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Tag Archive for: changing

Stop Cold Calling Forever: How AI Can 3X Your Sales

June 26, 2025/in Career Advice, Communication Skills, Expert Positioning, General Tips, Goal Setting, Lead Generation, Leadership, Mindset, New Rules, Personal, Personal Productivity, Podcasts, Prospecting-Business Development, Sales Process, The Bill Caskey Podcast/by Bill Caskey

Ready to transform your sales game? In this episode, Bill Caskey sits down with Jonathan Mast, founder of White Beard Strategies, to reveal how AI can revolutionize your sales process—without replacing you.

If you’re tired of endless cold calls, struggling to keep up with CRM updates, or feeling overwhelmed by your daily tasks, this conversation is a game-changer. Jonathan shares his journey from skeptical observer to AI advocate, explaining how he built a seven-figure business in under two years using AI as his secret weapon.

Jonathan proves that AI isn’t about working harder—it’s about amplifying your existing skills to work smarter. Whether you want to work fewer hours for the same money or work the same hours to make 3-4x more, AI makes both possible.

No tech background required—just a willingness to get in the game.

Want to break free and soar to new heights? “12 Bold Moves” is your gateway to a fearless reinvention of self and unlocking unprecedented sales success.  Get your copy now at http://12boldmoves.com.

Subscribe to The Bill Caskey Podcast to get this delivered to your phone weekly!

 
https://billcaskey.com/wp-content/uploads/2X-Podcast-Jonathan-Mast.png 720 1280 Bill Caskey https://billcaskey.com/wp-content/uploads/2018/05/BC-Logo-2018-Padding.png Bill Caskey2025-06-26 16:31:482025-06-26 16:31:48Stop Cold Calling Forever: How AI Can 3X Your Sales

Staying Relevant After 50: Sales Success in a Changing World

May 14, 2025/in Career Advice, Communication Skills, Expert Positioning, General Tips, Goal Setting, Lead Generation, Leadership, Mindset, New Rules, Personal, Personal Productivity, Podcasts, Prospecting-Business Development, Sales Process, The Bill Caskey Podcast/by Bill Caskey

Bill Caskey tackles a topic close to home – how sales professionals over 50 can maintain and even increase their relevance in a rapidly evolving marketplace. Drawing from personal experience and client success stories, Bill shares five critical strategies that seasoned professionals must adopt to thrive.

Whether you’re approaching 50, already there, or managing team members in this age group, this episode provides actionable insights on leveraging your wisdom and experience while avoiding the trap of outdated tactics. Learn why working harder isn’t the answer and discover how to create an “everyday lead strategy” that works while you sleep.

Want to break free and soar to new heights? “12 Bold Moves” is your gateway to a fearless reinvention of self and unlocking unprecedented sales success.  Get your copy now at http://12boldmoves.com.

Subscribe to The Bill Caskey Podcast to get this delivered to your phone weekly!

 
https://billcaskey.com/wp-content/uploads/BC-Pod-05-14-25.png 720 1280 Bill Caskey https://billcaskey.com/wp-content/uploads/2018/05/BC-Logo-2018-Padding.png Bill Caskey2025-05-14 17:58:122025-05-14 17:58:12Staying Relevant After 50: Sales Success in a Changing World

Back to the Basics

October 21, 2020/in Career Advice, Communication Skills, Expert Positioning, General Tips, Goal Setting, Lead Generation, Mindset, Personal, Personal Productivity, Podcasts, Prospecting-Business Development, Sales Process, The Bill Caskey Podcast/by Bill Caskey

On this episode I get back to the basics. These are the basic sales skills that are essential for all salespeople to master in order to achieve their goals and properly serve their customers.

This is a perfect time to brush up on your basics as we start to transition out of this disruption.

Also, enrollment is now open for both The 2X Group and The 2X Academy.

