Wisdom Journey

Wisdom

Follow my unfiltered, real-time journey as I navigate the world of online income. No fake success stories or get-rich-quick schemes – just honest documentation of wins, losses, and everything in between. Each episode captures my weekly experiments with different online business models: freelancing, digital products, affiliate marketing, and more. I share exact numbers, strategies that worked (and failed), and the brutal reality of building income Want to be a guest on Wisdom Journey? Send Wisdom Okonkwo a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/wisdom

  1. 3D AGO

    How to Build a Human-First Business Culture – Dylan Bost |Ep 96

    Hey friends, it’s Wisdom here! In this episode, I sat down with Dylan Bost, founder of SunnyHQ, to get real about what it means to build a business that actually gives you your life back—not just drains you. We talked candidly about Dylan’s journey from running a successful agency that looked amazing on the outside but left him feeling empty, to reshaping everything with a human-first approach. Dylan shared the tough lessons he learned about burnout, what truly matters when designing your systems, and why chasing endless leads isn’t always the answer. If you’ve ever felt stuck in “reactive mode” or wondered how to align your work with your life, this episode is for you. My hope is that you walk away inspired to prioritize what matters most and give yourself permission to step back, reflect, and breathe. Thanks for joining us on the journey! Connect With Dylan Bost Website : https://dylanclaytonbost.com/ LinkedIn: https://www.linkedin.com/in/dylanbost/ Instagram: https://www.instagram.com/dylanclaytonbost/ Twitter:https://x.com/dylancbost I’m building an online business in public — sharing every win, setback, and “I can’t believe that happened” moment along the way. If you’ve ever wondered what it really looks like to start from scratch, come along for the ride. Join the journey at [https://wisdom.beehiiv.com/](https://wisdom.beehiiv.com/) Chapters 00:00 Introduction and Guest Welcome 00:34 Life Before Sunny HQ and Early Success 01:13 Behind the Scenes: Struggles and Reflections 05:13 Facing Fear and Consequences of Avoidance 06:37 Building Sunny HQ: Choosing a New Path 08:36 Designing Energizing Systems 12:16 Leads vs. Conversion: The Real Business Problem 17:16 Operational Mistakes Slowing Growth 19:21 Blending Creative and Technical Leadership 22:37 Reflection, Memory, and Leadership Growth 25:01 Foundational Shift for Stressed Founders 26:31 What's Next: The Seven Mirrors and Future Plans 28:01 Where to Connect & Closing Remarks

    29 min

  2. FEB 18

    How to Avoid Vanity Metrics and Focus on What Matters – Kuber Jain | Ep 95

    Hey friends, Wisdom here. Today on Wisdom Journey, I sat down with the brilliant Kuber Jain, senior data scientist at Headspace, to unpack how data really drives decisions that matter. We talked about why data isn’t just about crunching numbers—it’s about shaping strategy, avoiding vanity metrics, and making clear choices that push your business forward. Kuber shared stories from DocuSign and Headspace, revealing how he builds frameworks that cut through dashboard clutter and focus teams on what truly moves the needle. We also dove into retention, personalization, and balancing intuition with analytics. My hope is that you walk away inspired to use data as a tool for clarity—not just for tracking, but for action. If you want more practical tips and behind-the-scenes insights, don’t forget to join the newsletter. Let’s keep building smarter, together! Connect with Kuber Jain LinkedIn:https://www.linkedin.com/in/kuberjain/ I’m building an online business in public — sharing every win, setback, and “I can’t believe that happened” moment along the way. If you’ve ever wondered what it really looks like to start from scratch, come along for the ride. Join the journey at https://wisdom.beehiiv.com/ Chapters 00:00 Introduction and Guest Welcome00:53 The Role of Data in Decision-Making01:13 Early Misunderstandings About Data Analytics03:48 Data-Informed Teams vs. Dashboard Collectors07:00 Why Teams Love Dashboards Over Action09:17 Spotting Vanity Metrics and Their Risks10:52 Using Decision Trees to Find Meaningful Metrics12:27 Signals That Matter When Joining a New Company14:17 Filtering Signal from Noise in Large Datasets16:45 Questions to Ask Before Diving into Data19:36 When Correct Data Leads to Wrong Decisions22:02 Communicating Data Insights to Non-Technical Leaders23:50 The Cost of Delaying Decisions for More Data25:21 Retention: Input vs. Output Misconceptions26:33 Acquisition vs. Retention Focus in Companies29:41 Balancing Personalization at Scale31:31 Deciding Between Data and Intuition32:48 What Breaks Down in Cross-Functional Data Teams34:13 How Impact Is Defined in a Data Career35:50 Practical Steps for Better Data Decisions37:25 How to Connect with Kuber Jain37:48 Episode Wrap-Up and Listener Takeaways

