3 - Scaling Smart: Financial & Growth Strategies for Service-Based Businesses with Kenny Dettman

5 to 50: Financial Strategies for Growing Companies

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:

• Kenny Dettman on LinkedIn
• TaxNow Website
• Jeff Rudner on LinkedIn
• Proseer Website

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