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 Takeaways
Follow Up or Leave Money on the Table – 80% of business is won after 5+ follow-ups; most salespeople stop after one
Sell Without Selling – Build cadences around adding value, not pushing a close
Chaos Time Is Your Secret Weapon – Block 30–60 minutes daily for fires so the rest of your day stays protected
Time Blocking = Intentionality – Get granular; don't just block "work time," block specific tasks
Parkinson's Law Is Real – A task expands to fill the time you give it; iterate your blocks accordingly
Audit Your Time – Especially early on, track where your hours actually go
We 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-negotiable

Resources & Links:
Connect with Jacob!
Website: https://jacobhickscoach.com/growth-hub/
Download the free Friday Habit Guide: https://thefridayhabit.com

0:00 - Chaos Time Strategy - Introduction to time blocking and chaos time concept
1:30 - Podcast Introduction & Jacob's Background - Welcome and guest intro
3:38 - Jacob's Sales Journey - Early sales experiences and career development
5:06 - Modern Sales Philosophy - Moving away from hard closing tactics to relationship building
6:54 - Follow-Up Systems - Importance of consistent follow-up in sales
8:40 - Sales as Service - Reframing sales as helping people with value-driven follow-up
10:49 - Breaking Through Comfort Zones - Overcoming shyness and mindset shifts in sales
12:00 - Playing it Too Safe - Recognizing when you're leaving business on the table
14:25 - Building Authentic Relationships - Providing free value and making genuine connections
16:20 - Time Management Introduction - The constant battle with the clock for entrepreneurs
17:14 - Time Blocking Explained - Detailed breakdown of time blocking strategy and Parkinson's Law
20:52 - Time Audits - Tracking where your time actually goes
22:42 - Busyness vs Productivity - Reframing "busy" as productive and positive
24:08 - Coaching Through Time Management - Accountability and overcoming roadblocks
26:47 - Building Sustainable Systems - Why small businesses struggle with systems
27:45 - Podcast Systems Example - How systems prevent pod fade and business collapse
28:52 - Understanding Your Why - Connecting goals to personal motivation
29:59 - Follow-Up Systems: 10x10 and 36 Touch - Specific follow-up cadences and frameworks
32:18 - CRM as Second Brain - Importance of CRM systems for tracking relationships
34:28 - Choosing the Right CRM - CRM recommendations and selection criteria
35:60 - Jacob's Personal Habits - Daily practices including time blocking, phone management, and gray scale trick
39:36 - Eliminating Friction - Reducing barriers to success (gym bag example)
41:32 - Final Advice & Outro - Start with chaos time and closing remarks

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 process
Zero to One Is About Action – Stop overthinking and start moving
Don’t Spend Money Too Early – Cash preservation beats premature scaling
Hire for the Role, Not Potential – Designers ≠ operators
Never Burn Bridges – Integrity compounds over time
Your Network Is a Muscle – Make one reconnecting phone call per week

Resources & Links:
Connect with Jay!
Email: Jay@inkdstores.com
Linkedin: https://www.linkedin.com/in/jaysap/
Download the free Friday Habit Guide: https://thefridayhabit.com

01:32 Welcome to The Friday Habit
02:10 Meet Jay Sapovits: Serial Entrepreneur & Reinvention Expert
10:45 Authentic Personal Branding (White Glasses Story)
13:40 Losing Everything at 39: Hitting Rock Bottom
16:20 Early Success & the Confidence That Came With It
18:40 When Ego Meets the Financial Crisis
20:15 Starting Over: Rebuilding Confidence from Scratch
24:35 High-Stakes Negotiation & the St. Barts Pivot
29:10 Why You Should Never Burn Bridges
31:05 The Zero-to-One Playbook Every Founder Needs
37:50 The #1 Mistake New Entrepreneurs Make (Spending Too Early)
40:45 Why the First $1M Is the Hardest
43:50 Hiring the Right People Changed Everything
48:45 Pivoting Into the Merch Business & Finding Product-Market Fit
50:35 Jay’s Friday Habit: One Call That Changes Everything
52:30 Where to Connect With Jay & Final TakeawaysWhy Taking Action Beats Having The Perfect Plan

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/walterlcrosby
Helix Sales:
helixsalesdevelopment.com

Download the free Friday Habit Guide: https://thefridayhabit.com

Chapters

00:49 Introduction to The Friday Habit
01:39 Walter Crosby's Sales Journey
08:28 Transitioning from Sales to Entrepreneurship
13:29 Overcoming Sales Challenges as a Small Business
20:26 Finding the Right Salesperson and Compensation
23:09 Balancing Base Salary and Motivation
26:47 Evaluating Sales Team Performance
27:49 Identifying Sales Team Strengths and Weaknesses
34:47 Coaching vs. Accountability in Sales
37:48 Setting Expectations for Sales Success
45:29 Building a Thriving Sales Culture

