How to Scale a Business

In this episode of How to Scale a Business, host Hector Santiesteban sits down with Kurt Elster, the "unofficial mayor of Shopify," to uncover the secrets behind building a thriving e-commerce agency. Kurt shares his journey from a failed startup during the 2009 recession to becoming one of the most recognized Shopify experts in the world. He reveals the pivotal moments that transformed his business, including the power of specialization over being a generalist, the switch to fixed-price project pricing that eliminated client hesitation, and how he built recurring revenue streams to stabilize cash flow. Kurt also dives deep into his content marketing strategy through podcasting, the importance of case studies for service providers, and how AI tools are revolutionizing agency productivity—from transcription to coding. Business owners will learn actionable strategies for positioning their services, pricing with confidence, building a team with the right mix of contractors and full-time employees, and leveraging emerging technologies to scale faster. Kurt's advice on knowing your numbers and setting quantifiable goals provides a clear roadmap for anyone looking to break through their current revenue ceiling.Chapters:(00:00:00) - Introduction and Kurt's "Unofficial Mayor of Shopify" Title(00:01:42) - From Failed Startup to Service Provider: Kurt's Early Pivot(00:05:23) - The Power of Specialization: Why Kurt Chose Shopify(00:09:15) - Business Model Evolution: Fixed Pricing vs. Hourly Rates(00:12:48) - Building and Scaling a Team: Contractors vs. Full-Time Employees(00:18:30) - AI's Impact on E-commerce and Agency Work(00:23:45) - The Authenticity Problem with AI-Generated Content(00:26:12) - Working with Jay Leno's Garage and Big-Name Clients(00:27:18) - The Secret to Scaling: Know Your Numbers and Set Clear GoalsLinks and Resources:Kurt Elster's WebsiteThe Unofficial Shopify PodcastEthercycle - Kurt's AgencyAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Hector Santhe Esteban sits down with David Reske, CEO and founder of NowSpeed and author of "100X Entrepreneur," to explore the evolution of digital marketing and the cutting-edge strategies businesses need to scale in 2026. With 30 years in the industry—from building websites with Notepad in the 90s to pioneering Generative Engine Optimization (GEO) today—David shares invaluable insights on how marketing fundamentals remain unchanged while tactics evolve rapidly. He explains why AI search is replacing traditional SEO, how businesses can train Large Language Models (LLMs) to become their best sales representatives, and why most companies are missing massive opportunities by not optimizing for platforms like ChatGPT, which has 800 million monthly users. David breaks down the core principles of scaling a business, emphasizing the critical importance of product-market fit and efficient go-to-market strategies. He also reveals common misconceptions business owners have about digital marketing, the risks of not adapting to AI-powered search, and why companies have only months—not years—to get their GEO strategy in place. Whether you're a business owner looking to scale efficiently or a marketer trying to stay ahead of the curve, this episode delivers actionable frameworks and strategic insights you can implement immediately.Chapters:(00:00:00) - How a 30-Year Marketing Veteran Spotted the AI Revolution Before Everyone Else(00:01:00) - David's Journey: From the 90s Internet to Modern Digital Marketing(00:03:00) - What Hasn't Changed in Marketing After 30 Years(00:05:00) - Diagnosing Before Prescribing: The Strategic Approach to Marketing Audits(00:08:00) - Common Misconceptions Business Owners Have About Digital Marketing(00:11:00) - The Rising Knowledge Level of CMOs and CEOs in Digital Marketing(00:13:00) - How AI is Transforming Marketing Workflows and Efficiency(00:18:00) - Introduction to Generative Engine Optimization (GEO)(00:21:00) - The Sales Rep Analogy: Training AI to Represent Your Business(00:23:00) - GEO vs SEO: Questions Over Keywords(00:25:00) - Creating Content That Actually Answers Customer Questions(00:27:00) - The Timeline for Adapting to AI Search (Spoiler: You Have Months, Not Years)(00:29:00) - Where to Learn More About GEO and Connect with David(00:30:00) - The Secret to Scaling: Product-Market Fit and Efficient Go-to-Market StrategyLinks And Resources:WebsiteDavid Reske on LinkedInAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Hector sits down with Ty Crandall, founder of Credit Suite, to demystify business funding and credit. Ty shares his journey from building a 7-figure mortgage company to losing everything in the 2008 crisis, and how that experience led him to become an expert in business credit and alternative financing. He reveals why 60% of loan applications get denied before lenders even look at credit scores or revenue, and breaks down the exact steps any entrepreneur can take to build business credit without personal guarantees or credit checks. Ty explains how companies like Walmart and Apple strategically use other people's money (OPM) to scale, and how small business owners can apply the same principles. From starter vendors to fuel cards to universal credit cards, Ty outlines the complete roadmap to securing up to $1 