How to Scale a Business

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!

In this episode, Hector sits down with Jay Berkowitz, founder of the Ten Golden Rules and a digital marketing pioneer who's been in the internet space since before most people knew what Google was. Jay shares his journey from managing a $40 million ad budget at McDonald's to running a $60 million online diet company in the early 2000s, giving him unprecedented insights into internet marketing before it became mainstream. He reveals his Ten Golden Rules framework that's helped countless businesses scale, including why "there are no rules" is actually the first rule, how subscription models still dominate despite predictions of their death, and why the four P's of marketing remain fundamental even in the AI age. Jay breaks down the massive opportunity in YouTube (the second biggest website with 42 million daily views), explains why answering questions is the new SEO strategy for AI search optimization, and shares proprietary conversion technologies his agency has developed. He also discusses the importance of creating a unique value proposition, why you need to catch trends within the first six months before competitors pile in, and his personal "rule of three" for evaluating new marketing opportunities. Whether you're a service provider, attorney, or scaling any business, Jay's data-driven approach and real-world experience provide actionable strategies you can implement immediately.Chapters:(00:00:00) - From McDonald's $40M Budget to Internet Marketing Pioneer(00:03:42) - The First Golden Rule: There Are No Rules (Let Data Drive Decisions)(00:07:15) - Why Subscription Models and Email Lists Still Dominate in 2025(00:10:28) - How 1 Million YouTube Views Built Jay's Agency (Without Paid Ads)(00:13:51) - The Four P's of Marketing That Never Go Out of Style(00:17:36) - Answer Engine Optimization: The New SEO for AI Search(00:20:14) - Google's Secret Algorithm for Local Service Ads Revealed(00:23:47) - The Rule of Three: How to Catch Trends Before Competitors Pile In(00:26:29) - Run Your Business Like a Business: Systems, SOPs, and the E-MythLinks And Resources:Ten Golden RulesTen Golden Rules YouTube ChannelJay Berkowitz 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 Ryan Pereus, the Cold Call CEO, to explore how cold calling has evolved in 2025 and why it's still one of the most effective channels for B2B growth when done right. Ryan shares his journey from offering cold call scripts on Fiverr to building a premium outsourced SDR agency that's tested messaging across 100+ industries. He breaks down the Product Relevance Pyramid, revealing why some businesses struggle with cold calling not because of the channel itself, but because their offer is commoditized or poorly positioned. Ryan introduces the Four Elements of Cold Call Success—product relevance, target market accuracy, messaging strength, and SDR fit—and explains how each variable impacts campaign performance. He also dives into the three main objectives of every cold call: sparking genuine interest, selling the next step, and diffusing the salesperson stigma. Throughout the conversation, Ryan tackles common misconceptions about cold calling, discusses the impact of AI and iOS updates on outbound sales, and shares why quality appointments that actually show up matter more than vanity metrics. Whether you're scaling an in-house SDR team or considering outsourced cold calling, this episode is packed with tactical insights on messaging, positioning, and building trust from zero to one.Chapters:(00:00:00) - Why cold calling isn't dead—and how to make it work in 2025(00:01:42) - From Fiverr side hustle to building a cold calling empire(00:04:28) - The biggest mistakes killing your cold calling results (and how to fix them)(00:06:45) - The Product Relevance Pyramid: Why your offer matters more than your script(00:09:18) - What actually works in cold calling today (iOS updates, AI, and all)(00:13:42) - The 4 elements that determine cold call success—and which one you're missing(00:17:23) - The 3 objectives every cold call must hit to book quality appointments(00:20:15) - Can AI replace cold callers? Ryan's take on the future of outbound(00:23:47) - How to work with Ryan and access his cold calling frameworks(00:25:41) - The one secret that separates businesses that scale from those that stallLinks And Resources:WebsiteThe H2H MethodAmplafy 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!

Founders don’t scale by working harder; they scale by capturing the “essence” of the work locally, then documenting, delegating, and automating the repeatable parts with the right global talent. In this conversation, systems architect Patrick Doyle Brown explains how retention outperforms simple labor arbitrage, why automations need human oversight, how to map a customer journey before you spend on acquisition, and practical first wins like offloading social monitoring, inbox triage, and competitor price tracking into an AI-assisted loop. We cover region-by-strength role matching, the “first 100” rule for founders, and the mindset that keeps growth durable: don’t overspend, avoid shiny objects, always be selling.Chapters:(00:00:00) - Cold open and setup: why founders hit scaling bottlenecks(00:02:12) - Local first, then global: capturing the “essence” before you scale(00:06:45) - Retention over raw savings: compounding human capital(00:10:02) - Region strengths: sales, dev, ops, and hospitality by market(00:14:18) - Where to start: social management and inbox triage wins(00:18:40) - Market intel loop: competitor pricing + simple AI dashboards(00:22:55) - Automate vs. delegate: “trust, verify” and QA in the loop(00:27:31) - Customer journey map before ad spend(00:32:10) - Founder “first 100” rule and SOP handoff(00:36:48) - The scaling mindset: stay in lane, avoid shiny objects, always sellLinks And Resources:Patrick Brown on LinkedInWebsiteAmplafy 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!

