Leaders & Legacies

Jon Morris built Rise Interactive from a solo operation to one of the largest independent digital marketing agencies in the world, scaling it to nearly $40 million in revenue over 16 years. He started with prize money from the University of Chicago's New Venture Challenge in 2004 and rode the wave of digital advertising's explosive growth.

Today, Jon is the founder and CEO of The Fiscal Advocate, where he serves as a fractional CFO for professional service firms. In this episode, Jon shares his "double wind" framework - the idea that success comes from having wind at your back in...

Pietro Canestrelli is a tax attorney and former IRS attorney who helps business owners and taxpayers protect their hard-earned money. As the founder of the Law Office of Pietro Canestrelli and author of America's Tax Defender, he focuses on getting the IRS out of your life as fast as possible.

In this episode, Pietro breaks down the three areas of tax work: compliance, proactive planning, and tax defense. He explains why being audited is actually a "badge of success," why CPAs don't do proactive tax planning, and shares underutilized strategies like R&D tax credits and cost...

In this episode of Leaders and Legacies, Craig Andrews sits down with Bernie DeSantis, CEO of Insignia Training Partners, to explore how leaders can transform virtual training from a dull obligation into a powerful leadership tool. Drawing on more than 20 years of experience in corporate learning and development, Bernie shares how organizations can deliver high-impact virtual experiences that engage people and drive real results.

Bernie explains why many virtual events fail: leaders treat them like in-person presentations and simply “turn on the camera.” But virtual environments demand a different approach. Leaders must intentionally create interaction, structure engagement, and...

Trust is often treated as a vague leadership ideal, but Kim Bohr argues it’s one of the most measurable and practical drivers of performance inside organizations.

As President and CEO of SparkEffect, Kim works with executive teams navigating disruption without breaking trust. In this conversation, she explains how leadership failures rarely come from malicious intent. Instead, they stem from blind spots—small behaviors, missed signals, and unexamined habits that slowly erode trust within teams.

Kim shares how leaders can recognize these “micro-moments” that shape trust every day. Whether it’s acknowledging mistakes quickly, demonstrating transparen...

In this episode of Leaders and Legacies, Craig Andrews sits down with Jeremy Fennema, founder of Fennema.io and a fractional CIO/CTO who helps growth-stage companies bring order to chaotic technology environments.

Jeremy explains why most companies struggle with technology—not because of poor tools, but because they lack strategy. Leaders often buy solutions to solve isolated problems, creating a patchwork of systems that don’t work together. Jeremy’s role is to step in, align technology decisions with business goals, and build a clear roadmap for execution.

He also breaks down the difference betwee...

Leadership often hinges on decisions made with incomplete information. In this episode of Leaders and Legacies, John C. Scott explains why strong leaders build financial clarity into their organizations rather than relying on intuition or a bank balance.

John, a CPA and partner at Anders, specializes in helping law firms understand the business side of their practice. Many attorneys excel in legal reasoning but never receive training in finance or firm management. That gap often leads to poor cash planning, uneven partner distributions, and missed opportunities to reinvest in growth.

John explains how law firms...

Nick Jain, co-founder of Eagle Rock CFO, believes leadership in the AI era comes down to leverage. The best leaders won’t be replaced by AI—they’ll use it to multiply their impact.

Nick explains how AI and smart automation are eliminating low-value work like data cleanup, financial modeling, and report creation. That shift frees leaders to focus on judgment, relationships, and strategic decisions. Instead of spending weeks analyzing spreadsheets, leaders can now generate insights in hours—and act faster than competitors.

He shares how AI can compress consulting-level analysis into a fraction of the time...

Sriram Mangudi believes leadership reveals itself in moments of pressure. In this episode, he shares hard-earned lessons from global HR leadership, M&A integrations, and navigating COVID while running essential pharmaceutical operations.

He explains why most leaders fail during transformation: they push agendas instead of listening. In one high-stakes acquisition, Sriram walked into a room filled with suspicion. Instead of forcing integration plans, he listened. That shift built trust, preserved value, and turned a tense acquisition into a long-term success.

