Jesse Sieff is no stranger to reinvention. From military barracks to media production, he’s built a career on sharp pivots and sharper leadership. In this episode, Jesse breaks down how his time in the Marine Corps Drum & Bugle Corps instilled in him a deep respect for discipline, detail, and public representation—skills that now fuel his work at Sieff Studios.

Jesse’s leadership style blends strategic vision with creative execution. His studio isn’t just about producing polished videos—it’s about crafting media that moves people and delivers results. He shares how his military background helped him lead high-performing teams and why leaders should master the art of storytelling if they want to build trust and drive action.

Listeners get a behind-the-scenes look at how Jesse helps clients show up confidently on camera and how he integrates AI tools to strengthen internal communication and branding. Whether you're a business owner navigating change or a leader scaling your message, Jesse offers actionable insight on building systems that support clarity, confidence, and growth.

Want to learn more about Jesse Sieff's work? Check out their website at https://www.sieffstudios.com.

Connect with Jesse Sieff on LinkedIn at https://www.linkedin.com/in/jessesieff/.

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/.

Marquess Dennis doesn’t just talk about fatherhood—he’s on a mission to redefine it. As the founder of Birthright Living Legacy, he joins Craig Andrews to challenge cultural narratives, unpack generational trauma, and spotlight the deep systemic impact of absent fathers. Dennis shares his own journey from poverty in North Tulsa to building a nonprofit dedicated to helping fathers of all backgrounds reclaim their influence.

With unfiltered honesty, he discusses how fatherlessness isn't confined to any one race or class—“it affects the poor house all the way to the White House.” He weaves together personal stories, sobering statistics, and sharp social commentary, revealing how pop culture has eroded the public perception of fatherhood and how leadership begins at home.

Dennis makes a compelling case: fatherhood isn’t a footnote in a child’s life—it’s the framework. He urges dads to treat their families like million-dollar clients: full attention, consistent engagement, and intentional presence.

Want to learn more about Marquess Dennis's work? Check out their website at https://brlivinglegacy.com.

Connect with Marquess Dennis on LinkedIn at https://www.linkedin.com/in/marquessdennis/.

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/.

Paden Squires grew up in rural Missouri with firsthand experience of financial insecurity. That early exposure shaped his mission: help entrepreneurs grow wealth with clarity and confidence. In this episode, Paden breaks down why relying on your CPA for tax strategy is a mistake. Most CPAs are set up to file returns—not proactively plan.

He walks through high-impact tax strategies like the Augusta Rule and explains why business owners should think of tax strategy the same way they think about advertising: as an ROI tool, not an expense. With deep insight into entrepreneurial finance, Paden emphasizes building advisory relationships that prioritize long-term planning over reactive compliance.

He also sheds light on why so many accountants undervalue their work, run generic firms, and fail to deliver real value to business owners. If you’re running a 7-figure business and feel like you're leaving money on the table, this episode is your wake-up call.

Want to learn more about Paden Squires' work? Check out their website at https://www.squirestaxplanning.com/

Connect with Paden Squires on LinkedIn at https://www.linkedin.com/in/paden-squires-cpa-cfp-19681a1a/

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/

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/.

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/.

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/.