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