Sriram breaks down what separates reactive managers from strategic leaders. Strong leaders create space for...

Erik Brenner doesn’t lead from theory. He leads from structure.

As President and CEO of Hilltop Wealth & Tax Solutions, Erik built a firm that integrates advanced tax strategy with wealth management. He saw what others missed: reactive advice was failing clients. CPAs focused on last year. Advisors focused on investments. No one owned the full picture.

So he changed it.

Erik shares how a defining client case exposed the cost of disconnected advice. Required minimum distributions were set to create a future tax crisis. The CPA didn’t see it. Erik did. That...

Leadership isn’t just vision. It’s responsibility. In this episode, Catrina M. Craft challenges business owners to rethink what leadership really means when it comes to money, decisions, and long-term impact.

Catrina explains why most entrepreneurs unknowingly overpay the IRS—not because the law requires it, but because they were never taught how the system actually works. She draws a sharp line between compliance and strategy, arguing that true leaders don’t just “file correctly,” they plan intentionally.

The discussion covers why relying solely on a CPA can limit growth, how leaders use the tax code as...

In this episode of Leaders and Legacies, Craig Andrews speaks with Brett Swarts, founder of Capital Gains Tax Solutions, about what leadership looks like when business owners think beyond today.

Brett makes the case that strong leaders plan for exits long before they happen. Most owners focus on growth, customers, and operations, but fail to prepare for the financial reality of selling. That lack of foresight can cost 20–50% of their wealth in capital gains taxes.

Brett explains why leadership is about optionality—building a business that can run without you, scale cleanly, and exit efficiently. He w...

Most leadership failures don’t start with people. They start with poor visibility into the business. In this episode, Heidi DeCoux explains why leaders who don’t understand their numbers end up working longer hours while making less money.

Heidi breaks down the leadership trap of chasing top-line revenue without understanding profitability. She explains why many founders scale chaos instead of results and how unclear financial data leads to bad decisions, burnout, and broken teams. Drawing from decades as a serial entrepreneur, she shows how leaders can use simple KPIs to identify what actually drives profit—and what q...

Leadership today demands more than vision and execution. It requires the ability to protect people, data, and trust in an increasingly hostile digital environment.

In this episode, Craig Andrews sits down with Robert Siciliano, a leading authority on identity theft, cybersecurity, and personal risk management. Robert breaks down why security is no longer an IT issue—it’s a leadership responsibility. He explains how leaders who ignore cyber and identity risks expose their teams, customers, and brands to avoidable damage.

Robert shares how strong leaders think proactively about risk, build security-aware cultures, and make prevention part...

Adam House doesn’t believe in waiting for the right moment—he builds momentum. In this episode of Leaders and Legacies, Adam shares how his “Why Not?” mindset propelled him from serial entrepreneur to professional basketball player at 32—and later, to becoming CEO and co-owner of the very team he joined.

Craig Andrews explores Adam’s leadership journey through seven ventures, including a healthcare analytics platform that went public. Adam reflects on the real value of failure, timing, and using outsider perspective as an advantage. His businesses span tech, marketing, supplements, roofing, and more—but his leadership playbook stays...

Jennifer Bookspan knows that leadership isn’t about filling seats—it’s about shaping the future of an organization. In this episode, she joins Craig Andrews to discuss how her firm, Bookspan Search Partners, goes beyond typical executive recruiting to help companies build intentional, aligned leadership teams.

Jennifer shares why the best leaders are usually the best listeners, and how humility, clarity, and vision all factor into successful hiring. She explains what most founders get wrong when searching for executive talent and how her team helps them avoid costly misfires.

From hard-earned lessons to practical hiring...

Greg Giniel, Professional EOS Implementer, joins Craig Andrews to break down the mindset shift every business owner must make: stop being the easy button for your team. In this candid conversation, Greg explains how the EOS framework builds leaders at every level, freeing business owners from the daily grind while increasing performance across the organization.

