"Behind the Small Business" - brought to you by Centennial State Insurance Agency - is a podcast focused on the stories of small business owners in Colorado. These owners provide a glimpse behind who they are, what made them want to open a small business, as well as various other aspects of what it takes to be a successful small business owner. Whether you are a fellow small business owner, aspiring owner, or want to simply hear awesome stories from those in your communities, this is the podcast for you!
What would you do with more time back in your week? Matt Shepard of Shepard Consulting joins Kevin Dandino to discuss practical AI automation, reducing repetitive business tasks, and creating more room for life outside of work.
Matt shares how running construction and real estate businesses led him to build automation into his own operations. Now, he helps other small-business owners identify their biggest time drains and develop solutions around the way their businesses actually work.
The conversation explores starting with a manageable task, refining AI workflows, and building custom software when off-the-shelf tools don’t meet a business’s needs. Matt also explains his approach to working within a client’s budget and breaking larger projects into practical phases.
Beyond technology, Matt offers a valuable lesson for business owners: document your processes. Writing down the steps that currently live in your head can make training, delegation, automation, and an eventual business handoff easier to approach.
Whether you’re curious about AI or simply tired of spending your evenings catching up on administrative work, this conversation offers a grounded place to start.
Topics Covered
Getting started with AI: Identifying a simple, repetitive task to tackle first.
Setting expectations: Matt’s employee-training analogy for giving AI clear instructions and refining results.
Custom business software: A construction asset-tracking example built around a client’s specific needs.
Budget-conscious implementation: Prioritizing useful improvements and building in phases.
Documenting processes: Turning individual knowledge into repeatable business systems.
Work-life balance: Making time for family and life beyond the business.
Connect With Matt Shepard
Explore Matt’s work and contact him through Shepard Consulting (https://shepardconsulting.ai). Discuss the tasks consuming your time and what you’d like to improve.
Episode Sponsor
Behind the Small Business is sponsored by Centennial State Insurance Agency. For personal or business insurance questions and a free quote, call 303-838-0554 or visit Centennial State Insurance Agency (https://www.CentennialStateIns.com).
Proudly serving Colorado, Arizona, Nebraska, Kansas & Utah. Follow Behind the Small Business for more conversations with business owners about their experiences, lessons, and the work behind their businesses.
24 Aug 2026
Ep 50 - The Hamilton Collective
Host Kevin Dandino interviews Spencer Hamilton of The Hamilton Collective about building a community-first real estate business and navigating the foothills wildfire insurance crisis.
3 Aug 2026
Ep 49 - Newman Sauna Co. - Behind the Small Business
Host Kevin interviews Brett Newman, founder of Newman Sauna Co., about transforming a garage hobby into a custom wellness business after a career disruption.
Who has been a guest on Behind the Small Business
Names identified in recent episode analyses. Showing up to five guests.
Spencer Hamilton
Bret Newman
Helena Cappon
Thomas
Jack
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
5 ratings
Podcast Authority Score: 19 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
26
Social presence
0
YouTube
0
Engagement
32
Contact Behind the Small Business
Guest appearances
Books guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Questions about Behind the Small Business
Who hosts Behind the Small Business?
Kevin and Kevin Dandino host the show. Published by Kevin Dandino.
How often do new episodes come out?
The show publishes bi-weekly, based on its RSS feed.
Does Behind the Small Business take guests?
Yes. Guests have been identified in episode analyses.
Host of Behind the Small Business?
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