5 to 50: Financial Strategies for Growing Companies

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5 to 50: Financial Strategies for Growing Companies is a podcast hosted by Jeff Rudner. The podcast is your company's go-to resource for financial empowerment and strategic planning. Designed for entrepreneurs and business owners managing $5–$50 million in revenue, we deliver practical financial insights to help you scale your business, optimize cash flow, and harness the power of technology. Through conversations with SMB leaders and trusted advisors, we break down high-level financial strategies into actionable steps, empowering you to overcome challenges and achieve sustainable growth. Tune in to learn how to take your business to the next level!

  1. 15 - Navigating Startup Acquisition, Growth, and Exits with Jason Pearsall

    9 SEP

    15 - Navigating Startup Acquisition, Growth, and Exits with Jason Pearsall

    In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jason Pearsall, CEO of Club Caddie Holdings, about his evolution from startup founder to a private equity-backed business leader. Jason shares his lessons from two successful exits, the pivotal shifts in his golf technology business, and the art of balancing data with instinct. Jason shares his take on the importance of defining your ideal customer profile and a focus on due diligence for sustainable growth. He also highlights why success isn’t always about chasing VC funding but finding partners aligned with long-term goals while transforming traditional industries with technology.

    39 min
  2. 14 - Building a Revenue-on-Demand Engine with Gabe Lullo

    26 AGO

    14 - Building a Revenue-on-Demand Engine with Gabe Lullo

    In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Gabe Lullo, CEO of Alleyoop, to explore his journey from SDR to CEO and the lessons learned while scaling a 150-person revenue-on-demand company. Gabe shares insights on balancing rapid growth with financial discipline, diversifying client portfolios, and building scalable systems without compromising quality. He also reveals why investing 15–20% of revenue in sales and marketing can drive sustainable success and how leveraging content over cold calls builds trust and accelerates sales cycles. A must-listen for entrepreneurs scaling service businesses.

    35 min
  3. 13 - Guarding the Vault: Cybersecurity Strategies for Finance with Chithra Rajagopalan

    12 AGO

    13 - Guarding the Vault: Cybersecurity Strategies for Finance with Chithra Rajagopalan

    Is your finance department your company’s biggest security risk? Join Jeff Rudner on this episode of 5 to 50: Financial Strategies for Growing Companies as he welcomes Chithra Rajagopalan, Head of Finance at Obsidian Security, to discuss how the convergence of finance and cybersecurity can either expose companies to billion-dollar breaches or unlock strategic resilience. From managing phishing threats to balancing AI innovation with secure financial practices, Chithra shares practical, cost-effective tactics for protecting sensitive data and strengthening internal operations. Whether you're a founder, CFO, or finance leader, this episode is packed with insights to help you scale securely in today’s digital-first world.

    38 min
  4. 12 - Building a Business That Runs and Grows Without You: Insights from Alan Pentz

    29 JUL

    12 - Building a Business That Runs and Grows Without You: Insights from Alan Pentz

    Looking to scale your service-based business without drowning in operational chaos? Join Jeff Rudner on this episode of 5 to 50: Financial Strategies for Growing Companies as he sits down with Alan Pentz, founder and former CEO of Corner Alliance, to unpack how he scaled a consulting firm from startup to $35M in revenue. Alan shares actionable insights on evolving beyond founder-led sales, setting financial benchmarks like labor efficiency and gross margins, and making tough calls about leadership and systems. Tune in to learn how to work on your business, not just in it, and build a company that thrives without you.

    41 min
  5. 11 - Cash is Queen: Growth in Uncertain Markets with Joy Mbanugo, CFO at CXAI

    15 JUL

    11 - Cash is Queen: Growth in Uncertain Markets with Joy Mbanugo, CFO at CXAI

    What’s the smartest way to manage cash when the market is uncertain? In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Joy Mbanugo, CFO of CXAI and a former executive at Google and BlackRock, to answer that and more. Joy shares actionable strategies for maximizing cash reserves, navigating funding options, and evolving your finance function as your company scales. She also unpacks how AI is revolutionizing financial operations and why finance should be a central pillar of business strategy. This episode is packed with valuable insights for founders and CFOs who are ready to lead with confidence.

    32 min
  6. 10 - The Jetstream Effect: Kevin Diemar on Scaling Without the Overhead

    1 JUL

    10 - The Jetstream Effect: Kevin Diemar on Scaling Without the Overhead

    How do you grow a luxury service business without sacrificing quality or cash flow? In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Kevin Diemar, CEO and President of Unity Jets and former Wall Street trader, to uncover how Kevin scaled a private jet brokerage using relationship-driven strategies and an asset-light model. He shares powerful lessons on maintaining high-touch service, hiring smart, and managing emotional highs and lows in business. Kevin also shares how he evaluates angel investments by focusing on authenticity and connection. Whether you're scaling a client-focused business or exploring private markets, this episode offers practical, real-world insights for building lasting success.

    43 min
  7. 9 - Ali Firoozi on Turning Finance Teams Into Strategic Business Partners

    17 JUN

    9 - Ali Firoozi on Turning Finance Teams Into Strategic Business Partners

    What if you could transform your finance team from simply reporting numbers to being strategic business partners in the organization's growth? In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Ali Firoozi, CFO of The Pac Group, to explore how finance leaders can drive business growth through strategic insight and tech adoption. Ali shares his journey from aspiring lawyer to CFO and explains how finance teams must evolve from number crunchers to business storytellers. They discuss best practices for implementing new systems, selecting impactful KPIs, managing fixed vs. variable costs, and embracing AI. Packed with real-world wisdom, this episode is a must-listen for any leader modernizing their finance function.

    37 min
  8. 8 - Ex-Facebook Director: This AI Solves Finance's #1 Bottleneck

    3 JUN

    8 - Ex-Facebook Director: This AI Solves Finance's #1 Bottleneck

    Finance's #1 bottleneck is reconciliation. What if you could revolutionize your financial operations with AI while maintaining complete control and transparency? In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with ex-Facebook director and CEO and co-founder of Ledge, Tal Kirschenbaum, to discuss how AI is transforming financial operations for businesses in the accelerated scaling phase. He draws on his experience at BCG, Facebook, and Melio, to share actionable strategies for automating reconciliation, improving financial reporting, and building trust in AI-driven systems. The conversation covers the shift from manual to continuous close processes, balancing growth with control, and maintaining transparency in an AI-powered future. This episode is a must-listen for finance leaders and founders aiming to scale smart while staying compliant.

    36 min
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5 to 50: Financial Strategies for Growing Companies is a podcast hosted by Jeff Rudner. The podcast is your company's go-to resource for financial empowerment and strategic planning. Designed for entrepreneurs and business owners managing $5–$50 million in revenue, we deliver practical financial insights to help you scale your business, optimize cash flow, and harness the power of technology. Through conversations with SMB leaders and trusted advisors, we break down high-level financial strategies into actionable steps, empowering you to overcome challenges and achieve sustainable growth. Tune in to learn how to take your business to the next level!

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