Fame Host (https://fame.so) 5 to 50: Financial Strategies for Growing Companies https://podcasts.fame.so/5-to-50-financial-strategies-for-growing-companies https://feeds.fame.so/5-to-50-financial-strategies-for-growing-companies 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! Copyrights © 2025 All Rights Reserved by Proseer en Mon, 13 Jan 2025 15:46:48 +0000 Thu, 12 Mar 2026 19:44:44 +0000 https://content.fameapp.so/uploads/3l1n4w91/bb3401c0-0960-11f0-ac53-df00e27478b5/bb3402c0-0960-11f0-b7a5-adb42637d0fd.jpg 5 to 50: Financial Strategies for Growing Companies https://podcasts.fame.so/5-to-50-financial-strategies-for-growing-companies 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! Proseer 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! No No episodic Proseer 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! 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! thought leadership, financial insights, SMBs, strategic planning, financial literacy, community building, audience growth, financial strategy, scaling strategies, entrepreneurs, business owners, service-based industries, cloud-based accounting software, S Jeff Rudner team@fame.so No No No 21 - From Beekeeping in Paraguay to Building AI Companies - Lessons in Vision and Grit https://podcasts.fame.so/e/18330048-21-from-beekeeping-in-paraguay-to-building-ai-companies-lessons-in-vision-and-grit 21 - From Beekeeping in Paraguay to Building AI Companies - Lessons in Vision and Grit 21 No No m0jpkkz0 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, 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.


Episode Chapters:


00:00 Intro: Meet Jeremy Klein - From Peace Corps to Venture Capital


02:10 From Beekeeping in Paraguay to Building Trust and Overcoming Fear


03:44 The Leap from Peace Corps to Law and Startups


05:00 What Sets Great Founders Apart: Vision and Product Strategy


08:25 The Trough of Sorrow: How Successful Founders Persevere


11:00 Asking for Help Isn't Giving Up - It's the Opposite


11:43 What Makes super{set} Different: Company Building vs Traditional VC


14:03 Systematizing Success: Financial Models and Back Office Foundation


18:00 The Right Metrics: What to Measure and When


22:00 Cascading Vision: Creating Customer-Centric Culture as You Scale


24:38 Information Sharing: Balancing Transparency with Team Readiness


27:00 AI Strategy for Entrepreneurs: Picking the Right Problems to Solve


30:18 Avoiding Shiny Object Syndrome in the Age of AI


33:08 Finding Market Opportunities: Known Problems vs New Problems


35:04 Life Advice: It's a Marathon, Not a Sprint


37:17 Rapid Fire: AI Trends, Book Recommendations, and Hiring Strategy


Episode Resources:


Guest:


super{set} Company Information:


Books & Resources Mentioned:


Host & Proseer:


Key Takeaways:


On Founder Success:


  • Vision: The best founders articulate audacious, compelling visions that inspire investors and teammates
  • Product Strategy: Great founders see beyond the immediate and can articulate a clear path from today's product to tomorrow's platform
  • Open-Mindedness: Successful founders ask the right questions, know what they need to know, and trust experts to execute


On Financial Systems:


  • Start with financial models from day one—even when you're "making it up"
  • Models are vehicles for discussion and alignment across the entire team
  • Track 3-5 key metrics initially: ARR, CAC, pipeline, close times, and eventually NDR and gross margins
  • Create 3-year plans to test assumptions and avoid short-term thinking
  • Implement CRM systems (like HubSpot) from the beginning to build data-driven muscles


On AI Implementation:


  • Pick problems humans can't solve well or don't want to solve
  • Avoid core system replacements; focus on augmentation and specific pain points
  • Good AI problems: QA testing, compliance, documentation, security questionnaires
  • Focus on providing results, not just tools
  • Recognize AI's limitations and design accordingly


On Scaling Culture:


  • Embed customer-centricity as a core value from day one ("blueberries and pancakes")
  • Be selective about financial transparency—people aren't always equipped to process it
  • Maintain biweekly executive meetings and monthly all-hands for alignment
  • Hire strategically, even if it feels early—waiting too long costs more than acting early


About the Guest:


Jeremy Klein is a General Partner at super{set}, a startup studio that founds, funds, and builds AI and data-centric companies. Since super{set}'s inception in 2018, Jeremy has been instrumental in building a durable company-building machine across B2B SaaS, AI, and data management. The firm has founded over 20 companies and achieved its first major exit with Habu's $200 million acquisition in 2024. Prior to super{set}, Jeremy was a corporate attorney at Gunderson Dettmer, where he advised hundreds of technology startups and venture capital investors across all stages of growth. His unconventional background includes serving as a Peace Corps volunteer in rural Paraguay, where he taught beekeeping and learned invaluable lessons about trust, persuasion, and working with people—skills that continue to shape his approach to building companies today.


