

Leaders & Legacies
Craig Andrews
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.
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.
Episodes
Mentioned books

Aug 7, 2025 • 39min
217 - Why Every Leader Should Write a Book - Insights from Everett O’Keefe
Everett O’Keefe shares the origin story of Ignite Press, from a chance reconnection to a publishing powerhouse. His leadership was tested early when co-founder John tragically passed away, forcing Everett to carry the vision forward alone. Instead of folding, he doubled down. That decision sparked the launch of nearly 200 bestselling books and reshaped how thought leaders share their message.In this episode, Everett unpacks the power of books as a leadership tool—helping entrepreneurs build credibility, refine their message, and amplify their impact. He also offers a practical roadmap through the complex publishing landscape, covering ghostwriting, hybrid models, and the importance of editorial integrity.His message is clear: authorship is leadership. A book is more than a marketing tool—it’s a durable asset that outlives trends, outlasts platforms, and outperforms expectations. For Everett, real leadership means using your voice to unlock someone else’s potential.Want to learn more about Everett O’Keefe's work? Check out their website at https://IgnitePress.us.Connect with Everett O’Keefe on LinkedIn at https://www.linkedin.com/in/everettokeefe/.Get a complimentary copy of The Power of the Published: https://mypodcastperk.com/.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/.

Aug 5, 2025 • 32min
216 - Empowering Business Owners - Tax Strategies with Mike Jesowshek
Mike Jesowshek, founder of TaxElm, delivers a masterclass on leadership by eliminating one of the biggest pain points for entrepreneurs: tax confusion. His leadership style centers on simplifying complexity and empowering clients and employees through clear strategy and execution. On the Leaders and Legacies podcast, Mike breaks down how he uses transparency, consistency, and responsiveness to lead both a growing team and a national client base.Mike shares how most accountants are overworked or hesitant to charge for high-value advice, leaving business owners in the dark. His leadership challenge was to change that. By launching TaxElm and building a proactive software tool backed by expert support, he created a system that doesn’t just educate—it equips.He explains how he built trust through consistent communication, set clear expectations with his team, and scaled impact with tech and systems. His leadership isn’t about doing more—it’s about doing the right things and making those repeatable.Want to learn more about Mike Jesowshek’s work? Check out their website at https://www.TaxElm.com.Connect with Mike Jesowshek on LinkedIn at https://www.linkedin.com/in/mikejesowshek/.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/.

Jul 31, 2025 • 33min
215 - Building a Workforce from Scratch - Michael Cole’s Leadership in the Trades
Michael Cole, President of Next Level Technician, shares how he turned a failed Subway franchise and a few unlikely training classes into a thriving staffing and training company in the low-voltage trades. In a field plagued by high turnover and unpredictability, Cole stands out by building systems that value integrity and grit over credentials. His leadership journey is rooted in real-world trial and error—like discovering too late that some recruits are afraid of ladders or can’t pass drug tests.Michael’s leadership sharpens through adversity: he reshaped his business model after nearly every early mistake. His approach to staffing centers on deep vetting, video interviews, and second chances for people who own their past mistakes. He’s built a company that sets clear expectations, values honesty, and adapts without lowering standards. This episode is a masterclass in leading imperfect people to create powerful outcomes.Want to learn more about Michael Cole's work? Check out their website at https://www.nextleveltechnician.com.Connect with Michael Cole on LinkedIn at https://www.linkedin.com/in/coles-corner/.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/.

Jul 29, 2025 • 40min
214 - Bring the Magic of Disney to Any Business with Vance Morris
Vance Morris doesn’t just deliver services—he designs unforgettable experiences. In this episode, he shares how Disney’s obsession with systems shaped his philosophy for building customer loyalty and price elasticity. Morris breaks down his transition from security guard at a birth control factory to Disney executive, then to bankrupt entrepreneur, and finally to the founder of Deliver Service Now. His key insight? Competing on price kills service.Instead, Morris urges business owners to map every customer touchpoint and turn each one into a moment of delight. He explains how even something as small as baking cookies in a dentist’s office or FedExing a proposal can shift your brand from transactional to relational. Whether you’re in retail, B2B, or professional services, Morris shows how intentional design builds brand loyalty, repels price shoppers, and increases profitability.Want to learn more about Vance Morris's work? Check out their website at https://vancemorris.com.Connect with Vance Morris on LinkedIn at https://www.linkedin.com/in/vancemorris/.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/.

Jul 24, 2025 • 32min
213 - How Data-Driven Decisions Fuel Confident Leadership with Tom Dillon
Tom Dillon, founder of Frak Finance, joins Craig Andrews to break down how smart financial leadership unlocks business growth. As a fractional CFO, Tom helps companies escape the trap of gut-based decisions and start leading with data. He exposes the cost of common blind spots—like selling at a loss, underestimating hiring costs, or ignoring traction metrics.Tom shows how predictable revenue isn’t a myth—it’s a method. From analyzing ROI on marketing channels to knowing when to hire ahead of growth, he explains how leaders can build confidence through numbers. He also tackles the tension between branding and financial metrics, arguing that long-term value often looks unpredictable in a spreadsheet but is crucial to sustained success.Leadership, Tom says, is about accountability—not just managing costs but owning outcomes. His insights push leaders to stop hiding from the financials and start using them as tools to scale.Want to learn more about Tom Dillon's work? Check out their website at https://www.frakfinance.com.Connect with Tom Dillon on LinkedIn at https://www.linkedin.com/in/tom-dillon-cfa/.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/.

