Shows
5 to 50: Financial Strategies for Growing Companies21 - From Beekeeping in Paraguay to Building AI Companies - Lessons in Vision and GritIn 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...
2025-12-0241 min
5 to 50: Financial Strategies for Growing Companies20 - Scaling Through Uncertainty: How Brandon Spear Built Adaptable Companies in Uncertain TimesIn 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...
2025-11-1846 min
5 to 50: Financial Strategies for Growing Companies19 - Zero To One: Mastering The Entrepreneurial Journey with Jordan FishfeldIn this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jordan Feld, serial entrepreneur and founder of CoreGo, 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 stag...
2025-11-0441 min
5 to 50: Financial Strategies for Growing Companies18 - Change Management in the Trenches: A Conversation About Embracing Change to Facilitate GrowthIn 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...
2025-10-2137 min
5 to 50: Financial Strategies for Growing Companies17 - Kevin Diemar on Angel InvestingIn 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 in...
2025-10-0747 min
5 to 50: Financial Strategies for Growing Companies16 - How a Former Teacher Built a Thriving Industrial PortfolioIn 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 wealth through real estate, and scaling from residential to commercial properties. He discusses overcoming limiting beliefs about income, creative financing strategies for new investors, and why he pivoted from small multifamily properties to net-leased industrial assets for true passive income.Episode...
2025-09-2341 min
5 to 50: Financial Strategies for Growing Companies15 - Navigating Startup Acquisition, Growth, and Exits with Jason PearsallIn 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 perspective on the importance of defining your ideal customer profile and the value of due diligence for sustainable growth. He also highlights why success isn’t always about chasing VC funding but about finding partners aligned with long-term go...
2025-09-0938 min
5 to 50: Financial Strategies for Growing Companies14 - Building a Revenue-on-Demand Engine with Gabe LulloIn 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.What you will learn:Ho...
2025-08-2634 min
5 to 50: Financial Strategies for Growing Companies13 - Guarding the Vault: Cybersecurity Strategies for Finance with Chithra RajagopalanIs 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...
2025-08-1237 min
5 to 50: Financial Strategies for Growing Companies12 - Building a Business That Runs and Grows Without You: Insights from Alan PentzLooking 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...
2025-07-2941 min
5 to 50: Financial Strategies for Growing Companies11 - Cash is Queen: Growth in Uncertain Markets with Joy Mbanugo, CFO at CXAIWhat’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...
2025-07-1531 min
5 to 50: Financial Strategies for Growing Companies10 - The Jetstream Effect: Kevin Diemar on Scaling Without the OverheadHow 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...
2025-07-0142 min
5 to 50: Financial Strategies for Growing Companies9 - Ali Firoozi on Turning Finance Teams Into Strategic Business PartnersWhat 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...
2025-06-1737 min
5 to 50: Financial Strategies for Growing Companies8 - Ex-Facebook Director: This AI Solves Finance's #1 BottleneckFinance'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...
2025-06-0336 min
5 to 50: Financial Strategies for Growing Companies7 - Alex Glueckler on Turning Finance into a Growth Engine at CrossFitIn 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, growth. He emphasizes the importance of servant leadership, the balance sheet’s role in long-term sustainability, and the value of early embedding finance in strategic planning. Whether you’re scaling or optimizing, this episode delivers actionable strategies for financial leadership at every stage.
2025-05-2037 min
5 to 50: Financial Strategies for Growing Companies6 - The Exit Playbook: Johan Hoernell’s Secrets to Scaling and SellingWhat 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 insights on scaling businesses, building transparent financial systems, and preparing for successful exits. He explains why empowering teams through context, rather than control, is vital for sustainable growth. Whether you're growing your first startup or leading a growth-stage SaaS...
2025-05-0636 min
5 to 50: Financial Strategies for Growing Companies5 - Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica QuonIn 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 operations with lean teams, and made tough calls while prioritizing long-term growth. With hard-won insights on pivoting business models, optimizing systems, and maintaining profitability, this episode is a must-listen for CPG founders looking to scale smartly without sacrificing sustainability.
2025-04-2235 min
5 to 50: Financial Strategies for Growing Companies4 - Bootstrapped to $4M ARR: Tom Hunt’s Insights on Sustainable ScalingIn 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 implementation, and the role of culture in scaling. Whether you're bootstrapping or scaling, this episode delivers actionable strategies on cash flow, profitability, operational efficiency, and team incentives. Tune in to learn why doing less—exceptionally well—is the ke...
