We are thrilled to welcome rockstar business coach Bill Gallagher, the founder of Scaling Coach, as our guest.
Bill has dedicated his career to helping entrepreneurs organize their lives, refine their leadership skills, and elevate their performance. He joins us today to share his journey, insights, and the story behind his impressive startup success.
Tune in to learn the strategies that have helped countless leaders scale with confidence, clarity, and purpose!
A Coach and Leader
Bill has spent over 13 years coaching companies globally, often through EO and EO Accelerator programs. He excels at planning, delivering value to clients, and creating content, but is not strong in sales or lead generation, so he has always relied on referrals and relationships. His deep involvement in AI keeps him current and curious. Despite not being in the ultra-wealthy crowd, Bill measures his success by the lives he has touched, the quality of his work, and the legacy he builds daily.
Using AI as a Daily Business Tool
Bill uses AI to enhance his efficiency and creativity, but not to replace human interaction or strategic judgment. He finds it most effective as a thinking partner, to support his ideation, drafting, and refinement, rather than something to hand over the reins to. He explains that AI can help build a first draft of an event plan or workshop structure, but a real coach or planner still needs to bring the nuance, customization, and connection.
Designing Events Around Outcomes
Events are not just about logistics, but about strategy. Event planners need to understand why the event is happening, what the client wants the attendees to experience, and how their success will be measured, as that informs every choice. For Bill, events are all about building memorable, emotionally resonant experiences that connect to the bigger picture and feel locally relevant and human. From the initial walkthrough to the final takeaway, every element should serve the outcome.
Types of Engagements
Business growth events fall into three categories: one-off workshops, multi-session programs like accelerators or university partnerships, and ongoing quarterly strategy meetings with clients. Each requires different prep and different energy. One-offs aim to create momentum or a spark that leads to change. Series-based programs get built over time. Recurring client sessions require both routine (quarterly review and planning) and creativity (changing formats to stay relevant and engaging).
Team and Time Management
Bill runs his business with a lean team of six- two employees and four consistent contractors. Most of his clients come through referrals, which makes relationships essential. He discovered that cold outreach to CEOs rarely works, so he focuses on deepening value for current clients and relying on word of mouth. Even though his work spans the globe and has been well-established, his goal has never been to amass outrageous wealth but to build a sustainable career with meaningful impact.
Defining Enough
Bill believes that financial success is relative. It is easy to get caught in comparison, especially when surrounded by people chasing billions. But having a great career, a decent income, and a life filled with impact can be more than enough. A message from a former client expressing gratitude years later served as a reminder that influence often happens quietly, and we usually have more impact than we realize.
Rethinking Growth
Not every company has to scale. Many business owners hit their ideal income range and stay there. Even though that is valid, Bill urges business owners not to believe that avoiding growth will spare them from stress. He explains that whether your business is small or huge, you will still wake up in the middle of the night thinking about it. Growth does not always mean going public or raising funds. It may mean improving systems, empowering people, or building something more resilient and enjoyable.
Stress Is Part of the Journey
Stress does not scale down with the size of your business. So, whether you are responsible for $1 million or $500 million, the emotional weight is real. What truly matters is delegating, empowering your team, and not trying to carry it all alone. Bill emphasizes that the CEO of a billion-dollar company has the same amount of time as you, but they have learned to delegate effectively. To scale successfully, you must stop micromanaging, avoid constant firefighting, and begin empowering the team you hired to drive growth.
Impact and Legacy
The legacy of your work lies not just in what you build, but in how you lead, who you influence, and what people remember. Just as personal mentors leave behind values, humor, or a sense of adventure, your leadership will leave a lasting imprint. So, even if your business does not sell for millions, it gives you a life and something to leave behind. That is what truly matters.
Nothing Lasts Forever
Every business has a life cycle. Even giants like Yahoo, AOL, and GE were once dominant before they faded. That is truly a failure, however. It is reality. So, build something as big as it can be, for as long as it can be. But do not cling to the idea that it has to be permanent. Remember, the measure of success is not how long something lasts but what it does while it is here.
Bio: Bill Gallagher
Bill Gallagher is a highly rated business coach whose passion is helping CEOs and entrepreneurs manage growth more effectively, restore order and sanity to their lives, and achieve greater growth or faster growth. With over 40 years of entrepreneurial and executive experience and 20 years of coaching and training leaders seeking to enhance their leadership and performance, he now works with leaders and teams in more than 31 cities across 15 countries. He has led four companies as CEO/owner and was a partner/executive in two others as they grew from startup to more than $550 million in annual revenue.
A former DJ and radio executive, Bill hosts the Scaling Up Podcast. In his free time, he is an avid surfer, sailor, skateboarder, pilot, scuba enthusiast, and recovering triathlete. Happily married for 30 years, he and his wife, Lori, live in the Oakland Hills and are parents to two very successful young adult entrepreneurs.
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Email: Bill@scalingcoach.com
