Leaders & Legacies

Hosted by Craig Andrews

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Episodes

277

Latest episode

Jun 2026

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About the show

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 an impact greater than we realize and wants to honor owners and founders as they lead others. Craig Andrews is the founder and Principal Ally at allies4me. He’s been in the marketing space for more than two decades and has driven over a half-billion dollars of revenue. He’s spoken on dozens of podcast as well as conferences including Conversion Conference.

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60 recent

June 11, 202632 min

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 formation, mergers and acquisitions, and commercial real estate. From a century-old building overlooking the daily cattle drive, Aron brings a practical legal perspective shaped by business realities rather than courtroom theatrics.In this episode, Aron explains what business owners should look for when they need legal help, where layered LLC structures can actually make sense, and why the right attorney fit matters as much as legal horsepower. He also shares how he approaches high-stakes deals with patience, trust, and finesse instead of force, and why preserving a client's autonomy often leads to better outcomes than trying to bulldoze a negotiation.Want to learn more about Aron Phillips's work? Check out his website at http://aphillipslawoffice.com.Connect with Aron Phillips on LinkedIn at https://www.linkedin.com/in/aron-r-phillips-47222b91/.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? Check out his website at https://allies4me.com/.

June 4, 202636 min

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 already-successful businesses navigate the complexity that growth creates. A CPA by training and an operator shaped by hard leadership lessons, she now helps founders and leadership teams scale both the business and the leader behind it.In this episode, Courtney shares what happens when growth creates a level of complexity that old habits can no longer handle. She walks through a painful leadership failure that nearly pushed her out of the business, the 18-month process she used to rebuild trust with her partners, and the human-centered philosophy that now drives her consulting work. Courtney also explains why scaling requires transformation in both the company and the leader, why strategic work needs dedicated space instead of leftovers, and how her Planning to Scale process helps leaders narrow focus and clear a path to growth.Want to learn more about Courtney DeRonde's work? Check out her website at https://planningtoscalebook.com.Connect with Courtney DeRonde on LinkedIn at https://www.linkedin.com/in/courtneyderonde/.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? Check out his website at https://allies4me.com/.

May 28, 202635 min

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 software strategies that make operations simpler, faster, and more profitable.In this episode, Chad breaks down why so many companies are trapped between overpriced off-the-shelf tools and expensive full-custom builds. He explains how AI is changing software development, why tech debt quietly drags down business performance, and what leaders should watch before trusting agents to build mission-critical systems on their own. Chad also shares how his team evaluates whether software should be replaced, integrated, or rebuilt, and why the real goal is not more software but better financial performance and fewer things falling through the cracks.Want to learn more about Chad King's work? Check out his website at https://rentmysoftware.com.Connect with Chad King on LinkedIn at https://www.linkedin.com/in/chadoking/.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? Check out his website at https://allies4me.com/.

May 21, 202631 min

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. Today, as CEO of BenefitRFP and a partner at Simplicity Group, he advises boards and leadership teams on retention, succession, and the financial structures that keep key people committed.In this episode, Bob shares what going behind enemy lines in Ukraine taught him about leadership under pressure, trust, and decision-making when the stakes are high. He explains why executive benefits are often misunderstood, breaks down how well-designed plans can improve retention without simply throwing money at people, and shows how tax strategy, culture, and long-term incentives work together to keep great employees in their seats. Bob also warns against bad advice in succession and deferred-compensation planning and makes the case for acting before top performers start looking elsewhere.Want to learn more about Bob Nienaber's work? Check out his website at https://benefitrfp.com/.Connect with Bob Nienaber on LinkedIn at https://www.linkedin.com/in/bobnienaberbrfp/.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? Check out his website at https://allies4me.com/.

May 14, 202631 min

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 clarity, team leadership, and community-driven growth, Jake shares real-world strategies for building businesses and people that last.In this episode, Jake discusses his journey from breaking his neck playing football to becoming a "fixer" for Hilton and Marriott hotels. He explains the fundamentals of business success, why the margin of excellence is razor-thin, and how Gathering the Kings helps entrepreneurs achieve success without sacrificing family.Want to learn more about Jake's work? Check out his website at https://gatheringthekings.com/.Connect with Jake on LinkedIn at https://www.linkedin.com/in/jake-isaacs-28071b41/.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/.

May 7, 202643 min

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, successfully competing against China at a time when conventional wisdom said it couldn't be done. Today, as founder of SERO Growth, he helps manufacturers expand into international markets and supports international organizations entering North America.In this episode, David challenges the myth that US manufacturing can't compete globally. He shares his "just-in-time" manufacturing approach that eliminated warehousing costs, explains why unit cost is only part of the equation, and reveals how his company achieved 40-45% gross margins while competitors struggled. David also breaks down the hidden costs of offshoring - from supply chain disruptions to cash flow tied up in goods on the water - and offers practical advice for manufacturers looking to enter new markets, including why starting small beats going big.Want to learn more about David Solomon's work? Check out their website at https://www.serogrowth.com/.Connect with David Solomon on LinkedIn at https://www.linkedin.com/in/davidsolomon13/.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/.

April 30, 202633 min

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 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 both your service offerings and your client selection. He explains why picking high-growth industries and rapidly growing clients matters more than raw talent, discusses the future of AI in financial planning, and reveals why structured data is the key to unlocking AI's potential. Jon also opens up about the challenges creative agency owners face when forced to become entrepreneurs and why getting into the financial weeds separates great CEOs from the rest.Want to learn more about Jon Morris's work? Check out their website at https://www.fiscaladvocate.com/.Connect with Jon Morris on LinkedIn at https://www.linkedin.com/in/jonmorrisramsayinnovations/.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/.

April 23, 202638 min

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 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 segregation that could save business owners tens or hundreds of thousands of dollars.Want to learn more about Pietro's work? Check out his website at https://ietaxattorney.com/.Connect with Pietro on LinkedIn at https://www.linkedin.com/in/pietro-canestrelli-18032a21.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/.

April 21, 202630 min

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 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 guide participants through meaningful learning moments.The conversation also covers the psychology of audience engagement, why attention spans are shrinking, and how simple tools like polling, chat prompts, and structured interaction can dramatically improve participation. Bernie also highlights common mistakes leaders make—such as overwhelming audiences with too much information and failing to provide a clear call to action.Ultimately, great virtual experiences come down to intentional leadership. When leaders design training and events that prioritize engagement and clarity, they build stronger relationships, deeper trust, and better business outcomes.Want to learn more about Bernie DeSantis's work? Check out their website at https://insigniatraining.com/.Connect with Bernie DeSantis on LinkedIn at https://www.linkedin.com/in/badiii/.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/.

April 16, 202635 min

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 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 transparency during difficult decisions, or showing curiosity instead of judgment, leaders have constant opportunities to strengthen relationships.She also highlights why organizations often overlook leadership development at the frontline level, where trust issues frequently begin. Without the right skills and emotional intelligence, leaders unintentionally damage the culture they’re responsible for building.Ultimately, Kim’s message is clear: trust is not abstract. It can be measured, strengthened, repaired, and intentionally built into how organizations operate.Want to learn more about Kim Bohr's work? Check out their website at https://sparkeffect.com/.Connect with Kim Bohr on LinkedIn at https://www.linkedin.com/in/kimbohr/.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/.