Helping Entrepreneurs Gain Clarity And Get More Of What They Want From Their Business

Coaching, Guiding, and Transforming Entrepreneurial Business Leadership Teams

Area of Focus

As a small entrepreneurial business owner, you will never get the life you want and reach the goals you want for your business without systematizing your business.


Most entrepreneurial business leaders are experts in their field. Still, they struggle with the complexities involved in scaling their business, with less than half of entrepreneurial businesses surviving more than five years.

A serial entrepreneur himself, Jeff has “been there” and “done that” when it comes to both successful and less than successful ventures.

Today, he coaches entrepreneurs in building and structuring their businesses more like a franchise - i.e., scalable and systems-based - rather than a “job” that leaves them running on an everlasting hamster wheel, tried, burned out, and frustrated.

Suggested Topics:

What are the Four Key Areas that Drive Profits in a Small Business?
  1. People … having the right people, in the right seats
  2. Purpose … that all buy into a shared purpose and common goal
  3. Playbook … that all work from a proven playbook
  4. Performance … in a productive and efficient manner
What are the Stages that All Small Businesses must Navigate?
  1. Start Up … Pure survival, get your product or service to market before you run out of money
  2. Growth … Small boutique business, growing and having fun as the hamster wheel turns faster and faster
  3. Whitewater … Fun turns into a “job” with more time spent fire fighting than growth
  4. Systematized … The business is systematized, a foundation is laid for future sustainable growth
How does the Entrepreneur’s Role Change as the Business Grows?

The entrepreneur must change their mindset and actions from technician to owner, dealing with the challenges of managing people, projects, and issues from a high level instead of in the trenches.

What are the Key Components of an Effective Business Vision and how does the Business Leader make that Vision Actionable?
  1. Purpose … Why do we exist?
  2. Core Values … What should we or shouldn’t we do?
  3. Pinnacle … The mountain peak we are aiming for
  4. Milestones … 3-5 year objectives on the way to the Pinnacle
  5. Goals … 1-year objects on the way to the next Milestone
Head shots, logos, one sheet, etc.

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A few recent podcast appearances ...

Conversation 52: A Magnifying Conversation with Marc Marling of Corporate Thought

Thanks to Marc Marling and the Corporate Thought podcast for the recent episode with our own Jeff Chastain! Technology is an interesting thing.  In today’s technology-driven world, we are sitting at a desk with at least one computer at hand along with a cell phone that has more computing power than a computer had just 5 […]

Top 3 Ways To Break the Ceiling of Your Business with Mark Scribner of Oxygen Financial

Thanks to Mark Scribner and the Shrimp Tank Podcast podcast for the recent episode with our own Jeff Chastain! Climbing a mountain is a picture synonymous with the journey involved in building a business.  There is a pinnacle you are trying to reach, but each day involves a new climb. Along the way, gentle inclines may […]

From Zero to a Million with Zach Rego

Thanks to Zach Rego and the Zero to a Million podcast for the recent episode with our own Jeff Chastain! In this episode, Zach and Jeff talked about the four pillars to growing and scaling a business – people, purpose, playbook, and performance, as well as the definition of an “A” player and the need to […]

The Opposite Entrepreneur with Mike Regina

Thanks to Mike Regina and the Opposite Entrepreneur podcast for the recent episode with our own Jeff Chastain! In this episode, Mike and Jeff talked about leveraging vision planning strategies to help to grow and scale a business. Listen Now … Interested in applying these lessons to your business?

Entrepreneur Conundrum with Virginia Purnell

Thanks to Virginia Purnell and the Entrepreneur Conundrum podcast for the recent episode with our own Jeff Chastain! In this episode, Virginia and Jeff talked about the challenges involved in building an entrepreneurial business as some of the past successful (and less than successful) Jeff has been a part of over the years. Listen Now … […]

Good Advice: Do Business Better with Blake Binns

Thanks to Blake Binns and the Good Advice: Do Business Better podcast for the recent episode with our own Jeff Chastain! In this episode, Blake and Jeff talked about the challenges involved in building and growing an entrepreneurial business, specifically how complexity can creep in so fast. As Blake states, growing a business should not feel […]

Be an Entrepreneur and Not Technician with Allan Draper of the Business Growth Pod

