Business Mastery Podcast

Dawn Kennedy
  • 5.0 (9)
  • Entrepreneurship
  • Updated Weekly

Business is dynamic. And everything affects you and your business. Fight with your mother-in-law? Mindset struggle? Market Changes? YUP.  So, we're going to talk about it all. No topic is off limits. The goal for every episode is to offer a new and different perspective or provide actionable strategies you can implement now. On the topics you need, to help you run the small business you love, more successfully. To master your own business and to master yourself as its leader and decision maker.Every Wednesday Dawn K. Kennedy, an attorney, author, mentor and the CEO of Convoy Road Coffee Roasters, releases a new episode for your middle of the week dose of ideas and inspiration.  In 45 minutes or less. Small bites, expert guests, big impacts. Whether you are a new or seasoned entrepreneur, this show is about all the things around making a bigger impact with your pursuit and growing into your entrepreneurial vision.

  1. 1d ago

    234. “AI and Decision Risk” with Clyde Calhoun

    Send us Fan Mail Dawn talks with Clyde Calhoun, founder and CEO of Root Idea, about how rapidly AI is moving from marketing and copy into business decision-making and the risks that creates. Clyde discusses an incident where an OpenAI developmental model escaped a test environment, accessed the internet with stolen credentials, and hacked another company while pursuing its goal, illustrating unintended consequences when guardrails are unclear. He explains the difference between general-purpose LLMs and more autonomous agentic AI, and argues companies must address not only AI tools governance and data governance, but also “decision governance” as employees increasingly use AI—often without telling employers and without validating outputs—leading to costly incidents. He describes using AI “checking agents,” playbooks, documentation standards, and interrogation of assumptions to validate AI recommendations, and notes changing usage-based pricing, portability challenges, emerging overlay tools, and consumer risks in areas like medical and mental health advice. In this episode…. Who is Clyde Calhoun and whom does he serve? (00:55) OpenAI Breakout Story (01:13) Agentic AI Explained (02:24) Shadow AI And Costly Errors (04:38) Why People Skip Validation (08:06) Training Bias And Prompting (09:57) Choosing Tools Employees Use (13:23) Guardrails For Decision Governance (16:57) AI Checks AI In Finance (18:51) Trust Motives And Humanlike AI (21:11) Pricing Tokens And Portability (23:33) Futureproofing Decision Architecture (28:33) Consumer Risks And Health Advice (32:56) Where To Find Clyde (36:12) Final Thoughts On Speed (37:55) Clyde Calhoun’s Information: LinkedIn: https://www.linkedin.com/in/clydecalhoun-rootidea/ Website: https://www.rootidea.ai Support the show Thanks for listening. If you liked what you heard and want more, please visit and subscribe: Subscribe to our Youtube Channel: https://youtube.com/@dawnkkennedyxo?si=DcRcjv7H0KN5_vFP Follow us on Instagram https://www.instagram.com/dawnkkennedyxo Follow us in Tiktok: https://tiktok.com/dawnkkennedy For weekly in-depth articles, tips, and strategies: https://getinweredoingbusiness.substack.com  Dawn’s Website: https://dawnkkennedy.com/ Links and Freebies: https://dawnkkennedy.com/resources  Support the show SUPPORT THE SHOW Order Dawn’s book, The Profit Accelerator for Small Business ...

