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by Mark Labriola II
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- Mar 6, 202642 min
Stop Being Busy. Start Being Productive.
In this episode of The Friday Habit, host Mark Labriola II sits down with Jacob Hicks, a sales strategist and systems thinker passionate about helping entrepreneurs push past their comfort zones, master their time, and build businesses that last.Jacob shares his journey from a shy kid in small-town Iowa to a sales pro who's learned that the best approach to selling isn't closing hard — it's serving authentically. He breaks down the systems, follow-up strategies, and time management frameworks that help small business owners stop being "busy" and start being truly productive.🧠 Key TakeawaysFollow Up or Leave Money on the Table – 80% of business is won after 5+ follow-ups; most salespeople stop after oneSell Without Selling – Build cadences around adding value, not pushing a closeChaos Time Is Your Secret Weapon – Block 30–60 minutes daily for fires so the rest of your day stays protectedTime Blocking = Intentionality – Get granular; don't just block "work time," block specific tasksParkinson's Law Is Real – A task expands to fill the time you give it; iterate your blocks accordinglyAudit Your Time – Especially early on, track where your hours actually goWe Rise or Fall to Our Systems – Goals without systems are just wishes (James Clear)Your CRM Is Your Second Brain – Notes, pipeline stages, and follow-up history are non-negotiableResources & Links:Connect with Jacob!Website: https://jacobhickscoach.com/growth-hub/Download the free Friday Habit Guide: https://thefridayhabit.com0:00 - Chaos Time Strategy - Introduction to time blocking and chaos time concept1:30 - Podcast Introduction & Jacob's Background - Welcome and guest intro3:38 - Jacob's Sales Journey - Early sales experiences and career development5:06 - Modern Sales Philosophy - Moving away from hard closing tactics to relationship building6:54 - Follow-Up Systems - Importance of consistent follow-up in sales8:40 - Sales as Service - Reframing sales as helping people with value-driven follow-up10:49 - Breaking Through Comfort Zones - Overcoming shyness and mindset shifts in sales12:00 - Playing it Too Safe - Recognizing when you're leaving business on the table14:25 - Building Authentic Relationships - Providing free value and making genuine connections16:20 - Time Management Introduction - The constant battle with the clock for entrepreneurs17:14 - Time Blocking Explained - Detailed breakdown of time blocking strategy and Parkinson's Law20:52 - Time Audits - Tracking where your time actually goes22:42 - Busyness vs Productivity - Reframing "busy" as productive and positive24:08 - Coaching Through Time Management - Accountability and overcoming roadblocks26:47 - Building Sustainable Systems - Why small businesses struggle with systems27:45 - Podcast Systems Example - How systems prevent pod fade and business collapse28:52 - Understanding Your Why - Connecting goals to personal motivation29:59 - Follow-Up Systems: 10x10 and 36 Touch - Specific follow-up cadences and frameworks32:18 - CRM as Second Brain - Importance of CRM systems for tracking relationships34:28 - Choosing the Right CRM - CRM recommendations and selection criteria35:60 - Jacob's Personal Habits - Daily practices including time blocking, phone management, and gray scale trick39:36 - Eliminating Friction - Reducing barriers to success (gym bag example)41:32 - Final Advice & Outro - Start with chaos time and closing remarks
- Feb 27, 202653 min
Why Taking Action Beats Having The Perfect Plan
In this episode of The Friday Habit, host Mark Labriola II sits down with serial entrepreneur Jay Sapovits, a builder who knows firsthand how to turn setbacks into springboards.Jay shares his raw journey—from early success in sports media and private aviation, to losing everything during the financial crisis, to rebuilding and scaling Inked, a custom merch company on track to surpass $5M in revenue.