    38 min

  3. FEB 2

    How to Protect Your Assets from Lawsuits and Probate – Matthew Meredith | Ep 94

    Hey friends, it’s Wisdom here! In this episode, I sat down with asset protection and wealth strategist Matthew Meredith to talk about something we all think about: not just building wealth but making sure it truly lasts. We dove into real stories where families lost everything—not from bad investments, but from poor planning or unexpected lawsuits. Matthew Meredith unpacked practical strategies about protecting your assets, forming the right companies, and why trusts aren’t just for the super-rich. Most importantly, we talked about taking small steps now to avoid heartbreaking mistakes down the road. My hope is that after listening, you’ll feel empowered to start safeguarding what you’re working so hard to build—even if you don’t think you have “enough” yet. The journey is about more than collecting coins; it’s about enjoying life and leaving a legacy. Let’s grow smarter together! Connect With Matthew MeredithWebsite:https://meridianlg.com/ LinkedIn:https://www.linkedin.com/in/matthewrmeredith/ I’m building an online business in public — sharing every win, setback, and “I can’t believe that happened” moment along the way. If you’ve ever wondered what it really looks like to start from scratch, come along for the ride. Join the journey at https://wisdom.beehiiv.com/ Chapters 00:00 Welcome to Wisdom Journey & Guest Introduction00:55 Matthew Meredith’s Journey to Wealth Strategy04:11 The Cost of Poor Planning: A Story05:06 Beginning Asset Protection: Simple Solutions06:28 Misunderstandings About Generational Wealth08:30 Silent Threats to Wealth and The One Stop Shop Approach11:06 How People Approach Protecting Their Legacy13:33 Client Breakthroughs and Business Success Stories15:45 The Cost Concern: Is Asset Protection Expensive?18:24 Looking 10–50 Years Ahead: Planning for Change22:52 Practical Steps to Start Safeguarding Assets26:32 Philosophy on Money: The Zelda Analogy28:21 What Wealth That Lasts Really Means29:26 Where to Find More About Matthew & Meridian Legal Advisors30:12 Outro & Final Wisdom

    31 min

  4. JAN 14

    How to Use AI to Streamline Your Hiring Process — Sean Griffith | Ep 93

    Hey friends, it’s Wisdom here! In this episode, I sat down with Sean Griffith—someone who’s gone from corporate high-flyer to building his own AI-powered hiring platform, Truffle. We dug into the real story behind scaling SaaS businesses (from $1M up to $40M ARR!), why work-life balance isn’t a myth, and how to recognize those early signals that it’s time to hire for your team. Sean didn’t hold back on sharing the hard truths about leadership, hiring pitfalls, and the game-changing ways AI can help small business owners work smarter, not harder. My hope? That you walk away knowing it’s okay to prioritize what matters—your time, your team, and building meaningful work. And hey, if hiring has been a headache, you’ll want to hear Sean’s advice for making it a whole lot easier. Let’s keep leveling up together! Connect with Sean Griffith Website:https://www.linkedin.com/in/griffithsean/ LinkedIn:https://ca.linkedin.com/in/griffithsean I’m building an online business in public — sharing every win, setback, and “I can’t believe that happened” moment along the way. If you’ve ever wondered what it really looks like to start from scratch, come along for the ride. Join the journey at https://wisdom.beehiiv.com/ Chapters 00:00 Welcome to Wisdom Journey & Guest Introduction00:25 Sean Griffin’s Entrepreneurial Spectrum01:34 Reflecting on the Traits Connecting Each Chapter02:49 The Moment That Sparked a Career Shift04:43 Misconceptions About SaaS Executives06:23 What Scale Really Feels Like Inside a SaaS Company08:08 Differences Between Building $1M vs $40M Businesses10:02 Early Signs It’s Time to Hire for Small Teams12:34 Deciding Your First Key Hire as an Online Entrepreneur15:26 The Power and Limits of Leverage in Business Growth17:07 Common Hiring Mistakes Small Businesses Make20:21 The Founder’s Role in the Hiring Process21:26 What Separates Teams That Grow Fast from Those That Stall23:27 What Is Truffle and How It Transforms Hiring25:52 The Evolving Role of AI in Hiring29:53 The Future of AI in Talent Decisions31:09 Human Qualities AI Can’t Replace in Leadership33:42 How Role Changes Shaped Sean’s Entrepreneurial Journey35:29 Shortcut Advice for Your First Hire37:02 Is Truffle for Small Business or Just Big Companies?38:13 How Fast Can You Implement and Use Truffle?40:10 The Real Value of Defining Roles and Using Truffle41:39 Beyond Hiring—How AI Is Helping Small Businesses44:24 Sean’s Definition of Meaningful Work45:39 Where to Find Sean Griffin and Try Truffle46:26 Podcast Wrap-Up and Closing Remarks

