2 Min CxO Clip- Doug Gattuso
CXO Conversations
What does it mean to lead with authenticity in the C-suite? In this episode of CXO Conversations, Doug Gattuso talks about the importance of leaving ego at the door and focusing on creating value for people and organizations. He shares lessons from building teams, returning to companies multiple times, and leading international initiatives across Europe, Mexico, and India. Doug offers candid advice for those aspiring to executive leadership: don’t chase titles—invest in learning, seize opportunities, and always contribute to the bigger picture. For the full interview:...
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10 Min CxO Clip- Doug Gattuso
CXO Conversations
In “C-Suite Perspective in Leading with Authenticity,” shares why true leadership is about focusing on opportunities and outcomes—not titles or ego. A veteran of the Naval Academy and Marine Corps, Doug reflects on a career spanning executive roles including President and Chief Customer Officer. He explains why burning bridges is never wise, the lessons gained from international work experiences in Prague and India, and how patience, teamwork, and humility shape long-term success. Doug’s story is a reminder that authentic leadership and continuous contribution create lasting impact in...
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2 Min CxO Clip- Casey Woo
CXO Conversations
What does it take to admit a prestigious path isn’t for you—and have the courage to pivot? In this episode of CXO Conversations, Casey Woo, CFO of Landing.com, discusses his journey from West Point to Harvard, from Wall Street hedge funds to executive leadership roles at startups like WeWork and Zozi. Casey shares how he found fulfillment in finance by building teams, driving strategy, and embracing the operational challenges of scaling businesses. Along the way, he offers candid advice on following passion over prestige, understanding the differences between CFO and COO roles, and...
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10 Min CxO Clip- Casey Woo
CXO Conversations
In “Making the Hardest Call – Admitting it’s Not for You,” , former CFO forLanding.com, shares the pivotal moments that shaped his career journey—from starting at West Point and pivoting to Harvard, to walking away from Wall Street to pursue his passion for building and leading companies. With CFO and COO roles at firms including WeWork and Zozi, Casey reflects on following your own path instead of others’ expectations, the lessons he’s learned on his way to the C-suite, and why choosing finance allowed him to combine strategy with impact. His story is a powerful reminder...
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2 Min CxO Clip- John Oechsle
CXO Conversations
What does it take to plan a career all the way to the CEO chair? In this episode of CXO Conversations, John Oechsle discusses the strategic decisions that helped him rise from technology leadership at J&J and IHS to CEO of Derive Systems. He reflects on how international assignments shaped his leadership style, why embracing “crackpot projects” at Kellogg’s accelerated his growth, and the importance of taking roles for the right reasons—not just for compensation. For aspiring executives, John’s story is a roadmap on career planning, resilience, and the values that define strong...
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10 Min CxO Clip- John Oechsle
CXO Conversations
In “Career Planning and Strategic Decisions to Become CEO,” was CEO of Derive Systems and now Bolt On Technology, shares how purposeful choices shaped his path from CIO roles at Johnson & Johnson and IHS to leading multiple organizations, including Swiftpage and now Derive. John explains how he set a goal early to become a CEO, took on challenging assignments others avoided, and leveraged international experiences across Europe, Latin America, and Asia to expand his leadership perspective. He also offers candid insights on why money is the wrong reason to pursue the C-suite and why...
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2 Min CxO Clip- Craig Cummings
CXO Conversations
What does it take to transition from the battlefield to the boardroom? In this episode of CXO Conversations, Craig Cummings—Army veteran, Bronze Star recipient, and co-founder of Moonshots Capital—discusses the lessons he’s carried from 17 years of military service into the world of startups and venture capital. He shares practical advice on creating a career-defining elevator pitch, supporting veteran entrepreneurs, and building strong networks that accelerate growth. From deploying with Special Operations to scaling tech startups and investing in extraordinary leaders, Craig’s...
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10 Min CxO Clip- Craig Cummings
CXO Conversations
In “Building Your Career Transition Elevator Pitch,” shares how his journey from Army Intelligence Officer in Afghanistan to General Partner at Moonshots Capital shaped his approach to leadership, entrepreneurship, and investing. A Bronze Star recipient and West Point graduate with a Ph.D. from Columbia, Craig explains how veterans can craft an elevator pitch that opens doors, the importance of building strong entrepreneurship communities like Austin’s, and why investing in talented veteran founders is a mission for him. His story is a powerful reminder that clarity, curiosity, and...
