Shows / Leaders & Legacies
Leaders & Legacies
The Leaders & Legacies Podcast celebrates leaders who are making a difference beyond themselves. It was inspired from events in 2021 when the host, Craig Andrews went into a 6-week coma. Even after waking up, his brain was scrambled for another two weeks. When his mind cleared, his wife started telling him how his team stepped up and ran the company without him. Freelancers reached out to his team and offered to do whatever was necessary while he was in the hospital. Craig believes we all make…
Episodes
- Leaders & Legacies
297 - Ask Before You Answer: The Client-Trust Habit with Scott Armstrong
Scott Armstrong grew Brainrider to $22 million without making a profit, then rebuilt it as a $4.6 million agency with a 13% margin. That painful contrast…
- Leaders & Legacies
296 - Motivation Fades. Commitment Carries You Through with John Ulsh
A routine drive home from his daughter’s swim meet changed John Ulsh’s life in seconds. After a head-on collision with a combined impact speed of 125 miles per…
- Leaders & Legacies
295 - Your Packed Calendar Is a Scaling Warning with Nathan Parkhouse
A founder’s constant availability can feel like exceptional service, but it can quietly make the entire business dependent on one person. When every client…
- Leaders & Legacies
294 - Why “We Screwed Up” Can Be the Start of Greater Trust with Craig Andrews
Many leaders fear that admitting a miss will destroy a client relationship. Craig Andrews argues that delaying the truth is often far more damaging. Delivering…
- Leaders & Legacies
293 - Why Your CPA and Tax Lawyer Play Different Roles with Josh Lowenthal
Business owners face a costly tension when planning an eventual exit: the decisions that may shape taxes and deal outcomes often need attention years before a…
- Leaders & Legacies
292 - Why Growing Revenue Won’t Fix a Profitability Problem with Arron Bennett
Revenue can climb while cash gets tighter, margins shrink, and the owner ends up working harder for less. Arron Bennett explains why trying to outgrow a…
- Leaders & Legacies
291 - How Marketing Cuts Can Damage Business Value with Craig Andrews
When business gets tight, marketing often becomes one of the first expenses on the chopping block. Craig Andrews opens with the contrast at the heart of that…
- Leaders & Legacies
290 - The Live Oak Lesson: Authenticity in the Age of AI with Craig Andrews
AI can make work faster, cheaper, and more efficient. But when leaders start handing AI the parts of the business that require trust, empathy, and human…
- Leaders & Legacies
289 - What Business Owners Should Fix Before the Buyer Shows Up with Adam Marshall
Business owners often treat legal work like a fire alarm: wait until something starts burning, then call for help. Adam Marshall, Managing Member at Lorium…
- Leaders & Legacies
288 - Five Stars or Nothing: Scaling Through Service with Paul H. Graham
The hard part of scaling is not always strategy, capital, or market timing. Sometimes the constraint is the owner's grip. Paul Graham joins Craig Andrews to…
- Leaders & Legacies
287 - Systems Don't Fail. Standards Do with Richard Walsh
A business can install the right system, build the right dashboards, and still bleed profit because nobody is holding the standard. Richard Walsh returns to…
- Leaders & Legacies
286 - Built From the Customer Backward with Sheldon Wolf
Real estate customers now do much of the work that once justified the old brokerage model. They find the house, research neighborhoods, compare mortgage…
- Leaders & Legacies
285 - Why Product-First Selling Breaks High-Trust Pipeline with Steve Wallace
Too many leaders say they sell through relationships, then walk into the next discovery call and make the product the center of the room. The result is a…
- Leaders & Legacies
284 - Build Your Brand and Media Presence with Ted Jenkin
Most leaders say they want a stronger brand, but many still judge every decision by this quarter’s direct ROI. That tension runs through Craig’s conversation…
- Leaders & Legacies
283 - Financial Clarity, Operating Discipline, and the Business That Runs Without You
Too many business owners build companies that depend on them for every important decision, every customer save, every operational fix, and every financial…
- Leaders & Legacies
282 - The CFO Who Helps You Say Yes with Fred Kosnac
Revenue can make a business owner feel like the company is winning, even while cash, margin, and operational drag are quietly telling a different story. In…
- Leaders & Legacies
281 - Your Best AI Strategy May Already Be Inside Your Business with Stephan Bajaio
AI has made search feel new again, but Stephan Bajaio warns leaders not to mistake new acronyms for a new strategy. Whether people call it SEO, AEO, GEO, or AI…
- Leaders & Legacies
280 - Private-Equity-Grade Finance for Owner-Led Companies with Salvatore Tirabassi
Most business owners do not need prettier dashboards. They need financial reporting that helps them make better decisions, faster. In this episode of Leaders &…
- Leaders & Legacies
279 - Stop Treating Your Business Lawyer Like a Vending Machine with Matt Bracy
Matt Bracy helps business owners make better legal decisions before those decisions become expensive problems. As a partner at Scheef & Stone, former…
- Leaders & Legacies
278: Scaling Without Breaking the Business with Gary Leeman
Gary Leeman helps leadership teams break through the ceilings that stall growth. As a Professional EOS Implementer with EOS Worldwide and a former integrator…
- Leaders & Legacies
277: The Legal Advice Business Owners Actually Need with Aron Phillips
Aron Phillips is an attorney and founder of the Law Office of Aron Phillips in the Stockyards of Fort Worth, where he advises business owners on entity…
- Leaders & Legacies
276: The Human Intelligence Behind Scaling Your Business with Courtney DeRonde
Courtney DeRonde is the CEO of Forge Financial and Management Consulting and creator of the Simple Scale Up System, a framework built to help…
- Leaders & Legacies
275 - Why Too Much Software Is Killing Your Margins with Chad King
Chad King helps businesses stop bending themselves around rigid software. Today, as VP at Ayoka Systems, he focuses on automation, integration, and custom…
- Leaders & Legacies
274 - From Kyiv to the Boardroom - Bob Nienaber on Retaining Top Talent
Bob Nienaber has spent more than three decades helping companies design executive benefit plans that retain top talent and strengthen long-term business value…