🧠 Key Takeaways Entrepreneurship Isn’t a Straight Line – Success, failure, and reinvention are all part of the processZero to One Is About Action – Stop overthinking and start movingDon’t Spend Money Too Early – Cash preservation beats premature scalingHire for the Role, Not Potential – Designers ≠ operatorsNever Burn Bridges – Integrity compounds over timeYour Network Is a Muscle – Make one reconnecting phone call per weekResources & Links:Connect with Jay!Email: Jay@inkdstores.comLinkedin: https://www.linkedin.com/in/jaysap/ Download the free Friday Habit Guide: https://thefridayhabit.com01:32 Welcome to The Friday Habit02:10 Meet Jay Sapovits: Serial Entrepreneur & Reinvention Expert10:45 Authentic Personal Branding (White Glasses Story)13:40 Losing Everything at 39: Hitting Rock Bottom16:20 Early Success & the Confidence That Came With It18:40 When Ego Meets the Financial Crisis20:15 Starting Over: Rebuilding Confidence from Scratch24:35 High-Stakes Negotiation & the St. Barts Pivot29:10 Why You Should Never Burn Bridges31:05 The Zero-to-One Playbook Every Founder Needs37:50 The #1 Mistake New Entrepreneurs Make (Spending Too Early)40:45 Why the First $1M Is the Hardest43:50 Hiring the Right People Changed Everything48:45 Pivoting Into the Merch Business & Finding Product-Market Fit50:35 Jay’s Friday Habit: One Call That Changes Everything52:30 Where to Connect With Jay & Final TakeawaysWhy Taking Action Beats Having The Perfect Plan
- Feb 20, 202655 min
The Real Reason Sales Stop Working In Tough Markets
In this episode of The Friday Habit, Mark Labriola II interviews Walter Crosby, CEO of Helix Sales Development, who shares his extensive experience in transforming underperforming sales teams into revenue-generating powerhouses. The conversation covers Walter's journey into sales, the challenges of transitioning from a sales role to business ownership, and the importance of hiring the right salespeople. Walter emphasizes the need for accountability, clear expectations, and effective compensation structures to motivate sales teams, especially during tough economic times. He also discusses the significance of prospecting and how leaders can shift company culture to foster a thriving sales environment.🧠 Key Takeaways If your sales stall in a down market, it’s usually a systems problem—not the economy.Founders must translate their “natural” sales instincts into repeatable messaging.Hire salespeople who already sell to your buyer—not necessarily your industry.Comp plans should motivate discomfort, not create complacency.Activity, accountability, and standards separate real sales teams from lucky ones.Resources & Links:Connect with Walter!LinkedIn:www.linkedin.com/in/walterlcrosbyHelix Sales: helixsalesdevelopment.comDownload the free Friday Habit Guide: https://thefridayhabit.comChapters00:49 Introduction to The Friday Habit01:39 Walter Crosby's Sales Journey08:28 Transitioning from Sales to Entrepreneurship13:29 Overcoming Sales Challenges as a Small Business20:26 Finding the Right Salesperson and Compensation23:09 Balancing Base Salary and Motivation26:47 Evaluating Sales Team Performance27:49 Identifying Sales Team Strengths and Weaknesses34:47 Coaching vs. Accountability in Sales37:48 Setting Expectations for Sales Success45:29 Building a Thriving Sales Culture
- Feb 13, 202640 min
Why Regret Is More Dangerous Than Risk With Henry Yoshida
In this episode of The Friday Habit, host Mark Labriola II sits down with Henry Yoshida, CEO and Co-Founder of Rocket Dollar, to unpack what it really takes to build a durable fintech company in a highly regulated industry.Henry shares his journey from a risk-averse upbringing and a stable career at Merrill Lynch to founding multiple companies—including Rocket Dollar, now part of a platform managing $12B+ in retirement assets. They dive deep into ownership, timing, regret vs. risk, venture capital trade-offs, and why paying attention to “small signals” can unlock massive opportunities.🧠 Key TakeawaysRegret Is More Dangerous Than Risk – Fear fades, but “what if?” lingersStay a Mile Deep, Not a Mile Wide – Specialization creates leverageTiming Matters More Than Ideas – Many failures are just too earlyVenture Capital Is a Clock – Momentum determines survivalBuild for the Right Customer Segment – CAC must beat LTVBalance Fuels Longevity – Burnout kills good businessesCuriosity Compounds – Small observations connect into big ideasResources & Links:🔗 Learn more about Rocket Dollar: https://bit.ly/4qaDVxUConnect With Henry! Instagram: @fitfinancehenry📘 Download the free Friday Habit Guide: https://thefridayhabit.comChapters:00:42 Meet Henry Yoshida: CEO & Co-Founder of Rocket Dollar02:05 Growing Up Risk-Averse & Fear of Regret04:45 Merrill Lynch’s Competitive Culture07:55 Early Career Lessons That Shaped a Founder10:40 Leaving Stability to Take the Leap13:10 Building & Selling the First Business16:00 Venture Capital, Timing, and Momentum18:55 Failing Into an Acquisition21:35 Why Most Startups Pick the Wrong Customer24:10 The Problem With Traditional IRAs & 401ks27:10 What Rocket Dollar Actually Does30:05 Building in a Highly Regulated Industry32:45 Risk, Regret, and Confidence as a Founder35:40 Burnout, Balance, and Founder Mistakes38:05 Henry’s Friday Habit: Stay Curious & Connect the Dots40:29 Outro
