The Business Owner's Journey

The Business Owner's Journey

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The Business Owner's Journey episodes

  • Season 4 Preview: Who’s Coming and What We’re Getting Into | The Business Owner’s Journey

    Season 4 preview episode page on nickberry.info

    Season 4 of The Business Owner’s Journey starts Tuesday, November 3. In this short preview, Nick Berry walks through who is joining him this season and what the conversations are about.

    Who’s coming in Season 4:

    Jake George, co-founder and technical lead of Agentic Brain, on getting actual value from AI, starting with knowing when not to use it.

    Brett Farmiloe, CEO of Featured, the company that bought HARO, on getting your expertise heard.

    Mark Cole, CEO of Maxwell Leadership and John Maxwell’s successor, on developing leadership capacity in yourself and the people you lead.

    Brett Bartholomew, founder of Art of Coaching, on earning trust and influence when you already know your craft. His next book, The Antihero Advantage, comes out in December.

    Blake Erickson, co-founder of Scaling.com and business partner of Dr. Benjamin Hardy, on what separates businesses that are scaling from the ones that are just getting busier.

    Terry Rice, keynote speaker and AI trainer, on his Hard or Wrong framework for knowing when a challenge is worth sticking with.

    Plus more solo episodes from Nick, starting with one question every founder asks and almost nobody answers with a number: how much of your time should actually go to leading?

    This season is brought to you by Authority Coded, which helps experts improve what prospects find when they Google their name or ask AI about them.

    Follow the show wherever you listen so the first interview lands in your feed on November 3.

    · About Nick Berry
    · The 5 Stages of the Business Owner’s Journey
    · Nick Berry on LinkedIn

    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™, The Parallel Process™, and The 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, Authority Coded

    4 min
  • Daniel Wakefield: Personal Branding for Entrepreneurs and the Leap From Producer to Leader

    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)
    - The Parallel Process™


    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

    Does what prospects find when they Google you or ask AI about you match what they expected? That’s the Google-Me Moment.
    Authority Coded helps experts win it, so their research builds confidence in taking the next step.

    Learn more: https://authoritycoded.com

    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™, The Parallel Process™, and The 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, Authority Coded

    56 min
  • John Barnes: Why Tax Advice Is Not Financial Advice for Business Owners

    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
    - The Parallel Process™

    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

    Does what prospects find when they Google you or ask AI about you match what they expected? That’s the Google-Me Moment.
    Authority Coded helps experts win it, so their research builds confidence in taking the next step.

    Learn more: https://authoritycoded.com

    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™, The Parallel Process™, and The 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, Authority Coded

    40 min
  • The Middle Is Gone: 5 Leadership Moves Top Experts Are Making in 2026

    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
    • The Parallel Process™

    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™, The Parallel Process™, and The 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, Authority Coded

    18 min
  • Shireen Hilal: AI, Trust, and the Boutique Advantage in Professional Services Firm Growth

    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 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 for a small consulting team and why being cheap with good people has never built a great firm.

    You'll Hear:
    -
    Why almost no firm asks clients if the work was actually useful
    -How AI is splitting expertise into commodity vs. judgment work
    -Why boutique firms have a structural advantage right now
    -What "Swiss army knife" hiring means for small teams
    -Why best practices are a floor, and rarely a ceiling

    Links:
    -Maior Strategic Consulting
    -Shireen Hilal on LinkedIn

    Chapters 
    00:00 Introduction and Welcome Back 
    03:12 Why Firms Skip Client Feedback and What It Costs Them 
    10:45 How AI Is Splitting Expertise into Commodity or Judgment Work 
    18:30 Why Boutique and Mid-Market Firms Have a Real Window Right Now 
    26:15 Hiring for Small Business Growth: Swiss Army Knives and the Cost of Cheap Talent 
    34:00 Why Best Practices Make You Average 
    40:22 Final Thoughts and Wrap-Up

    Does what prospects find when they Google you or ask AI about you match what they expected? That’s the Google-Me Moment.
    Authority Coded helps experts win it, so their research builds confidence in taking the next step.

    Learn more: https://authoritycoded.com

    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™, The Parallel Process™, and The 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, Authority Coded

    34 min
  • Katelyn Bourgoin: Buyer Psychology and the Ownable Idea That Grows an Expert Business

    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 into messaging that converts. Katelyn also pressure-tests Nick's Parallel Process framework, showing how to sharpen a narrative buyers immediately understand and share. 

    You’ll Hear
    -How buyer psychology reveals shifts before competitors.
    -What makes an idea ownable and memorable.
    -When to replace courses with a brainware model.
    -How to turn research into revenue-driving messaging.
    -Best ways to position expert entrepreneurs to lead.
    -How to craft sticky, spreadable narratives.
    -Whether to co-create outcomes with clients.
    -Worst pitfall: isolating and echoing industry jargon.

    Links
    -Why We Buy by Katelyn Bourgoin
    -Be Unignorable
    -Katelyn on LinkedIn
    -Katelyn on X
    -YouTube: The Parallel Process™, the framework Katelyn workshopped at 21:21



    Chapters
    00:00 Katelyn Bourgoin's Entrepreneurial Journey
    03:32 Navigating Pivots and Failures
    05:38 The Future of Service-Based Businesses
    08:18 Building a Brainware Business Model
    10:52 Messaging Strategy for Consultants
    13:22 Positioning for Expert Entrepreneurs
    16:16 Finding and Framing an Ownable Idea
    18:46 Revelatory Messaging and Buyer Psychology
    21:21 Parallel Process and Expertise Business Growth
    24:02 The Evolution of Unignorable

    Does what prospects find when they Google you or ask AI about you match what they expected? That’s the Google-Me Moment.
    Authority Coded helps experts win it, so their research builds confidence in taking the next step.

    Learn more: https://authoritycoded.com

    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™, The Parallel Process™, and The 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, Authority Coded

    33 min
  • Joe Gannon: AI, Authority and Personal Branding for Founders Who Have Something to Say

    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, Jordan Peterson, Sahil Bloom, and Greg Isenberg. He breaks down how to map content to a buyer journey and build authority that converts. 

    You’ll Learn
    - Choose your path: audience or leads
    -Map content backward from the sale to earn trust
    -Win with bottom-of-funnel proof
    -Pick one platform and format using an effort-impact lens
    -Use AI to accelerate your voice

    Links
    -Joe Gannon’s Website
    -Joe on LinkedIn
    -Joe on YouTube
    -Amplify website

    Chapters
    00:00 Intro: Joe Gannon's personal brand client list
    02:30 Enthusiasm, results, and earning trust
    03:22 Engineering serendipity through personal branding
    06:40 Should every business owner build a personal brand?
    07:34 Audience path vs leads path for founders
    09:01 Aligning content strategy with business objectives
    12:43 AI and personal branding: the middle is gone
    17:54 The effort-impact matrix for content creation
    20:28 Why follower count is a misleading metric
    22:01 Leveraging AI for authority-driven content
    30:10 The StrateTree framework for founder positioning
    38:00 Bottom-of-funnel content and social proof

    Does what prospects find when they Google you or ask AI about you match what they expected? That’s the Google-Me Moment.
    Authority Coded helps experts win it, so their research builds confidence in taking the next step.

    Learn more: https://authoritycoded.com

    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™, The Parallel Process™, and The 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, Authority Coded

    46 min
  • Ryan Page: How a Financial Operating System Replaces Gut Decisions with Real Agency Profitability

    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 beats vanity metrics. How unit economics drive accountability, how financial clarity unlocks agency profitability, and when a fractional CFO vs bookkeeper makes sense.