- Leaders & Legacies
273 - Building Businesses That Last: Operational Excellence with Jake Isaacs
Jake Isaacs is a serial integrator and co-founder of Gathering the Kings, an entrepreneurial mastermind and coaching group. As a champion of operational…
- Leaders & Legacies
272 - Why US Manufacturing Can Still Compete Globally with David Solomon
David Solomon built and ran a $100 million toy manufacturing company in the 1990s with 840,000 square feet of facilities in Montreal and Plattsburgh, New York…
- Leaders & Legacies
271 - The "Double Wind" Strategy: How to Pick Industries and Clients that Fuel Growth with Jon Morris
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…
- Leaders & Legacies
270 - America's Tax Defender: How to Fight the IRS and Win with Pietro Canestrelli
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…
- Leaders & Legacies
269 - Why Most Virtual Training Fails - and How Great Leaders Fix It with Bernie DeSantis
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…
- Leaders & Legacies
268 - The Micro-Moments That Build - or Break - Trust in Leadership with Kim Bohr
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…
- Leaders & Legacies
267 - The Strategic CIO: How Leaders Turn Technology Into a Growth Engine with Jeremy Fennema
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…
- Leaders & Legacies
266 - Financial Leadership for Law Firms: Turning Numbers into Strategy with John Scott
Leadership often hinges on decisions made with incomplete information. In this episode of Leaders and Legacies, John C. Scott explains why strong leaders build…
- Leaders & Legacies
265 - AI-Driven Leadership: How Smart Operators 10x Their Impact with Nick Jain
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…
- Leaders & Legacies
264 - From Conflict to Cohesion - Turning Strong Personalities into Strong Teams with Sriram Mangudi
Sriram Mangudi believes leadership reveals itself in moments of pressure. In this episode, he shares hard-earned lessons from global HR leadership, M&A…
- Leaders & Legacies
263 - Building a Firm That Outlives You - Erik Brenner on Leadership Through Integration
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…
- Leaders & Legacies
262 - Why Smart Leaders Don’t Outsource Thinking to Their CPA
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…
- Leaders & Legacies
261 - Leadership Means Planning the Exit Before You Need It with Brett Swarts
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…
- Leaders & Legacies
260 - Heidi DeCoux on Leadership, Cash Flow, and Why Most Businesses Fly Blind
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…
- Leaders & Legacies
259 - Why Modern Leaders Must Think Like Security Experts with Robert Siciliano
Leadership today demands more than vision and execution. It requires the ability to protect people, data, and trust in an increasingly hostile digital…
- Leaders & Legacies
258 - From Startups to Slam Dunks - Adam House on Leading with Grit and Vision
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…
- Leaders & Legacies
257 - The Hidden Cost of Bad Hires - and How to Avoid Them with Jennifer Bookspan
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…
- Leaders & Legacies
256 - Why Your Business Won’t Scale Until You Stop Solving Every Problem
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…
- Leaders & Legacies
255 - The Real Cost of Talent and the Hidden Goldmine in Latin America with Chris Brown
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…
- Leaders & Legacies
254 - The Power of Asking Better Questions with David Kreeger
David Kreeger traded legal briefs for business breakthroughs. In this episode, the founder of GoPedal shares his journey from practicing law at WilmerHale and…
- Leaders & Legacies
253 - The Hidden Dangers Lurking in Your 401(k) Plan with Alex Langan
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…
- Leaders & Legacies
252 - Inside the Hilton Family Office - Mark Miller on Leading with Clarity and Purpose
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…
- Leaders & Legacies
251 - The Hidden ROI of Kindness in Business - A CX Masterclass with Ty Givens
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…
- Leaders & Legacies
250 - The IRS Calls You 'Low-Hanging Fruit' - Sherry Peel Jackson Says Not Anymore
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…
- Leaders & Legacies
249 - The Power of Alignment - How Leadership Teams Accelerate Growth with Nils Vinje
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…
- Leaders & Legacies
248 - Why Simplicity Wins - James Elliman’s Blueprint for Small Business IT Leadership
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…
- Leaders & Legacies
247 - From ICU to Camp Gladiator - Setting and Achieving Outrageous Goals with Craig Andrews
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…
- Leaders & Legacies
246 - Choosing the Right Relationships - A Leader’s Priority with Craig Andrews
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…
- Leaders & Legacies
245 - From Ballroom to Boardroom - Camille Diaz on Leading Through Reinvention
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…
- Leaders & Legacies
244 - Reclaiming the American Dream Through Smarter Health Benefits with Chris Mathew.mp3
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…
- Leaders & Legacies
243 - From Purple Branding to Powerful Follow-Up: Ely Delaney’s Playbook
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…
- Leaders & Legacies
242 - Leadership Born in the ICU - Kimberly Carleson’s Mission to Fix Health Care Billing
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…
- Leaders & Legacies
241 - From HR Hater to Growth Strategist - DeeAnn Palin’s Bold Pivot
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…
- Leaders & Legacies
240 - From Marine to Media Mogul - Jesse Sieff on Leading with Precision
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…
- Leaders & Legacies
239 - The Power of Presence - Why Fathers Matter More Than Ever with Marquess Dennis
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…
- Leaders & Legacies
238 -Why Your CPA Isn’t Your Tax Strategist - And What to Do About It with Paden Squires
Paden Squires grew up in rural Missouri with firsthand experience of financial insecurity. That early exposure shaped his mission: help entrepreneurs grow…