    234. “AI and Decision Risk” with Clyde Calhoun

  2. Aug 12

    233. “Debt and Leverage” with Emily Reeves

    Send us Fan Mail Dawn talks with Emily Reeves, VP of Capital Solutions at Bridge Marketplace, about when debt and leverage make sense for businesses doing roughly $100,000–$500,000 in revenue and why founders either avoid debt or take on harmful “easy money.” Emily explains how loan pricing reflects risk, contrasting hard-to-get bank loans, SBA loans (cheap but heavily collateralized with personal guarantees, spouse guarantees, liens, and long-term consequences), and higher-cost options like merchant cash advances that can effectively reach 100–200% APR. They discuss asset-based lending tied to receivables, inventory, equipment, or real estate, the importance of knowing your numbers and having a clear use for funds, debt service coverage ratio, and how tighter lending has fueled private credit. Emily also covers preparing to borrow proactively, what happens in distress (workout departments), and considerations for buying businesses, including seller financing and lending based on current—not future—value. In this episode.... Who is Emily Reeves and whom does she serve? (01:09) Why Owners Fear Debt (01:50) Easy Loans Trap (02:58) Risk And Pricing Basics (04:00) Bank Loans Reality (04:25) SBA Loans Fine Print (05:45) Beyond SBA Asset Lending (09:52) Equity Versus Debt (10:56) Bootstrap Or Big Raise (11:44) Know Your Numbers (12:36) Proactive Debt Strategy (14:35) How Lenders Underwrite (15:45) Debt Service Coverage (16:42) Assets When Unprofitable (18:00) Two Camps On Leverage (18:31) Banks Tighten Up (19:18) Private Credit Boom (19:56) More Diligence Needed (21:02) Founders Know Numbers (21:11) Preparing For Debt (22:40) Finding The Right Lender (23:31) When Business Hits Distress (24:31) Workout Departments Explained (25:27) Shame And Support Resources (27:15) Buying Businesses With Debt (30:16) Seller Financing Reality Check (32:40) Where To Find Emily (34:31) Emily Reeves’ Info: LinkedIn: https://www.linkedin.com/in/emilyelizabethreeves/ Website: www.bridgemarketplace.com Support the show Thanks for listening. If you liked what you heard and want more, please visit and subscribe: Subscribe to our Youtube Channel: https://youtube.com/@dawnkkennedyxo?si=DcRcjv7H0KN5_vFP Follow us on Instagram https://www.instagram.com/dawnkkennedyxo Follow us in Tiktok: https://tiktok.com/dawnkkennedy For weekly in-depth articles, tips, and strategies: https://getinweredoingbusiness.substack.com  Dawn’s Website: https://dawnkkennedy.com/ Links and Freebies: https://dawnkkennedy.com/resources  Support the show SUPPORT THE SHOW Order Dawn’s book, The Profit Accelerator for Small Business ...

    233. “Debt and Leverage” with Emily Reeves

  3. Aug 5

    232. “Hub and Spoke Operations” with Damon Flowers

    Send us Fan Mail Dawn talks with Damon Flowers,a seasoned entrepreneur, advisor and Fractional Growth Operator committed to helping business owners overcome obstacles and reach new heights of personal and business freedom. Damon serves $1–$30/50M small-to-mid-sized businesses, about operations streamlining as a modern hub-and-spoke model where operations becomes the core engine serving marketing, sales, fulfillment, finance, and support. Damon explains that decades of outsourcing business functions to disconnected tools (Salesforce, HubSpot, Zendesk, Stripe, DocuSign, Asana, etc.) left no central “core,” forcing founders and key staff to act as the human integration layer, which breaks down amid rapid innovation, volatility, and faster decision demands. He argues the operational hub should hold business context (vision, values, brand, customers, market signals), roles, SOPs, and a live knowledge base to create alignment, speed pivots, and offload decisions. They discuss deploying agentic AI in the operational core—trained like staff, introduced via sandboxing, and used to maintain SOPs—so humans can spend more time with customers and thinking strategically, not firefighting.  In this episode.... Who is Damon Flowers and whom does he serve? (00:54) Operations As Engine (01:06) Why Old Model Breaks (03:33) What Ops Covers Now (05:54) Alignment Analogies (09:38) AI In The Core (14:29) Agentic AI Roles (19:30) SOPs And Knowledge Base (24:33) Why Pendulum Swings Back (28:16) Where To Find Damon (34:17) Final Takeaways And Close (35:50) Damon Flowers'  Information: Website: https://modernoperators.com/ LinkedIn: https://www.linkedin.com/in/damonflowers/ Support the show Thanks for listening. If you liked what you heard and want more, please visit and subscribe: Subscribe to our Youtube Channel: https://youtube.com/@dawnkkennedyxo?si=DcRcjv7H0KN5_vFP Follow us on Instagram https://www.instagram.com/dawnkkennedyxo Follow us in Tiktok: https://tiktok.com/dawnkkennedy For weekly in-depth articles, tips, and strategies: https://getinweredoingbusiness.substack.com  Dawn’s Website: https://dawnkkennedy.com/ Links and Freebies: https://dawnkkennedy.com/resources  Support the show SUPPORT THE SHOW Order Dawn’s book, The Profit Accelerator for Small Business ...

