How to Scale a Business

Nat Berman has been building businesses online for over 20 years — from launching a website on Yahoo! GeoCities in 2001, to growing a portfolio of 25 niche websites organically, to building an engaged audience on LinkedIn and Instagram. In this episode, Nat sits down with Hector to break down the fundamentals that have never changed despite two decades of shifting platforms and technology: show up...

Most service-based businesses hit a growth wall when their messaging gets diluted—and they try to solve it by jumping straight to tactics. In this episode of How to Scale a Business , messaging strategist Stacy Eleczko (aka the “Queen of Clarity”) breaks down how to build positioning that actually differentiates you, how to use evidence (not assumptions) to understand what buyers care about, and h...

Tiyon Simpson shares how personal branding and positioning help entrepreneurs stand out in a market where AI makes it easy for businesses to look and sound the same. He explains why many teams overuse AI in a way that strips out creativity and human connection, and why audiences are increasingly hungry for authenticity. Tiyon breaks down what a brand really is, how to start with the why before the...

John Roman, CEO of BattleBox, breaks down how BattleBox went from a 2015 “outdoor gear subscription box” idea to a mature eight-figure business — including the early days of acquiring customers on Facebook for under $5, the hard (and expensive) lessons of running a cash-intensive subscription model, and the hire that changed everything: bringing in a true finance leader/CFO to fix cash flow and de...

Lauren Apple shares how CEO parents can scale a business without losing the very flexibility they set out to create. She walks through the “success trap,” why cookie-cutter advice breaks down when family responsibilities increase, and how to diagnose the real bottleneck instead of fixing symptoms. Lauren explains how intentional planning, clear boundaries, and built-in buffers protect energy and c...

Rob Haynie has spent more than three decades building a business in life settlements—an industry that, in Rob’s words, still hasn’t truly “started yet” because awareness is so low. In this episode, Rob breaks down the core growth lever behind his success: relentless education. He shares how his team survived multiple major market disruptions, why most professionals default to the wrong “option” fo...

Justin Michael shares a practical framework for combining spirituality, identity work, and disciplined action to drive real-world performance in sales, consulting, and business building. They unpack why titles, promises, and specificity matter in content, but quickly move into the deeper bottleneck: self-perception and identity. Justin explains why affirmations and vision boards often fail without...

Hector sits down with Jen Manswell, a revenue architecture expert who has helped identify over $110 million in pipeline opportunities throughout her career. Jen shares her journey from performing arts to corporate communications to demand generation, and how she discovered that most businesses—large and small—suffer from the same fundamental problem: they treat marketing as a cost center instead o...

Marcel Petitpas, co-founder and CEO of Parakeeto, reveals why most service-based businesses struggle with profitability—and it's not what you think. Drawing from his experience building multiple businesses across four industries, Marcel explains why profitability isn't a finance problem but an operations challenge. He shares the story of how one agency grew 45%, 60%, and then 90% year-over-year wh...

Hector sits down with leadership transition expert Estefany Marte, who took over her family business at just 20 years old and scaled it 8x in five years before a successful exit. Estefany reveals why 75% of mergers fail due to cultural clashes, the critical mistakes leaders make during transitions, and her framework for thriving through major business changes. She shares her "first 100 days" appro...

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 busine...

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 m...

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...

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 dysfunc...

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 tra...

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...

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...

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, inc...

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 affec...

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 co...

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 befo...

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, revealin...

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 o...

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...

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 s...