    You’ll hear
    -Shift from gut calls to a financial operating system
    -Measure gross margin and set sustainable targets
    -Build a simple 90-day cash flow forecast
    -Know when to hire a fractional CFO vs bookkeeper
    -Push margin ownership to division leaders

    Links
    -Backpocket CPA
    -Free 90-day Cash Flow Forecast Template
    -Ryan Page on LinkedIn
    -Ryan Page on Instagram
    -Building Your Finance Strategy Team Guide

    Chapters
    01:21 Financial Clarity for Business Owners: A Mindset Shift
    04:07 The Financial Operating System Explained
    05:35 Why Gross Margin for Agencies Beats Top-Line Revenue
    08:40 Integrating Agency Bookkeeping into Operations
    12:11 Financial Ownership and Unit Economics for Agencies
    14:53 Common Agency Financial Management Pain Points
    16:02 Back Pocket Operating System Four-Step Framework
    18:50 Cash Flow Forecast and Fractional CFO Impact
    23:37 Overcoming "We're Not Ready"

    Does what prospects find when they Google you or ask AI about you match what they expected? That’s the Google-Me Moment.
    Authority Coded helps experts win it, so their research builds confidence in taking the next step.

    Learn more: https://authoritycoded.com

    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™, The Parallel Process™, and The 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, Authority Coded

    29 min
  • Jay McCauley: Claude Cowork, Software for One, Ship Ugly, and Fractional Tech Partners

    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 hiring help, why software for one beats bloated subscriptions, and how done-for-you vs done-with-you changes outcomes. Jay shares practical guardrails for automation, a simple rule for deciding when to call a pro, and the ship ugly mindset that prevents costly builds in a vacuum. If you want leverage without tech headaches, this is a pragmatic playbook for focus, speed, and impact.

    You’ll Hear
    -How to decide DIY with Claude or hire a pro
    -Why software for one slashes SaaS bloat
    -When to ship ugly and get fast feedback
    -How founders buy back time with a tech partner
    -Worst pitfall: building in a vacuum
    -When done-with-you beats done-for-you
    -What to automate first for quick wins

    Links
    -
    Jay McCauley’s Personal Website
    - Jay McCauley on LinkedIn
    - Watch the episode on Youtube

    Chapters
    00:00 What a Fractional Tech Partner Does for Non-Technical Founders
    02:58 Real Client Projects: AI Tools for Business Owners
    06:40 Why Ship Ugly Beats Building in a Vacuum
    09:58 Claude Cowork and Buying Back Time
    13:26 Software for One: Stop Overpaying for Tools
    15:42 Low-Hanging Fruit Wins with Claude Cowork
    18:17 Done-with-You: Empowering Founders Through AI Education

    Does what prospects find when they Google you or ask AI about you match what they expected? That’s the Google-Me Moment.
    Authority Coded helps experts win it, so their research builds confidence in taking the next step.

    Learn more: https://authoritycoded.com

    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™, The Parallel Process™, and The 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, Authority Coded

    24 min
  • Jordan DiPietro: The 3H Leadership Framework and Why Every Founder Needs a Coach

    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. Drawing on lessons from Motley Fool and HubSpot, Jordan shows how pattern recognition, hiring A players, and delegation help CEOs shift from grind to leverage.  

    You'll hear
    -How 3H unites high standards with real care
    -When to diagnose issues as self, team, or model
    -How to hire and keep A players 
    -How to delegate without losing quality
    -What pattern recognition saves in time and pain
    -How to prep a founder to CEO transition 

    Links
    - Jordan DiPietro Personal Website
    - Jordan on LinkedIn
    - Jordan on X
    - Signal // Noise newsletter


    Chapters
    03:46 Autonomy and Founder Burnout
    06:18 When to Make a CEO Transition
    08:37 Accountability and Self-Awareness for Founders
    11:29 Balancing Professional and Personal Goals
    14:00 Pattern Recognition in Business
    17:02 3 Signals Diagnostic for Founder-Led Companies
    22:02 The 3H Leadership Framework
    33:17 Why Every Founder Needs a Coach
    36:44 Founder Handoff and CEO Transition 

    Does what prospects find when they Google you or ask AI about you match what they expected? That’s the Google-Me Moment.
    Authority Coded helps experts win it, so their research builds confidence in taking the next step.

    Learn more: https://authoritycoded.com

    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™, The Parallel Process™, and The 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, Authority Coded

    41 min

About The Business Owner's Journey

From the publisher's feed

We shorten the learning curve of business ownership by bringing on entrepreneurs, leaders, and innovators to share their stories, challenges, leadership practices, and winning…