18 - Change Management in the Trenches: A Conversation About Embracing Change to Facilitate Growth

21 - From Beekeeping in Paraguay to Building AI Companies - Lessons in Vision and Grit

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: * Jeremy Klein on LinkedIn: https://linkedin.com/in/jeremy-s-klein/ [https://linkedin.com/in/jeremy-s-klein/] * super{set} Website: https://superset.com [https://superset.com] * Email: jeremy@superset.com super{set} Company Information: * super{set} on LinkedIn: https://linkedin.com/company/superset-studio [https://linkedin.com/company/superset-studio] * TechCrunch Coverage: https://techcrunch.com/2019/10/02/superset/ [https://techcrunch.com/2019/10/02/superset/] Books & Resources Mentioned: * The Qualified Sales Leader: Proven Lessons from a Five Time CRO by John McMahon: https://amazon.com/Qualified-Sales-Leader-Proven-Lessons/dp/0578895064 [https://amazon.com/Qualified-Sales-Leader-Proven-Lessons/dp/0578895064] * The Boy, the Mole, the Fox and the Horse (referenced in conversation) Host & Proseer: * Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH [https://bit.ly/3DEGINH] * Proseer Website: https://proseer.co/ [https://proseer.co/] * Book a Consultation: https://proseer.co/contact/ [https://proseer.co/contact/] * Download Our eBook - Transforming Accounting Solutions: https://proseer.co/rules-ebook/ [https://proseer.co/rules-ebook/] 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: * Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth [https://podcasts.fame.so/e/r8kmxy38-adam-schwartz] * The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling [https://podcasts.fame.so/e/p8m5z1z8-exit-playbook-johan-hoernell-selling] * 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]

20 - Scaling Through Uncertainty: How Brandon Spear Built Adaptable Companies in Uncertain 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 [https://bit.ly/3DEGINH] Brandon Spear on LinkedIn: https://linkedin.com/in/brandon-spearhttps://www.linkedin.com/in/brandon-spear-171a112/ [https://www.linkedin.com/in/brandon-spear-171a112/]  TreviPay Website: https://trevipay.com [https://trevipay.com] TreviPay on LinkedIn: https://linkedin.com/company/trevipay [https://linkedin.com/company/trevipay] Proseer Website: https://proseer.co/ [https://proseer.co/] Book a Consultation Contact Us: https://proseer.co/contact/ [https://proseer.co/contact/] Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/ [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 [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: * Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth [https://podcasts.fame.so/e/r8kmxy38-adam-schwartz] * The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling [https://podcasts.fame.so/e/p8m5z1z8-exit-playbook-johan-hoernell-selling] * 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]

19 - Zero To One: Mastering The Entrepreneurial Journey with Jordan Fishfeld

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 [https://bit.ly/3DEGINH] Jordan Feld on LinkedIn: linkedin.com/in/jordanfishfeld [http://linkedin.com/in/jordanfishfeld] CoreGo Website: https://www.coregro.com/ [https://www.coregro.com/] Proseer Website: https://proseer.co/ [https://proseer.co/] Book a Consultation: https://proseer.co/contact/ [https://proseer.co/contact/] Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/ [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: * Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth [https://podcasts.fame.so/e/r8kmxy38-adam-schwartz] * The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling [https://podcasts.fame.so/e/p8m5z1z8-exit-playbook-johan-hoernell-selling] * 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]

18 - Change Management in the Trenches: A Conversation About Embracing Change to Facilitate Growth

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 [https://twitter.com/PatrickDichter] Patrick Dichter on LinkedIn: https://linkedin.com/in/patrickdichter [https://linkedin.com/in/patrickdichter] AppleTree Business Website: https://appletreebusiness.com [https://appletreebusiness.com] Book: Unreasonable Hospitality by Will Guidara: https://amazon.com/Unreasonable-Hospitality-Remarkable-Restaurants-Business/dp/0593418573 [https://amazon.com/Unreasonable-Hospitality-Remarkable-Restaurants-Business/dp/0593418573] Book: The E-Myth Revisited by Michael E. Gerber: https://amazon.com/Myth-Revisited-Small-Businesses-About/dp/0887307280 [https://amazon.com/Myth-Revisited-Small-Businesses-About/dp/0887307280] Canopy Practice Management: https://getcanopy.com [https://getcanopy.com] Traction (EOS - Entrepreneurial Operating System): https://eosworldwide.com [https://eosworldwide.com] Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH [https://bit.ly/3DEGINH] Proseer Website: https://proseer.co/ [https://proseer.co/] Book a Consultation Contact Us: https://proseer.co/contact/ [https://proseer.co/contact/] Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/ [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: * Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth [https://podcasts.fame.so/e/r8kmxy38-adam-schwartz] * The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling [https://podcasts.fame.so/e/p8m5z1z8-exit-playbook-johan-hoernell-selling] * 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]

17 - Kevin Diemar on 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 [https://www.linkedin.com/in/kevindiemar] Unity Jets: https://unityjets.com/ [https://unityjets.com/] Vuori Clothing: https://vuoriclothing.com/ [https://vuoriclothing.com/] Liquid Death Water: https://liquiddeath.com/ [https://liquiddeath.com/] Vuori at REI: https://www.rei.com/b/vuori [https://www.rei.com/b/vuori] Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH [https://bit.ly/3DEGINH] Proseer Website: https://proseer.co/ [https://proseer.co/]Book a Consultation Contact Us: https://proseer.co/contact/ [https://proseer.co/contact/] Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/ [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: * Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth [https://podcasts.fame.so/e/r8kmxy38-adam-schwartz] * The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling [https://podcasts.fame.so/e/p8m5z1z8-exit-playbook-johan-hoernell-selling] * 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]