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 every day, focus on two or three critical tasks, and do it long enough to outlast everyone else. He shares why the phrase "this is how we've always done things" is one of the most dangerous sentences in...

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 how to create consistent messaging across your website, LinkedIn, referrals, and sales conversations so the right clients recognize you the moment they’re ready to buy.

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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 how, and how to use AI as a tool to accelerate strategy and execution without sacrificing craft. The conversation also covers the importance of community, real relationships, and client care...

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 decision-making. John also shares how the brand’s biggest growth inflection point came from a Netflix original show (Southern Survival) landing during the pandemic, why the company exited via a SPAC and later bought the business back when the...

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 create consistent margin, plus how outsourcing and modern AI tools can reduce household and operational load. The episode closes with a reminder to define what success actually looks like in the current season of life and to build rhythms that keep...

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” for clients, and how focusing on clarity, credibility, and distribution (even through AI-driven search behavior) can scale any business. If you’re a founder, operator, or sales leader trying to grow in a market where your buyer...

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 “being” work, how service and ROI create sustainable abundance, and how to balance faith with inspired action. The conversation covers flow versus grinding, the 80/20 principle in effort and results, and the importance of reading and writing as a way to build independent thinking in an AI-s...

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 of a revenue engine. She reveals the biggest pitfalls that keep companies stuck in feast-and-famine cycles, including over-reliance on referrals, failure to systematize processes, and getting so busy doing the work that they forget to talk about it. Jen walks thro...

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 while tripling profitability and reducing team burnout, all through better visibility into their business model. Marcel breaks down the critical difference between compliance accounting and management accounting, why most agencies are "planning to fail" without realizing it, and how expectations versus reality create the in...

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" approach to leadership transitions, explains why leaders must scale themselves before their business can scale, and discusses how to navigate the emotional rollercoaster that comes with acquisitions, successions, and rapid growth. Whether you're considering an acquisition, planning a...

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...

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 n...

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...

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 br...

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...

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...

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 shar...

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...

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 po...

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 emph...

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...

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, ta...

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...

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...

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 m...

In this episode of How to Scale a Business, host Hector Santiesteban sits down with Nolan Bradbury founder of Bradfield Accounting & Advisory to uncover why so many entrepreneurs achieve their financial targets but still feel unfulfilled. Nolan introduces his Numbers for Freedom Framework, a practical system that helps business owners align their finances with the life they truly want. From the dangers of chasing the wrong goals to reorienting your business around freedom, Nolan shares actionable insights on scaling smarter, creating clarity, and avoiding the traps of growth that don’t serve you.

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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 trans...

Hector Santiesteban talks with Wilson Zehr, CEO of Cendix and Zairmail, about his career as a serial entrepreneur. Wilson shares his journey from software engineer to entrepreneur, driven by a desire for more control over the direction of his career. He discusses how he navigated challenges like the triple whammy of the dot-com meltdown, 9/11, and the anthrax scare. Wilson explains how his company's responsible financial management during these contractions allowed them to acquire their largest competitor. He also offers his perspective on AI, calling it an enabling technology rather than a single disruptive application. Finally, he reveals his secret...

In this episode of How to Scale a Business, Brianna Greenspan—author, genetics consultant, and CEO of Brianna Greenspan International—reveals how scaling with heart, integrity, and intentionality creates sustainable success. Born with a chronic illness and shaped by adversity, Brianna shares how self-leadership, conscious reflection, and asking the right questions became her ultimate growth tools. She discusses the real science behind wellness, how she “fails fast and pivots faster,” and why traditional hustle culture often leads to burnout. From skipping pop culture to leading a wellness village in a Las Vegas casino, Brianna brings a bold, evidence-based approach to growt...

Scaling a remote business isn’t just about growth—it’s about creating operational clarity and building systems that don’t depend on the founder. In this episode, Hector sits down with operations strategist Madi Waggoner to unpack the L.I.F.T. Framework, a powerful four-part system focused on Leadership, Infrastructure, Fuel, and Team. Madi shares real-world tactics for overcoming founder bottlenecks, setting up trust-building weekly reports, and using tools like Slack and Asana the right way. If you’ve been “driving blind” without KPIs or overwhelmed by constant communication breakdowns, this episode offers a practical roadmap to scale with cla...

Eric Collett — CEO of A Mind For All Seasons — reveals how entrepreneurs can upgrade their operating system by mastering brain health fundamentals. Drawing on decades of experience reversing cognitive decline, Eric unpacks why your brain is your tool in the knowledge economy and how sleep, stress management, nutrition, and cognitive training sharpen your thinking like a hardware upgrade. Discover why neuroplasticity is your secret edge, what myths are sabotaging your performance, and how to scale smarter with a sharper mind.