About 5 to 50 Podcast:


5 to 50: Financial Strategies for Growing Companies helps founders and finance leaders navigate the critical journey from $5M to $50M in revenue. Hosted by Jeff Rudner, each episode features conversations with successful entrepreneurs, CFOs, and investors who share practical strategies for scaling operations, managing cash, building finance functions, and implementing systems that support sustainable growth.



Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 02 Dec 2025 10:00:00 +0000 Proseer Proseer 2464 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, 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. No No 20 - Scaling Through Uncertainty: How Brandon Spear Built Adaptable Companies in Uncertain Times https://podcasts.fame.so/e/182rkwx8-20-scaling-through-uncertainty-how-brandon-spear-built-adaptable-companies-in-uncertain-times 20 - Scaling Through Uncertainty: How Brandon Spear Built Adaptable Companies in Uncertain Times 20 No No 2099xrl0 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, 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.


Episode Chapters:


00:00 Intro: Meet Brandon Spear, CEO & Serial Entrepreneur


02:00 Early Risks & The Birth of the Internet in South Africa


06:00 Turning Around Quadrant Through Customer Feedback


12:00 Navigating the 2008 Financial Crisis: Cutting Fat vs. Muscle


17:00 Preparing for Exit: Selling to Ariba in 2011


21:00 Joining TreviPay: 11 Years of Growth and Evolution


25:00 Choosing the Right Private Equity Partner


27:00 The Future of B2B Payments: AI, Digitization & Stable Coins


36:00 Building Leadership Teams: Timing Executive Hires Right


43:00 Rapid Fire: Career Lessons, Books & Leadership Skills


Episode Resources:


Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH


TreviPay Website: https://trevipay.com


Proseer Website: https://proseer.co/


Book a Consultation Contact Us: https://proseer.co/contact/


Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/


Book Mentioned:


The Innovator's Dilemma by Clayton M. Christensen - Available on Amazon: https://amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780



Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 18 Nov 2025 10:01:00 +0000 Proseer Proseer 2806 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, 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. No No 19 - Zero To One: Mastering The Entrepreneurial Journey with Jordan Fishfeld https://podcasts.fame.so/e/x8vlwky8-19-zero-to-one-mastering-the-entrepreneurial-journey-with-jordan-fishfeld 19 - Zero To One: Mastering The Entrepreneurial Journey with Jordan Fishfeld 19 No No 70ypvy41 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 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 stage.


Episode Chapters:


00:00 Intro: Meet Jordan Feld, Serial Entrepreneur and Founder of CoreGo
02:00 Solving Personal Problems as a Path to Innovation
04:15 Building a Real Estate Crowdfunding Platform
06:00 Creating a Secondary Market for Private Investments
08:00 The Power of Testing Small and Validating Ideas
10:30 Avoiding Risk and Building Smart
13:00 Finding Product-Market Fit in Real Estate Investing
15:00 Laser Focus and the Entrepreneurial Mindset
18:00 Building the Right Team for Growth
21:00 Raising Capital and Communicating Value
25:00 Investing Your Own Money in Every Deal
28:00 Tracking Performance and Financial Discipline
30:00 Hard Lessons Learned from the Entrepreneurial Journey
33:00 Knowing When to Sell and Start Again
36:00 The Joy of Going from Zero to One
37:00 Jordan’s Recommended Books for Entrepreneurs
39:00 Life Motto: "No Excuses, Don’t Fail"
40:00 Closing Thoughts and Where to Find Jordan Feld


Episode Resources:


Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH
Jordan Feld on LinkedIn: linkedin.com/in/jordanfishfeld
CoreGo Website: https://www.coregro.com/
Proseer Website: https://proseer.co/
Book a Consultation: https://proseer.co/contact/
Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/ 


Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 04 Nov 2025 10:00:00 +0000 Proseer Proseer 2470 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 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. No No 18 - Change Management in the Trenches: A Conversation About Embracing Change to Facilitate Growth https://podcasts.fame.so/e/lnqw4pln-18-change-management-in-the-trenches-a-conversation-about-embracing-change-to-facilitate-growth 18 - Change Management in the Trenches: A Conversation About Embracing Change to Facilitate Growth 18 No No 81nvx8w1 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 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.