The 2X Group (Small Group Coaching): http://the2xgroup.com/

The 2X Academy (Online Virtual Training): http://the2xacademy.com

[smart_track_player url=”https://traffic.libsyn.com/secure/the2xpodcast/10-21-20-Basics.mp3″ title=”Back to the Basics” artist=”The Bill Caskey Podcast” image=”http://billcaskey.com/wp-content/uploads/2019/02/BC-Podcast-Artwork-copy-300×300.jpg” color=”#0f344a” background=”#0f344a” social_linkedin=”true” social_email=”true” ]

Also mentioned in this podcast:

  • Subscribe to Bill’s Youtube Channel
  • Subscribe to The Bill Caskey Podcast on iTunes
  • Learn more about The 2X Group – Mastermind

 

https://billcaskey.com/wp-content/uploads/2020/10/BC-Pod-10-21-20.jpg 585 1200 Bill Caskey https://billcaskey.com/wp-content/uploads/2018/05/BC-Logo-2018-Padding.png Bill Caskey2020-10-21 20:01:532020-10-21 20:01:53Back to the Basics

Where Are You Taking Your Customer?

October 7, 2020/in Career Advice, Communication Skills, Expert Positioning, General Tips, Goal Setting, Lead Generation, Mindset, Personal, Personal Productivity, Podcasts, Prospecting-Business Development, Sales Process, The Bill Caskey Podcast/by Bill Caskey

On this episode of the Bill Caskey Podcast, I discuss the idea of proper positioning. How do you position yourself in front of your ideal client or prospect and make them think, “I can’t live without this solution.”

If your closing percentage is not where it should be, chances are your prospect has no idea where you are taking them. And, that can all be solved by proper positioning.

To hear my interview with Jason Leister, marketing and business expert, go to https://caskeytraining.com/monthlybundle/mainwp/jason-leister-part-1/.

Also, enrollment is now open for both The 2X Group and The 2X Academy.

The 2X Group (Small Group Coaching): http://the2xgroup.com/

The 2X Academy (Online Virtual Training): http://the2xacademy.com

[smart_track_player url=”https://traffic.libsyn.com/secure/the2xpodcast/10-07-20-Positioning.mp3″ title=”Where Are You Taking Your Customer?” artist=”The Bill Caskey Podcast” image=”http://billcaskey.com/wp-content/uploads/2019/02/BC-Podcast-Artwork-copy-300×300.jpg” color=”#0f344a” background=”#0f344a” social_linkedin=”true” social_email=”true” ]

Also mentioned in this podcast:

  • Subscribe to Bill’s Youtube Channel
  • Subscribe to The Bill Caskey Podcast on iTunes
  • Learn more about The 2X Group – Mastermind

 

https://billcaskey.com/wp-content/uploads/2020/10/BC-Pod-10-07-20.jpg 675 1200 Bill Caskey https://billcaskey.com/wp-content/uploads/2018/05/BC-Logo-2018-Padding.png Bill Caskey2020-10-07 14:06:002020-10-07 14:06:48Where Are You Taking Your Customer?

The Importance of Mentorship with Mark Timm

September 30, 2020/in Career Advice, Communication Skills, Expert Interview, Expert Positioning, General Tips, Goal Setting, Mindset, Personal, Personal Productivity, Podcasts, The Bill Caskey Podcast/by Bill Caskey

On this episode of The Bill Caskey Podcast, I have a conversation with Mark Timm, Serial Entrepreneur and Exponential Thinking Practitioner.

We discuss his new book, Mentor to Millions, and how you can change your thinking in an exponential way.

Go to http://kevinmentor.com to your copy of Mentor to Millions and get over $1000 worth of bonuses for free.

Also, enrollment is now open for both The 2X Group and The 2X Academy.