Thanks to Allan Draper and the Business Growth Pod podcast for the recent episode with our own Jeff Chastain! In this episode, Allen and Jeff talk about the difference in being an Entrepreneur vs. a Technician – a critical difference that many new business owners struggle with when trying to grow their business. Many entrepreneurs […]

How to Avoid Chaos in Your Business with Laura Meyer of the Scale with Joy Podcast

Thank you to Laura Meyer and the Scale with Joy podcast for the recent episode with our own Jeff Chastain! In this episode, Laura and Jeff talk about the critical nature of having the right people, sitting in the right seats on your bus. As one of the 4 P’s (People, Purpose, Performance, and Playbook), […]

The Leadership Stack Podcast with Sean Si

Thanks to Sean Si and The Leadership Stack podcast for the recent episode with our own Jeff Chastain! Actually, Sean and Jeff dug into so many topics, the episode had to be broken up into 3! Listen Now … In this episode, Sean and Jeff break down some of the biggest challenges that entrepreneurs face when […]

How to Scale Your Small Business with Melinda Emerson of the #SmallBizChat Podcast

Thanks to Melinda Emerson and the Small Biz Chat podcast for the recent episode with our own Jeff Chastain! In this show, Melinda and Jeff talk about the mechanics involved with scaling a small business. Most small businesses are not operating at their true potential and the root issues are easily solvable. Listen as Melinda […]

A Cadence for Growth with Denise Cagan of DCA Virtual Business

Thanks to Denise Cagan and the Nurture Small Business podcast for the recent episode with our own Jeff Chastain! In this episode, Denise and Jeff talk about how business owners can establish a long-term cadence for predictable and stable growth with their business while gaining clarity and getting more of what they want from their […]

Your Entrepreneurial Operating System with Adam Kipnes of the Entrepreneur’s MBA Podcast

Thank you to Adam Kipnes and the Entrepreneur’s MBA podcast for the recent episode with our own Jeff Chastain! In this episode, Adam and Jeff talk about the importance of having a “system” when it comes to building and scaling your business. Just like a McDonald’s franchise has a “playbook” for how to run and […]

Proper Vision Planning with Steve Fredlund of the Small Small Business Podcast

Thanks to Steve Fredlund and the Small Small Business podcast for the recent episode with our own Jeff Chastain! In this show, Steve and Jeff talk proper vision planning when it comes to scaling a small business. There are techniques that you can use to get the entire team organized around that vision and pulling […]

Business Discipline and Accountability with Ann Brennan on the Small Business Connections Podcast

Thank you to Ann Brennan and the Small Business Connections podcast for the recent episode with our own Jeff Chastain! In this episode, Ann and Jeff talk about the importance of discipline and accountability when it comes to building and growing a small business. While still not a great idea, big corporations have big budgets […]

Building a Solid Business Foundation with Jake Carlson on the Modern Leadership Podcast

Thank you to Jake Carlson and the Modern Leadership podcast for the recent episode with our own Jeff Chastain! In this episode, Jake and Jeff talk about the importance of building a solid foundation for an entrepreneurial business to set it up for future growth. While looking specifically at the EOS business operating system, the […]

6 Keys to Successfully Scaling an Entrepreneurial Business with Jennifer Skidmore Calderon of The Vendor’s Daughter Podcast

Thanks to Jennifer Skidmore and The Vendor’s Daughter Podcast for the recent episode with our own Jeff Chastain! In this episode, Jennifer and Jeff talk about six keys that are critical to successfully scaling an entrepreneurial business. Building and scaling a business requires a system. Every business has a system – the way they operate, […]

How Entrepreneurs can Grow and Scale Their Business on The Mark Struczewski Podcast

Thank you to Mark Struczewski and the his podcast for the recent episode with our own Jeff Chastain! In this episode, Mark and Jeff talked through a number of topics that face entrepreneurial, growth oriented business leaders when trying to grow and scale their business including delegation and letting go, evaluating strengths and weaknesses, vision […]

Training Unleashed Podcast

Thank you to Evan Hackel and the Training Unleashed podcast for the recent episode! As Evan mentions during our conversation, challenges to a business can come in many forms. In fact, many businesses fail due to growing too fast or faced with landing that “whale” of a project, yet not being strong enough in their […]

