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/
• super{set} Website: https://superset.com
• Email: [email protected]
  
  

super{set} Company Information:

• 
  super{set} on LinkedIn: https://linkedin.com/company/superset-studio
• TechCrunch Coverage: 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
• The Boy, the Mole, the Fox and the Horse (referenced in conversation)
  
  

Host & Proseer:

• 
  Jeff Rudner on LinkedIn: https://bit.ly/3DEGINH
• Proseer Website: https://proseer.co/
• Book a Consultation: https://proseer.co/contact/
• Download Our eBook - Transforming Accounting Solutions: 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
  
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon