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