    47 min

  5. 12/20/2025

    How to Transition from Tech to a Creative Career – Katharina Huang | Ep 92

    Hey friends, it's Wisdom here! In today’s episode, I sat down with Katharina Huang—author, traveler, and creator of the Veg Out Voyage Puzzle book series. We dove deep into her bold journey from Silicon Valley data scientist to self-employed creative, and how life changes (like her father’s stroke) reshaped her priorities. Katharina shared the real costs and fears of leaving the 9-to-5, the joy of designing a life around puzzles and travel, and the rollercoaster ride of self-publishing and online business. What I really hope you take away: it’s okay to pivot, to build something truly yours from scratch, and that mistakes are part of the process. Your path doesn’t have to look like anyone else’s—you can find momentum and meaning in ways that surprise you. Thanks for listening, and keep walking your own wisdom journey! Connect with Katharina Huang Website:https://vegoutvoyage.com/ I’m building an online business in public — sharing every win, setback, and “I can’t believe that happened” moment along the way. If you’ve ever wondered what it really looks like to start from scratch, come along for the ride. Join the journey at https://wisdom.beehiiv.com/ Chapters 00:00 Introduction and Katharina's Background 01:33 Life in Silicon Valley and Career Path 04:22 Burnout and Realizations Post-Pandemic 07:21 Deciding to Leave Tech 09:33 Family and Friends’ Reactions 10:37 Impact of Her Father’s Stroke 17:51 Life After Quitting: Plans and Self-Care 19:46 Creating Travel Puzzle Game Books 22:03 Lessons from Self-Publishing 24:22 Tech Skills: Data Science Meets E-commerce 26:32 Platform Choices: WordPress vs Shopify 29:29 Overcoming Challenges of Solopreneurship 33:24 Explaining Her Work for All Ages 35:34 Surprises as a Solo Creator 37:41 Marketing Insights and Social Media 40:30 Newsletter and Building Community 43:10 Practical Newsletter and Sales Tips 44:39 Measuring Website Traffic and Ads 46:41 Podcasting and Audience Building 47:46 Closing Thoughts and How to Connect

    49 min

  6. 12/19/2025

    How to Build Shame-Free Wellness Into Your Work Routine – Dr. Portia Preston | Ep 91