Episode Chapters:


00:00 Introduction: Patrick's Unconventional Path to Accounting


05:00 Change Management: Why Team Transitions Are Harder Than Client Transitions


08:00 Acquisition Lessons: What Worked, What Failed, and Why


11:00 Building Multiple Revenue Streams and Service Lines


14:00 The Reality of Scaling: Growth Sweet Spots and Growing Pains


19:00 Creating a Culture of Accountability with Scorecards and KPIs


22:00 Strategic Planning: Reaching the $5 Million Milestone


26:00 Systems and Technology for Scale: EOS and Practice Management


30:00 Flying Solo: The Pros and Cons of Single Ownership


32:00 Rapid Fire: Books, Metrics, and Essential Business Advice


Episode Resources:


Patrick Dichter on Twitter (X): https://twitter.com/PatrickDichter


Patrick Dichter on LinkedIn: https://linkedin.com/in/patrickdichter


AppleTree Business Website: https://appletreebusiness.com


Book: The E-Myth Revisited by Michael E. Gerber: https://amazon.com/Myth-Revisited-Small-Businesses-About/dp/0887307280


Canopy Practice Management: https://getcanopy.com


Traction (EOS - Entrepreneurial Operating System): https://eosworldwide.com


Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH


Proseer Website: https://proseer.co/


Book a Consultation Contact Us: https://proseer.co/contact/


Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/



Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 21 Oct 2025 09:00:00 +0000 Proseer Proseer 2221 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 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. No No 17 - Kevin Diemar on Angel Investing https://podcasts.fame.so/e/q80vw028-17-kevin-diemar-on-angel-investing 17 - Kevin Diemar on Angel Investing 17 No No p0kn86r1 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. 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.

Episode Chapters:

00:00 Intro: Kevin Diemar Returns to Discuss Angel Investing
01:30 How Kevin Got Started: From Shorts Purchase to Series A Investment
07:44 Building Deal Flow and Learning from Winners vs. Losers
15:26 The Importance of Communication and Financial Discipline
22:17 The Liquid Death Investment: Distribution as a Key Factor
29:21 Investment Process: From Product Testing to Founder Due Diligence
34:16 Return Expectations and Secondary Market Strategy
42:19 Sourcing Deals: Being a Hunter in Angel Investing
43:13 Lightning Round: Pitch Deck Essentials, Metrics, and Founder Advice

Episode Resources:

Kevin Diemar on LinkedIn: https://www.linkedin.com/in/kevindiemar
Unity Jets: https://unityjets.com/
Vuori Clothing: https://vuoriclothing.com/
Liquid Death Water: https://liquiddeath.com/
Vuori at REI: https://www.rei.com/b/vuori

Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH

Proseer Website: https://proseer.co/
Book a Consultation Contact Us: https://proseer.co/contact/
Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/ 

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 07 Oct 2025 09:00:00 +0000 Proseer Proseer 2872 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. 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. No No 16 - How a Former Teacher Built a Thriving Industrial Portfolio https://podcasts.fame.so/e/xn12lkk8-16-how-a-former-teacher-built-a-thriving-industrial-portfolio 16 - How a Former Teacher Built a Thriving Industrial Portfolio 16 No No 703rvmm1 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 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.
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 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 Chapters:


00:00 From Teacher to Real Estate Investor
02:05 Why Real Estate?
05:08 First Deal Breakdown
10:46 Getting Comfortable with Debt
16:56 Transitioning to Industrial Properties
25:40 Why Syndications Are Struggling
29:20 Navigating Market Cycles
33:38 Real Estate Tax Benefits
36:30 Betting on Yourself
38:23 Rapid Fire Questions


Episode Resources:

Jonathan Hayke Website: jonathanhayek.co 
BiggerPockets Real Estate Podcast: https://www.biggerpockets.com/podcasts/real-estate 
Monday.com Project Management Software: https://monday.com/ 

"The Source of Commercial Real Estate" Podcast - Available on all podcast platforms

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Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 23 Sep 2025 12:18:00 +0000 Proseer Proseer 2463 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 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. 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 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. No No 15 - Navigating Startup Acquisition, Growth, and Exits with Jason Pearsall https://podcasts.fame.so/e/286q79kn-startup-acquisition-growth-jason-pearsall 15 - Navigating Startup Acquisition, Growth, and Exits with Jason Pearsall 15 No No j12rmn61 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. 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 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 goals while transforming traditional industries with technology.