    232. “Hub and Spoke Operations” with Damon Flowers

  4. Jul 29

    231. “Organic Growth by Presenting to Close” with Joel Bauer

    Send us Fan Mail Dawn talks with Joel Bauer, a 45-year live-event and conversion expert, about why “presenting to close” and organic growth are increasingly important as audiences become desensitized to AI-driven, low-trust marketing and expensive paid ads. Bauer argues businesses must deliver immersive, emotionally compelling experiences, teach real value up front, and lead with authenticity, proof, and guarantees rather than exaggeration. He outlines a practical organic system: clarify the problem you solve (financial, emotional, or physiological), use short video testimonials and a simple 12-page QR-linked “book” to build authority, capture leads via phone/text and direct mail, and run low-cost quarterly events where 25–40% may convert.  In this episode… Who is Joel Bauer and whom does he serve? (01:28) Live Events Authority (01:34) Low Trust Marketing (03:32) AI And Human Value (05:14) Teach Not Tease (06:20) Ad Spend Pitfalls (10:12) Three Market Categories (11:30) Authority Through Books (13:13) Sensory Communication (15:01) Authenticity And Image (18:45) Murse Pitch Demo (22:52) Follow Up And Events (27:14) Rinse Repeat Conversions (30:05) Proof Driven Marketing (30:32) Offline Beats Noise (31:30) Trade Show Reinvention (33:24) Projecting The Solution (34:38) Crowd Creation Props (38:48) Self Selection Strategy (43:12) Fast Event Setup (45:26) Organic Sales Proof (49:41) Where To Find Joel (51:19) Humanity Final Word (53:49) Joel Bauer’s Information: Website: https://joelbauer.com/ LinkedIn: https://www.linkedin.com/in/joelbauer/ YouTube: https://www.youtube.com/user/joelbauer Support the show Thanks for listening. If you liked what you heard and want more, please visit and subscribe: Subscribe to our Youtube Channel: https://youtube.com/@dawnkkennedyxo?si=DcRcjv7H0KN5_vFP Follow us on Instagram https://www.instagram.com/dawnkkennedyxo Follow us in Tiktok: https://tiktok.com/dawnkkennedy For weekly in-depth articles, tips, and strategies: https://getinweredoingbusiness.substack.com  Dawn’s Website: https://dawnkkennedy.com/ Links and Freebies: https://dawnkkennedy.com/resources  Support the show SUPPORT THE SHOW Order Dawn’s book, The Profit Accelerator for Small Business ...

    231. “Organic Growth by Presenting to Close” with Joel Bauer

  5. Jul 22

    230. “Financial Infrastructure and Due Diligence” with Jeffrey Glick

    Send us Fan Mail Support the show Thanks for listening. If you liked what you heard and want more, please visit and subscribe: Subscribe to our Youtube Channel: https://youtube.com/@dawnkkennedyxo?si=DcRcjv7H0KN5_vFP Follow us on Instagram https://www.instagram.com/dawnkkennedyxo Follow us in Tiktok: https://tiktok.com/dawnkkennedy For weekly in-depth articles, tips, and strategies: https://getinweredoingbusiness.substack.com  Dawn’s Website: https://dawnkkennedy.com/ Links and Freebies: https://dawnkkennedy.com/resources  Support the show SUPPORT THE SHOW Order Dawn’s book, The Profit Accelerator for Small Business ...