million in business credit within a year. He also introduces Credit Suite's AI-powered Fund Smart tool that matches businesses with the right lenders based on their unique strengths. Whether you're a startup with no revenue or an established business looking to scale without risking personal assets, this episode provides the funding blueprint you need to remove capital barriers and grow your business.Chapters:(00:00:00) - Why Most Entrepreneurs Fail to Scale (And How to Fix It)(00:01:00) - Ty's Journey: From Seven Figures to Foreclosure(00:03:00) - The Biggest Misconception About Getting Business Funding(00:06:00) - How Big Companies Like Walmart and Apple Use Debt to Scale(00:09:00) - The #1 Reason 60% of Loan Applications Get Denied(00:13:00) - The Overwhelming World of Alternative Lending(00:15:00) - Success Story: From Homeless to 50-Truck Operation(00:18:00) - The Business Credit Blueprint: Step-by-Step Process(00:23:00) - AI-Powered Funding Matching and Fund Smart Tool(00:26:00) - The Secret to Scaling: Resilience Above AllLinks And Resources:WebsiteTy Crandall on LinkedInAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Mark Zweigher has spent 45 years in management consulting, built multiple Inc. 5000 companies, and analyzed over a thousand small businesses through his work as an entrepreneur, board member, and professor at the Walton College of Business. In this episode, Mark reveals the brutal truth about why most small businesses fail to scale—from the "word of mouth marketing" trap to family business dysfunction to the fundamental misunderstanding of what creates business value. He shares the exact $35 million mindset shift that transformed one client from a $27 million stagnant company to a $400 million enterprise, explains why buying existing businesses beats startups, and breaks down the management audit process he uses to diagnose business problems. Mark also discusses navigating current challenges like tariffs in his motorcycle manufacturing business, the critical importance of speed and 24/7 availability in modern business, and why marketing—not operations, not finance, not strategy—is the true secret to scaling. If you're tired of incremental growth and ready to build a business that's actually valuable on exit, this episode is packed with actionable insights from someone who's seen what works and what doesn't across decades and hundreds of companies.Chapters:(00:00:00) - Introduction and Mark's Background in Entrepreneurship(00:03:00) - Early Business Ventures: Bikes, Motorcycles, and Management Consulting(00:06:00) - Common Small Business Mistakes: Family Dysfunction, Poor Marketing, and Lack of Growth Commitment(00:09:00) - The $35 Million Mindset Shift: Growth Rate vs. Efficiency(00:12:00) - The Management Audit: Diagnostic Process for Business Improvement(00:17:00) - Timely Adjustments: AI, Keywords, and Being Discoverable(00:18:00) - Tariffs and Supply Chain Challenges in Motorcycle Manufacturing(00:20:00) - The Baby Boomer Exit Opportunity: Buying vs. Starting Businesses(00:23:00) - Speed and 24/7 Availability: The New Business Reality(00:26:00) - The Secret to Scaling: Marketing and Team BuildingLinks And Resources:WebsiteMark Zweig on LinkedInAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Hector Santisteban sits down with Keith Lucas, former Chief Product Officer and CTO at Roblox and author of "Impact," to explore the essential balance between high performance and creativity in scaling startups. Keith shares his journey from aerospace engineer to Silicon Valley leader, revealing how aligned autonomy and mission athletes create teams that innovate consistently. He discusses the transformative power of gratitude in leadership, the importance of aligning personal purpose with organizational goals, and practical strategies for accelerating time to market. Keith also tackles common startup mistakes like getting trapped in busy work instead of focusing on what truly matters, and explains how AI coding frameworks are revolutionizing product development speed. Throughout the conversation, he emphasizes that scaling isn't just about growth—it's about building a foundation of culture through clear values and hiring the right people who amplify your team's capabilities.Chapters:(00:00:00) - Keith's journey from aerospace engineer to Roblox CPO and startup advisor(00:02:34) - Why gratitude drives real business performance and team optimism(00:04:45) - Aligning personal purpose with organizational goals for breakthrough results(00:07:48) - From intense taskmaster to inspiring leader: Keith's transformation story(00:10:43) - Bridging high performance and creativity: the startup leader's challenge(00:13:12) - Three critical questions every scaling team must answer clearly(00:16:23) - Common startup mistakes: accelerating time to market and avoiding busy work(00:18:16) - The foundation of culture: vision, mission, and values that determine who stays(00:20:47) - How AI coding frameworks let small teams build 10x faster(00:23:15) - The secret to scaling: hiring mission athletes and defining behaviors that winLinks And Resources:WebsiteKeith Lucas on LinkedInAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Hector sits down with Gresham Harkless, founder of Blue 16 Media and a serial entrepreneur who discovered his