What you will learn:
  • How to identify and pivot when your initial business model isn't meeting market needs
  • The critical importance of defining your Ideal Customer Profile (ICP) before scaling
  • Why tracking specific KPIs and financial metrics is essential for successful acquisitions
  • How to balance founder vision with investor expectations when choosing funding partners
  • Differences between managing a startup versus a private equity-backed company
  • Why is integrating operational and financial systems is crucial for business scalability
  • How to transform traditional businesses through technology 
  • The essential metrics for running a successful golf course operation


Jeff Pearsall is the CEO and co-founder of Club Caddie Holdings, a comprehensive golf course management software solution. With a background in corporate law and deep roots in the golf industry, Jeff has successfully grown and exited multiple businesses, including leading two golf course acquisitions and achieving a notable exit to Constellation Software. His journey from founding Golfler, an early golf-tech startup, to building Club Caddie into a market leader demonstrates his expertise in scaling technology companies and optimizing golf course operations.


Episode Resources:


Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 09 Sep 2025 09:00:00 +0000 Proseer Proseer 2322 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. 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. Golf course management, business acquisition, startup exits, financial due diligence, Club Caddie software, operational metrics, Customer experience management, revenue forecasting, business model pivots, ideal customer profile, golf course operations, business valuation No No 14 - Building a Revenue-on-Demand Engine with Gabe Lullo https://podcasts.fame.so/e/lnqwl75n-building-revenue-engine-gabe-lullo 14 - Building a Revenue-on-Demand Engine with Gabe Lullo 14 No No 81nvwm31 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. 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.


What you will learn:
  • How to build mental resilience in sales by categorizing objections into 10 core buckets 
  • Why does it take 90 days to properly establish sales development campaigns 
  • How to balance aggressive growth with financial sustainability 
  • The framework for diversifying client portfolios: maintaining 40% enterprise and 60% SMB clients for stability
  • Why organic content marketing is replacing traditional sales collateral
  • Implement the "democratic leadership" approach when driving organizational change
  • The 15-20% revenue guideline for sales and marketing spend 
  • Why leveraging content over cold calls can accelerate sales cycles
  • How to transition from an individual contributor to a leader by shifting focus 


Gabe Lullo is the CEO of Alleyoop, a revenue-on-demand partner helping brands like Adobe, Bevy, and ZoomInfo scale with confidence. Rising from SDR to CEO, Gabe has built deep expertise in enterprise software sales, people operations, and revenue generation. At Alleyoop, he has grown the team to 150+ employees while pioneering scalable, content-driven sales strategies. As host of the Do Hard Things podcast, Gabe shares insights on sustainable growth, client partnerships, and building resilient, high-performing sales organizations.


Episode Resources:
Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 26 Aug 2025 08:30:00 +0000 Proseer Proseer 2080 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. 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. Sales development strategy, revenue scaling, enterprise sales, CEO leadership, content marketing strategy, business growth tactics, sales team management, and financial sustainability, SDR to CEO journey, sales objection handling, client diversification, professional services growth, sales metrics, recruitment strategy, team development, organic marketing No No 13 - Guarding the Vault: Cybersecurity Strategies for Finance with Chithra Rajagopalan https://podcasts.fame.so/e/2n6qzv68-cybersecurity-strategies-finance-chithra-rajagopalan 13 - Guarding the Vault: Cybersecurity Strategies for Finance with Chithra Rajagopalan 13 No No j02r8390 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. 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.


What you will learn:
  • How to quantify cybersecurity risks and their potential financial impact 
  • Why separating finance and security departments is crucial for maintaining expertise
  • The critical importance of proper user access management 
  • How to implement cost-effective security measures for early-stage companies 
  • Why multi-factor authentication and proper data hygiene are non-negotiable 
  • How to balance AI adoption in finance while maintaining security and data protection
  • The framework for creating effective partnerships between CFOs and CISOs
  • Why centralized data management must be balanced against security considerations
  • How to protect against increasingly sophisticated phishing attacks 
  • The essential security protocols every finance department should implement


Chithra Rajagopalan is a seasoned finance leader with deep experience in high-growth SaaS companies. Currently Head of Finance at Obsidian Security, she has successfully led organizations through fundraises, acquisitions, international expansion, and IPO readiness. With prior roles at Deloitte and fast-paced startups, she’s known for her strategic insight, operational rigor, and strong executive partnership. Chithra also serves on the boards of two non-profits focused on nurse retention and social equity for underprivileged children, reflecting her commitment to impact beyond business.




Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 12 Aug 2025 08:30:00 +0000 Proseer Proseer 2276 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. 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. Cybersecurity finance, financial security, data protection, risk management, finance leadership, security breaches, business cybersecurity, Data hygiene, multifactor authentication, phishing attacks, user privileges, breach prevention, security compliance, financial data protection No No 12 - Building a Business That Runs and Grows Without You: Insights from Alan Pentz https://podcasts.fame.so/e/r8klv76n-building-business-insights-alan-pentz 12 - Building a Business That Runs and Grows Without You: Insights from Alan Pentz 12 No No 71wjw6m0 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. 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.


What you will learn:
  • How to evolve from founder-led sales to building a scalable sales organization
  • Why gross margins must exceed 40% to create a sustainable business
  • The critical financial metrics for tracking service business health
  • How to strategically build your leadership team as you scale from $2M to $35M 
  • Why proper financial systems and projections are essential before scaling past $5M
  • The framework for transitioning from working in the business to working on it
  • How to identify when loyal early employees are blocking company growth
  • The optimal timing for implementing new systems and processes 
  • Why equity compensation rarely makes sense in privately held service businesses 
  • How to achieve owner independence while maintaining strategic control 


Alan Pentz is the founder and former CEO of Corner Alliance, a firm dedicated to enhancing digital infrastructure for federal programs in areas including broadband, cybersecurity, and public safety. With over two decades of consulting experience across government and corporate sectors, Alan has developed significant expertise in organizational transformation and business scaling strategies. Through his latest venture, His practical approach to business growth is based on learnings from scaling Corner Alliance to $35 million in revenue.




Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 29 Jul 2025 08:30:00 +0000 Proseer Proseer 2472 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. 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. Business scaling strategies, financial management, company growth stages, leadership transition, revenue optimization, Gross margin analysis, sales team development, business systems implementation, operational efficiency, founder transition, professional services management No No 11 - Cash is Queen: Growth in Uncertain Markets with Joy Mbanugo, CFO at CXAI https://podcasts.fame.so/e/p8m7r2q8-growth-markets-joy-mbanugo-cxai 11 - Cash is Queen: Growth in Uncertain Markets with Joy Mbanugo, CFO at CXAI 11 No No 70v5yxv1 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. 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.


What you will learn:
  • How to strengthen your balance sheet by prioritizing cash during economic uncertainty 
  • Why distinguishing between different types of cash is crucial for decision-making
  • The strategic approach to scaling your finance function 
  • How to position finance as a central function 
  • Why EBITDA and other key metrics should be understood across the company
  • How to leverage AI tools in finance operations
  • The differences between debt and equity financing and how to choose the right funding strategy
  • Why cash management should be a daily priority


Joy Mbanugo is the CFO of CXApp (NASDAQ: CXAI), where she leads financial strategy, capital allocation, and investor relations for the innovative SaaS company. With a background at Google, BlackRock, and EY, she brings deep expertise in public company finance, board governance, and scaling high-growth businesses. Joy excels at aligning financial operations with business strategy, driving transparency, and building investor confidence. A lawyer and accountant, she’s also an active investor and advocate for women-led ventures and equitable growth in the startup ecosystem.


Episode Resources:
Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 15 Jul 2025 08:30:00 +0000 Proseer Proseer 1893 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. 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. Financial strategy, cash management, business finance, balance sheet optimization, CFO leadership, financial stewardship, Operational cash flow, debt management, business runway, financial metrics, EBITDA tracking, and financial forecasting No No 10 - The Jetstream Effect: Kevin Diemar on Scaling Without the Overhead https://podcasts.fame.so/e/1n2rz7xn-jetstream-kevin-diemar-scaling-overhead 10 - The Jetstream Effect: Kevin Diemar on Scaling Without the Overhead 10 No No 2199vnl1 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. 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.


What you will learn:
  • How to pivot from transactional to relationship-based models while maintaining profitability
  • The "Never Too High, Never Too Low" principle for managing emotions 
  • Why transparency and honesty are crucial for building long-term client relationships 
  • How to scale a service business without compromising quality 
  • The "Asset Light" strategy for growing a service business while maintaining cash flow
  • How to identify and capitalize on market opportunities 
  • Why letting successful ventures grow naturally is more effective than rapid scaling
  • The framework for evaluating investment opportunities 


Kevin Diemar is the Founder of UnityJets, a global private jet brokerage built on a capital-light model and exceptional client service. A former Wall Street trader and VP of Sales at MarquisJet, Kevin brings deep expertise in high-stakes financial markets and luxury sales. He’s a seasoned CEO known for scaling relationship-driven businesses in private aviation. With strengths in negotiation, business planning, and entrepreneurship, Kevin has redefined what it means to grow a high-end service brand with integrity and precision.


Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 01 Jul 2025 08:30:00 +0000 Proseer Proseer 2552 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. 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. Private aviation business, scaling strategies, relationship-based sales, asset-light business model, customer service excellence, Business growth metrics, sales management, capital management, client relationship management, boutique service delivery No No 9 - Ali Firoozi on Turning Finance Teams Into Strategic Business Partners https://podcasts.fame.so/e/182rzm48-finance-teams-strategic-business-partners 9 - Ali Firoozi on Turning Finance Teams Into Strategic Business Partners 9 No No 2099vy70 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. 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.


What you will learn:
  • How numbers tell compelling business stories
  • Why modern finance departments must evolve from reporting to becoming strategic business partners
  •  The challenges and best practices of implementing new financial systems
  • How to select and track meaningful KPIs that drive business success 
  • The critical balance between fixed and variable costs in professional services firms
  • The transformative impact of AI on financial operations and team productivity


Ali Firoozi is the Chief Financial Officer at The PAC Group, a global consulting and engineering firm. With over 20 years of experience in finance, Ali brings an entrepreneurial mindset and a proven ability to lead through growth and change. He specializes in financial strategy, forecasting, process design, and executive reporting. A former banking professional with degrees in International Business and Finance and an MBA, Ali excels at integrating finance with innovation to drive enterprise value and strategic partnerships.


Episode Resources:

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 17 Jun 2025 08:30:00 +0000 Proseer Proseer 2227 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. 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. Financial leadership, business strategy, financial analysis, corporate finance, financial reporting, strategic planning, KPI management, expense management, financial metrics, business intelligence, revenue growth, cost control No No 8 - Ex-Facebook Director: This AI Solves Finance's #1 Bottleneck https://podcasts.fame.so/e/l8qwy5l8-facebook-director-ai-finance-bottleneck 8 - Ex-Facebook Director: This AI Solves Finance's #1 Bottleneck 8 No No 80nv53w0 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. 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.


What you will learn:
  • How to transition from manual to automated financial processes
  • Why progressive automation is key to successful AI adoption in finance teams
  • The critical balance between growth and financial sustainability, when backed by VC
  • How to build trust in AI-powered financial solutions 
  • How to resolve reconciliation at companies on the growth path
  • How to evolve from reactive accounting to continuous close processes 
  • The importance of early technology investments 
  • How to maintain founder mentality and accountability as your organization grows


Tal Kirschenbaum is the CEO and Co-founder of Ledge, an AI-powered platform revolutionizing financial operations for mid-market and enterprise companies. With an impressive background spanning roles at BCG, Facebook, and Melio, Tal brings deep finance, technology, and strategic operations expertise to his entrepreneurial ventures. Drawing from his experience at Melio, where he witnessed firsthand the challenges of high-volume financial reconciliation, Tal founded Ledge to address the growing complexity of financial operations through intelligent automation. His leadership has positioned Ledge as a pivotal solution for businesses seeking to enhance their financial processes, particularly in cash reconciliation and journal entry creation.


Episode Resources:

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 03 Jun 2025 08:30:00 +0000 Proseer Proseer 2178 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. 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. Financial automation, AI in finance, reconciliation software, fintech solutions, enterprise finance, cash reconciliation, how to automate reconciliation, AI for small business finance, scaling finance team, continuous close accounting explained, Ledge AI review, best fintech for startups, Payment processing automation, financial operations, startup journey, business scaling, continuous accounting, and journal entry automation No No 7 - Alex Glueckler on Turning Finance into a Growth Engine at CrossFit https://podcasts.fame.so/e/xnvl0w4n-alex-glueckler-finance-growth-crossfit 7 - Alex Glueckler on Turning Finance into a Growth Engine at CrossFit 7 No No 71yp9vj0 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. 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.