The 2X Group (Small Group Coaching): http://the2xgroup.com/

The 2X Academy (Online Virtual Training): http://the2xacademy.com

[smart_track_player url=”https://traffic.libsyn.com/secure/the2xpodcast/09-30-20-MarkTimm.mp3″ title=”The Importance of Mentorship with Mark Timm” artist=”The Bill Caskey Podcast” image=”http://billcaskey.com/wp-content/uploads/2019/02/BC-Podcast-Artwork-copy-300×300.jpg” color=”#0f344a” background=”#0f344a” social_linkedin=”true” social_email=”true” ]

Also mentioned in this podcast:

  • Subscribe to Bill’s Youtube Channel
  • Subscribe to The Bill Caskey Podcast on iTunes
  • Learn more about The 2X Group – Mastermind

 

https://billcaskey.com/wp-content/uploads/2020/09/BC-Pod-09-30-20.jpg 390 800 Bill Caskey https://billcaskey.com/wp-content/uploads/2018/05/BC-Logo-2018-Padding.png Bill Caskey2020-09-30 07:00:452020-09-29 21:43:27The Importance of Mentorship with Mark Timm

The Awakening

September 23, 2020/in Career Advice, Communication Skills, Expert Positioning, General Tips, Goal Setting, Lead Generation, Mindset, Personal, Personal Productivity, Podcasts, Prospecting-Business Development, Sales Process, The Bill Caskey Podcast/by Bill Caskey

Who do you need to become to accomplish your goals?

If something is not working the way you want it to, you have to make a change. The problem is, we can’t change the world, but what we can change is ourselves.

Also, enrollment is now open for both The 2X Group and The 2X Academy.

The 2X Group (Small Group Coaching): http://the2xgroup.com/

The 2X Academy (Online Virtual Training): http://the2xacademy.com

[smart_track_player url=”https://traffic.libsyn.com/secure/the2xpodcast/09-23-20-WhoToBecome.mp3″ title=”Becoming a Contrarian in Your Sales Process” artist=”The Bill Caskey Podcast” image=”http://billcaskey.com/wp-content/uploads/2019/02/BC-Podcast-Artwork-copy-300×300.jpg” color=”#0f344a” background=”#0f344a” social_linkedin=”true” social_email=”true” ]

Also mentioned in this podcast:

  • Subscribe to Bill’s Youtube Channel
  • Subscribe to The Bill Caskey Podcast on iTunes
  • Learn more about The 2X Group – Mastermind

 

https://billcaskey.com/wp-content/uploads/2020/09/BC-Pod-09-23-20.jpg 675 1200 Bill Caskey https://billcaskey.com/wp-content/uploads/2018/05/BC-Logo-2018-Padding.png Bill Caskey2020-09-23 07:03:152020-09-22 20:07:10The Awakening

Becoming a Contrarian in Your Sales Process

September 18, 2020/in Career Advice, Communication Skills, Expert Positioning, General Tips, Goal Setting, Lead Generation, Mindset, Personal, Personal Productivity, Podcasts, Prospecting-Business Development, Sales Process, The Bill Caskey Podcast/by Bill Caskey

What if your customer or prospect actually sold you and begged to do business with you?

It is possible and I’ll give you some counterintuitive methods you can use to radically change your approach.

Also, enrollment is now open for both The 2X Group and The 2X Academy.

The 2X Group (Small Group Coaching): http://the2xgroup.com/

The 2X Academy (Online Virtual Training): http://the2xacademy.com

[smart_track_player url=”https://traffic.libsyn.com/secure/the2xpodcast/09-16-20-CounterIntuitive.mp3″ title=”Becoming a Contrarian in Your Sales Process” artist=”The Bill Caskey Podcast” image=”http://billcaskey.com/wp-content/uploads/2019/02/BC-Podcast-Artwork-copy-300×300.jpg” color=”#0f344a” background=”#0f344a” social_linkedin=”true” social_email=”true” ]

Also mentioned in this podcast:

  • Subscribe to Bill’s Youtube Channel
  • Subscribe to The Bill Caskey Podcast on iTunes
  • Learn more about The 2X Group – Mastermind

 

https://billcaskey.com/wp-content/uploads/2020/09/BC-Pod-09-16-20.jpg 675 1200 Bill Caskey https://billcaskey.com/wp-content/uploads/2018/05/BC-Logo-2018-Padding.png Bill Caskey2020-09-18 16:27:462020-09-18 16:27:46Becoming a Contrarian in Your Sales Process

How Do We Get Our Customers to Change?

