21 - From Beekeeping in Paraguay to Building AI Companies

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: jeremy@superset.com

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.