CEO Stories with Jonathan Herps

Jonathan Herps
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Honest conversations with the CEOs of growing private businesses: how they built it, what broke along the way, and what they'd do differently. I'm Jonathan Herps. I've spent 26 years as a CEO and 11 years coaching CEOs, and I've interviewed 133+ of them on this show. Every episode is a CEO telling the real story: the moment what got them here stopped working, the thing they held onto too long, the role they hired too late, and how they built a business that doesn't need them in every decision. Alongside the interviews you'll find The CEO Playbook, short teaching episodes where I share the tools I use with the CEOs I coach. If you're a founder or CEO growing a private business and want to learn from people who've been there, this show is for you. Website: www.scaleupos.comYouTube: www.youtube.com/@jonathanherpsLinkedIn: www.linkedin.com/in/jonathanherpsEmail: jonathan@scaleupos.com

  1. 12/12/2025

    How Zaki Ameer Scaled DDP Property to Australia’s Top 0.4% : EP 130

    In this episode of Stories of Scale, host Jonathan Herps sits down with Zaki Ameer, Founder of DDP Property, to unpack the real story behind his 15-year journey building one of Australia’s most successful buyer’s agencies. Zaki reveals the truth behind scaling a business sustainably — from navigating compliance and hiring misalignment, to rebuilding culture, and creating a business that can run without him. You’ll learn:  🔹 Why your values matter more than your strategy  🔹 How to build an A-player team that actually delivers  🔹 Why compliance can make or break your business  🔹 What founders get wrong when scaling  🔹 How personal identity, burnout and self-reflection shape your CEO evolution Whether you're a business owner, founder, or CEO — this episode is packed with real-world lessons on leadership, execution, and building a life that works beyond the business. Connect with Zaki Ameer: DDP Website - http://www.ddpproperty.com.au/ LinkedIn - https://www.linkedin.com/in/zakiameer/ CONNECT WITH JONATHAN HERPS Website: www.scaleupos.com LinkedIn: www.linkedin.com/in/jonathanherps Youtube: www.youtube.com/@jonathanherps Email: jonathan@scaleupos.com  🚀 Ready to Elevate Your Business? If you’re interested, here are 3 ways I can help you right now:  1. Subscribe to our podcast Get actionable strategies to run a more efficient business from someone who built & exited 3 multi-million $ companies. Click Here to listen & subscribe now!  2. Download our free CEO Dashboard template  Build a step-by-step business plan for consistent growth.  Click Here to download. 3. Book a 20-min Business Growth Call Map out a growth plan for your business and identify your biggest bottleneck & leave with a clear action plan. — Click Here

  2. 11/07/2025

    CEO Playbook EP 29: 6 Triggers to Escape the “Ones and Threes” Trap as a CEO

    Are you still doing everything yourself — sales, delivery, and strategy — and can’t take a holiday without things falling apart? You’re not alone. Most founders hit the same growth ceilings — the “ones and threes” — where your leadership, systems, and team hit capacity.   In this episode of the **Scale Up OS Podcast**, we unpack the **6 key triggers** to help you move from *firefighter* to *builder* — so your business can grow beyond you.   You’ll also learn why only 4% of businesses ever reach $1M revenue (and how to make sure you do), the mindset shift every CEO must make, and how AI can now help you scale faster than ever.   📍 **Timestamps** 00:00 Introduction: Overcoming Business Challenges 00:38 Personal Experience and Credibility 02:00 Understanding the Valleys of Death 03:19 Global Business Statistics 04:14 CEO Mind Shift: From Firefighter to Builder 04:48 Leveraging AI for Business Efficiency 05:43 Interactive AI Exercise 06:17 Conclusion and Podcast Subscription CONNECT WITH JONATHAN HERPS Website: www.scaleupos.com LinkedIn: www.linkedin.com/in/jonathanherps Youtube: www.youtube.com/@jonathanherps Email: jonathan@scaleupos.com  🚀 Ready to Elevate Your Business? If you’re interested, here are 3 ways I can help you right now:  1. Subscribe to our podcast Get actionable strategies to run a more efficient business from someone who built & exited 3 multi-million $ companies. Click Here to listen & subscribe now!  2. Download our free CEO Dashboard template  Build a step-by-step business plan for consistent growth.  Click Here to download. 3. Book a 20-min Business Growth Call Map out a growth plan for your business and identify your biggest bottleneck & leave with a clear action plan. — Click Here