He shares personal stories, including how his team kept his business thriving while he was sidelined with COVID for a month. The reason? Clear systems, strong core values, and a culture that encourages decision-making and allows room for failure.

Greg...

Chris Brown, CTO of Wow Remote Teams, shares how Latin America became his go-to talent solution—and why more U.S. businesses should follow. After running a booming medical e-commerce operation during the pandemic, Chris needed scalable, affordable, and reliable help. His wife Julie, originally from Bogotá and now CEO of Wow Remote Teams, helped him build a nearshore workforce that outperformed U.S.-based teams at a fraction of the cost.

Chris breaks down the real-world benefits of remote hiring—language capabilities, time zone alignment, and deep professional talent. He also exposes the limits of AI in cu...

David Kreeger traded legal briefs for business breakthroughs. In this episode, the founder of GoPedal shares his journey from practicing law at WilmerHale and IBM to owning a painting franchise and now leading strategic transformations for companies that feel stuck.

David reveals what drew him away from the legal grind—a desire to make decisions, improve quality of life, and be present for his family. His pivot into entrepreneurship wasn’t just about freedom; it was about creating value where others saw commodity. One $1,700 job turned into $600,000 in revenue because he treated every customer like gold.

No...

Alex Langan blends law and finance to protect employees from the hidden traps inside their company retirement plans. As founder of Langan Financial Group and a practicing attorney, Alex has seen the worst—plans charging over 4% in fees with little to no service. In this episode, he explains how poor plan design and ignorance—not malice—often sabotage employee retirements. True leadership, he argues, means protecting your team from this kind of financial abuse.

Drawing from his upcoming book 401(k) Exposed, Alex reveals the legal shifts making it easier than ever to sue employers who fail their fiduci...

Mark Miller doesn’t just manage money—he manages legacies. As the managing partner of Hilton Wealth and co-leader of the Hilton family office, Mark helps business owners and high-net-worth individuals make smarter, safer financial decisions. In this episode, Mark breaks down the misunderstood world of family offices and how they function as a “general contractor” for wealth—coordinating top-tier advisors across tax, investments, legal, and insurance.

He explains how the average investor is often set up to fail, driven by emotion and overexposed to risk. The wealthy, on the other hand, take a safety-first approach—prioritizing protection o...

Ty Givens, founder and CEO of CX Collective, joins Craig Andrews to break down the overlooked power of customer experience. Ty argues that customer experience isn’t just about fixing problems—it’s about preventing them. Through real-world examples, from Starbucks to five-star restaurants, Ty highlights how small touches—like empathy and initiative—can turn a moment of friction into long-term loyalty.

She shares her early career misstep that changed everything: thinking she was just an employee instead of the brand itself. That shift in mindset launched a career helping brands—from startups to Fortune 500s—reshape how they engag...

Dr. Sherry Peel Jackson, former IRS agent turned tax strategist, pulls back the curtain on how small business owners are unfairly targeted by the system. In this hard-hitting episode, Sherry explains why the IRS considers entrepreneurs “low-hanging fruit” and how to legally protect yourself through strategic deductions and proper business structuring.

After leaving the IRS, Sherry discovered deep flaws in the tax system—ones that led to a federal prison sentence when she spoke out. But instead of backing down, she doubled down. Now, she helps six-figure professionals keep more of what they earn without crossing legal lines...

Nils Vinje helps CEOs scale by aligning their leadership teams. In this episode, he breaks down how misalignment at the top quietly drains momentum—and what to do about it. Drawing from his time in Silicon Valley, where leadership teams were swapped out like batteries, Nils explains why true alignment starts with shared understanding and ruthless simplicity.

Nils outlines the five principles that power every successful business: People, Purpose, Playbooks, Performance, and Profit. He argues that most dysfunction goes unnoticed because it feels normal from the inside. His job is to bring clarity—often by asking the ques...

James Elliman planned to be a Marine officer, following a family legacy of military service. But a last-minute medical disqualification forced a hard pivot. Instead of serving in uniform, he leaned into his lifelong love of tech and launched Elliman Technologies to simplify IT for small businesses.

