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5 to 50: Financial Strategies for Growing Companies
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...
2025-07-01
42 min
5 to 50: Financial Strategies for Growing Companies
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...
2025-06-17
37 min
5 to 50: Financial Strategies for Growing Companies
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...
2025-06-03
36 min
5 to 50: Financial Strategies for Growing Companies
7 - Alex Glueckler on Turning Finance into a Growth Engine at CrossFit
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, 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.
2025-05-20
37 min
5 to 50: Financial Strategies for Growing Companies
6 - The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling
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 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...
2025-05-06
36 min
5 to 50: Financial Strategies for Growing Companies
5 - Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon
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 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.
2025-04-22
35 min
5 to 50: Financial Strategies for Growing Companies
4 - Bootstrapped to $4M ARR: Tom Hunt’s Insights on Sustainable Scaling
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 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...
2025-04-08
40 min
5 to 50: Financial Strategies for Growing Companies
3 - Scaling Smart: Financial & Growth Strategies for Service-Based Businesses with Kenny Dettman
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, 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...
2025-03-25
36 min
5 to 50: Financial Strategies for Growing Companies
2 - The Secrets to Scaling Startups with Rick Zullo of Equal Ventures
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 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...
2025-03-11
44 min
5 to 50: Financial Strategies for Growing Companies
1 - Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
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 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...
2025-02-25
38 min
5 to 50: Financial Strategies for Growing Companies
Five 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...
2025-02-24
01 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...
2023-12-08
50 min
The Thoughtful Entrepreneur
1719 - Proseer’s Proactive Approach to Accounting with Jeff Rudner
In 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...
2023-11-05
17 min
Profit With A Plan
EP217 Financial Integrations - Jeff Rudner
Marcia 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...
2023-08-15
34 min
The CTO Show with Mehmet Gonullu
#194 Financial Fluency for Startup Founders With Jeff Rudner
Ready 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...
2023-08-15
31 min
Accounting High
120 Creating a Trust Economy at Your Firm (feat. Jeff Rudner, CPA)
Episode 120 | Recorded January 23, 2023 Accounting High is supported by our Booster Club Members Thank you AppStream! Powered by the GrowthLab Music Video for Simple Tasks! 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...
2023-04-05
1h 03