Soul of Business Podcast

Thank you to Blaine Bartlett and the Soul of Business podcast for the recent episode! When you think of the soul of your business, what do you think of? This was a really interesting discussion as I had never thought about the soul in terms of business before speaking with Blaine. There are many definitions […]

The Minding Your Business Podcast

Thank you to Ron Brooks and the Minding Your Business podcast for the recent episode! When launching a new business venture, there are many things to think about, but at the same time, overthinking can be just as paralyzing. Even in these days, the number of new business ventures are growing and Ron has a […]

Humans Optimized: People + Technology

Thank you to Suzanne York and the Humans Optimized podcast for the recent opportunity to talk about the intersection of technology and business – one of our favorite topics! Technology can help propel virtually any business forward. It can speak up processes, make people more efficient and generally magnify the greatness of your business. What […]

Uncover Wealth Radio: Rekindle the Passion and Excitement For Your Business

Thank you to Annette Ferguson and the Uncover Wealth Radio podcast for the recent opportunity to talk about one of the challenges for many entrepreneurial business owners! When looking at the statistics, there are two major “humps” when it comes to the survival of small entrepreneurial businesses. The first is simply making it through the […]

Disruptive CEO Nation

Thank you to Allison Summers and the Disruptive CEO Nation podcast! As a company grows, it will inevitably hit one ceiling after another. The structure, the processes, the team, etc. that you have in place as a start up in the early days rarely continues to work when the company hits 25 employees and it […]

The Absolute Business Mindset Podcast

Thank you to Mark Hayward and the Absolute Business Mindset podcast! Throughout my personal entrepreneurial journey, I have always found my peers to be one of the best resources when it comes to overcoming challenges and finding new resources. In this episode, Mark and I had a great discussion about my journey – from corporate […]

Vision 33: Identifying Business Challenges and the Technology Cure with Entrepreneurial Operating Systems (EOS)

Thank you to Carl Lewis and the Connected Enterprise Podcast podcast! In this episode, Carl and I had a great discussion about the impacts of technology in growing and successful businesses. With my background as a fractional CTO, technology is a passion, but too often I saw business leaders attempting to use technology to solve […]

Business Built Freedom: Building a Foundation for Growth

Thank you to Josh Lewis and the Business Built Freedom podcast! In this episode, Josh and I had a great discussion about the necessity of building a strong foundation within your business in order to be able to successfully grow and scale that business moving forward. The reality is that the structure of your business […]

Sales POP!: How to get a Collective Vision and Keep Your Team Motivated

Thank you to John Golden and the Sales POP! podcast! In this episode, John and I took a look at one of the key struggles many entrepreneurs face in trying to scale their business – keeping the entire team focused and following the same vision. Having a singular focused vision for your business that is […]

Bold Business: UNCHARTED with Jeff Chastain

Thank you to Jess Dewell and the Bold Business podcast! In this episode, Jess and I had a great discussion about the idea of vision in business and how having a single focus and direction is so important for decision making to prevent wasted time, resources, and missed opportunities. Do you remember playing with LEGO […]

The Entrepreneur Way: Creating Strong Foundations to Make Your Company Grow

Thank you to Neil Ball and the Entrepreneur Way podcast! In this episode, Neil and I dived into my own personal entrepreneurial journey and the challenges I faced over the years launching and growing multiple businesses. One of the key points is in being able to set up the systems and processes such that you […]

The Business Mastermind: Where Business Owners Go Wrong When Scaling

Thank you to Gavin Preston and the ‘The Business Mastermind‘ podcast! In this episode, Gavin and I discussed the challenges business owners face when attempting to scale their business. We had a great discussion around the importance of spelling out the vision of the organization and how the tools within the EOS® (Entrepreneurial Operating System®) […]

The Thoughtful Entrepreneur: The EOS® Process

Thank you to Josh Elledge and his ‘The Thoughtful Entrepreneur‘ podcast! In this episode, Josh and I discussed the what EOS® (Entrepreneurial Operating System®) is and how it applies to entrepreneurial businesses. We took a quick pass through the six key areas (despite my loosing count) that every entrepreneurial business owner needs to focus on […]

The Growth Zone: Creating an Effective Vision for Your Business

Thank you to Christian Bartsch and his Growth Zone podcast! In this episode, Christian and I discussed the need for an effective vision in your business and dived into some of the details of what make an vision effective in propelling your business forward rather than just turning into a forgotten mission statement buried on […]