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In this episode of How to Scale a Business, Dr. Lani Jones—clinical psychologist, executive advisor, and founder of HBL Advisory Group—joins host Hector Santiesteban to explore how internal growth fuels scalable success. Drawing from her transition out of corporate healthcare and into entrepreneurship, Dr. Jones unpacks the powerful role of emotional intelligence, communication, and self-leadership in building high-performing teams. She challenges the notion that employee wellness is just “corporate fluff” by showing its direct impact on retention, productivity, and profitability. Whether you’re leading a small team or scaling a growing company, this conversation reveals how investing in yoursel...

Hector sits down with Cassie Shea, a somatic business coach who helps high-performing founders collapse time and expand their businesses by re-engineering the one thing most people overlook: identity. Instead of leading with tactics, Cassie shares why scaling sustainably demands a transformation from within. She explains how heartache, burnout, and boredom are often signs that a founder’s identity story is misaligned with their next level. Whether you’re a $500K founder stuck in overwhelm or a $2M CEO looking for more presence and fulfillment, this episode dives deep into the inner architecture of success. Plus, Cassie reveals how she’...

Hector sits down with Jon Logan, founder of Green Lit Growth Strategies, to unpack what’s really stopping small businesses from scaling. With a diverse background in food service, cybersecurity, and full-scale marketing, Jonathan shares how he grew a company from $3M to $25M using his proprietary G.R.O.W.T.H. Framework. He reveals why most brands “talk about themselves backwards,” how to build emotional resonance, and what it takes to create a “marketing machine” that scales. Learn the power of positioning, community-building, and nurturing relationships for real bottom-line growth.

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Wes Chyrchel—fractional COO, consultant, and author—joins Hector to unpack the real operational backbone behind successful scaling. With over 27 years of experience turning vision into execution, Wes breaks down how founders can escape the chaos of doing it all and move into their zone of genius. From crafting goal-driven strategies to choosing the right KPIs and daily actions, Wes reveals how small, consistent reps—just like in fitness—build scalable, sustainable companies. He also explores how AI is reshaping organizational structure and why creating multiple income streams is no longer optional. Whether you're a startup founder stuck in the weed...

Laura Humphreys shares the unfiltered journey of building—and selling—a $15 million agency, only after nearly burning out in the process. Now a mentor to agencies worldwide, Laura unpacks the seven strategies she teaches to help owner-operators escape the hamster wheel, reclaim their time, and create scalable, high-performance businesses. From using AI to future-proof service delivery to building deep sea sales pipelines, this episode is packed with both war stories and winning tactics for founders who are ready to lead like CEOs.

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Hector sits down with Aaron Reiter, Managing Partner at InterProse, to challenge everything you thought you knew about debt collection. With a background in communication, sales, and psychology, Aaron shares how he unexpectedly found purpose in an industry often overlooked—or even misunderstood. Discover how InterProse uses education, technology, and empathy to support family-owned businesses and drive revenue recovery without compromising integrity. If you're looking for hidden profit levers in your business, or ways to scale with compassion, this conversation is one you won’t want to miss.

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Hector Santiesteban sits down with Kash Fadaie, founder of Fadaie Insurance Services, to explore how an internal spiritual awakening transformed into a thriving business. Kash shares how escaping Iran as a child, diving into sacred texts, and seeking divine alignment laid the foundation for scaling a purpose-driven insurance company. If you’ve ever felt called to grow a business without losing your soul, this conversation will resonate deeply.

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In this episode of How to Scale a Business, host Hector Santiesteban is joined by Kurt Schmidt, an agency business coach, Inc. 5000 leader, and former extreme sports pro. Together, they dive deep into the highs and lows of growing a service-based business. From the profitable "sweet spot" of 6–12 employees to the leadership transitions that trip up creatives-turned-CEOs, Kurt shares real talk and real strategies for scaling sustainably. If you're running an agency, creative studio, or service-driven company — this is an episode you can't afford to miss.

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Chad Harrison—head of franchise development at Authority Brands—shares how scalable businesses are built through proven systems, strong leadership, and the power of franchising. From supporting new owners in the “number two business” (Doody Calls) to guiding semi-absentee entrepreneurs, Chad breaks down how following a playbook and leveraging a support network can turn even unconventional opportunities into serious success. Whether you’re exploring business ownership or looking to grow your existing operation, this episode offers practical insights on leadership, systems, and scaling the right way.

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