- Feb 13, 202649 min
Why Every Tough Conversation Goes Wrong
In this episode of The Friday Habit, host Mark Labriola II interviews Greg Stevens, an executive coach and expert in conflict resolution. They discuss the importance of managing emotions in difficult conversations, the journey to understanding and repairing incomplete relationships, and the skills necessary for effective communication. Greg shares insights from his experiences and his book, 'Build New Bridges: The Art of Restoring Impossible Relationships,' emphasizing the need for self-awareness and accountability in both personal and professional relationships. The conversation also touches on performance reviews and how to approach them constructively, as well as the significance of closure in relationships.🧠 Key Takeaways Greg Stevens emphasizes the importance of practicing what you teach in relationships.Incomplete relationships can be identified and addressed for personal growth.Managing emotions is crucial during difficult conversations to avoid escalation.Timing is key; sometimes it's best to step away and revisit a conversation later.Self-awareness is foundational for effective communication and conflict resolution.Performance reviews should focus on inspiration and constructive feedback.Understanding the difference between impossible and salvageable relationships is vital.Closure in relationships can lead to personal healing and growth.Asking questions can help manage emotional responses during conflicts.Investing in conflict resolution skills can lead to breakthroughs in relationships.Resources & Links:Connect with Greg!Website: alignment-resources.com/Greg's Podcast: ashotofinspiration.comDownload the free Friday Habit Guide: https://thefridayhabit.com01:05 Introduction to The Friday Habit02:29 Meet Greg Stevens: The Relationship Coach05:01 The Journey to Conflict Resolution07:48 Understanding Incomplete Relationships09:23 Managing Emotions in Conflict12:34 The Importance of Timing in Conversations14:02 Common Communication Challenges16:04 Building Self-Awareness and Skills19:15 Learning from Real-Life Experiences22:41 Empathy in Parenting and Relationships27:26 Understanding Relationship Dynamics32:46 Constructive Performance Reviews37:21 Measuring Communication Progress40:44 Starting with Yourself in Relationships
- Jan 30, 202643 min
Compete On Value, Not Price
In this episode of The Friday Habit, host Mark Labriola II interviews Chad Prinkey, founder and CEO of Well Built Construction Consulting. They discuss Chad's journey from a successful corporate career to entrepreneurship, the challenges of building a scalable business, and the importance of leadership and culture in driving growth. Chad shares insights on competing on value rather than price, the mindset shifts necessary for long-term success, and key systems that can help construction businesses thrive. The conversation concludes with actionable takeaways for listeners looking to improve their own businesses.🧠 Takeaways:Chad Prinkey emphasizes the importance of building a strong company culture.Growth can expose underlying issues in a business.Leadership development is crucial for scaling a company.Competing on value rather than price is essential for profitability.Business owners should prioritize investing in their own companies.Mindset shifts are necessary for long-term success.Creating a three-year organizational chart can guide business growth.Understanding financial health is critical before strategic planning.Building a team of leaders at all levels is vital for success.Continuous improvement and reinvestment in the business are key to sustainability.Resources & Links:Connect with Chad!Website: www.wellbuiltconsulting.comDownload the free Friday Habit Guide: https://thefridayhabit.com00:37 Welcome To The Friday Habit01:24 Meet Chad Prinkey03:03 Delicious Crabs06:28 Chad's Background08:13 Company Growth 09:59 Leaving Something Good For Something Better14:46 The Difficulties Of Leaving Something Good 16:13 How Chad Helped A Company Grow From 300 to 3,000 Employees18:31 Building Leaders That Scale 24:49 Advice For Leaders Playing The Long Game29:47 When Should You Bring New Leaders?32:46 Chad's Book WellBuilt40:06 Take Action42:13 Outro
- Jan 23, 202643 min
Turning A Side Hustle Into A Brand