Jake Wysocki, founder of Intention Craft, shares how design thinking, structured exercises, and tiny experiments help leaders scale by solving the right problems in the right order. We explore the Double Diamond framework, human‑centered research, constraints that spark creativity, and how to use AI to think better rather than outsource judgment. We close with Jake’s surprising “secret” to scaling: make it fun and make it human.- 00:00:00 – Intro: Jake's path to entrepreneurship- 00:03:55 – Talk to customers: research beats assumptions- 00:07:00 – Apply frameworks to every problem-solving stage- 00:07:58 – Double Diamond: problems first, solutions second- 00:09:44 – Find the problem that unlocks progress- 00:15:33 – Learn fast through tiny experiments- 00:17:30 – Sprint to create urgency and momentum- 00:18:44 – MVP mindset: scope down to learn- 00:22:24 – AI enhances human connection, not replacement- 00:32:14 – Scaling secret: make it fun, humanLinks And Resources:Jake’s crash course: https://course.intentioncraft.comAmplafy 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, host Hector Santiesteban sits down with bestselling author and founder of Sell Your Smarts, John Meese, to unpack the proven blueprint for scaling a wisdom-based business. John reveals why most entrepreneurs fall into the trap of “death by a thousand eBooks,” how to turn decades of experience into a profitable sold-out group coaching program, and why the real opportunity lies in shifting from information to insight in today’s digital age. Whether you’re a coach, consultant, or business owner ready to monetize your expertise, John’s insights will help you avoid burnout, build a resilient business model, and unlock scalable income without sacrificing your Saturdays.Chapters:00:00:00 – Welcome to How to Scale a Business Podcast00:01:06 – Mission is to steward wisdom by multiplying knowledge and experience.00:02:26 – Shift from blogging to group coaching.00:03:21 – Video game story shows frustration with starting over.00:05:05 – Wisdom only matters when solving real problems.00:05:41 – Wisdom is book smarts plus street smarts.00:08:49 – “Death by a thousand eBooks” causes burnout.00:10:28 – Start with high-ticket group coaching.00:12:00 – Group coaching added $100K in six months.00:13:30 – Model works across diverse niches.00:16:16 – Success comes from flagship, gateway, and subscriptions.00:19:42 – The age of information is over.00:22:45 – The age of insight has begun.00:23:46 – Free copy of Serve to Sell available.00:24:52 – Scaling requires empathy to stay connected to customers.Links And Resources:Sell Your Smart WebsiteServe to Sell by JohnAmplafy 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!

Nolan Bradbury, CPA and founder of Bradfield Accounting & Advisory, introduces his innovative Numbers for Freedom framework. He explores the disconnect between achieving financial goals and personal fulfillment, emphasizing a family-first approach to success. Nolan reveals the common pitfalls of traditional goal-setting and discusses how to align business objectives with personal values. He provides actionable steps for quantifying lifestyle costs, analyzing business finances, and fostering accountability to ensure growth serves a greater purpose.

In this episode of How to Scale a Business, host Hector Santiesteban talks with Justin Rashidi, co-founder of SeedX, about why he hires for “smart problem solvers” over experience and how that philosophy fuels growth. Justin explains why many companies that think they have a marketing issue are actually facing problems with data, sales integration, or margins, and how understanding core metrics like CAC, LTV, and gross margin reframes decisions as investments. He shares why rigid frameworks fail compared to a flexible tool-belt approach, how cutting the wrong activities can literally save millions, and why AI—though often misunderstood—is transforming processes. Ultimately, he highlights that a company’s growth is often limited not by its market, but by the adaptability of its leadershipChapters: 00:00:00 - Welcome to How to Scale a Business Podcast00:00:54 - What SeedX Does: Business Consulting for Marketing, Sales, and Tech 00:02:11 - The Real Reasons Companies Aren't Growing 00:04:05 - A "Tool Belt" vs. "Recipe" Approach to Consulting 00:04:47 - The Importance of Understanding Core Business Metrics 00:06:29 - The Emotional "Therapy" Aspect of Business Consulting 00:07:33 - Balancing Bespoke Strategy with Flexible Processes 00:08:51 - Key Metrics Owners Overlook: CAC, LTV, and Margins 00:12:47 - Is AI Overhyped or Underhyped? 00:14:13 - The Power of Tightly Scoped AI 00:16:01 - A Practical Approach: Using AI for Tasks You Don't Want to Do 00:17:59 - How Resistant Organizations Can Start with AI 00:19:30 - Advice for Early-Stage Scaling: Prepare for People and Operations 00:21:06 - Where to Find Justin Rashidi Online 00:21:58 - Leadership Self-TransformationLinks And Resources:SeedX WebsiteJustin on LinkedInJustin on InstagramJustin on Twitter/XAmplafy 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!