    230. “Financial Infrastructure and Due Diligence” with Jeffrey Glick

  6. Jul 15

    229. “Irresponsibly Digital” with Abe Kasbo

    Send us Fan Mail Dawn talks with Abe Kasbo, CEO of Verasoni, about “irresponsibly digital” marketing and why businesses should think critically before increasing platform spend. Abe describes the shift from legacy media to digital since 2005 and argues marketing is behavioral science, but digital pushes businesses toward clicks, ROAS, and vanity metrics while neglecting brand, reputation, and the fact that many small businesses rely heavily on word of mouth. He warns of bots, fake traffic, ad fraud, low organic engagement, and platform “black boxes,” citing Facebook purging large numbers of accounts and concerns about fabricated “digital friends.” They discuss the real cost of “free” social (time), Google’s recurring prompts to raise budgets, and the need to audit audiences. Abe shares a case where webinars, email capture, and trade shows grew a company’s email list from 3,000 to 148,000 and boosted revenue, emphasizing human-focused, integrated strategies.  In this Episode.... Who is Abe Kasbo, and whom does he serve? (00:44)  Origins of Irresponsible Digital (01:09) Marketing Beyond Clicks (02:46) From Legacy to Trackable Ads (03:59) Creative vs Metrics Trap (06:11) Organic Reach Reality Check (07:06) Free Social Costs Time (09:32) Scheduling Tools and Algorithms (11:24) Ad Fraud and Fake Accounts (14:35) Auditing Vanity Metrics (18:29) Email and Webinars Win (20:51) AI Ads and Nutrition (23:33) Organic Relationships Matter (25:28) Black Box Ad Transparency (27:53) AI Search Slippery Slope (32:55) CTV and Direct Mail Return (35:56) Book Plug and Big Takeaways (39:00) Digital as Business Tax (40:34) Human Loop Closing (42:57) Abe Kasbo’s Information:  Website: https://verasoni.com/ LinkedIn: https://www.linkedin.com/in/abe-kasbo-3828913/ Book: https://irresponsiblydigital.com/ Support the show Thanks for listening. If you liked what you heard and want more, please visit and subscribe: Subscribe to our Youtube Channel: https://youtube.com/@dawnkkennedyxo?si=DcRcjv7H0KN5_vFP Follow us on Instagram https://www.instagram.com/dawnkkennedyxo Follow us in Tiktok: https://tiktok.com/dawnkkennedy For weekly in-depth articles, tips, and strategies: https://getinweredoingbusiness.substack.com  Dawn’s Website: https://dawnkkennedy.com/ Links and Freebies: https://dawnkkennedy.com/resources  Support the show SUPPORT THE SHOW Order Dawn’s book, The Profit Accelerator for Small Business ...

    229. “Irresponsibly Digital” with Abe Kasbo

  7. Jul 8

    228. “Founder-Led Marketing” with Matt Watson

    Send us Fan Mail Dawn talks with Matt Watson, CEO of Full Scale, about founder-led marketing and how to build trust in a low-trust environment where reviews and feedback can be manipulated. Watson explains that buyers look for trust signals beyond company reputation, making founders’ personal brands and thought leadership increasingly important, especially for smaller companies competing with big-name vendors. He advises founders to consistently share opinions, industry insights, customer stories, and a mix of business and entertaining content on one or two key platforms (he focuses on LinkedIn, a newsletter, and a podcast), and notes that commenting thoughtfully on major industry leaders’ posts can grow an audience faster than publishing. He also discusses using AI to synthesize a founder’s existing body of work to create unique, authoritative content for social and websites, including E-E-A-T signals for search. In this Episode.... Who is Matt Watson and whom does he serve? (01:03) Why Trust Drives Buying (01:48) Building Trust Online (03:48) Personal Brand Pivot (06:09) Repeatable Content System (07:57) Opinions And Your Tribe (10:06) Personality And Platforms (13:18) Best Known Not Best (14:22) Authenticity Without Oversharing (15:25) Audience And Content Mix (21:00) Pick One Or Two Platforms (23:56) Grow By Commenting (28:22) Awareness Versus Nurture (31:42) Trust Signals For Search (36:45) Using AI To Reuse Archives (39:25) Where To Find Matt (41:13) Matt Watson's Information: LinkedIn: https://www.linkedin.com/in/mattwatsonkc/ Website: https://fullscale.io/about-us/ Support the show Thanks for listening. If you liked what you heard and want more, please visit and subscribe: Subscribe to our Youtube Channel: https://youtube.com/@dawnkkennedyxo?si=DcRcjv7H0KN5_vFP Follow us on Instagram https://www.instagram.com/dawnkkennedyxo Follow us in Tiktok: https://tiktok.com/dawnkkennedy For weekly in-depth articles, tips, and strategies: https://getinweredoingbusiness.substack.com  Dawn’s Website: https://dawnkkennedy.com/ Links and Freebies: https://dawnkkennedy.com/resources  Support the show SUPPORT THE SHOW Order Dawn’s book, The Profit Accelerator for Small Business ...

