Ashley Connell, CEO of Prowess Project, joins Leaders and Legacies to unpack a bold truth: leaders don’t need another version of themselves. They need a “not you”—a skilled operator who thrives on structure, details, and execution.

In this episode, Ashley shares how she built a talent pipeline of highly qualified caregivers—primarily mothers and sandwich-generation women—who bring unmatched emotional intelligence and professional rigor to operations roles. These women aren’t looking for handouts; they’re looking for impact and flexibility. And they deliver, often increasing profits, improving team dynamics, and freeing CEOs to focus on growth.

Ashley and Craig explore how emotional intelligence should be compensated like hard skills, why leadership means letting go, and the power of empathy in business. Ashley also reveals how Prowess Project uses data—not gut instinct—to match CEOs with the right operators, transforming overwhelmed founders into confident leaders.

This is a must-listen for any business owner ready to lead with intention and build a legacy of empowered teams.

Want to learn more about Ashley Connell's work? Check out their website at https://www.prowessproject.com.

Connect with Ashley Connell on LinkedIn at https://www.linkedin.com/in/ashley-connell-ceo/.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Milam Miller, founder of Be Confident and Kind and author of The Charisma Craft, joins Craig Andrews to challenge everything we think we know about charisma. A former executive for a billionaire sports team owner and affectionately nicknamed the “real-life Ted Lasso,” Milam shares how charisma isn’t innate—it’s a skill any leader can develop.

Through bold stories and sharp insight, Milam breaks down his ABCs of Charisma: Authenticity, Boldness, and Curiosity. He reveals how top leaders like Jack Welch and Sam Walton mastered connection through confidence and kindness—not through dominance or ego. Whether it’s helping sales teams outperform AI or guiding executives to connect instead of command, Milam’s approach is rooted in relational leadership, not transactional tactics.

This episode is packed with practical tools for modern leaders who want to elevate influence, build trust, and create high-performing teams that thrive on human connection.

Want to learn more about Milam Miller's work? Check out their website at https://beconfidentandkind.com.

Connect with Milam Miller on LinkedIn at https://www.linkedin.com/in/milam-miller-bck.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Justin Dixon walked away from a comfortable six-figure job and launched a recruiting firm—just weeks before the world shut down. In this episode, he joins Craig Andrews to unpack what it really takes to lead when the timing couldn’t be worse.

Justin shares the personal finance moves he and his wife made to de-risk the leap, and why reading Rich Dad Poor Dad flipped his entire outlook on life and career. He talks about navigating COVID as a new business owner, giving away free career advice when no one was hiring, and how that generosity paid off later.

He also dives into how most business owners misunderstand recruiters—and the small moves that can drastically improve your odds of landing A-players. From running triathlons to running a company, Justin reveals the parallels between endurance sports and entrepreneurial grit.

Want to learn more about Justin Dixon's work? Check out their website at https://www.hiretomorrow.com.

Connect with Justin Dixon on LinkedIn at https://www.linkedin.com/in/jmdixon15/.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Sonny Grappone didn’t follow a straight path to success. Raised by a single mother from Guyana and a hardworking Italian-American stepfather, Sonny grew up in Queens, New York, sharing a bed with his mom and sister. That early scarcity drove his work ethic—bagging groceries at 12, building computers in high school, and running an auto detailing business in college.

At 25, he pivoted. He went back to school, discovered a knack for accounting, and never looked back. After years in the corporate grind, Sonny bet on himself and launched Precision Accounting & Consulting. His leadership mindset is clear: invest in yourself, know your value, and make bold decisions—even when they seem risky.

He now advises law firms, construction companies, and business owners on how to treat accounting as an investment, not an expense. Sonny doesn’t just run numbers—he helps clients fund growth, make strategic hires, and unlock hidden savings with federal tax programs.

His leadership mantra? “Scared money doesn’t make money.”

