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 and business advisor 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: Dr Benjamin Hardy, Katelyn Bourgoin, Jordan DiPietro, Joe Gannon, Anthony Trucks, Jason Feifer, 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, Sara Nay, Scott Fay, Daniel Wakefield, Jess
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The Business Owner's Journey is a business podcast hosted by Nick Berry, with 84 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.
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Nick Berry hosts The Business Owner's Journey, a business show with 84 episodes published.
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Episode #84
Daniel Wakefield: Personal Branding for Entrepreneurs and the Leap From Producer to Leader
Jul 21, 202656 minS3
Full Episode Page: Daniel Wakefield: Personal Branding for Entrepreneurs and the Leap From Producer to Leader Daniel Wakefield is a photographer, entrepreneur, and founder of Top Tier Headshots. In this episode, host Nick Berry talks in person with Daniel to explore what happens when personal branding for entrepreneurs stops being an afterthought and becomes the business strategy. Daniel went from a $50 month to a $50,000 month as a solopreneur, then straight into three months of crickets. That crash forced a reckoning. Nick and Daniel walk through the founder mindset shift from producer to leader, whether recurring revenue is possible in project-based creative work, and the business transformation strategy that tripled Daniel's effective hourly rate. Anyone scaling a service business and feeling the ceiling will recognize this one. You'll hear: -How a photographer became a brand strategist by living his own advice -Why the business scaled faster than the leader, and what it cost -Whether recurring revenue is possible in a project-based creative business -How listening to client needs unlocked a retainer model -Why leadership is not a silo but the thing that trickles into everything -The worst way to price: guessing based on your own money story -How one positioned image landed a client a paid speaking engagement Where to Find Daniel: - Daniel Wakefield's Website - Daniel on LinkedIn - Daniel on Instagram - Top Tier Headshots Website - Top Tier Headshots on Instagram - Top Tier Headshots on LinkedIn - Top Tier Headshots on YouTube -Accelerate: How I Took My Creative Business from Zero to Six Figures in 12 Months (Amazon) Chapters 00:00 From a $60 Month to $50K: The Turning Point 01:27 Introduction: Meet Daniel Wakefield 02:06 From Headshots to Personal Brand Strategy 08:22 Why Clients Need More Than Great Photos 12:47 The Rise of Personal Branding for Founders 14:35 Building a Team and Becoming a CEO 16:35 The $50K Month That Nearly Broke the Business 20:00 Shiny Object Syndrome and Starting at Zero 23:20 Building a Growth Strategy Instead of Chasing Revenue 25:00 Raising Prices and Solving Bigger Problems 27:05 Is Recurring Revenue Possible for Creative Businesses? 29:35 The Shift From Producer to Leader 35:40 "Would You Like Me to Sign Those Handcuffs?" 39:20 Better Decisions Through Focus and Long-Term Thinking 41:15 Advice for Founders: Leadership, Branding, and Mentorship 45:00 The Future of Top Tier Headshots 49:35 Creating Brand Assets That Win Opportunities 52:00 Helping Clients See Themselves Differently Busy but not clear on what actually matters next? Get a free 90-Day Business Growth Roadmap to pinpoint your stage, identify the one priority that unlocks progress, and focus your next 90 days with confidence. Get it here: https://www.nickberry.info/roadmap New here? Meet Nick Berry: https://www.nickberry.info/about The Business Owner's Journey podcast is where entrepreneurs, leaders, and innovators join entrepreneur Nick Berry to share stories, challenges, and strategies from their journeys as business owners. Nick Berry is an entrepreneur and business advisor, known for creating the Business Alignment System™ and 5 Stages of the Business Owner’s Journey . He offers a (free) personalized 90-Day Business Growth Roadmap telling you exactly where you are today and what specific steps to take next. Official: NickBerry.info . tBOJ is hosted by Nick Berry, produced by Nick Berry, Kelly Berry & FCG . Sponsors: Redesigned.Business , FR , Entrepreneur's Edge
John Barnes: Why Tax Advice Is Not Financial Advice for Business Owners
Jul 7, 202639 minS3
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 profit, and why the CPA who keeps your taxes low is not the same person who's protecting your future. John explains how personal and business plans lock together like a zipper, why emergency and exit planning come down to two sheets of paper, and the sharp difference between a "correct" answer and the "right" one. This one gets practical, and a little uncomfortable in the best way. You'll hear: -How financial success can quietly turn a good business into an expensive prison -What to do with profit: whether to pay yourself, pay debt, or reinvest -How to link business and personal financial plans so both win -Whether you've done the emergency and exit planning that protects your family -Why tax advice is not financial advice, and how that trap costs owners later -Why we're drowning in "correct" answers