Leaders & Legacies

Craig Andrews
  • 4.9 (106)
  • Entrepreneurship
  • Updated Weekly

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.

  1. 19h ago

    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 this episode, Craig Andrews talks with Fred Kosnac about why growth without financial context can create blind spots, especially for owners who are moving fast and trying to make decisions from incomplete numbers. Fred pushes back on the idea that a CFO is just the “chief no officer” or a glorified accountant. The best financial leaders help owners understand what the numbers mean, how they connect to the company’s goals, and how to make investments, hires, and growth decisions without putting the business at risk. Craig and Fred dig into the gap between historical reporting and forward-looking leadership. Fred explains why numbers alone do not tell the full story, how context changes the meaning of revenue and profitability, and why a business owner needs someone who can translate financial statements into decisions that actually move the company forward. They also explore what happens when growth exposes hidden problems, from delayed billing to margin pressure to cash constraints. Fred shares how Crystal Oak CFOs & Advisors helps owners build a clearer rhythm around sales, margins, profitability, cash, budgets, and forecasts so growth becomes more sustainable instead of more stressful. Want to learn more about Fred Kosnac's work? Check out his website at https://www.crystaloakcfo.com/. Connect with Fred Kosnac on LinkedIn at https://www.linkedin.com/in/fred-kosnac-cpa/. You can also reach Fred directly at fred@crystaloakcfo.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 Andrews' work at allies4me? Check out his website at https://allies4me.com/.

  2. Jul 9

    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 search, the real question is still whether your market can find useful, credible answers from you and about you. Chasing a mention inside ChatGPT or Claude is a shaky substitute for understanding what your customers need and what the web is already saying. In this episode of Leaders & Legacies, Craig talks with Stephan, CEO and Co-Founder of VibeLogic, about why companies often overlook the intelligence already sitting inside the business. Sales calls, support tickets, chat logs, legal review threads, and customer questions can reveal the exact problems buyers care about. What looks like a bullet point on your website may be someone else’s entire reason to buy. Stephan also separates AI leverage from AI fantasy. AI can help leaders change formats, test ideas, and turn long content into tools people will actually use. But it is not push-button expertise. Like Craig’s example of putting a non-driver in an F1 car, AI may help you move faster, but the judgment still comes from the person steering. The conversation closes with a look at where search is heading: toward agents, proactive recommendations, and systems that connect dots before a user types a query. That future still depends on what can be learned, verified, and trusted. For leaders, the work is not to panic over AI rankings. It is to make sure the right signals exist across the places where customers, platforms, and intelligent systems form opinions. Want to learn more about Stephan Bajaio’s work? Check out VibeLogic at https://www.vibelogic.com/. Connect with Stephan Bajaio on LinkedIn at https://www.linkedin.com/in/stephanbajaio/. 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/.

  3. Jul 2

    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 & Legacies, Craig talks with Salvatore Tirabassi about what founder-led and family-owned companies often miss in their finance function. Sal explains why useful reporting starts with a single source of truth, not another spreadsheet or visual layer on top of messy data. The conversation centers on bringing private-equity-grade finance to businesses that are not ready to hire a full executive team. That means practical reporting, forecasting, calculators, and workflows that help owners see what is really happening in the business. Sal also makes the case that reporting should not consume the month. When the process is built correctly, owners spend less time compiling numbers and more time analyzing what the numbers mean. Craig and Sal get into the metrics owners should understand cold: minimum cash, revenue, EBITDA, customer acquisition cost, customer lifetime value, employee tenure, and turnover. These numbers are not just finance trivia. They shape hiring, growth, cash decisions, and the owner’s ability to see risk early. They also discuss why a missed acquisition-cost target should not end with vague disappointment. The better question is where the funnel broke, what caused the miss, and what needs to change before more money gets poured into the same system. Want to learn more about Salvatore Tirabassi's work? Check out his website at https://cfoproanalytics.com/. Connect with Salvatore Tirabassi on LinkedIn at https://www.linkedin.com/in/stirabassi/. You can also reach Salvatore directly at stirabassi@cfoproanalytics.com. Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

  4. Jun 25

    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 litigator, former general counsel, and corporate business lawyer, Matt brings the perspective of someone who has both provided and purchased legal services. In this episode, Matt explains why business owners often misuse legal counsel by treating lawyers like vending machines: show up, pay money, demand a document, and disappear again. He makes the case for using a business lawyer as a contextual advisor who understands your company, your priorities, your risk tolerance, and where you are trying to go. Matt also covers how to choose the right lawyer, why vague contracts create litigation risk, and how middle-market founders can control legal costs without cutting corners on the issues that matter. Want to learn more about Matt Bracy's work? Visit Scheef & Stone at http://www.solidcounsel.com. Connect with Matt Bracy on LinkedIn at https://www.linkedin.com/in/mattbracy/. You can also reach Matt directly at matt.bracy@solidcounsel.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 Andrews' work at allies4me? Check out his website at https://allies4me.com/.

  5. Jun 18

    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 and COO, he brings a practical operator's perspective to the messy moment when a company has outgrown improvisation but has not yet built the structure needed to scale. In this episode, Gary shares how living in Ireland reshaped his view of pace and culture, why intentional cultures stay recognizable even as companies grow, and where scaling businesses most often go wrong. He explains the EOS idea of "right people, right seats," warns against designing roles around whoever happens to be available, and makes the case that consistency and accountability become essential once a company is ready to scale. Want to learn more about Gary Leeman's work? Visit his EOS Worldwide profile at https://implementer.eosworldwide.com/gary-leeman/. Connect with Gary Leeman on LinkedIn at https://www.linkedin.com/in/garyleeman/. You can also reach Gary directly at gary.leeman@eosworldwide.com or 469-816-4369. 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 https://allies4me.com/.

  6. Jun 11

    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/.

  7. Jun 4

    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/.

  8. May 28

    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/.

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4.9
out of 5
106 Ratings

About

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.

Information

  • Creator
    Craig Andrews
  • Years Active
    2023 - 2026
  • Episodes
    282
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Craig Andrews
  • Show Website
    Leaders & Legacies