Hustle Over Everything

Hustle Over Everything

By Alex WhitfieldBusinessEntrepreneurship
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Hustle Over Everything episodes

  • 216: Most Men Have No Idea What Happens in Divorce Court Until It’s Too Late

    In this candid conversation, Alex Whitfield sits down with Ontario divorce lawyer Justin Lee to unpack the realities of marriage, divorce, and what entrepreneurs often overlook when it comes to love and legacy. From legal strategies to cultural taboos, this episode dives deep into the personal and professional consequences of modern relationships.

    Topics covered include:

    • How divorce courts really work in Ontario

    • Common mistakes entrepreneurs make before marriage

    • The truth about prenups — who they protect and who they don’t

    • Why men often lose in court and how to prepare

    • Real stories of million-dollar divorces in Toronto

    • How to protect your business and assets before it’s too late

    • Cultural taboos in the Black community around marriage and divorce

    • Advice for young entrepreneurs who want love and legacy

    Chapters:
    00:00 Intro
    03:08 Understanding Divorce Law and Its Impact
    05:54 The Importance of Prioritizing Relationships
    08:55 Cultural Perspectives on Marriage
    11:49 Men's Roles and Expectations in Relationships
    14:51 The Subtle Signs of Relationship Decline
    18:11 Personal Experiences with Divorce
    21:13 Reconciliation: Is It Possible?
    24:03 The Nature of Love and Marriage
    27:06 Prenuptial Agreements: A Necessary Discussion
    30:05 Financial Considerations in Marriage
    33:06 Long-Term Projections in Relationships
    41:16 The Emotional Disconnect in Professional Advice
    44:07 The Irrationality of Divorce Decisions
    46:14 Understanding Legal Strategies in Divorce
    49:40 The Cost of Legal Representation
    52:28 The Underlying Reasons for Divorce
    56:36 The Role of Love Languages in Relationships
    01:00:51 The Impact of Financial Disparities on Relationships
    01:05:09 Navigating Business Partnerships in Marriage
    01:09:11 Accountability and Faults in Relationships
    01:14:16 Cultural Influences on Divorce Perspectives

    1 hr 21 min
  • 215: Draymond Green | Wildcard Ft. Clyde Smith

    In this engaging conversation, Alex Whitfield and Clyde from Relentless Diaries explore the evolving landscape of podcasting, the cultural significance of artists like Drake and Kendrick, and the dynamics of community support in the industry. Clyde shares his journey in podcasting, the birth of Relentless Diaries, and the importance of authenticity and chemistry in creating impactful content. The discussion also touches on the influence of marketing strategies in politics, particularly regarding Trump and his approach to appealing to audiences. In this conversation, Alex Whitfield discusses various topics, including Canadian exports, the implications of becoming the 51st state, the DEI debate, cultural relevance in politics, the future of cryptocurrency, and the podcasting landscape in Canada. He emphasizes the need for better communication and understanding between Canada and the US, critiques the current state of DEI initiatives, and explores the impact of celebrity politics on cultural narratives. Additionally, he shares insights on the cryptocurrency market and the potential for growth in the Canadian podcasting industry.Chapters00:00 Introduction to Clyde and Podcasting Culture02:56 The Impact of Joe Budden and Podcasting Success06:03 Clyde's Journey and the Birth of Relentless Diaries08:59 The Dynamics of Podcasting and Community Support12:12 Drake vs. Kendrick: The Cultural Divide15:03 The Role of Authenticity in Music and Podcasting18:05 The Evolution of Relentless Diaries20:59 Podcasting as a Passion vs. Business24:06 The Importance of Chemistry in Podcasting26:50 Basketball Analogies in Podcasting Dynamics30:03 Trump's Influence on Canada and Marketing Strategies35:35 Canadian Exports and Economic Realities42:26 The DEI Debate: Perspectives and Misconceptions46:49 Cultural Relevance and the Impact of Celebrity Politics58:00 Cryptocurrency: The Future of Finance?01:05:47 The Future of Podcasting in Canada

    1 hr 11 min
  • 214: Why Podcasts keep breaking up

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    In this episode, I explore the common phenomenon of podcast breakups, diving into the key reasons behind them—money, creative differences, unequal workloads, and personal life changes. I emphasize the importance of clear roles, open communication, and mutual respect to maintain a healthy working relationship with podcast partners. I also share actionable steps to help prevent breakups and ensure a successful podcasting journey.Timestamps:00:00 -The Podcast Breakup Phenomenon02:48 -Understanding Roles and Responsibilities06:11 - Creative Differences and Communication09:08 - Unequal Workload and Commitment Issues11:51 - Ego and Personality Clashes14:46 - Life Changes and Their Impact18:08 - The Slow Fade: How Breakups Happen21:02 - Actionable Steps to Prevent BreakupsFollow us to stay updated for more content  / 247hustler  