  3. 10/24/2025

    CEO Playbook EP 28: Build a Culture That Attracts A-Players and Keeps Them

    In this episode of the Scale Up OS Podcast, Jonathan Herps dives deep into why building and keeping A-players is the ultimate growth advantage for CEOs. Discover how leading founders are creating workplaces that attract talent, boost performance, and scale sustainably — even in competitive markets. 💡 You’ll Learn: 1.  Use People & Culture KPIs that actually drive results 2.  Benchmark your eNPS and measure team health effectively 3.  Build a culture that makes your business a “great place to work” 4.  Hire A-players (and move out the toxic ones fast) 5.  Avoid burnout and build a team that leads with you CONNECT WITH JONATHAN HERPS Website: www.scaleupos.com LinkedIn: www.linkedin.com/in/jonathanherps Youtube: www.youtube.com/@jonathanherps Email: jonathan@scaleupos.com  🚀 Ready to Elevate Your Business? If you’re interested, here are 3 ways I can help you right now:  1. Subscribe to our podcast Get actionable strategies to run a more efficient business from someone who built & exited 3 multi-million $ companies. Click Here to listen & subscribe now!  2. Download our free CEO Dashboard template  Build a step-by-step business plan for consistent growth.  Click Here to download. 3. Book a 20-min Business Growth Call Map out a growth plan for your business and identify your biggest bottleneck & leave with a clear action plan. — Click Here

  4. 10/14/2025

    CEO Playbook EP 27: How CEOs Use KPIs, A-Players, and B.A.M.s to Scale Smarter

    Perfection slows growth. Momentum scales it. In this episode of the Scale Up OS Podcast, Jonathan Herps breaks down how growth-stage founders can take control of their business using leading vs. lagging KPIs, “Bare Ass Minimums” (BAMs), and a flywheel system that drives consistent performance. You’ll also hear real-world examples of businesses scaling from $3M to $17M — and what it really takes to keep profit, people, and progress aligned. 💡 You’ll Learn: The difference between leading and lagging KPIs — and why it mattersWhat “Bare Ass Minimums” (BAMs) are and how to set them for your teamHow A-Players outperform and transform company growthWhy momentum beats perfection in scalingHow to adjust KPIs as your business evolves CONNECT WITH JONATHAN HERPS Website: www.scaleupos.com LinkedIn: www.linkedin.com/in/jonathanherps Youtube: www.youtube.com/@jonathanherps Email: jonathan@scaleupos.com  🚀 Ready to Elevate Your Business? If you’re interested, here are 3 ways I can help you right now:  1. Subscribe to our podcast Get actionable strategies to run a more efficient business from someone who built & exited 3 multi-million $ companies. Click Here to listen & subscribe now!  2. Download our free CEO Dashboard template  Build a step-by-step business plan for consistent growth.  Click Here to download. 3. Book a 20-min Business Growth Call Map out a growth plan for your business and identify your biggest bottleneck & leave with a clear action plan. — Click Here

  5. 10/03/2025

    CEO Playbook EP 26: AI, Dashboards, and the North Star - How CEOs Can Lead Smarter with the Right Tools

    In this episode of the Scale Up OS Podcast, Jonathan Herps explores how CEOs can harness AI, dashboards, and the power of a North Star metric to lead with more clarity and alignment. From using multiple AI tools for research and decision-making, to understanding why defining and tracking the right metrics drives real momentum, this episode is packed with practical insights you can apply today. What You’ll Learn in This Episode AI is a force multiplier when used with the right mix of tools—not just ChatGPT.Great prompts drive great outcomes; AI is only as good as the questions you ask.Keep sensitive data secure by separating personal and enterprise AI use.A North Star Metric aligns your entire company around one guiding measure of success.Momentum beats perfection—start with workable metrics, then refine as you scale. CONNECT WITH JONATHAN HERPS Website: www.scaleupos.com LinkedIn: www.linkedin.com/in/jonathanherps Youtube: www.youtube.com/@jonathanherps Email: jonathan@scaleupos.com  🚀 Ready to Elevate Your Business? If you’re interested, here are 3 ways I can help you right now:  1. Subscribe to our podcast Get actionable strategies to run a more efficient business from someone who built & exited 3 multi-million $ companies. Click Here to listen & subscribe now!  2. Download our free CEO Dashboard template  Build a step-by-step business plan for consistent growth.  Click Here to download. 3. Book a 20-min Business Growth Call Map out a growth plan for your business and identify your biggest bottleneck & leave with a clear action plan. — Click Here