2025-04-0840 min
5 to 50: Financial Strategies for Growing Companies3 - Scaling Smart: Financial & Growth Strategies for Service-Based Businesses with Kenny DettmanIn 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, risk management, and decision-making frameworks that drive sustainable growth. Whether you're a corporate leader eyeing entrepreneurship or a founder looking to scale, this episode delivers actionable financial strategies.Here are some key discussion topics:From Big 4 Partner to Entrepreneur: Kenny's JourneyThe Entrepreneurial Mindset...
2025-03-2536 min
5 to 50: Financial Strategies for Growing Companies2 - The Secrets to Scaling Startups with Rick Zullo of Equal VenturesWelcome 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 companies, from managing team dynamics to knowing when to implement structure as businesses scale. This episode offers valuable advice for entrepreneurs navigating the world of venture capital and scaling startups.Here are some key discussion topics:The Journey to Entrepreneurship The Realities of Small B...
2025-03-1144 min
5 to 50: Financial Strategies for Growing Companies1 - Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial GrowthWelcome 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 launching Parable, Adam offers valuable lessons on adaptability, team alignment, and driving impactful growth. Don’t miss this insightful conversation filled with actionable advice!Here are some key discussion topics:The Early Entrepreneurial Spirit Wearing Multiple Hats Speed Over Perfection The Seasonal Nature of Entre...
2025-02-2538 min
5 to 50: Financial Strategies for Growing CompaniesFive to Fifty Podcast🚀 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.💡 What to expect?✅ Actionable advice from top industry experts✅ Real-world strategies to master cash flow & optimize operations✅ Insights on leveraging the latest financial technologiesThe trailer is live NOW—get a sneak pe...
2025-02-2401 min
Drink While You Think🍺Drink While You Think: Ask Me Anything Edition 🎙️In this episode of Drink While You Think, Kenji Kuramoto & Matthew May share a beer and tackle their first Ask Me Anything episode!Tune in for…👉 Welcome! (00:00)👉 This Week's Topic & Beers (00:04)👉 Matthew’s Hot Tub Excursion (03:40)👉 Has Matthew Barbie-ized Himself? (05:25)👉 The Secret Sauce For Firms (07:05)👉 Biggest Breakthrough For CAS In 2024? (09:00)👉 Matthew’s Time As A Chambelan In Quinceañeras (11:53)👉 Is Kenji Still Brewing Beer? (14:50)👉 Improvements For Tech Partners (15:31)👉 Our Favorite CEOs In Accounting (19:40)👉 How Many Drinks Matthew Needs To G...
2023-12-0850 min
The Thoughtful Entrepreneur1719 - Proseer’s Proactive Approach to Accounting with Jeff RudnerIn this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks to Co-Founder & COO of Proseer, Jeff Rudner.
Jeff Rudner is the co-founder and CEO of Procedure, a modern accounting firm that is redefining how small and medium-sized businesses operate. Proseer's unique approach combines people, processes, and technology to help companies to scale and work more efficiently.
One of the standout aspects of Proseer is its productized pricing. This upfront approach eliminates the element of surprise, allowing clients to access support and advice without the fear of hourly billing.
Jeff emphasized that this approach alleviates friction between clients and...
2023-11-0517 min
Profit With A PlanEP217 Financial Integrations - Jeff RudnerMarcia talks with CPA, CFO, & Financial Expert, Jeff Rudner with Proseer, an accounting, tax and finance firm, about how small businesses can easily integrate software and automated processes into their business. The benefits are numerous from cutting costs to quick and accurate financial projections Jeff also shares that understanding your company's data is important for every decision and it should be easy to obtain across every department. Once set up, many types of software can cross communicate to make sure that the data is timely and on point.
Jeff is happy to offer a free consultation and...
2023-08-1534 min
The CTO Show with Mehmet Gonullu#194 Financial Fluency for Startup Founders With Jeff RudnerReady to decode the world of startup accounting and finance? Join us as we navigate through this complex landscape with Jeff Rudner, the co-founder of Proseer, a modern accounting firm. His expertise in financial reporting and accounting demystifies the process, making it digestible for all. Jeff focuses on the importance of comprehensible financials that can be shared with investors and lenders, offering advice on crafting a clear financial narrative that paints an accurate picture of your startup.
We then shift our focus onto setting a North Star goal, identifying the attributes to power business...
2023-08-1531 min
Accounting High120 Creating a Trust Economy at Your Firm (feat. Jeff Rudner, CPA)Episode 120 | Recorded January 23, 2023
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In this episode of Accounting High, Scott chats with Jeff Rudner, co-founder and COO of Proseer. Jeff shares his journey into cloud accounting, his experience with fractional CFO services, and the birth of Proseer. They talk about consolidating and partnering, and conversion to a C-corp. Other things covered are tech stack, pricing and services, and the importance of team structure. Join in as Jeff shares his insights o...
2023-04-051h 03