alchemy of Talent”?
09:33 Leading Teams Through VUCA
13:07 Trust, Belonging, Connection Framework
15:08 How to Build Trust as a Leader
27:46 Where to Find the Book + Final Thoughts

https://www.vijaypendakur.com/

#adamcontos #startwithawin #leadershipfactory

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