In this episode, James shares how leadership isn't just about titles—it’s about clarity, adaptability, and serving others, even when plans fall apart. He opens up about the early days, charging $14 an hour and fixing printers via Facebook. Over time, he learned how to price value, not time, and tran...

Craig Andrews opens up about the most defining moment of his life—a six-week coma after a severe case of COVID-19. Doctors told his wife he wouldn’t survive. But he beat the odds. When he woke, he discovered that his team and community kept his business running. That, he says, is his proudest leadership moment.

In this solo episode, Craig reflects on the radical recovery process and the outrageous goals that powered his comeback. From being too weak to raise the blinds to showing up at a high-intensity workout in a wheelchair and on oxygen, Craig shar...

Craig Andrews opens up about the most defining leadership moment of his life—one he wasn’t even conscious for. After slipping into a six-week coma from COVID-19, doctors told his wife he wouldn’t survive. But his team kept the business running. Freelancers stepped in unasked. That’s when Craig knew he had built something more than a company—he built loyalty.

In this special Christmas episode, Craig reflects on that recovery period and the relationships that mattered most. From struggling to climb stairs to re-learning how to stand, he talks candidly about physical weakness and emotional...

Camille Diaz’s leadership story is rooted in reinvention. A science teacher turned ballroom dance studio co-founder, she built a thriving business—until a partner change derailed everything. Faced with debt, a lawsuit, and burnout, Camille hit rock bottom. But when friends began asking her for business advice, she discovered a new path: optimization coaching.

Camille now leads Serenity Financial, helping businesses and individuals create sustainable wealth through financial education and strategic benefits planning. Her leadership style is direct, process-driven, and focused on giving people tools to regain control of their lives. In this episode, she shares how...

Chris Mathew, Chief Growth Officer at Well-Genie, joins Craig Andrews to reveal how his father’s tragic and avoidable death shaped his mission to transform American healthcare. With deep family roots in Kerala and a legacy of firstborn leadership, Chris channels that sense of duty into helping employers radically cut costs while increasing wellness benefits for their teams.

Chris doesn’t just talk cost savings—he proves it. Well-Genie offers unlimited $0 generics, discounted brand-name drugs, and wellness programs that bypass traditional insurance models. The results? Employers cut healthcare spend by up to 50% while improving retention with life-enhancing benefi...

Ely Delaney doesn’t just teach follow-up marketing—he lives it. On this episode of Leaders & Legacies, Ely shares how authenticity and consistency transformed his business and leadership style. From his signature purple branding to a three-year evergreen email campaign, Ely leans into what makes him different—and encourages others to do the same.

He and host Craig Andrews explore the leadership lesson behind showing up as your full self, even when it’s unconventional. Ely discusses how revealing his personal quirks, like his Renaissance fair obsession and dog love, helped him build stronger business relationships. The real lea...

Kimberly Carleson didn’t set out to become a leader in health care reform. Life forced her into it.

When her husband was diagnosed with stage four metastatic bladder cancer, Kimberly found herself navigating a health care system built for confusion, not care. Pregnant and raising a young daughter, she refused to accept the death sentence doctors gave her husband. Her advocacy, persistence, and leadership saved his life—and revealed a deeper calling.

That experience became the foundation for U.S. Beacon, the company she founded to fight bloated medical billing and protect employers from skyr...

DeeAnn Palin doesn’t just fix companies — she rebuilds them from the inside out. In this episode, Craig Andrews talks with the founder and CEO of OnPoint Business Solutions about her radical journey from corporate HR skeptic to trusted strategic partner for CEOs.

Palin pulls back the curtain on toxic culture, ethical blind spots, and the cost of keeping the wrong people in leadership. She explains why HR should never be treated as a compliance function — and how, when done right, it becomes a company’s growth engine.

Drawing from her experience with brands like Motorola...

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 l...

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 sto...

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 bu...

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.

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...

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: inve...

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 und...

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...

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...