    Hey friends, it’s Wisdom here! Today I sat down with the amazing Dr. Portia Preston to get real about what happens when hustle culture starts costing us more than it gives. We dug into her journey—how burnout and chronic illness forced her to rethink what success should actually look like, and the powerful concept of “shame free wellness.” We talked about why it’s so hard to let go of the “shoulds” society plants in our heads, how the SANE cycle can help us check in with ourselves, and why thriving means learning to integrate both struggle and rest into our lives. If you’ve ever felt guilty for taking a break, or wondered how to balance ambition with being kind to yourself, this episode’s for you. My hope is you walk away knowing your worth isn’t tied to your output—and that it’s absolutely okay to rest. Connect with Dr Portia Preston Website:https://portiapreston.com/ LinkedIn:https://www.linkedin.com/in/portiapreston/ I’m building an online business in public — sharing every win, setback, and “I can’t believe that happened” moment along the way. If you’ve ever wondered what it really looks like to start from scratch, come along for the ride. Join the journey at https://wisdom.beehiiv.com/ Chapters 00:00 Introduction and Guest Welcome01:14 The Cost of Hustle: Dr. Portia Preston’s Story02:06 Success and Chronic Illness: Personal Impact03:19 Stress, Shame, and Wellness in Professional Life04:06 Defining Shame-Free Wellness05:11 Why Shame Gets Attached to Wellness06:11 The “Shoulds” Behind Hustle Culture07:15 Tying Worth to Output: Entrepreneur Perspectives08:16 Longevity vs. Short-Term Hustle09:11 Rewriting the Cultural Narrative Around Grind10:29 Growing Up Hustling: Culture and Survival10:39 The SANE Cycle: Inspiration and Purpose11:05 The SANE Cycle: Four Steps Explained12:47 Real-Life Example of SANE Cycle in Action14:17 Normalizing Rest and Cultural Reflections15:10 Wisdom Okonkwo: Hustle & Rest in His Culture17:01 Imposed Hustle and the Shame Narrative18:31 Getting Stuck: Insanity vs. Change19:15 Accepting Reality and Context19:36 The Power of Asking “Why”20:17 Why Medicine? Prestige and True Motivation23:19 Helping People Beyond Labels and Careers24:47 Wellness, Identity, and Shared Humanity25:20 Understanding Flow: Sustainable Practices26:35 Balancing Work, Deadlines, and Flow28:07 Messy Lives and Authenticity: Behind the Scenes29:50 Building Your Life or Your Job30:49 Prioritizing Well-Being Over Achievements32:24 Letting Go: Protecting Peace33:24 Struggles, Stigma, and Representation34:45 Suffering vs. Struggling: No Award for Pain36:42 Learned Helplessness and Mindset37:47 Living with AuDHD: Work and Leadership40:50 Thriving Through Integration42:13 Burnout: Where to Start—Hustle, Flow, or Let Go?44:03 Burnout Beyond Work: Systems and Survival46:36 Final Thoughts on Ambition and Wellness47:41 Book Details, Resources, and How to Connect48:55 Closing Remarks and Next Steps

    49 min

  7. 12/18/2025

    How to Network Like a Pro Using Your Podcast – Pete A. Turner | Ep 90

    Hey friends, it’s Wisdom here! In this episode, I had the absolute pleasure of sitting down with Pete A. Turner—a former combat spy turned powerhouse podcaster and media leader. We kept it real about what it actually takes to succeed in this online business world, from building trust and mastering communication to the not-so-glamorous (but vital!) consistency behind the scenes. Pete shared stories from both the battlefield and the podcast studio, and we got into the nitty-gritty of turning conversations into opportunities. We talked about embracing failure, why networking is your secret weapon, and how just being genuinely interested in people opens doors you never expected. My hope for you is that you walk away inspired to take action, keep learning, and trust that the little things you do every day will eventually lead to something incredible. Thanks for joining me on this journey—let’s keep building together! Connect with Pete A. Turner YouTube:https://www.youtube.com/peteaturner LinkedIn:https://www.linkedin.com/in/peteaturner/ I’m building an online business in public — sharing every win, setback, and “I can’t believe that happened” moment along the way. If you’ve ever wondered what it really looks like to start from scratch, come along for the ride. Join the journey at https://wisdom.beehiiv.com/ Chapters 00:00 Welcome to Wisdom Journey & Introduction to Pete A. Turner 01:50 Podcasting Schedules, Flexibility, and Productivity Lessons 03:04 Handling Busy Lives and Managing Commitments 04:14 Approaches to Interviewing Repeat Guests 05:27 Shifting the Focus: Making the Guest Interesting 06:12 Is Podcasting a Full-Time Gig? 07:50 Monetizing the Podcast and Building a Media Brand 09:21 Skill Levels, Getting Good, and Charging for Value 10:15 Dreams, Work Ethic, and Doing the Hard Work 12:14 Value, Relationships, and Unexpected Opportunities 13:38 Learning From Conversations & The Power of Consistency 15:16 Turning Podcasting Into a Real Full-Time Business 16:48 Wealth Beyond Money: Connections and Fulfillment 18:22 Building and Maintaining a Podcast Network 19:52 The Importance of Small, Genuine Interactions 20:43 How People Remember You & Lasting Impressions 21:46 Spy Skills, Observation, and Control in Conversations 22:33 The Art of Interviewing: Guiding Conversations 23:43 Managing Interview Questions and Guest Types 25:44 Adapting Questions and Reading the Room 26:13 The Power of Silence and Letting Guests Unfold 28:08 When You’re the Guest: Switching Roles On and Off 29:04 Types of Challenging Podcast Guests 31:02 Making Each Guest Shine: Adapting as a Host 33:30 Getting Guests Off Script & Advanced Interviewing 35:06 How Do You Describe What You Do? 37:09 Embracing Silence and Improving as a Podcaster 38:44 Applying Podcasting Skills to Everyday Life 43:01 The Impact of Listening: Making People Feel Heard 44:02 Guest Outreach: Getting Great Podcast Guests 46:38 Being Interested in Others and Becoming Interesting 48:03 Traveling and Podcasting Remotely 49:40 Getting Amazing Stories vs. Celebrity Guests 51:11 Crafting Irresistible Guest Invitations 53:10 Reflecting on an Off-the-Script Conversation & Closing Remarks