Want to learn more about Sonny Grappone's work? Check out his website at

https://precisionaccountingconsulting.com

Connect with Sonny Grappone on LinkedIn at

https://www.linkedin.com/in/sonny-grappone-24536312a

Think you'd be a great guest on the show? Apply at

https://podcast.allies4me.com/podcast-guest/

Want to learn more about Craig Andrews’ work at allies4me? Visit

https://allies4me.com/

Justin Jasniewski, CEO of Serve You Rx, breaks down one of healthcare’s murkiest corners—pharmacy benefit managers (PBMs). In this episode, he exposes how PBMs sit at the crossroads of drug manufacturers, employers, and pharmacies—often inflating costs instead of controlling them. With plain talk and sharp insights, Justin walks through how the system evolved from a simple IT add-on to a high-stakes financial engine that can either serve or exploit employers.

He highlights the fiduciary responsibilities employers often overlook and the lawsuits now surfacing when health plan mismanagement drains employee benefits. Justin stresses the importance of understanding what your PBM is really doing with your money and lays out how transparency and better contracts can unlock serious cost savings—sometimes enough to fund new hires or expansion without touching top-line revenue.

This episode is a wake-up call for business leaders: your PBM could be silently bleeding your budget. The good news? You can fix it—and Justin shows you how.

Want to learn more about Justin Jasniewski's work? Check out their website at https://ServeYouRx.com.

Connect with Justin Jasniewski on LinkedIn at https://www.linkedin.com/in/justin-jasniewski/.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Eli Portnoy, CEO and co-founder of BackEngine, joins Craig Andrews to expose the flaws in traditional customer feedback systems—and why leadership demands better data. A seasoned entrepreneur and Harvard Business School Executive Fellow, Eli dives into how B2B companies often make strategic decisions using flawed insights from biased surveys.

Eli unpacks how leadership in the AI era means throwing out broken instruments like opinion surveys and adopting tools that capture real, unfiltered customer conversations. He explains how BackEngine uses large language models to surface actionable feedback from client interactions—email threads, Zoom calls, and more—giving leaders a fuller, more accurate picture.

His leadership philosophy? You can’t solve the right problems if you’re asking the wrong questions. Eli makes a compelling case for empowering decision-makers with authentic customer sentiment—without the distortion of surveys or false memories.

Want to learn more about Eli Portnoy's work? Check out their website at https://backengine.ai.

Connect with Eli Portnoy on LinkedIn at https://www.linkedin.com/in/eliportnoy/.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Donovan Pyle pulls back the curtain on an industry most business leaders misunderstand: employer-sponsored health care. In this episode, Donovan explains how companies are overpaying by as much as 25%—often without realizing it—and why the current broker model keeps them trapped. Drawing on his own experience inside a major insurance company and later as a broker, Donovan saw firsthand how incentives are misaligned and how brokers are often rewarded for selling the most expensive plans—not the best ones.

That realization got him fired… and fired up. He launched Health Compass Consulting to give employers a path out. Donovan outlines how business leaders can cut costs without slashing benefits. In fact, the key to savings is often improving employee care, not reducing it.

This conversation is a must-listen for CFOs, HR leaders, and CEOs who want to transform their benefits from a financial liability into a strategic advantage.

Want to learn more about Donovan Pyle's work? Check out their website at https://www.donovanpyle.com.

Connect with Donovan Pyle on LinkedIn at https://linkedin.com/in/donovanpyle.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

William Bissett, founder of Portus Wealth Advisors, joins Craig Andrews to unpack what it really takes to lead a company that survives and thrives beyond its founder. William shares how watching his father struggle in solo practice shaped his commitment to team building. His insight is simple but powerful: don’t just hire talent—hire people who fill your gaps, not mirror them.

The episode cuts through leadership myths and focuses on what makes businesses last—trust, delegation, and the willingness to let go. William shares his approach to building high-performance teams using tools like the Culture Index, but emphasizes that real success comes from empowering people to grow—even if that means they eventually leave.

For William, leadership isn’t about control—it’s about legacy. That means creating wins for your people, investing in their growth, and building a culture that celebrates progress. It’s leadership with humility and a long view.

Want to learn more about William Bissett's work? Check out their website at http://www.portusadvisors.com.

Connect with William Bissett on LinkedIn at https://www.linkedin.com/in/williambissett/.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.