Jul 22, 2025 • 42min
212 - Leadership Through Purpose - How Kirk Spahn Helps Students Excel On and Off the Court
Kirk Spahn brings leadership to life at ICL Academy, a school built for students who aim higher—on the court, on the stage, or in their communities. In this conversation, Kirk breaks down what it takes to lead with purpose. He shares how ICL moves beyond academics to develop discipline, resilience, and character. The goal? To build champions for life.Kirk reveals how elite athletes and performers grow not just through hard work but through intentional structure and mindset. He details how ICL pairs students with mentors, designs custom curriculum around passions, and instills the habits of high-performance leadership. Whether training with Novak Djokovic or guiding a student to the French Open, Kirk’s focus stays the same: build people who lead with integrity and impact.He also addresses equity in education, explaining how ICL delivers personalized, values-driven schooling to students—90% of whom are on scholarship. The model blends traditional respect with forward-thinking tech, ensuring students thrive both online and in the world.Want to learn more about Kirk Spahn's work? Check out their website at https://www.iclacademy.org.Connect with Kirk Spahn on LinkedIn at https://www.linkedin.com/in/kirk-spahn-10a913/.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/.

Jul 17, 2025 • 43min
211 - Own Your Lane - Michelle Griffin's Framework for Leading with Clarity
Michelle Griffin joins Craig Andrews to deliver a sharp message for leaders flying under the radar—visibility is not vanity, it's your responsibility. As founder of Brand Leaders and creator of the “Own Your Lane” framework, Michelle helps professionals become the go-to voice in their space. In this episode, she breaks down the four key steps of her method: Launch Your Vision, Articulate Your Difference, Navigate Your Brand, and Elevate Your Authority.She argues that talent alone doesn’t get you noticed—strategic visibility does. Michelle challenges leaders to define their purpose, clarify their niche, and own a positioning that sets them apart. Her framework moves from internal clarity to external credibility, enabling leaders to drive impact, attract opportunities, and grow their authority. She also dismantles the myth that branding is only for big-budget companies. Her message is clear: if you’re not telling your story, someone else is—or worse, no one is.Want to learn more about Michelle Griffin's work? Check out her website at https://michellebgriffin.com/.Connect with Michelle Griffin on LinkedIn at https://www.linkedin.com/in/michellebgriffin/.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/.

Jul 15, 2025 • 32min
210 - Building Systems That Set You & Your Business Free - Lessons from David Forster
David Forster joins Craig Andrews to dismantle one of the most persistent myths in business: that people are the problem. With eight businesses under his belt, Forster explains why 94% of business issues stem from broken or missing processes—not bad hires. He shares how simplifying systems, building checklists, and offloading mental bandwidth into clear SOPs empowers teams to thrive.Craig and David dive into leadership lessons learned the hard way—like when Forster realized his wife was miserable in a "successful" business, or when Craig’s team kept the company running while he lay in a coma. Forster explains how true leadership means letting go of control and creating scalable systems that free both the owner and the team.He also breaks down why simplicity beats complexity, and how business owners can build a company that doesn’t rely on their daily involvement—creating optionality, not dependency.Want to learn more about David Forster's work? Check out their website at https://www.systemsoversweat.com.Connect with David Forster on LinkedIn at https://www.linkedin.com/in/rdavidforster/.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/.

Jul 10, 2025 • 31min
209 - From Green Beret to Cybersecurity Leader - Josh Wathen on Business Resilience
Josh Wathen, COO of Triad InfoSec and former Green Beret, joins Craig Andrews to sound the alarm on a growing leadership challenge: cyber resilience. In a world where ransomware is a billion-dollar business and hackers operate in full-fledged corporate teams, Josh breaks down why small businesses are soft targets—and how leadership complacency can be fatal.He shares hard-earned insights into the psychology of cyber threats, the high failure rate of insurance claims, and why reactive security costs 10x more than prevention. Josh outlines a leadership approach rooted in responsibility, training, and smart risk transfer. His advice? Stop assuming you're safe. Get real, get proactive, and lead by example.Want to learn more about Josh Wathen's work? Check out their website at https://triadinfosec.io.Connect with Josh Wathen on LinkedIn at https://www.linkedin.com/in/joshua-wathen/.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/.

Jul 8, 2025 • 43min
208 - The Three Keys to Success - Philip Portman's Formula for Leading Growth
Philip Portman, founder of Textdrip and author of Three Keys to Success, shares his raw journey through entrepreneurship and leadership. At his lowest point—deep in debt, grieving the loss of his dog, and questioning his choices—Philip made a commitment: he would never work for anyone else again. That moment became his turning point.In this episode, he explains how personal hardship catalyzed business growth, ultimately scaling his startup across six states. Philip lays out the three pillars of his leadership philosophy: written goals, healthy habits, and what he calls “arrogant confidence”—a mindset just bold enough to fuel breakthrough action.He also digs into the power of SMS marketing, explaining why it delivers stronger engagement than email and how to use it without annoying your audience. His insights on human connection, especially in a world saturated with AI-generated content, emphasize authenticity as a core leadership trait.Want to learn more about Philip Portman's work? Check out their website at https://philportman.com.Connect with Philip Portman on LinkedIn at https://www.linkedin.com/in/philportman/.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/.