    55 min

  8. 12/17/2025

    How to Use AI to Supercharge Your Productivity and Creativity – CJ Powers | Ep 89

    Hey friends, it's Wisdom Okonkwo here! In today’s episode, I sat down with CJ Powers, a communication strategist who’s lived at the intersection of creativity and AI for over 12 years. We peeled back the curtain on how AI can actually help us become more irreplaceably human—not less. CJ shared his powerful Three Cs framework: Communication, Connection, and Collaboration, and we dug into practical examples—from streamlining massive workflows to making your daily routine smoother and more meaningful. We also talked about why soft skills and genuine empathy will always set us apart, no matter how smart machines get. My hope for you after listening? That you’ll feel inspired, less overwhelmed by all the AI buzz, and ready to leverage these tools to amplify your own unique strengths. Let’s keep building, learning, and showing the world what only humans can do! Connect with Cj Powers Website:https://cjpowers.info I’m building an online business in public — sharing every win, setback, and “I can’t believe that happened” moment along the way. If you’ve ever wondered what it really looks like to start from scratch, come along for the ride. Join the journey at https://wisdom.beehiiv.com/ Connect 00:00 Welcome to Wisdom Journey & Guest Introduction 01:11 CJ Powers' Journey Into AI 02:11 Overcoming AI Fears and Seeing AI as a Tool 03:31 What It Means to Be Irreplaceably Human 05:20 The Three Cs Framework: Communication, Connection, Collaboration 08:03 Deep Dive into Communication: Clarify, Simplify, Amplify 09:45 Deep Dive into Connection: Engage, Relate, Build Relationships 14:40 Deep Dive into Collaboration: Align, Act, Achieve 17:56 The Power of the Three Cs in an AI World 20:30 Practical Ways to Leverage AI for Efficiency 26:21 Behind the Scenes: Building Automation for a Global Company 31:13 When to Use AI Tools, Agents, or Automation 33:43 Real-World Example: Automating a Scholarship Blog 37:48 Advice for Overcoming AI Overwhelm 39:28 Where to Find CJ Powers Online 40:22 Episode Wrap-Up and Listener Resources

    41 min
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4.9
out of 5
10 Ratings

About

Follow my unfiltered, real-time journey as I navigate the world of online income. No fake success stories or get-rich-quick schemes – just honest documentation of wins, losses, and everything in between. Each episode captures my weekly experiments with different online business models: freelancing, digital products, affiliate marketing, and more. I share exact numbers, strategies that worked (and failed), and the brutal reality of building income Want to be a guest on Wisdom Journey? Send Wisdom Okonkwo a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/wisdom

Information

  • Creator
    Wisdom
  • Years Active
    2025 - 2026
  • Episodes
    96
  • Rating
    Clean
  • Copyright
    © Wisdom
  • Show Website
    Wisdom Journey