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