5 to 50: Financial Strategies for Growing Companies

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jeremy Klein, General Partner at super{set}, a groundbreaking AI startup studio. Jeremy's unconventional journey—from teaching beekeeping in rural Paraguay as a Peace Corps volunteer to advising hundreds of startups as a corporate attorney, to now co-founding data and AI companies—offers a maste...

In this episode of 5 to 50: Financial Strategies for Growing Companies, Jeff Rudner sits down with Brandon Spear, CEO of TreviPay, whose three-decade career spans four continents and multiple successful exits. Brandon shares his journey from co-founding South Africa's first commercial internet service provider in the early 1990s to leading TreviPay through its recent private equity carve-out. He o...

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jordan Fishfeld, serial entrepreneur and founder of CoreGro, to explore the art of going from zero to one in business. Jordan shares his journey through multiple ventures—from real estate crowdfunding and private market investing to healthcare real estate—and the mindset shifts that shaped his s...

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Patrick Dichter, founder and owner of AppleTree Consulting, an accounting firm specializing in outsourced accounting and tax services for small to medium-sized businesses. Patrick shares his unique journey from business consultant to accounting firm owner, having grown his company from $1.2 mill...

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Kevin Diemar, a powerhouse in private aviation and seasoned angel investor, for his second appearance on the show. Kevin shares his fascinating journey into angel investing, starting with an impromptu investment in a men's yoga shorts company that became his greatest success. He reveals how he s...

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jonathan Hayek, a commercial real estate investor and host of "The Source of Commercial Real Estate" podcast. Jonathan shares his remarkable journey from special education teacher to successful industrial real estate investor, offering actionable insights on transitioning careers, building wealt...

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...

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 compro...

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 thr...

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...

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...

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 l...

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 j...

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 bus...

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Alex Glueckler, VP of Accounting at CrossFit, to discuss how finance can evolve from a reactive function into a proactive, strategic partner. Alex shares insights on simplifying financial metrics, building cross-functional relationships, and creating a finance culture that supports, not stifles,...

What if you could learn from someone who successfully scaled and sold a SaaS company in Europe before launching their next venture? In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Johan Hoernell, CEO and co-founder of Reveal Automation. Johan shares his journey from McKinsey consultant to successful SaaS entrepreneur, offering practical insig...

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with the dynamic duo of Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic. They share their evolution from crafting small-batch jams to leading a thriving manufacturing enterprise serving major meal kit brands. Learn how they balanced intuition with data, scaled operation...

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Tom Hunt, Founder and CEO of Fame, to uncover how he built a $4M ARR B2B podcast agency—without external funding. Tom shares lessons from 17 business attempts, the importance of financial discipline, and why focusing on core services drives sustainable success. They explore risk assessment, EOS...

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Kenny Dettman, Founder and CEO of TaxNow, a three-time founder and former Big 4 accounting partner, to discuss scaling service-based businesses. They explore building scalable processes, managing rapid team growth, and navigating regulatory challenges. Kenny shares insights on financial metrics,...

Welcome to 5 to 50: Financial Strategies for Growing Companies. In this episode, Jeff Rudner talks with Rick Zullo, founder and managing partner of Equal Ventures, about his transition from consulting to venture capital. They discuss talent's importance in startups, early-stage investing challenges, and the emotional rollercoaster of entrepreneurship. Rick shares insights on building successful co...

Welcome to 5 to 50: Financial Strategies for Growing Companies. In this episode, host Jeff Rudner sits down with Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic. Adam shares his entrepreneurial journey, emphasizing the power of aligning intention with attention, leveraging AI for workplace efficiency, and understanding operational data. From scaling TeePublic to launch...

🚀 The Wait is Almost Over! After months of preparation, we’re just ONE day away from launching the 5 to 50 Podcast by Proseer! 🎙️ If you're an entrepreneur or business owner managing $5M–$50M in revenue, this podcast is built for you. We’ll bring you expert financial insights, cash flow strategies, operational efficiencies, and cutting-edge tech solutions to help you scale smarter and faster.