but starving for the "right" ones Where to Find John: - Pendleton Street Business Advisor - John Barnes on LinkedIn Chapters 00:00 Outgrowing Early Success 01:39 Vanity Metrics vs Real Business Profit 04:02 Outsourced CFO: Business and Personal Financial Planning 08:39 Business Profit: Pay Yourself, Pay Debt, or Reinvest 13:09 Excavation and Spouse Alignment 15:50 Escaping Urgency Mode 21:20 Two Year Financial Planning 24:37 Emergency and Succession Planning 29:34 Correct vs Right Financial Advice 35:59 Why Tax Advice Is Not Financial Planning Busy but not clear on what actually matters next? Get a free 90-Day Business Growth Roadmap to pinpoint your stage, identify the one priority that unlocks progress, and focus your next 90 days with confidence. Get it here: https://www.nickberry.info/roadmap New here? Meet Nick Berry: https://www.nickberry.info/about The Business Owner's Journey podcast is where entrepreneurs, leaders, and innovators join entrepreneur Nick Berry to share stories, challenges, and strategies from their journeys as business owners. Nick Berry is an entrepreneur and business advisor, known for creating the Business Alignment System™ and 5 Stages of the Business Owner’s Journey . He offers a (free) personalized 90-Day Business Growth Roadmap telling you exactly where you are today and what specific steps to take next. 🟢 Official: NickBerry.info . tBOJ is hosted by Nick Berry, produced by Nick Berry, Kelly Berry & FCG . 🟢 Sponsors: Redesigned.Business , FR , Entrepreneur's Edge
The Middle Is Gone: 5 Leadership Moves Top Experts Are Making in 2026
Jun 23, 202618 minS3
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 credentials or effort anymore. Nick pulls clips from Joe Gannon, Dr. Benjamin Hardy, Katelyn Bourgoin, Natasha Walstra, Debbie Oster, and Jordan DiPietro to lay out five leadership moves for expert business owners. If your positioning, content, or value proposition sounds like something AI could generate, you're already invisible to the people who don't know you yet. You'll Hear -Why AI exposed the middle 60% of experts, not replaced them -How radical honesty unlocks every leadership move that follows -What an ownable idea is and why expertise alone won't cut it -Why most experts hide their trophies instead of showing up -How narrowing your audience opens more opportunity, not less -Why the best founders build support systems for harder calls Links - 5 Stages of the Business Owner's Journey - Five Ceilings for Expertise Businesses Featured Guests & Episodes - Joe Gannon Episode: AI, Authority and Personal Branding for Founders - Dr. Benjamin Hardy Episode: The Science of Scaling and Why 10x Changes Leadership - Katelyn Bourgoin Episode: Buyer Psychology and the Ownable Idea - Natasha Walstra Episode: Personal Branding and LinkedIn Strategies - Debbie Oster Episode: Messaging Strategy, Marketing Leadership, and Agency - Jordan DiPietro Episode: The 3H Leadership Framework Chapters 00:00 Mid-Year 2026 Business Recap 01:46 Joe Gannon: The Middle Is Gone and AI's Impact on Expert Businesses 02:36 Five Leadership Moves for Expert Business Owners 03:06 Dr. Benjamin Hardy: Tell Yourself the Truth 04:31 Why Working Harder Won't Move You Up 05:05 Katelyn Bourgoin: Build an Ownable Idea 09:37 Natasha Walstra: Stop Hiding and Stand Out as an Expert 11:07 Debbie Oster: Decide Who You Are Not For 14:13 Jordan DiPietro: Don't Go It Alone 17:25 One Shift, Five Moves, What's Next The Business Owner's Journey podcast is where entrepreneurs, leaders, and innovators join entrepreneur Nick Berry to share stories, challenges, and strategies from their journeys as business owners. Nick Berry is an entrepreneur and business advisor, known for creating the Business Alignment System™ and 5 Stages of the Business Owner’s Journey . He offers a (free) personalized 90-Day Business Growth Roadmap telling you exactly where you are today and what specific steps to take next. 🟢 Official: NickBerry.info . tBOJ is hosted by Nick Berry, produced by Nick Berry, Kelly Berry & FCG . 🟢 Sponsors: Redesigned.Business , FR , Entrepreneur's Edge
Shireen Hilal: AI, Trust, and the Boutique Advantage in Professional Services Firm Growth
Jun 2, 202634 minS3
<p><b>Full Episode Page:</b> Shireen Hilal: AI, Trust and the Boutique Advantage in Professional Services Firm Growth</p><p>Shireen Hilal is the CEO and founder of Maior Strategic Consulting, where she advises professional services firms on how to grow.</p><p>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 boutique and mid-market firms have a real window right now, and why chasing best practices gets you average results. She also gets into what hiring looks like...
Katelyn Bourgoin: Buyer Psychology and the Ownable Idea That Grows an Expert Business
May 19, 202633 minS3
<p><b>Full Episode Page:</b> Katelyn Bourgoin: Buyer Psychology and the Ownable Idea That Grows an Expert Business</p><p>Katelyn Bourgoin is a buyer psychology expert and founder of Why We Buy.</p><p>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 into messaging that converts. Katelyn also pressure-tests Nick's Parallel Process framework, showing how to sharpen a narrative buyers immediately understand and share. </p><p><b>You’ll H...
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