September 10, 2020/in Career Advice, Communication Skills, Expert Positioning, General Tips, Goal Setting, Lead Generation, Mindset, Personal, Personal Productivity, Podcasts, Prospecting-Business Development, Sales Process, The Bill Caskey Podcast/by Bill Caskey

As a salesperson, you are a change agent. But, how do you do you work with a prospect who refuses to change?

On this episode of The Bill Caskey Podcast, I’ll give you 4 principles that you can use to help your customer perceive the value is adopting the change you’re offering.

Also, enrollment is now open for both The 2X Group and The 2X Academy.

The 2X Group (Small Group Coaching): http://the2xgroup.com/

The 2X Academy (Online Virtual Training): http://the2xacademy.com

[smart_track_player url=”https://traffic.libsyn.com/secure/the2xpodcast/09-10-20-Change.mp3″ title=”How Do We Get Our Customers to Change?” artist=”The Bill Caskey Podcast” image=”http://billcaskey.com/wp-content/uploads/2019/02/BC-Podcast-Artwork-copy-300×300.jpg” color=”#0f344a” background=”#0f344a” social_linkedin=”true” social_email=”true” ]

Also mentioned in this podcast:

  • Subscribe to Bill’s Youtube Channel
  • Subscribe to The Bill Caskey Podcast on iTunes
  • Learn more about The 2X Group – Mastermind

 

https://billcaskey.com/wp-content/uploads/2020/09/BC-Pod-09-10-20.jpg 675 1200 Bill Caskey https://billcaskey.com/wp-content/uploads/2018/05/BC-Logo-2018-Padding.png Bill Caskey2020-09-10 08:00:212020-09-09 19:48:17How Do We Get Our Customers to Change?

Is The Selling Profession Nearing Its End?

September 9, 2015/4 Comments/in General Tips/by Bill Caskey

This was a question posed at a recent panel discussion I was on. It was to a group of small business owners. I’m usually not a big fan of panel discussions due to the limited time each participant has to speak.

Venture Club - Panel

But this one was good…Ben Pidgeon, Barnes & Thornburg LLP, facilitated the event and we had awesome panelists: Jenny Vance (www.leadjen.com), Gary VanDeLaarschot (www.accelerate.com) and Adam Weber (www.GoBlueBridge.com).

Here’s my answer to the question of whether the salesperson is going away.

No….but.

No, the sales function is NOT going away anytime soon. But, the fact is that selling is changing. Here are my thoughts on how it’s changing and what you can do to cope, whether you’re a sales team leader or front-line seller.

1. Seller Must Offer Insight. You are not an order taker or an order maker. Most of the time, the customer has no earthly idea if they are in need of your solution or not. So, you must offer some form of “insight” to help guide the prospect along. That may be a case study, it may be a list of the trends you see impacting your clients, or it may be an article that you have published that positions you as an expert AND offers value. Don’t just run the prospect through your process. They deserve more than that. Read more

https://billcaskey.com/wp-content/uploads/2015/09/VentureClu-Panel.jpg 295 840 Bill Caskey https://billcaskey.com/wp-content/uploads/2018/05/BC-Logo-2018-Padding.png Bill Caskey2015-09-09 15:42:052015-09-11 17:49:25Is The Selling Profession Nearing Its End?
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  • Stop Cold Calling Forever: How AI Can 3X Your Sales
  • Staying Relevant After 50: Sales Success in a Changing World
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  • The 2X Roadmap: 10 Habits of High-Performers (Part 2)
  • The 2X Roadmap: 10 Habits of High-Performers (Part 1)

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Recent Posts

  • Stop Cold Calling Forever: How AI Can 3X Your Sales
  • Staying Relevant After 50: Sales Success in a Changing World
  • Buyer Behavior Revolution: Why Exceptional Talent Gets Average Results (Part 1)
  • The 2X Roadmap: 10 Habits of High-Performers (Part 2)
  • The 2X Roadmap: 10 Habits of High-Performers (Part 1)

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