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.com

Download the free Friday Habit Guide: https://thefridayhabit.com

01:05 Introduction to The Friday Habit
02:29 Meet Greg Stevens: The Relationship Coach
05:01 The Journey to Conflict Resolution
07:48 Understanding Incomplete Relationships
09:23 Managing Emotions in Conflict
12:34 The Importance of Timing in Conversations
14:02 Common Communication Challenges
16:04 Building Self-Awareness and Skills
19:15 Learning from Real-Life Experiences
22:41 Empathy in Parenting and Relationships
27:26 Understanding Relationship Dynamics
32:46 Constructive Performance Reviews
37:21 Measuring Communication Progress
40:44 Starting with Yourself in Relationships

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 Takeaways

Regret Is More Dangerous Than Risk – Fear fades, but “what if?” lingers
Stay a Mile Deep, Not a Mile Wide – Specialization creates leverage
Timing Matters More Than Ideas – Many failures are just too early
Venture Capital Is a Clock – Momentum determines survival
Build for the Right Customer Segment – CAC must beat LTV
Balance Fuels Longevity – Burnout kills good businesses
Curiosity Compounds – Small observations connect into big ideas

Resources & Links:
🔗 Learn more about Rocket Dollar: https://bit.ly/4qaDVxU
Connect With Henry!
Instagram: @fitfinancehenry

📘 Download the free Friday Habit Guide: https://thefridayhabit.com

Chapters:
00:42 Meet Henry Yoshida: CEO & Co-Founder of Rocket Dollar
02:05 Growing Up Risk-Averse & Fear of Regret
04:45 Merrill Lynch’s Competitive Culture
07:55 Early Career Lessons That Shaped a Founder
10:40 Leaving Stability to Take the Leap
13:10 Building & Selling the First Business
16:00 Venture Capital, Timing, and Momentum
18:55 Failing Into an Acquisition
21:35 Why Most Startups Pick the Wrong Customer
24:10 The Problem With Traditional IRAs & 401ks
27:10 What Rocket Dollar Actually Does
30:05 Building in a Highly Regulated Industry
32:45 Risk, Regret, and Confidence as a Founder
35:40 Burnout, Balance, and Founder Mistakes
38:05 Henry’s Friday Habit: Stay Curious & Connect the Dots
40:29 Outro

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.com
Download the free Friday Habit Guide: https://thefridayhabit.com

00:37 Welcome To The Friday Habit
01:24 Meet Chad Prinkey
03:03 Delicious Crabs
06:28 Chad's Background
08:13 Company Growth
09:59 Leaving Something Good For Something Better
14:46 The Difficulties Of Leaving Something Good
16:13 How Chad Helped A Company Grow From 300 to 3,000 Employees
18:31 Building Leaders That Scale
24:49 Advice For Leaders Playing The Long Game
29:47 When Should You Bring New Leaders?
32:46 Chad's Book WellBuilt
40:06 Take Action
42:13 Outro

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.co
Instagram: @Ninenty.Five.Media
Download the free Friday Habit Guide: https://thefridayhabit.com

00:35 Introduction to The Friday Habit
01:47 Meet Emma Tessler
04:15 Emma's background
06:08 Building 95 Media: From Side Hustle to Success
07:13 Humble Beginnings
11:28 Building NinentyFiveMedia
21:59 Creating Company Culture
23:19 Navigating Remote Work
34:34 Advice for Hesitant Business Owners
26:01 Staff Structure
29:04 Video Content Strategy
32:45 Building Authority Online
34:31 Working On, Not In Your Business
35:47 Is there Riches in the Niches?
39:52 Planning For The Future
41:02 Actionable Steps to Scale Your Brand
41:41 Outro

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/coachjohngallagher

Download the free Friday Habit Guide: https://thefridayhabit.com

00:00 Introduction to The Friday Habit
02:13 Meet John Gallagher
03:22 John Gallagher's Leadership Journey
09:30 Mindset Shifts for Entrepreneurs
13:40 Practical Leadership Frameworks
16:17 Recognizing the Need for Coaching
18:50 The Impact of Leadership on Legacy
20:43 Developing Emotional Intelligence
26:11 Consistency in Leadership Development
29:58 Faith and Entrepreneurship: Balancing Control and Trust
32:07 Overcoming Distractions: The Entrepreneur's Challenge
34:14 Prioritization and Delegation: Keys to Effective Leadership
35:30 The Importance of Accountability and Continuous Learning
36:19 Small Changes for Big Impact: Stop Eating French Fries
36:58 Outro