The Business Owner's Journey
We shorten the learning curve of business ownership by bringing on entrepreneurs, leaders, and innovators to share their stories, challenges, leadership practices, and winning strategies. Welcome to ‘The Business Owner’s Journey', the podcast that’s here to help you navigate your way in the world of business ownership. Hosted by 20+ year entrepreneur Nick Berry. Nick interviews entrepreneurs, leaders, and innovators to share their personal stories, challenges, leadership, and strategies from their own business owner’s journey. Guests like: Anne McGinty, Nick Nanton, Chase Murdock, Jessica Rhodes, Matt Diggity, John DiJulius, John Jantsch, Roland Gurney, Brett Bartholomew, Kiri Masters, Matt Goebel, Austin Mullins, Dr. Haley Perlus, Kelly Berry, Dana Farber, Steve McFarland, Sara Nay, Scott Fay, Daniel Wakefield, Jessica Yarmey, Shireen Hilal, Vivien Hudson, Anthony Milia, Romi Wallach and Nicole Mastrangelo. It’s crowdsourced business mentorship in highly concentrated doses. We’ll cover: - Strategy - Leadership - Ideas & Opportunities - Best practices - Tools and resources - All of the Lessons and experience from our guests This podcast for the business owners who are driven to grow and improve, + Who want realistic and actionable insights. + Who understand the immeasurable value in lessons learned from others. + And that they’re just one lightbulb moment away from a big breakthrough. The goal is to shorten your learning curve so you can get out in front of challenges and be prepared for opportunities. The journey for a business owner is hard. It’s complex, it’s stressful, and can be lonely. But it can also be exciting, rewarding, and fulfilling, and you don’t have to do it alone. Take advantage of insights and experiences of other business owners and how they’re navigating their own Business Owner’s Journeys, so you don't have to figure it all out on your own. Learn from businesses like Diggity Marketing, Duct Tape Marketing, Bobsled Marketing Agency, Treacle Marketing Agency, Moonstone Marketing, Vistage, EOS, John Maxwell Team, Life Intended, Top Tier Headshots, Milia Marketing, The Daily Drip #SmallBusiness #Entrepreneur #BusinessGrowth #SmallBiz #Startup #BusinessTips #BusinessLessons #BusinessOwner #OnlineBusiness #SmallBusinessOwner #BusinessMentor #BusinessCoach # BusinessMastermind #GrowthHacking #BusinessSuccess #BusinessLeadership #BusinessStrategy #MarketingStrategy
Episodes
Full Episode Page: John Barnes: Why Tax Advice Is Not Financial Advice for Business Owners
John Barnes is a Certified Financial Planner and the co-founder and CEO of Pendleton Street Business Advisors, an outsourced CFO firm built for entrepreneurs.
In this episode, John and host Nick Berry dig into financial planning for business owners: how growth can quietly build you an expensive prison, what to actually do with your business pro...
Full Episode Page: The Middle Is Gone: 5 Leadership Moves Top Experts Are Making in 2026
This is a solo episode of The Business Owner's Journey with host Nick Berry, pulling together insights from six Season 3 guests to map out the leadership moves expert business owners need to make right now.
Six months into 2026, AI handles average work and expertise is being commoditized faster than ever. The middle 60% of experts can't coast on ...
Full Episode Page: Shireen Hilal: AI, Trust and the Boutique Advantage in Professional Services Firm Growth
Shireen Hilal is the CEO and founder of Maior Strategic Consulting, where she advises professional services firms on how to grow.
Shireen returns for her third appearance on The Business Owner's Journey with Nick Berry. Shireen breaks down how AI is splitting expertise into commodity information and high-value judgment, why bou...
Full Episode Page: Katelyn Bourgoin: Buyer Psychology and the Ownable Idea That Grows an Expert Business
Katelyn Bourgoin is a buyer psychology expert and founder of Why We Buy.
In this episode, Katelyn joins host Nick Berry to explore how customer research, positioning, and a brainware business model help expert entrepreneurs outpace market shifts. She breaks down how to package a revelatory, ownable idea and turn research int...
Full Episode Page: Joe Gannon: AI, Authority and Personal Branding for Founders Who Have Something to Say
Joe Gannon is a personal brand strategist and founder of Amplify known for authority-driven content systems for top founders and creators.
Host Nick Berry and Joe cover the audience path vs leads path, AI's role in personal branding, and the StrateTree framework. Joe built content engines for Ali Abdaal, Chris Williamson, J...
Full Episode Page: Ryan Page: How a Financial Operating System Replaces Gut Decisions with Real Agency Profitability
Ryan Page is a CPA and founder of Backpocket CPA.
Host Nick Berry and Ryan Page dig into the Backpocket Operating System, a practical financial operating system for agency financial management. They cover fractional CFO for agencies vs. agency bookkeeping, a 90-day cash flow forecast, and why gross margin for agencies ...
Full Episode Page: Jay McCauley: Claude Cowork, Software for One, Ship Ugly, and Fractional Tech Partners
Jay McCauley is a fractional tech partner helping non-technical founders scale with confidence.
In this episode, Jay joins host Nick Berry to demystify Claude and AI tools for business owners while showing how a fractional tech partner helps founders buy back time. They unpack when to DIY with Claude Cowork or Claude Code versus ...