calling at just 10 years old when he started a family newspaper. Gresham shares his journey from selling potato chips on the playground to building a digital marketing business, launching a franchise brokerage, and hosting multiple podcasts for entrepreneurs. He reveals why every business owner should think of themselves as a media company and how content creation is the common thread connecting all his ventures. The conversation dives deep into the evolving landscape of marketing, exploring how AI tools are removing barriers and enabling entrepreneurs to scale without working harder. Gresham discusses his framework for thinking differently about growth using concepts from "10X Is Easier Than 2X" and challenges conventional definitions of scaling by emphasizing time as the most valuable resource. He shares practical examples of how AI has transformed his business operations, from replacing $2,000/month contractor services with $20/month ChatGPT subscriptions to creating websites over a weekend that would have taken months. Throughout the discussion, Gresham emphasizes the importance of authenticity, storytelling, and the human element in business, arguing that technology should amplify rather than replace human connection. He encourages business owners to look back at their childhood passions to discover their true calling and to consistently share their stories across multiple platforms to build trust and reach their audience in today's noisy digital landscape.Chapters(00:00:00) - Everyone is a Media Company Now(00:01:00) - From Potato Chips to Building a Media Empire(00:03:00) - The Common Thread: Content as Your Superpower(00:05:00) - Why Storytelling Still Matters in Business(00:08:00) - Marketing Principles Stay the Same, Tools Change(00:10:00) - The Human Element: What Technology Can't Replace(00:13:00) - Why You Need to Say It 100 Times Before They Hear It(00:16:00) - AI and New Tech: Removing the Ceiling on What's Possible(00:19:00) - From $2,000/Month to $20/Month: Real AI Transformation(00:22:00) - Scaling Isn't Just About Revenue—It's About Time(00:25:00) - 10X Is Easier Than 2X: Thinking Differently About Growth(00:29:00) - The Secret to Scaling: Define What It Means to YouLinks And Resources:WebsiteGresham Harkless on LinkedInAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

In this episode, Nick Anderson shares his unconventional journey from high school dropout to banking executive to CEO of One Accord, a management consulting firm that's been helping businesses navigate transition and growth for 25 years. Nick reveals the #1 constraint killing most businesses—owner dependence—and explains how he's solving it in his own company using fractional executives. He breaks down the real order of operations for scaling: revenue first, then operations, then marketing. Nick candidly discusses the challenges of growing a business, from the loneliness of entrepreneurship to the fear of spending on marketing that might not work. He shares wisdom on why most aspiring entrepreneurs fail (no plan, wrong people, or lack of disciplined execution) and emphasizes that business is fundamentally about earning strangers' money by delivering value that exceeds what they pay. Whether you're a solopreneur trying to build a team or a growing company stuck at a revenue ceiling, Nick's practical insights on building systems, hiring fractionally, and focusing relentlessly on revenue will help you break through to the next level.Chapters:(00:00:00) - Welcome and Introduction to Nick Anderson(00:01:15) - From High School Dropout to 25 Years in Banking(00:03:15) - What One Accord Does: Leading Organizations Through Transition and Growth(00:05:45) - The Biggest Mistake Business Owners Make: Owner Dependence(00:08:30) - How Nick is Solving Key Person Risk with Fractional Executives(00:10:15) - The Scary Reality of Spending on Marketing That Doesn't Work(00:12:45) - The Order of Operations for Scaling: Revenue First, Always(00:16:30) - Why Most Businesses Don't Have a Revenue-First Mindset(00:19:15) - Business is About Earning Strangers' Money(00:22:30) - Where Aspiring Entrepreneurs Fail: No Plan, Wrong People, Lack of ExecutionLinks And Resources:WebsiteNick Anderson on LinkedInAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Sean Penrith, CEO of Gordian Knot Strategies, shares his journey from running a lucrative but unfulfilling business in South America to becoming a leader in climate finance. After sailing across the Atlantic and around Cape Horn, Sean returned home to pursue his MBA and started a glass recycling business that set him on a path toward purposeful work. Through founding nine different businesses, including a functional beverage company and a climate finance consultancy, Sean developed a powerful seven-element framework for predicting business success. This framework, born from research funded by the Walton Family Foundation, has proven remarkably accurate at identifying which projects and businesses will succeed or fail—regardless of industry or geography. Sean reveals why 70% of passionate entrepreneurs fail to identify willing and able payers for their solutions, how he maintains an 80% repeat client rate through trust in an AI-saturated world, and why he believes mindset and transforming limiting beliefs is the true secret to