  6. 09/26/2025

    CEO Playbook EP 25: AI-Powered CEO Dashboard, Lead Smarter in 20 Minutes a Week

    Most CEOs are drowning in numbers but starving for clarity. Without the right dashboard, you’re flying blind—reacting instead of leading. In this session,  Jonathan shared AI prompts to design your Leaders KPIs, company Evergreen KPIs & an AI prompt to help you identify your North Star metric. Whether you’re at $1M, $10M, or $100M in revenue, the principles are the same. If you can’t measure it, you can’t optimise it—and if you can’t optimise it, you can’t scale. CONNECT WITH JONATHAN HERPS Website: www.scaleupos.com LinkedIn: www.linkedin.com/in/jonathanherps Youtube: www.youtube.com/@jonathanherps Email: jonathan@scaleupos.com  🚀 Ready to Elevate Your Business? If you’re interested, here are 3 ways I can help you right now:  1. Subscribe to our podcast Get actionable strategies to run a more efficient business from someone who built & exited 3 multi-million $ companies. Click Here to listen & subscribe now!  2. Download our free CEO Dashboard template  Build a step-by-step business plan for consistent growth.  Click Here to download. 3. Book a 20-min Business Growth Call Map out a growth plan for your business and identify your biggest bottleneck & leave with a clear action plan. — Click Here

  7. 09/19/2025

    CEO Playbook EP 24: Charting a Three-Year Vision - From Strategy to Execution

    Every founder dreams big, but too many stop at “vision” without turning it into an actionable plan. In this episode, Jonathan Herps breaks down how to take a 3-year vivid vision and transform it into a practical execution system that drives growth, profit, and freedom. Jonathan reveals the planning rhythms used by top CEOs to scale past the plateaus, align leadership teams, and free themselves from being the bottleneck in their business. Whether you’re aiming to break through $3M, $10M, or beyond, this episode gives you the clarity and tools to lead with intent. What You’ll Learn in This Episode Why 3 years is the ideal time horizon for strategy and scaling The “leader’s intent” framework for aligning your executive team How to cascade a vivid vision into quarterly sprints and weekly check-ins The 4 essential jobs of every CEO in growth mode Tools to keep execution disciplined and results predictable In this episode of Stories of Scale with Jonathan Herps, you’ll discover: 00:00 Introduction: Why Three Years? 00:32 Real-Life Example: Achieving Market Leadership 02:55 Communicating the Three-Year Plan 04:06 The Role of a CEO 05:53 Executing the Vision: Quarterly and 12-Quarter Plans 08:53 Case Study: Making Sales Predictable 11:32 Tracking Success: The CEO Dashboard  14:17 Q&A and Final Thoughts CONNECT WITH JONATHAN HERPS Website: https://www.scaleupos.com/ LinkedIn: https://www.linkedin.com/in/jonathanherps/ Youtube: https://www.youtube.com/@jonathanherps/ Email: jonathan@scaleupos.com  🚀 Ready to Elevate Your Business? If you’re interested, here are 3 ways I can help you right now:  1. Subscribe to our podcast | Looking to grow your business? Our weekly podcast is packed with the latest tips, tricks and strategies. Learn how to run a more efficient business and scale successfully – no fluff, just actionable and practical advice from someone who grew 3 multi-million $ businesses and exited successfully - Click Here to listen & subscribe now!  2. Download our free CEO Dashboard template that will help you build out your Business Plan & grow your business in a consistent and step by step manner – Click Here to download now. 3. Book a 20-minute Business Growth Call | Map out a growth plan for your business, uncover the #1 bottleneck that's holding you back right now and leave this call with a clear and actionable plan for what to do next in your business — Click Here CONNECT WITH JONATHAN HERPS Website: www.scaleupos.com LinkedIn: www.linkedin.com/in/jonathanherps Youtube: www.youtube.com/@jonathanherps Email: jonathan@scaleupos.com  🚀 Ready to Elevate Your Business? If you’re interested, here are 3 ways I can help you right now:  1. Subscribe to our podcast Get actionable strategies to run a more efficient business from someone who built & exited 3 multi-million $ companies. Click Here to listen & subscribe now!  2. Download our free CEO Dashboard template  Build a step-by-step business plan for consistent growth.  Click Here to download. 3. Book a 20-min Business Growth Call Map out a growth plan for your business and identify your biggest bottleneck & leave with a clear action plan. — Click Here