What you will learn:
  • How to build a strategic finance function that enables growth 
  • Why simplifying KPIs to 2-3 core metrics creates better alignment and decision-making
  • The "Strategic No" framework for finance leaders to guide business decisions 
  • How to embed finance throughout the organization by building relationships 
  • Why understanding accounting and finance fundamentals is crucial for business scaling
  • How to balance short-term cash management with long-term value creation
  • How to develop servant leadership in finance to build a high-performing team 
  • The critical role of the balance sheet in ensuring long-term business sustainability


Alex Glueckler is an accomplished finance executive with over 18 years of experience spanning accounting, operations, and strategic leadership, with more than a decade in private equity-backed companies from startup to IPO and exit. As VP of Accounting at CrossFit, LLC, he leads global accounting operations, ensuring financial transparency and compliance. Known for aligning financial strategy with business goals, Alex is passionate about building strong stakeholder relationships and driving growth that supports CrossFit’s mission to improve health, happiness, and performance.


Episode Resources:
Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 20 May 2025 08:30:00 +0000 Proseer Proseer 2262 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. 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. Financial strategy, business scaling, financial leadership, CFO insights, cash flow management, business growth metrics, finance department optimization, KPI tracking, financial reporting, internal controls, accounting processes, financial transparency, strategic partnerships, data analytics, revenue targets No No 6 - The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling https://podcasts.fame.so/e/p8m5z1z8-exit-playbook-johan-hoernell-selling 6 - The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling 6 No No 70vl8z80 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 company, Johan’s strategies around operational excellence, financial leadership, and entrepreneurial resilience provide invaluable lessons for building and exiting technology ventures. 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 company, Johan’s strategies around operational excellence, financial leadership, and entrepreneurial resilience provide invaluable lessons for building and exiting technology ventures.


What you will learn:
  • Why transparent financial metrics and company-wide KPI visibility drive better results
  • The "Context Over Control" leadership principle for empowering teams 
  • How to build effective finance operations from bookkeeper to CFO 
  • Why pre-acquisition preparation and financial hygiene are crucial for a smooth exit 
  • The strategic framework for bootstrapping a new venture 
  • How to identify the right moment to exit a business 
  • The importance of focusing on core competencies and outsourcing critical functions 


Johan Hoernell is the CEO and Co-founder of Reveal Automation, specializing in the automation and enablement of enterprise digital tools. With a distinguished background including strategic consulting at McKinsey and successfully scaling Time Edit to acquisition, Johan brings deep expertise in technology optimization and business transformation. His entrepreneurial journey spans from early programming interests to executive leadership, where he successfully led Time Edit's expansion from a Nordic-focused company to a broader market presence.


Episode Resources:

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 06 May 2025 08:30:00 +0000 Proseer Proseer 2175 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 company, Johan’s strategies around operational excellence, financial leadership, and entrepreneurial resilience provide invaluable lessons for building and exiting technology ventures. 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 company, Johan’s strategies around operational excellence, financial leadership, and entrepreneurial resilience provide invaluable lessons for building and exiting technology ventures. Entrepreneurial journey, business scaling, startup growth, McKinsey experience, enterprise software, automation technology, SaaS business, Financial reporting, team management, data analytics, business metrics, change management, strategic planning, product development No No 5 - Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon https://podcasts.fame.so/e/5nzx6x9n-sabrina-valle-and-jessica-quon 5 - Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon 5 No No 80z727k1 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. 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.


What you will learn:
  • How to identify when to pivot from a passion project to a scalable business model
  • Why establishing efficient systems and automation is crucial for lean team operations
  • The framework for evaluating new business opportunities 
  • How to build and maintain strong relationships with strategic partners
  • Why regional growth strategy often outperforms immediate national expansion 
  • The importance of maintaining robust cash flow 
  • The decision-making process for accepting or declining new business opportunities
  • Why keeping operations lean can be a competitive advantage in manufacturing
  • How to balance gut instinct with data-driven decision making in business growth


Episode Resources:

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 22 Apr 2025 08:30:00 +0000 Proseer Proseer 2104 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. 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. CPG manufacturing, food business scaling, co-packing services, business partnerships, startup growth, manufacturing operations, business pivot strategies, Cash flow management, production efficiency, co-manufacturing solutions, business forecasting, inventory management, operational scaling, client relationships No No 4 - Bootstrapped to $4M ARR: Tom Hunt’s Insights on Sustainable Scaling https://podcasts.fame.so/e/18pv63m8-tom-hunt 4 - Bootstrapped to $4M ARR: Tom Hunt’s Insights on Sustainable Scaling 4 No No z1r3kxp0 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 key to growth. 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 key to growth.