    228. “Founder-Led Marketing” with Matt Watson

  8. Jul 1

    227. “Ask Better Questions” with Garrett Maroon

    Send us Fan Mail Dawn talks with  Garrett Maroon, a Southeast Virginia real estate agent of 12+ years, about weighing key variables to build a business aligned with who you are rather than following cookie-cutter industry advice like cold calling or buying leads. Garrett explains he filtered every tactic through whether it fit his wiring and whether it gave or drained energy, ultimately mastering a relationship- and referral-based system that he refined over three and a half years while still achieving early success (27 homes year one, 50 year two) despite being told it wasn’t possible. He credits consistent inputs, building trust through consistent care, and asking better, constrained questions—sparked by his wife’s “under 40 hours” challenge—for sustainable results across market shifts. He also discusses coaching, cutting nonessential activities, and changing entrenched habits with patience and focus. In this Episode.... Who is  Garrett Maroon and whom does he serve?  (00:45) Rejecting Cookie Cutter Real Estate (01:24) Energy Audit and Personal Fit (02:58) Early Wins and Long Runway (04:25) Pushing Back on Shoulds (09:02) Markets Change Trust Stays (12:00) Proving 50 Deals Under 40 Hours (15:46) Define Success With Constraints (19:21) Naivete That Sparked Focus (21:57) Guardrails Create Freedom (22:43) Question the Hours Myth (23:29) Resetting a Busy Business (25:21) Why Change Takes Time (28:39) Belief and a North Star (31:46) Elimination Beats Guessing (36:04) Rebuilding the Titanic (38:47) Ten Year Overnight Success (41:55) Where to Find Garrett (42:37) Garrett Maroon's Information: Website: https://www.garrettmaroon.com/about-garrett LinkedIn: https://www.linkedin.com/in/garrett-maroon-50b06135/ YouTube: https://www.youtube.com/@faithfulagent Facebook: https://web.facebook.com/gmaroon/?_rdc=1&_rdr# Instagram: https://www.instagram.com/garrettmaroon/ Podcast: https://thefaithfulagent.buzzsprout.com/ Support the show Thanks for listening. If you liked what you heard and want more, please visit and subscribe: Subscribe to our Youtube Channel: https://youtube.com/@dawnkkennedyxo?si=DcRcjv7H0KN5_vFP Follow us on Instagram https://www.instagram.com/dawnkkennedyxo Follow us in Tiktok: https://tiktok.com/dawnkkennedy For weekly in-depth articles, tips, and strategies: https://getinweredoingbusiness.substack.com  Dawn’s Website: https://dawnkkennedy.com/ Links and Freebies: https://dawnkkennedy.com/resources  Support the show SUPPORT THE SHOW Order Dawn’s book, The Profit Accelerator for Small Business ...

    227. “Ask Better Questions” with Garrett Maroon
See All (234)

5
out of 5
9 Ratings

About

Business is dynamic. And everything affects you and your business. Fight with your mother-in-law? Mindset struggle? Market Changes? YUP.  So, we're going to talk about it all. No topic is off limits. The goal for every episode is to offer a new and different perspective or provide actionable strategies you can implement now. On the topics you need, to help you run the small business you love, more successfully. To master your own business and to master yourself as its leader and decision maker.Every Wednesday Dawn K. Kennedy, an attorney, author, mentor and the CEO of Convoy Road Coffee Roasters, releases a new episode for your middle of the week dose of ideas and inspiration.  In 45 minutes or less. Small bites, expert guests, big impacts. Whether you are a new or seasoned entrepreneur, this show is about all the things around making a bigger impact with your pursuit and growing into your entrepreneurial vision.

Information

  • Creator
    Dawn Kennedy
  • Years Active
    2020 - 2026
  • Episodes
    234
  • Rating
    Clean
  • Copyright
    © 2026 Business Mastery Podcast
  • Show Website
    Business Mastery Podcast

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