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2 Min CxO Clip- Chris Younger
CXO Conversations
What can hundreds of transactions and decades of leadership teach us about CEOs? In this episode of CXO Conversations, Chris Younger, CEO of Class VI Partners, reflects on buying, selling, and leading companies across industries. He shares candid insights on managing the stress of leadership, why presence and transparency matter, and how servant leadership builds lasting teams. From his experience acquiring 27 companies to guiding CEOs through exits and growth strategies, Chris highlights both the rewards and the realities of C-suite life—and why prioritizing self-care is as important as...
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10 Min CxO Clip- Chris Younger
CXO Conversations
In “CEO Insights & Self Care with Chris Younger,” shares lessons from a career spanning telecom, private equity, and advisory leadership. As President of Expanets, he acquired 27 companies in just 3 years before selling to Avaya, and today, as CEO of Class VI Partners, he advises middle-market businesses and family offices on transactions and growth. Chris opens up about the physical toll of overwork, the importance of managing stress, and why diet, sleep, and exercise are critical for executives. He also explains his “Dinner Test” for CEOs and why executive presence sets the tone...
info_outlineBill Wosilius joins the show to discuss matters ranging from declaring your role and how to obtain it, assessing the situation and making hard executive changes, why become a CEO, and how to prepare for it. He has a wealth of advice to share and the experience to back it up; don’t miss this episode.
ABOUT OUR GUEST
After graduating from the U.S. Airforce Academy and serving for eight years, Bill worked for companies such as InFlow, Sunguard, Healthgrades, CoreSite, Optiv, and now NexusTek.
GET IN TOUCH WITH BILL WOSILIUS ON LINKEDIN
THANKS TO OUR SPONSORS
Podfly Productions: Podfly.net
Veterans of Foreign Wars: VFWpost1.org
OC Executive Search: OCExecutiveSearch.com
KEY TAKEAWAYS
[1:52] Michael introduces Bill and asks him to share an interesting tidbit about himself — Bill made a promise to himself that he would run one adventure race a year, every year until he couldn’t.
Bill talks about what NexusTek does and who they are.
ACCIDENTAL CEO [5:55] Bill shares how he came to be a CEO at NexusTek, and shares a few pieces of advice for reaching the C-suite, including avoiding target fixation!
ALL OF IT IS IMPORTANT [9:35] Looking back on what led him to where he is today, Bill shares that every single experience in the last 10 years has contributed to him being an accidental CEO and IT guy.
FIVE FROGS [12:24] Bill shares the story of how he led his first integration and what cascaded from it, including the challenges of merging and integrating the Hatfields and the McCoys!
M&A BACK OFFICE [19:02] Although he wasn’t directly responsible for the back-office functions, Bill did get a chance to see how an M&A affects them. He touches on how important it is to hire strong, competent leaders for each of the functions.
NEWLY MINTED CEO [21:36] Bill describes his first 30, 60, and 120 days at NexusTek. He shares the first four questions he asks:
- What’s working?
- What’s not working?
- What should we start now?
- What should we stop now?
H.A.C. G.A.S. N.A. [24:54] Bill breaks down the acronyms he used to keep himself on track in choosing a team.
HUGE CHESS MOVES [27:36] Within his first 120 days, Bill had brought in — among others — a new CFO, COO, VP of Professional Services and a VP of Integration; he speaks to those decisions.
MANAGEMENT STYLE [30:22] Bill describes his management style, which he’s been both praised and criticized for!
ADVICE FOR ASPIRING CXO’s [32:32] Quit focusing on it! Just do a good job — the best job you ever had is the one you have right now.
HIRING EXECUTIVES [38:34] Bill shares the qualities he looks for when hiring for executive positions. He shares the use of the FORMS acronym.
FINAL THOUGHTS AND RECOMMENDATIONS [44:38] Bill shares his final advice: every job prepares you in some way; all of them are important. Michael shares his best worst job for the first time!
BEST WORST JOB BILL EVER HAD [46:52] All of them were good: except two where he worked for authoritative micro-managers.
Michael shares his own best worst job for the first time!
MORE FINAL THOUGHTS (as the music plays Bill off the stage!) [49:18] Bill has more invaluable advice to offer.
[50:35] Michael thanks Bill for coming on the podcast to share his insight and closes out the podcast with his favorite takeaways.
We hope you learned something today and enjoyed the conversation. Please give us 5 stars on iTunes and share your comments so we can improve and ask the questions you want to hear.
MENTIONED IN THIS EPISODE
Five Frogs on a Log: A CEO's Field Guide to Accelerating the Transition in Mergers, Acquisitions & Gut Wrenching Change, by Mark L Feldman and Michael F. Spratt
Extreme Ownership: How U.S. Navy SEALs Lead and Win, by Jocko Willink and Lief Babin
Make Your Bed: Little Things That Can Change Your Life… And Maybe the World,
by Admiral William H. McRaven
SPECIAL THANKS TO