Here are some key discussion topics:
  • From 17 Failed Startups to Success: Tom Hunt's Journey
  • Risk Assessment Framework: Likelihood × Impact
  • Building Culture: Scaling Values Across 70+ Team Members
  • Cash Flow Management: Bootstrapping Growth
  • Evolution of Systems and Processes at Fame
  • Metrics That Matter: Using EOS to Track Performance
  • The Power of Focus: Building a World-Class Service
  • Navigating Growth Challenges: Revenue vs. Profitability
  • Rapid Fire: Financial Insights and Tools


Episode Resources:


Books Recommended by Tom Hunt
Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 08 Apr 2025 08:30:00 +0000 Proseer Proseer 2415 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 key to growth. 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 key to growth. B2B podcast agency, Business scaling strategies, Financial management for entrepreneurs, Bootstrap business growth, Service company profitability, Cash flow optimization, Operating systems implementation, Team management strategies, Business metrics tracking, Company culture development, Process documentation, Performance bonus structures No No 3 - Scaling Smart: Financial & Growth Strategies for Service-Based Businesses with Kenny Dettman https://podcasts.fame.so/e/4892pmrn-kenny-dettman 3 - Scaling Smart: Financial & Growth Strategies for Service-Based Businesses with Kenny Dettman 3 No No v17v3rp0 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. 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 Journey
  • The Entrepreneurial Mindset: Identifying Opportunities
  • Scaling from 0 to 60: Managing Rapid Growth
  • Building Systems & Processes: The Assembly Line Approach
  • Tech Stack Evolution: Finding the Right Tools
  • Financial Metrics: From Service Business to Tech Startup
  • The Importance of Early Financial Infrastructure
  • Managing Risk in Regulated Industries
  • Rapid Fire: Leadership Insights & Final Thoughts


Episode Resources:
Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 25 Mar 2025 09:00:00 +0000 Proseer Proseer 2161 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. 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. business scaling strategies, financial technology for SMBs, entrepreneur growth tactics, business process optimization, startup financial management, tax compliance technology, business scaling tips, financial reporting systems, business metrics tracking, startup cash flow management, financial process automation, business decision making, revenue optimization strategies, scaling operations management No No 2 - The Secrets to Scaling Startups with Rick Zullo of Equal Ventures https://podcasts.fame.so/e/2n61kj78-rick-zullo 2 - The Secrets to Scaling Startups with Rick Zullo of Equal Ventures 2 No No j02264m0 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. 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 Business Ownership  
  • Analyzing Talent in Startups  
  • Emotional Highs and Lows of Founders  
  • Transitioning to Structured Processes  
  • Preparing for an Exit


Episode Resources:
Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 11 Mar 2025 09:33:00 +0000 Proseer Proseer 2684 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. 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. Early-stage investing, Venture capital, Startup growth, Capital formation, Investment strategies, Entrepreneurial Journey No No 1 - Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth https://podcasts.fame.so/e/r8kmxy38-adam-schwartz 1 - Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth 1 No No 71w7yv81 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! 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 Entrepreneurship  
  • The Importance of Timing in Exits  
  • Parable's Mission to Optimize Time

Adam Schwartz is a seasoned entrepreneur and innovator in e-commerce. As Co-Founder and CEO of TeePublic, he scaled the company to $130M in revenue before its acquisition by Redbubble. TeePublic empowered creatives to turn passion into profit, enabling artists to sell millions of designs globally without raising outside capital. Previously, Adam was COO of BustedTees, a comedy-focused merchandise platform, and Co-Founder of TheLoyalist, an e-commerce tool for celebrities and media brands. Adam’s ventures reflect his commitment to empowering creators and scaling impactful businesses.


Episode Resources:

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Tue, 25 Feb 2025 12:00:00 +0000 Proseer Proseer 2322 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! 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! entrepreneurship, operational efficiency, AI in business, business growth strategies, startup success, lean startup methodology, product market fit, data-driven decision making, scaling businesses, resource allocation No No Five to Fifty Podcast https://podcasts.fame.so/e/28x06268-five-to-fifty-podcast Five to Fifty Podcast 0 No No 60m6vmv1 🚀 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. 🚀 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 technologies

The trailer is live NOW—get a sneak peek at what’s coming! 🎧 Listen, follow, and be the first to tune in when we launch tomorrow!

#5to50Podcast #ScalingSmarter #BusinessGrowth #ComingSoon

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.

Check out our three most downloaded episodes:


]]> Mon, 24 Feb 2025 12:00:00 +0000 Proseer Proseer 60 🚀 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. 🚀 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. No No