scaling a business. He also shares how he ran his businesses for three years from a sailboat during COVID and the counterintuitive career advice he gives his children about designing work around lifestyle rather than the other way around.Chapters:(00:00:00) - Sean explains the seven-element framework for predicting business success(00:01:31) - From South America hustler to purpose-driven entrepreneur(00:03:36) - How Sean started nine businesses by solving problems he actually had(00:06:00) - The research project that cracked the code on why startups fail(00:09:00) - Why 70% of entrepreneurs can't identify willing and able payers(00:14:00) - How AI is changing client relationships and the importance of trust(00:19:00) - Navigating polarized climate politics across different markets(00:21:00) - Why Sean reduced from nine service offerings to three core ones(00:22:00) - Career advice: Design your lifestyle first, then find work to support it(00:24:15) - The secret to scaling: Mindset over grindingLinks And Resources:WebsiteSean Penrith on LinkedInAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Katie Krispin, founder of Katie Krispin Law, reveals why estate planning isn't just for the wealthy or elderly—it's a critical business protection strategy that most entrepreneurs ignore until it's too late. Through real-world stories, including three young children who lost their mother without a plan, Katie explains how proper estate planning protects your business during incapacity (which affects 67% of people before death), avoids probate court delays of 12-18 months, and can save millions in taxes. She breaks down the difference between trusts and wills, debunks common misconceptions, and explains the four core documents every business owner needs: financial power of attorney, healthcare power of attorney, last will and testament, and revocable living trust. Katie emphasizes that estate planning is an ongoing process that should grow with your business, not a one-time event you handle at the end of life. She shares how recent tax law changes affect the $15M federal estate tax exemption and why starting the conversation now—even in 90-day sprints—can protect both your business and the people you love.Chapters:(00:00:00) - Introduction and overview of estate planning for business owners(00:02:15) - Why business owners struggle with long-term planning and the 90-day sprint mindset(00:04:45) - Estate planning as an ongoing process, not a one-time event(00:07:20) - The Sam Walton story: How early estate planning saved billions in taxes(00:09:10) - The tragic story of three young kids who lost their mom without an estate plan(00:12:30) - Common misconceptions: Trust vs Will explained(00:15:45) - Recent tax law changes and the $15M federal estate tax exemption(00:18:20) - The four core documents every business owner needs(00:21:40) - Incapacity planning: 67% of people become incapacitated before death(00:24:15) - How to get started: Education and taking actionLinks And Resources:WebsiteKatie Krispin on LinkedInAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!

Hector sits down with AI strategist Dan Cumberland to explore how businesses can effectively leverage AI beyond the hype. Dan introduces his POWER Framework for giving AI the context it needs—Person (persona), Others (audience), Work (output format), Expression (style), and References (examples)—and explains why most people get generic outputs. He shares real client success stories, including a consultant who reduced a 2-week hospital assessment report to just a couple of afternoons, and his own automated system for filtering hundreds of daily media opportunities down to 3-4 relevant ones. Dan addresses AI pitfalls like the "gaslighting" effect and emphasizes that domain expertise combined with good AI workflows creates an unstoppable combination, with key takeaways including brand voice training, specific workflows for repeated tasks, and understanding that AI excels at narrow, specific tasks rather than broad searches.Chapters:00:00:00 - Meet Dan Cumberland: From Fractional CMO to AI Implementation Expert00:01:00 - The Turning Point: Why Dan Pivoted His Entire Business Model to AI Strategy00:03:00 - Breaking Down the Black Box: How AI Tools Actually Think and Process Information00:04:00 - The POWER Framework Revealed: Your Blueprint for Getting Quality AI Outputs Every Time00:10:00 - Agentic Workflows Explained: How to Make AI Agents Work for Your Business (Not Against It)00:15:00 - The AI Gaslighting Problem: When Your AI Assistant Confidently Gives You Wrong Answers00:18:00 - Search vs AI: Why You're Using the Wrong Tool for the Job (And How to Fix It)00:20:00 - Real-World Marketing Wins: How Business Owners Are Using AI to Create Content That Converts00:23:00 - The 2-Week to 2-Afternoon Transformation: Advanced Workflows That Scale Your Client Deliverables00:26:00 - The Unfair Advantage: Why Domain Expertise + AI Workflows = Unstoppable Business GrowthLinks And Resources:Dan Cumberland's WebsiteAI Training GuideDan Cumberland on LinkedInAmplafy MediaHector Santiesteban on LinkedInHector Santiesteban on TwitterThanks so much for joining us this week. Want to subscribe to How to Scale a Business? Have some feedback you’d like to share? Connect with us on iTunes and leave us a review!