Full Episode Page: Jordan DiPietro: The 3H Leadership Framework and Why Every Founder Needs a Coach
Jordan DiPietro is a former CEO of Hampton and The Hustle and a founder coach advising CEOs scaling companies.
Host Nick Berry explores founder coaching and leadership with Jordan DiPietro. He explains his 3H Leadership Framework and Three Signals diagnostic self, team, model for scaling founder led companies without burnout. Dra...
Full Episode Page: Debbie Oster: Messaging Strategy, Marketing Leadership, and Agency
Debbie Oster is a messaging and marketing strategist who helps growth-stage B2B and service firms clarify audience and positioning.
Host Nick Berry and Debbie Oster unpack why many owners treat marketing like an execution problem instead of a leadership one. They explore how executive decision-making shapes messaging strategy, why a focused ideal cl...
Full Episode Page: Josh Fertel: Revenue Cycle Management That Drives Private Practice Growth
Josh Fertel is a healthcare revenue cycle management expert known for helping private practices grow.
In this conversation, Josh joins host Nick Berry to reveal how revenue cycle management is the engine of medical practice profitability. He breaks down common cash flow blind spots, practical billing fixes, and training that increases patient...
Full Episode Page: Paul Austin-Menear: Building Customer Feedback Systems That Fuel Innovation
Paul Austin-Menear is a business strategist and founder known for building customer feedback and innovation systems for purpose-driven entrepreneurs.
In this episode of The Business Owner’s Journey, host Nick Berry and Paul Austin-Menear explore how founder-led companies lose customer signal as they scale and how to build feed...
Full Episode Page: Natasha Walstra: Personal Branding and LinkedIn Strategies Designed for Trust
Natasha Walstra is a LinkedIn Strategist and Business Coach who empowers entrepreneurs and executives to turn genuine visibility into steady revenue.
Host Nick Berry talks with Natasha Walstra about LinkedIn strategy for business owners, covering personal branding, profile optimization, and social selling built on trust. Natasha explains ...
Full Episode Page: Jason Barnard: Brand Representation in AI for Founders, CEOs, and Entrepreneurs
Jason Barnard is an award-winning entrepreneur, author, innovator, and CEO and founder at Kalicube.
Host Nick Berry explains how brand representation in AI impacts digital due diligence, trust, and deal flow. Jason covers entity strategy, why inconsistent facts hurt referrals, and how digital brand intelligence trains Google and AI on y...
Full Episode Page: Jason Feifer: Building Adaptability in Business, Intentions Over Goals
Jason Feifer is editor in chief of Entrepreneur magazine and best-selling author of Build for Tomorrow.
Jason Feifer joins host Nick Berry to explain how business owners can build adaptability through intentions instead of rigid goals. They explore leadership flexibility, defining identity beyond job titles, transferable skills, and how to...
Full Episode Page: Dr. Benjamin Hardy: The Science of Scaling and Why 10x Changes Leadership
Dr. Benjamin Hardy is an organizational psychologist who leads business scaling programs for entrepreneurs, executives, and high-performing teams.
In this conversation, Dr. Hardy joins host Nick Berry to unpack the science of scaling and the 10x growth mindset. They explore how scale reframes strategy, exposes the founder bottleneck, and requ...
Full Episode Page: Anthony Trucks: Identity Shift, Dark Work, and Leadership Growth
Anthony Trucks is a former NFL athlete and entrepreneur known for his work on identity shift and personal transformation.
In this episode, Anthony joins host Nick Berry to explore why identity sets the ceiling on your goals. They break down why motivation fades, why mindset alone does not create lasting change, and how leadership identity determines w...
Full Episode Page: Season 3 Trailer: The Producer to Leader Shift
Nick Berry is an American entrepreneur, business advisor, and host of The Business Owner’s Journey.
In this Season 3 trailer, Nick explains why this season goes deeper than ever before into how successful business owners think.
The focus is the business owner mindset and the shift from producer to leader. Nick shares why leadership is the growth...
Full Episode Page: Nick Berry: The Five Stages of the Business Owner's Journey to Scale Your Business
A masterclass on the 5 Stages of the Business Owner’s Journey. He shows how to turn chaos into a focused business growth roadmap, build a sales engine and lead generation system for predictable revenue, and evolve from producer to leader using The Business Alignment System.
Find Out:
- How the Five Stages map becomes your busi...
Full Episode Page: Caitlin Johnson: Gamification Strategies for Business Leaders
Caitlin Johnson is a Master Certified Performance Coach and gamification specialist.
Nick Berry explores how Caitlin uses gamification in business to turn disengaged employees into high‑performing, purpose‑driven teams. From 90‑day “quests” to streaks and mulligans, Caitlin reveals a practical framework that simplifies strategy, sparks motiva...
Full Episode Page: Seth Donlin: How Storytelling Builds a Powerful Personal Brand
Seth Donlinis a marketing and communications coach and founder of Seth Donlin Coaching.
Personal branding is more than a logo; it is the story that convinces ideal clients you are their answer. In this fast‑moving conversation, host Nick Berry and Seth Donlin unpack why narrow messaging converts, how relatable anecdotes build instant trust, and when pod...
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