In this episode of The Friday Habit, host Mark Labriola II interviews Emma Tessler, founder and CEO of NinentyFiveMedia, a digital marketing agency. Emma shares her journey from a side hustle in interior design to leading a successful remote team specializing in social media strategy and brand storytelling. The conversation covers the importance of building a strong company culture, the challenges of scaling a business, and the evolving landscape of video content in the age of AI. Emma emphasizes the significance of authenticity in marketing and offers actionable advice for entrepreneurs looking to grow their brands.🧠 Takeaways:Emma Tessler transitioned from a side hustle to CEO of 95 Media.The importance of community engagement in social media marketing.Building authority online is crucial for trust and sales.Consistency in content creation leads to better results.Hiring for will over skill can enhance team dynamics.Video content should reflect authenticity to stand out.Niche down in services, but not in target audience.A remote team can provide flexibility and access to diverse talent.Scaling requires effective delegation and teamwork.Building a strong company culture is essential for remote teams.Resources & Links:Connect with Emma and NinetyFivemedia!Website: Ninetyfivemedia.coInstagram: @Ninenty.Five.MediaDownload the free Friday Habit Guide: https://thefridayhabit.com00:35 Introduction to The Friday Habit01:47 Meet Emma Tessler04:15 Emma's background06:08 Building 95 Media: From Side Hustle to Success07:13 Humble Beginnings11:28 Building NinentyFiveMedia21:59 Creating Company Culture23:19 Navigating Remote Work34:34 Advice for Hesitant Business Owners26:01 Staff Structure29:04 Video Content Strategy32:45 Building Authority Online34:31 Working On, Not In Your Business 35:47 Is there Riches in the Niches?39:52 Planning For The Future41:02 Actionable Steps to Scale Your Brand 41:41 Outro
- Jan 16, 202637 min
The Mindset That Scales Your Business
In this episode of The Friday Habit, Mark Labriola II interviews John Gallagher, a seasoned leadership coach, who shares insights on the journey of leadership, the importance of emotional intelligence, and the mindset shifts necessary for entrepreneurs. Gallagher emphasizes the need for practical frameworks, the signs that indicate a business owner may need a coach, and the significance of legacy in leadership. He also discusses the challenges of consistency, the impact of distractions, and the importance of prioritization and delegation. The conversation concludes with Gallagher's advice on making small changes for personal growth.🧠 Takeaways:Leadership is a continuous journey of growth and learning.Entrepreneurs must shift their mindset from operator to team leader.Delegation is crucial for scaling a business effectively.Understanding the 'so what, now what, so that' framework helps clarify purpose.Regular reflection is key to developing emotional intelligence.Distractions can hinder leadership effectiveness and must be managed.Prioritization is essential for effective time management.Legacy is built through intentional relationships and impact on others.Consistency in habits is more important than initial motivation.Coaching can provide accountability and support for personal and professional growth.Resources & Links:Connect with John: https://coachjohngallagher.com/Linkedin: https://www.linkedin.com/in/coachjohngallagherDownload the free Friday Habit Guide: https://thefridayhabit.com00:00 Introduction to The Friday Habit02:13 Meet John Gallagher03:22 John Gallagher's Leadership Journey09:30 Mindset Shifts for Entrepreneurs13:40 Practical Leadership Frameworks16:17 Recognizing the Need for Coaching18:50 The Impact of Leadership on Legacy 20:43 Developing Emotional Intelligence26:11 Consistency in Leadership Development29:58 Faith and Entrepreneurship: Balancing Control and Trust32:07 Overcoming Distractions: The Entrepreneur's Challenge34:14 Prioritization and Delegation: Keys to Effective Leadership35:30 The Importance of Accountability and Continuous Learning36:19 Small Changes for Big Impact: Stop Eating French Fries36:58 Outro
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About The Friday Habit
Grow your business. Lead with purpose. Love your life.The Friday Habit gives entrepreneurs and small business owners actionable tips, inspiring interviews, and real-world strategies to help you scale smart and stay sane. Hosted by Mark Labriola II, this weekly show is your permission slip to build a business that works for you—not the other way around.
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