    29 min
  • 213: Economics Prof Reveals the Truth About Tariffs & Canada’s Future

    In this conversation, Alex Whitfield and Frank Lazer discuss the implications of tariffs on the Canadian economy, the challenges faced by the auto industry, and the need for a stronger startup culture in Canada. They emphasize the importance of common sense in political leadership and the impact of retaliatory tariffs on consumers. The discussion also touches on the brain drain phenomenon, indigenous rights in resource management, and the future opportunities for young entrepreneurs in Canada, particularly in the northern regions.00:00 - Intro: The State of Canadian Politics and Common Sense01:11 - Understanding Tariffs: Basics and Implications04:17 - Impact of U.S. Tariffs on Canadian Economy10:37 - Challenges in the Canadian Auto Industry12:31 - The Need for a Startup Culture in Canada15:46 - Retaliatory Tariffs: A Misguided Approach19:51 - The Brain Drain and Talent Retention22:47 - Indigenous Rights and Resource Management25:17 - Negotiation Strategies and Missed Opportunities30:40 - The Future of Young Entrepreneurs in Canada39:43 - Opportunities in Northern Canada and Indigenous CollaborationFollow us here: https://www.instagram.com/247hustler/

    45 min
  • 212: Drake Suing UMG, Leaving Toronto To Get Success, Keeping your Brother accountable and more.

    In this episode of Hustle Over Everything, we sit down with Troy Crossfield to break down the realities of the entertainment industry, from navigating music deals to the tough choices artists face in chasing success. We dive into why many creatives have to leave their hometowns to level up, the implications of Drake’s lawsuit against Universal Music, and the crucial role accountability plays in business.Alex Whitfield and Troy also explore the mindset within Toronto’s creative community—how collaboration and support can change the game. Troy opens up about his journey in theater, including the creation of White Lie, and the fulfillment that storytelling has brought him. He shares wisdom on navigating relationships, dealing with loss, and avoiding the wrong ‘doors’ in life—To have a better life as a man.Beyond that, we get into the art of managing talent, upcoming projects, and what it takes to build a lasting legacy in the industry. This conversation is a masterclass for creatives looking to make an impact.00:00 The Journey to Success: Leaving Home for Opportunity07:02 Navigating the Music Industry: Deals and Dynamics12:08 Drake vs. Universal: The Implications of a Lawsuit17:58 Accountability and Strategy: Navigating Industry Politics21:58 The Impact of Hometown Support on Artists33:58 Balancing Family and Career: The Dilemma of Growth38:45 The Toronto Mindset and Community Support41:12 The Importance of Contracts and Accountability43:40 The Journey of Creating "White Lie"49:01 Navigating Relationships and Loss54:30 Life Lessons: Doors to Avoid01:07:19 Managing Artists and Upcoming ProjectsYou can find out more about Troy here: https://www.instagram.com/troycrossfield/You can find us on Instagram here: https://www.instagram.com/247hustler/

    1 hr 5 min
  • 211 | The Harsh Truth About Event Sponsorships In 2025. Ft. Jackie Clarke

    This week on the podcast, we’ve got an episode for creators! We’re diving deep into event sponsorships and brand deals with none other than Jackie

    Jackie has partnered with some of the biggest brands, from Nike to Coca-Cola, and she’s sharing her expertise with us.
    Here’s what we cover:
    - How to provide real value for brands
    - A live media kit audit with Jackie
    - The surprising ways Donald Trump’s influence could impact brand deals for Black creators
    … and so much more!
    The episode drops soon—don’t miss it! Subscribe to Hustle Over Everything on YouTube today.
    Filmed at Whitmedia Studios in Oshawa

    Timestamps:


    00:00 Impact of Politics on Brand Deals

    02:48 The Role of DEI in Sponsorships

    06:04 Creating Value in Sponsorships

    08:51 Return on Engagement vs. Return on Investment

    11:45 Profitability of Events

    15:08 Sponsorships as Partnerships

    18:02 Crafting Effective Media Kits

    20:56 Common Mistakes in Sponsorship Decks

    23:51 Customizing Sponsorship Experiences

    28:35 Event Planning Essentials

    30:28 The Importance of Early Budgeting

    33:22 Maximizing Sponsorship Opportunities

    37:13 Navigating Challenges in Event Sponsorship

    40:07 Understanding the Value of Sponsorships

    44:42 The Economics of Event Planning

    47:03 Perception vs. Reality in the Event Industry

    50:18 Negotiating Brand Collaborations


    57 min
  • 210 | Radio Host: Why I dislike Kendricks Music, Toronto Tempo, PostPartum and more

    Happy New Year and Welcome Back! Today on the show we've got Alicia Ace West. Host of Flow 98.7, Toronto Argonauts, and Extra Gravy podcast. Extra Gravy is one of my favorite podcasts so make sure you subscribe to them on YouTube.

    In this episode, we discuss:
    - The truth behind Toronto media
    - Reviewing the Toronto tempo name
    - Why Alicia Dislikes Kendrick Lamar &
    - Alicia reveals what’s really going on with her.
    Make sure you check out our sponsor Scotthill Cuisine.
    For the next month, we're doing a promotion where you get a free appetizer when you dine in. Simply take a screenshot of the episode and show it to the waiter.

    You can find Alicia here: https://www.instagram.com/aliciaacewest/Her podcast: https://www.youtube.com/@WaitImaMomPodcast Extra Gravy: https://www.youtube.com/@ExtraGravy


    You can find us here: https://www.instagram.com/247hustler/

    2 min

About Hustle Over Everything

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Hustle Over Everything Is an entrepreneurship podcast focused on sharing stories tips and tactics from entrepreneurs who have done it. It's exciting & challenging taking an idea, a goal, and…