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 masterclass in adaptability and strategic thinking. In this conversation, Jeremy shares invaluable insights on what separates successful founders from the rest, how to systematize financial operations across portfolio companies, the critical metrics that drive B2B SaaS growth, and how to implement AI strategically in your business. Whether you're a founder seeking to scale or a finance leader building systems for growth, this episode delivers actionable wisdom on vision, grit, and building companies that last.

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 offers candid insights on navigating the 2008 financial crisis, turning around struggling businesses through customer-centric approaches, and preparing companies for strategic acquisitions. Brandon also discusses the future of B2B payments, the role of AI in creating competitive moats, and why building trust is the most undervalued leadership skill. Whether you're a founder preparing for an exit or scaling through uncertainty, this episode is packed with battle-tested wisdom from someone who's been there multiple times.

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 success. He discusses how to test and validate ideas, build lean, raise capital, and know when it's time to sell. Packed with insights on focus, risk, and execution, this episode is a masterclass for entrepreneurs at any stage.

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 million to $4.5 million in revenue through strategic acquisitions and organic growth. He offers candid insights on the challenges of change management, the reality of scaling a professional services firm, and the difficult decisions that come with rapid growth. From navigating client transitions to building accountability systems and expanding service lines, Patrick pulls back the curtain on what it really takes to build a modern accounting practice. Whether you're considering an acquisition, scaling your firm, or simply trying to build the right team, this episode is packed with real-world lessons from the trenches.

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 sources deals, evaluates opportunities, and builds relationships with founders across various industries—from apparel and mobility scooters to water brands and nutritional supplements. Kevin unpacks the importance of founder authenticity, the power of distribution channels, and why he invests in products he'd personally use. This episode is packed with actionable insights for founders seeking investment and entrepreneurs looking to diversify into angel investing.