    CEO Playbook EP 24: Charting a Three-Year Vision - From Strategy to Execution

  8. 09/11/2025

    CEO Playbook Ep 23: Scaling Isn’t About More Tactics, It’s About This One Shift

    Scaling isn't about more tactics, it's about more clarity. It’s about giving your team a vision so clear they can act without waiting for your permission. In this episode of Stories of Scale, Jonathan Herps shares why your team doesn’t need more direction and why they need a crystal clear destination. You’ll learn how to build a 3 Year vision that aligns your people, removes daily chaos, and puts you back in the role of strategic leader. If you're a founder who’s still wearing all the hats, stuck in day-to-day chaos, and unsure how to move beyond the plateau, you need to hear this. Jonathan’s personal stories, client case studies, and frameworks will help you reclaim clarity, momentum, and your role as the true leader of your business. In this episode of Stories of Scale with Jonathan Herps, you’ll discover: Defining success beyond revenue (01:20)Why scaling requires more than strategy (02:49)Translating vision into a “leader’s intent” your team can act on (03:45)The military lesson every CEO can use to keep teams aligned (05:17)The power of a three-year vision (06:40)How one company leapt from #3 to market leader by rallying around a clear intent (07:23) Key takeaways for CEOs and business owners: Why “vision” isn’t enough if your team doesn’t know how to act on it.A three-year horizon is long enough to be transformational and short enough for your team to believe it’s possible.A clear “leader’s intent” keeps everyone aligned and empowered to act, even when plans change.Scaling a business isn’t just about strategy; it’s about clarity, leadership, and getting every person rowing in the same direction. Scaling isn’t about chasing endless tactics but about clarity, intent, and leading your people with purpose. When your team knows exactly where they’re going, growth stops being chaotic and starts becoming unstoppable. CONNECT WITH JONATHAN HERPS Website: www.scaleupos.com LinkedIn: www.linkedin.com/in/jonathanherps Youtube: www.youtube.com/@jonathanherps Email: jonathan@scaleupos.com  🚀 Ready to Elevate Your Business? If you’re interested, here are 3 ways I can help you right now:  1. Subscribe to our podcast Get actionable strategies to run a more efficient business from someone who built & exited 3 multi-million $ companies. Click Here to listen & subscribe now!  2. Download our free CEO Dashboard template  Build a step-by-step business plan for consistent growth.  Click Here to download. 3. Book a 20-min Business Growth Call Map out a growth plan for your business and identify your biggest bottleneck & leave with a clear action plan. — Click Here

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About

Honest conversations with the CEOs of growing private businesses: how they built it, what broke along the way, and what they'd do differently. I'm Jonathan Herps. I've spent 26 years as a CEO and 11 years coaching CEOs, and I've interviewed 133+ of them on this show. Every episode is a CEO telling the real story: the moment what got them here stopped working, the thing they held onto too long, the role they hired too late, and how they built a business that doesn't need them in every decision. Alongside the interviews you'll find The CEO Playbook, short teaching episodes where I share the tools I use with the CEOs I coach. If you're a founder or CEO growing a private business and want to learn from people who've been there, this show is for you. Website: www.scaleupos.comYouTube: www.youtube.com/@jonathanherpsLinkedIn: www.linkedin.com/in/jonathanherpsEmail: jonathan@scaleupos.com

Information

  • Creator
    Jonathan Herps
  • Years Active
    2025
  • Episodes
    162
  • Rating
    Explicit
  • Copyright
    © 2026 CEO Stories with Jonathan Herps
  • Show Website
    CEO Stories with Jonathan Herps